Skip to main content
SpringerLink
Log in

Carbohydrate Systems in Targeted Drug Delivery: Expectation and Reality

  • REVIEW ARTICLE
  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

In the end of the twentieth century, the world entered the era of high-tech and personalized medicine, characterized by the introduction of targeted drugs into clinical practice. Selective drug delivery became one of the most favorable ways to increase the efficacy and safety of chemotherapy. The current review is devoted to the study of carbohydrates in targeted drug delivery, particularly, in the treatment of oncological diseases. This review provides the analysis of numerous research papers, concerning the potential of mono- and oligosaccharides as vector ligands aimed at tumor- and tissue-specific receptors, and describes examples of carbohydrate conjugates containing various biologically active compounds, such as chemotherapeutic agents, photodynamic therapy agents, substrates for imaging in vitro and in vivo. The individual sections of this review are focused on the role of carbohydrates in tumor immunotherapy and the use of polysaccharides as nanocontainers for selective delivery of active substances, including nucleic acids. The problems and prospects of the biomedical application of carbohydrates and their mimetics as vectors for targeted delivery are discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.
Fig. 8.
Fig. 9.
Fig. 10.
Fig. 11.
Fig. 12.
Fig. 13.
Fig. 14.
Fig. 15.
Fig. 16.
Fig. 17.
Fig. 18.
Fig. 19.
Fig. 20.
Fig. 21.

Similar content being viewed by others

REFERENCES

  1. Lu, Z.-R. and Qiao, P., Mol. Pharm., 2018, vol. 15, pp. 3603–3616. https://doi.org/10.1021/acs.molpharmaceut.8b00037

    Article  CAS  PubMed  Google Scholar 

  2. Yoo, J., Park, C., Yi, G., Lee, D., and Koo, H., Cancers (Basel), 2019, vol. 11, p. 640. https://doi.org/10.3390/cancers11050640

    Article  CAS  PubMed Central  Google Scholar 

  3. Costa, A.F., Campos, D., Reis, C.A., and Gomes, C., Trends Cancer, 2020, vol. 6, pp. 757–766. https://doi.org/10.1016/j.trecan.2020.04.002

    Article  CAS  PubMed  Google Scholar 

  4. Kang, B., Opatz, T., Landfester, K., and Wurm, F.R., Chem. Soc. Rev., 2015, vol. 44, pp. 8301–8325. https://doi.org/10.1039/C5CS00092K

    Article  CAS  PubMed  Google Scholar 

  5. Ananikov, V.P., Eremin, D.B., Yakukhnov, S.A., Dilman, A.D., Levin, V.V., Egorov, M.P., Karlov, S.S., Kustov, L.M., Tarasov, A.L., Greish, A.A., Shesterkina, A.A., Sakharov, A.M., Nysenko, Z.N., Sheremetev, A.B., Stakheev, A.Yu., Mashkovsky, I.S., Sukhorukov, A.Yu., Ioffe, S.L., Terent’ev, A.O., Vil’, V.A., Tomilov, Y.V., Novikov, R.A., Zlotin, S.G., Kucherenko, A.S., Ustyuzhanina, N.E., Krylov, V.B., Tsvetkov, Y.E., Gening, M.L., and Nifantiev, N.E., Mendeleev Commun., 2017, vol. 27, pp. 425–438. https://doi.org/10.1016/j.mencom.2017.09.001

    Article  CAS  Google Scholar 

  6. Essentials of Glycobiology, 3rd ed., Varki, A., Cummings, R.D., Esko, J., Stanley, P., Hart, G.W., Aebi, M., Darvill, A.G., Kinoshita, T., Packer, N.H., Prestegard, J.H., Schnaar, R.L., and Seeberger, P.H., Eds. New York: Cold Spring Harbor, 2017.

  7. Sosicka, P., Ng, B.G., and Freeze, H.H., Biochemistry, 2020, vol. 59, pp. 3064–3077. https://doi.org/10.1021/acs.biochem.9b00565

    Article  CAS  PubMed  Google Scholar 

  8. Kleczkowski, L.A., Decker, D., and Wilczynska, M., Plant Physiol., 2011, vol. 156, pp. 3–10. https://doi.org/10.1104/pp.111.174706

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Iwamura, A., Watanabe, K., Akai, S., Nishinosono, T., Tsuneyama, K., Oda, S., Kume, T., and Yokoi, T., Drug Metab. Dispos., 2016, vol. 44, pp. 888–896. https://doi.org/10.1124/dmd.116.069575

    Article  CAS  PubMed  Google Scholar 

  10. Vigetti, D., Karousou, E., Viola, M., Deleonibus, S., De Luca, G., and Passi, A., Biochim. Biophys. Acta, 2014, vol. 1840, pp. 2452–2459. https://doi.org/10.1016/j.bbagen.2014.02.001

    Article  CAS  PubMed  Google Scholar 

  11. Li, Y. and Chen, X., Appl. Microbiol. Biotechnol., 2012, vol. 94, pp. 887–905. https://doi.org/10.1007/s00253-012-4040-1

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Sharipova, R.R., Garifullin, B.F., Sapunova, A.S., Voloshina, A.D., Kravchenko, M.A., and Kataev, V.E., Russ. J. Bioorg. Chem., 2019, vol. 45, pp. 155–164. https://doi.org/10.1134/S1068162019020110

    Article  CAS  Google Scholar 

  13. Niehues, R., Hasilik, M., Alton, G., Korner, C., Schiebe-Sukumar, M., Koch, H.G., Zimmer, K.P., Wu, R., Harms, E., Reiter, K., Figura, K., Freeze, H.H., Harms, H.K., and Marquardt, T., J. Clin. Invest., 1998, vol. 101, pp. 1414–1420. https://doi.org/10.1172/JCI2350

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Mention, K., Lacaille, F., Valayannopoulos, V., R-omano, S., Kuster, A., Cretz, M., Zaidan, H., Galmiche, L., Jaubert, F., de Keyzer, Y., Seta, N., and de Lonlay, P., Mol. Genet. Metab., 2008, vol. 93, pp. 40–43. https://doi.org/10.1016/j.ymgme.2007.08.126

    Article  CAS  PubMed  Google Scholar 

  15. Péanne, R., de Lonlay, P., Foulquier, F., Kornak, U., Lefeber, D.J., Morava, E., Pérez, B., Seta, N., Thiel, C., Van Schaftingen, E., Matthijs, G., and Jaeken, J., Eur. J. Med. Genet., 2018, vol. 61, pp. 643–663. https://doi.org/10.1016/j.ejmg.2017.10.012

    Article  PubMed  Google Scholar 

  16. Wong, S.Y.-W., Gadomski, T., van Scherpenzeel, M., Honzik, T., Hansikova, H., Holmefjord, K.S.B., Mork, M., Bowling, F., Sykut-Cegielska, J., Koch, D., Hertecant, J., Preston, G., Jaeken, J., Peeters, N., Perez, S., Nguyen, D.D., Crivelly, K., Emmerzaal, T., Gibson, K.M., Raymond, K., Abu Bakar, N., Foulquier, F., Poschet, G., Ackermann, A.M., He, M., Lefeber, D.J., Thiel, C., Kozicz, T., and Morava, E., Genet. Med., 2017, vol. 19, pp. 1226–1235. https://doi.org/10.1038/gim.2017.41

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Dörre, K., Olczak, M., Wada, Y., Sosicka, P., Grüneberg, M., Reunert, J., Kurlemann, G., Fiedler, B., Biskup, S., Hörtnagel, K., Rust, S., and Marquardt, T., J. Inherit. Metab. Dis., 2015, vol. 38, pp. 931–940. https://doi.org/10.1007/s10545-015-9828-6

    Article  CAS  PubMed  Google Scholar 

  18. Wild, M.K., Lühn, K., Marquardt, T., and Vestweber, D., Cells Tissues Organs, 2002, vol. 172, pp. 161–173. https://doi.org/10.1159/000066968

    Article  CAS  PubMed  Google Scholar 

  19. Ng, B.G. and Freeze, H.H., Trends Genet., 2018, vol. 34, pp. 466–476. https://doi.org/10.1016/j.tig.2018.03.002

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. Ivanov, D.O., Novikova, V.P., and Pokhlebkina, A.A., Pediatrician (St. Petersburg), 2018, vol. 9, pp. 5–15. https://doi.org/10.17816/PED935-15

    Article  Google Scholar 

  21. Gonzalez, P.S., O’Prey, J., Cardaci, S., Barthet, V.J.A., Sakamaki, J., Beaumatin, F., Roseweir, A., Gay, D.M., Mackay, G., Malviya, G., Kania, E., Ritchie, S., Baudot, A.D., Zunino, B., Mrowinska, A., Nixon, C., Ennis, D., Hoyle, A., Millan, D., McNeish, I.A., Sansom, O.J., Edwards, J., and Ryan, K.M., Nature, 2018, vol. 563, pp. 719–723. https://doi.org/10.1038/s41586-018-0729-3

    Article  CAS  PubMed  Google Scholar 

  22. Wood, F.C. and Cahill, G.F., J. Clin. Invest., 1963, vol. 42, pp. 1300–1312. https://doi.org/10.1172/JCI104814

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Sgambat, K., Banks, M., and Moudgil, A., Pediatr. Nephrol., 2013, vol. 28, pp. 2131–2135. https://doi.org/10.1007/s00467-013-2539-z

    Article  PubMed  Google Scholar 

  24. Hauber, H.-P., Schulz, M., Pforte, A., Mack, D., Zabel, P., and Schumacher, U., Int. J. Med. Sci., 2008, vol. 5, pp. 371–376. https://doi.org/10.7150/ijms.5.371

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Baenziger, J.U. and Fiete, D., Cell, 1980, vol. 22, pp. 611–620. https://doi.org/10.1016/0092-8674(80)90371-2

    Article  CAS  PubMed  Google Scholar 

  26. Rensen, P.C.N., van Leeuwen, S.H., Sliedregt, L.A.J.M., van Berkel, T.J.C., and Biessen, E.A.L., J. Med. Chem., 2004, vol. 47, pp. 5798–5808. https://doi.org/10.1021/jm049481d

    Article  CAS  PubMed  Google Scholar 

  27. Hangeland, J.J., Levis, J.T., Lee, Y.C., and Tso, P.O.P., Bioconjug. Chem., 1995, vol. 6, pp. 695–701. https://doi.org/10.1021/bc00036a006

    Article  CAS  PubMed  Google Scholar 

  28. Juliano, R.L., Ming, X., Carver, K., and Laing, B., Nucleic Acid Ther., 2014, vol. 24, pp. 101–113. https://doi.org/10.1089/nat.2013.0463

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. Prakash, T.P., Graham, M.J., Yu, J., Carty, R., Low, A., Chappell, A., Schmidt, K., Zhao, C., Aghajan, M., Murray, H.F., Riney, S., Booten, S.L., Murray, S.F., Gaus, H., Crosby, J., Lima, W.F., Guo, S., Monia, B.P., Swayze, E.E., and Seth, P.P., Nucleic Acids Res., 2014, vol. 42, pp. 8796–8807. https://doi.org/10.1093/nar/gku531

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. Yu, R.Z., Graham, M.J., Post, N., Riney, S., Zanardi, T., Hall, S., Burkey, J., Shemesh, C.S., Prakash, T.P., Seth, P.P., Swayze, E.E., Geary, R.S., Wang, Y., and Henry, S., Mol. Ther. Nucleic Acids, 2016, vol. 5, p. e317. https://doi.org/10.1038/mtna.2016.26

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  31. Li, Z., Kruijt, J.K., van der Sluis, R.J., Berkel, T.J.C.Van., and Hoekstra, M., Physiol. Genomics, 2013, vol. 45, pp. 268–275. https://doi.org/10.1152/physiolgenomics.00151.2012

    Article  CAS  PubMed  Google Scholar 

  32. Springer, A.D. and Dowdy, S.F., Nucleic Acid Ther., 2018, vol. 28, pp. 109–118. https://doi.org/10.1089/nat.2018.0736

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  33. Benizri, S., Gissot, A., Martin, A., Vialet, B., Grinstaff, M.W., and Barthelemy, P., Bioconjug. Chem., 2019, vol. 30, pp. 366–383. https://doi.org/10.1021/acs.bioconjchem.8b00761

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. Girelli, D., Busti, F., Marchi, G., Martinelli, N., and Olivieri, O., Int. Emerg. Med., 2018, vol. 13, pp. 313–318. https://doi.org/10.1007/s11739-018-1810-5

    Article  Google Scholar 

  35. Bennett, C.F. and Swayze, E.E., Annu. Rev. Pharmacol. Toxicol., 2010, vol. 50, pp. 259–293. https://doi.org/10.1146/annurev.pharmtox.010909.105654

    Article  CAS  PubMed  Google Scholar 

  36. Allerson, C.R., Sioufi, N., Jarres, R., Prakash, T.P., Naik, N., Berdeja, A., Wanders, L., Griffey, R.H., Swayze, E.E., and Bhat, B., J. Med. Chem., 2005, vol. 48, pp. 901–904. https://doi.org/10.1021/jm049167j

    Article  CAS  PubMed  Google Scholar 

  37. Nair, J.K., Attarwala, H., Sehgal, A., Wang, Q., Aluri, K., Zhang, X., Gao, M., Liu, J., Indrakanti, R., Schofield, S., Kretschmer, P., Brown, C.R., Gupta, S., Willoughby, J.L.S., Boshar, J.A., Jadhav, V., Charisse, K., Zimmermann, T., Fitzgerald, K., Manoharan, M., Rajeev, K.G., Akinc, A., Hutabarat, R., and Maier, M.A., Nucleic Acids Res., 2017, vol. 45, pp. 10 969–10 977. https://doi.org/10.1093/nar/gkx818

    Article  CAS  Google Scholar 

  38. Wada, F., Yamamoto, T., Ueda, T., Sawamura, M., Wada, S., Harada-Shiba, M., and Obika, S., Nucleic Acid Ther., 2018, vol. 28, pp. 50–57. https://doi.org/10.1089/nat.2017.0698

    Article  CAS  PubMed  Google Scholar 

  39. Yamamoto, T., Wada, F., and Harada-Shiba, M., J. Atheroscler. Thromb., 2016, vol. 23, pp. 1011–1025. https://doi.org/10.5551/jat.RV16001

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. Brown, J.M., Dahlman, J.E., Neuman, K.K., Prata, C.A.H., Krampert, M.C., Hadwiger, P.M., and Vornlocher, H.-P., Nucleic Acid Ther., 2019, vol. 29, pp. 231–244. https://doi.org/10.1089/nat.2019.0782

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  41. Weng, Y., Xiao, H., Zhang, J., Liang, X.-J., and Huang, Y., Biotechnol. Adv., 2019, vol. 37, pp. 801–825. https://doi.org/10.1016/j.biotechadv.2019.04.012

    Article  CAS  PubMed  Google Scholar 

  42. Hu, B., Zhong, L., Weng, Y., Peng, L., Huang, Y., Zhao, Y., and Liang, X.-J., Signal Transduct. Target. Ther., 2020, vol. 5, p. 101. https://doi.org/10.1038/s41392-020-0207-x

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  43. Craig, K., Abrams, M., and Amiji, M., Expert Opin. Drug Deliv., 2018, vol. 15, pp. 629–640. https://doi.org/10.1080/17425247.2018.1473375

    Article  CAS  PubMed  Google Scholar 

  44. Al Shaer, D., Al Musaimi, O., Albericio, F., and de la Torre, B.G., Pharmaceuticals, 2020, vol. 13, p. 40. https://doi.org/10.3390/ph13030040

    Article  CAS  PubMed Central  Google Scholar 

  45. de Paula Brandão, P.R., Titze-de-Almeida, S.S., and Titze-de-Almeida, R., Mol. Diagn. Ther., 2020, vol. 24, pp. 61–68. https://doi.org/10.1007/s40291-019-00438-6

    Article  CAS  PubMed  Google Scholar 

  46. Janas, M.M., Harbison, C.E., Perry, V.K., Carito, B., Sutherland, J.E., Vaishnaw, A.K., Keirstead, N.D., and Warner, G., Toxicol. Pathol., 2018, vol. 46, pp. 735–745. https://doi.org/10.1177/0192623318792537

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  47. Shen, X. and Corey, D.R., Nucleic Acids Res., 2018, vol. 46, pp. 1584–1600. https://doi.org/10.1093/nar/gkx1239

    Article  CAS  PubMed  Google Scholar 

  48. Zimmermann, T.S., Karsten, V., Chan, A., Chiesa, J., Boyce, M., Bettencourt, B.R., Hutabarat, R., Nochur, S., Vaishnaw, A., and Gollob, J., Mol. Ther., 2017, vol. 25, pp. 71–78. https://doi.org/10.1016/j.ymthe.2016.10.019

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  49. Cedillo, I., Dana, C., Engle, E., Chen, L., McPherson, A., and Rodriguez, A., Molecules, 2017, vol. 22, p. 1356. https://doi.org/10.3390/molecules22081356

    Article  CAS  PubMed Central  Google Scholar 

  50. Setten, R.L., Rossi, J.J., and Han, S., Nat. Rev. Drug Discov., 2019, vol. 18, pp. 421–446. https://doi.org/10.1038/s41573-019-0017-4

    Article  CAS  PubMed  Google Scholar 

  51. Soriano, V., AIDS Rev., 2018, vol. 20, pp. 125–127.

    Article  Google Scholar 

  52. Kim, Y., Jo, M., Schmidt, J., Luo, X., Prakash, T.P., Zhou, T., Klein, S., Xiao, X., Post, N., Yin, Z., and MacLeod, A.R., Mol. Ther., 2019, vol. 27, pp. 1547–1557. https://doi.org/10.1016/j.ymthe.2019.06.009

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  53. Zuckerman, J.E. and Davis, M.E., Nat. Rev. Drug Discov., 2015, vol. 14, pp. 843–856. https://doi.org/10.1038/nrd4685

    Article  CAS  PubMed  Google Scholar 

  54. Yang, B., Ming, X., Cao, C., Laing, B., Yuan, A., Porter, M.A., Hull-Ryde, E.A., Maddry, J., Suto, M., Janzen, W.P., and Juliano, R.L., Nucleic Acids Res., 2015, vol. 43, pp. 1987–1996. https://doi.org/10.1093/nar/gkv060

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  55. To, K.K.W., Fong, W., Tong, C.W.S., Wu, M., Yan, W., and Cho, W.C.S., Expert Opin. Drug Discov., 2020, vol. 15, pp. 63–83. https://doi.org/10.1080/17460441.2020.1690449

    Article  CAS  PubMed  Google Scholar 

  56. Cai, L., Gu, Z., Zhong, J., Wen, D., Chen, G., He, L., Wu, J., and Gu, Z., Drug Discov. Today, 2018, vol. 23, pp. 1126–1138. https://doi.org/10.1016/j.drudis.2018.02.009

    Article  CAS  PubMed  Google Scholar 

  57. Witzigmann, D., Quagliata, L., Schenk, S.H., Quintavalle, C., Terracciano, L.M., and Huwyler, J., Hepatol. Res., 2016, vol. 46, pp. 686–696. https://doi.org/10.1111/hepr.12599

    Article  CAS  PubMed  Google Scholar 

  58. Shi, B., Abrams, M., and Sepp-Lorenzino, L., J. Histochem. Cytochem., 2013, vol. 61, pp. 901–909. https://doi.org/10.1369/0022155413503662

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  59. Bunker, A., Magarkar, A., and Viitala, T., Biochim. Biophys. Acta, 2016, vol. 1858, pp. 2334–2352. https://doi.org/10.1016/j.bbamem.2016.02.025

    Article  CAS  PubMed  Google Scholar 

  60. Lee, Y. and Thompson, D.H., Wiley Interdiscip. Rev. Nanomed. Nanobiotechnol., 2017, vol. 9, p. e1450. https://doi.org/10.1002/wnan.1450

    Article  CAS  Google Scholar 

  61. El-Hammadi, M.M. and Arias, J.L., Expert Opin. Ther. Pat., 2019, vol. 29, pp. 891–907. https://doi.org/10.1080/13543776.2019.1679767

    Article  CAS  PubMed  Google Scholar 

  62. Basha, S.A., Salkho, N., Dalibalta, S., and Husseini, G.A., Mini Rev. Med. Chem., 2019, vol. 19, pp. 961–969. https://doi.org/10.2174/1389557519666190408155251

    Article  CAS  PubMed  Google Scholar 

  63. Olusanya, T., Haj, AhmadR., Ibegbu, D., Smith, J., and Elkordy, A., Molecules, 2018, vol. 23, p. 907. https://doi.org/10.3390/molecules23040907

    Article  CAS  PubMed Central  Google Scholar 

  64. Scheideler, M., Vidakovic, I., and Prassl, R., Chem. Phys. Lipids, 2020, vol. 226, p. 104 837. https://doi.org/10.1016/j.chemphyslip.2019.104837

    Article  CAS  Google Scholar 

  65. Salatin, S., Jelvehgari, M., Maleki-Dizaj, S., and Adibkia, K., Ther. Deliv., 2015, vol. 6, pp. 1017–1029. https://doi.org/10.4155/tde.15.28

    Article  CAS  PubMed  Google Scholar 

  66. Karimi, M., Bahrami, S., Ravari, S.B., Zangabad, P.S., Mirshekari, H., Bozorgomid, M., Shahreza, S., Sori, M., and Hamblin, M.R., Expert Opin. Drug Deliv., 2016, vol. 13, pp. 1609–1623. https://doi.org/10.1080/17425247.2016.1193149

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  67. Neek, M., Kim, T.I., and Wang, S.-W., Nanomedicine, 2019, vol. 15, pp. 164–174. https://doi.org/10.1016/j.nano.2018.09.004

    Article  CAS  PubMed  Google Scholar 

  68. Liu, K., Jiang, X., and Hunziker, P., Nanoscale, 2016, vol. 8, pp. 16 091–16 156. https://doi.org/10.1039/c6nr04489a

    Article  Google Scholar 

  69. Deirram, N., Zhang, C., Kermaniyan, S.S., Johnston, A.P.R., and Such, G.K., Macromol. Rapid Commun., 2019, vol. 40, p. e1 800 917. https://doi.org/10.1002/marc.201800917

    Article  CAS  Google Scholar 

  70. Zhao, K., Li, D., Shi, C., Ma, X., Rong, G., Kang, H., Wang, X., and Sun, B., Curr. Drug Deliv., 2016, vol. 13, pp. 494–499. https://doi.org/10.2174/156720181304160521004609

    Article  CAS  PubMed  Google Scholar 

  71. Ulbrich, K., Holá, K., Šubr, V., Bakandritsos, A., Tuček, J., and Zbořil, R., Chem. Rev., 2016, vol. 116, pp. 5338–5431. https://doi.org/10.1021/acs.chemrev.5b00589

    Article  CAS  PubMed  Google Scholar 

  72. Jaimes-Aguirre, L., Gibbens-Bandala, B.V., Morales-Avila, E., Ocampo-García, B.E., Seyedeh-Fatemeh, M., and Amirhosein, A., Curr. Pharm. Des, 2016, vol. 22, pp. 2886–2903. https://doi.org/10.2174/1381612822666160217125028

    Article  CAS  PubMed  Google Scholar 

  73. Kuznetsova, N.R., Svirshchevskaya, E.V., Sitnikov, N.S., Abodo, L., Sutorius, H., Zapke, J., Velder, J., Thomopoulou, P., Oschkinat, H., Prokop, A., Schmalz, H.-G., Fedorov, A.Yu., and Vodovozov, E.L., Russ. J. Bioorgan. Chem., 2013, vol. 39, pp. 543–552. https://doi.org/10.1134/S1068162013050105

    Article  CAS  Google Scholar 

  74. Guo, Q., Shen, X., Li, Y., and Xu, S., Curr. Med. Sci., 2017, vol. 37, pp. 635–641. https://doi.org/10.1007/s11596-017-1783-z

    Article  CAS  Google Scholar 

  75. Pardo, J., Peng, Z., and Leblanc, R., Molecules, 2018, vol. 23, p. 378. https://doi.org/10.3390/molecules23020378

    Article  CAS  PubMed Central  Google Scholar 

  76. Martincic, M. and Tobias, G., Expert Opin. Drug Deliv., 2015, vol. 12, pp. 563–581. https://doi.org/10.1517/17425247.2015.971751

    Article  CAS  PubMed  Google Scholar 

  77. Rode, A., Sharma, S., and Mishra, D.K., Curr. Drug Deliv., 2018, vol. 15, pp. 620–629. https://doi.org/10.2174/1567201815666171221124711

    Article  CAS  PubMed  Google Scholar 

  78. Chauhan, A., Molecules, 2018, vol. 23, p. e938. https://doi.org/10.3390/molecules23040938

    Article  CAS  PubMed  Google Scholar 

  79. Ray, S., Li, Z., Hsu, C.-H., Hwang, L.-P., Lin, Y.-C., Chou, P.-T., and Lin, Y.-Y., Theranostics, 2018, vol. 8, pp. 6322–6349. https://doi.org/10.7150/thno.27828

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  80. Huang, D. and Wu, D., Mater. Sci. Eng. C Mater. Biol. Appl., 2018, vol. 90, pp. 713–727. https://doi.org/10.1016/j.msec.2018.03.002

    Article  CAS  PubMed  Google Scholar 

  81. Sharma, A.K., Gothwal, A., Kesharwani, P., Alsaab, H., Iyer, A.K., and Gupta, U., Drug Discov. Today, 2017, vol. 22, pp. 314–326. https://doi.org/10.1016/j.drudis.2016.09.013

    Article  CAS  PubMed  Google Scholar 

  82. Wang, H., Huang, Q., Chang, H., Xiao, J., and Cheng, Y., Biomater. Sci., 2016, vol. 4, pp. 375–390. https://doi.org/10.1039/C5BM00532A

    Article  CAS  PubMed  Google Scholar 

  83. Hsu, H.-J., Bugno, J., Lee, S., and Hong, S., Wiley Interdiscip. Rev. Nanomed. Nanobiotechnol., 2017, vol. 9, p. e1409. https://doi.org/10.1002/wnan.1409

    Article  Google Scholar 

  84. Cabuzu, D., Cirja, A., Puiu, R., and Grumezescu, A., Curr. Top. Med. Chem., 2015, vol. 15, pp. 1605–1613. https://doi.org/10.2174/1568026615666150414144750

    Article  CAS  PubMed  Google Scholar 

  85. Daraee, H., Eatemadi, A., Abbasi, E., Fekri, AvalS., Kouhi, M., and Akbarzadeh, A., Artif. Cells Nanomed. Biotechnol., 2016, vol. 44, pp. 410–422. https://doi.org/10.3109/21691401.2014.955107

    Article  CAS  PubMed  Google Scholar 

  86. Kong, F.-Y., Zhang, J.-W., Li, R.-F., Wang, Z.-X., Wang, W.-J., and Wang, W., Molecules, 2017, vol. 22, p. E1445. https://doi.org/10.3390/molecules22091445

    Article  CAS  PubMed  Google Scholar 

  87. Connor, D.M. and Broome, A.-M., Adv. Cancer Res., 2018, vol. 139, pp. 163–184. https://doi.org/10.1016/bs.acr.2018.05.001

    Article  CAS  PubMed  Google Scholar 

  88. Gholipourmalekabadi, M., Mobaraki, M., Ghaffari, M., Zarebkohan, A., Omrani, V.F., Urbanska, A.M., and Seifalian, A., Curr. Pharm. Des., 2017, vol. 23, pp. 2918–2929. https://doi.org/10.2174/1381612823666170419105413

    Article  CAS  PubMed  Google Scholar 

  89. Alemzadeh, E., Dehshahri, A., Izadpanah, K., and Ahmadi, F., Colloids Surf. B Biointerfaces, 2018, vol. 167, pp. 20–27. https://doi.org/10.1016/j.colsurfb.2018.03.026

    Article  CAS  PubMed  Google Scholar 

  90. Shahgolzari, M., Pazhouhandeh, M., Milani, M., Khosroushahi, A.Y., and Fiering, S., Wiley Interdiscip. Rev. Nanomed. Nanobiotechnol., 2020, p. e1629. https://doi.org/10.1002/wnan.1629

  91. Sadauskas, E., Wallin, H., Stoltenberg, M., Vogel, U., Doering, P., Larsen, A., and Danscher, G., Part. Fibre Toxicol., 2007, vol. 4, p. 10. https://doi.org/10.1186/1743-8977-4-10

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  92. Nel, A.E., Mädler, L., Velegol., D., Xia, T., Hoek, E.M.V., Somasundaran, P., Klaessig, F., Castranova, V., and Thompson, M., Nat. Mater., 2009, vol. 8, pp. 543–557. https://doi.org/10.1038/nmat2442

    Article  CAS  PubMed  Google Scholar 

  93. Longmire, M., Choyke, P.L., and Kobayashi, H., Nanomedicine, 2008, vol. 3, pp. 703–717. https://doi.org/10.2217/17435889.3.5.703

    Article  CAS  PubMed  Google Scholar 

  94. Golombek, S.K., May, J.-N., Theek, B., Appold, L., Drude, N., Kiessling, F., and Lammers, T., Adv. Drug Deliv. Rev., 2018, vol. 130, pp. 17–38. https://doi.org/10.1016/j.addr.2018.07.007

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  95. Musumeci, F., Radi, M., Brullo, C., and Schenone, S., J. Med. Chem., 2012, vol. 55, pp. 10 797–10 822. https://doi.org/10.1021/jm301085w

    Article  CAS  Google Scholar 

  96. Cheung, A., Bax, H.J., Josephs, D.H., Ilieva, K.M., Pellizzari, G., Opzoomer, J., Bloomfield, J., Fittall, M., Grigoriadis, A., Figini, M., Canevari, S., Spicer, J.F., Tutt, A.N., and Karagiannis, S.N., Oncotarget, 2016, vol. 7, pp. 52 553–52 574. https://doi.org/10.18632/oncotarget.9651

    Article  Google Scholar 

  97. Raz, A. and Nakahara, S., Anticancer Agents Med. Chem., 2008, vol. 8, pp. 22–36. https://doi.org/10.2174/187152008783330833

    Article  PubMed  PubMed Central  Google Scholar 

  98. Du, J., Lane, L.A., and Nie, S., J. Control. Release, 2015, vol. 219, pp. 205–214. https://doi.org/10.1016/j.jconrel.2015.08.050

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  99. Zhou, L., Wang, H., and Li, Y., Theranostics, 2018, vol. 8, pp. 1059–1074. https://doi.org/10.7150/thno.22679

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  100. Tang, Q., Yu, B., Gao, L., Cong, H., Song, N., and Lu, C., Curr. Med. Chem., 2018, vol. 25, pp. 1837–1866. https://doi.org/10.2174/0929867325666180111095913

    Article  CAS  PubMed  Google Scholar 

  101. Park, J.H., Cho, Y.W., Son, Y.J., Kim, K., Chung, H., Jeong, S.Y., Choi, K., Park, C.R., Park, R.-W., Kim, I.-S., and Kwon, I.C., Colloid Polym. Sci., 2006, vol. 284, pp. 763–770. https://doi.org/10.1007/s00396-005-1438-7

    Article  CAS  Google Scholar 

  102. Ai, S., Zhen, S., Liu, Z., Sun, F., He, X., Chu, F., Guan, W., and Wang, J., RSC Adv., 2018, vol. 8, pp. 30 012–30 020. https://doi.org/10.1039/C8RA05071F

    Article  Google Scholar 

  103. Khatun, Z., Nurunnabi, M., Reeck, G.R., Cho, K.J., and Lee, Y., J. Control. Release, 2013, vol. 170, pp. 74–82. https://doi.org/10.1016/j.jconrel.2013.04.024

    Article  CAS  PubMed  Google Scholar 

  104. Son, Y., J. Control. Release, 2003, vol. 91, pp. 135–145. https://doi.org/10.1016/S0168-3659(03)00231-1

    Article  CAS  PubMed  Google Scholar 

  105. Park, J.H., Kwon, S., Lee, M., Chung, H., Kim, J.-H., Kim, Y.-S., Park, R.-W., Kim, I.-S., Seo, S.B., Kwon, I.C., and Jeong, S.Y., Biomaterials, 2006, vol. 27, pp. 119–126. https://doi.org/10.1016/j.biomaterials.2005.05.028

    Article  CAS  PubMed  Google Scholar 

  106. Lee, E., Lee, J., Lee, I.-H., Yu, M., Kim, H., Chae, S.Y., and Jon, S., J. Med. Chem., 2008, vol. 51, pp. 6442–6449. https://doi.org/10.1021/jm800767c

    Article  CAS  PubMed  Google Scholar 

  107. Fattahi, A., Asgarshamsi, M., Hasanzadeh, F., Varshosaz, J., Rostami, M., Mirian, M., and Sadeghi-aliabadi, H., J. Mater. Sci. Mater. Med., 2015, vol. 26, p. 119. https://doi.org/10.1007/s10856-015-5407-5

    Article  CAS  PubMed  Google Scholar 

  108. Gong, X.-Y., Yin, Y.-H., Huang, Z.-J., Lu, B., Xu, P.-H., Zheng, H., Xiong, F.-L., Xu, H.-X., Xiong, X., and Gu, X.-B., Int. J. Pharm., 2012, vol. 436, pp. 240–247. https://doi.org/10.1016/j.ijpharm.2012.06.043

    Article  CAS  PubMed  Google Scholar 

  109. Huang, S. and Huang, G., Drug Deliv., 2019, vol. 26, pp. 252–261. https://doi.org/10.1080/10717544.2019.1580322

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  110. Tran, T.H., Bae, B., Lee, Y., Na, K., and Huh, K.M., Carbohydr. Res., 2013, vol. 92, pp. 1615–1624. https://doi.org/10.1016/j.carbpol.2012.10.075

    Article  CAS  Google Scholar 

  111. Wang, X., Lang, S., Tian, Y., Zhang, J., Yan, X., Fang, Z., Weng, J., Lu, N., Wu, X., Li, T., Cao, H., Li, Z., and Huang, X., ACS Cent. Sci., 2020, vol. 6, pp. 382–389. https://doi.org/10.1021/acscentsci.9b00956

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  112. Han, J., Park, W., Park, S., and Na, K., ACS Appl. Mater. Interfaces, 2016, vol. 8, pp. 7739–7747. https://doi.org/10.1021/acsami.6b01664

    Article  CAS  PubMed  Google Scholar 

  113. Svenson, S., Wolfgang, M., Hwang, J., Ryan, J., and Eliasof, S., J. Control. Release, 2011, vol. 153, pp. 49–55. https://doi.org/10.1016/j.jconrel.2011.03.007

    Article  CAS  PubMed  Google Scholar 

  114. Shahriari, M., Taghdisi, S.M., Abnous, K., Ramezani, M., and Alibolandi, M., Int. J. Pharm., 2019, vol. 572, p. 118 835. https://doi.org/10.1016/j.ijpharm.2019.118835

    Article  CAS  Google Scholar 

  115. Lee, J.-Y., Lee, H.S., Kang, N.-W., Lee, S.Y., Kim, D.H., Kim, S., Yoon, I.-S., Cho, H.-J., and Kim, D.-D., Carbohydr. Res., 2020, vol. 230, p. 115 568. https://doi.org/10.1016/j.carbpol.2019.115568

    Article  CAS  Google Scholar 

  116. Gotov, O., Battogtokh, G., and Ko, Y.T., Mol. Pharm., 2018, vol. 15, pp. 4668–4676. https://doi.org/10.1021/acs.molpharmaceut.8b00640

    Article  CAS  PubMed  Google Scholar 

  117. Cadete, A., Olivera, A., Besev, M., Dhal, P.K., Goncalves, L., Almeida, A.J., Bastiat, G., Benoit, J.-P., de la Fuente, M., Garcia-Fuentes, M., Alonso, M.J., and Torres, D., Sci. Rep., 2019, vol. 9, p. 11 565. https://doi.org/10.1038/s41598-019-47995-8

    Article  CAS  Google Scholar 

  118. Liu, J., Liang, N., Li, S., Han, Y., Yan, P., Kawashima, Y., Cui, F., and Sun, S., J. Biomater. Appl., 2020, vol. 34, pp. 1458–1469. https://doi.org/10.1177/0885328220905256

    Article  CAS  PubMed  Google Scholar 

  119. Li, H., Zhang, P., Luo, J., Hu, D., Huang, Y., Zhang, Z.-R., Fu, Y., and Gong, T., ACS Nano, vol. 13, no. 2019, pp. 9386–9396. https://doi.org/10.1021/acsnano.9b04166

  120. Zhou, H., Yu, W., Guo, X., Liu, X., Li, N., Zhang, Y., and Ma, X., Biomacromolecules, 2010, vol. 11, pp. 3480–3486. https://doi.org/10.1021/bm100989x

    Article  CAS  PubMed  Google Scholar 

  121. Kim, J.-H., Kim, Y.-S., Park, K., Lee, S., Nam, H.Y., Min, K.H., Jo, H.G., Park, J.H., Choi, K., Jeong, S.Y., Park, R.-W., Kim, I.-S., Kim, K., and Kwon, I.C., J. Control. Release, 2008, vol. 127, pp. 41–49. https://doi.org/10.1016/j.jconrel.2007.12.014

    Article  CAS  PubMed  Google Scholar 

  122. Hwang, H.-Y., Kim, I.-S., Kwon, I.C., and Kim, Y.-H., J. Control. Release, 2008, vol. 128, pp. 23–31. https://doi.org/10.1016/j.jconrel.2008.02.003

    Article  CAS  PubMed  Google Scholar 

  123. Deng, L., Wang, G., Ren, J., Zhang, B., Yan, J., Li, W., and Khashab, N.M., RSC Adv., 2012, vol. 2, pp. 12 909–12 914. https://doi.org/10.1039/c2ra21888g

    Article  CAS  Google Scholar 

  124. You, J., Hu, F.-Q., Du, Y.-Z., and Yuan, H., Biomacromolecules, 2007, vol. 8, pp. 2450–2456. https://doi.org/10.1021/bm070365c

    Article  CAS  PubMed  Google Scholar 

  125. Hu, F.-Q., Ren, G.-F., Yuan, H., Du, Y.-Z., and Zeng, S., Colloids Surf., 2006, vol. 50, pp. 97–103. https://doi.org/10.1016/j.colsurfb.2006.04.009

    Article  CAS  Google Scholar 

  126. Hu, F.-Q., Wu, X., Du, Y.-Z., You, J., and Yuan, H., Eur. J. Pharm. Biopharm., 2008, vol. 69, pp. 117–125. https://doi.org/10.1016/j.ejpb.2007.09.018

    Article  CAS  PubMed  Google Scholar 

  127. You, J., Li, X., de Cui, F., Du, Y.-Z., Yuan, H., and Hu, F.Q., Nanotecnology, 2008, vol. 19, p. 045 102. https://doi.org/10.1088/0957-4484/19/04/045102

    Article  CAS  Google Scholar 

  128. Qin, Y., Chen, J., Bi, Y., Xu, X., Zhou, H., Gao, J., Hu, Y., Zhao, Y., and Chai, Z., Acta Biomater., 2015, vol. 17, pp. 201–209. https://doi.org/10.1016/j.actbio.2015.01.026

    Article  CAS  PubMed  Google Scholar 

  129. Tan, Y. and Liu, C.-G., Colloids Surf., 2009, vol. 69, pp. 178–182. https://doi.org/10.1016/j.colsurfb.2008.11.026

    Article  CAS  Google Scholar 

  130. Cao, J., Huang, S., Chen, Y., Li, S., Li, X., Deng, D., Qian, Z., Tang, L., and Gu, Y., Biomaterials, 2013, vol. 34, pp. 6272–6283. https://doi.org/10.1016/j.biomaterials.2013.05.008

    Article  CAS  PubMed  Google Scholar 

  131. Gao, C., Liu, T., Dang, Y., Yu, Z., Wang, W., Guo, J., Zhang, X., He, G., Zheng, H., Yin, Y., and Kong, X., Carbohydr. Res., 2014, vol. 111, pp. 964–970. https://doi.org/10.1016/j.carbpol.2014.05.012

    Article  CAS  Google Scholar 

  132. Zhang, P., Wu, J., Xiao, F., Zhao, D., and Luan, Y., Med. Res. Rev., 2018, vol. 38, pp. 1485–1510. https://doi.org/10.1002/med.21485

    Article  CAS  PubMed  Google Scholar 

  133. Tao, Y., Han, J., and Dou, H., J. Mater. Chem., 2012, vol. 22, pp. 8930–8937. https://doi.org/10.1039/c2jm30290j

    Article  CAS  Google Scholar 

  134. Liang, D.-S., Su, H.-T., Liu, Y.-J., Wang, A.-T., and Qi, X.-R., Biomaterials, 2015, vol. 71, pp. 11–23. https://doi.org/10.1016/j.biomaterials.2015.08.035

    Article  CAS  PubMed  Google Scholar 

  135. Zhao, Z., He, M., Yin, L., Bao, J., Shi, L., Wang, B., Tang, C., and Yin, C., Biomacromolecules, 2009, vol. 10, pp. 565–572. https://doi.org/10.1021/bm801225m

    Article  CAS  PubMed  Google Scholar 

  136. Gref, R., Minamitake, Y., Peracchia, M., Trubetskoy, V., Torchilin, V., and Langer, R., Science, 1994, vol. 263, pp. 1600–1603. https://doi.org/10.1126/science.8128245

    Article  CAS  PubMed  Google Scholar 

  137. Vernaez, O., Neubert, K.J., Kopitzky, R., and Kabasci, S., Polymers (Basel), 2019, vol. 11, p. 1939. https://doi.org/10.3390/polym11121939

    Article  CAS  PubMed Central  Google Scholar 

  138. Ibrahim, A.G., Am. J. Polym. Sci. Technol., 2019, vol. 5, pp. 55–62. https://doi.org/10.11648/j.ajpst.20190502.13

    Article  Google Scholar 

  139. Polymer Grafting and Crosslinking, Bhattacharya, A., Rawlins, J.W., and Ray, P., Eds., Hoboken, NJ, USA: Wiley, 2008. https://doi.org/10.1002/9780470414811

    Book  Google Scholar 

  140. Choi, K.Y., Yoon, H.Y., Kim, J.-H., Bae, S.M., Park, R.-W., Kang, Y.M., Kim, I.-S., Kwon, I.C., Choi, K., Jeong, S.Y., Kim, K., and Park, J.H., ACS Nano, vol. 5, no. 2011, pp. 8591–8599. https://doi.org/10.1021/nn202070n

  141. Han, H.S., Lee, J., Kim, H.R., Chae, S.Y., Kim, M., Saravanakumar, G., Yoon, H.Y., You, D.G., Ko, H., Kim, K., Kwon, I.C., Park, J.C., and Park, J.H., J. Control. Release, 2013, vol. 168, pp. 105–114. https://doi.org/10.1016/j.jconrel.2013.02.022

    Article  CAS  PubMed  Google Scholar 

  142. Werle, M. and Bernkop-Schnürch, A., J. Pharm. Pharmacol., 2008, vol. 60, pp. 273–281. https://doi.org/10.1211/jpp.60.3.3001

    Article  CAS  PubMed  Google Scholar 

  143. Werle, M. and Hoffer, M., J. Control. Release, 2006, vol. 111, pp. 41–46. https://doi.org/10.1016/j.jconrel.2005.11.011

    Article  CAS  PubMed  Google Scholar 

  144. Kamra, M., Moitra, P., Ponnalagu, D., Karande, A.A., and Bhattacharya, S., ACS Appl. Mater. Interfaces, 2019, vol. 11, pp. 37 442–37 460. https://doi.org/10.1021/acsami.9b09485

    Article  CAS  Google Scholar 

  145. Cao, Y., Tan, Y.F., Wong, Y.S., Liew, M.W.J., and Venkatraman, S., Mar. Drugs, 2019, vol. 17, p. 381. https://doi.org/10.3390/md17060381

    Article  CAS  PubMed Central  Google Scholar 

  146. Wang, B., He, C., Tang, C., and Yin, C., Biomaterials, 2011, vol. 32, pp. 4630–4638. https://doi.org/10.1016/j.biomaterials.2011.03.003

    Article  CAS  PubMed  Google Scholar 

  147. Serrano-Sevilla, I., Artiga, A., Mitchell, S.G., De Matteis, L., and de la Fuente, J.M., Molecules, 2019, vol. 24, p. 2570. https://doi.org/10.3390/molecules24142570

    Article  CAS  PubMed Central  Google Scholar 

  148. Mao, S., Sun, W., and Kissel, T., Adv. Drug Deliv. Rev., 2010, vol. 62, pp. 12–27. https://doi.org/10.1016/j.addr.2009.08.004

    Article  CAS  PubMed  Google Scholar 

  149. Chen, C.-K., Huang, P.-K., Law, W.-C., Chu, C.-H., Chen, N.-T., and Lo, L.-W., Int. J. Nanomed., 2020, vol. 15, pp. 2131–2150. https://doi.org/10.2147/IJN.S222419

    Article  CAS  Google Scholar 

  150. Wang, Y., Ye, M., Xie, R., and Gong, S., Bioconjug. Chem., 2019, vol. 30, pp. 325–337.

    Article  Google Scholar 

  151. Dosio, F., Arpicco, S., Stella, B., and Fattal, E., Adv. Drug Deliv. Rev., 2016, vol. 97, pp. 204–236. https://doi.org/10.1016/j.addr.2015.11.011

    Article  CAS  PubMed  Google Scholar 

  152. Jacob, S. and Nair, A.B., Drug Dev. Res., 2018, vol. 79, pp. 201–217. https://doi.org/10.1002/ddr.21452

    Article  CAS  PubMed  Google Scholar 

  153. Zhao, F., Yin, H., and Li, J., Biomaterials, 2014, vol. 35, pp. 1050–1062. https://doi.org/10.1016/j.biomaterials.2013.10.044

    Article  CAS  PubMed  Google Scholar 

  154. Novikov, B.N., Grimsley, J.K., Kern, R.J., Wild, J.R., and Wales, M.E., J. Control. Release, 2010, vol. 146, pp. 318–325. https://doi.org/10.1016/j.jconrel.2010.06.003

    Article  CAS  PubMed  Google Scholar 

  155. Díaz-Moscoso, A., Le Gourriérec, L., Gómez-García, M., Benito, J., Balbuena, P., Ortega-Caballero, F., Guilloteau, N., Di Giorgio, C., Vierling, P., Defaye, J., Mellet, C.O., and Fernández, J.M.G., Chem. J., 2009, vol. 15, pp. 12 871–12 888. https://doi.org/10.1002/chem.200901149

    Article  CAS  Google Scholar 

  156. Zuckerman, J.E., Gritli, I., Tolcher, A., Heidel, J.D., Lim, D., Morgan, R., Chmielowski, B., Ribas, A., Davis, M.E., and Yen, Y., Proc. Natl. Acad. Sci. U. S. A., 2014, vol. 111, pp. 11 449–11 454. https://doi.org/10.1073/pnas.1411393111

    Article  CAS  Google Scholar 

  157. Huang, G. and Huang, H., J. Control. Release, 2018, vol. 278, pp. 122–126. https://doi.org/10.1016/j.jconrel.2018.04.015

    Article  CAS  PubMed  Google Scholar 

  158. Bachar, G., Cohen, K., Hod, R., Feinmesser, R., Mizrachi, A., Shpitzer, T., Katz, O., and Peer, D., Biomaterials, 2011, vol. 32, pp. 4840–4848. https://doi.org/10.1016/j.biomaterials.2011.03.040

    Article  CAS  PubMed  Google Scholar 

  159. Mattheolabakis, G., Milane, L., Singh, A., and Amiji, M.M., J. Drug Target, 2015, vol. 23, pp. 605–618. https://doi.org/10.3109/1061186X.2015.1052072

    Article  CAS  PubMed  Google Scholar 

  160. Spadea A., Rios de la Rosa, J.M., Tirella, A., Ashford, M.B., Williams, K.J., Stratford, I.J., Tirelli, N., and Mehibel, M., Mol. Pharm., 2019, vol. 16, pp. 2481–2493. https://doi.org/10.1021/acs.molpharmaceut.9b00083

    Article  CAS  PubMed  Google Scholar 

  161. Yang, C., Li, C., Zhang, P., Wu, W., and Jiang, X., Theranostics, 2017, vol. 7, pp. 1719–1734. https://doi.org/10.7150/thno.18340

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  162. Miyazaki, M., Yuba, E., Hayashi, H., Harada, A., and Kono, K., Bioconjug. Chem., 2018, vol. 29, pp. 44–55. https://doi.org/10.1021/acs.bioconjchem.7b00551

    Article  CAS  PubMed  Google Scholar 

  163. Jiang, D., Liang, J., and Noble, P.W., Physiol. Rev., 2011, vol. 91, pp. 221–264. https://doi.org/10.1152/physrev.00052.2009

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  164. Casu, B. and Lindahl, U., in Advances in Carbohydrate Chemistry and Biochemistry, Elsevier, 2001, pp. 159–206. https://doi.org/10.1016/S0065-2318(01)57017-1

    Book  Google Scholar 

  165. Chemistry and Biology of Heparin and Heparan Sulfate, Garg, H.G., Linhardt, R.J., and Hales, C.A., Eds., Elsevier, 2005. https://doi.org/10.1016/B978-0-08-044859-6.X5000-X

    Book  Google Scholar 

  166. Xu, W., Qian, J., Zhang, Y., Suo, A., Cui, N., Wang, J., Yao, Y., and Wang, H., Acta Biomater., 2016, vol. 33, pp. 131–141. https://doi.org/10.1016/j.actbio.2016.01.027

    Article  CAS  PubMed  Google Scholar 

  167. Fu, H.-G., Chen, Y., Yu, Q., and Liu, Y., ACS Med. Chem. Lett., 2020, vol. 11, pp. 1191–1195. https://doi.org/10.1021/acsmedchemlett.0c00040

    Article  CAS  PubMed  Google Scholar 

  168. Cai, Z., Zhang, H., Wei, Y., and Cong, F., Biomacromolecules, 2017, vol. 18, pp. 1677–1696. https://doi.org/10.1021/acs.biomac.7b00424

    Article  CAS  PubMed  Google Scholar 

  169. Xu, W., Qian, J., Hou, G., Wang, Y., Wang, J., Sun, T., Ji, L., Suo, A., and Yao, Y., Acta Biomater., 2019, vol. 83, pp. 400–413. https://doi.org/10.1016/j.actbio.2018.11.026

    Article  CAS  PubMed  Google Scholar 

  170. Ernsting, M.J., Tang, W.-L., Maccallum n., li s.-d, Bioconjug. Chem., 2011, vol. 22, pp. 2474–2486. https://doi.org/10.1021/bc200284b

    Article  CAS  PubMed  Google Scholar 

  171. Dai, L. and Si, C., Curr. Med. Chem., 2019, vol. 26, pp. 2410–2429. https://doi.org/10.2174/0929867324666170711131353

    Article  CAS  PubMed  Google Scholar 

  172. Huang, G. and Huang, H., Nanomedicine, 2018, vol. 13, pp. 3149–3158. https://doi.org/10.2217/nnm-2018-0331

    Article  CAS  PubMed  Google Scholar 

  173. Varshosaz, J., Expert Opin. Drug Deliv., 2012, vol. 9, pp. 509–523. https://doi.org/10.1517/17425247.2012.673580

    Article  CAS  PubMed  Google Scholar 

  174. Severino, P., Silva, C.F., Andrade, L.N., de Lima, OliveiraD., Campos, J., and Souto, E.B., Curr. Pharm. Des., 2019, vol. 25, pp. 1312–1334. https://doi.org/10.2174/1381612825666190425163424

    Article  CAS  PubMed  Google Scholar 

  175. The Danish Enoxaparin Study Group, Arch. Int. Med., 1991, vol. 151, pp. 1621–1624. https://doi.org/10.1001/archinte.151.8.1621

  176. Kucera, S.U., DiNunzio, J.C., Kaneko, N., and McGinity, J.W., Drug Dev. Ind. Pharm., 2012, vol. 38, pp. 341–350. https://doi.org/10.3109/03639045.2011.604328

    Article  CAS  PubMed  Google Scholar 

  177. Leiman, D.A., Riff, B.P., Morgan, S., Metz, D.C., Falk, G.W., French, B., Umscheid, C.A., and Lewis, J.D., Dis. Esophagus, 2017, vol. 30, pp. 1–8. https://doi.org/10.1111/dote.12535

    Article  PubMed  PubMed Central  Google Scholar 

  178. Lavín de Juan, L., García Recio V., Jiménez López, P., Girbés Juan, T., Cordoba-Diaz, M., and Cordoba-D-iaz, D., J. Drug Deliv. Sci. Technol., 2017, vol. 42, pp. 126–133. https://doi.org/10.1016/j.jddst.2017.05.018

    Article  CAS  Google Scholar 

  179. Ensign, L.M., Cone, R., and Hanes, J., Adv. Drug Deliv. Rev., 2012, vol. 64, pp. 557–570. https://doi.org/10.1016/j.addr.2011.12.009

    Article  CAS  PubMed  Google Scholar 

  180. Li, H., Dong, W., Zhou, J., Xu, X., and Li, F., Int. J. Pharm., 2013, vol. 449, pp. 37–43. https://doi.org/10.1016/j.ijpharm.2013.04.008

    Article  CAS  PubMed  Google Scholar 

  181. Cousin, J. and Cloninger, M., Int. J. Mol. Sci., 2016, vol. 17, p. 1566. https://doi.org/10.3390/ijms17091566

    Article  CAS  PubMed Central  Google Scholar 

  182. Ingrassia, L., Nshimyumukiza, P., Dewelle, J., Lefranc, F., Wlodarczak, L., Thomas, S., Dielie, G., Chiron, C., Zedde, C., Tisnès, P., van Soest, R., Braekman, J.C., Darro, F., and Kiss, R., J. Med. Chem., 2006, vol. 49, pp. 1800–1807. https://doi.org/10.1021/jm050971v

    Article  CAS  PubMed  Google Scholar 

  183. Daniotti, J.L., Lardone, R.D., and Vilcaes, A.A., Front. Oncol., 2016, vol. 5, p. 300. https://doi.org/10.3389/fonc.2015.00300

    Article  PubMed  PubMed Central  Google Scholar 

  184. Wu, M., Li, H., Liu, R., Gao, X., Zhang, M., Liu, P., Fu, Z., Yang, J., Zhang-Negrerie, D., and Gao, Q., Eur. J. Med. Chem., 2016, vol. 110, pp. 32–42. https://doi.org/10.1016/j.ejmech.2016.01.016

    Article  CAS  PubMed  Google Scholar 

  185. Chen, F., Huang, G., and Huang, H., Future Med. Chem., 2020, vol. 12, pp. 161–171. https://doi.org/10.4155/fmc-2019-0114

    Article  CAS  PubMed  Google Scholar 

  186. Singh, S., Aggarwal, A., Thompson, S., Tomé, J.P.C., Zhu, X., Samaroo, D., Vinodu, M., Gao, R., and Drain, C.M., Bioconjug. Chem., 2010, vol. 21, pp. 2136–2146. https://doi.org/10.1021/bc100356z

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  187. Pereira, P.M.R., Rizvi, W., Bhupathiraju, N.V.S.D.K., Berisha, N., Fernandes, R., Tome, J.P.C., and Drain, C.M., Bioconjug. Chem., 2018, vol. 29, pp. 306–315. https://doi.org/10.1021/acs.bioconjchem.7b00636

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  188. Otvagin, V.F., Kuzmina, N.S., Krylova, L.V., Volovetsky, A.B., Nyuchev, A.V., Gavryushin, A.E., Meshkov, I.N., Gorbunova, Y.G., Romanenko, Y.V., Koifman, O.I., Balalaeva, I.V., and Fedorov, A.Yu., J. Med. Chem., 2019, vol. 62, pp. 11 182–11 193. https://doi.org/10.1021/acs.jmedchem.9b01294

    Article  CAS  Google Scholar 

  189. Bocker, S., Laaf, D., and Elling, L., Biomolecules, 2015, vol. 5, pp. 1671–1696. https://doi.org/10.3390/biom5031671

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  190. Yuan, S.S., Li, M.L., Chen, J.S., Zhou, L., and Zhou, W., Chem. Med. Chem., 2018, vol. 13, pp. 764–778. https://doi.org/10.1002/cmdc.201700762

    Article  CAS  PubMed  Google Scholar 

  191. Parker, N., Turk, M.J., Westrick, E., Lewis, J.D., Low, P.S., and Leamon, C.P., Anal. Biochem., 2005, vol. 338, pp. 284–293. https://doi.org/10.1016/j.ab.2004.12.026

    Article  CAS  PubMed  Google Scholar 

  192. Low, P.S. and Kularatne, S.A., Curr. Opin. Chem. Biol., 2009, vol. 13, pp. 256–262.

    Article  CAS  Google Scholar 

  193. Wee, P. and Wang, Z., Cancers (Basel), 2017, vol. 9.

  194. Salomon, D.S., Brandt, R., Ciardiello, F., and Normanno, N., Crit. Rev. Oncol. Hematol., 1995, vol. 19, pp. 183–232.

    Article  CAS  Google Scholar 

  195. Jin, F. and Wang, F., Glycoconj. J., 2020, vol. 37, pp. 277–291.

    Article  CAS  Google Scholar 

  196. Scarà, S., Bottoni, P., and Scatena, R., in Advances in Cancer Biomarkers. Advances in Experimental Medicine and Biology, Scatena R., Ed., Dordrecht: Springer, 2015, pp. 247–260. https://doi.org/10.1007/978-94-017-7215-0_15

    Book  Google Scholar 

  197. Trinchera, M., Aronica, A., and Dall’Olio, F., Biology (Basel), 2017, vol. 6, p. 16. https://doi.org/10.3390/biology6010016

    Article  PubMed Central  Google Scholar 

  198. Awad, S., Alkashash, A.M., Amin, M., Baker, S.J., and Rose, J.B., Front. Oncol., 2020, vol. 10, p. 620. https://doi.org/10.3389/fonc.2020.00620

    Article  PubMed  PubMed Central  Google Scholar 

  199. Ferreira, I., Carrascal, M., Mineiro, A., Bugalho, A., Borralho, P., Silva, Z., Dall’olio, F., and Videira, P., Int. J. Oncol., 2019, vol. 55, pp. 1033–1048. https://doi.org/10.3892/ijo.2019.4886

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  200. Hashida, N., Ohguro, N., Yamazaki, N., Arakawa, Y., Oiki, E., Mashimo, H., Kurokawa, N., and Tano, Y., Exp. Eye Res., 2008, vol. 86, pp. 138–149. https://doi.org/10.1016/j.exer.2007.10.004

    Article  CAS  PubMed  Google Scholar 

  201. Arakawa, Y., Hashida, N., Ohguro, N., Yamazaki, N., Onda, M., Matsumoto, S., Ohishi, M., Yamabe, K., Tano, Y., and Kurokawa, N., Biomed. Res., 2007, vol. 28, pp. 331–334. https://doi.org/10.2220/biomedres.28.331

    Article  CAS  PubMed  Google Scholar 

  202. Moiseeva, E.V., Kuznetsova, N.R., Svirshchevskaya, E.V., Bovin, N.V., Sitnikov, N.S., Shavyrin, A.S., Beletskaya, I.P., Combes, S., Fedorov, A.Y., and Vodovozova, E.L., Biochemistry (Moscow) Suppl. Ser. B, 2011, vol. 5, p. 276. https://doi.org/10.1134/S1990750811030073

    Article  Google Scholar 

  203. Kuznetsova, N.R., Stepanova, E.V., Peretolchina, N.M., Khochenkov, D.A., Boldyrev, I.A., Bovin, N.V., and Vodovozova, E.L., J. Drug Target., 2014, vol. 22, pp. 242–250. https://doi.org/10.3109/1061186X.2013.862805

    Article  CAS  PubMed  Google Scholar 

  204. Alekseeva, A., Kapkaeva, M., Shcheglovitova, O., Boldyrev, I., Pazynina, G., Bovin, N., and Vodovozova, E., Biochim. Biophys. Acta, 2015, vol. 1848, pp. 1099–1110. https://doi.org/10.1016/j.bbamem.2015.01.016

    Article  CAS  PubMed  Google Scholar 

  205. Vodovozova, E.L., Moiseeva, E.V., Grechko, G.K., Gayenko, G.P., Nifant’ev, N.E., Bovin, N.V., and Molotkovsky, J.G., Eur. J. Cancer, 2000, vol. 36, pp. 942–949. https://doi.org/10.1016/S0959-8049(00)00029-0

    Article  CAS  PubMed  Google Scholar 

  206. Kuznetsova, N.R., Gaenko, G.P., Haidukov, S.V., Bovin, N.V., and Vodovozova, E.L., Russ. J. Bioorg. Chem., 2009, vol. 35, pp. 490–496. https://doi.org/10.1134/S1068162009040116

    Article  CAS  Google Scholar 

  207. Kuznetsova, N.R., Sevrin, C., Lespineux, D., Bovin, N.V., Vodovozova, E.L., Meszaros, T., Szebeni, J., and Grandfils, C., J. Control. Release, 2012, vol. 160, pp. 394–400. https://doi.org/10.1016/j.jconrel.2011.12.010

    Article  CAS  PubMed  Google Scholar 

  208. Kishimoto, S., Fujitani, N., Ohnishi, T., Aoki, H., Suzuki, R., and Fukushima, S., Anticancer Res., 2017, vol. 37, pp. 6055–6061. https://doi.org/10.21873/anticanres.12053

    Article  CAS  PubMed  Google Scholar 

  209. Mizushina, Y., Hada, T., and Yoshida, H., Oncol. Rep., 2012, vol. 28, pp. 821–828. https://doi.org/10.3892/or.2012.1893

    Article  CAS  PubMed  Google Scholar 

  210. Tsuruta, W., Tsurushima, H., Yamamoto, T., Suzuki, K., Yamazaki, N., and Matsumura, A., Biomaterials, 2009, vol. 30, pp. 118–125. https://doi.org/10.1016/j.biomaterials.2008.09.009

    Article  CAS  PubMed  Google Scholar 

  211. Stahn, R., Grittner, C., Zeisig, R., Karsten, U., Felix, S.B., and Wenzel, K., Cell. Mol. Life Sci., 2001, vol. 58, pp. 141–147. https://doi.org/10.1007/PL00000774

    Article  CAS  PubMed  Google Scholar 

  212. Yamada, Y., Kobayashi, H., Iwasa, M., Sumi, S., Ushikoshi, H., Aoyama, T., Nishigaki, K., Takemura, G., Fujiwara, T., Fujiwara, H., Kiso, M., and Minatoguchi, S., Am. J. Physiol. Circ. Physiol., 2013, vol. 304, pp. H1124–H1133. https://doi.org/10.1152/ajpheart.00707.2012

    Article  CAS  Google Scholar 

  213. Ansboro, S., Greiser, U., Barry, F., and Murphy, M., Eur. Cells Mater., 2012, vol. 23, pp. 310–319. https://doi.org/10.22203/eCM.v023a24

    Article  CAS  Google Scholar 

  214. Hudak, J.E. and Bertozzi, C.R., Chem. Biol., 2014, vol. 21, pp. 16–37. https://doi.org/10.1016/j.chembiol.2013.09.010

    Article  CAS  PubMed  Google Scholar 

  215. Sarkar, D., Vemula, P.K., Zhao, W., Gupta, A., Karnik, R., and Karp, J.M., Biomaterials, 2010, vol. 31, pp. 5266–5274. https://doi.org/10.1016/j.biomaterials.2010.03.006

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  216. Heimburg-Molinaro, J., Lum, M., Vijay, G., Jain, M., Almogren, A., and Rittenhouse-Olson, K., Vaccine, 2011, vol. 29, pp. 8802–8826. https://doi.org/10.1016/j.vaccine.2011.09.009

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  217. Feng, D., Shaikh, A.S., and Wang, F., ACS Chem. Biol., 2016, vol. 11, pp. 850–863. https://doi.org/10.1021/acschembio.6b00084

    Article  CAS  PubMed  Google Scholar 

  218. Guo, J., Jiang, W., Li, Q., Jaiswal, M., and Guo, Z., Carbohydr. Res., 2020, vol. 492, p. 107 999. https://doi.org/10.1016/j.carres.2020.107999

    Article  CAS  Google Scholar 

  219. Mettu, R., Chen, C.-Y., and Wu, C.-Y., J. Biomed. Sci., 2020, vol. 27, p. 9. https://doi.org/10.1186/s12929-019-0591-0

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  220. Saboural, P., Chaubet, F., Rouzet, F., Al-Shoukr, F., Azzouna, R., Bouchemal, N., Picton, L., Louedec, L., Maire, M., Rolland, L., Potier, G., Guludec, D.L., Letourneur, D., and Chauvierre, C., Mar. Drugs, 2014, vol. 12, pp. 4851–4867. https://doi.org/10.3390/md12094851

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  221. Barbosa, A.I., Coutinho, A.J., Costa, LimaS.A., and Reis, S., Mar. Drugs, 2019, vol. 17, p. 654. https://doi.org/10.3390/md17120654

    Article  CAS  PubMed Central  Google Scholar 

  222. Cumashi, A., Ushakova, N.A., Preobrazhenskaya, M.E., D’Incecco, A., Piccoli, A., Totani, L., Tinari, N., Morozevich, G.E., Berman, A.E., Bilan, M.I., Usov, A.I., Ustyuzhanina, N.E., Grachev, A.A., Sanderson, C.J., Kelly, M., Rabinovich, G.A., Iacobelli, S., and Nifantiev, N.E., Glycobiology, 2007, vol. 17, pp. 541–552. https://doi.org/10.1093/glycob/cwm014

    Article  CAS  PubMed  Google Scholar 

  223. Shamay, Y., Elkabets, M., Li, H., Shah, J., Brook, S., Wang, F., Adler, K., Baut, E., Scaltriti, M., Jena, P.V., Gardner, E.E., Poirier, J.T., Rudin, C.M., Baselga, J., Haimovitz-Friedman, A., and Heller, D.A., Sci. Transl. Med., 2016, vol. 8, p. 345ra87. https://doi.org/10.1126/scitranslmed.aaf7374

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  224. Forero, RamirezL.M., Gobin, E., Aid-Launais, R., Journe, C., Moraes, F.C., Picton, L., Le Cerf, D., Letourneur, D., Chauvierre, C., and Chaubet, F., Carbohydr. Res., 2020, vol. 245, p. 116 457. https://doi.org/10.1016/j.carbpol.2020.116457

    Article  CAS  Google Scholar 

  225. Juenet, M., Aid-Launais, R., Li, B., Berger, A., Aerts, J., Ollivier, V., Nicoletti, A., Letourneur, D., and Chauvierre, C., Biomaterials, 2018, vol. 156, pp. 204–216. https://doi.org/10.1016/j.biomaterials.2017.11.047

    Article  CAS  PubMed  Google Scholar 

  226. Fitton, H.J., Stringer, D.S., Park, A.Y., and Karpiniec, S.N., Mar. Drugs, 2019, vol. 17, p. 571. https://doi.org/10.3390/md17100571

    Article  CAS  PubMed Central  Google Scholar 

  227. Zheng, K.H., Kaiser, Y., Poel, E., Verberne, H., Aerts, J., Rouzet, F., Stroes, E., Letourneur, D., and Chauvierre, C., Atherosclerosis, 2019, vol. 287, p. e143. https://doi.org/10.1016/j.atherosclerosis.2019.06.425

    Article  Google Scholar 

  228. Hsu, H. and Hwang, P., Clin. Transl. Med., 2019, vol. 8, p. e15. https://doi.org/10.1186/s40169-019-0234-9

    Article  Google Scholar 

  229. Khatuntseva, E.A., Ustuzhanina, N.E., Zatonskii, G.V., Shashkov, A.S., Usov, A.I., and Nifant’ev, N.E., J. Carbohydr. Chem., 2000, vol. 19, pp. 1151–1173. https://doi.org/10.1080/07328300008544140

    Article  CAS  Google Scholar 

  230. Krylov, V.B., Kaskova, Z.M., Vinnitskiy, D.Z., Ustyuzhanina, N.E., Grachev, A.A., Chizhov, A.O., and Nifantiev, N.E., Carbohydr. Res., 2011, vol. 346, pp. 540–550. https://doi.org/10.1016/j.carres.2011.01.005

    Article  CAS  PubMed  Google Scholar 

  231. Ustyuzhanina, N., Krylov, V., Grachev, A., Gerbst, A., and Nifantiev, N., Synthesis (Stuttg.), 2006, vol. 2006, pp. 4017–4031. https://doi.org/10.1055/s-2006-950333

    Article  CAS  Google Scholar 

  232. Vinnitskiy, D.Z., Krylov, V.B., Ustyuzhanina, N.E., Dmitrenok, A.S., and Nifantiev, N.E., Org. Biomol. Chem., 2016, vol. 14, pp. 598–611. https://doi.org/10.1039/C5OB02040A

    Article  CAS  PubMed  Google Scholar 

  233. Batzke, K., Buchel, G., Hansen, W., and Schramm, A., Int. J. Mol. Sci., 2018, vol. 19, p. 718. https://doi.org/10.3390/ijms19030718

    Article  CAS  PubMed Central  Google Scholar 

  234. Duan, S. and Paulson, J.C., Annu. Rev. Immunol., 2020, vol. 38, pp. 365–395. https://doi.org/10.1146/annurev-immunol-102419-035900

    Article  CAS  PubMed  Google Scholar 

  235. Daly, J., Carlsten, M., and O’Dwyer, M., Front. Immunol., 2019, vol. 10, p. 1047. https://doi.org/10.3389/fimmu.2019.01047

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  236. Wang, J., Sun, J., Liu, L.N., Flies, D.B., Nie, X., Tok-i, M., Zhang, J., Song, C., Zarr, M., Zhou, X., Han, X., Archer, K.A., O’Neill, T., Herbst, R.S., B-oto, A.N., Sanmamed, M.F., Langermann, S., Rimm, D.L., and Chen, L., Nat. Med., 2019, vol. 25, pp. 656–666. https://doi.org/10.1038/s41591-019-0374-x

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  237. Perdicchio, M., Ilarregui, J.M., Verstege, M.I., Cornelissen, L.A.M., Schetters, S.T.T., Engels, S., Ambrosini, M., Kalay, H., Veninga, H., Haan, J.M.M., van Berkel, L.A., Samsom, J.N., Crocke, P.R., Sparwasser, T., Berod, L., Garcia-Vallejo, J.J., van Kooyk, Y., and Unger, W.W.J., Proc. Natl. Acad. Sci. U. S. A., 2016, vol. 113, pp. 3329–3334. https://doi.org/10.1073/pnas.1507706113

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  238. Edgar, L.J., Kawasaki, N., Nycholat, C.M., and Paulson, J.C., Cell Chem. Biol., 2019, vol. 26, pp. 131–136. e4. https://doi.org/10.1016/j.chembiol.2018.10.006

  239. Spence, S., Greene, M.K., Fay, F., Hams, E., Saunders, S.P., Hamid, U., Fitzgerald, M., Beck, J., Bains, B.K., Smyth, P., Themistou, E., Small, D.M., Schmid, D., O’Kane, C.M., Fitzgerald, D.C., Abdelghany, S.M., Johnston, J.A., Fallon, P.G., Burrows, J.F., McAuley, D.F., Kissenpfennig, A., and Scott, C.J., Sci. Transl. Med, 2015, vol. 7, p. 303ra140. https://doi.org/10.1126/scitranslmed.aab3459

    Article  CAS  PubMed  Google Scholar 

  240. Sun, Y., Hong, S., Xie, R., Huang, R., Lei, R., Cheng, B., Sun, D., Du, Y., Nycholat, C.M., Paulson, J.C., and Chen, X., J. Am. Chem. Soc., 2018, vol. 140, pp. 3592–3602. https://doi.org/10.1021/jacs.7b10990

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  241. Dam, T.K., Gerken, T.A., and Brewer, C.F., Biochemistry, 2009, vol. 48, pp. 3822–3827. https://doi.org/10.1021/bi9002919

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  242. Angata, T., Nycholat, C.M., and Macauley, M.S., Trends Pharmacol. Sci., 2015, vol. 36, pp. 645–660. https://doi.org/10.1016/j.tips.2015.06.008

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  243. Büll, C., Heise, T., Adema, G.J., and Boltje, T.J., Trends Biochem. Sci., 2016, vol. 41, pp. 519–531. https://doi.org/10.1016/j.tibs.2016.03.007

    Article  CAS  PubMed  Google Scholar 

  244. Peng, W. and Paulson, J.C., J. Am. Chem. Soc., 2017, vol. 139, pp. 12 450–12 458. https://doi.org/10.1021/jacs.7b03208

    Article  CAS  Google Scholar 

  245. Macauley, M.S., Crocker, P.R., and Paulson, J.C., Nat. Rev. Immunol., 2014, vol. 14, pp. 653–666. https://doi.org/10.1038/nri3737

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  246. Peng, W., de Vries, R.P., Grant, O.C., Thompson, A.J., McBride, R., Tsogtbaatar, B., Lee, P.S., Razi, N., Wilson, I.A., Woods, R.J., and Paulson, J.C., Cell Host Microbe, 2017, vol. 21, pp. 23–34. https://doi.org/10.1016/j.chom.2016.11.004

    Article  CAS  PubMed  Google Scholar 

  247. Schweizer, A., Wohner, M., Prescher, H., Brossmer, R., and Nitschke, L., Eur. J. Immunol., 2012, vol. 42, pp. 2792–2802. https://doi.org/10.1002/eji.201242574

    Article  CAS  PubMed  Google Scholar 

  248. Fesnak, A.D., June, C.H., and Levine, B.L., Nat. Rev. Cancer, 2016, vol. 16, pp. 566–581. https://doi.org/10.1038/nrc.2016.97

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  249. June, C.H., O’Connor, R.S., Kawalekar, O.U., Ghassemi, S., and Milone, M.C., Science, 2018, vol. 359, pp. 1361–1365. https://doi.org/10.1126/science.aar6711

    Article  CAS  PubMed  Google Scholar 

  250. Mehta, R.S. and Rezvani, K., Front. Immunol., 2018, vol. 9, p. 283. https://doi.org/10.3389/fimmu.2018.00283

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  251. Tang, X., Yang, L., Li, Z., Nalin, A.P., Dai, H., Xu, T., Yin, J., You, F., Zhu, M., Shen, W., Chen, G., Zhu, X., Wu, D., and Yu, J., Am. J. Cancer Res., 2018, vol. 8, pp. 1083–1089.

    CAS  PubMed  PubMed Central  Google Scholar 

  252. Matosevic, S., J. Immunol. Res., 2018, vol. 2018, p. 4 054 815. https://doi.org/10.1155/2018/4054815

    Article  CAS  Google Scholar 

  253. Banchereau, J. and Steinman, R.M., Nature, 1998, vol. 392, pp. 245–252. https://doi.org/10.1038/32588

    Article  CAS  PubMed  Google Scholar 

  254. Clausen, B.E. and Stoitzner, P., Front. Immunol., 2015, vol. 6, p. 534. https://doi.org/10.3389/fimmu.2015.00534

    Article  PubMed  PubMed Central  Google Scholar 

  255. Prausnitz, M.R. and Langer, R., Nat. Biotechnol., 2008, vol. 26, pp. 1261–1268. https://doi.org/10.1038/nbt.1504

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  256. Zaric, M., Lyubomska, O., Poux, C., Hanna, M.L., McCrudden, M.T., Malissen, B., Ingram, R.J., Power, U.F., Scott, C.J., Donnelly, R.F., and Kissenpfennig, A., J. Invest. Dermatol., 2015, vol. 135, pp. 425–434. https://doi.org/10.1038/jid.2014.415

    Article  CAS  PubMed  Google Scholar 

  257. Wamhoff, E.-C., Schulze, J., Bellmann, L., Rentzsch, M., Bachem, G., Fuchsberger, F.F., Rademacher, J., Hermann, M., Del Frari, B., van Dalen, R., Hartmann, D., van Sorge, N.M., Seitz, O., Stoitzner, P., and Rademacher, C., ACS Cent. Sci., 2019, vol. 5, pp. 808–820. https://doi.org/10.1021/acscentsci.9b00093

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  258. Schulze, J., Rentzsch, M., Kim, D., Bellmann, L., Stoitzner, P., and Rademacher, C., Biochemistry, 2019, vol. 58, pp. 2576–2580. https://doi.org/10.1021/acs.biochem.9b00402

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  259. Quiocho, F.A., Biochem. Soc. Trans., 1993, vol. 21, pp. 442–448. https://doi.org/10.1042/bst0210442

    Article  CAS  PubMed  Google Scholar 

  260. Schoen, A. and Freire, E., Biochemistry, 1989, vol. 28, pp. 5019–5024. https://doi.org/10.1021/bi00438a017

    Article  CAS  Google Scholar 

  261. Veber, D.F., Johnson, S.R., Cheng, H.-Y., Smith, B.R., Ward, K.W., and Kopple, K.D., J. Med. Chem., 2002, vol. 45, pp. 2615–2623. https://doi.org/10.1021/jm020017n

    Article  CAS  PubMed  Google Scholar 

  262. McClellan, K. and Perry, C.M., Drugs, 2001, vol. 61, pp. 263–283. https://doi.org/10.2165/00003495-200161020-00011

    Article  CAS  PubMed  Google Scholar 

  263. von Itzstein, M., Wu, W.-Y., Kok, G.B., Pegg, M.S., Dyason, J.C., Jin, B., Van Phan, T., Smythe, M.L., White, H.F., Oliver, S.W., Colman, P.M., Varghese, J.N., Ryan, D.M., Woods, J.M., Bethell, R.C., Hotham, V.J., Cameron, J.M., and Penn, C.R., Nature, 1993, vol. 363, pp. 418–423. https://doi.org/10.1038/363418a0

    Article  CAS  PubMed  Google Scholar 

  264. Cox, T., Lachmann, R., Hollak, C., Aerts, J., van Weely, S., Hrebícek, M., Platt, F., Butters, T., Dwek, R., Moyses, C., Gow, I., Elstein, D., and Zimran, A., Lancet, 2000, vol. 355, pp. 1481–1485. https://doi.org/10.1016/S0140-6736(00)02161-9

    Article  CAS  PubMed  Google Scholar 

  265. Chen, X., Zheng, Y., and Shen, Y., Curr. Med. Chem., 2006, vol. 13, pp. 109–116. https://doi.org/10.2174/092986706789803035

    Article  CAS  PubMed  Google Scholar 

  266. Hevey, R. and Ling, C.-C., Future Med. Chem., 2012, vol. 4, pp. 545–584. https://doi.org/10.4155/fmc.11.193

    Article  CAS  PubMed  Google Scholar 

  267. Hevey, R., Pharmaceuticals, 2019, vol. 12, p. 55. https://doi.org/10.3390/ph12020055

    Article  CAS  PubMed Central  Google Scholar 

  268. Oberbillig, T., Mersch, C., Wagner, S., and Hoffmann-Roder, A., Chem. Commun., 2012, vol. 48, pp. 1487–1489. https://doi.org/10.1039/C1CC15139H

    Article  CAS  Google Scholar 

  269. Bull, C., Boltje, T.J., Wassink, M., de Graaf, A.M.A., van Delft, F.L., Brok, M.H., and Adema, G.J., Mol. Cancer Ther, 2013, vol. 12, pp. 1935–1946. https://doi.org/10.1158/1535-7163.MCT-13-0279

    Article  CAS  PubMed  Google Scholar 

  270. Magnani, J.L. and Ernst, B., Discov. Med., 2009, vol. 8, pp. 247–252.

    PubMed  Google Scholar 

  271. Gao, J., Qiao, S., and Whitesides, G.M., J. Med. Chem., 1995, vol. 38, pp. 2292–2301. https://doi.org/10.1021/jm00013a005

    Article  CAS  PubMed  Google Scholar 

  272. Prescher, H., Schweizer, A., Kuhfeldt, E., Nitschke, L., and Brossmer, R., ACS Chem. Biol., 2014, vol. 9, pp. 1444–1450. https://doi.org/10.1021/cb400952v

    Article  CAS  PubMed  Google Scholar 

  273. Prescher, H., Schweizer, A., Kuhfeldt, E., Nitschke, L., and Brossmer, R., ChemBioChem, 2017, vol. 18, pp. 1216–1225. https://doi.org/10.1002/cbic.201600707

    Article  CAS  PubMed  Google Scholar 

  274. Wagner, S., Hauck, D., Hoffmann, M., Sommer, R., Joachim, I., Muller, R., Imberty, A., Varrot, A., and Titz, A., Angew. Chemie Int. Ed. Engl., 2017, vol. 56, pp. 16 559–16 564. https://doi.org/10.1002/anie.201709368

    Article  CAS  Google Scholar 

  275. Ordanini, S., Varga, N., Porkolab, V., Thepaut, M., Belvisi, L., Bertaglia, A., Palmioli, A., Berzi, A., Trabattoni, D., Clerici, M., Fieschi, F., and Bernardi, A., Chem. Commun., 2015, vol. 51, pp. 3816–3819. https://doi.org/10.1039/C4CC09709B

    Article  CAS  Google Scholar 

  276. Berzi, A., Ordanini, S., Joosten, B., Trabattoni, D., Cambi, A., Bernardi, A., and Clerici, M., Sci. Rep., vol. 6, p. 35 373. https://doi.org/10.1038/srep35373

  277. Berry, G.T., in GeneReviews®, Adam, M.P., Ardinger, H.H., and Pagon, R.A., Eds., Seattle (WA), 1993.

    Google Scholar 

  278. Yamamoto, T., Harada-Shiba, M., Nakatani, M., Wada, S., Yasuhara, H., Narukawa, K., Sasaki, K., Shibata, M.-A., Torigoe, H., Yamaoka, T., Imanishi, T., and Obika, S., Mol. Ther. Nucleic Acids, 2012, vol. 1, p. e22. https://doi.org/10.1038/mtna.2012.16

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  279. Keppler, D., Lesch, R., Reutter, W., and Decker, K., Exp. Mol. Pathol., 1968, vol. 9, pp. 279–290. https://doi.org/10.1016/0014-4800(68)90042-7

    Article  CAS  PubMed  Google Scholar 

  280. Pearce, A.K. and O’Reilly, R.K., Bioconjug. Chem., 2019, vol. 30, pp. 2300–2311. https://doi.org/10.1021/acs.bioconjchem.9b00456

    Article  CAS  PubMed  Google Scholar 

  281. Komarova, B.S., Tsvetkov, Y.E., and Nifantiev, N.E., Chem. Rec., 2016, vol. 16, pp. 488–506. https://doi.org/10.1002/tcr.201500245

    Article  CAS  PubMed  Google Scholar 

  282. Krylov, V.B., Argunov, D.A., Vinnitskiy, D.Z., Verkhnyatskaya, S.A., Gerbst, A.G., Ustyuzhanina, N.E., Dmitrenok, A.S., Huebner, J., Holst, O., Siebert, H.-C., and Nifantiev, N.E., Chemistry, 2014, vol. 20, pp. 16 516–16 522. https://doi.org/10.1002/chem.201405083

    Article  CAS  Google Scholar 

  283. Tokatly, A.I., Vinnitskiy, D.Z., Ustuzhanina, N.E., and Nifantiev, N.E., Russ. J. Bioorg. Chem., 2021, vol. 47, pp. 52–68.

    Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors would like to thank corresponding member of RAS N.E. Nifantiev (N.D. Zelinsky Institute of organic chemistry RAS) for valuable comments and discussion.

Funding

This work was supported by the Russian Scientific Foundation (project no. 19-13-00158).

Author information

Authors and Affiliations

  1. Lobachevsky Nizhny Novgorod State University, 603950, Nizhny Novgorod, Russia

    E. S. Shchegravina, A. A. Sachkova, S. D. Usova, A. V. Nyuchev, Yu. A. Gracheva & A. Yu. Fedorov

Authors
  1. E. S. Shchegravina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. A. Sachkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. D. Usova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. V. Nyuchev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yu. A. Gracheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. Yu. Fedorov
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

The article was translated by the authors.

Corresponding author

Correspondence to A. Yu. Fedorov.

Ethics declarations

COMPLIANCE WITH ETHICAL STANDARDS

This publication does not contain any research description with the participation of humans or animals as research objects.

CONFLICT OF INTERESTS

The authors declare no conflict of interests.

Additional information

Abbreviations: ASGPR, asialoglycoprotein receptor; ASO, antisense oligonucleotide; CAR-T, chimeric antigen receptor T cells; GalNAc, N-acetyl-D-galactosamine; HA, hyaluronic acid; MSC, mesenchymal stem cells; K, natural killers; ON, oligonucleotide; siRNA, small interference RNA; sLeX and sLeA, isomeric tetrasaccharides Sialyl Lewis X and Sialyl Lewis A; LC, Langerhans cell; PEG, poly(ethylene) glycol; PDT, photodynamic therapy.

Supplementary Information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shchegravina, E.S., Sachkova, A.A., Usova, S.D. et al. Carbohydrate Systems in Targeted Drug Delivery: Expectation and Reality. Russ J Bioorg Chem 47, 71–98 (2021). https://doi.org/10.1134/S1068162021010222

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162021010222

Keywords:

Search

Navigation