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Folic acid and its derivatives for targeted photodynamic therapy of cancer

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Russian Chemical Bulletin Aims and scope

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Abstract

The fundamentals of folic acid and folate receptors functioning in the body, changes in the expression level of folate receptors in carcinogenesis, as well as use of folic acid and its derivatives for targeted delivery of photosensitizers to tumors have been reviewed. The ways of increasing the efficacy of photodynamic therapy by creating multifunctional nanoplatforms that ensure both passive targeting and receptor-mediated internalization of photosensitizers in tumor cells have been discussed.

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References

  1. W. Herrmann, R. Obeid, Vitamins in the Prevention of Human Diseases, Eds W. Herrmann, R. Obeid, Walter de Gruyter GmbH, Berlin, 2011.

  2. C. Marchetti, I. Palaia, M. Giorgini, C. De Medici, R. Iada-rola, L. Vertechy, L. Domenici, V. Di Donato, L. Tomao, F. Muzii, P. B. Panici, Onco Targets Ther., 2014, 7, 1223.

    Article  CAS  Google Scholar 

  3. L. Wills, Brit. Med. J., 1931, 1, 1059.

    Article  CAS  Google Scholar 

  4. H. K. Mitchell, E. E. Snell, R. J. Williams, J. Am. Chem. Soc., 1941, 63, 2284.

    Article  CAS  Google Scholar 

  5. J. Carroll Temple, J. D. Rose, A. John, J. Org. Chem., 1981, 46, 3666.

    Article  Google Scholar 

  6. M. M. Araújo, E. Marchioni, M. Bergaentzle, M. Zhao, F. Kuntz, E. Hahn, A. L. C. H. Villavicencio, J. Agr. Food Chem., 2011, 59, 1244.

    Article  Google Scholar 

  7. C. Müller, Molecules, 2013, 18, 5005.

    Article  Google Scholar 

  8. J. A. Ledermann, S. Canevari, Ann. Oncology, 2015, 26, 2034.

    Article  CAS  Google Scholar 

  9. R. Ravi, Z. Zhiquan, M. C. Lynn, D. Mary, S. J. Benkovic, G. Hammes, Proc. Natl. Acad. Sci. USA, 2002, 99, 13481.

    Article  Google Scholar 

  10. D. S. Goodsell, The Oncologist, 1999, 4(4), 340.

    CAS  Google Scholar 

  11. F. Shen, J. F. Ross, X. Wang, M. Ratnam, Biochemistry, 1994, 33, 1209.

    Article  CAS  Google Scholar 

  12. X. Wang, F. Shen, J. H. Freisheim, L. E. Gentry, M. Ratnam, Biochem. Pharmacol., 1992, 44, 1898.

    Article  CAS  Google Scholar 

  13. F. Shen, M. Wu, J. F. Ross, D. Miller, M. Ratnam, Bio-chemistry, 1995, 33, 5660.

    Google Scholar 

  14. J. F. Ross, P. K. Chaudhuri, M. Ratnam, Cancer, 1994, 73, 2432.

    Article  CAS  Google Scholar 

  15. G. Toffoli, C. Cernigoi, A. Russo, A. Gallo, M. Bagnoli, M. Boiocchi, Int. J. Cancer., 1997, 74, 193.

    Article  CAS  Google Scholar 

  16. C. P. Leamon, P. S. Low, Proc. Natl. Acad. Sci. USA, 1991, 88, 5572.

    Article  CAS  Google Scholar 

  17. C. Chen, J. Ke, X. E. Zhou, W. Yi, J. S. Brunzelle, J. Li, E. Yong, H. E. Xu, K. Melcher, Nature, 2013, 500, 486.

    Article  CAS  Google Scholar 

  18. Y. Lu, P. S. Low, Adv. Drug Delivery Revs, 2002, 54, 675.

    Article  CAS  Google Scholar 

  19. V. I. Chissov, V. V. Sokolov, E. V. Filonenko, Ross. Khim. Zh., 1998, 5, 5 [Mendeleev Chem. J. (Engl. Transl.), 1998, 5].

    Google Scholar 

  20. E. F. Stranadko, Fotodinamicheskaya terapiya i fotodiagnostika [PDT and Photodyagnostics], 2015, 1, 3 (in Russian).

    Google Scholar 

  21. Order of the Ministry of Health of the Russian Federated No. 915n dt 15.11.2012 "On the Approval of the Procedure for Provision of Medical Care on the Oncology Profile" (with amendments and appendices dt 23.08.2016) (in Russian).

  22. B. Roeder, Lasers in Med. Sci., 1990, 5, 99.

    Article  Google Scholar 

  23. S. Singh, A. Aggawall, D. K. Bhupathiraju, G. Arianna, K. Tiwari, C. M. Drain, Chem. Rev., 2015, 115, 10261.

    Article  CAS  Google Scholar 

  24. M. A. Grin, A. F. Mironov, A. A. Shtil, Anti-Cancer Agents Med. Chem., 2008, 8, 683.

    Article  CAS  Google Scholar 

  25. F. Bryden, R. W. Boyle, Adv. Inorg. Chem., 2016, 68, 141.

    Article  CAS  Google Scholar 

  26. Pat. RF 2128993; Buyll. Izobret, 1999 (in Russian).

    Google Scholar 

  27. Pat. RF 2353624; Buyll. Izobret, 2009 (in Russian).

    Google Scholar 

  28. R. I. Yakubovskaya, N. I. Kazachkina, T. A. Karmakova, L. A. Shitova, E. V. Pecherskikh, G. I. Fomina, E. R. Nemtsova, V. M. Derkacheva, A. F. Feofanov, V. I. Chissov, Ross. Khim. Zh., 1998, 5, 17 [Mendeleev Chem. J. (Engl. Transl.), 1998, 5].

    Google Scholar 

  29. S. M. Hillier, K. P. Maresca, F. J. Femia, J. C. Marquis, C. A. Foss, N. Nguyen, C. N. Zimmerman, J. A. Barret, W. C. Eckelman, M. G. Pomper, J. L. Joyal, J. W. Babich, Cancer Res., 2009, 69, 6932.

    Article  CAS  Google Scholar 

  30. M. Ginj, Proc. Natl. Acad. Sci. USA, 2006, 103, 16436.

    Article  CAS  Google Scholar 

  31. D. Neri, C. T. Supuran, Nat. Rev. Drug Discov., 2011, 10, 767.

    Article  CAS  Google Scholar 

  32. M. Wirth, L. Manka, P. Hammerer, Eur. Urology Supple-ments, 2014, 139.

    Google Scholar 

  33. M. Camerin, M. Magaraggia, M. Soncin, G. Jori, M. Mo-reno, J. Cook, D. A. Russell, Eur. J. Cancer, 2010, 1910.

    Google Scholar 

  34. R. Schneider, F. Schmitt, C. Frochot, Y. Fort, N. Lourette, F. Guillemin, J. Muller, M. Barberi-Heyob, Bioorg. Med. Chem., 2005, 13, 2799.

    Article  CAS  Google Scholar 

  35. H. Azais, C. Schmitt, M. Tardivel, O. Kerdraon, A. Stalli-vieri, C. Frochot, N. Betrouni, P. Collinet, S. Mordon, Photodiagnosis and Photodynamic Therapy, 2016, 13, 130.

    Article  CAS  Google Scholar 

  36. S. M. F. Hahn, M. E. Putt, J. Metz, D. B. Shin, E. Rickter, C. Menon, Clin. Cancer Res. J. Am. Assoc. Cancer Res., 2006, 12, 5464.

    Article  CAS  Google Scholar 

  37. P. Li, J. H. Mu, H. L. Xiao, D. H. Li, Oncology Reports, 2015, 33, 125.

    Article  Google Scholar 

  38. J. Gravier, R. Schneider, C. Frochot, T. Bastogne, F. Schmitt, J. Didelon, F. Guillemin, M. Barberi-Heyob, J. Med. Chem., 2008, 51, 3867.

    Article  CAS  Google Scholar 

  39. A. Stallivieri, L. Colombeau, G. Jetpisbayeva, A. Moussaron, B. Myrzakhmetov, P. Arnoux, S. Acherar, R. Vanderesse, C. Frochot, Bioorg. Med. Chem., 2017, 25, 1.

    Article  CAS  Google Scholar 

  40. H. You, H. E. Yoon, P. H. Jeong, H. Ko, J. H. Yoon, Y. C. Kim, Bioorg. Med. Chem., 2015, 23, 1453.

    Article  CAS  Google Scholar 

  41. S. M. Lee, Y. D. Ahn, H. Mun, B. Goh, T. Y. Kim, J. Seo, M. G. Kim, Bull. Korean Chem. Soc., 2016, 37, 2036.

    Article  CAS  Google Scholar 

  42. L. B. Josefsen, R. W. Boyle, Br. J. Pharmacol., 2008, 154, 1.

    Article  CAS  Google Scholar 

  43. R. D. Haynes, R. J. Meagher, J. I. Won, F. M. Bogdan, A. E. Barron, Bioconjug. Chem., 2005, 16, 929.

    Article  CAS  Google Scholar 

  44. S. M. Miller, R. J. Simon, S. Ng, R. N. Zuckermann, J. M. Kerr, W. H. Moos, Bioorg. Med. Chem. Lett., 1994, 4, 2657.

    Article  CAS  Google Scholar 

  45. Y. Li, J. Wang, X. Zhang, W. Guo, F. Li, M. Yu, X. Kong, W. Wu, Z. Hong, Org. Biomol. Chem., 2015, 13, 7681.

    Article  CAS  Google Scholar 

  46. G. Nkepang, M. Bio, P. Rajaputra, S. G. Awuah, Y. You, Bioconjugate Chem., 2014, 25, 2175.

    Article  CAS  Google Scholar 

  47. M. Bio, G. Nkepang, Y. You, Chem. Commun., 2012, 48, 6517.

    Article  CAS  Google Scholar 

  48. G. Nkepang, P. K. Pogula, M. Bio, Y. You, Photochem. Photobiol., 2012, 88, 753.

    Article  CAS  Google Scholar 

  49. M. Bio, P. G. Rajaputra, P. G. Nkepang, G. S. G. Awuah, A. M. Hossion, Y. You, J. Med. Chem., 2013, 56, 3936.

    Article  CAS  Google Scholar 

  50. A. Guaragna, G. N. Roviello, S. DÉrrico, C. Paolella, G. Palumbo, D. DÁlonzo, Tetrahedron Lett., 2015, 56, 775.

    Article  CAS  Google Scholar 

  51. M. Ranjita, S. Acharya, S. K. Sahoo, Drug Discovery Today, 2010, 15, 842.

    Article  Google Scholar 

  52. X. Wang, L. Yang, Z. Chen, D. M. Shin, CA Cancer J. Clin., 2008, 58, 97.

    Article  Google Scholar 

  53. J. Y. Kim, O. Voznyy, D. Zhitomirsky, E. H. Sargent, Adv. Mater., 2013, 25, 4986.

    Article  CAS  Google Scholar 

  54. N. S. Makarov, P. C. Lau, C. Olson, K. A. Velizhanin, K. M. Solntsev, K. Kieu, S. Kilina, S. Tretiak, R. A. Norwood, N. Peyghambarian, J. W. Perry, ACS Nano, 2014, 8, 12572.

    Article  CAS  Google Scholar 

  55. M. Zhao, H. Zhang, Y. Li, A. Ashok, R. Liang, W. Zhou, L. Peng, Biomedical Optics Express, 2014, 5, 1296.

    Article  Google Scholar 

  56. J. D. Bhawalkar, N. D. Kumar, C. F. Zhao, P. N. Prasad, J. Clin. Laser Med. Surg., 1997, 15, 201.

    CAS  Google Scholar 

  57. D. Nicholas, C. Fowley, A. P. McHale, S. Kamila, J. Sheng, J. Atchison, J. F. Callan, Colloid. Nanoparticles for Biomedi-cal Applications, 2015, 10, 933.

    Google Scholar 

  58. H. Homayoni, W. Chen, Proc. of Bioengineering Conf. (NEBEC), Boston, USA, 25—27 April 2014.

    Google Scholar 

  59. X. Shen, S. Li, L. Li, S. Q. Yao, Q. H. Xu, Chem. Eur. J., 2014, 20, 1.

    Article  Google Scholar 

  60. X. Q. Shen, L. Li, A. C. M. Chan, S. Q. Yao, Q.-H. Xu, Adv. Opt. Mater., 2013, 1, 92.

    Article  Google Scholar 

  61. L. V. Nair, S. S. Nazeer, R. S. Jayasree, A. Ajayaghosh, ACS Nano, 2015, 9, 5825.

    Article  CAS  Google Scholar 

  62. W. P. Savarimuthu, P. Gananathan, A. P. Rao, E. Mani-ckam, G. Singaravelu, J. Nanosci. Nanotechnol., 2015, 15, 5577.

    Article  CAS  Google Scholar 

  63. L. Zhao, T. H. Kim, J. C. Ahn, H. W. Kim, S. Y. Kim, J. Mater. Chem. B, 2013, 1, 5806.

    Article  CAS  Google Scholar 

  64. B. C. Mei, K. Susumu, I. L. Medintz, H. Mattoussil, Nat. Protoc., 2009, 4, 412.

    Article  CAS  Google Scholar 

  65. K. Haume, S. Rosa, S. Grellet, M. A. S’mia ek, K. T. Butterworth, A. V. Solovýov, K. M. Prise, J. Golding, N. J. Mason, Cancer Nanotechnol., 2016, 7, 8.

    Article  Google Scholar 

  66. M. Gary-Bobo, V. Mir, C. Rouxel, D. Brevet, O. Hocine, M. Maynadier, A. Gallud, A. Silva, O. Mongin, L. Blan-chard-Desce, S. Richeter, B. Loock, P. Maillard, A. Morere, M. Garcia, L. Raehm, J. Durand, Int. J. Pharm., 2012, 432, 99.

    Article  CAS  Google Scholar 

  67. I. Teng, Y. Chang, L. Wang, H. Lu, L. Wu, C. M. Yang, C. Chiu, C. H. Yang, S. Hsu, J. Ho, Biomaterials, 2013, 34, 7462.

    Article  CAS  Google Scholar 

  68. X. Tan, X. Pang, M. Lei, M. Ma, F. Guo, J. Wang, M. Yu, Int. J. Pharm., 2016, 503, 220.

    Article  CAS  Google Scholar 

  69. I. V. Pantyushenko, M. A. Grin, R. I. Yakubovskaya, E. A. Plotnikova, N. B. Morozova, A. A. Tsygankov, A. F. Miro-nov, Vestn. MITKhT [Bulletin of the Moscow State University of Fine Chemical Technologies], 2014, 9, 3 (in Russian).

    CAS  Google Scholar 

  70. M. A. Grin, R. I. Reshetnikov, R. I. Yakubovskaya, E. A. Plotnikova, N. B. Morozova, A. A. Tsigankov, A. V. Efre-menko, D. E. Ermakova, A. V. Feofanov, A. F. Mironov, J. Porphyrins Phthalocyanines, 2014, 18, 129.

    Article  CAS  Google Scholar 

  71. M. A. Grin, P. V. Toukach, V. B. Tsvetkov, R. I. Reshetnikov, O. V. Kharitonova, A. S. Kozlov, A. A. Krasnovsky Jr., A. F. Mironov, Dyes and Pigments, 2015, 121, 21.

    Article  CAS  Google Scholar 

  72. I. S. Lonin, L. M. Likhosherstov, O. S. Novikova, A. D. Plyutinskaya, E. A. Plotnikova, V. V. Kachala, R. I. Yaku-bovskaya, A. F. Mironov, J. Porphyrins Phthalocyanines, 2012, 16, 1094.

    Article  Google Scholar 

  73. N. V. Suvorov, M. A. Grin, M. Popkov, A. S. Garanina, A. F. Mironov, A. G. Majouga, Macroheterocycles, 2016, 9, 175.

    Article  CAS  Google Scholar 

  74. I. V. Pantyushenko, P. G. Rudakovskaya, A. V. Starovoitova, A. A. Mikhailovskaya, M. A. Abakumov, M. A. Kaplan, A. A. Tsygankov, A. G. Mazhuga, M. A. Grin, A. F. Mironov, Biokhimiya, 2015, 80, 891 [Biochemistry (Moscow) (Engl. Transl.), 2015, 80].

    Google Scholar 

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Authors and Affiliations

  1. Moscow Technological University, Institute of Fine Chemical Technologies, 86 prosp. Vernadskogo, 119571, Moscow, Russian Federation

    N. V. Suvorov, A. F. Mironov & M. A. Grin

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  1. N. V. Suvorov
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  2. A. F. Mironov
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  3. M. A. Grin
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Correspondence to M. A. Grin.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1982—2008, November, 2017.

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Suvorov, N.V., Mironov, A.F. & Grin, M.A. Folic acid and its derivatives for targeted photodynamic therapy of cancer. Russ Chem Bull 66, 1982–2008 (2017). https://doi.org/10.1007/s11172-017-1973-7

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