Abstract
Nature-derived cyclopeptides, a large group of secondary metabolites, are ubiquitously present in nature. Compared to the linear counterparts, cyclopeptides possess structural rigidity, biochemical stability, binding affinity and membrane permeability. Mechanistically, nature-derived cyclopeptides could interfere with various signaling pathways to induce cancer cell death and demonstrated potential in vitro and in vivo efficacy against various cancers including multidrug-resistant forms. Hence, nature-derived cyclopeptides are propitious lead compounds/candidates for developing novel anticancer therapeutic agents. This review attempts to provide a comprehensive summary of the sources, structural diversity, anticancer potential, and mechanisms of action of nature-derived cyclopeptides, covering articles published from 2018 to present.
REFERENCES
Hulvat, M.C., Surg. Clin. N. Am., 2020, vol. 100, p. 469. https://doi.org/10.1016/j.suc.2020.01.002
Siegel, R.L., Miller, K.D., Wagle, N. S., and Jemal, A., CA Cancer J. Clin., 2023, vol. 73, p. 17. https://doi.org/10.3322/caac.21763
Miller, K.D., Nogueira, L., Devasia, T., Mariotto, A.B., Yabroff, K.R., Jemal, A., Kramer, J., and Siegel, R.L., CA Cancer J. Clin., 2022, vol. 72, p. 409. https://doi.org/10.3322/caac.21731
Thakur, G., Kumar, R., Kim, S.B., Lee, S.Y., Lee, S.L., and Rho, G.J., Biomed., 2021, vol. 9, p. e178. https://doi.org/10.3390/biomedicines9020178
Fan, J., To, K.K.W., Chen, Z.S., and Fu, L., Drug Resist. Updates, 2023, vol. 66, p. e100905. https://doi.org/10.1016/j.drup.2022.100905
Emran, T.B., Shahriar, A., Mahmud, A.R., Rahman, T., Abir, M.H., Siddiquee, M.F.R., Ahmed, H., Islam, A., and Hassan, M.M., Front. Oncol., 2022, vol. 12, p. e 891652. https://doi.org/10.3389/fonc.2022.891652
International Agency for Research on Cancer. Cancer Tomorrow. https://gco.iarc.fr/tomorrow/graphic-isotype?type=0&population=900&mode=population&sex=0&cancer=39&age_group=value&apc_male=0&apc_female=0
Daly, N.L. and Wilson, D.T., Biochem. Soc. Trans., 2021, vol. 49, p. 1279. https://doi.org/10.1042/BST20200881
Chia, L.Y., Kumar, P.V., Maki, M.A.A., Ravichandran, G., and Thilagar, S., Int. J. Pept. Res. Ther., 2023, vol. 29, p. e7. https://doi.org/10.1007/s10989-022-10478-y
Ribeiro, R., Pinto, E., Fernandes, C., and Sousa, E., Mar. Drugs, 2022, vol. 20, p. e397. https://doi.org/10.3390/md20060397
Saharan, R., Kumar, S., Khokra, S.L., Singh, S., Tiwari, A., Tiwari, V., Sahoo, B.M., and Kumar, M.A., Curr. Nutr. Food Sci., 2022, vol. 18, p. 441. https://doi.org/10.2174/1573401318666220114153509
Ramadhani, D., Maharani, R., Gazzali, A.M., and Muchtaridi, M., Molecules, 2022, vol. 27, p. e4428. https://doi.org/10.3390/molecules27144428
Yang, Y., Mao, H., Chen, L., and Li, L., Arch. Biochem. Biophys., 2021, vol. 701, p. e108776. https://doi.org/10.1016/j.abb.2021.108776
Li, C.M., Haratipour, P., Lingeman, R.G., Perry, J.J.P., Gu, L., Hickey, R.J., and Malkas, L.H., Cells, 2021, vol. 10, p. e2908. https://doi.org/10.3390/cells10112908
Zhang, Q.T., Liu, Z.D., Wang, Z., Wang, T., Wang, N., Wang, N., Zhang, B., and Zhao, Y.F., Mar. Drugs, 2021, vol. 19, p. e115. https://doi.org/10.3390/md19020115
Mehta, L., Dhankhar, R., Gulati, P., Kapoor, R.K., Mohanty, A., and Kumar, S., J. Pep. Sci., 2020, vol. 26, p. e3246. https://doi.org/10.1002/psc.3246
Zhang, J.N., Xia, Y.X., and Zhang, H.J., Int. J. Mol. Sci., 2021, vol. 22, p. e3973. https://doi.org/10.3390/ijms22083973
Aaghaz, S., Gohel, V., and Kamal, A., Curr. Top. Med. Chem., 2019, vol. 19, p. 1491. https://doi.org/10.2174/1568026619666190125161517
Abdalla, M.A., and McGaw, L.J., Molecules, 2018, vol. 23, p. e2080. https://doi.org/10.3390/molecules23082080
Zhang, H. and Chen, S., RSC Chem. Biol., 2022, vol. 3, p. 18. https://doi.org/10.1039/d1cb00154j
Du, X., Xiao, S., Luo, Q., Liu, X., and Liu, J., J. Pep. Sci., 2022, vol. 28, p. E3385. https://doi.org/10.1002/psc.3385
Liu, J., Liu, F., Liu, P., Xu, H., Tang, L., Han, X., Zheng, M., and Ren, Y., J. Pep. Sci., 2022, vol. 28, p. E3410. https://doi.org/10.1002/psc.3410
Li, W., Liu, J., Liu, X., Wang, F., and Zhao, H., Phytochem. Lett., 2020, vol. 40, p. 156. https://doi.org/10.1016/j.phytol.2020.09.015
Liu, Z., Fu, J., Xiao, S., and Wang, D., RSC Adv., 2019, vol. 9, p. 29847. https://doi.org/10.1039/D2RA90037H
Ahn, M.Y., Oncol. Lett., 2018, vol. 16, p. 6552. https://doi.org/10.3892/ol.2018.9468
Lomchoey, N., Panseeta, P., Boonsri, P., Apiratikul, N., Prabpai, S., Kongsaeree, P., and Suksamrarn, S., RSC Adv., 2018, vol. 8, p. 18204. https://doi.org/10.1039/C7RA13050C
Bitchi, M.B., Magid, A.A., Kabran, F.A., Yao-Kouassi, P.A., Harakat, D., Morjani, H., Tonzibo, F.Z., and Voutquenne-Nazabadioko, L., Phytochem., 2019, vol. 167, p. e112081. https://doi.org/10.1016/j.phytochem.2019.112081
Kwon, Y., Byun, W.S., Kim, B.Y., Song, M.C., Bae, M., Yoon, Y.J., Shin, J., Lee, S.K., and Oh, D.C., Molecules, 2018, vol. 23, p. e1266. https://doi.org/10.3390/molecules23061266
Ahmad, R., Aldholmi, M., Carlsson, H., CarreteroMolina, D., Field, R.A., Ganesan, A., Gefflaut, T., Reyes, F., and Wilkinson, B., Angew. Chem. Int. Ed., 2022, vol. 61, p. E202203175. https://doi.org/10.1002/anie.202203175
Le, T.C., Pulat, S., Lee, J., Kim, G.J., Kim, H., Lee, E.Y., Hillman, P.F., Nam, S.J., and Fenical, W., ACS Omega, 2022, vol. 7, p. 1722. https://doi.org/10.1021/acsomega.1c04520
Ibrahim, A.H., Attia, E.Z., Hajjar, D., Anany, M.A., Desoukey, S.Y., Fouad, M.A., Kamel, M.S., Wajant, H., Gulder, T.A.M., and Abdelmohsen, U.R., Mar. Drugs, 2018, vol. 16, p. e290. https://doi.org/10.3390/md16090290
Qin, F., Wang, C.Y., Kim, D., Wang, H.S., Zhu, Y.K., Lee, S.K., Yao, G.Y., and Liang, D., J. Org. Chem., 2021, vol. 82, p. 1462. https://doi.org/10.1021/acs.joc.0c02057
Almaliti, J., Canuto, K.M., Duggan, B.M., Gerwick, W.H., Glukhov, E., Keller, L., Koehnke, J., Sikandar, A., and Suzuki, B.M., ACS Chem. Biol., 2020, vol. 15, p. 751. https://doi.org/10.1021/acschembio.9b00992
Wen, J., Liu, Y., Zhang, S.S., Song, Y., Li, W.L., and Yan, X.J., J. Asian Nat. Prod. Res., 2022, vol. 24, p. 1169. https://doi.org/10.1080/10286020.2022.2083607
Cho, Y.B., Han, J.S., Hong, J.T., Hwang, B.Y., Kim, J.G., Lee, D., Lee, J.W., Lee, M.K., Lee, Y.J., and Shin, D.H., Molecules, 2021, vol. 26, p. e7275. https://doi.org/10.3390/molecules26237275
Nair, V., Kim, M.C., Golen, J.A., Rheingold, A.L., Castro, G.A., Jensen, P.R., and Fenical, W., Mar. Drugs, 2020, vol. 18, p. e549. https://doi.org/10.3390/md18110549
Wu, C., Tang, J., Malit, J.J.L., Wang, R., Sung, H.H.Y., Williams, I.D., and Qian, P.Y., J. Nat. Prod., 2022, vol. 85, p. 1751. https://doi.org/10.1021/acs.jnatprod.2c00290
Ise, Y., Matsunaga, S., Ohtsuka, S., Okada, S., Takada, K., and Tian, T., Tetrahedron, 2020, vol. 76, p. e130997. https://doi.org/10.1016/j.tet.2020.130997
Abdel-Wahab, N.M., Harwoko, H., Müller, W.E.G., Hamacher, A., Kassack, M.U., Fouad, M.A., Kamel, M.S., Liu, Z., and Proksch, P., Bioorg. Med. Chem., 2019, vol. 27, p. 3954. https://doi.org/10.1016/j.bmc.2019.07.025
Anand, M., Alagar, M., Ranjitha, J., and Selvaraj, V., Arab. J. Chem., 2019, vol. 12, p. 2782. https://doi.org/10.1016/j.arabjc.2014.05.037
Choules, M.P., Wolf, N.M., Lee, H., Anderson, J.R., Grzelak, E.M., Wang, Y., Ma, R., Franzblau, S.G., and Cho, S., Antimicrob. Agents Chemother., 2019, vol. 63, p. E02204-18. https://doi.org/10.1128/AAC.02204-18
Chen, Y.X., Liu, C., Liu, N., Wu, Y., Zhao, Q.J., Hu, H.G., Li, X., and Zou, Y., Chem. Biodiversity, 2018, vol. 15, p. E1700414. https://doi.org/10.1002/cbdv.201700414
Chen, W., Chen, Y., Liu, Y., Long, J., Wang, J., Yang, B., and Zhou, X., Mar. Drugs, 2021, vol. 19, p. e701. https://doi.org/10.3390/md19120701
Yan, X.J., Wen, J., Song, Y., Sha, D.M., Sha, M.L.N., Zhang, S.S., and Liu, Y., Chin. J. Chin. Mat. Med., 2022, vol. 47, p. 4391. https://doi.org/10.19540/j.cnki.cjcmm.20220421.204
Sosa-Rueda, J., Domínguez-Meléndez, V., Ortiz-Celiseo, A., López-Fentanes, F.C., Cuadrado, C., Fernández, J.J., Daranas, A.H., and Cen-Pacheco, F., Phytochem., 2022, vol. 194, p. e112839. https://doi.org/10.1016/j.phytochem.2021.112839
Rodríguez-Expósito, R.L., Sosa-Rueda, J., Reyes-Batlle, M., Sifaoui, I., Cen-Pacheco, F., Daranas, A.H., Díaz-Marrero, A.R., Piñero, J.E., Fernández, J.J., and Lorenzo-Morales, J. Int. J. Parasitol.: Drugs Drug Resist., 2021, vol. 17, p. 67. https://doi.org/10.1016/j.ijpddr.2021.08.003
Kim, E., Shin, Y.H., Kim, T.H., Byun, W.S., Cui, J., Du, Y.E., Lim, H.J., Oh, D.C., and Yoon, Y.J., Biomol., 2019, vol. 9, p. e672. https://doi.org/10.3390/biom9110672
Byun, W.S., Kim, S., Kim, W.K., Lee, S.K., Oh, D.C., and Shin, Y.H., J. Nat. Prod., 2020, vol. 83, p. 118. https://doi.org/10.1021/acs.jnatprod.9b00918
Cai, W., Matthew, S., Chen, Q.Y., Paul, V.J., and Luesch, H., Bioorg. Med. Chem., 2018, vol. 26, p. 2310. https://doi.org/10.1016/j.bmc.2018.03.022
Bornancin, L., Alonso, E., Alvariño, R., Inguimbert, N., Bonnard, I., Botana, L.M., and Banaigs, B., Bioorg. Med. Chem., 2019, vol. 27, p. 1966. https://doi.org/10.1016/j.bmc.2019.03.046
Sullivan, P., Krunic, A., Burdette, J.E., and Orjala, J., J. Antibiot., 2020, vol. 73, p. 526. https://doi.org/10.1038/s41429-020-0301-x
Kwon, O.S., Kim, C.K., Byun, W.S., Oh, J., Lee, Y.J., Lee, H.S., Sim, C.J., Oh, K.B., and Shin, J., J. Nat. Prod., 2018, vol. 81, p. 1426. https://doi.org/10.1021/acs.jnatprod.8b00121
Liu, X.D., Gu, K.B., Xia, S.S., Zhang, D.J., and Li, Y.G., J. Antibiot., 2018, vol. 71, p. 838. https://doi.org/10.1038/s41429-018-0071-x
Hu, Y.Y., Feng, L., Wang, J., Zhang, X.J., Wang, Z., and Tan, N.H., Chem. Biodiversity, 2019, vol. 16, p. E1800438. https://doi.org/10.1002/cbdv.201800438
Yang, J., Yang, T., Yan, W., Li, D., Wang, F., Wang, Z., Guo, Y., Bai, P., Tan, N., and Chen, L., RSC Adv., 2018, vol. 8, p. 23451. https://doi.org/10.1039/c8ra04241a
Wang, Z., Zhao, S., Song, L., Pu, Y., Wang, Q., Zeng, G., Liu, X., Bai, M., Li, S., Gao, F., Chen, L., Wang, C., and Tan, N., Cell Death Dis., 2018, vol. 9, p. e715. https://doi.org/10.1038/s41419-018-0743-2
Feng, L., Li, L., Tan, N.H., Wang, J., Wang, J., Wang, Y.R., and Wang, Z., J. Ethnopharm., 2021, vol. 266, p. e113438. https://doi.org/10.1016/j.jep.2020.113438
Xu, X., Jiang, N., Liu, S., Jin, Y., Cheng, Y., Xu, T., Wang, X., Fan, J., and Zhang, A., J. Nat. Prod., 2022, vol. 85, p. 1918. https://doi.org/10.1021/acs.jnatprod.1c01215
Sugawara, K., Kanki, D., Watanabe, R., Matsushima, R., Ise, Y., Yokose, H., Morii, Y., Okada, S., and Matsunaga, S., Tetrahedron, 2022, vol. 119, p. e132859. https://doi.org/10.1016/j.tet.2022.132859
Li, C., Hu, Y., Wu, X., Stumpf, S.D., Qi, Y., D’Alessandro, J.M., Nepal, K.K., Sarotti, A.M., Cao, S., and Blodgett, J.A.V., PNAS, 2022, vol. 119, p. e2117941119. https://doi.org/10.1073/pnas.2117941119
Funding
This work was supported by ongoing institutional funding. No additional grants to carry out or direct thisparticular research were obtained.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
No conflict of interest was declared by the authors.
Additional information
Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Liu, Bs., Liu, K., Wang, J. et al. The Current Scenario of Nature-Derived Cyclopeptides with Anticancer Potential (A Review). Russ J Gen Chem 94, 675–689 (2024). https://doi.org/10.1134/S1070363224030198
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363224030198