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Amphiphilic copolymers of N-vinylpyrrolidone with (di)methacrylates as promising carriers for the platinum(IV) complex with antitumor activity

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Abstract

Water-soluble polymer compositions of the lipophilic complex of cis-bis[(nitroxyethyl)-isonicotinamide-N]-tetrachloroplatinum(iv) with antitumor activity were prepared. The complex was solubilized by amphiphilic copolymers of N-vinylpyrrolidone (VP) with (di)methacrylates synthesized by radical copolymerization in toluene in the absence of any inhibitors of polymer chain growth. Aqueous buffer solutions of the nanostructures were studied by dynamic light scattering, and the influence of the concentrations of the complex and copolymer and temperature on the nanoparticle size (hydrodynamic radius) was estimated. The nanostructures based on the VP copolymer with triethylene glycol dimethacrylate are shown to be thermosensitive and decompose when the temperature rises to physiologically significant values. According to the TEM data, the polymer particles are spherical and contain inclusions of the PtIV complex ∼4 nm in size. The polymer compositions were studied using CV, TGA, and DSC methods. The results of IR spectroscopic analysis of the polymer compositions and quantum chemical modeling indicate the formation of the hydrogen bond between the NH groups of the complex and VP copolymer.

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References

  1. A. K. Mandal, Int. J. Polym. Mater. Polym. Biomater., 2020, 70, 287; DOI: https://doi.org/10.1080/00914037.2020.1713780.

    Article  Google Scholar 

  2. M. Kalomiraki, K. Thermos, N. A. Chaniotakis, Int. J. Nanomed., 2016, 11, 1; DOI: https://doi.org/10.2147/IJN.S93069.

    Article  CAS  Google Scholar 

  3. R. M. Kannan, E. Nance, S. Kannan, D. A. Tomalia, J. Int. Med., 2014, 276, 579; DOI: https://doi.org/10.1111/joim.12280.

    Article  CAS  Google Scholar 

  4. A. Agrawal, S. Kulkarni, Int. J. Res. Dev. Pharm. Life Sci., 2015, 4, 1700.

    CAS  Google Scholar 

  5. I. V. Ivanov, T. K. Meleshko, A. V. Kashina, A. V. Iakimanskii, Russ. Chem. Rev., 2019, 88, 1248; DOI: https://doi.org/10.1070/RCR4870.

    Article  CAS  Google Scholar 

  6. C. Gao, D. Yan, Progr. Polym. Sci., 2004, 29, 183; DOI: https://doi.org/10.1016/j.progpolymsci.2003.12.002.

    Article  CAS  Google Scholar 

  7. N. M. B. Smeets, Eur. Polym. J., 2013, 49, 2528; DOI: https://doi.org/10.1016/j.eurpolymj.2013.05.006.

    Article  CAS  Google Scholar 

  8. C. M. Paleos, D. Tsiourvas, Z. Sideratou, L.-A. Tziveleka, Exp. Opin. Drug Deliv., 2010, 7, 1387; DOI: https://doi.org/10.1517/17425247.2010.534981.

    Article  CAS  Google Scholar 

  9. X. Zeng, Y. Zhang, Z. Wu, P. Lundberg, M. Malkoch, A. M. Nyström, J. Polym. Sci. Part A: Polym. Chem., 2011, 50, 280; DOI: https://doi.org/10.1002/pola.25027.

    Article  Google Scholar 

  10. Y. Zhou, D. Yan, Chem. Commun., 2009, 9, 1172; DOI: https://doi.org/10.1039/B814560C.

    Article  Google Scholar 

  11. Y. Zhou, W. Huang, J. Liu, X. Zhu, D. Yan, Adv. Mater., 2010, 22, 4567; DOI: https://doi.org/10.1002/adma.201000369.

    Article  CAS  Google Scholar 

  12. N. O’Brien, A. McKee, D. C. Sherrington, A. T. Slark, A. Titterton, Polymer, 2000, 41, 6027; DOI: https://doi.org/10.1016/S0032-3861(00)00016-1.

    Article  Google Scholar 

  13. M. Luzon, C. Boyer, C. Peinado, T. Corrales, M. Whittaker, L. Tao, T. P. Davis, J. Polym. Sci., Part A: Polym. Chem., 2010, 48, 2783; DOI: https://doi.org/10.1002/pola.24027.

    Article  CAS  Google Scholar 

  14. P. Chambon, L. Chen, S. Furzeland, D. Atkins, J. V. M. Weaver, D. J. Adams, Polym. Chem., 2011, 2, 941; DOI: https://doi.org/10.1039/C0PY00369G.

    Article  CAS  Google Scholar 

  15. P. Besenius, S. Slavin, F. Vilela, D. C. Sherrington, React. Funct. Polym., 2008, 68, 1524; DOI: https://doi.org/10.1016/j.reactfunctpolym.2008.08.004.

    Article  CAS  Google Scholar 

  16. S. V. Kurmaz, A. N. Pyryaev, Polymer Sci., Ser. B, 2010, 52, 1; DOI:https://doi.org/10.1134/S156009041001001X.

    Article  Google Scholar 

  17. S. V. Kurmaz, N. A. Obraztsova, A. A. Balakina, A. A. Terent’ev, Russ. Chem. Bull. (Int. Ed.), 2016, 65, 2097; DOI: https://doi.org/10.1007/s11172-016-1558-x.

    Article  CAS  Google Scholar 

  18. S. V. Kurmaz, N. V. Fadeeva, V. M. Ignat’ev, V. A. Kurmaz, S. A. Kurochkin, N. S. Emel’yanova, Molecules, 2020, 25, 6015; DOI: https://doi.org/10.3390/molecules25246015.

    Article  CAS  Google Scholar 

  19. S. V. Kurmaz, T. N. Rudneva, N. A. Sanina, Mendeleev Commun., 2018, 28, 73; DOI: https://doi.org/10.1016/j.mencom.2018.01.024.

    Article  CAS  Google Scholar 

  20. T. N. Rudneva, N. S. Emel’yanova, S. V. Kurmaz, Chem. Papers, 2019, 73, 95; DOI: https://doi.org/10.1007/s11696-018-0569-5.

    Article  CAS  Google Scholar 

  21. S. V. Kurmaz, V. D. Sen, A. V. Kulikov, D. V. Konev, V. A. Kurmaz, A. A. Balakina, A. A. Terent’ev, Russ. Chem. Bull., 2019, 68, 1769; DOI: https://doi.org/10.1007/s11172-019-2623-z.

    Article  CAS  Google Scholar 

  22. S. V. Kurmaz, N. V. Fadeeva, B. S. Fedorov, G. I. Kozub, N. S. Emel’yanova, V. A. Kurmaz, R. A. Manzhos, A. A. Balakina, A. A. Terentyev, Mendeleev Commun., 2020, 30, 22; DOI: https://doi.org/10.1016/j.mencom.2020.01.007.

    Article  CAS  Google Scholar 

  23. N. J. Wheate, S. Walker, G. E. Craig, R. Oun, Dalton Trans., 2010, 39, 8113; DOI: https://doi.org/10.1039/C0DT00292E.

    Article  CAS  Google Scholar 

  24. S. Dilruba, G. V. Kalayda, Cancer Chemotherapy and Pharmacology, 2016, 77, 1103; DOI: https://doi.org/10.1007/s00280-016-2976-z.

    Article  CAS  Google Scholar 

  25. V. P. Torchilin, J. Control. Release, 2001, 73, 137; DOI: https://doi.org/10.1016/s0168-3659(01)00299-1.

    Article  CAS  Google Scholar 

  26. R. Duncan, Nat. Rev. Drug Discov., 2003, 2, 347; DOI: https://doi.org/10.1038/nrd1088.

    Article  CAS  Google Scholar 

  27. D. Peer, J. M. Karp, S. Hong, O. C. Farokhzad, R. Margalit, R. Langer, Nat. Nanotechnol., 2007, 2, 751; DOI: https://doi.org/10.1038/nnano.2007.387.

    Article  CAS  Google Scholar 

  28. B. S. Fedorov, M. A. Fadeev, G. I. Kozub, S. M. Aldoshin, Z. G. Aliev, L. O. Atovmyan, N. P. Konovalova, T. E. Sashenkova, T. A. Kondrat’eva, S. V. Blokhina, Pharm. Chem. J., 2009, 43, 134; DOI: https://doi.org/10.1007/s11094-009-0256-5.

    Article  CAS  Google Scholar 

  29. B. S. Fedorov, M. A. Fadeev, G. I. Kozub, A. N. Chekhlov, N. P. Konovalova, T. E. Sashenkova, E. I. Berseneva, O. V. Dobrokhotova, L. V. Tatyanenko, Russ. Chem. Bull., 2011, 60, 1181; DOI: https://doi.org/10.1007/s11172-011-0186-8.

    Article  CAS  Google Scholar 

  30. A. G. Krivenko, A. S. Kotkin, V. A. Kurmaz, Russ. J. Electrochem., 2005, 41, 137; DOI: https://doi.org/10.1007/s11175-005-0025-z.

    Article  CAS  Google Scholar 

  31. V. P. Fadeeva, V. D. Tikhova, Kolichestvennyi elementnyi analiz organicheskikh veshchestv i materialov [Quantitative Elemental Analysis of Organic Substances and Materials], Novosibirsk Gos. Univ., Novosibirsk, 2013, 38 pp. (in Russian).

    Google Scholar 

  32. S. V. Kurmaz, V. Yu. Gak, V. A. Kurmaz, D. V. Konev, Russ. J. Phys. Chem. A, 2018, 92, 329; DOI: https://doi.org/10.1134/S0036024418020152.

    Article  CAS  Google Scholar 

  33. M. J. Frisch, G. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. Martin, L. K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Revis. B.01, Gaussian, Inc., Wallingford CT, 2009.

    Google Scholar 

  34. J. Tao, J. P. Perdew, V. N. Staroverov, G. E. Scuseria, Phys. Rev. Lett., 2003, 91, 146401; DOI: https://doi.org/10.1103/PhysRevLett.91.146401.

    Article  Google Scholar 

  35. V. M. Ignat’ev, N. S. Emel’yanova, N. A. Sanina, Russ. Chem. Bull., 2020, 69, 2265; DOI: https://doi.org/10.1007/s11172-020-3045-7.

    Article  Google Scholar 

  36. U. Koch, P. L. A. Popelie, J. Phys. Chem., 1995, 99, 9747; DOI: https://doi.org/10.1021/j100024a016.

    Article  CAS  Google Scholar 

  37. M. C. McCormick, K. Keijzer, A. Polavarapu, F. A. Schultz, M.-H. Baik, J. Am. Chem. Soc., 2014, 136, 8992; DOI: https://doi.org/10.1021/ja5029765.

    Article  CAS  Google Scholar 

  38. J. J. Wilson, S. J. Lippard, Inorg. Chem., 2011, 50, 3103; DOI: https://doi.org/10.1021/ic2000816.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    S. V. Kurmaz, N. V. Fadeeva, B. S. Fedorov, G. I. Kozub, V. A. Kurmaz, V. M. Ignat’ev & N. S. Emel’yanova

  2. Faculty of Fundamental Physical and Chemical Engineering, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    V. M. Ignat’ev

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  1. S. V. Kurmaz
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Correspondence to S. V. Kurmaz.

Additional information

Based on the materials of the VIII All-Russian Kargin Conference “Polymers-2020” (November 9–13, 2020, Moscow, Russia).

Deceased.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1832–1844, September, 2021.

The authors are grateful to E. O. Perepelitsyna for chromatographic analysis of the copolymers and to R. A. Manzhos for help in CV experiment and useful discussion.

This work carried out in the framework of state assignment (Themes Nos. AAAA-A19-119041090087-4, AAAAA19-119032690060-9, AAAA-A19-119071890015-6, and AAAA-A19-119061890019-5) using equipment of the Analytical Center for Collective Use at the Institute of Problems of Chemical Physics (Russian Academy of Sciences).

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

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Kurmaz, S.V., Fadeeva, N.V., Fedorov, B.S. et al. Amphiphilic copolymers of N-vinylpyrrolidone with (di)methacrylates as promising carriers for the platinum(IV) complex with antitumor activity. Russ Chem Bull 70, 1832–1844 (2021). https://doi.org/10.1007/s11172-021-3289-x

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