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Copolymers of Methyl Acrylate and Vinylazoles: Synthesis, Thermolabile Properties, and Grafting of Polyamine Chains

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Abstract

New copolymers of methyl acrylate with 1-vinylimidazole, 1-vinyl-1,2,4-triazole, and 4-vinyl-1,2,3-triazole are synthesized by radical copolymerization. It is shown that the reactivity ratios for methyl acrylate and 1-vinylimidazole are 0.83 ± 0.09 and 0.25 ± 0.02, for methyl acrylate and 1-vinyl-1,2,4-triazole are 1.0 ± 0.04 and 0.27 ± 0.01, and for methyl acrylate and (4-vinyl-1Н-1,2,3-triazolyl)-methyl pivalate are 0.56 ± 0.03 and 2.90 ± 0.20, respectively. The behavior of the copolymers in aqueous media and their thermoresponsive properties are studied by potentiometric titration and dynamic light scattering. Copolymer macromolecules occur in aqueous solutions in the form of large associates the fraction of which increases upon heating; in some cases, an insoluble phase is formed. It is found that the copolymers with the grafted oligopropylamine moieties containing N-vinylazole units can interact with the DNA oligonucleotide, stimulating their research as agents for the delivery of nucleic acids to living cells.

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REFERENCES

  1. S. Tan, K. Saito, and M. T. Hearn, Curr. Opin. Biotechnol. 53, 209 (2018).

    Article  CAS  PubMed  Google Scholar 

  2. C. Lu and M. W. Urban, Prog. Polym. Sci. 78, 24 (2018).

    Article  CAS  Google Scholar 

  3. J. Xu, P. Zhu, Y. Wang, and K.-L. Zhang, Inorg. Chim. Acta 503, (2019). https://doi.org/10.1016/j.ica.2019.119376

  4. Y. Xian, Y. Shui, M. Li, C. Pei, Q. Zhang, and Y. Yao, J. Appl. Polym. Sci. 137, (2020). https://doi.org/10.1002/app.49032

  5. X. Fu, L. Hosta-Rigau, R. Chandrawati, and J. Cui, Chem – Cell Press 4, 2084 (2018).

  6. M. Sponchioni, U. C. Palmiero, and D. Moscatelli, Mater. Sci. Eng., C 102, 589 (2019).

    Article  CAS  Google Scholar 

  7. A. Koochaki, M. R. Moghbeli, S. J. Nikkhah, A. Ianiro, and R. Tuinier, RSC Adv. 10, 3233 (2020).

  8. M. V. Shirmanova, I. N. Druzhkova, M. M. Lukina, M. E. Matlashov, V. V. Belousov, L. B. Snopova, N. Prodanetz, V. V. Dudenkova, S. A. Lukyanov, and E. V. Zagaynova, Biochim. Biophys. Acta 1850, 1905 (2015).

    Article  CAS  PubMed  Google Scholar 

  9. O. Boussif, F. Lezoualc, M. A. Zanta, M. D. Mergny, D. Scherman, B. Demeneix, and J.-P. Behr, Proc. Natl. Acad. Sci. U. S. A. 92, 7297 (1995).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. M. Chen, Y. Tang, T. Wang, Q. Long, Z. Zeng, H. Chen, and X. Feng, Mater. Sci. Eng., C 69, 1367 (2016).

    Article  CAS  Google Scholar 

  11. X. Wang, D. Niu, C. Hu, and P. Li, Curr. Pharm. Des. 21, 6140 (2015).

    Article  CAS  PubMed  Google Scholar 

  12. A. Katchalsky, J. Mazur, and P. Spitnik, J. Polym. Sci. 23 (104), 513 (1957).

    Article  CAS  Google Scholar 

  13. D. Fischer, Y. Li, B. Ahlemeyer, J. Krieglstein, and T. Kissel, Biomaterials 24, 1121 (2003).

    Article  CAS  PubMed  Google Scholar 

  14. T. G. Ermakova, N. P. Kuznetsova, and K. A. Maksimov, Russ. J. Appl. Chem. 76, 1971 (2003).

    Article  CAS  Google Scholar 

  15. V. N. Kizhnyaev, F. A. Pokatilov, and L. I. Vereshchagin, Polym. Sci., Ser. C 50, 1 (2008).

    Article  Google Scholar 

  16. M. V. Kurik, G. F. Myachina, and T. G. Ermakova, Mol. Cryst. Liq. Cryst. 468, 669 (2007).

    Article  CAS  Google Scholar 

  17. V. N. Kizhnyaev, T. L. Petrova, F. A. Pokatilov, R. G. Zhitov, and O. A. Edel’shtein, Polym. Sci., Ser. B 56, 490 (2014).

    Google Scholar 

  18. N. L. Mazyar, V. V. Annenkov, V. A. Kruglova, S. M. Ananiev, E. N. Danilotseva, A. V. Rokhin, and S. V. Zinchenko, Russ. Chem. Bull. 49, 2013 (2000).

    Article  CAS  Google Scholar 

  19. N. P. Bayramgil, Colloids Surf., B 97, 182 (2012).

    Article  CAS  Google Scholar 

  20. G. Kandasamy, E. N. Danilovtseva, V. V. Annenkov, and U. M. Krishnan, Beilstein J. Nanotechnol. 11, 354 (2020).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. V. V. Annenkov, U. M. Krishnan, V. A. Pal’shin, S. N. Zelinskiy, G. Kandasamy, and E. N. Danilovtseva, Chin. J. Polym. Sci. 36, 1114 (2018).

    Article  CAS  Google Scholar 

  22. E. N. Danilovtseva, U. M. Krishnan, V. A. Pal’shin, and V. V. Annenkov, Chin. J. Polym. Sci. 37, 637 (2019).

    Article  CAS  Google Scholar 

  23. V. Aseyev, H. Tenhu, and F. M. Winnik, Adv. Polym. Sci. 242, 29 (2011).

    Article  CAS  Google Scholar 

  24. T. Mori, Y. Fukuda, H. Okamura, K. Minagawa, S. Masuda, and M. Tanaka, J. Polym. Sci., Part A: Polym. Chem. 42, 2651 (2004).

    Article  CAS  Google Scholar 

  25. X. Peng, Y. Zhang, W. Fehg, L.-M. Ai, and F. Zhang, J. Mol. Struct. 1041, 139 (2013).

    Article  CAS  Google Scholar 

  26. G. A. Mun, P. I. Urkimbaeva, M. B. Primbetova, R. B. Bakytbekov, A. Shaikhutdinova, and G. Zh. Eligbaeva, Izv. Nauch.-Tekh. O-va “KAKhAK”, No. 2, 36 (2012).

  27. H. Okamura, S. Masuda, K. Minagawa, T. Mori, M. Tanaka, Eur. Polym. J. 38, 639 (2008).

    Article  Google Scholar 

  28. G. A. Mun, RF Patent No. 19953 (2008).

  29. E. N. Danilovtseva, M. A. Chafeev, and V. V. Annenkov, J. Polym. Sci., Part A: Polym. Chem. 50, 1539 (2012).

    Article  CAS  Google Scholar 

  30. H. Hopff and M. Lippay, Macromol. Chem. 66, 157 (1963).

    Article  CAS  Google Scholar 

  31. V. V. Annenkov, S. N. Zelinskiy, E. N. Danilovtseva, and C. C. Perry, ARKIVOC 13, 116 (2009).

    Article  Google Scholar 

  32. B. Keil, Laboratory Technique of Organic Chemistry, Ed. by L. D. Bergel’sona (Mir, Moscow, 1966) [in Russian].

  33. A. Kubotera and R. Saito, Polym. J. 48, 611 (2016).

    Article  CAS  Google Scholar 

  34. H. Mori, K. Ishikawa, Y. Abiko, K. Nakabayashi, A. Onuma, and M. Morishima, Polymer 54, 2001 (2013).

    Article  CAS  Google Scholar 

  35. M. Talu, E. U. Demiroğlu, Ş. Yurdakul, and S. Badoğlu, Spectrochim. Acta, Part A 134, 267 (2015).

    Article  CAS  Google Scholar 

  36. Q. Liu and M. Zhu, Polym. Test. 56, 174 (2016).

    Article  CAS  Google Scholar 

  37. V. V. Annenkov, O. V. Lebedeva, E. N. Danilovtseva, and A. I. Mikhaleva, Polym. Sci., Ser. B 43, 247 (2001).

    Google Scholar 

  38. J-F. Kuo and C. -Y. Chen, J. Appl. Polym. Sci. 26, 1117 (1980).

    Article  Google Scholar 

  39. A. I. Ezrielev, E. L. Brokhina, and E. S. Roskin, Vysokomol. Soedin., Ser. A 11, 1670 (1969).

    CAS  Google Scholar 

  40. M. B. Lachinov and E. V. Chernikova, Manuals to Practice on Polymer Synthesis, Ed. by V. P. Shibaeva (MGU, Moscow, 2002) [in Russian].

    Google Scholar 

  41. V. A. Kruglova, V. N. Kizhnyaev, N. A. Ivanova, and L. I. Vereshchagin, Vysokomol. Soedin., Ser. B 29, 416 (1987).

    CAS  Google Scholar 

  42. J. L. Lippert, J. A. Robertson, J. R. Havens, and J. S. Tan, Macromolecules 18, 63 (1985).

    Article  CAS  Google Scholar 

  43. V. A. Kruglova, V. V. Annenkov, G. V. Ratovskii, and O. A. Shivernovskaya, Vysokomol. Soedin., Ser. B 30, 233 (1988).

    CAS  Google Scholar 

  44. E. N. Zil’berman, Vysokomol. Soedin., Ser. B 21, 33 (1979).

    Google Scholar 

  45. U. P. Strauss, U. P. Barbieri, and G. Wong, J. Phys. Chem. 83, 2840 (1979).

    Article  CAS  Google Scholar 

  46. K. A. Hasselbalch, Biochem. Z. 78, 112 (1917).

    Google Scholar 

  47. E. F. Vainshtein, A. A. Berlin, and S. G. Entelis, Vysokomol. Soedin., Ser. B 17, 835 (1975).

    CAS  Google Scholar 

  48. V. V. Annenkov, V. A. Kruglova, and N. L. Mazyar, J. Polym Sci., Part B: Polym. Phys. 36, 931 (1998).

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

We are grateful to the Shared Research Center Ultramicroanalysis for providing us with the equipment.

Funding

This work was supported by the Ministry of Science and Higher Education of the Russian Federation and the Russian Academy of Sciences (project no. АААА-А19-119100490016-4).

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Correspondence to M. S. Strelova.

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Translated by T. Soboleva

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Strelova, M.S., Danilovtseva, E.N. & Annenkov, V.V. Copolymers of Methyl Acrylate and Vinylazoles: Synthesis, Thermolabile Properties, and Grafting of Polyamine Chains. Polym. Sci. Ser. B 63, 41–51 (2021). https://doi.org/10.1134/S1560090421010061

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