СИНТЕЗ НОВЫХ БИОЛОГИЧЕСКИ АКТИВНЫХ ПОЛИМЕРНЫХ БИОКОНЪЮГАТОВ НА ОСНОВЕ ЛУПАНОВЫХ АЛЛИЛАМИДОВ

Article Russian OPEN
Горбунова, Марина Николаевна ; Крайнова, Гульназ Фаизовна ; Толмачева, Ирина Анатольевна ; Гришко, Виктория Викторовна (2014)
  • Publisher: Altai State University
  • Journal: Khimiia rastitel'nogo syr'ia (Chemistry of plant raw material) (issn: 1029-5143)
  • Related identifiers: doi: 10.14258/jcprm.201404238
  • Subject: Lupanova allylamides, radical copolymerization, cytotoxic activity | лупановые аллиламиды, радикальная сополимеризация, цитотоксическая активность
    mesheuropmc: macromolecular substances | technology, industry, and agriculture

The work is devoted to the synthesis of new copolymers based on allylamides of betulonic and 2 hydroximinobetulonic acids and study of their cytotoxic activity. Allylamides of betulonic and 2 hydroximinobetulonic acids were prepared by the reaction of corresponding acids with allylamine in the presence of oxalyl chloride and triethylamine. It was established that the allylamides obtained do not homopolymerize, but copolymerize with low rates with acrylonitrile and N-vinylpyrrolidone in the presence of radical initiators The investigations of radical copolymerization of allylamides with acrylonitrile and N-vinyl­pyrrolidone showed that the resulting copolymers have a statistical distribution of the comonomer units in the macromolecule, wherein in the entire range of monomer concentrations the copolymers are enriched by the vinyl monomer units. The copolymerization rates are considerably reduced by increasing the content of allylamides in the initial monomer mixture in all copolymerization systems, the copolymerization rate of allylamide with acrylonitrile is higher than with N-vinylpyrrolidone. At the copolymerization in bulk with enhancing degree of conversion there is a "gel-effect", which is associated with an increasing of the viscosity in the absence of solvent; at the copolymerization in solution "gel-effect" is absent. The structure of the copolymers obtained was determined by 1H NMR spectroscopy. It was established that the products obtained are a mixture of copolymers of allyl amides and oligomers thereof. In the spectra of the reaction products a number of additions of the vinyl monomer with the participating of double bond of isopropylidene group is also observed. The copolymers obtained have a cytotoxic activity: the copolymer of allylamide of betulonic acid with N-vinylpyrrolidone exhibits 4-fold higher activity against MS culture when compared with the initial ally amide and is promising for developing new bioactive polymer bioconjugates.
  • References (41)
    41 references, page 1 of 5

    1. Lee S.M., Min B.S., Lee C.G., Kim K.S., Kho Y.H. Planta Med. 2003, vol. 69, no. 11, pp. 1051-1054.

    2. olstikova .G., Sorokina I.V., Tolstikov G. ., Tolstikov .G., Flekhter .B. Rus. J. Bioorg. Chem. 2006, vol. 32, no. 3, pp. 291-307.

    3. Era V., Jaaskelamen P., Ukkonen . J. Amer. Oil Chem. Soc. 1981, vol. 58, no. 1, pp. 20-23.

    4. Era V., Mustonen ., Jaaskelainen . Mackromol. Chem. Rapid Commun. 1981, Vol. 2, pp. 283-286.

    5. Patent 1671666 (SU). 1991. (in Russ.).

    6. Flehter O.B., Ashavina O.Ju., Boreko E.I., Karachurina L.T., Pavlova N.I., Kabal'nova N.N., Savinova O.V., Galin F.Z., Nikolaeva S.N., Zarudij F.S., Baltina L.A., Tolstikov G.A. Himiko-farmacevticheskij zhurnal, 2002, vol. 36, no. 6, pp. 21-24. (in Russ.).

    7. Patent 2477134 (RU). 2013. (in Russ.).

    8. Flehter O.B., Nigmatullina L.R., Baltina L.A., Karachurina L.T., Galin F.Z., Zarudij F.S., Tolstikov G.A., Boreko E.I., Pavlova N.I., Nikolaeva S.N., Savinova O.V. Himiko-farmacevticheskij zhurnal, 2002, vol. 36, no. 9, pp. 26-28. (in Russ.).

    9. Tolmacheva I.A., Grishko V.V., Boreko E.I., Savinova O.V., Pavlova N.I. Himija prirodnyh soedinenij, 2009, no. 5, pp. 566-568. (in Russ.).

    10. Krajnova G.F., Tolmacheva I.A., Gorbunova M.N., Grishko V.V. Himija prirodnyh soedinenij, 2013, no. 2, pp. 239- 242. (in Russ.).

  • Metrics
    No metrics available
Share - Bookmark