ISSN 1070-4272, Russian Journal of Applied Chemistry, 2015, Vol. 88, No. 11, pp. 1793−1799. © Pleiades Publishing, Ltd., 2015.
Original Russian Text © M.S. Borisenko, N.V. Zakharova, E.B. Tarabukina, M.V. Solovskii, 2015, published in Zhurnal Prikladnoi Khimii, 2015, Vol. 88, No. 11,
AND POLYMERIC MATERIALS
Synthesis of N-Vinyl-2-pyrrolidone–3-Butenoic Acid Copolymers
as Drug Carriers
M. S. Borisenko, N. V. Zakharova, E. B. Tarabukina, and M. V. Solovskii
Institute of Macromolecular Compounds, Russian Academy of Sciences, Bol’shoi pr. 31, St. Petersburg, 199004 Russia
Received October 2, 2015
Abstract—New water-soluble copolymers of N-vinylpyrrolidone with 3-butenoic acid were prepared by radical
copolymerization initiated with azobis(isobutyronitrile) or γ-radiation. The relative activities of the monomers in
copolymerization were determined. The distribution of the units in the copolymer macrochains was calculated. The
composition, molecular and hydrodynamic characteristics, and acute toxicity of the copolymers were determined.
The copolymers were used as carriers for rifampicin antibiotic.
The development of new reactive N-vinyl-2-pyrro-
lidone (VP) copolymers is stimulated by their success-
ful use as carriers and modiﬁ ers for various drugs and
biologically active compounds (BACs) . For example,
Katapol antiseptic, which is a complex of Katamin AB
cationic BAC with VP–crotonic acid (CA) copolymer,
is considerably less toxic than Katamin AB itself .
Katapol is permitted for use in medicine for treatment of
purulent wounds and burns. However, VP–CA copolymer
I used in the Katapol formulation as BAC carrier contains
carboxy groups directly bonded to the polymer backbone.
This fact can hinder the interaction of this carrier
with BACs of complex structure, containing sterically
hindered fragments. In this connection, it is promising
to use for BAC modiﬁ cation copolymers of II not with
crotonic but, e.g., with 3-butenoic acid (3-BA) in which
the carboxy groups in the pendant chains are separated
from the polymer backbone by methylene linker:
The goal of this study is synthesis of new N-vinyl-
2-pyrrolidone–3-butenoic acid copolymers, determina-
tion of their compositions, molecular and hydrodynamic
characteristics, and acute toxicity, evaluation of the rela-
tive activities of the monomers in the copolymerization,
and the use of the copolymers as carriers for rifampicin
3-Butenoic acid (CH
–COOH) is an allyl
monomer (АМ) characterized by the degradation chain
transfer to AM.
Because the generated allyl radicals stabilized
by conjugation of the unpaired electron with the π
electrons of the double bond are incapable of initiating
the polymerization, the reaction quickly stops with