SYNTHESIS AND ANTIBACTERIAL PROPERTIES OF 4-AMINOPHENYLSULFONAMIDE IMMOBILIZED ON THE POLYMERIC CARRIER

Authors

  • V. N. Toropin Ukrainian State Chemical Technology University, Dnipro
  • G. N. Kremenchutskiy Dnipropetrovsk State Medical Academy, Dnipro
  • K. S. Burmistrov Ukrainian State Chemical Technology University, Dnipro
  • A. A. Shunkevich Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Minsk
  • A. P. Polikarpov Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Minsk

DOI:

https://doi.org/10.11603/2312-0967.2017.1.7525

Keywords:

immobilization, 4-aminophenylsulfonamide copolymer, sulfanilamide.

Abstract

The aim of the study. Today the immobilization of drugs to the polymeric carriers is increasingly important, due to the requirements to reduce the toxicity and prolongation of action of drugs. It is known the immobilization of the Sulfonamides on the Stiromali, methacrylate polymer matrices, wherein the pharmacologically active sulfanilamide easily remove from the polymer upon the application, by the acid hydrolysis. At the same time it is noted that immobilized sulfonamides derived from aminomethylated Styrene-divinylbenzene copolymer, although hydrolytic stability, maintain the antibacterial properties. In order to expand the examples of covalent immobilization of sulfonamides we synthesized 4-aminophenylsulfonamide on pellet and brous forms of styrene and divinylbenzene with SO2 as a bridging group.

Materials and Methods. As a raw materials, we used the pellet macroporous sulfonated Styrene-divinylbenzene copolymer and copolymers Polypropylene and Styrene. Sulfochlorination of these copolymers the polymeric sulfonyl chlorides were obtained. This compounds were used in the reaction with 4-aminophenilsulfonamidom. Antibacterial properties of the material were studied by determining the growth inhibition zones of test E. coli K12 microorganism in a nutrient medium.

Results and Discussion. The structure of synthesized immobilized 4-aminophenylsulfonamide proven by IR spectroscopy. It is shown that such materials exhibit a relatively pronounced antibacterial properties test culture of microorganisms E. coli K-12, in spite of their resistance to hydrolysis. 

Сonclusions. It is suggested that the hydrolysis of the materials takes place at a specic enzymatic catalysis in the medium with the release of 4-aminophenylsulfonamide.

Author Biographies

V. N. Toropin, Ukrainian State Chemical Technology University, Dnipro

applicant of Department Technology of organic substances and pharmaceutical preparations

G. N. Kremenchutskiy, Dnipropetrovsk State Medical Academy, Dnipro

Doctor of Medicine, Professor of Department of Microbiology, Virology, Immunology and Epidemiology

K. S. Burmistrov, Ukrainian State Chemical Technology University, Dnipro

Doctor of Chemical Sciences, Professor of Department Technology of organic substances and pharmaceutical preparations

A. A. Shunkevich, Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Minsk

Ph.D. (Chem.), Research Scientist, Laboratory of Ion Exchange Fibers Synthesis and Properties Study

A. P. Polikarpov, Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Minsk

Ph.D. (Chem.), Head of the Laboratory of Ion Exchange Fibers Synthesis and Properties Study

References

Sokolovskyi MV, Smyrnova MYu, Tarabukyna EB. [Synthesis of copolymers of acrylamide with hydrochloride of 3-aminoethyl methacrylate – carriers of biologically active substances]. ZhOKh. 2012;10: 1650-5.

Hsu B, Hagerman S, Jamieson K. Multifunctiohal self-assembled lm for hemostat and sustained antiinfective delivery. ACS Biomater. Sci. Eng. 2015;1(3): 148-56.

Schukovskaia LL, Kapustianskaia AM, Kropachev VA. A. s. 332103 SSSR, MKY S08F 27/06. Method for the preparation of water-soluble physiologically active polymers / (SSSR). – № 1431245/23-5; zaiavl. 30.04.70; opubl. 14.03.72, Biul № 10.

Chuіko LS, Rochniak SE, Voloshynets VL. [Unsaturated sulfonamides and polymers based on them]. Ukr.khym.zh. 1991;6: 633-67.

Chuіko LS, Karpliuk YuA, Tkachuk VO. [Synthesis and study of polymers with biologically active functional groups]. Ukr.khim.zhurn. 2000;4: 121-5. Ukrainian.

Krupka OM, Yukhymenko NM, Kolendo OYu, Kovinia MV, inventors, assignee. Physiologically active polymers containing sulphonamides. UA 6348 (Patent) 2005 Mai 16. Ukrainian.

Cheol-Jin Kim, Jee-Yeon Kim, Jang-Woong Byun, Рreparation of polystyrene beads containing sulfonamidegroups and their application to polymeric biocides. Environ. Eng. Res. 2006;6: 325-32.

Markevych DA. Pharmacology [Фармакологія]. Moscow: Medytsyna;1980. Russian.

Zubakova LB, Tevlyna AS, Davankov AB. Synthetic ion exchange materials [Синтетичні іонообмінні матеріали]. Moscow: Khimiya, 1978. Russian.

Burmistrov KS, Murashevych BV, Toropin VM, Toropin MV, inventors, assignee. The polymer material with immobilized active chlorine that shows antimicrobial properties. UA 112187 (Patent) 2016 Hruden 12. Ukrainian.

Tsundel G. Hydration and intermolecular interaction [Гідратація і міжмолекулярна взаємодія]. per s angl. pod red. Chirgadze YN. Moscow: Mir, 1972. Russian.

Qisheng R, Wenqiang H, Fenzhi Z, Binglin H. Infrared spectrum feature of the sulfonyl group bound to crosslinked polystyrenes Acta. Polymerica Sinica. 1990;1: 7-12.

Yllaryonov AY, Syrovatskyi YP, Yllaryonova EA, inventors. State Educational Establishment of Higher Professional Education "Irkutsk State Transport University", assignee. Method for the determination of sulfanyl acid amide derivatives RU 2440573 (Patent) 2012 Sichen 20. Russian.

Downloads

Published

2017-03-24

How to Cite

Toropin, V. N., Kremenchutskiy, G. N., Burmistrov, K. S., Shunkevich, A. A., & Polikarpov, A. P. (2017). SYNTHESIS AND ANTIBACTERIAL PROPERTIES OF 4-AMINOPHENYLSULFONAMIDE IMMOBILIZED ON THE POLYMERIC CARRIER. Pharmaceutical Review Farmacevtičnij časopis, (1), 5–10. https://doi.org/10.11603/2312-0967.2017.1.7525

Issue

No. 1 (2017)

Section

Synthesis of biologically active compounds

License

The authors who publish their materials in this journal agree with the following terms:

  • Authors reserve the right to authorship of their work and assign to the journal the right to first publish this work under the terms of the Creative Commons Attribution License, which allows other persons to freely distribute the published work with a mandatory reference to the authors of original work and the first publication of work in this journal Результат пошуку зображень за запитом "CC-BY logo".
  • Authors have the right to make independent extra-exclusive work agreements in the form they are published by this journal (for example, posting work in an electronic repository of an institution or publishing as part of a monograph), provided that the link to the first publication of the work in this journal is maintained.

Journal policy allows and encourages publication of manuscripts on the Internet (for example, in institutions repositories or on personal websites), both before the publication of this manuscript and during its editorial review, as it contributes to productive scientific discussion and positively affects the efficiency and dynamics of the citation of the published work (see The Effect of Open Access).