СИНТЕЗ И ИССЛЕДОВАНИЕ АНТИБАКТЕРИАЛЬНОЙ АКТИВНОСТИ БРОМПРОИЗВОДНЫХ ПОРФИРИНПОЛИМЕРОВ И ИХ ЦИНКОВЫХ КОМПЛЕКСОВ
Аннотация
Проведено бромирование 2-формил-5,10,15,20-тетрафенил-порфирина и его цинковых (II) комплексов в фенильные кольца (I) и в β-положения макрогетероцикла (II). На основе этих соединений были получены водорастворимые порфиринсодержащие полимеры методом ковалентной иммобилизации на поливиниловый спирт. Определено антибактериальное действие полученных порфиринполимеров на тест-культуры Escherichia coli АТСС 25922, Candida albicans АТСС 885-653, Staphylococcus aureus АТСС 653.
Дляцитирования:
Печникова Н.Л., Алопина Е.В., Кузнецов О.Ю., Агеева Т.А., Койфман О.И. Синтез и исследование антибактериальной активности бромпроизводных порфиринполимеров и их цинковых комплексов. Изв. вузов. Химия и хим. технология. 2017. Т. 60. Вып. 2. С. 52-59.
Литература
Tomé J.P.C., Neves M.G.P.M.S., Tomé A.C., Cavaleiro J.A.S., Soncin M., Magaraggia M., Ferro S., Jori G. Synthesis and antibacterial activity of new poly-S-lysine – porphyrin conjugates. J. Med. Chem. 2004. V. 47. N 26. P. 6649-6652. DOI: 10.1021/jm040802v.
Kuruppuarachchi M., Savoie H., Lowry A., Alonso C., Boyle R.W. Polyacrylamide nanoparticles as a delivery system in pho-todynamic therapy. Mol. Pharmaceutics. 2011. V. 8. N 3. P. 920-931. DOI: 10.1021/mp200023y.
Wang F., Ding K., Wu F. Self-assembly of novel tris(p-carboxyphenyl) porphyrin monomer and its copolymers with acrylamide in aqueous media. Dyes and Pigments. 2011. V. 91. N 2. P. 199-207. DOI: 10.1016/j.dyepig.2011.03.008.
Alopina E.V., Ageeva T.A., Koifman O.I. Immobilization of copper complex of 2-formyl-5,10,15,20-tetraphenylporphyrin on polyvinyl alcohol. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2011. V. 54. N 12. P. 81-85 (in Russian).
Berezin B.D., Berezin D.B. In: Advances in porphyrin chemistry. SPb.: The Scientific Research Institute of Chemistry, St-Petersburg University. 1999. V. 2. P. 128-141 (in Russian).
Nikitina N.I., Potapov G.P. Synthesis and radio-biological activity of water soluble derivatives of copper complex of chlorine E6. Khimiya Rastitel’nogo Syr’ya. 2002. N 2. P. 79-84 (in Russian).
Koifman O.I., Ageeva T.A. Porphyrin polymers: synthesis, properties, and application. Polymer Science. Series C. 2004. V. 46. N 1. P. 49-72.
Amao Y., Tabuchi Y., Yamashita Y., Kimura K. Novel optical oxygen sensing material: metalloporphyrin dispersed in fluori-nated poly(aryl ether ketone) films. Europ. Polymer J. 2002. V. 38. N 4. P. 675-681. DOI: 10.1016/S0014-3057(01)00235-X.
Alopina E.V., Ageeva T.A., Lyubimtsev A.V., Kuznetsov O. Yu., Syrbu S.A., Koifman O.I. Synthesis and immobilization of β-formyl-meso-nitrophenyl-triphenyl-porphyrin and its copper complex on polyvinyl alcohol. Macroheterocycles. 2012. V. 5. N 1. P. 76-80 (in Russian).
Basak A., Abouelhassan Y., Huigens R.W. Halogenated quinolines discovered through reductive amination with potent eradica-tion activities against MRSA, MRSE and VRE biofilms. Org. Biomol. Chem. 2015. V. 13. N 41. P. 10290-10294. DOI: 10.1039/C5OB01883H.
Berezin B.D., Enikolopyan N.S. Metalloporphyrins. М.: Nauka. 1988. 159 p.
Wang L.-Z., Li X.-Q., An Y.-S. 1,5-Benzodiazepine derivatives as potential antimicrobial agents: design, synthesis, biological evaluation, and structure – activity relationships. Org. Biomol. Chem. 2015. V. 13. N 19. P. 5497-5509. DOI: 10.1039/C5OB00655D.
Tse M.K., Zhou Z., Thomas C.W., Chan K.S., Chan M. Regioselective bromination and subsequent suzuki cross-coupling of highly electron deficient 5,10,15,20-tetrakis-(trifluoromethyl)porphyrin. Tetrahedron. 2000. V. 56. N 39. Р. 7779-7783. DOI: 10.1016/S0040-4020(00)00697-9.
Kato A., Hartnell R.D., Yamashita M., Miyasaka H., Sugiura K., Arnold D.P. Selective meso-monobromination of 5,15-diarylporphyrins via organopalladium porphyrins. J. Porphyrins Phthalocyanines. 2004. V. 8. N 10. Р. 1222-1227. DOI: 10.1142/S108842460400057X.
Govorov A.G., Korgenevskiy A.B., Koifman O.I. Immobilization of feofetine "В" on polyvinylalcohol. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 1993. V. 36. N 3. P. 75-81 (in Russian).