SYNTHESIS AND STUDY OF ANTIBACTERIAL ACTIVITY OF BROMINE DERIVATIVES OF PORHYRIN POLYMERS AND THEIR ZINC COMPLEXES

Abstract

A creation of new water-soluble porphyrin-polymers having antibacterial properties is actual today because these substances can be used in a medicine and pharmacology. Therefore, the aim of this work is to obtain a water-soluble polyvinyl alcohol-based immobilizates containing dibromo-derivatives of meso-aryl porphyrins in a side chain of the polymer and the study of their bacterial activity towards Escherichia coli ATCC 25922, Candida albicans ATCC 885-653, Staphylococcus aureus ATCC 653. The bromination of 2-formyl-5,10,15,20-tetraphenylporphyrin and its zinc (II) complexes in the phenyl rings and in the β-positions of macroheterocycle was performed. 2-Formyl-10,15-(4',4'-dibromophenyl)-5,20-diphenylporphyrin and 2-formyl-dibromo-12,13-tetraphenylporphyrin were obtained. Porphyrin metalocomplexes were prepared by the complexation reaction of porphyrin dibromo-derivatives with zinc acetate. The purification of the porphyrin metalocomplexes was carried out by the column chromatography on silica gel, using chloroform as eluent. The structure of the compounds obtained was confirmed by electronic, IR and 1H NMR spectroscopy. Water-soluble porphyrin-polymers were prepared by covalent immobilization of polyvinyl alcohol based on the synthesized porphyrins and their metalocomplexes. The immobilization was carried out by acetalization reaction in an organic medium using 20% sulfuric acid as a catalyst. The immobilizates obtained are intensely colored solid polymer products which are soluble in water and dimethylformamide. Porphyrin weight content in a series of synthesized immobilizates and their immobilization molar degree were determined by electronic absorption spectra. The highest molar degree of porphyrin immobilization on polyvinyl alcohol is achieved at a fixation of 2-formyl-dibromo-12,13-tetraphenylporphyrin and zinc-2-formyl-10,15-(4',4'-dibromo-phenyl)-5,20-diphenylporphyrine on polyvinyl alcohol. It was 0.90 and 0.86, respectively. The influence of the synthesized porphyrin-polymers on Escherichia coli АТСС 25922, Candida albicans АТСС 885-653, Staphylococcus aureus АТСС 653 was investigated by diffusional method of antibacterial activity determining. An investigation of the biological activity of water-soluble immobilizates showed that the polymers and their prepared porphyrin zinc (II) complexes have antibacterial activity against the studied cultures. Significant effect on the inhibition of given cultures have immobilizate containing zinc-2-formyl-10,15-(4',4'-dibromophenyl)-5,20-diphenylporphyrine. For citation:Pechnikova N.L., Alopina E.V., Кuznetsov O.Yu., Ageeva T.A., Koifman O.I. Synthesis and study of antibacterial activity of bromine derivatives of porhyrin polymers and their zinc complexes. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2017. V. 60. N 2. P. 52-59.