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Synthesis and characterization of pyridoxine, nicotine and nicotinamide salts of dithiophosphoric acids as antibacterial agents against resistant wound infection

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dc.contributor.author Dang T.
dc.contributor.author Nizamov I.
dc.contributor.author Salikhov R.
dc.contributor.author Sabirzyanova L.
dc.contributor.author Vorobev V.
dc.contributor.author Burganova T.
dc.contributor.author Shaidoullina M.
dc.contributor.author Batyeva E.
dc.contributor.author Cherkasov R.
dc.contributor.author Abdullin T.
dc.date.accessioned 2020-01-21T20:40:42Z
dc.date.available 2020-01-21T20:40:42Z
dc.date.issued 2019
dc.identifier.issn 0968-0896
dc.identifier.uri https://dspace.kpfu.ru/xmlui/handle/net/157602
dc.description.abstract © 2018 Elsevier Ltd The pyridine-derived biomolecules are of considerable interest in developing medicinal compounds with various specific activities. Novel ammonium salts of pyridoxine, (S)-(–)-nicotine and nicotinamide with O,O-diorganyl dithiophosphoric acids (DTPA) were synthesized and characterized. The complexation of chiral monoterpenyl DTPA, including (S)-(–)-menthyl, (R)-(+)-menthyl, (1R)-endo-(+)-fenchyl, (1S,2S,3S,5R)-(+)-isopinocampheolyl derivatives, with pyridoxine and nicotine provided effective antibacterial compounds 3a,b,e,f, and 5a,b,d,f with MIC values against Gram-positive bacteria as low as 10 µM (6 µg/mL). Two selected pyridoxine and nicotine salts based on menthyl DTPA 3a and 5a were similarly active against antibiotic-resistant bacteria from burn wounds including MRSA. The compounds had enhanced amphiphilic and hemolytic properties and effectively altered surface characteristics and matrix-secreting ability of P. aeroginosa and S. aureus. MBC/MIC ratios of 3a and 5a suggested the bactericidal mode of their action. Furthermore, the compounds exhibited moderate cytotoxicity towards human skin fibroblasts (IC50 = 48.6 and 57.6 µM, respectively, 72 h), encouraging their further investigation as potential antimicrobials against skin and wound infections.
dc.relation.ispartofseries Bioorganic and Medicinal Chemistry
dc.subject Antibacterial agents
dc.subject Cytotoxicity
dc.subject Dithiophosphoric acids
dc.subject Monoterpenes
dc.subject MRSA
dc.subject Nicotinamide
dc.subject Nicotine
dc.subject Pyridoxine
dc.subject Quaternary ammonium salts
dc.subject Wound infection
dc.title Synthesis and characterization of pyridoxine, nicotine and nicotinamide salts of dithiophosphoric acids as antibacterial agents against resistant wound infection
dc.type Article
dc.relation.ispartofseries-issue 1
dc.relation.ispartofseries-volume 27
dc.collection Публикации сотрудников КФУ
dc.relation.startpage 100
dc.source.id SCOPUS09680896-2019-27-1-SID85057256051


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  • Публикации сотрудников КФУ Scopus [24551]
    Коллекция содержит публикации сотрудников Казанского федерального (до 2010 года Казанского государственного) университета, проиндексированные в БД Scopus, начиная с 1970г.

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