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dc.contributor.author | Pugachev M. | |
dc.contributor.author | Shtyrlin N. | |
dc.contributor.author | Sapozhnikov S. | |
dc.contributor.author | Sysoeva L. | |
dc.contributor.author | Iksanova A. | |
dc.contributor.author | Nikitina E. | |
dc.contributor.author | Musin R. | |
dc.contributor.author | Lodochnikova O. | |
dc.contributor.author | Berdnikov E. | |
dc.contributor.author | Shtyrlin Y. | |
dc.date.accessioned | 2018-09-18T20:12:03Z | |
dc.date.available | 2018-09-18T20:12:03Z | |
dc.date.issued | 2013 | |
dc.identifier.issn | 0968-0896 | |
dc.identifier.uri | https://dspace.kpfu.ru/xmlui/handle/net/137500 | |
dc.description.abstract | A series of 23 novel bis-phosphonium salts based on pyridoxine were synthesized and their antibacterial activities were evaluated in vitro. All compounds were inactive against gram-negative bacteria and exhibited the structure-dependent activity against gram-positive bacteria. The antibacterial activity enhanced with the increase in chain length at acetal carbon atom in the order n-Pr > Et > Me. Further increasing of length and branching of alkyl chain leads to the reduction of antibacterial activity. Replacement of the phenyl substituents at the phosphorus atoms in 5,6- bis(triphenylphosphonio(methyl))-2,2,8-trimethyl-4H-[1,3]-dioxino[4,5-c] pyridine dichloride (compound 1) with n-butyl, m-tolyl or p-tolyl as well as chloride anions in the compound 1 with bromides (compound 14a) increased the activity against Staphylococcus aureus and Staphylococcus epidermidis up to 5 times (MICs = 1-1.25 μg/ml). But in practically all cases chemical modifications of compound 1 led to the increase of its toxicity for HEK-293 cells. The only exception is compound 5,6-bis[tributylphosphonio(methyl)]-2,2,8- trimethyl-4H-[1,3]dioxino[4,5-c]pyridine dichloride (10a) which demonstrated lower MIC values against S. aureus and S. epidermidis (1 μg/ml) and lower cytotoxicity on HEK-293 cells (CC50 = 200 μg/ml). Compound 10a had no significant mutagenic and genotoxic effects and was selected for further evaluation. It should be noted that all bis-phosphonium salt based on pyridoxine were much more toxic than vancomycin. © 2013 Elsevier Ltd. All rights reserved. | |
dc.relation.ispartofseries | Bioorganic and Medicinal Chemistry | |
dc.subject | Antibacterial activity | |
dc.subject | Lipophilicity | |
dc.subject | Pyridoxine | |
dc.subject | Quaternary phosphonium salts | |
dc.subject | Structure-activity relationship | |
dc.title | Bis-phosphonium salts of pyridoxine: The relationship between structure and antibacterial activity | |
dc.type | Article | |
dc.relation.ispartofseries-issue | 23 | |
dc.relation.ispartofseries-volume | 21 | |
dc.collection | Публикации сотрудников КФУ | |
dc.relation.startpage | 7330 | |
dc.source.id | SCOPUS09680896-2013-21-23-SID84886954100 |