Synthesis and Antibacterial Activity of Novel Quaternary Ammonium Pyridoxine Derivatives

被引:27
作者
Shtyrlin, Nikita V. [1 ]
Sapozhnikov, Sergey V. [1 ]
Koshkin, Sergey A. [1 ]
Iksanova, Alfiya G. [1 ]
Sabirov, Arthur H. [1 ]
Kayumov, Airat R. [1 ]
Nureeva, Aliya A. [1 ]
Zeldi, Marina I. [1 ]
Shtyrlin, Yurii G. [1 ]
机构
[1] Kazan Fed Univ, Res & Educ Ctr Pharm, Kazan 420008, Russia
关键词
Antibacterial activity; quaternary ammonium salts; pyridoxine; cytotoxicity; genotoxicity; ANTIMICROBIAL RESISTANCE; PHOSPHONIUM SALTS; ANTISEPTICS; INFECTIONS; BACTERIAL;
D O I
10.2174/1573406411666150504122930
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of 26 quaternary ammonium pyridoxine derivatives were synthesized and their cytotoxicity and antibacterial activities against clinically relevant bacterial strains were tested in vitro. The antibacterial activity of mono-ammonium salts increased with the rise of the lipophilicity and compound 3,3,5-trimethyl-8,8-dioctyl-1,7,8,9-tetrahydro-[1,3] dioxino[5,4-d] pyrrolo[3,4-b] pyridin-8-ium chloride (2d) reaches a maximum among them. Bis-ammonium salt of pyridoxine 4 with two dimethyloctylamine groups also demonstrated high antibacterial activity despite lower lipophilicity. The results of MTT assay indicated that HEK 293 cells were more sensitive than HSF to quaternary ammonium pyridoxine derivatives. Compounds 2d and 4 did not induce the damage of the DNA and might be of interest in the development of new antimicrobials.
引用
收藏
页码:656 / 665
页数:10
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