Abstract
Twenty-one novel 5-phenyl-1,3,4-oxadiazole-2-thiol (POT) substituted N-hydroxyethyl quaternary ammonium salts (6a-g, 7a-g, 8a-g) were prepared and characterized by FTIR, NMR, and elemental analysis. Compounds 6a, 6c, and 8a were confirmed by X-ray single-crystal diffraction. They display the unsurpassed antibacterial activity against Staphylococcus aureus, α-H-tococcus, Escherichia coli, P. aeruginosa, Proteus vulgaris, Canidia Albicans, especially 6g, 7g, 8g with dodecyl group. Compounds 8a-d with N,N-dihydroxyethyl and POT groups display unsurpassed antibacterial activity and non-toxicity. The structure-activity relationships indicate that POT and flexible dihydroxyethyl group in QAS are necessary for antibacterial activity and cytotoxicity. SEM and TEM images of E. coli morphologies of 8d show the antibacterial agents can adhere to membrane surfaces to inhibit bacterial growth by disrupting peptidoglycan formation and releasing bacterial cytoplasm from cell membranes.
References
Nov 1, 1989·Journal of Bacteriology·B L de JongeN Nanninga
May 5, 1970·Biochimica Et Biophysica Acta·V Aries, M J Hill
Feb 1, 1994·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·M MakinoH Zenda
Jan 9, 1999·Clinical Microbiology Reviews·G McDonnell, A D Russell
Mar 28, 2002·Applied and Environmental Microbiology·A UlteeR Moezelaar
Feb 1, 1956·The Journal of Pharmacy and Pharmacology·M BABBSE P TAYLOR
May 9, 2009·Naunyn-Schmiedeberg's Archives of Pharmacology·Chaoyun WangXianghua Xiao
Feb 2, 2011·Biomacromolecules·Souvik ChakrabartyKenneth J Wynne
Nov 25, 2011·ChemMedChem·Maximilian TischerUlrike Holzgrabe
Jan 4, 2012·Chemical Biology & Drug Design·Nisha AggarwalJitender Mohan Khurana
Jan 27, 2012·Dental Materials Journal·Sai MaShigeyuki Ebisu
Jun 5, 2012·Acta Biomaterialia·Shi-qiang GongFranklin R Tay
Aug 8, 2013·Biochemical and Biophysical Research Communications·Hope T BadawyAmy Milsted
Nov 19, 2013·FEMS Microbiology Letters·Ewa ObłąkEwa Dworniczek
Sep 13, 2014·Chemical Biology & Drug Design·Wen-Shuai LiuRong-Jun Qu
Dec 30, 2015·International Journal of Biological Macromolecules·Chun-Hua WangFeng Zhao
Citations
Nov 18, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Xianrui XieChunhua Wang
Jul 3, 2021·International Journal of Molecular Sciences·Teresa Glomb, Piotr Świątek
Sep 19, 2020·ACS Nano·Wenshuai LiuWeiwei Wang
Sep 3, 2021·Advanced Healthcare Materials·Wenshuai LiuWeiwei Wang
Nov 30, 2021·ACS Omega·Gang YuJian Wu