Nature-inspired Novel Quaternary Ammonium Compounds: Synthesis, Antibacterial and Antibiofilm Activity

被引:0
作者
Muzychka, Liubov [1 ]
Hodyna, Diana [1 ]
Metelytsia, Larysa [1 ]
Smolii, Oleg [1 ]
机构
[1] Natl Acad Sci Ukraine, VP Kukhar Inst Bioorgan Chem & Petrochem, Dept Chem Nat Cpds, 1 Academician Kukhar Str, UA-02094 Kyiv, Ukraine
基金
新加坡国家研究基金会;
关键词
Natural products; Quaternary ammonium salts; Alkylation; Biological activity; Antibiofilm;
D O I
10.1002/cmdc.202400807
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Inspired by marine compounds isolated from sponges and the increased need for new effective antimicrobials, novel quaternary ammonium compounds with long alkyl chains (C8-C12) were designed and synthesized. Antibacterial and antibiofilm activity of new compounds was evaluated against six microbial strains (S. aureus, E. coli, and P. aeruginosa). All synthesized ammonium salts displayed antibacterial activity with MIC values ranging from 5.0 to 25.0 mu g/mL. In addition, most compounds showed strong inhibition of biofilm formation of S. aureus ATCC 25923, P. aeruginosa PA01, and colistin-resistant P. aeruginosa (CRPA) at a concentration of 5.0 mu g/mL. Ammonium salt 3 showed 100 % inhibitory activity against all tested bacterial biofilms except that of colistin-resistant S. aureus (CRSA).
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页数:5
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共 27 条
[1]   Microbial Biofilms: Applications, Clinical Consequences, and Alternative Therapies [J].
Ali, Asghar ;
Zahra, Andaleeb ;
Kamthan, Mohan ;
Husain, Fohad Mabood ;
Albalawi, Thamer ;
Zubair, Mohammad ;
Alatawy, Roba ;
Abid, Mohammad ;
Noorani, Md Salik .
MICROORGANISMS, 2023, 11 (08)
[2]  
Allen R. A., 2023, CHEMMEDCHEM, V18
[3]   Parallel synthesis of a bis-triazoles library as psammaplin A analogues: A new wave of antibiofilm compounds? [J].
Andjouh, Sofyane ;
Blache, Yves .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2019, 29 (04) :614-618
[4]   PHYSIOLOGICALLY ACTIVE SUBSTANCES FROM MARINE SPONGES .5. ISOLATION OF PHYSIOLOGICALLY ACTIVE COMPOUNDS FROM SPONGE VERONGIA-ARCHERI [J].
CHIB, JS ;
STEMPIEN, MF ;
MIERZWA, RA ;
RUGGIERI, GD ;
NIGRELLI, RF .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1978, 67 (02) :264-265
[5]   Antibacterial quaternary ammonium agents: Chemical diversity and biological mechanism [J].
Dan, Wenjia ;
Gao, Jixiang ;
Qi, Xiaohui ;
Wang, Junru ;
Dai, Jiangkun .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2022, 243
[6]   Marine natural products and their synthetic analogs as promising antibiofilm agents for antibiotics discovery and development [J].
Deng, Yueting ;
Liu, Yang ;
Li, Juan ;
Wang, Xiao ;
He, Shan ;
Yan, Xiaojun ;
Shi, Yutong ;
Zhang, Weiyan ;
Ding, Lijian .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2022, 239
[7]   Advances in the Synthesis of Biologically Active Quaternary Ammonium Compounds [J].
Fedorowicz, Joanna ;
Saczewski, Jaroslaw .
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2024, 25 (09)
[8]   Bioactive Brominated Metabolites from the Natural Habitat and Tank-Maintained Cuttings of the Jamaican Sponge Aplysina fistularis [J].
Gallimore, Winklet A. .
CHEMISTRY & BIODIVERSITY, 2013, 10 (06) :1055-1060
[9]   Role of small molecules and nanoparticles in effective inhibition of microbial biofilms: A ray of hope in combating microbial resistance [J].
Gattu, Rohith ;
Ramesh, Sanjay S. ;
Ramesh, Suhas .
MICROBIAL PATHOGENESIS, 2024, 188
[10]   Glycodiversification of gentamicins through in vivo glycosyltransferase swapping enabled the creation of novel hybrid aminoglycoside antibiotics with potent activity and low ototoxicity [J].
Jian, Xinyun ;
Wang, Cheng ;
Wu, Shijuan ;
Sun, Guo ;
Huang, Chuan ;
Qiu, Chengbing ;
Liu, Yuanzheng ;
Leadlay, Peter F. ;
Liu, Dong ;
Deng, Zixin ;
Zhou, Fuling ;
Sun, Yuhui .
ACTA PHARMACEUTICA SINICA B, 2024, 14 (09) :4149-4163