Antibacterial quaternary ammonium agents: Chemical diversity and biological mechanism

被引:70
作者
Dan, Wenjia [1 ]
Gao, Jixiang [1 ]
Qi, Xiaohui [1 ]
Wang, Junru [2 ,4 ]
Dai, Jiangkun [1 ,3 ]
机构
[1] Weifang Med Univ, Sch Life Sci & Technol, Weifang, Shandong, Peoples R China
[2] Northwest A&F Univ, Coll Chem & Pharm, Xianyang, Shaanxi, Peoples R China
[3] Weifang Med Univ, Sch Life Sci & Technol, Room 21408,Bldg Minxing,Baotong West St, Weifang, Peoples R China
[4] Northwest A&F Univ, Coll Chem & Pharm, Room C206,Bldg Sci, Yangling, Shaanxi, Peoples R China
基金
中国国家自然科学基金;
关键词
Quaternary ammonium compounds; Antibacterial; Structure -activity relationships; Mechanism; ANTIMICROBIAL ACTIVITY; SMALL MOLECULES; IN-VITRO; DERIVATIVES; BACTERIAL; COMPOUND; ANALOGS; BROAD; ANTIBIOTICS; AMPHIPHILES;
D O I
10.1016/j.ejmech.2022.114765
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Bacterial infections have seriously threatened public health especially with the increasing resistance and the clifflike decline of the number of newly approved antibacterial agents. Quaternary ammonium compounds (QACs) possess potent medicinal properties with 95 successfully marketed drugs, which also have a long history as antibacterial agents. In this review, we summarize the chemical diversity of antibacterial QACs, divided into chain-like and aromatic ring, reported over the past decade (2012 to mid-2022). Additionally, the structureactivity relationships, mainly covering hydrophobicity, charges and skeleton features, are discussed. In the cases where sufficient information is available, antibacterial mechanisms including biofilm, cell membrane, and intracellular targets are presented. It is hoped that this review will provide sufficient information for medicinal chemists to discover the new generation of antibacterial agents based on QACs.
引用
收藏
页数:12
相关论文
共 100 条
[1]   The Development of Next-Generation Pyridinium-Based multiQAC Antiseptics [J].
Al-Khalifa, Saleh E. ;
Jennings, Megan C. ;
Wuest, William M. ;
Minbiole, Kevin P. C. .
CHEMMEDCHEM, 2017, 12 (04) :280-283
[2]   Synthesis and characterization of pyridine -based organic salts: Their antibacterial, antibiofilm and wound healing activities [J].
Ali, Imdad ;
Burki, Samiullah ;
El-Haj, Babiker M. ;
Shafiullah ;
Parveen, Samina ;
Nadeem, Hilal Sahin ;
Nadeem, Said ;
Shah, Muhammad Raza .
BIOORGANIC CHEMISTRY, 2020, 100
[3]   Cefiderocol (S-649266), A new siderophore cephalosporin exhibiting potent activities against Pseudomonas aeruginosa and other gram-negative pathogens including multi-drug resistant bacteria: Structure activity relationship [J].
Aoki, Toshiaki ;
Yoshizawa, Hidenori ;
Yamawaki, Kenji ;
Yokoo, Katsuki ;
Sato, Jun ;
Hisakawa, Shinya ;
Hasegawa, Yasushi ;
Kusano, Hiroki ;
Sano, Masayuki ;
Sugimoto, Hideki ;
Nishitani, Yasuhiro ;
Sato, Takafumi ;
Tsuji, Masakatsu ;
Nakamura, Rio ;
Nishikawa, Toru ;
Yamano, Yoshinori .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 155 :847-868
[4]   A polymeric approach toward resistance-resistant antimicrobial agent with dual-selective mechanisms of action [J].
Bai, Silei ;
Wang, Jianxue ;
Yang, Kailing ;
Zhou, Calling ;
Xu, Yangfan ;
Song, Junfeng ;
Gu, Yuanxin ;
Chen, Zheng ;
Wang, Min ;
Shoen, Carolyn ;
Andrade, Brenda ;
Cynamon, Michael ;
Zhou, Kai ;
Wang, Hui ;
Cai, Qingyun ;
Oldfield, Eric ;
Zimmerman, Steven C. ;
Bai, Yugang ;
Feng, Xinxin .
SCIENCE ADVANCES, 2021, 7 (05)
[5]   Antimicrobial peptide-inspired NH125 analogues: bacterial and fungal biofilm-eradicating agents and rapid killers of MRSA persisters [J].
Basak, Akash ;
Abouelhassan, Yasmeen ;
Zuo, Ran ;
Yousaf, Hussain ;
Ding, Yousong ;
Huigens, Robert W., III .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (26) :5503-5512
[6]   Discovery of novel quaternary ammonium compounds based on quinuclidine-3-ol as new potential antimicrobial candidates [J].
Bazina, Linda ;
Maravic, Ana ;
Krce, Lucija ;
Soldo, Barbara ;
Odzak, Renata ;
Popovic, Viljemka Butevic ;
Aviani, Ivica ;
Primozic, Ines ;
Sprung, Matilda .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 163 :626-635
[7]   Asymmetric trisalkylamine cyclopropenium derivatives with antimicrobial activity [J].
Belay, Chen ;
Steinmann, Noam Y. ;
Campos, Luis M. ;
Dzikowski, Ron ;
Golenser, Jacob ;
Domb, Abraham J. .
BIOORGANIC CHEMISTRY, 2020, 102
[8]   TMEDA-derived biscationic amphiphiles: An economical preparation of potent antibacterial agents [J].
Black, Jacob W. ;
Jennings, Megan C. ;
Azarewicz, Julianne ;
Paniak, Thomas J. ;
Grenier, Melissa C. ;
Wuest, William M. ;
Minbiole, Kevin P. C. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (01) :99-102
[9]  
Boethling R.S., 1994, CATIONIC SURFACTANTS, P102
[10]   Ammonium-Charged Sterically Hindered Phenols with Antioxidant and Selective Anti-Gram-Positive Bacterial Activity [J].
Bogdanov, Andrei V. ;
Iskhakova, Kamilla R. ;
Voloshina, Alexandra D. ;
Sapunova, Anastasia S. ;
Kulik, Natalia V. ;
Terekhova, Natalia V. ;
Arsenyev, Maxim V. ;
Ziyatdinova, Guzel K. ;
Bukharov, Sergey V. .
CHEMISTRY & BIODIVERSITY, 2020, 17 (05)