Syntheses and antimicrobial activities of a series of new bis-quaternary ammonium compounds

被引:114
|
作者
Kourai, Hiroki [1 ]
Yabuhara, Tadao [1 ]
Shirai, Akihiro [1 ]
Maeda, Takuya [1 ]
Nagamune, Hideki [1 ]
机构
[1] Univ Tokushima, Fac Engn, Dept Biol Sci & Technol, Tokushima 7708506, Japan
关键词
synthesis; bis-quaternary ammonium compounds; antimicrobial activity;
D O I
10.1016/j.ejmech.2005.10.021
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of new bis-quatemary ammonium compounds (bis-QACs), 4,4'-(2,9-dioxadecane) bis(I-alkylpyridinium bromide)s, 3,3'-(2,9-dioxadecane)bis(1-alkylpyridinium bromide)s and 3,3'-(2,7-dioxaoctane)bis(1-decylpyridinium bromide) was synthesized. The compounds were evaluated by their activities against bacteria, molds and yeasts; the activities were expressed as the minimum inhibitory concentrations (MIC) and/or the minimum bactericidal concentrations (MBC). Compound 4,4'-(2,9-dioxadecane) bis(1-decylpyridinium bromide) had MIC values which exceeded those of benzalkoniumchloride and thiabendazole. It was in vitro active against a broad spectrum of Gram-negative and Gram-positive bacteria, against yeasts and some molds, it had high solubility and thermal decomposition temperature. The relationships between structure and biological activity of the tested bis-QACs are discussed. (c) 2006 Elsevier SAS. All rights reserved.
引用
收藏
页码:437 / 444
页数:8
相关论文
共 50 条
  • [21] Biocidal Polymers: Synthesis, Characterization and Antimicrobial Activity of Bis-Quaternary Onium Salts of Poly(aspartate-co-succinimide)
    El-Newehy, Mohamed H.
    Moydeen, A. Meera
    Aldalbahi, Ali K.
    Thamer, Badr M.
    Mahmoud, Yehia A. -G.
    El-Hamshary, Hany
    POLYMERS, 2021, 13 (01) : 1 - 13
  • [22] Synthesis and characterization of novel polymerizable bis-quaternary ammonium dimethacrylate monomers with antibacterial activity as an efficient adhesive system for dental restoration
    Manouchehri, Farzaneh
    Sadeghi, Bahareh
    Najafi, Farhood
    Mosslemin, Mohammad Hossein
    Niakan, Mohammad
    POLYMER BULLETIN, 2019, 76 (03) : 1295 - 1315
  • [23] Discovery of novel quaternary ammonium compounds based on quinuclidine-3-ol as new potential antimicrobial candidates
    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
  • [24] Antimicrobial activities of polymeric quaternary ammonium salts from poly(glycidyl methacrylate)s
    Liang, Zhixiang
    Zhu, Mingran
    Yang, Ying-Wei
    Gao, Hui
    POLYMERS FOR ADVANCED TECHNOLOGIES, 2014, 25 (01) : 117 - 122
  • [25] Quaternary Ammonium Salts of Cationic Lipopeptides with Lysine Residues - Synthesis, Antimicrobial, Hemolytic and Cytotoxic Activities
    Sikora, Karol
    Jedrzejczak, Jakub
    Bauer, Marta
    Neubauer, Damian
    Jaskiewicz, Maciej
    Szarynska, Magdalena
    PROBIOTICS AND ANTIMICROBIAL PROTEINS, 2023, 15 (06) : 1465 - 1483
  • [26] Synthesis and antimicrobial activities of polysiloxane-containing quaternary ammonium salts on bacteria and phytopathogenic fungi
    Lin, Yaling
    Liu, Qiongqiong
    Cheng, Liujun
    Lei, Yufeng
    Zhang, Anqiang
    REACTIVE & FUNCTIONAL POLYMERS, 2014, 85 : 36 - 44
  • [27] Quaternary Ammonium Salts of Cationic Lipopeptides with Lysine Residues — Synthesis, Antimicrobial, Hemolytic and Cytotoxic Activities
    Karol Sikora
    Jakub Jędrzejczak
    Marta Bauer
    Damian Neubauer
    Maciej Jaśkiewicz
    Magdalena Szaryńska
    Probiotics and Antimicrobial Proteins, 2023, 15 : 1465 - 1483
  • [28] Evaluation of Antimicrobial Efficiency of New Polymers Comprised by Covalently Attached and/or Electrostatically Bound Bacteriostatic Species, Based on Quaternary Ammonium Compounds
    Kougia, Efstathia
    Tselepi, Maria
    Vasilopoulos, Gavriil
    Lainioti, Georgia Ch.
    Koromilas, Nikos D.
    Druvari, Denisa
    Bokias, Georgios
    Vantarakis, Apostolos
    Kallitsis, Joannis K.
    MOLECULES, 2015, 20 (12) : 21313 - 21327
  • [29] A novel approach to mixed micelles formation: study the interactions between bis-quaternary ammonium salts and nonionic surfactant Triton X-100
    Przybyl, Patrycja
    Wojcieszak, Marta
    Kaczmarek, Damian Krystian
    Jankowski, Damian
    Materna, Katarzyna
    TENSIDE SURFACTANTS DETERGENTS, 2024, 61 (01) : 1 - 9
  • [30] Syntheses and Herbicidal Activities of New Methylsulfonyl Compounds with Pyrazol Group
    Wen, Yanpeng
    Zhang, Shuang
    Hou, Guangfeng
    Yu, Yinghui
    Gao, Jinsheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (03) : 642 - 647