Synthesis and Antimicrobial Activity of Quaternary Ammonium Silane Coupling Agents

被引:12
|
作者
Yoshino, Norio [1 ,2 ]
Sugaya, Shigenori [1 ]
Nakamura, Toshimitsu [1 ]
Yamaguchi, Yoh-hei [1 ]
Kondo, Yukishige [1 ,2 ]
Kawada, Kazuo [3 ]
Teranaka, Toshio [4 ]
机构
[1] Tokyo Univ Sci, Fac Engn, Shinjuku Ku, Tokyo 1620826, Japan
[2] Tokyo Univ Sci, Inst Colloid & Interface Sci, Shinjuku Ku, Tokyo 1628601, Japan
[3] Kitasato Univ, Fac Sci, Minami Ku, Kanagawa 2520373, Japan
[4] Kanagawa Dent Coll, Dept Oral Med, Div Restorat Dent, Kanagawa 2388580, Japan
关键词
silane coupling agents; antimicrobial activity; surface modification; quaternary ammonium salts; minimum inhibitory concentrations; POLYMERIC PHOSPHONIUM SALTS; SURFACE MODIFICATION; FLUOROCARBON CHAIN; ANTIBACTERIAL ACTIVITY; CATIONIC BIOCIDES; COMPOSITES; GLASS;
D O I
10.5650/jos.60.429
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Fourteen novel silane coupling agents with a quaternary ammonium group introduced into the molecule, [CH2=CHCH2N+(CH3)(CnH2n+1)(CH2)(3)Si(OCH3)(3)]X- (n-X, n=10-18, X=Cl, Br, or I), were synthesized with the aim of using these agents to make material surfaces antimicrobial for a long period of time. Measurements of the minimum inhibitory concentrations (MIC) against 12 kinds of fungi and bacteria revealed that the coupling agent with a C-10 alkyl chain and Cl- or Br- counter-ion (10-Cl or 10-Br) has the highest antimicrobial activity among the n-X agents synthesized, but 14-Cl and 14-Br showed the highest activity on a modified porcelain plate.
引用
收藏
页码:429 / 438
页数:10
相关论文
共 50 条
  • [21] New quaternary ammonium pyridoxine derivatives: synthesis and antibacterial activity
    Sergey V. Sapozhnikov
    Nikita V. Shtyrlin
    Airat R. Kayumov
    Alina E. Zamaldinova
    Alfiya G. Iksanova
    Еlena V. Nikitina
    Еlena S. Krylova
    Denis Yu. Grishaev
    Konstantin V. Balakin
    Yurii G. Shtyrlin
    Medicinal Chemistry Research, 2017, 26 : 3188 - 3202
  • [22] Synthesis and Antibacterial Activity of Novel Quaternary Ammonium Pyridoxine Derivatives
    Shtyrlin, Nikita V.
    Sapozhnikov, Sergey V.
    Koshkin, Sergey A.
    Iksanova, Alfiya G.
    Sabirov, Arthur H.
    Kayumov, Airat R.
    Nureeva, Aliya A.
    Zeldi, Marina I.
    Shtyrlin, Yurii G.
    MEDICINAL CHEMISTRY, 2015, 11 (07) : 656 - 665
  • [23] Controllable synthesis and antimicrobial activities of acrylate polymers containing quaternary ammonium salts
    Zhong, Weiqiang
    Dong, Chenyun
    Liuyang, Runqi
    Guo, Qizhi
    Zeng, Hong
    Lin, Yaling
    Zhang, Anqiang
    REACTIVE & FUNCTIONAL POLYMERS, 2017, 121 : 110 - 118
  • [24] Biological Activity of Quaternary Ammonium Salts and Their Derivatives
    Kwasniewska, Dobrawa
    Chen, Ying-Lien
    Wieczorek, Daria
    PATHOGENS, 2020, 9 (06): : 1 - 12
  • [25] Antimicrobial activity and cytotoxicity of novel quaternary ammonium and phosphonium salts
    Nunes, Barbara
    Cagide, Fernando
    Borges, Fernanda
    Simoes, Manuel
    JOURNAL OF MOLECULAR LIQUIDS, 2024, 401
  • [26] Stereoisomeric effect on antimicrobial activity of a series of quaternary ammonium salts
    Gregan, F
    Oremusova, J
    Remko, M
    Gregan, J
    Mlynarcik, D
    FARMACO, 1998, 53 (01): : 41 - 48
  • [27] Synthesis and Biological Activity of Quaternary Ammonium Salt-Type Agents Containing Cholesterol and Terpenes
    Novotna, Eva
    Waisser, Karel
    Kunes, Jiri
    Palat, Karel
    Buchta, Vladimir
    Stolarikova, Jirina
    Beckert, Rainer
    Wsol, Vladimir
    ARCHIV DER PHARMAZIE, 2014, 347 (06) : 381 - 386
  • [28] Green Accelerated Synthesis, Antimicrobial Activity and Seed Germination Test of Quaternary Ammonium Salts of 1,2-bis(4-pyridyl)ethane
    Tabacaru, Aurel
    Botezatu, Andreea Veronica Dediu
    Horincar, Georgiana
    Furdui, Bianca
    Dinica, Rodica Mihaela
    MOLECULES, 2019, 24 (13):
  • [29] Effect of quaternary ammonium silane coating on adhesive immobilization of industrial yeasts
    Kregiel, Dorota
    Berlowska, Joanna
    CHEMICAL PAPERS, 2014, 68 (03) : 308 - 315
  • [30] Cholic Acid-Derived Facial Surfactants with Long Side-Chain Quaternary Ammonium: Synthesis and Antimicrobial Activity Study
    Zhou, Lanxiang
    Li, Yang
    Li, Shuangshuang
    Shen, Xinliang
    Wang, Cunde
    JOURNAL OF SURFACTANTS AND DETERGENTS, 2016, 19 (04) : 803 - 811