Synthesis and Antibacterial Activity of Novel Amido-Amine-Based Cationic Gemini Surfactants

被引:54
作者
Ghumare, Anant K. [1 ]
Pawar, Balu V. [1 ]
Bhagwat, Sunil S. [1 ]
机构
[1] Inst Chem Technol Autonomous, Dept Chem Engn, Bombay 400019, Maharashtra, India
关键词
Cationic gemini surfactants; Amido-amine; Critical micelle concentration; Antibacterial agents; QUATERNARY AMMONIUM-COMPOUNDS; RESISTANCE; AGGREGATION; ENVIRONMENT; ARGININE;
D O I
10.1007/s11743-012-1406-4
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A series of novel cationic gemini surfactants were synthesized from corresponding amido-amines in a single step reaction. The amido-amines were obtained from long chain carboxylic acids and 3-N,N-dimethylamino-1-propyl-amine with excellent isolated yield (up to 95 %). All the synthesized quaternary ammonium compounds (QACs) were further investigated for surface active properties. The critical micelle concentration (CMC) and the effectiveness of surface tension reduction were determined. The surface tension measurements of newly synthesized gemini surfactants showed good water solubility, and low CMC values, had great efficiency in lowering the surface tension and a strong adsorption at the air/water interface than the corresponding monomeric surfactants. Further, the antibacterial activity of the synthesized QACs against both Gram-positive and Gram-negative bacteria was also investigated.
引用
收藏
页码:85 / 93
页数:9
相关论文
共 24 条
  • [1] Novel antibacterial agents for the treatment of serious Gram-positive infections
    Abbanat, D
    Macielag, M
    Bush, K
    [J]. EXPERT OPINION ON INVESTIGATIONAL DRUGS, 2003, 12 (03) : 379 - 399
  • [2] Transfection mediated by gemini surfactants: Engineered escape from the endosomal compartment
    Bell, PC
    Bergsma, M
    Dolbnya, IP
    Bras, W
    Stuart, MCA
    Rowan, AE
    Feiters, MC
    Engberts, JBFN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (06) : 1551 - 1558
  • [3] CHRISTINE HF, 1986, ANTIMICROB AGENTS CH, V29, P386, DOI DOI 10.1007/S11743-012-1406-4
  • [4] Structure-based classification of antibacterial activity
    Cronin, MTD
    Aptula, AO
    Dearden, JC
    Duffy, JC
    Netzeva, TI
    Patel, H
    Rowe, PH
    Schultz, TW
    Wortht, AP
    Voutzoulidis, K
    Schüürmann, G
    [J]. JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, 2002, 42 (04): : 869 - 878
  • [5] SYNTHESIS, SURFACE-ACTIVE PROPERTIES AND ANTIMICROBIAL ACTIVITY OF NEW BIS QUATERNARY AMMONIUM-COMPOUNDS
    DIZ, M
    MANRESA, A
    PINAZO, A
    ERRA, P
    INFANTE, MR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (08): : 1871 - 1876
  • [6] Legal issues associated with antimicrobial drug resistance
    Fidler, DP
    [J]. EMERGING INFECTIOUS DISEASES, 1998, 4 (02) : 169 - 177
  • [7] Sugar-based tertiary amino gemini surfactants with a vesicle-to-micelle transition in the endosomal pH range mediate efficient transfection in vitro
    Fielden, ML
    Perrin, C
    Kremer, A
    Bergsma, M
    Stuart, MC
    Camilleri, P
    Engberts, JBFN
    [J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 2001, 268 (05): : 1269 - 1279
  • [8] Biologically active bisquaternary ammonium chlorides:: Physico-chemical properties of long chain amphiphiles and their evaluation as non-viral vectors for gene delivery
    Fisicaro, E
    Compari, C
    Duce, E
    Donofrio, G
    Rózycka-Roszak, B
    Wozniak, E
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 2005, 1722 (02): : 224 - 233
  • [9] Fate and effect of monoalkyl quaternary ammonium surfactants in the aquatic environment
    García, MT
    Ribosa, I
    Guindulain, T
    Sánchez-Leal, J
    Vives-Rego, J
    [J]. ENVIRONMENTAL POLLUTION, 2001, 111 (01) : 169 - 175
  • [10] Synthesis and properties of novel tetraalkyl cationic lipids
    Gaucheron, J
    Wong, T
    Wong, EF
    Maurer, N
    Cullis, PR
    [J]. BIOCONJUGATE CHEMISTRY, 2002, 13 (03) : 671 - 675