Synthesis, surface-active properties, and antimicrobial activities of new double-chain gemini surfactants.
A novel series of neutral and cationic dimeric surfactants were prepared involving ketalization reaction, Williamson etherification, and regioselective oxirane ring opening with primary and tertiary alkyl amines. The critical micelle concentration (CMC), effectiveness of surface tension reduction (gamma(CMC)), surface excess concentration (Gamma), and area per molecule at the interface (A) were determined and values indicate that the cationic series is characterized by good surface-active and self-aggregation properties. For the first time, we reported the antimicrobial activities against representative bacteria and fungi for dimeric compounds. The antimicrobial activity was found to be dependent on the target microorganism (Gram-positive bacteria > fungi > Gram-negative bacteria), as well as both the neutral or ionic nature (cationic > neutral) and alkyl chain length (di-C(12) > di-C(18) > di-C(8)) of the compounds. The cationic di-C(12) derivative was found to have equipotent activity to that of benzalkonium chloride (BAC) used as standard.
Murguía
Marcelo C
MC
Laboratorio de Química Fina. Instituto de Desarrollo Tecnológico para la Industria Química (INTEC), Universidad Nacional del Litoral (U.N.L.), Santa Fe, Argentina. mmurguia@santafe-conicet.gov.ar
Vaillard
Victoria A
VA
Sánchez
Victoria G
VG
Conza
José Di
JD
Grau
Ricardo J
RJ
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D004058:Diffusion / Q000187:drug effects; D019281:Dimerization; D005658:Fungi / Q000187:drug effects; D006863:Hydrogen-Ion Concentration / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D013499:Surface Properties / Q000187:drug effects; D013500:Surface Tension / Q000187:drug effects; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D013501:Surface-Active Agents