Abstract:
One interesting field of research in the view of developing novel surfactants for pharmaceutical and cosmetic applications is the design of amphiphiles showing further bioactive properties in addition to those commonly displayed by surface-active compounds. We propose here the chemical synthesis, and characterization of 1-o-tolyl alkyl biguanide derivatives, having different lengths of the hydrocarbon chain (C3, C6, and C10), and showing surface active and antibacterial/disinfectant activities toward both Gram-positive and Gram-negative bacteria. Both surface active properties in terms of critical micelle concentration (CMC) and surface tension at CMC (γCMC), as well as the antimicrobial activity in terms of minimum inhibitory concentrations (MICs), were strongly dependent on the length of the hydrocarbon chain. Particularly, the C6 and C10 derivatives have a good ability to decrease surface tension (γCMC <40 mN/m) at low concentrations (CMC < 12 mM) and a satisfactory antibacterial effect (MIC values between 0.230 and 0.012 mM against S. aureus strains and between 0.910 and 0.190 against P.aeruginosa strains). Interestingly, these compounds showed a disinfectant activity at the tested concentrations that was comparable to that of the reference compound chlorhexidine digluconate. All these results support the possible use of these amphiphilic compounds as antibacterial agents and disinfectants in pharmaceutical or cosmetic formulations.
摘要:
从开发用于药物和化妆品应用的新型表面活性剂的角度来看,一个令人感兴趣的研究领域是除了通常由表面活性化合物显示的那些之外,还显示出进一步的生物活性性质的两亲物的设计。我们在这里提出化学合成,1-邻甲苯基烷基双胍衍生物的表征,具有不同长度的烃链(C3、C6和C10),并显示对革兰氏阳性和革兰氏阴性细菌的表面活性和抗菌/消毒剂活性。临界胶束浓度(CMC)和CMC表面张力(γCMC)方面的表面活性特性,以及最小抑制浓度(MIC)方面的抗菌活性,强烈依赖于烃链的长度。特别是,C6和C10衍生物在低浓度(CMC<12mM)下具有良好的降低表面张力的能力(γCMC<40mN/m)和令人满意的抗菌效果(对金黄色葡萄球菌菌株的MIC值在0.230和0.012mM之间,对铜绿假单胞菌菌株的MIC值在0.910和0.190之间)。有趣的是,这些化合物在测试浓度下显示出与参考化合物二葡萄糖酸氯己定相当的消毒活性。所有这些结果支持这些两亲性化合物在药物或化妆品制剂中作为抗菌剂和消毒剂的可能用途。