Synthesis and antibacterial properties of novel hydrolyzable cationic amphiphiles. Incorporation of multiple head groups leads to impressive antibacterial activity
Synthesis and antibacterial properties of novel hydrolyzable cationic amphiphiles. Incorporation of multiple head groups leads to impressive antibacterial activity
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DOI：
10.1021/jm049106l
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发表时间：
2005-06-02
影响因子：
7.3
通讯作者：
Bhattacharya, S
中科院分区：
文献类型：
--
作者：
Haldar, J;Kondaiah, P;Bhattacharya, S
合成了两组新颖的多头阳离子两亲物，它们分别带有一个、两个和三个三甲基铵头基（T1、T2和T3）和吡啶鎓头基（P1、P2和P3），并测试了它们对革兰氏阳性菌和革兰氏阴性菌的抗菌活性。这些两亲物中的多阳离子头基通过易切断的酯型键共价连接。与已知的表面活性，不可水解的化合物十六烷基三甲基溴化铵（CTAB）和十六烷基溴化吡啶（CPB）的结果进行了比较。新的单头两亲物（T1和P1）的杀伤效果低于CTAB和CPB，但随着两亲物中头基数目的增加，两组化合物的杀伤效果增加。结果表明，在所有的两亲分子中，具有三个头基的两亲分子（T3和P3）的活性最高，而两亲分子P1对两种细菌的杀灭效果都很差。多头吡啶盐两亲物比它们的三甲基铵对应物更活性。用多头两亲物杀死细菌所需的时间明显少于单头两亲物。由于存在可裂解的酯部分，这些新的两亲物在生理条件下自发水解。这种性质使它们易于代谢，因此有可能成为食品和身体表面的上级消毒剂和防腐剂。
Two sets of novel multiheaded cationic amphiphiles bearing one, two, and three trimethylammonium headgroups T1, T2, and T3) and pyridinium headgroups (P1, P2, and P3), have been synthesized and tested for antimicrobial activities against both Gram-positive and Gram-negative bacteria. The multicationic headgroups in these amphiphiles were attached covalently via scissile ester-type linkages. The results were compared with those for known surface-active, nonhydrolyzable compounds cetyltrimethylammonium bromide (CTAB) and cetylpyridinium bromide (CPB). The killing effects of the new single-headed amphiphiles (T1 and P1) were lower than those of CTAB and CPB, but with an increase in the number of headgroups in the amphiphiles, the killing effects increased for both sets of compounds. It was found that amphiphiles with triple headgroups (T3 and P3) were most active among all the amphiphiles, whereas amphiphile P1 had a very poor killing effect on both types of bacteria. The multiheaded pyridinium amphiphiles were more active compared to their trimethylammonium counterparts. The time needed to kill bacteria with multiheaded amphiphiles was significantly less than that of single-headed amphiphiles. Owing to the presence of a cleavable ester moiety, these new amphiphiles are hydrolyzed spontaneously at physiological conditions. This property enables them to be readily metabolized and therefore have the potential to be superior disinfectants and antiseptics for food and body surfaces.