Novel gemini pyridinium surfactants: synthesis and study of their surface activity, DNA binding, and cytotoxicity.

ABSTRACT

New pyridinium gemini amphiphiles having ethane-1,2-dithiol spacer have been synthesized by regioselective electrophilic cobromination of alpha-olefins. Ethane-1,2-dithiol (1) and N-bromosuccinimide (6) on reaction with alpha-olefins (dodecene (2), tetradecene (3), hexadecene (4), and octadecene (5)) gave the respective 1,2-bis(2-bromoalkylthio)ethane (7-10). The bromoalkylthio ethers when reacted with pyridine (11) gave the respective gemini bispyridinium bromide (12-15). The surface properties of new geminis were evaluated by surface tension and conductivity measurements. These gemini surfactants have also been found to be having low cytotoxicity by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay on C6 glioma cells. The DNA binding capabilities of these amphiphiles have been determined below as well as above critical micelle concentration. The preliminary studies by agarose gel electrophoresis indicated chain length dependent DNA binding abilities which has further been proved by ethidium bromide exclusion experiments and transmission electron microscopy (TEM).