1. Self-Aggregation, Antimicrobial Activity and Cytotoxicity of Ester-Bonded Gemini Quaternary Ammonium Salts: The Role of the Spacer.
- Author
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Liang Y, Li H, Ji J, Wang J, and Ji Y
- Subjects
- Humans, HeLa Cells, Staphylococcus aureus, Quaternary Ammonium Compounds pharmacology, Quaternary Ammonium Compounds chemistry, Anti-Bacterial Agents pharmacology, Surface-Active Agents pharmacology, Surface-Active Agents chemistry, Salts pharmacology, Escherichia coli
- Abstract
Five ester-bonded gemini quaternary ammonium surfactants C
12 -En -C12 (n = 2, 4, 6), with a flexible spacer group, and C12 -Bm -C12 (m = 1, 2), with rigid benzene spacers, were synthesized via a two-step reaction and analyzed. Furthermore, the effects of the spacer structure, spacer length and polymerization degree on the self-aggregation, antimicrobial activity and cytotoxicity of C12 -En -C12 and C12 -Bm -C12 and their corresponding monomer N -dodecyl- N , N , N -trimethyl ammonium chloride DTAC were investigated. The results showed that C12 -En -C12 and C12 -Bm -C12 had markedly lower critical micellar concentration (CMC) values and lower surface tension than DTAC. Moreover, the CMC values of C12 -En -C12 and C12 -Bm -C12 decreased with increasing spacer length. In the case of equivalent chain length, the rigidity and steric hindrance of phenylene and 1,4-benzenediyl resulted in larger CMC values for C12 -Bm -C12 than for C12 -En -C12 . The antibacterial ability of C12 -En -C12 and C12 -Bm -C12 was assessed using Escherichia coli ( E. coli ) and Staphylococcus albus ( S. aureus ) based on minimum inhibitory concentrations (MICs). Furthermore, C12 -En -C12 and C12 -Bm -C12 exhibited higher antimicrobial activity than DTAC and had stronger function toward S. aureus than E. coli . The antimicrobial activity was enhanced by increasing the spacer chain length and decreased with the increased rigidity of the spacers. The cytotoxic effects of C12 -En -C12 and C12 -Bm -C12 in cultured Hela cells were evaluated by the standard CCK8 method based on half-maximal inhibitory concentration (IC50 ). The cytotoxicity of C12 -En -C12 and C12 -Bm -C12 was significantly lower than alkanediyl-α,ω-bis(dimethyldodecylammonium) bromide surfactants and DTAC. The spacer structure and the spacer length could induce significant cytotoxic effects on Hela cells. These findings indicate that the five ester-bonded GQASs have stronger antibacterial activity and lower toxicity profile, and thus can be used in the pharmaceutical industry.- Published
- 2023
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