A structure–activity study of spermicidal and anti-HIV properties of hydroxylated cationic surfactants Original Research Article

A structure–activity study of spermicidal and anti-HIV properties of hydroxylated cationic surfactants Original Research Article Pages 3599-3608 Yue-Ling Wong, M.Patricia Hubieki, Christopher L Curfman, Gustavo F Doncel, Travis C Dudding, Prashant S Savle, Richard D Gandour Close preview | Related articles | Related reference work articles Abstract | Figures/Tables | References Abstract The syntheses of 2-hydroxy-N-(2-hydroxyethyl)-N,N-dimethylhexadecan-1-aminium chloride [1(16)Cl] and iodide [1(16)I], 2-hydroxy-N,N,N-trimethylhexadecan-1-aminium chloride (6), N-(2-hydroxyethyl)-N,N-dimethylhexadecan-1-aminium chloride (8), N,N-bis(2-hydroxyethyl)-N-methylhexadecan-1-aminium chloride (11), and 2-hydroxy-N-(2-hydroxyethyl)-N,N-dimethyl-4-oxahexadecan-1-aminium chloride (14) are reported along with the critical micelle concentrations (cmcs), as measured by conductivity at 25 °C, of 1(16)Cl, 1(16)I, 6, 8, 11, and N,N,N-trimethylhexadecan-1-aminium chloride (12). All compounds display spermicidal and virucidal activity. A plot of minimum effective concentration (MEC) in the Sander–Cramer spermicidal assay and cmc shows that 1(16)Cl and 6 have the best spermicidal activity and highest cmcs. Compounds 8, 11, and 1(16)Cl are the most active at 0.05 mg mL−1 against cell-free and cell-associated virus. In conclusion, 1(16)Cl shows the best combination of dual activity against sperm and HIV; it is a promising candidate for further preclinical studies as a topical, contraceptive microbicide. Article Outline Introduction Results Chemistry Biology Discussion Spermicidal activity and micellar concentration Anti-HIV properties Comparison with previous work Conclusion Experimental General Syntheses 2-Hydroxy-N-(2-hydroxyethyl)-N-methyl-1-hexadecanamine, 4 2-Hydroxy-N-(2-hydroxyethyl)-N,N-dimethyl-1-hexadecanaminium iodide, 1(16)I 2-Hydroxy-N-(2-hydroxyethyl)-N,N-dimethyl-1-hexadecanaminium chloride, 1(16)Cl 2-Hydroxy-N,N-bis(2-hydroxyethyl)-N-methyl-1-hexadecanaminium chloride, 2(16)Cl 2-Hydroxy-N,N,N-trimethyl-1-hexadecanaminium chloride, 6 N-(2-Hydroxyethyl)-N,N-dimethyl-1-hexadecanaminium chloride, 8 N-Methyl-1-hexadecanamine, 9 N-(2-Hydroxyethyl)-N-methyl-1-hexadecanamine, 10 N,N-Bis(2-hydroxyethyl)-N-methyl-1-hexadecanaminium chloride, 11 Recrystallization of N,N,N-Trimethyl-1-hexadecanaminium chloride, 12 2-Oxatetradecyloxirane, 13 2-Hydroxy-N-(2-hydroxyethyl)-N,N-dimethyl-4-oxahexadecan-1-aminium chloride, 14 Determination of critical micelle concentrations by conductivity Semen samples In vitro spermicidal activity Statistical analysis In vitro anti-HIV activity Acknowledgements References