title: A structure-activity study of spermicidal and anti-HIV properties of hydroxylated cationic surfactants.
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 degrees 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.
authors.affiliation: Department of Chemistry, Virginia Tech, Blacksburg, VA 24061-0212, USA.
authors.forename: Yue-Ling
authors.initials: YL
authors.lastname: Wong
authors.forename: M Patricia
authors.initials: MP
authors.lastname: Hubieki
authors.forename: Christopher L
authors.initials: CL
authors.lastname: Curfman
authors.forename: Gustavo F
authors.initials: GF
authors.lastname: Doncel
authors.forename: Travis C
authors.initials: TC
authors.lastname: Dudding
authors.forename: Prashant S
authors.initials: PS
authors.lastname: Savle
authors.forename: Richard D
authors.initials: RD
authors.lastname: Gandour
mesh_terms: D019380:Anti-HIV Agents / Q000737:chemistry* / Q000494:pharmacology*; D002412:Cations; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D006900:Hydroxylation; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D008297:Male; D008823:Micelles; D008826:Microbial Sensitivity Tests; D010100:Oxygen / Q000737:chemistry; D013089:Spermatocidal Agents / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013501:Surface-Active Agents / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D019380:Anti-HIV Agents; D002412:Cations; D007202:Indicators and Reagents; D008823:Micelles; D013089:Spermatocidal Agents; D013501:Surface-Active Agents; D010100:Oxygen