The anti-HIV activities of photoactive terthiophenes.
Various synthetic analogues of the naturally occurring terthiophene, alpha-terthienyl (alpha T), were evaluated for anti-human immunodeficiency virus (HIV) activity. The compounds were incubated individually with a known amount of the virus, with or without UVA radiation (long-wavelength ultraviolet) and residual virus was monitored for its ability to produce cytopathic effects in cell culture and the production of virus-specific protein (p24). The basic terthiophene structure was essential for good anti-HIV activity, although various side chains, such as alcohols, bromo, methyl, thiomethyl and trimethylsilyl groups, permitted retention of maximum activity. Under optimum conditions, as little as 12 ng/mL of these compounds (i.e. approximately 3 x 10(-8) M) could inactivate 10(3) infectious virions. None of the compounds however were more active than alpha T itself. In all cases, UVA radiation was essential. Several side chains decreased the antiviral efficacy, and some side chains abrogated the activity.
Hudson
J B
JB
Division of Medical Microbiology, University of British Columbia, Vancouver, Canada.
Harris
L
L
Marles
R J
RJ
Arnason
J T
JT
D000998:Antiviral Agents / Q000633:toxicity*; D002460:Cell Line; D016655:HIV Core Protein p24 / Q000032:analysis / Q000378:metabolism; D015497:HIV-1 / Q000187:drug effects* / Q000254:growth & development / Q000528:radiation effects; D006801:Humans; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000633:toxicity*; D014466:Ultraviolet Rays
D000998:Antiviral Agents; D016655:HIV Core Protein p24; D013876:Thiophenes; C019101:alpha-terthienyl