Author:

Keywords:

anionic metalloporphyrin, prodrug, antiviral, anti-HIV, gp120 interaction, Science & Technology, Life Sciences & Biomedicine, Biochemistry & Molecular Biology, Pharmacology & Pharmacy, Virology, HUMAN-IMMUNODEFICIENCY-VIRUS, SYNDROME AIDS, PHARMACOKINETIC PROPERTIES, POTASSIUM MONOPERSULFATE, REVERSE-TRANSCRIPTASE, PORPHYRIN COMPLEXES, ANTIVIRAL ACTIVITY, DEXTRAN SULFATE, V3 LOOP, MANGANESE, 0304 Medicinal and Biomolecular Chemistry, 0601 Biochemistry and Cell Biology, 1117 Public Health and Health Services, 3404 Medicinal and biomolecular chemistry

Abstract:

Various water-soluble polysulphonated and polycarboxylated porphyrins and some of their metallated derivatives have been prepared and their antiviral properties against human immunodeficiency virus (HIV-1, HIV-2), simian immunodeficiency virus and other viruses are reported. Besides these polyanionic compounds, two new series of porphyrins were included and studied from the perspective of bio-availability modulation: (i) acetylsulphonamido derivatives endowed with weak acidity properties (deprotonation gives the corresponding anionic derivatives in a pH range 4.5-8.5) and (ii) compounds with the anionic charge transiently masked by esterification (acetoxymethyl- and pivaloyloxymethylesters). Among the more active compounds in inhibiting HIV-induced cytopathic effects, the sulphonated and carboxylated porphyrin complexes were found to interact directly with the HIV protein gp120 and not with the CD4 cellular receptor.