Synthesis and Anti-HIV Activity of 1,1'-Dideoxygossypol and Related Compounds

Abstract

1,1'-Dideoxygossypol (DDG), 1,1'-dideoxygossylic acid (DDGA), 8-deoxyhemigossypol (DHG), and 8-deoxyhemigossylic acid (DHGA) were synthesized and tested for their ability to inhibit the replication of HIV in vitro. The EC50 for DDGA was < 1 microM, and its threshold cytotoxicity was approximately 20 microM. DDG was less effective than DDGA against HIV and showed considerable toxicity at 5 microM. DHGA was ineffective against HIV and had very low cytotoxicity. DHG showed some anti-HIV activity, but the threshold cytotoxicity was 5 microM. The dissociation constants for the binding of the four compounds to human serum albumin were determined by fluorescence quenching titrations, and all four were found to have much lower affinities for albumin than the parent compound gossypol.

Salicylaldehyde thiazolyl hydrazones as ligands

“…Magnetic susceptibilities were determined on a Sherwood Scientific magnetic susceptibility balance (Model MK1) at room temperature (20 • C) using Hg[Co(SCN) 4 ] as calibrant; diamagnetic corrections were calculated from Pascal's constants. Melting points were determined on a Gallenkamp apparatus; they were checked by DSC technique and are uncorrected.…”

The schiff base of gossypol with 3,6,9,12,15,18,21,24‐octaoxa‐pentacosylamine complexes and monovalent cations studied by electrospray ionization–mass spectrometry, 1H nuclear magnetic resonance, Fourier transform infrared, as well as PM5 semiempirical methods

“…42 This fact is very important for a wider use of gossypol Schiff bases in medical therapy. Some of the gossypol Schiff bases show antimalarial activity 43 ; others are more efficient than gossypol itself in inhibition of the replication of HIV in vitro 44 and also show cytotoxic activities towards human cancer cells. 42,45 The Schiff bases of gossypol can occur in imineimine and enamine-enamine tautomeric forms 46 -55 (Scheme 1), being analogues to the aldehyde-aldehyde and ketol-ketol tautomers of gossypol, 56 -59 respectively.…”

Identification of natural products and their derivatives as promising inhibitors of protein glycation with non-toxic nature against mouse fibroblast 3T3 cells

“…A large number of gossypol derivatives, such as Schiff's bases, esters, and ethers have been prepared. Several gossypol derivatives and analogs, such as compounds 3-6, possess activities such as antimalarial, anti-cancer, HIV (human immunodeficiency virus), and antiparasitic properties [31][32][33][34][35][36][37]. High throughput screening studies on a gossypol derivative 5 were performed in vivo and in vitro.…”