Differential binding of (+) and (-) gossypol to plasma protein and their entry into rat testis

Abstract

Summary. Concentrations of ( + )and ( \ m=-\ ) gossypol were measured by high performance liquid chromatography after they were incubated with plasma proteins in vitro. The concentration of ( \m=-\) gossypol decreased more than the concentration of ( + ) gossypol. A similar decrease in free gossypol concentrations in the blood plasma of rats was observed after intravenous infusion of gossypol enantiomers. The concentration of ( \ m=-\ ) gossypol was also found to be lower than the concentration of ( + ) gossypol at the blood\p=n-\testisbarrier. The biological effect of ( \ m=-\ ) gossypol probably results from its stereospecific binding to extra-and intracellular proteins in vivo and inhibition of the biological activity of some proteins.

Quantitative determination of apogossypol, a pro-apoptotic analog of gossypol, in mouse plasma using LC/MS/MS

“…By using a combination of molecular modeling and structural biology techniques, (±)-apogossypol, which lacks the reactive aldehyde groups and retains pro-apoptotic activity, has recently been synthesized and shown to bind to and inhibit the Bcl-2-family proteins, Bcl-2 and Bcl-X L , inducing apoptosis of the tumor cell lines [3]. Quantitative measurement of gossypol and its analogs in bio-matrixes has been achieved and refined for more than 25 years, including high-performance liquid chromatography [4][5][6] electrochemical detection [7][8][9], radiolabeling [10] and fluorescence quenching titrations [11]. However, these methods can be time-consuming and laborintensive, in that they involve several steps in sample preparation.…”

Reproductive toxicologic effects of gossypol on male rabbits: biochemical, enzymatic, and electrolytic properties of seminal plasma

“…To our knowledge, no previous studies regarding the effect of gossypol on seminal plasma constituents have been reported. However, several investigations have been performed on the effect of gossypol on blood plasma constituents, from which its effect on seminal plasma constituents can be extrapolated because of the ability of gossypol to cross the blood-testis barrier (1).…”

Biological Properties of Schiff Bases and Azo Derivatives of Phenols

“…Generally, the (R)-(-) enantiomer of gossypol is biologically more active than the racemate or the (S)-(+) enantiomer [11][12][13][14]. The synthesis of racemic gossypol was first performed by Edwards [15] and Meyers.…”