Disease relevance of NSC651924

• They react easily with electrophiles in aprotic solvents to regenerate gossypolone or to form dehydrogossypoldithianes and dehydrogossypoldithiolanes, which display higher toxicity on KB cells [1].

High impact information on NSC651924

• To explore further the antitumor properties of this multifunctional agent, we synthesized several reactive derivatives including the (-,+) enantiomers of gossypolone and four different gossypol Schiff's bases (AR1, AR2, AR3, AR4) [2].
• Racemic gossypolone showed relatively uniform antiproliferative activity against all of the breast epithelial cell lines with 3- to 5-fold less activity than (--)-gossypol against MCF-7 and MCF-7/adr cells [2].
• Gossypol and gossypolone enantiomers in tissues of rainbow trout fed low and high levels of dietary cottonseed meal [3].
• Gossypolone, however, was not detected in blood plasma, muscle, and testis of fish fed the low-CM diet [3].
• The ratio of gossypolone to gossypol was highest in muscle (1.75), followed by intestine (1.59), stomach (1.50), kidney (0.43), liver (0.34), testis (0.28), and blood plasma (0.27) [3].

Biological context of NSC651924

• Racemic gossypol 1a and gossypolone 2 induced similar dose-dependent decreases in cell viability in all the cell lines with IC50 values of 23-46 and 28-50 microM, respectively [4].

Anatomical context of NSC651924

• Stereo-specific cytotoxic effects of gossypol enantiomers and gossypolone in tumour cell lines [5].
• We have reported that gossypol, an antifertility agent, and gossypolone, a major metabolite of gossypol, inhibited steroidogenesis in bovine luteal cells in vitro [6].

Gene context of NSC651924

• The cytotoxicity of gossypol and gossypolone was increased when the tests were performed in the absence of serum and decreased when catalase as well as mannitol were added to the culture medium [7].

Analytical, diagnostic and therapeutic context of NSC651924

• The enantiomers and the proposed oxidative metabolite, gossypolone, were characterized by HPLC, 1H-NMR and optical rotation [5].

References