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Gossypol

Male antifertility agent
 
BML-EI130-0100 100 mg 112.00 USD
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Replaces Prod. #: ALX-350-113

Mixture of ~65% (+)- and ~35% (-)-enantiomers. Male antifertility agent with antispermatogenic activity. Shows antitumor, antiviral and antioxidant actions. Small molecule inhibitor of Bcl-2/Bcl-XL. Induces apoptosis. Synergizes with radiation and chemotherapy in vitro. Reversible inhibitor of protein phosphatase 2B (PP2B; calcineurin). Protein kinase C (PKC) inhibitor. Inhibits activities of the mitotic kinesin Eg5 (IC50=10.8µM/L). Inhibits RBL-1, 5-lipoxygenase (IC50=0.3µM) and 12-lipoxygenase (IC50=0.7µM). Inhibits PAF and leukotriene-induced guinea pig parenchyma contractions. Novel direct-acting inhibitor of calcineurin.

Product Specification

Alternative Name:2,2’-bis[8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene]
 
Formula:C30H30O8
 
MW:518.6
 
Source:Isolated from Gossypium genus, Malvaceae.
 
CAS:303-45-7
 
MI:14: 4528
 
RTECS:DU3100000
 
Purity:≥90% (HPLC)
 
Appearance:Off-white to yellow solid.
 
Solubility:Soluble in 100% ethanol (25mg/ml), dimethylformamide (25mg/ml), acetone or DMSO; sparingly soluble in methanol (2mg/ml); insoluble in water.
 
Shipping:Shipped on Blue Ice
 
Long Term Storage:-20°C
 
Use/Stability:Stable for at least 1 year after receipt when stored at -20°C. Stock solutions are stable for up to 1 month at -20°C. Avoid alkaline solutions.
 
Handling:Protect from light and oxygen. Keep under inert gas.
 
Technical Info/Product Notes:Note: Product is not sterile.
 
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Product Literature References

(-)-Gossypol enhances response to radiation therapy and results in tumor regression of human prostate cancer: L. Xu, et al.; Mol. Cancer Ther. 4, 197 (2005), Abstract; Full Text
An in vitro study of cytotoxic effects of gossypol on human epidermoid larynx carcinoma cell line (HEp-2): E. Konac, et al.; Exp. Oncol. 27, 81 (2005), Abstract; Full Text
Investigations on gossypol: past and present developments: K. Dodou; Expert Opin. Investig. Drugs 14, 1419 (2005), Abstract;
In vitro effects of the BH3 mimetic, (-)-gossypol, on head and neck squamous cell carcinoma cells: C.L. Oliver, et al.; Clin. Cancer Res. 10, 7757 (2004), Abstract; Full Text
In vitro screening for inhibitors of the human mitotic kinesin Eg5 with antimitotic and antitumor activities: S. DeBonis, et al.; Mol. Cancer Ther. 3, 1079 (2004), Abstract;
The inhibitory effects of gossypol on human prostate cancer cells-PC3 are associated with transforming growth factor beta1 (TGFbeta1) signal transduction pathway: J. Jiang, et al.; Anticancer Res. 24, 19 (2004), Abstract;
Determination of the absolute configuration and solution conformation of gossypol by vibrational circular dichroism: T.B. Freedman, et al.; Chirality 15, 196 (2003), Abstract;
An in vitro study of inhibitory activity of gossypol, a cottonseed extract, in human carcinoma cell lines: M. Le Blanc, et al.; Pharmacol. Res. 46, 551 (2002), Abstract;
Gossypol induces chloride secretion in rat proximal colon: G. Kuhn, et al.; Eur. J. Pharmacol. 457, 187 (2002), Abstract;
Telomerase inhibitors in anticancer therapy: gossypol as a potential telomerase inhibitor: M. Mego; Bratisl. Lek. Listy 103, 378 (2002), Abstract;
Toxicity of (+)- and (-)-gossypol to the plant pathogen, Rhizoctonia solani: L.S. Puckhaber, et al.; J. Agric. Food Chem. 50, 7017 (2002), Abstract;
Reversible inhibition of calcineurin by the polyphenolic aldehyde gossypol: R. Baumgrass, et al.; J. Biol. Chem. 276, 47914 (2001), Abstract; Full Text
Cytotoxic effect of gossypol on colon carcinoma cells: X. Wang, et al.; Life Sci. 67, 2663 (2000), Abstract;
Inhibition of huntingtin fibrillogenesis by specific antibodies and small molecules: implications for Huntington’s disease therapy: V. Heiser, et al.; PNAS 97, 6739 (2000), Abstract; Full Text
Gossypol arrests human benign prostatic hyperplastic cell growth at G0/G1 phase of the cell cycle: F. Shidaifat, et al.; Anticancer Res. 17, 1003 (1997), Abstract;
Induction of apoptotic DNA fragmentation and cell death in HL-60 human promyelocytic leukemia cells by pharmacological inhibitors of protein kinase C: W.D. Jarvis, et al.; Cancer Res. 54, 1707 (1994), Abstract;
Differential inhibition of protein kinase C subtypes: J.M. Pelosin, et al.; BBRC 169, 1040 (1990), Abstract;
Gossypol: a potent inhibitor of PAF-acether- and leukotriene-induced contractions of guinea-pig lung parenchyma strips: C. Touvay, et al.; J. Pharm. Pharmacol. 39, 454 (1987), Abstract;
Binding of gossypol to purified tubulin and inhibition of its assembly into microtubules: F.J. Medrano and J.M. Andreu; Eur. J. Biochem. 158, 63 (1986), Abstract;
Gossypol, a potent inhibitor of arachidonate 5- and 12-lipoxygenases: Y. Hamasaki & H.H. Tai; Biochim. Biophys. Acta 834, 37 (1985), Abstract;
Gossypol: a potential antifertility agent for males: S.Z. Qian & Z.G. Wang; Annu. Rev. Pharmacol. Toxicol. 24, 329 (1984), Abstract;

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