Gossypol An inhibitor of PKC, Bcl-2, 5-LO, and 12-LO

Gossypol  (CAS 303-45-7)

Gossypol | CAS 303-45-7 is rated 5.0 out of 5 by 1.
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| See 6 Citations
Synonym: Pogosin; AT101; 2,2′-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)
Application: An inhibitor of PKC, Bcl-2, 5-LO, and 12-LO
CAS Number: 303-45-7
Purity: ≥90%
Molecular Weight: 518.56
Molecular Formula: C30H30O8
* Refer to Certificate of Analysis for lot specific data (including water content).
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Ordering Information

PRODUCT NAME CATALOG # UNIT PRICE QTY FAVORITES
Gossypol sc-200501 20 mg $36.00
Gossypol sc-200501A 100 mg $107.00

Gossypol is a male antifertility agent with antispermatogenic activity and has been shown to contain antitumor, anitviral, and antioxidant properties. Gossypol is a reversible inhibitor of PP2B (protein phosphatase 2B), mitotic kinesin Eg5, and PKC (protein kinase C). Gossypol also potentially inhibits PAF-R, Bcl-2, 5-LO (5-lipoxygenase), 12-LO, and leukotriene-induced guinea pig parenchyma contractions. Gossypol is an inhibitor of Bcl-xl, PKD and p107.


References

1. Qian, S.Z., et al. 1984. Annu. Rev. Pharmacol. Toxicol. 24: 329-360. PMID: 6375548
2. Hamasaki, Y. and Tai, H.H. 1985. Biochim. Biophys. Acta. 834: 37-41. PMID: 3919771
3. Medrano, F.J. and Andreu, J.M. 1986. Eur. J. Biochem. 158: 63-69. PMID: 3732269
4. Shidaifat, F., et al. 1997. Anticancer Res. 17: 1003-1009. PMID: 9137441
5. Wang, X., et al. 2000. Life Sci. 67: 2663-2671. PMID: 11105982
6. Jiang, J., et al. 2004. Anticancer Res. 24: 91-100. PMID: 15015581
7. Dodou, K., et al. 2005. Expert Opin Investig Drugs. 14: 1419-1434. PMID: 16255680

Physical State :
Solid
Derived From :
Gossypium genus, Malvaceae
Solubility :
Soluble in 100%ethanol (25 mg/ml), DMF (25 mg/ml), acetone, DMSO (25 mM), methanol (2 mg/ml), ether, chloroform, sodium carbonate, and dilute aqueous solutions of ammonia . Insoluble in water.
Storage :
Store at -20° C
Melting Point :
199° C
Boiling Point :
~707.9° C at 760 mmHg (Predicted)
Density :
~1.40 g/cm3 (Predicted)
Refractive Index :
n20D 1.74
IC50 :
mitotic kinesin Eg5: IC50 = 10.8 µM; RBL-1, 5-lipoxygenase: IC50 = 0.3 µM; 12-lipoxygenase: IC50 = 0.7 µM; PC-3 (Prostate carcinoma cells): EC5050 = 17.8 µM (Homo sapiens); PC-3 (Prostate carcinoma cells): EC5050 = 3.3 µM (Homo sapiens); Transitional endoplasmic reticulum ATPase: IC50 = 5.39 µM (Homo sapiens); Induced myeloid leukemia cell differentiation protein Mcl-1: IC50 = 1.36 µM (Homo sapiens); Estrogen receptor beta: IC50 >50 µM (Homo sapiens); Apoptosis regulator Bcl-2: IC50 = 0.5 µM (Homo sapiens); HCT-116 (Colon carcinoma cells): IC50 = 3.3 µM (Homo sapiens); Malate dehydrogenase mitochondrialMalate dehydrogenase mitochondrial: IC50 = 2.8 µM (Sus scrofa); MDA-MB-231 (Breast adenocarcinoma cells): IC50 = 1.9 µM (Homo sapiens); Lactate dehydrogenase: IC50 = 2.64 µM (Plasmodium falciparum); Malate dehydrogenase: IC50 = 2.03 µM (Plasmodium falciparum)
Ki Data :
Induced myeloid leukemia cell differentiation protein Mcl-1: Ki= 0.18 µM (Homo sapiens); Apoptosis regulator Bcl-X: Ki= 0.48 µM (Homo sapiens); Apoptosis regulator Bcl-2: Ki= 0.32 µM (Homo sapiens); Aldose reductase: Ki= 0.5 µM (Homo sapiens); Apoptosis regulator Bcl-2: Ki= 0.17 µM (Homo sapiens); Apoptosis regulator Bcl-W: Ki= 17.7 µM (Homo sapiens)
pK Values :
pKa: 7.15
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
DU3100000
PubChem CID :
3503
Merck Index :
14: 4528
MDL Number :
MFCD00017352
SMILES :
CC1=C(C(=C2C(=C1)C(=C(C(=C2C=O)O)O)C(C)C)O)C3=C(C=C4C(=C3O)C(=C(C(=C4C(C)C)O)O)C=O)C

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Gossypol Product Citations

See how others have used Gossypol. Click on the entry to view the PubMed entry .

Citations 1 to 6 of 6 total

PMID: # 25048245
Sundaram, B. et al. 2014. Purification of a recombinant histidine-tagged lactate dehydrogenase from the malaria parasite, Plasmodium vivax, and characterization of its properties. Biotechnol. Lett.. 36: 2473-80.

PMID: # 11105982
Wang, X. et al. 2000. Cytotoxic effect of gossypol on colon carcinoma cells. Life Sci.. 67: 2663-2671.

PMID: # 6375548
Qian, SZ. et al. 1984. Gossypol: a potential antifertility agent for males. Annu. Rev. Pharmacol. Toxicol.. 24: 329-360.

PMID: # 15015581
Jiang, J. et al. 2004 Jan-Feb. The inhibitory effects of gossypol on human prostate cancer cells-PC3 are associated with transforming growth factor beta1 (TGFbeta1) signal transduction pathway. Anticancer Res.. 24: 91-100.

PMID: # 23838624
Goncharova, I. et al. The location of the high- and low-affinity bilirubin-binding sites on serum albumin: ligand-competition analysis investigated by circular dichroism. Biophys. Chem.. 180-181: 55-65.

PMID: # 9137441
Shidaifat, F. et al. 1997 Mar-Apr. Gossypol arrests human benign prostatic hyperplastic cell growth at G0/G1 phase of the cell cycle. Anticancer Res.. 17: 1003-1009.

Citations 1 to 6 of 6 total

How long are stock solutions stable for? At what temperature?

Asked by: chemicalsmg
Thank you for your question. Stock solutions for sc-200501 are stable for up to 1 month if stored at -20ºC. If you have any further questions or concerns, please feel free to contact our Technical Service department by calling 800-457-3801 option 2, emailing scbt@scbt.com, or using the Live Chat function on our website.
Answered by: Tech Service 8
Date published: 2017-01-12
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Rated 5 out of 5 by from Jiang et al Jiang et al. (PubMed ID 15015584) found that gossypol prevented the proliferation of human prostate cancer cells by blocking induction of TGFbeta1 and influencing the expression of cell cycle proteins. -SCBT Publication Review
Date published: 2015-01-26
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