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Gossypol

Gossypol

Product ID G5874
Cas No. 303-45-7
Purity ≥98%
Product Unit SizeCostQuantityStock
25 mg $71.50 In stock
100 mg $173.70 In stock
250 mg $337.10 In stock
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  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Custom Order

Description

Gossypol is a polyphenol found in Gossypium that exhibits anti-fertility, antimalarial, immunosuppressive, antiviral, and anticancer chemotherapeutic activities. Gossypol inhibits calcineurin, PKC, and other kinases. Gossypol is under consideration for use as a male contraceptive as it induces spermatogenesis arrest. Gossypol also inactivates HIV-1 in vitro and inhibits viral entry of H5N1 influenza virus. In vitro, gossypol inhibits ConA-induced increases in NF-κB, NFAT, and AP-1 signaling, suppressing T cell activation in vitro. Gossypol also acts as a BH3 mimetic, inhibiting Bcl-2 and Bcl-xl, inducing G2/M phase cell cycle arrest in wild type and B-RAF mutant melanoma and myeloma cells.

Product Info

Cas No.

303-45-7

Purity

≥98%

Formula

C30H30O8

Formula Wt.

518.55

Chemical Name

1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1- methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde

IUPAC Name

7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3, 8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde

Synonym

2,2'-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)

Melting Point

198

Solubility

Soluble in DMSO, methanol or ethanol. Insoluble in water.

Appearance

Bright Yellow Powder

Shipping and Storage

Store Temp

4°C

Ship Temp

Ambient

Downloads

MSDS

G5874 MSDS PDF

Info Sheet

G5874 Info Sheet PDF

References

Jang GH, Lee M. BH3-mimetic gossypol-induced autophagic cell death in mutant BRAF melanoma cells with high expression of p21Cip¹.). Life Sci. 2014 Apr 25;102(1):41-8. PMID: 24625733.

Song B, Huang G, Tong C, et al. Gossypol suppresses mouse T lymphocytes via inhibition of NFκB, NFAT and AP-1 pathways. Immunopharmacol Immunotoxicol. 2013 Oct;35(5):615-21. PMID: 23981004.

Lin J, Wu Y, Yang D, et al. Induction of apoptosis and antitumor effects of a small molecule inhibitor of Bcl-2 and Bcl-xl, gossypol acetate, in multiple myeloma in vitro and in vivo. Oncol Rep. 2013 Aug;30(2):731-8. PMID: 23708869.

Yang J, Chen G, Li LL, et al. Synthesis and anti-H5N1 activity of chiral gossypol derivatives and its analogs implicated by a viral entry blocking mechanism. Bioorg Med Chem Lett. 2013 May 1;23(9):2619-23. PMID: 23538114.

Coutinho EM. Gossypol: a contraceptive for men. Contraception. 2002 Apr;65(4):259-63. PMID: 12020773.

Polsky B, Segal SJ, Baron PA, et al. Inactivation of human immunodeficiency virus in vitro by gossypol. Contraception. 1989 Jun;39(6):579-87. PMID: 2473865.

Volate SR, Kawasaki BT, Hurt EM, et al. Gossypol induces apoptosis by activating p53 in prostate cancer cells and prostate tumor-initiating cells. Mol Cancer Ther. 2010 Feb;9(2):461-470. PMID: 20124455.

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