(±)-Gossypol

• CAT Number: I003062
• CAS Number: 303-45-7
• Molecular Formula: C₃₀H₃₀O₈
• Molecular Weight: 518.55
• Purity: ≥95%
• Target: Bcl-2 Family
• Solubility: DMF:25mg/ml;25 mM in DMSO; methanol:2 mg/ml
• Storage: Store at -20°C
• 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
• InChI: InChI=1S/C30H30O8/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36/h7-12,33-38H,1-6H3
• InChIKey: QBKSWRVVCFFDOT-UHFFFAOYSA-N
• 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

(±)-Gossypol (Cat.No: I003062) is a naturally occurring polyphenol found in the cotton plant. It has been studied for its potential anticancer and contraceptive properties. The compound works by inhibiting the activity of certain enzymes involved in cell growth and division. However, (±)-Gossypol can also have toxic effects on healthy cells, so its use as a therapeutic agent is still being explored.

Reference

1:Development of SECheM Concept for Isolation and Chemical Modification of Gossypol Directly from Cienfuegosia digitata. Sidi Boune MV, Ould Elemine B, Lepitre T, Ould Hadou A, Aliyenne A, Boumediana AI, Daïch A, Othman M, Lawson AM.Phytochem Anal. 2017 May 5. doi: 10.1002/pca.2688. [Epub ahead of print] PMID: 28474346 2:The Lactate Dehydrogenase Inhibitor Gossypol Inhibits Radiation-Induced Pulmonary Fibrosis. Judge JL, Lacy SH, Ku WY, Owens KM, Hernady E, Thatcher TH, Williams JP, Phipps RP, Sime PJ, Kottmann RM.Radiat Res. 2017 May 2. doi: 10.1667/RR14620.1. [Epub ahead of print] PMID: 28463588 3:Preparation and evaluation of molecularly imprinted polymer for selective recognition and adsorption of gossypol. Zhi K, Wang L, Zhang Y, Zhang X, Zhang L, Liu L, Yao J, Xiang W.J Mol Recognit. 2017 Mar 22. doi: 10.1002/jmr.2627. [Epub ahead of print] PMID: 28326626 4:Gossypol has anti-cancer effects by dual-targeting MDM2 and VEGF in human breast cancer. Xiong J, Li J, Yang Q, Wang J, Su T, Zhou S.Breast Cancer Res. 2017 Mar 9;19(1):27. doi: 10.1186/s13058-017-0818-5. PMID: 28274247 Free PMC Article5:Gossypol with Hydrophobic Linear Esters Exhibits Enhanced Antitumor Activity as an Inhibitor of Antiapoptotic Proteins. Lu Y, Wu S, Yue Y, He S, Li J, Tang J, Wang W, Zhou HB.ACS Med Chem Lett. 2016 Oct 19;7(12):1185-1190. eCollection 2016 Dec 8. PMID: 27994761 6:Determination of gossypol content in cottonseeds by near infrared spectroscopy based on Monte Carlo uninformative variable elimination and nonlinear calibration methods. Li C, Zhao T, Li C, Mei L, Yu E, Dong Y, Chen J, Zhu S.Food Chem. 2017 Apr 15;221:990-996. doi: 10.1016/j.foodchem.2016.11.064. Epub 2016 Nov 15. PMID: 27979304 7:Dietary gossypol suppressed postprandial TOR signaling and elevated ER stress pathways in turbot (Scophthalmus maximus L.). Bian F, Jiang H, Man M, Mai K, Zhou H, Xu W, He G.Am J Physiol Endocrinol Metab. 2017 Jan 1;312(1):E37-E47. doi: 10.1152/ajpendo.00285.2016. Epub 2016 Nov 15. PMID: 27894064 8:Expression in Pichia pastoris and characterization of two novel dirigent proteins for atropselective formation of gossypol. Effenberger I, Harport M, Pfannstiel J, Klaiber I, Schaller A.Appl Microbiol Biotechnol. 2017 Mar;101(5):2021-2032. doi: 10.1007/s00253-016-7997-3. Epub 2016 Nov 17. PMID: 27858135 9:Injectable (-)-gossypol-loaded Pluronic P85 micelles for cancer chemoradiotherapy. Tomoda K, Chiang HC, Kozak KR, Kwon GS.Int J Radiat Biol. 2017 Apr;93(4):402-406. doi: 10.1080/09553002.2016.1257833. Epub 2016 Dec 9. PMID: 27827005 10:Gossypol toxicity and detoxification in Helicoverpa armigera and Heliothis virescens. Krempl C, Heidel-Fischer HM, Jiménez-Alemán GH, Reichelt M, Menezes RC, Boland W, Vogel H, Heckel DG, Joußen N.Insect Biochem Mol Biol. 2016 Nov;78:69-77. doi: 10.1016/j.ibmb.2016.09.003. Epub 2016 Sep 26. PMID: 27687846