886578-07-0

Basic information

• Product Name: [2,2'-Binaphthalene]-1,1',4,4'-tetrone, 6,6',7,7'-tetrahydroxy-3,3'-diMethyl-5,5'-bis(1-Methylethyl)-
• Synonyms: [2,2'-Binaphthalene]-1,1',4,4'-tetrone, 6,6',7,7'-tetrahydroxy-3,3'-diMethyl-5,5'-bis(1-Methylethyl)-;Apogossypolone (ApoG2);Apogossypolone;Gossypol Derivative ApoG2
• CAS NO: 886578-07-0
• Molecular Formula: C28H26O8
• Molecular Weight: 490.50124
• Mol File: 886578-07-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: [2,2'-Binaphthalene]-1,1',4,4'-tetrone, 6,6',7,7'-tetrahydroxy-3,3'-diMethyl-5,5'-bis(1-Methylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: [2,2'-Binaphthalene]-1,1',4,4'-tetrone, 6,6',7,7'-tetrahydroxy-3,3'-diMethyl-5,5'-bis(1-Methylethyl)-(886578-07-0)
• EPA Substance Registry System: [2,2'-Binaphthalene]-1,1',4,4'-tetrone, 6,6',7,7'-tetrahydroxy-3,3'-diMethyl-5,5'-bis(1-Methylethyl)-(886578-07-0)

Safety Data

• Hazardous Substances Data: 886578-07-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
[2,2'-Binaphthalene]-1,1',4,4'-tetrone, 6,6',7,7'-tetrahydroxy-3,3'-diMethyl-5,5'-bis(1-Methylethyl)is used as an anticancer agent for its ability to induce apoptosis in carcinoma cells and exhibit antiproliferative properties. Its complex structure and functional groups may interact with cellular targets, leading to the inhibition of cancer cell growth and proliferation.
Used in Chemical Research:
[2,2'-Binaphthalene]-1,1',4,4'-tetrone, 6,6',7,7'-tetrahydroxy-3,3'-diMethyl-5,5'-bis(1-Methylethyl)can be utilized in chemical research as a starting material or intermediate for the synthesis of other complex organic molecules. Its unique structure and functional groups make it a valuable candidate for the development of new pharmaceuticals, materials, or other specialty chemicals.
Used in Material Science:
The structural features of [2,2'-Binaphthalene]-1,1',4,4'-tetrone, 6,6',7,7'-tetrahydroxy-3,3'-diMethyl-5,5'-bis(1-Methylethyl)may also find applications in material science, particularly in the development of new polymers, coatings, or other advanced materials with specific properties. Its binaphthalene core and functional groups could contribute to the creation of materials with unique characteristics.

Biological Activity

apogossypolone is an inhibitor of bcl-2, mcl-1 and bcl-xl with ki values of 35nm, 25nm and 660nm, respectively [1].the mtt-based cell cytotoxicity assay shows that apogossypolone has an anticancer activity with ic50 values of 1, 2 and 3μm, respectively in pc-3, du-145 (human prostate cancer cell lines) and mda-mb-231(human breast cancer cell line). apogossypolone is also found to inhibit the colony formation of du-145 cells. the mechanism is that apogossypolone binds to bcl-2 and prevents its association with bh3-only pro-apoptotic proteins, leading the pro-apoptotic proteins to participate in the apoptotic response [2].besides prostate cancer and breast cancer, apogossypolone is also potent in follicular lymphoma. apogossypolone significantly inhibits the cell growth via inducing apoptosis in wsu-fsccl cell line with ic50 value of 109.2nm at 72h [3].

references

[1] zhang xq, huang xf, hu xb, zhan yh, an qx, yang sm, xia aj, yi j, chen r, mu sj, wu dc. apogossypolone, a novel inhibitor of antiapoptotic bcl-2 family proteins, induces autophagy of pc-3 and lncap prostate cancer cells in vitro. asian j androl. 2010 sep;12(5):697-708. [2] zhan y, jia g, wu d, xu y, xu l. design and synthesis of a gossypol derivative with improved antitumor activities. arch pharm (weinheim). 2009 apr;342(4):223-9.[3] arnold aa, aboukameel a, chen j, yang d, wang s, al-katib a, mohammad rm. preclinical studies of apogossypolone: a new nonpeptidic pan small-molecule inhibitor of bcl-2, bcl-xl and mcl-1 proteins in follicular small cleaved cell lymphoma model. mol cancer. 2008 feb 14;7:20.

Upstream product

• 303-45-7 (rac)-gossypol 
• 784206-41-3 apogossypol 
• 7144-61-8 5,5'-diisopropyl-1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-2,2'-binaphthalene 
• 886435-01-4 acetic acid 6,6',7'-triacetoxy-5,5'-diisopropyl-3,3'-dimethyl-1,4,1',4'-tetraoxo-1,4,1',4'-tetrahydro-[2,2']binaphthalenyl-7-yl ester 

Relevant articles and documents

Inhibitory effects of gossypol, gossypolone, and apogossypolone on a collection of economically important filamentous fungi

Racemic gossypol and its related derivatives gossypolone and apogossypolone demonstrated significant growth inhibition against a diverse collection of filamentous fungi that included Aspergillus flavus, Aspergillus parasiticus, Aspergillus alliaceus, Aspergillus fumigatus, Fusarium graminearum, Fusarium moniliforme, Penicillium chrysogenum, Penicillium corylophilum, and Stachybotrys atra. The compounds were tested in a Czapek agar medium at a concentration of 100 μg/mL. Racemic gossypol and apogossypolone inhibited growth by up to 95%, whereas gossypolone effected 100% growth inhibition in all fungal isolates tested except A. flavus. Growth inhibition was variable during the observed time period for all tested fungi capable of growth in these treatment conditions. Gossypolone demonstrated significant aflatoxin biosynthesis inhibition in A. flavus AF13 (B1, 76% inhibition). Apogossypolone was the most potent aflatoxin inhibitor, showing greater than 90% inhibition against A. flavus and greater than 65% inhibition against A. parasiticus (B1, 67%; G 1, 68%). Gossypol was an ineffectual inhibitor of aflatoxin biosynthesis in both A. flavus and A. parasiticus. Both gossypol and apogossypolone demonstrated significant inhibition of ochratoxin A production (47%; 91%, respectively) in cultures of A. alliaceus.

Synthesis and biological evaluation of apogossypolone derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins

Overexpression of antiapoptotic Bcl-2 family proteins is commonly related with tumor maintenance, progression, and chemoresistance. Inhibition of these antiapoptotic proteins is an attractive approach for cancer therapy. Guided by nuclear magnetic resonan

Design and synthesis of a gossypol derivative with improved antitumor activities

A novel chemical process has been devised for the synthesis of a new derivative of gossypol, 6,7,6',7'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl- [2,2']binaphthalenyl-1,4,1',4'-tetraone (Apogossypolone). This new process has only four steps, with a shorter synthesis span, a simple purification process, and improved yield and quality. The structure of apogossypolone was characterized by 1H-nuclear magnetic resonance, 13C- nuclear magnetic resonance, mass spectroscopy, infrared spectroscopy, and elemental analysis. Cell-cytotoxicity assay demonstrates that apogossypolone is three- to six-fold more potent than the parent compound, (-)-gossypol, in inhibiting the human prostate tumor cell lines PC-3 and DU-145 as well as the human breast cancer cell line MDA-MB-231. The colony-formation assay with DU-145 cells showed that apogossypolone inhibited more than 70% of colony formation at 1 μM, whereas (-)-gossypol at 10 μM only inhibited less than 50% of colony formation. The results indicate that apogossypolone exerts strong antitumor activities in human prostate and breast cancer cells, and thus represents a promising cancer therapeutic.