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| | (-)-Gossypol Basic information |
| Product Name: | (-)-Gossypol | | Synonyms: | AT 101, >=98%;DL-gossypol acetic acid;(R)-(-)-Gossypol;(R)-1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-[2,2'-binaphthalene]-8,8'-dicarboxaldehyde;(R)-Gossypol;R-(-)-gossypol acetic acid;GOSSYPOL 90141-22-3;CS-619 | | CAS: | 90141-22-3 | | MF: | C30H30O8 | | MW: | 518.55 | | EINECS: | | | Product Categories: | Inhibitors | | Mol File: | 90141-22-3.mol |  |
| | (-)-Gossypol Chemical Properties |
| Melting point | 166-167℃ | | alpha | D28 -386 to -390° (c = 0.5 g/100 g soln in CHCl3) | | Boiling point | 707.9±55.0 °C(Predicted) | | density | 1.403 | | storage temp. | -20°C | | solubility | DMSO: soluble15mg/mL, clear | | form | powder | | pka | 7.15±0.50(Predicted) | | color | white to light brown | | optical activity | [α]/D -350 to -365°, c = 0.3 (CDCl3) | | Stability: | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. |
| | (-)-Gossypol Usage And Synthesis |
| Description | AT-101 (90141-22-3) is a small molecule mimic of the BH3 domain of cellular Bcl-2 inhibitors which interferes with the function of Bcl-2-family antiapoptotic proteins. AT-101 induces apoptosis in drug-resistant multiple myeloma cell lines. Apoptosis is activated by the mitochondrial pathway. Cell permeable. | | Uses | AT-101 is a BH3 mimetic known to be a potent inhibitor of antiapoptotic Bcl-2 family members. | | Biological Activity | R-(-)-enantiomer of gossypol (Gossypol). Mimics the BH3 domains of Bcl-2, Bcl-XL and Mcl-1. Disrupts heterodimerization of Bcl-2 with proapoptotic family members. Induces apoptosis in vitro through activation of caspase-9; cytotoxic to multiple myeloma and drug-resistant cell lines. Delays onset of androgen-independent growth of VCaP prostate cancer xenografts in vivo . | | Biochem/physiol Actions | AT101 [R-(-)-enantiomer of gossypol] is an orally available and well-tolerated natural BH3-mimetic that activates Bax and also induces mitochondrial Smac release. AT101 has shown anti-tumor activity as a single agent and in combination with standard anticancer drugs in a variety of tumor models. AT101 induced apoptosis in chemoresistant ovarian cancer cells. | | storage | Store at -20°C | | References | 1) Kline et al. (2008), R-(-)-gossypol (AT-101) activates programmed cell death in multiple myeloma cells; Exp. Hematol., 36 568
2) Balakrishnan et al. (2009), AT-101 induces apoptosis in CLL B cells and overcomes stromal cell-mediated Mcl-1 induction and drug resistance; Blood, 113 149 |
| | (-)-Gossypol Preparation Products And Raw materials |
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