Introduction：Basic information about (-)-Gossypol CAS 90141-22-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
(-)-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 |
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(-)-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 |
| pka | 7.15±0.50(Predicted) |
| form | powder |
| color | white to light brown |
| Optical Rotation | [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. |
| 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 |
Safety Information
| WGK Germany | 3 |
| Storage Class | 11 - Combustible Solids |
(-)-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] MICHAEL P. KLINE. R-(-)−gossypol (AT-101) activates programmed cell death in multiple myeloma cells[J]. Experimental hematology, 2008, 36 5: Pages 568-576. DOI:10.1016/j.exphem.2008.01.003
[2] KUMUDHA BALAKRISHNAN. AT-101 induces apoptosis in CLL B cells and overcomes stromal cell-mediated Mcl-1 induction and drug resistance.[J]. Blood, 2009: 149-153. DOI:10.1182/blood-2008-02-138560 |
(-)-Gossypol Preparation Products And Raw materials
