| Identification | Back Directory | [Name]
(-)-Gossypol | [CAS]
90141-22-3 | [Synonyms]
CS-619
C:C&B61
(-)-Gossypol
(R)-Gossypol
AT 101, >=98%
GOSSYPOL，AT101
(R)-(-)-Gossypol
GOSSYPOL 90141-22-3
(-)-Gossypol USP/EP/BP
DL-gossypol acetic acid
R-(-)-gossypol acetic acid
(R)-(-)-GOSSYPOL;R-(-)-GOSSYPOL ACETIC ACID
(R)-1,1',6,6',7,7'-Hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-[2,2'-binaphthalene]-8,8'-dicarboxaldehyde
[2,2'-Binaphthalene]-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-, (2R)- | [Molecular Formula]
C30H30O8 | [MDL Number]
MFCD00017352 | [MOL File]
90141-22-3.mol | [Molecular Weight]
518.55 |
| Chemical Properties | Back Directory | [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. ]
Store at -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. |
| Hazard Information | Back Directory | [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 |
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