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90141-22-3

90141-22-3 Structure

90141-22-3 Structure
IdentificationBack 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 PropertiesBack 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.
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P280-P305+P351+P338
[WGK Germany ]

3
Hazard InformationBack 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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