(-)-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 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 Information

WGK Germany 

3

(-)-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

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