(-)-Gossypol
- CAS NO.:90141-22-3
- Empirical Formula: C30H30O8
- Molecular Weight: 518.55
- MDL number: MFCD00017352
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-06-30 15:45:59
What is (-)-Gossypol?
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.
The Uses of (-)-Gossypol
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
Properties of (-)-Gossypol
Melting point: | 166-167℃ |
Boiling point: | 707.9±55.0 °C(Predicted) |
alpha | D28 -386 to -390° (c = 0.5 g/100 g soln in CHCl3) |
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 for (-)-Gossypol
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral |
Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for (-)-Gossypol
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