90141-22-3

Basic information

• Product Name: GOSSYPOL
• Synonyms: (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;AT 101, >=98%;DL-gossypol acetic acid
• CAS NO: 90141-22-3
• Molecular Formula: C30H30O8
• Molecular Weight: 518.5544
• Product Categories: Inhibitors
• Mol File: 90141-22-3.mol
• Article Data: 0

Chemical Properties

• Melting Point: 166-167℃
• Boiling Point: 707.9 ºCat 760 mmHg
• Flash Point: 395.9ºC
• Appearance: white to light brown/
• Density: 1.403
• Storage Temp.: Store at -20°C
• Solubility: DMSO: soluble15mg/mL, clear
• PKA: 7.15±0.50(Predicted)
• 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.
• CAS DataBase Reference: GOSSYPOL(CAS DataBase Reference)
• NIST Chemistry Reference: GOSSYPOL(90141-22-3)
• EPA Substance Registry System: GOSSYPOL(90141-22-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 90141-22-3(Hazardous Substances Data)

Usage

Description

GOSSYPOL is a naturally occurring polyphenolic compound derived from the cotton plant (Gossypium spp.). It possesses unique chemical properties and biological activities, making it a versatile compound with potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
GOSSYPOL is used as a pharmaceutical agent for its potential anticancer properties. It has been shown to induce apoptosis in various cancer cell lines, making it a promising candidate for cancer treatment.
Used in Agricultural Industry:
GOSSYPOL is used as a natural pesticide for its insecticidal properties. It can effectively control pests in crops, reducing the need for chemical pesticides and promoting sustainable agriculture.
Used in Food Industry:
GOSSYPOL is used as a food additive for its antioxidant properties. It can help preserve the freshness and quality of food products, as well as provide health benefits due to its antioxidant capacity.
Used in Cosmetic Industry:
GOSSYPOL is used as an ingredient in cosmetic products for its potential skin health benefits. It may help improve skin elasticity, reduce wrinkles, and provide antioxidant protection.
Used in Environmental Industry:
GOSSYPOL can be used as a natural dye for coloring textiles and other materials. Its use as a natural alternative to synthetic dyes can help reduce environmental pollution and promote eco-friendly practices.

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.

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