(S)-Gossypol (acetic acid)

(S)-Gossypol is the isomer of a natural product Gossypol. (S)-Gossypol binds to the BH3-binding groove of Bcl-xL and Bcl-2 proteins with high affinity.

Product information

CAS Number: 1189561-66-7

Molecular Weight: 578.61

Formula: C32H34O10

Synonym:

(S)-(+)-Gossypol acetic acid

Chemical Name: acetic acid compound with (S)-1, 1', 6, 6', 7, 7'-hexahydroxy-5, 5'-diisopropyl-3, 3'-dimethyl-2, 2'-binaphthyl-8, 8'-dicarbaldehyde (1:1)

Smiles: CC(O)=O.CC1=CC2C(=C(C=O)C(O)=C(O)C=2C(C)C)C(O)=C1C1=C(O)C2C(C=O)=C(O)C(O)=C(C(C)C)C=2C=C1C

InChiKey: NIOHNDKHQHVLKA-UHFFFAOYSA-N

InChi: InChI=1S/C30H30O8.C2H4O2/c1-11(2)19-15-7-13(5)21(27(35)23(15)17(9-31)25(33)29(19)37)22-14(6)8-16-20(12(3)4)30(38)26(34)18(10-32)24(16)28(22)36;1-2(3)4/h7-12,33-38H,1-6H3;1H3,(H,3,4)

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 50 mg/mL (86.41 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

The natural racemic Gossypol has two enantiomers, namely the (-)-Gossypol and (S)-Gossypol ((+)-Gossypol) enantiomers. (+)-Gossypol and (-)-Gossypol binds to Bcl-2 or Bcl-xL with similar binding affinities. (-)-Gossypol is more potent than (+)-Gossypol in inhibition of cell growth and induction of apoptosis. The racemic form and each of the enantiomers of Gossypol are tested against UM-SCC-6 and UM-SCC-14A in 6-day MTT assays. (-)-Gossypol exhibits greater growth inhibition relative to (±)-Gossypol than (+)-Gossypol in both cell lines tested (P<0.001). An intermediate growth inhibitory effect is observed with (±)-Gossypol but this effect is only observed at the higher dose of Gossypol (10 μM, P<0.0001).

References:

1. Oliver CL, et al. In vitro effects of the BH3 mimetic, (-)-Gossypol, on head and neck squamous cell carcinoma cells. Clin Cancer Res. 2004 Nov 15;10(22):7757-63.

Products are for research use only. Not for human use.