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United States Department of Agriculture

Agricultural Research Service

Title: Cytotoxicity of Enantiomers of Gossypol Schiff's Bases and Optical Stability of Gossypolone

Authors
item Dao, Vi-Thuy - INSTITUT CURIE
item Dowd, Michael
item Martin, Marie-Therese - INSTITUT DE CHIMIE
item Gaspard, Christiane - INSTITUT DE CHIMIE
item Mayer, Michel - INSTITUT DE CHIMIE
item Michelot, Robert - INSTITUT DE CHIMIE

Submitted to: European Journal of Medicinal Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: April 1, 2004
Publication Date: April 17, 2004
Citation: Dao, V-T., Dowd, M.K., Martin, M-T., Gaspard, C., Mayer, M., Michelot, R.J. 2004. Cytotoxicity of enantiomers of gossypol schiff's bases and optical stability of gossypolone. European Journal of Medicinal Chemistry. 39(7):619-624.

Interpretive Summary: Derivatives of gossypol were prepared and tested for anti-cancer activity against three cells lines and included one line known to have developed resistance against some cancer drugs. The compounds proved to be toxic against cancer cells and several of the derivatives were more toxic than gossypol. The derivatives were also toxic to the drug resistant cell line. The results will be of interest to researchers studying gossypol as a drug to fight cancer.

Technical Abstract: Optical Schiff's bases of gossypol were prepared with chiral gossypol and ethylamine. As has been similarly observed among the gossypol enantiomers, the (-)-gossypol ethylimine was more active than either the (+)-gossypol ethylimine or the racemic gossypol ethylimine against KB and MCF7 cells. Gossypolone was also observed to be more toxic than gossypol against both cell lines. All of the gossypol products tested showed comparable toxicity toward MCF7/ADR (adriblastine-resistant) cells. Attempts at producing chiral gossypolone from chiral gossypol failed because of rapid racemization. In addition, the Shiff's base derivatives of gossypolone formed with R-(+)-2-amino-3-phenyl-1-propanol could only be separated at reduced temperature, indicating that gossypolone Schiff's bases are less optical stable than gossypol Schiff's bases.

Last Modified: 8/2/2014
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