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United States Department of Agriculture

Agricultural Research Service

Research Project: CHEMISTRY OF NATURAL PRODUCTS FOR PEST MANAGEMENT AND CROP DEVELOPMENT

Location: Natural Products Utilization Research

Title: Synthesis and Biological Evaluation of Retinoid-Chalcones as Inhibitors of Colon Cancer Cell Growth

Authors
item Mizuno, Cassia
item Paul, Shiby -
item Suh, Nanjoo -
item Rimando, Agnes

Submitted to: Bioorganic and Medicinal Chemistry Letters
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: October 8, 2010
Publication Date: October 14, 2010
Citation: Mizuno, C.S., Paul, S., Suh, N., Rimando, A.M. 2010. Synthesis and Biological Evaluation of Retinoid-Chalcones as Inhibitors of Colon Cancer Cell Growth. Bioorganic and Medicinal Chemistry Letters. 20:7385-7387.

Interpretive Summary: Colon cancer is the third most common type of cancer found in the United States. It is predicted that this year more than 51,000 deaths will occur in this country because of colon cancer. Chalcones are natural compounds commonly found in edible plants. The presence of these compounds in fruits and vegetables has been related to the health benefits of these types of food. Retinoids are compounds with similar structure as vitamin A and their ability to treat cancer have been explored. Thus, the features of chalcones and retinoids were combined to synthesize a class of compounds called retinoid-chalcones. Nineteen retinoid-chalcones were synthesized and tested for the inhibition of growth of a colon cancer cell line. Among the compounds, one was identified as having good activity against colon cancer cell growth.

Technical Abstract: Based on the observed anticancer activity of chalcones and retinoids, a novel class of retinoid-chalcone hybrids were designed and synthesized. As part of our ongoing studies to discover natural product based anticancer compounds, the retinoid-chalcone hybrids were tested against the colon cancer cell line HT-29. Retinoid-like moiety was introduced through Friedel-Crafts acylation of toluene. Among the synthesized compounds the cyano derivative (E)-3-(3-oxo-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-enyl)benzonitrile showed submicromolar inhibitory activity with an IC50 of 0.66 µM.

Last Modified: 4/18/2014