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Bioorg Med Chem. 2010 Aug 15;18(16):5795-806. doi: 10.1016/j.bmc.2010.07.003. Epub 2010 Jul 8.

Efficient synthesis and biological evaluation of demethyl geranylgeranoic acid derivatives.

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  • 1Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, Higashinada-ku, Kobe, Japan.


Synthetic retinoids have generated in the fields of dermatology and oncology due to their potent anti-proliferative and differentiation activities. We efficiently synthesized different demethyl geranylgeranoic acid (GGA) analogs, and evaluated their biological activities. Among the demethyl analogs synthesized, 3-demethyl derivative exhibited the highest anti-proliferative activity in HL-60 cells. In addition, a 3-demethyl derivative induced apoptosis more potently than 9Z-retinoic acid. These activities were due to the high binding affinity of 3-demethyl derivative for retinoid receptors. We found that, in a conjugated polyene system combined with a methyl substituent, the position of the methyl played an important role in the regulation of gene transcription and apoptosis-inducing activity. These results provided useful information on the structure-activity relationships of GGA derivatives that function as acyclic retinoic acid analogs. This information is likely to be useful in the development of new anti-cancer drugs.

Copyright 2010 Elsevier Ltd. All rights reserved.

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