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Synthesis and biological evaluation of histone deacetylase inhibitors that are based on FR235222: a cyclic tetrapeptide scaffold.

ABSTRACT: We outline the synthesis of six novel derivatives that are based on a recently discovered HDAC inhibitor FR235222. Our work is the first report utilizing a novel binding element, guanidine, as metal coordinators in HDAC inhibitors. Further, we demonstrate that these compounds show cytotoxicity that parallels their ability to inhibit deacetylase activity, and that the most potent compounds maintain an L-Phe at position 1, and a D-Pro at position 4. Both inhibition of HDAC activity and cytotoxicity against the pancreatic cancer cell line BxPC3 are exhibited by these compounds, establishing that a guanidine unit can be utilized successfully to inhibit HDAC activity.

SUBMITTER: Singh EK 

PROVIDER: S-EPMC2593638 | biostudies-literature | 2008 Apr

REPOSITORIES: biostudies-literature

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Synthesis and biological evaluation of histone deacetylase inhibitors that are based on FR235222: a cyclic tetrapeptide scaffold.

Singh Erinprit K EK   Ravula Suchitra S   Pan Chung-Mao CM   Pan Po-Shen PS   Vasko Robert C RC   Lapera Stephanie A SA   Weerasinghe Sujith V W SV   Pflum Mary Kay H MK   McAlpine Shelli R SR  

Bioorganic & medicinal chemistry letters 20080320 8

We outline the synthesis of six novel derivatives that are based on a recently discovered HDAC inhibitor FR235222. Our work is the first report utilizing a novel binding element, guanidine, as metal coordinators in HDAC inhibitors. Further, we demonstrate that these compounds show cytotoxicity that parallels their ability to inhibit deacetylase activity, and that the most potent compounds maintain an L-Phe at position 1, and a D-Pro at position 4. Both inhibition of HDAC activity and cytotoxicit  ...[more]

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