Arylamide derivatives as peptidomimetic inhibitors of calmodulin

Hang Yin; Kendra K. Frederick; Dahui Liu; A. Joshua Wand; William F. DeGrado

doi:10.1021/ol052478j

Arylamide derivatives as peptidomimetic inhibitors of calmodulin

Hang Yin, Kendra K. Frederick, Dahui Liu, A. Joshua Wand, William F. DeGrado

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37 Scopus citations

Abstract

Many peptides bind to calmodulin (CaM) in a helical conformation. Here we describe a group of synthetic inhibitors of CaM based on an arylamide scaffold that is intended to mimic smMLCK, a CaM-binding helical peptide. Compound 1 showed a K _i value of 7.10 ± 1.48 nM in a fluorescence polarization assay that monitors the strong association of CaM and its peptide ligand mastoparan X. ( ¹H, ¹⁵N)-HSQC NMR spectroscopy experiments suggested that 1 binds to CaM in an analogous fashion to that of smMLCK.

Original language	English (US)
Pages (from-to)	223-225
Number of pages	3
Journal	Organic Letters
Volume	8
Issue number	2
DOIs	https://doi.org/10.1021/ol052478j
State	Published - Jan 19 2006

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "Many peptides bind to calmodulin (CaM) in a helical conformation. Here we describe a group of synthetic inhibitors of CaM based on an arylamide scaffold that is intended to mimic smMLCK, a CaM-binding helical peptide. Compound 1 showed a K i value of 7.10 ± 1.48 nM in a fluorescence polarization assay that monitors the strong association of CaM and its peptide ligand mastoparan X. ( 1H, 15N)-HSQC NMR spectroscopy experiments suggested that 1 binds to CaM in an analogous fashion to that of smMLCK.",

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AU - Yin, Hang

AU - Frederick, Kendra K.

AU - Liu, Dahui

AU - Wand, A. Joshua

AU - DeGrado, William F.

PY - 2006/1/19

Y1 - 2006/1/19

N2 - Many peptides bind to calmodulin (CaM) in a helical conformation. Here we describe a group of synthetic inhibitors of CaM based on an arylamide scaffold that is intended to mimic smMLCK, a CaM-binding helical peptide. Compound 1 showed a K i value of 7.10 ± 1.48 nM in a fluorescence polarization assay that monitors the strong association of CaM and its peptide ligand mastoparan X. ( 1H, 15N)-HSQC NMR spectroscopy experiments suggested that 1 binds to CaM in an analogous fashion to that of smMLCK.

AB - Many peptides bind to calmodulin (CaM) in a helical conformation. Here we describe a group of synthetic inhibitors of CaM based on an arylamide scaffold that is intended to mimic smMLCK, a CaM-binding helical peptide. Compound 1 showed a K i value of 7.10 ± 1.48 nM in a fluorescence polarization assay that monitors the strong association of CaM and its peptide ligand mastoparan X. ( 1H, 15N)-HSQC NMR spectroscopy experiments suggested that 1 binds to CaM in an analogous fashion to that of smMLCK.

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JO - Organic Letters

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Arylamide derivatives as peptidomimetic inhibitors of calmodulin

Abstract

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