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Inhibition of PCAF Histone Acetyltransferase, Cytotoxicity and Cell Permeability of 2-Acylamino-1-(3- or 4-Carboxy-phenyl)benzamides

College of Pharmacy, Catholic University of Daegu, Hayang 712-702, Korea
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Molecules 2012, 17(11), 13116-13131; https://doi.org/10.3390/molecules171113116
Received: 28 August 2012 / Revised: 12 September 2012 / Accepted: 1 November 2012 / Published: 5 November 2012
Small molecule HAT inhibitors are useful tools to unravel the role of histone acetyltransferases (HATs) in the cell and they also have relevance in oncology. We synthesized a series of 2-acylamino-1-(3- or 4-carboxyphenyl)benzamides 819 bearing C6, C8, C10, C12, C14, and C16 acyl chains at the 2-amino position of 2-aminobenzoic acid. Enzyme inhibition of these compounds was investigated using in vitro PCAF HAT assays. The inhibitory activities of compounds 810, 16, and 19 were similar to that of anacardic acid, and 17 was found to be more active than anacardic acid at 100 μM. Compounds 1115 showed the low inhibitory activity on PCAF HAT. The cytotoxicity of the synthesized compounds was evaluated by SRB (sulforhodamine B) assay against seven human cancer cell lines: HT-29 (colon), HCT-116 (colon), MDA-231 (breast), A549 (lung), Hep3B (hepatoma), HeLa (cervical) and Caki (kidney) and one normal cell line (HSF). Compound 17 was more active than anacardic acid against human colon cancer (HCT 116, IC50: 29.17 μM), human lung cancer (A549, IC50: 32.09 μM) cell lines. 18 was more active than anacardic acid against human colon cancer (HT-29, IC50: 35.49 μM and HCT 116, IC50: 27.56 μM), human lung cancer (A549, IC50: 30.69 μM), and human cervical cancer (HeLa, IC50: 34.41 μM) cell lines. The apparent permeability coefficient (Papp, cm/s) values of two compounds (16 and 17) were evaluated as 68.21 and 71.48 × 10−6 cm/s by Caco-2 cell permeability assay. View Full-Text
Keywords: histone acetyltransferase (HAT); p300/CBP associated factor (PCAF); cytotoxicity; 2-acylaminobenzamide; Caco-2 cell permeability histone acetyltransferase (HAT); p300/CBP associated factor (PCAF); cytotoxicity; 2-acylaminobenzamide; Caco-2 cell permeability
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Park, W.J.; Ma, E. Inhibition of PCAF Histone Acetyltransferase, Cytotoxicity and Cell Permeability of 2-Acylamino-1-(3- or 4-Carboxy-phenyl)benzamides. Molecules 2012, 17, 13116-13131.

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