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  • Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies.

Molecular modifications on carboxylic acid derivatives as potent histone deacetylase inhibitors: Activity and docking studies.

Bioorganic & medicinal chemistry (2009-06-13)
Gamze Bora-Tatar, Didem Dayangaç-Erden, Ayhan S Demir, Sevim Dalkara, Kemal Yelekçi, Hayat Erdem-Yurter
ABSTRACT

In the light of known HDAC inhibitors, 33 carboxylic acid derivatives were tested to understand the structural requirements for HDAC inhibition activity. Several modifications were applied to develop the structure-activity relationships of carboxylic acid HDAC inhibitors. HDAC inhibition activities were investigated in vitro by using HeLa nuclear extract in a fluorimetric assay. Molecular docking was also carried out for the human HDAC8 enzyme in order to predict inhibition activity and the 3D poses of inhibitor-enzyme complexes. Of these compounds, caffeic acid derivatives such as chlorogenic acid and curcumin were found to be highly potent compared to sodium butyrate, which is a well-known HDAC inhibitor.

MATERIALS
Product Number
Brand
Product Description

Chlorogenic acid, primary reference standard
Supelco
L-Valine, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
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DL-Tartaric acid, ≥99%
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8-Quinolinol, puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99% (perchloric acid titration)
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Salicylic acid, puriss. p.a., ≥99.0% (T)
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Vanillic acid, 97%
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4-Phenylbutyric acid, 99%
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1′-Hydroxy-2′-acetonaphthone, 99%
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8-Quinolinol, PESTANAL®, analytical standard
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Vanillic acid, ≥97%, FG
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Benzilic acid, ≥99%
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Salicylic acid, ≥99%, FG
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Mandelic acid, 99%
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DL-Tartaric acid, ReagentPlus®, 99%
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Hippuric acid, 98%
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L-Valine, from non-animal source, meets EP, JP, USP testing specifications, suitable for cell culture, 98.5-101.0%
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γ-Aminobutyric acid, BioXtra, ≥99%
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γ-Aminobutyric acid, ≥99%
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Salicylic acid, suitable for plant cell culture
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Chlorogenic acid, ≥95% (titration)
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2-Propylpentanoic acid
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L-Valine, reagent grade, ≥98% (HPLC)
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L-Valine, BioUltra, ≥99.5% (NT)
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2,3-Dihydroxybenzoic acid, 99%
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Salicylic acid, meets analytical specification of Ph. Eur., BP, USP, 99.5-100.5% (calc. to the dried substance)
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Salicylic acid, ACS reagent, ≥99.0%
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Salicylic acid, BioXtra, ≥99.0%
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Salicylic acid, ReagentPlus®, ≥99%
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Vanillic acid, purum, ≥97.0% (HPLC)
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Salicylic acid, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland