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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

Sigma-Aldrich
Propionic acid, ≥99.5%
Sigma-Aldrich
trans-Ferulic acid, ≥99%
Sigma-Aldrich
Anthranilic acid, reagent grade, ≥98%
Sigma-Aldrich
trans-Cinnamic acid, natural, ≥99%, FCC, FG
Sigma-Aldrich
Citric acid, ACS reagent, ≥99.5%
Sigma-Aldrich
D-(−)-Tartaric acid, ReagentPlus®, 99%
Sigma-Aldrich
trans-Cinnamic acid, ≥99%, FG
Sigma-Aldrich
Indole-2-carboxylic acid, 98%
Sigma-Aldrich
trans-Ferulic acid, 99%
Sigma-Aldrich
trans-Cinnamic acid, ≥99%
Supelco
Caffeic acid, matrix substance for MALDI-MS, ≥99.0% (HPLC)
Supelco
Valeric acid, analytical standard
Sigma-Aldrich
Propionic acid, ACS reagent, ≥99.5%
Sigma-Aldrich
Isovaleric acid, 99%
Sigma-Aldrich
Isobutyric acid, ≥99%, FCC, FG
Sigma-Aldrich
Isobutyric acid, natural, ≥99%, FCC, FG
Sigma-Aldrich
trans-Cinnamic acid, 97%
Sigma-Aldrich
Butyric acid, ≥99%, FG
Sigma-Aldrich
Valeric acid, ≥99%
Sigma-Aldrich
Butyric acid, natural, ≥99%, FCC, FG
Supelco
Propionic acid, analytical standard
Sigma-Aldrich
Propionic acid, puriss. p.a., ≥99.5% (GC)
Sigma-Aldrich
Succinic acid, purum p.a., ≥99.0% (T)
Supelco
trans-Ferulic acid, matrix substance for MALDI-MS, ≥99.0% (HPLC)
Sigma-Aldrich
Isobutyric acid, puriss. p.a., ≥99.5%
Sigma-Aldrich
Sorbic acid, tested according to Ph. Eur.
Sigma-Aldrich
D-(−)-Tartaric acid, puriss., unnatural form, ≥99.0% (T)
Sigma-Aldrich
Sodium DL-lactate, ReagentPlus®, ≥99.0% (NT)
Sigma-Aldrich
Citric acid, BioUltra, anhydrous, ≥99.5% (T)
Sigma-Aldrich
3,4-Dihydroxyhydrocinnamic acid, 98%