Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 17, Issue 18, Pages 6613-6619Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2009.07.075
Keywords
SERCA; Structure-activity relationship; GOLD; Ligand docking; Prostate cancer; Calcium pump; Enzyme inhibition; Organic synthesis; Medicinal chemistry
Funding
- Kentucky Biomedical Research Infrastructure Network [P20RR016481-08]
- Research Corporation [6843]
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Analogues of the compound 2,5-di-tert-butylhydroquinone (BHQ) are capable of inhibiting the enzyme sarco/endoplasmic reticulum ATPase (SERCA) in the low micromolar and submicromolar concentration ranges. Not only are SERCA inhibitors valuable research tools, but they also have potential medicinal value as agents against prostate cancer. This study describes the synthesis of 13 compounds representing several classes of BHQ analogues, such as hydroquinones with a single aromatic substituent, symmetrically and unsymmetrically disubstituted hydroquinones, and hydroquinones with x-amino acid tethers attached to their hydroxyl groups. Structure-activity relationships were established by measuring the inhibitory potencies of all synthesized compounds in bioassays. The assays were complemented by computational ligand docking for an analysis of the relevant ligand/receptor interactions. (C) 2009 Elsevier Ltd. All rights reserved.
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