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PMID: 22263962 Published · ppublish English Journal Article Research Support, Non-U.S. Gov't

Dynamic combinatorial mass spectrometry leads to inhibitors of a 2-oxoglutarate-dependent nucleic acid demethylase.

Journal of medicinal chemistry ·Vol. 55 ·No. 5 ·2012-03-08 ·Pages 2173-84

Woon EC, Demetriades M, Bagg EA, Aik W, Krylova SM, Ma JH, Chan M, Walport LJ, Wegman DW, Dack KN, McDonough MA, Krylov SN, Schofield CJ

Abstract

2-Oxoglutarate-dependent nucleic acid demethylases are of biological interest because of their roles in nucleic acid repair and modification. Although some of these enzymes are linked to physiology, their regulatory roles are unclear. Hence, there is a desire to develop selective inhibitors for them; we report studies on AlkB, which reveal it as being amenable to selective inhibition by small molecules. Dynamic combinatorial chemistry linked to mass spectrometric analyses (DCMS) led to the identification of lead compounds, one of which was analyzed by crystallography. Subsequent structure-guided studies led to the identification of inhibitors of improved potency, some of which were shown to be selective over two other 2OG oxygenases. The work further validates the use of the DCMS method and will help to enable the development of inhibitors of nucleic acid modifying 2OG oxygenases both for use as functional probes and, in the longer term, for potential therapeutic use.

MeSH Terms
Catalytic Domain Combinatorial Chemistry Techniques Crystallography, X-Ray Cysteine/analogs & derivatives,chemical synthesis,chemistry Enzyme Assays Escherichia coli Proteins/antagonists & inhibitors,chemistry Ferrous Compounds/chemistry,metabolism Ketoglutaric Acids/chemistry,metabolism Mixed Function Oxygenases/antagonists & inhibitors,chemistry Models, Molecular Protein Binding Pyridines/chemical synthesis,chemistry Quinolines/chemical synthesis,chemistry Spectrometry, Mass, Electrospray Ionization Structure-Activity Relationship
Chemicals
Escherichia coli Proteins Ferrous Compounds Ketoglutaric Acids Pyridines Quinolines hydroxypyridines N-oxalylcysteine Mixed Function Oxygenases AlkB protein, E coli Cysteine
Authors & Affiliations
13 authors, click to expand affiliations / ORCID
Woon Esther C Y
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK.
Demetriades Marina
Bagg Eleanor A L
Aik WeiShen
Krylova Svetlana M
Ma Jerome H Y
Chan MunChiang
Walport Louise J
Wegman David W
Dack Kevin N
McDonough Michael A
Krylov Sergey N
Schofield Christopher J
Article Info
Journal
Journal of medicinal chemistry
Abbr.
J Med Chem
ISSN
1520-4804
Published
2012-03-08
Epub
2012-00-22
Pages
2173-84
Language
English
Region
United States
NLM ID
9716531
Subset
IM
Grants
Wellcome Trust · United Kingdom
Biotechnology and Biological Sciences Research Council · United Kingdom
Databases
PDB
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