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==N-Benzyl-indolo carboxylic acids: Design and synthesis of potent and selective adipocyte Fatty-Acid Binding Protein (A-FABP) inhibitors== | ==N-Benzyl-indolo carboxylic acids: Design and synthesis of potent and selective adipocyte Fatty-Acid Binding Protein (A-FABP) inhibitors== | ||
<StructureSection load='3fr4' size='340' side='right' caption='[[3fr4]], [[Resolution|resolution]] 2.16Å' scene=''> | <StructureSection load='3fr4' size='340' side='right'caption='[[3fr4]], [[Resolution|resolution]] 2.16Å' scene=''> | ||
== Structural highlights == | == Structural highlights == | ||
<table><tr><td colspan='2'>[[3fr4]] is a 1 chain structure with sequence from [ | <table><tr><td colspan='2'>[[3fr4]] is a 1 chain structure with sequence from [https://en.wikipedia.org/wiki/Human Human]. Full crystallographic information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=3FR4 OCA]. For a <b>guided tour on the structure components</b> use [https://proteopedia.org/fgij/fg.htm?mol=3FR4 FirstGlance]. <br> | ||
</td></tr><tr id='ligand'><td class="sblockLbl"><b>[[Ligand|Ligands:]]</b></td><td class="sblockDat"><scene name='pdbligand=F8A:9-[2-(TRIFLUOROMETHYL)BENZYL]-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-8-CARBOXYLIC+ACID'>F8A</scene></td></tr> | </td></tr><tr id='ligand'><td class="sblockLbl"><b>[[Ligand|Ligands:]]</b></td><td class="sblockDat" id="ligandDat"><scene name='pdbligand=F8A:9-[2-(TRIFLUOROMETHYL)BENZYL]-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-8-CARBOXYLIC+ACID'>F8A</scene></td></tr> | ||
<tr id='related'><td class="sblockLbl"><b>[[Related_structure|Related:]]</b></td><td class="sblockDat">[[3fr2|3fr2]], [[3fr5|3fr5]]</td></tr> | <tr id='related'><td class="sblockLbl"><b>[[Related_structure|Related:]]</b></td><td class="sblockDat"><div style='overflow: auto; max-height: 3em;'>[[3fr2|3fr2]], [[3fr5|3fr5]]</div></td></tr> | ||
<tr id='gene'><td class="sblockLbl"><b>[[Gene|Gene:]]</b></td><td class="sblockDat">FABP4 ([ | <tr id='gene'><td class="sblockLbl"><b>[[Gene|Gene:]]</b></td><td class="sblockDat">FABP4 ([https://www.ncbi.nlm.nih.gov/Taxonomy/Browser/wwwtax.cgi?mode=Info&srchmode=5&id=9606 HUMAN])</td></tr> | ||
<tr id='resources'><td class="sblockLbl"><b>Resources:</b></td><td class="sblockDat"><span class='plainlinks'>[ | <tr id='resources'><td class="sblockLbl"><b>Resources:</b></td><td class="sblockDat"><span class='plainlinks'>[https://proteopedia.org/fgij/fg.htm?mol=3fr4 FirstGlance], [http://oca.weizmann.ac.il/oca-bin/ocaids?id=3fr4 OCA], [https://pdbe.org/3fr4 PDBe], [https://www.rcsb.org/pdb/explore.do?structureId=3fr4 RCSB], [https://www.ebi.ac.uk/pdbsum/3fr4 PDBsum], [https://prosat.h-its.org/prosat/prosatexe?pdbcode=3fr4 ProSAT]</span></td></tr> | ||
</table> | </table> | ||
== Function == | == Function == | ||
[[ | [[https://www.uniprot.org/uniprot/FABP4_HUMAN FABP4_HUMAN]] Lipid transport protein in adipocytes. Binds both long chain fatty acids and retinoic acid. Delivers long-chain fatty acids and retinoic acid to their cognate receptors in the nucleus (By similarity). | ||
== Evolutionary Conservation == | == Evolutionary Conservation == | ||
[[Image:Consurf_key_small.gif|200px|right]] | [[Image:Consurf_key_small.gif|200px|right]] | ||
| Line 32: | Line 32: | ||
==See Also== | ==See Also== | ||
*[[Fatty acid-binding protein|Fatty acid-binding protein]] | *[[Fatty acid-binding protein 3D structures|Fatty acid-binding protein 3D structures]] | ||
== References == | == References == | ||
<references/> | <references/> | ||
| Line 38: | Line 38: | ||
</StructureSection> | </StructureSection> | ||
[[Category: Human]] | [[Category: Human]] | ||
[[Category: Large Structures]] | |||
[[Category: Axen, E]] | [[Category: Axen, E]] | ||
[[Category: Barf, T]] | [[Category: Barf, T]] | ||
Revision as of 11:08, 2 March 2022
N-Benzyl-indolo carboxylic acids: Design and synthesis of potent and selective adipocyte Fatty-Acid Binding Protein (A-FABP) inhibitorsN-Benzyl-indolo carboxylic acids: Design and synthesis of potent and selective adipocyte Fatty-Acid Binding Protein (A-FABP) inhibitors
Structural highlights
Function[FABP4_HUMAN] Lipid transport protein in adipocytes. Binds both long chain fatty acids and retinoic acid. Delivers long-chain fatty acids and retinoic acid to their cognate receptors in the nucleus (By similarity). Evolutionary Conservation Check, as determined by ConSurfDB. You may read the explanation of the method and the full data available from ConSurf. Publication Abstract from PubMedSmall molecule inhibitors of adipocyte fatty-acid binding protein (A-FABP) have gained renewed interest following the recent publication of pharmacologically beneficial effects of such inhibitors. Despite the potential utility of selective A-FABP inhibitors within the fields of metabolic disease, inflammation and atherosclerosis, there are few examples of useful A-FABP inhibitors in the public domain. Herein, we describe the optimization of N-benzyl-tetrahydrocarbazole derivatives through the use of co-crystal structure guided medicinal chemistry efforts. This led to the identification of a potent and selective class of A-FABP inhibitors as illustrated by N-benzyl-hexahydrocyclohepta[b]indole 30. N-Benzyl-indolo carboxylic acids: Design and synthesis of potent and selective adipocyte fatty-acid binding protein (A-FABP) inhibitors.,Barf T, Lehmann F, Hammer K, Haile S, Axen E, Medina C, Uppenberg J, Svensson S, Rondahl L, Lundback T Bioorg Med Chem Lett. 2009 Mar 15;19(6):1745-8. Epub 2009 Jan 30. PMID:19217286[1] From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine. See AlsoReferences
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