Document Detail

Halogen substituents on the aromatic moiety of the tetracaine scaffold improve potency of cyclic nucleotide-gated channel block.
MedLine Citation:
PMID:  21944857     Owner:  NLM     Status:  MEDLINE    
A series of new tetracaine derivatives with substituents on the aromatic ring was prepared and evaluated for block of retinal rod cyclic nucleotide-gated (CNG) channels. Aromatic substitutions had little effect starting with the basic tetracaine scaffold, but electron-withdrawing substituents significantly improved the blocking potency of an octyl-tail derivative of tetracaine. In particular, halogen substitutions at either the 2- or 3-position on the ring resulted in compounds that were up to eight-fold more potent than the parent octyl-tail derivative and up to 50-fold more potent than tetracaine.
Sarah R Kirk; Adriana L Andrade; Kenneth Melich; Evan P Jackson; Elysia Cuellar; Jeffrey W Karpen
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't     Date:  2011-08-27
Journal Detail:
Title:  Bioorganic & medicinal chemistry letters     Volume:  21     ISSN:  1464-3405     ISO Abbreviation:  Bioorg. Med. Chem. Lett.     Publication Date:  2011 Nov 
Date Detail:
Created Date:  2011-10-10     Completed Date:  2012-01-31     Revised Date:  2014-09-19    
Medline Journal Info:
Nlm Unique ID:  9107377     Medline TA:  Bioorg Med Chem Lett     Country:  England    
Other Details:
Languages:  eng     Pagination:  6417-9     Citation Subset:  IM    
Copyright Information:
Copyright © 2011 Elsevier Ltd. All rights reserved.
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MeSH Terms
Cyclic Nucleotide-Gated Cation Channels / antagonists & inhibitors*
Halogens / chemistry*
Tetracaine / chemistry*
Grant Support
EY009275/EY/NEI NIH HHS; MH071625/MH/NIMH NIH HHS; R01 EY009275/EY/NEI NIH HHS; R01 EY009275-19/EY/NEI NIH HHS; R01 MH071625/MH/NIMH NIH HHS; R01 MH071625-02/MH/NIMH NIH HHS
Reg. No./Substance:
0/Cyclic Nucleotide-Gated Cation Channels; 0/Halogens; 0619F35CGV/Tetracaine

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