Document Detail

Mercaptoimidazolylpropionic acid hydrobromide. Inhibition of tadpole collagenase and related properties.
MedLine Citation:
PMID:  209189     Owner:  NLM     Status:  MEDLINE    
A mercapto analogue of histidine (1), (RS)-2-mercapto-3-(5-imidazolyl)propionic acid (2), was prepared by treatment of (RS)-2-bromo-3-(5-imidazolyl)propionic acid with trithiocarbonate. Decomposition of the resulting intermediate with hydrochloric acid followed by Sephadex G-15 chromatography permitted isolation of 2 as a hydrobromide complex having unusual stability and properties as evidenced by IR and 1H NMR data. The potency of this complex in inhibiting tissue (Rana catesbiana) collagenase was estimated by radial diffusion assay. The amount of 2 required to produce 50% inhibition was 3.8 +/- 1.5 mM compared to 8.7 +/- 2.5 mM for cysteine. Preliminary tests of oxygen susceptibility, mutagenicity, and toxicity suggest that this substance may warrant study as a therapeutic agent for control of collagenase-linked corneal ulcerations.
J A Yankeelov; H A Parish; A F Spatola
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Publication Detail:
Type:  In Vitro; Journal Article; Research Support, U.S. Gov't, Non-P.H.S.; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  21     ISSN:  0022-2623     ISO Abbreviation:  J. Med. Chem.     Publication Date:  1978 Jul 
Date Detail:
Created Date:  1978-09-25     Completed Date:  1978-09-25     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  701-4     Citation Subset:  IM    
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MeSH Terms
Bacillus subtilis / drug effects
Chemical Phenomena
Histidine / analogs & derivatives*,  chemical synthesis,  pharmacology,  toxicity
Larva / enzymology
Magnetic Resonance Spectroscopy
Microbial Collagenase / antagonists & inhibitors*
Mutagens / chemical synthesis
Rana catesbeiana
Sulfhydryl Compounds / chemical synthesis,  pharmacology,  toxicity
Reg. No./Substance:
0/Mutagens; 0/Sulfhydryl Compounds; 71-00-1/Histidine; EC Collagenase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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