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A new series of the SMTP plasminogen modulators with a phenylamine-based side chain
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A new series of the SMTP plasminogen modulators with a phenylamine-based side chain
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Journal Article
A new series of the SMTP plasminogen modulators with a phenylamine-based side chain
2012
Overview
SMTPs are a family of small-molecule plasminogen modulators that enhance plasminogen activation. SMTP-7, one of the most potent congeners, is effective in treating thrombotic cerebral infarction. The SMTP molecule consists of a tricyclic γ-lactam moiety, a geranylmethyl group, and an
N
-linked side chain. The presence of both an aromatic group and a negatively ionizable group in the
N
-linked side chain is crucial for activity. Investigations of the congeners with a phenylglycine-based side chain suggest that a phenolic hydroxy group affects potency. In this study, we isolate and characterize a series of novel SMTP congeners with a phenylamine-based
N
-linked side chain. Of the 11 congeners isolated, SMTP-19 (with a 4-phenylcarboxylic acid moiety), SMTP-22 (with a 3-hydroxyphenyl-4-carboxylic acid moiety) and SMTP-25 (with a 2-hydroxyphenyl-3-carboxylic acid moiety) are as potent as SMTP-7 in plasminogen-modulating activity. Their isomers with a carboxylic acid group and/or a phenolic hydroxy group at different positions have <40% of the activity of these congeners. Both SMTP-22 and SMTP-25 have >1.7 times more oxygen radical absorbance capacity as compared with SMTP-7.
Publisher
Nature Publishing Group UK,Nature Publishing Group
Subject
/ Aniline Compounds - chemistry
/ Aniline Compounds - isolation & purification
/ Aniline Compounds - pharmacology
/ Benzopyrans - isolation & purification
/ Biomedical and Life Sciences
/ Free Radical Scavengers - chemistry
/ Free Radical Scavengers - isolation & purification
/ Free Radical Scavengers - pharmacology
/ Humans
/ Phenols
/ Plasminogen Activators - chemistry
/ Plasminogen Activators - isolation & purification
/ Plasminogen Activators - pharmacology
/ Pyrrolidinones - isolation & purification
/ Pyrrolidinones - pharmacology
