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A new series of the SMTP plasminogen modulators with a phenylamine-based side chain.

Abstract
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.
AuthorsHaruki Koide, Keiko Hasegawa, Naoko Nishimura, Ritsuko Narasaki, Keiji Hasumi
JournalThe Journal of antibiotics (J Antibiot (Tokyo)) Vol. 65 Issue 7 Pg. 361-7 (Jul 2012) ISSN: 1881-1469 [Electronic] England
PMID22511228 (Publication Type: Comparative Study, Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Aniline Compounds
  • Benzopyrans
  • Free Radical Scavengers
  • Pyrrolidinones
  • Plasminogen Activators
Topics
  • Aniline Compounds (chemistry, isolation & purification, pharmacology)
  • Benzopyrans (chemistry, isolation & purification, pharmacology)
  • Free Radical Scavengers (chemistry, isolation & purification, pharmacology)
  • Humans
  • Plasminogen Activators (chemistry, isolation & purification, pharmacology)
  • Pyrrolidinones (chemistry, isolation & purification, pharmacology)
  • Stachybotrys (metabolism)
  • Structure-Activity Relationship

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