Coumarin-based prodrugs. Part 3: Structural effects on the release kinetics of esterase-sensitive prodrugs of amines

Binghe Wang, Huijuan Zhang, Ailian Zheng, Wei Wang

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

To study the structural effects on the release kinetics of a coumarin- based esterase-sensitive prodrug system, two series of compounds with varying structural features of the ester 'trigger' part and the amine 'drug' part were synthesized. The half-lives of the nine model prodrugs in the presence of porcine liver esterase ranged from about 2 min to 190 min. The steric bulkiness of the acyl group seems to have only a very minor effect on the half-lives of the esterase-triggered release of amines from the model prodrugs. The rate of the lactonization depends on the steric and electronic properties of the amine moiety.

Original languageEnglish (US)
Pages (from-to)417-426
Number of pages10
JournalBioorganic and Medicinal Chemistry
Volume6
Issue number4
DOIs
StatePublished - Apr 1998
Externally publishedYes

Keywords

  • Coumarin
  • Coumarinic acid
  • Esterase
  • Prodrug
  • Structural effect

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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