N-Conjugate prodrugs of galiellalactone

Research output: Contribution to journalArticle

Abstract

A series of amine adducts of the fungal metabolite galiellalactone (1) were prepared by reacting galiellalactone with different secondary amines via a Lewis acid catalyzed Michael addition. The adducts were assayed for in vitro effects toward prostate cancer cell lines and found to possess a similar ability to inhibit cell proliferation as galiellalactone itself. It was found that the Michael addition of amines to 1 is a reversible reaction, releasing 1 at different rates depending on the conditions, and that the adducts are potential prodrugs of galiellalactone. The chemical stability of the amine adducts is especially sensitive to pH, increasing at a lower pH.

Details

Authors
Organisations
External organisations
  • Glactone Pharma AB
Research areas and keywords

Subject classification (UKÄ) – MANDATORY

  • Biochemistry and Molecular Biology
  • Cancer and Oncology

Keywords

  • Amine prodrug, Galiellalactone, Mechanism investigation, Michael addition, Prostate cancer
Original languageEnglish
Pages (from-to)4090-4093
Number of pages4
JournalTetrahedron Letters
Volume57
Issue number36
Publication statusPublished - 2016 Sep 7
Publication categoryResearch
Peer-reviewedYes