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N-Conjugate prodrugs of galiellalactone

Author:
  • Zilma Escobar
  • Ritha Gidlöf
  • Martin Johansson
  • Rebecka Hellsten
  • Olov Sterner
Publishing year: 2016-09-07
Language: English
Pages: 4090-4093
Publication/Series: Tetrahedron Letters
Volume: 57
Issue: 36
Document type: Journal article
Publisher: Elsevier

Abstract english

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.

Keywords

  • Biochemistry and Molecular Biology
  • Cancer and Oncology
  • Amine prodrug
  • Galiellalactone
  • Mechanism investigation
  • Michael addition
  • Prostate cancer

Other

Published
  • Urological cancer, Malmö
  • ISSN: 0040-4039
Olov Sterner
E-mail: olov [dot] sterner [at] science [dot] lu [dot] se

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Faculty of Science

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