Skip to main content

Lund University Publications

LUND UNIVERSITY LIBRARIES

N-Conjugate prodrugs of galiellalactone

Escobar, Zilma LU ; Gidlöf, Ritha LU ; Johansson, Martin ; Hellsten, Rebecka LU and Sterner, Olov LU (2016) In Tetrahedron Letters 57(36). p.4090-4093
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.

Please use this url to cite or link to this publication:
author
; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Amine prodrug, Galiellalactone, Mechanism investigation, Michael addition, Prostate cancer
in
Tetrahedron Letters
volume
57
issue
36
pages
4 pages
publisher
Elsevier
external identifiers
  • scopus:84981298713
  • wos:000382338200027
ISSN
0040-4039
DOI
10.1016/j.tetlet.2016.07.094
language
English
LU publication?
yes
id
dfe643a9-0aac-49e0-912c-3b43aecf1089
date added to LUP
2016-11-08 08:56:53
date last changed
2025-10-14 13:09:48
@article{dfe643a9-0aac-49e0-912c-3b43aecf1089,
  abstract     = {{<p>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.</p>}},
  author       = {{Escobar, Zilma and Gidlöf, Ritha and Johansson, Martin and Hellsten, Rebecka and Sterner, Olov}},
  issn         = {{0040-4039}},
  keywords     = {{Amine prodrug; Galiellalactone; Mechanism investigation; Michael addition; Prostate cancer}},
  language     = {{eng}},
  month        = {{09}},
  number       = {{36}},
  pages        = {{4090--4093}},
  publisher    = {{Elsevier}},
  series       = {{Tetrahedron Letters}},
  title        = {{N-Conjugate prodrugs of galiellalactone}},
  url          = {{http://dx.doi.org/10.1016/j.tetlet.2016.07.094}},
  doi          = {{10.1016/j.tetlet.2016.07.094}},
  volume       = {{57}},
  year         = {{2016}},
}