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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.

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author
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
2017-01-01 08:38:57
@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},
  keyword      = {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},
  volume       = {57},
  year         = {2016},
}