N-Conjugate prodrugs of galiellalactone
(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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https://lup.lub.lu.se/record/dfe643a9-0aac-49e0-912c-3b43aecf1089
- author
- Escobar, Zilma LU ; Gidlöf, Ritha LU ; Johansson, Martin ; Hellsten, Rebecka LU and Sterner, Olov LU
- organization
- publishing date
- 2016-09-07
- 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
-
- wos:000382338200027
- scopus:84981298713
- 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
- 2024-04-19 12:07:24
@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}}, }