Semisynthetic neoboutomellerone derivatives as ubiquitin-proteasome pathway inhibitors

Beck, Josephine, Guminski, Yves, Long, Christophe, Marcourt, Laurence, Derguini, Fadila, Plisson, Fabien, Grondin, Antonio, Vandenberghe, Isabelle, Vispe, Stephane, Brel, Viviane, Aussagues, Yannick, Ausseil, Frederic, Arimondo, Paola B., Massiot, Georges, Sautel, Francois and Cantagrel, Frederic (2012) Semisynthetic neoboutomellerone derivatives as ubiquitin-proteasome pathway inhibitors. Bioorganic and Medicinal Chemistry, 20 2: 819-831. doi:10.1016/j.bmc.2011.11.066

Author Beck, Josephine
Guminski, Yves
Long, Christophe
Marcourt, Laurence
Derguini, Fadila
Plisson, Fabien
Grondin, Antonio
Vandenberghe, Isabelle
Vispe, Stephane
Brel, Viviane
Aussagues, Yannick
Ausseil, Frederic
Arimondo, Paola B.
Massiot, Georges
Sautel, Francois
Cantagrel, Frederic
Title Semisynthetic neoboutomellerone derivatives as ubiquitin-proteasome pathway inhibitors
Journal name Bioorganic and Medicinal Chemistry   Check publisher's open access policy
ISSN 0968-0896
Publication date 2012-01-15
Year available 2011
Sub-type Article (original research)
DOI 10.1016/j.bmc.2011.11.066
Open Access Status DOI
Volume 20
Issue 2
Start page 819
End page 831
Total pages 13
Editor Herman Overkleeft
Place of publication Kidlington, Oxford, United Kingdom
Publisher Pergamon
Language eng
Formatted abstract
The interesting pharmacological properties of neoboutomellerones 1 and 2 were the basis for the assembly of a small library of analogues consisting of natural products isolated from the plant Neoboutonia melleri and of semisynthetic derivatives. As the two enone systems (C23–C24a and C1–C3) and the two hydroxyls groups (C22 and C26) of neoboutomellerones are required for activity, modifications were focused on these functional groups. Biological evaluation by using a cellular assay for proteasome activity provided clues regarding the mechanism of action of these natural products and synthetic derivatives. Certain neoboutomellerone derivatives inhibited the proliferation of human WM-266-4 melanoma tumor cells at submicromolar concentration and warrant evaluation as anticancer agents.
Keyword Cycloartane
Neoboutonia melleri
Natural product
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status Non-UQ
Additional Notes Available online 8 December 2011. Special issue: Chemical Proteomics.

Document type: Journal Article
Sub-type: Article (original research)
Collections: Non HERDC
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Created: Mon, 03 Sep 2012, 19:13:42 EST by Susan Allen on behalf of Institute for Molecular Bioscience