dc.contributor.author |
Wang, J |
en |
dc.contributor.author |
Bourguet-Kondracki, M-L |
en |
dc.contributor.author |
Longeon, A |
en |
dc.contributor.author |
Dubois, J |
en |
dc.contributor.author |
Valentin, A |
en |
dc.contributor.author |
Copp, Brent |
en |
dc.coverage.spatial |
England |
en |
dc.date.accessioned |
2017-11-28T01:37:04Z |
en |
dc.date.available |
2010-12-13 |
en |
dc.date.issued |
2011-02-15 |
en |
dc.identifier.citation |
Bioorganic and Medicinal Chemistry Letters, 21(4):1261-1264, 15 Feb 2011 |
en |
dc.identifier.issn |
0960-894X |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/36583 |
en |
dc.description.abstract |
The electrophilic reactivity of the bioactive marine sponge natural product halenaquinone has been investigated by reaction with the biomimetic nucleophiles N-acetyl-L-cysteine and N(α)-acetyl-L-lysine. While cysteine reacted at the vacant quinone positions C-14 and C-15, lysine was found to react preferentially at the keto-furan position C-1. A small library of analogues was prepared by reaction of halenaquinone with primary amines, and evaluated against a range of biological targets including phospholipase A(2), farnesyltransferases (FTases) and Plasmodium falciparum. Geranylamine analogue 11 exhibited the most potent activity towards FTases (IC(50) 0.017-0.031 μM) and malaria (IC(50) 0.53-0.62 μM). |
en |
dc.description.uri |
https://www.ncbi.nlm.nih.gov/pubmed/21256013 |
en |
dc.language |
English |
en |
dc.publisher |
Elsevier |
en |
dc.relation.ispartofseries |
Bioorganic and Medicinal Chemistry Letters |
en |
dc.rights |
Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://sherpa.ac.uk/romeo/issn/0960-894X/
https://www.elsevier.com/about/our-business/policies/sharing |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
en |
dc.subject |
Acetylcysteine |
en |
dc.subject |
Animals |
en |
dc.subject |
Bees |
en |
dc.subject |
Biomimetic Materials |
en |
dc.subject |
Farnesyltranstransferase |
en |
dc.subject |
Humans |
en |
dc.subject |
Phospholipase A2 Inhibitors |
en |
dc.subject |
Phospholipases A2 |
en |
dc.subject |
Plasmodium falciparum |
en |
dc.subject |
Porifera |
en |
dc.subject |
Quinones |
en |
dc.title |
Chemical and biological explorations of the electrophilic reactivity of the bioactive marine natural product halenaquinone with biomimetic nucleophiles |
en |
dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1016/j.bmcl.2010.12.056 |
en |
pubs.issue |
4 |
en |
pubs.begin-page |
1261 |
en |
pubs.volume |
21 |
en |
dc.rights.holder |
Copyright: Elsevier |
en |
dc.identifier.pmid |
21256013 |
en |
pubs.author-url |
http://www.sciencedirect.com/science/article/pii/S0960894X10018202 |
en |
pubs.end-page |
1264 |
en |
pubs.publication-status |
Published |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
en |
pubs.subtype |
Article |
en |
pubs.elements-id |
202975 |
en |
pubs.org-id |
Science |
en |
pubs.org-id |
Chemistry |
en |
pubs.org-id |
Science Research |
en |
pubs.org-id |
Maurice Wilkins Centre (2010-2014) |
en |
dc.identifier.eissn |
1464-3405 |
en |
dc.identifier.pii |
S0960-894X(10)01820-2 |
en |
pubs.record-created-at-source-date |
2017-11-28 |
en |
pubs.online-publication-date |
2010-12-16 |
en |
pubs.dimensions-id |
21256013 |
en |