A search for kinase inhibitors and antibacterial agents: bromopyrrolo-2-aminoimidazoles from a deep-water Great Australian Bight sponge, Axinella sp.

Zhang, Hua, Khalil, Zeinab, Conte, Melissa M., Plisson, Fabien and Capon, Robert J. (2012) A search for kinase inhibitors and antibacterial agents: bromopyrrolo-2-aminoimidazoles from a deep-water Great Australian Bight sponge, Axinella sp.. Tetrahedron Letters, 53 29: 3784-3787.


Author Zhang, Hua
Khalil, Zeinab
Conte, Melissa M.
Plisson, Fabien
Capon, Robert J.
Title A search for kinase inhibitors and antibacterial agents: bromopyrrolo-2-aminoimidazoles from a deep-water Great Australian Bight sponge, Axinella sp.
Formatted title A search for kinase inhibitors and antibacterial agents: bromopyrrolo-2-aminoimidazoles from a deep-water Great Australian Bight sponge, Axinella sp.
Journal name Tetrahedron Letters  (ERA 2012 Listed)    (ERA 2010 Rank A)   Check publisher's open access policy
Publication date 2012-07
Sub-type Article
DOI 10.1016/j.tetlet.2012.05.051
Volume number 53
Issue number 29
ISSN 0040-4039; 1873-3581
Start page 3784
End page 3787
Total pages 4
Place of publication Oxford, United Kingdom
Publisher Pergamon
Collection year 2013
Language eng
Abstract Biological screening of a deep-water Great Australian Bight marine sponge, Axinella sp., detected inhibition against the neurodegenerative disease kinase targets CDK5/p25, CK1δ, and GSK3β, as well as significant levels of antibacterial activity. Chemical fractionation returned 18 secondary metabolites identified by detailed spectroscopic analysis as three new bromopyrrolo-2-aminoimidazoles, 14-O-sulfate massadine (1), 14-O-methyl massadine (2), and 3-O-methyl massadine chloride (3), together with the known metabolites massadine chloride (4), massadine (5), stylissadine B (6), axinellamines A–C (7–9), hymenin (10), stevensine (also known as odiline) (11), tauroacidin A (12), hymenidin (13), taurodispacamide A (14), oroidin (15), debromohymenialdisine (16), hymenialdisine (17), and aldisin (18). Armed with this focused natural product chemical diversity library, we re-established that 16 and 17 were nM kinase inhibitors, and determined that 3, 6, and 12–15 were sub μM antibacterials.
Keyword Axinella sp.
Bromopyrrolo-2-aminoimidazole
Neurodegenerative disease
Kinase inhibitor
Antibacterial
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article
Collections: Official 2013 Collection
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