Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.bmc.2008.10.077
Title: Psammaplin A as a general activator of cell-based signaling assays via HDAC inhibition and studies on some bromotyrosine derivatives
Authors: McCulloch, M.W.B.
Coombs, G.S. 
Banerjee, N.
Bugni, T.S.
Cannon, K.M.
Harper, M.K.
Veltri, C.A.
Virshup, D.M. 
Ireland, C.M.
Keywords: Bromotyrosine
Disulfide exchange
HDAC
LCMS
Luciferase
N-Methyl glutathione
Natural product library
Psammaplin
Reductive methylation
Sulfinate ester
Wnt signaling
Issue Date: 15-Mar-2009
Citation: McCulloch, M.W.B., Coombs, G.S., Banerjee, N., Bugni, T.S., Cannon, K.M., Harper, M.K., Veltri, C.A., Virshup, D.M., Ireland, C.M. (2009-03-15). Psammaplin A as a general activator of cell-based signaling assays via HDAC inhibition and studies on some bromotyrosine derivatives. Bioorganic and Medicinal Chemistry 17 (6) : 2189-2198. ScholarBank@NUS Repository. https://doi.org/10.1016/j.bmc.2008.10.077
Abstract: The Wnt signaling pathway regulates cell growth and development in metazoans, and is therefore of interest for drug discovery. By screening a library of 5808 pre-fractionated marine extracts in a cell-based Wnt signaling assay, several signaling activators and inhibitors were observed. LCMS-based fractionation rapidly identified an active compound from Pseudoceratina purpurea as psammaplin A, a known HDAC inhibitor. Other HDAC inhibitors similarly activated signaling in this assay, indicating HDAC inhibitors will be identified through many cell-based reporter assays. In a large scale analysis of P. purpurea, three previously undescribed bromotyrosine based natural products were identified; the structure of one of these was confirmed by synthesis. Additionally, three other derivatives of psammaplin A were prepared: a mixed disulfide and two sulfinate esters. Finally, evidence to support a structural reassignment of psammaplin I from a sulfone to the isomeric sulfinate ester is presented. © 2008.
Source Title: Bioorganic and Medicinal Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/130014
ISSN: 09680896
DOI: 10.1016/j.bmc.2008.10.077
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