Please use this identifier to cite or link to this item: https://hdl.handle.net/2440/43432
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dc.contributor.authorKaminskas, L.-
dc.contributor.authorPyke, S.-
dc.contributor.authorBurcham, P.-
dc.date.issued2007-
dc.identifier.citationRapid Communications in Mass Spectrometry, 2007; 21(7):1155-1164-
dc.identifier.issn0951-4198-
dc.identifier.issn1097-0231-
dc.identifier.urihttp://hdl.handle.net/2440/43432-
dc.descriptionThe definitive version may be found at www.wiley.com-
dc.description.abstractThe antihypertensive drug hydralazine blocks acrolein-mediated toxicity by trapping both free aldehyde- and acrolein-adducted proteins, with the latter property more closely related to cytoprotection in cellular models. Here we report the identification of products from 'protein adduct-trapping' reactions using electrospray ionisation mass spectrometry (ESI-MS). Reaction of a 13-residue peptide containing a single lysine with acrolein for 30 min generated ions corresponding to mono- and bis-Michael-adducted peptides. An ion corresponding to a cyclic species formed from bis-adducted lysine was conspicuous at later times (60, 180 min). Tandem mass spectrometric (MS/MS) analysis revealed Michael adduction also occurred on the N-terminus, with a novel N-terminal (3-formyl-3,4-dehydropiperidino) species formed on this residue. Addition of hydralazine to acrolein-adducted peptides generated a diverse range of hydrazones that were also characterised by MS/MS analysis. The results confirm that mass spectrometry is a powerful tool for characterising the reactions of noxious electrophiles with biological macromolecules.-
dc.description.statementofresponsibilityLisa M. Kaminskas, Simon M. Pyke, Philip C. Burcham-
dc.language.isoen-
dc.publisherJohn Wiley & Sons Ltd-
dc.source.urihttp://dx.doi.org/10.1002/rcm.2945-
dc.subjectAcrolein-
dc.subjectHydrazines-
dc.subjectLysine-
dc.subjectPeptides-
dc.subjectDrug Delivery Systems-
dc.subjectSpectrometry, Mass, Electrospray Ionization-
dc.subjectProtein Interaction Mapping-
dc.subjectBinding Sites-
dc.subjectProtein Binding-
dc.subjectCytoprotection-
dc.titleMichael addition of acrolein to lysinyl and N-terminal residues of a model peptide: targets for cytoprotective hydrazino drugs-
dc.typeJournal article-
dc.identifier.doi10.1002/rcm.2945-
pubs.publication-statusPublished-
dc.identifier.orcidPyke, S. [0000-0002-0061-5115]-
Appears in Collections:Aurora harvest
Chemistry publications

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