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https://hdl.handle.net/2440/43432
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dc.contributor.author | Kaminskas, L. | - |
dc.contributor.author | Pyke, S. | - |
dc.contributor.author | Burcham, P. | - |
dc.date.issued | 2007 | - |
dc.identifier.citation | Rapid Communications in Mass Spectrometry, 2007; 21(7):1155-1164 | - |
dc.identifier.issn | 0951-4198 | - |
dc.identifier.issn | 1097-0231 | - |
dc.identifier.uri | http://hdl.handle.net/2440/43432 | - |
dc.description | The definitive version may be found at www.wiley.com | - |
dc.description.abstract | The 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.statementofresponsibility | Lisa M. Kaminskas, Simon M. Pyke, Philip C. Burcham | - |
dc.language.iso | en | - |
dc.publisher | John Wiley & Sons Ltd | - |
dc.source.uri | http://dx.doi.org/10.1002/rcm.2945 | - |
dc.subject | Acrolein | - |
dc.subject | Hydrazines | - |
dc.subject | Lysine | - |
dc.subject | Peptides | - |
dc.subject | Drug Delivery Systems | - |
dc.subject | Spectrometry, Mass, Electrospray Ionization | - |
dc.subject | Protein Interaction Mapping | - |
dc.subject | Binding Sites | - |
dc.subject | Protein Binding | - |
dc.subject | Cytoprotection | - |
dc.title | Michael addition of acrolein to lysinyl and N-terminal residues of a model peptide: targets for cytoprotective hydrazino drugs | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1002/rcm.2945 | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Pyke, S. [0000-0002-0061-5115] | - |
Appears in Collections: | Aurora harvest Chemistry publications |
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