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https://hdl.handle.net/2440/43432
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Type: | Journal article |
Title: | Michael addition of acrolein to lysinyl and N-terminal residues of a model peptide: targets for cytoprotective hydrazino drugs |
Author: | Kaminskas, L. Pyke, S. Burcham, P. |
Citation: | Rapid Communications in Mass Spectrometry, 2007; 21(7):1155-1164 |
Publisher: | John Wiley & Sons Ltd |
Issue Date: | 2007 |
ISSN: | 0951-4198 1097-0231 |
Statement of Responsibility: | Lisa M. Kaminskas, Simon M. Pyke, Philip C. Burcham |
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. |
Keywords: | Acrolein Hydrazines Lysine Peptides Drug Delivery Systems Spectrometry, Mass, Electrospray Ionization Protein Interaction Mapping Binding Sites Protein Binding Cytoprotection |
Description: | The definitive version may be found at www.wiley.com |
DOI: | 10.1002/rcm.2945 |
Published version: | http://dx.doi.org/10.1002/rcm.2945 |
Appears in Collections: | Aurora harvest Chemistry publications |
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