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Event: 1584
Key Event Title
Interaction of α-diketones with arginine residues
Short name
Biological Context
Cell term
Organ term
Key Event Components
Process | Object | Action |
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Key Event Overview
AOPs Including This Key Event
AOP Name | Role of event in AOP | Point of Contact | Author Status | OECD Status |
---|---|---|---|---|
α-diketone-induced bronchiolitis obliterans | MolecularInitiatingEvent | Marvin Martens (send email) | Under development: Not open for comment. Do not cite |
Stressors
Taxonomic Applicability
Life Stages
Sex Applicability
Key Event Description
The electrophilic α-diketones interact with proteins via direct covalent binding to cellular nucleophiles. The interaction occurs predominantly with the arginine residues of proteins.
How It Is Measured or Detected
The binding of α-diketones with proteins can be measured by LC-MS and 1H- and 13C NMR analysis (Anders 2017, Mathews et al. 2010, Saraiva et al. 2016)
Domain of Applicability
Evidence for Perturbation by Stressor
Overview for Molecular Initiating Event
References
Anders, M. W. (2017). Diacetyl and related flavorant α-Diketones: Biotransformation, cellular interactions, and respiratory-tract toxicity. Toxicology, 388, 21–29. https://doi.org/10.1016/j.tox.2017.02.002
Mathews, J. M., Watson, S. L., Snyder, R. W., Burgess, J. P., & Morgan, D. L. (2010). Reaction of the butter flavorant diacetyl (2,3-Butanedione) with N-??-acetylarginine: A model for epitope formation with pulmonary proteins in the etiology of obliterative bronchiolitis. Journal of Agricultural and Food Chemistry, 58(24), 12761–12768. https://doi.org/10.1021/jf103251w
More, S. S., Raza, A., & Vince, R. (2012). The butter flavorant, diacetyl, forms a covalent adduct with 2-deoxyguanosine, uncoils DNA, and leads to cell death. Journal of Agricultural and Food Chemistry, 60(12), 3311–3317. https://doi.org/10.1021/jf300180e
Saraiva, M. A., Borges, C. M., & Helena Flor??ncio, M. (2016). Mass spectrometric studies of the reaction of a blocked arginine with diketonic ??-dicarbonyls. Amino Acids, 48(3), 873–885. https://doi.org/10.1007/s00726-015-2135-6