API

Event: 1584

Key Event Title

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Interaction of α-diketones with arginine residues

Short name

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Interaction of α-diketones with arginine residues

Biological Context

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Level of Biological Organization
Molecular

Cell term

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Organ term

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Key Event Components

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Process Object Action

Key Event Overview


AOPs Including This Key Event

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AOP Name Role of event in AOP
α-diketone-induced bronchiolitis obliterans MolecularInitiatingEvent

Stressors

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Taxonomic Applicability

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Life Stages

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Sex Applicability

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Key Event Description

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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

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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

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Evidence for Perturbation by Stressor


Overview for Molecular Initiating Event

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References

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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