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Rapid CommunicationShort Communication

Acrolein, an α,β-Unsaturated Aldehyde, Irreversibly Inhibits the Acetylation of Aromatic Amine Xenobiotics by Human Arylamine N-Acetyltransferase 1

Linh C. Bui, Amine Manaa, Ximing Xu, Romain Duval, Florent Busi, Jean-Marie Dupret, Fernando Rodrigues-Lima and Julien Dairou
Drug Metabolism and Disposition July 2013, 41 (7) 1300-1305; DOI: https://doi.org/10.1124/dmd.113.052258
Linh C. Bui
Unité de Biologie Fonctionnelle et Adaptative, Université Paris Diderot, Sorbonne Paris Cité, CNRS EAC 4413, Paris, France
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Amine Manaa
Unité de Biologie Fonctionnelle et Adaptative, Université Paris Diderot, Sorbonne Paris Cité, CNRS EAC 4413, Paris, France
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Ximing Xu
Unité de Biologie Fonctionnelle et Adaptative, Université Paris Diderot, Sorbonne Paris Cité, CNRS EAC 4413, Paris, France
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Romain Duval
Unité de Biologie Fonctionnelle et Adaptative, Université Paris Diderot, Sorbonne Paris Cité, CNRS EAC 4413, Paris, France
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Florent Busi
Unité de Biologie Fonctionnelle et Adaptative, Université Paris Diderot, Sorbonne Paris Cité, CNRS EAC 4413, Paris, France
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Jean-Marie Dupret
Unité de Biologie Fonctionnelle et Adaptative, Université Paris Diderot, Sorbonne Paris Cité, CNRS EAC 4413, Paris, France
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Fernando Rodrigues-Lima
Unité de Biologie Fonctionnelle et Adaptative, Université Paris Diderot, Sorbonne Paris Cité, CNRS EAC 4413, Paris, France
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Julien Dairou
Unité de Biologie Fonctionnelle et Adaptative, Université Paris Diderot, Sorbonne Paris Cité, CNRS EAC 4413, Paris, France
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Abstract

Acrolein is an electrophilic α,β-unsaturated aldehyde of industrial, pharmaceutic, and toxicologic importance to which we are exposed in environmental, occupational, and therapeutic situations. Acrolein is known to exert different biologic effects through reactions with cellular macromolecules such as DNA, certain proteins, or glutathione. In many situations (such as in tobacco smoke or other fumes), exposure to acrolein occurs concomitantly with other compounds such as aromatic amine chemicals. Interestingly, it has been shown that acrolein could impact the cellular metabolism of aromatic xenobiotics through an indirect mechanism based on the transcriptional induction of phase II xenobiotic-metabolizing enzymes. Here we report a novel mechanism by which acrolein acts on the metabolism of aromatic foreign chemicals. We provide molecular, kinetic, and cellular evidence that acrolein can react directly and irreversibly with arylamine N-acetyltransferases, a major family of xenobiotic-metabolizing enzymes involved in the metabolization of aromatic amine chemicals. Formation of an acrolein adduct with a catalytic cysteine residue in the active site is responsible for the impairment of aromatic amine acetylation by the enzyme. This biochemical process may represent an additional mechanism by which acrolein impacts the metabolism and fate of aromatic amine drugs and pollutants.

Footnotes

    • Received April 2, 2013.
    • Accepted April 29, 2013.
  • F.R.L. and J.D. share senior authorship.

  • This work was supported by grants from Université Paris Diderot; CNRS; “la Caisse d’Assurance Maladie des Professions Liberales de Province;” and Chancellerie des Universités-Legs Poix. A.M., X.X. and R.D. are supported by PhD fellowships from the Algerian government, the China Scholar Council, and the Region Ile-de-France, respectively.

  • dx.doi.org/10.1124/dmd.113.052258.

  • Copyright © 2013 by The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 41 (7)
Drug Metabolism and Disposition
Vol. 41, Issue 7
1 Jul 2013
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Rapid CommunicationShort Communication

Inhibition of NAT1-Dependent Acetylation Pathway by Acrolein

Linh C. Bui, Amine Manaa, Ximing Xu, Romain Duval, Florent Busi, Jean-Marie Dupret, Fernando Rodrigues-Lima and Julien Dairou
Drug Metabolism and Disposition July 1, 2013, 41 (7) 1300-1305; DOI: https://doi.org/10.1124/dmd.113.052258

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Rapid CommunicationShort Communication

Inhibition of NAT1-Dependent Acetylation Pathway by Acrolein

Linh C. Bui, Amine Manaa, Ximing Xu, Romain Duval, Florent Busi, Jean-Marie Dupret, Fernando Rodrigues-Lima and Julien Dairou
Drug Metabolism and Disposition July 1, 2013, 41 (7) 1300-1305; DOI: https://doi.org/10.1124/dmd.113.052258
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