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Bronchodilators are critical in managing asthma, a chronic respiratory condition characterized by airway constriction due to inflammation and hyper-reactivity. Specifically, bronchodilators ease this constriction by relaxing the bronchial muscles, facilitating easier breathing.
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Airway peroxidases catalyze nitration of the {beta}2-agonist salbutamol and decrease its pharmacological activity.

Krzysztof J Reszka1, Larry Sallans, Stephen Macha

  • 1Department of Internal Medicine, Veterans Affairs Medical Center, University of Cincinnati College of Medicine, Cincinnati, OH 45267-0557, USA. reszkakj@ucmail.uc.edu

The Journal of Pharmacology and Experimental Therapeutics
|October 27, 2010
PubMed
Summary

Severe asthma exacerbations may reduce the effectiveness of beta-2 agonists. This study shows that inflammation in asthma patients can lead to the nitration of salbutamol, a common beta-2 agonist, potentially decreasing its therapeutic efficacy.

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Published on: June 18, 2012

Area of Science:

  • Pharmacology
  • Biochemistry
  • Respiratory Medicine

Background:

  • Beta-2 agonists are primary bronchodilators for asthma relief.
  • Their efficacy can decrease during severe asthma exacerbations.
  • Increased peroxidase activity and nitrogen oxides in asthmatic airways are observed.

Purpose of the Study:

  • To investigate if salbutamol, a key beta-2 agonist, undergoes nitration in the inflamed asthmatic airway.
  • To determine the impact of nitration on salbutamol's pharmacological activity.

Main Methods:

  • Exposing salbutamol to various peroxidase enzymes (myeloperoxidase, eosinophil peroxidase, lactoperoxidase) with hydrogen peroxide and nitrite.
  • Utilizing absorption spectroscopy and mass spectrometry to identify and characterize nitrated metabolites.
  • Analyzing nitrated salbutamol's affinity for beta-2 adrenergic receptors and its effect on cAMP synthesis in airway smooth muscle cells.
  • Detecting metabolites in exhaled breath condensates from asthma patients.

Main Results:

  • Salbutamol was successfully nitrated in vitro, forming nitrosalbutamol (m/z 285.14) and a nitrophenol derivative (m/z 255.13).
  • The nitrophenol metabolite was detected in the breath of asthma patients but not in controls, indicating in vivo nitration.
  • Nitrated salbutamol exhibited reduced binding to beta-2 adrenergic receptors and impaired cAMP synthesis.
  • In vitro nitration was inhibited by ascorbate, thiocyanate, methimazole, and dapsone.

Conclusions:

  • Phenolic beta-2 agonists like salbutamol can be nitrated by peroxidases in the inflamed asthmatic airway.
  • This nitration process may reduce the therapeutic effectiveness of beta-2 agonists.
  • Understanding this mechanism could lead to strategies to maintain bronchodilator efficacy in severe asthma.