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Allylic nitro compounds as nitrite donors.

Harinath Chakrapani1, Michael J Gorczynski, S Bruce King

  • 1Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109, USA.

Journal of the American Chemical Society
|December 15, 2006
PubMed
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Researchers developed organic compounds that release nitrite and nitric oxide. A specific compound, 2-(nitromethyl)-cyclohex-1-ene-3-one, efficiently releases nitrite and can form nitric oxide, offering tunable control.

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Biochemistry

Background:

  • Allylic nitro compounds are explored as potential sources of nitrite and nitric oxide.
  • Spontaneous or nucleophile-promoted nitrite release from unactivated allylic nitro compounds is generally slow.

Purpose of the Study:

  • To synthesize and evaluate allylic nitro compounds as organic sources of nitrite and nitric oxide.
  • To investigate the factors influencing the rate of nitrite and nitric oxide release.

Main Methods:

  • Synthesis of allylic nitro compounds.
  • Kinetic studies of nitrite release in buffer (pH 7.4).
  • Evaluation of compound reactions with L-cysteine, hemoglobin, and ascorbic acid.

Main Results:

Related Experiment Videos

  • 2-(nitromethyl)-cyclohex-1-ene-3-one spontaneously dissociates to release nitrite (kobs = 1.6 x 10(-5) s(-1)).
  • This compound rapidly yields nitrite in the presence of L-cysteine, mimicking sodium nitrite's reaction with hemoglobin.
  • Nitric oxide formation was observed with L-cysteine and ascorbic acid.
  • Structural modifications and nucleophile characteristics modulate nitrite release rates.

Conclusions:

  • A novel structural framework for tunable nitrite and nitric oxide liberation from organic molecules has been discovered.
  • These findings open avenues for developing new therapeutic agents or research tools based on controlled NO/nitrite delivery.