Diazotization reaction of nitric oxide trapped by hemoglobin

Sonoda, Masaru; Hashimoto, Taiju; Satomi, Akira; Miyazaki, Takashi; Ishida, Kiyoshi; Sakagishi, Yoshikatsu

doi:10.1016/0024-3205(94)90047-7

Cited by 13 publications

(3 citation statements)

References 14 publications

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“…To examine possible nitrite formation, CCl3NO2 (165 µg) in 330 µL of phosphate buffer (100 mM, pH 7.4) was added to equimolar GSH (340 µg) in the same phosphate buffer (170 µL). After reaction at 23 °C for 1, 2, and 4 h, nitrite was quantified by colorimetric assay at 548 nm 10 min after adding Griess reagent (2.5 mL) (23), comparing to a standard curve for reaction with NaNO2.…”

Section: Methodsmentioning

confidence: 99%

Chloropicrin: Reactions with Biological Thiols and Metabolism in Mice

Sparks

Quistad

Casida

1997

Chem. Res. Toxicol.

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Chloropicrin (CCl3NO2) is a preplant soil fumigant as a fungicide, warning agent for other fumigants, and former was gas. Its mode of action is unknown but presumably related to its facile metabolic dechlorination on reaction with biological thiols. These interactions were studied with 14CCl3NO2, 14CHCl2NO2, 14CH2ClNO2, and 14CH3NO2, synthesized for this purpose. Reaction of 14CCl3NO2 with GSH yields the di- and monochloro derivatives, GSSG, and a small amount of nitrite. The initial adduct with GSH is transient, but more stable derivatives are formed at longer times or on catalysis by GSH S-transferase. Human Hb, examined as a model thiol protein, reacts with 1.5 mol equiv of 14CCl3NO2 at pH 7.4 to produce 53-67% 14CHCl2NO2 and 10-11% Hb dducts (radiochemical yields) which, on longer incubation, release 14CHCl2NO2, CHCl2NO2 and CH2ClNO2 react with the same site(s) in Hb but more slowly. The dechlorination reactions are also catalyzed by liver cytosol and microsomes with NADPH. Dechlorination and adduct formation observed in vitro also occur in vivo in ip-treated mice. Thus, 14CCl3NO2 quickly gives 14CHCl2NO2, and some 14CO2 is formed, but the primary urinary metabolites are polar and nonvolatile. The major metabolite from 14CCl3NO2 in urine is less polar than those from 14CHCl2NO2, 14CH2ClNO2, and 14CH3NO2 which, in turn, are different from the 14CH2O and H14CO2Na metabolites. Liver tissue is adducted in vivo by 14CCl3NO2 (43% radiocarbon unextractable with methanol at 1 h), but the total radiocarbon content decreases 4-fold between 1 and 48 h after treatment. Liver effects from a high CCl3NO2 dose are associated with 19% less GSH and 50% more absorbance from soluble hemoproteins than controls. The toxicity of CCl3NO2 is probably due to disruption of multiple targets by its cascade of dechlorination products.

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Section: Methodsmentioning

confidence: 99%

Chloropicrin: Reactions with Biological Thiols and Metabolism in Mice

Sparks

Quistad

Casida

1997

Chem. Res. Toxicol.

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“…For discussion of this and related issues concerning NO measurement in biological models, see the review article by Archer [49]. In principle, the Griess assay can also be used to determine NO trapped by haemoglobin after separation of nitrosylhaemoglobin by gel filtration chromatography [50].…”

Section: Variants Of the Original Griess Reactionmentioning

confidence: 99%

“…Interfering proteins may "positively" contribute to nitrite due to intrinsic absorbance around 540 nm (e.g. by haemoglobin, myoglobin, NOS [50,179]). Protein-dependent interference may be "negative" due to reaction of nitrite with reactive moieties of proteins, notably tyrosine and cysteine, with nitrite nitrosating and nitrating proteins under the acidic conditions required for the Griess reaction [95,156].…”

Section: Sample Deproteination By Protein Precipitation Ultrafiltratmentioning

confidence: 99%

Analysis of nitrite and nitrate in biological fluids by assays based on the Griess reaction: Appraisal of the Griess reaction in the l-arginine/nitric oxide area of research

Tsikas

2007

Journal of Chromatography B

654

374

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Griess Diazotization

2010

Comprehensive Organic Name Reactions and Reagents

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The preparation of aromatic diazonium salts from primary aromatic amines, N 2 O 3 , and nitric acid is generally known as the Griess diazotization or Griess reaction. The most popular method of forming diazonium salt is to use nitrous acid generated in situ from sodium nitrite and an acid. This reaction is useful in the preparation of aromatic diazonium salts.

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Diazotization reaction of nitric oxide trapped by hemoglobin

Cited by 13 publications

References 14 publications

Chloropicrin: Reactions with Biological Thiols and Metabolism in Mice

Chloropicrin: Reactions with Biological Thiols and Metabolism in Mice

Analysis of nitrite and nitrate in biological fluids by assays based on the Griess reaction: Appraisal of the Griess reaction in the l-arginine/nitric oxide area of research

Griess Diazotization

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