Reaction of tetrahydrobiopterin with superoxide: EPR-kinetic analysis and characterization of the pteridine radical

Vásquez-Vivar, Jeannette; Whitsett, Jennifer; Martásek, Pavel; Hogg, Neil; Kalyanaraman, B.

doi:10.1016/s0891-5849(01)00680-3

Cited by 112Free Radicals and AntioxidantsNitric Oxide and Endothelin EffectsElectron Spin Resonance Studies

Reaction of tetrahydrobiopterin with superoxide: EPR-kinetic analysis and characterization of the pteridine radical

Vásquez-Vivar, Jeannette, Whitsett, Jennifer, Martásek, Pavel, Hogg, Neil, Kalyanaraman, B.·2001·Free Radical Biology and Medicine

DOI 10.1016/s0891-5849(01)00680-3

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Abstract

It has been shown that BH(4) ameliorates endothelial dysfunction associated with conditions such as hypertension, cigarette smoking, and diabetes. This effect has been proposed to be due to a superoxide scavenging activity of BH(4). To examine this possibility we determined the rate constant for the reaction between BH(4) and superoxide using electron paramagnetic resonance (EPR) spin trapping competition experiments with 5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide (DEPMPO). We calculated a rate constant for the reaction between BH(4) and superoxide of 3.9 +/- 0.2 x 10(5) M(-1)s(-1) at pH 7.4 and room temperature. This result suggests that superoxide scavenging by BH(4) is not a major reaction in vivo. HPLC product analysis showed that 7,8-BH(2) and pterin are the stable products generated from the reaction. The formation of BH(4) cation radical (BH(4)(*+)) was demonstrated by direct EPR only under acidic conditions. Isotopic substitution experiments demonstrated that the BH(4)(*+) is mainly delocalized on the pyrazine ring of BH(4). In parallel experiments, we investigated the effect of ascorbate on 7,8-BH(2) reduction and eNOS activity. We demonstrated that ascorbate does not reduce 7,8-BH(2) to BH(4), nor does it stimulate nitric oxide release from eNOS incubated with 7,8-BH(2). In conclusion, it is likely that BH(4)-dependent inhibition of superoxide formation from eNOS is the mechanism that better explains the antioxidant effects of BH(4) in the vasculature.

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Ascorbate cannot recover BH4 from BH2.
“However, ascorbate cannot recover BH4 from BH2 [162].”
From Vitamin C-Sources, Physiological Role, Kinetics, Deficiency, Use, Toxicity, and Determination (2021) · cites this paper as [162]

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Authors: Vásquez-Vivar, J., Whitsett, J., Martásek, P., Hogg, N., & Kalyanaraman, B.
Affiliations: Medical College of Wisconsin (US)
ORCID: Hogg, Neil
Kalyanaraman, B.
Venue: Free Radical Biology and Medicine
Publisher: Elsevier BV
Published: 2001-10
Volume: 31
Issue: 8
Pages: 975-985
ISSN: 0891-5849 (ISSN-L)
DOI: 10.1016/s0891-5849(01)00680-3
OpenAlex: W2051459142
Cited by: 112
References: 51
Citations by year: 2024: 1 · 2022: 6 · 2021: 4 · 2020: 4 · 2019: 1 · 2018: 2 · 2017: 1 · 2016: 1 · 2015: 3 · 2014: 2 · 2013: 7 · 2012: 5
FWCI: 8.33
Type: journal article
Language: en
Open access: closed
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
Locations: Free Radical Biology and Medicine (publishedVersion)
PubMed (publishedVersion)
Funders: American Heart Association
National Institutes of Health
National Institute of General Medical Sciences (R01GM052419, GM-52419)
Topics: Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
Health Sciences › Medicine › Physiology › Nitric Oxide and Endothelin Effects
Life Sciences › Biochemistry, Genetics and Molecular Biology › Biophysics › Electron Spin Resonance Studies
Keywords: tetrahydrobiopterin, superoxide, superoxide radical scavenging, endothelial nitric oxide synthase, vitamin C, nitric oxide release, antioxidant defense, endothelial dysfunction, rate constants
MeSH terms: Ascorbic Acid, Biopterins, Electron Spin Resonance Spectroscopy, Free Radicals, Kinetics, Oxidation-Reduction, Pterins, Superoxides, Free Radical Scavengers, Nitric Oxide Synthase, Nitric Oxide Synthase Type III

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Reaction of tetrahydrobiopterin with superoxide: EPR-kinetic analysis and characterization of the pteridine radical

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