The oxidative and nitrosative chemistry of the nitric oxide/superoxide reaction in the presence of bicarbonate

David Jourd'heuil; Katrina M. Miranda; Sung M. Kim; Michael G. Espey; Yoram Vodovotz; Stephen Laroux; Christie T. Mai; Allen M. Miles; Matthew B. Grisham; David A. Wink

doi:10.1006/abbi.1999.1143

The oxidative and nitrosative chemistry of the nitric oxide/superoxide reaction in the presence of bicarbonate

David Jourd'heuil, Katrina M. Miranda, Sung M. Kim, Michael G. Espey, Yoram Vodovotz, Stephen Laroux, Christie T. Mai, Allen M. Miles, Matthew B. Grisham, David A. Wink^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

68 Scopus citations

Abstract

The primary product of the interaction between nitric oxide (NO) and superoxide (O₂/^-) is peroxynitrite (ONOO^-), which is capable of either oxidizing or nitrating various biological substrates. However, it has been shown that excess NO or O₂/^- can further react with ONOO^- to form species which mediate nitrosation. Subsequently, the controlled equilibrium between nitrosative and oxidative chemistry is critically dependent on the flux of NO and O₂/^-. Since ONOO^- reacts not only with NO and O₂/^- but also with CO₂, the effects of bicarbonate (HCO₃/^-) on the biphasic oxidation profile of dihydrorhodamine-123 (DHR) and on the nitrosation of both 2,3- diaminonaphthalene and reduced glutathione were examined. Nitric oxide and O₂/^- were formed with DEA/NO [NaEt₂NN(O)NO] and xanthine oxidase, respectively. The presence of HCO₃/^- did not alter either the oxidation profile of DHR with varying radical concentrations or the affinity of DHR for the oxidative species. This suggests that the presence of CO₂ does not affect the scavenging of ONOO^by either NO or O₂/^-. However, an increase in the rate of DHR oxidation by ONOO^- in the presence of HCO₃/^- suggests that a CO₂-ONOO^- adduct does play a role in the interaction of NO or O₂/^- with a product derived from ONOO^-. Further examination of the chemistry revealed that the intermediate that reacts with NO is neither ONOO^- nor cis-HOONO. It was concluded that NO reacts with both trans-HOONO and a CO₂ adduct of ONOO^- to form nitrosating species which have similar oxidation chemistry and reactivity with O₂/^- and NO.

Original language	English
Pages (from-to)	92-100
Number of pages	9
Journal	Archives of Biochemistry and Biophysics
Volume	365
Issue number	1
DOIs	https://doi.org/10.1006/abbi.1999.1143
State	Published - 1 May 1999
Externally published	Yes

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@article{73869e4922f0425ebf7277b7268c0e73,

title = "The oxidative and nitrosative chemistry of the nitric oxide/superoxide reaction in the presence of bicarbonate",

abstract = "The primary product of the interaction between nitric oxide (NO) and superoxide (O2/-) is peroxynitrite (ONOO-), which is capable of either oxidizing or nitrating various biological substrates. However, it has been shown that excess NO or O2/- can further react with ONOO- to form species which mediate nitrosation. Subsequently, the controlled equilibrium between nitrosative and oxidative chemistry is critically dependent on the flux of NO and O2/-. Since ONOO- reacts not only with NO and O2/- but also with CO2, the effects of bicarbonate (HCO3/-) on the biphasic oxidation profile of dihydrorhodamine-123 (DHR) and on the nitrosation of both 2,3- diaminonaphthalene and reduced glutathione were examined. Nitric oxide and O2/- were formed with DEA/NO [NaEt2NN(O)NO] and xanthine oxidase, respectively. The presence of HCO3/- did not alter either the oxidation profile of DHR with varying radical concentrations or the affinity of DHR for the oxidative species. This suggests that the presence of CO2 does not affect the scavenging of ONOOby either NO or O2/-. However, an increase in the rate of DHR oxidation by ONOO- in the presence of HCO3/- suggests that a CO2-ONOO- adduct does play a role in the interaction of NO or O2/- with a product derived from ONOO-. Further examination of the chemistry revealed that the intermediate that reacts with NO is neither ONOO- nor cis-HOONO. It was concluded that NO reacts with both trans-HOONO and a CO2 adduct of ONOO- to form nitrosating species which have similar oxidation chemistry and reactivity with O2/- and NO.",

author = "David Jourd'heuil and Miranda, {Katrina M.} and Kim, {Sung M.} and Espey, {Michael G.} and Yoram Vodovotz and Stephen Laroux and Mai, {Christie T.} and Miles, {Allen M.} and Grisham, {Matthew B.} and Wink, {David A.}",

note = "Funding Information: 1This work was supported in part by NIH Grant DK 43785. 2 To whom correspondence should be addressed at Radiation Biology Branch, National Cancer Institute, Bldg. 10, Room B3-B69, Bethesda, MD 20892. Fax: (301) 480-2238.",

year = "1999",

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doi = "10.1006/abbi.1999.1143",

language = "English",

volume = "365",

pages = "92--100",

journal = "Archives of Biochemistry and Biophysics",

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T1 - The oxidative and nitrosative chemistry of the nitric oxide/superoxide reaction in the presence of bicarbonate

AU - Jourd'heuil, David

AU - Miranda, Katrina M.

AU - Kim, Sung M.

AU - Espey, Michael G.

AU - Vodovotz, Yoram

AU - Laroux, Stephen

AU - Mai, Christie T.

AU - Miles, Allen M.

AU - Grisham, Matthew B.

AU - Wink, David A.

N1 - Funding Information: 1This work was supported in part by NIH Grant DK 43785. 2 To whom correspondence should be addressed at Radiation Biology Branch, National Cancer Institute, Bldg. 10, Room B3-B69, Bethesda, MD 20892. Fax: (301) 480-2238.

PY - 1999/5/1

Y1 - 1999/5/1

N2 - The primary product of the interaction between nitric oxide (NO) and superoxide (O2/-) is peroxynitrite (ONOO-), which is capable of either oxidizing or nitrating various biological substrates. However, it has been shown that excess NO or O2/- can further react with ONOO- to form species which mediate nitrosation. Subsequently, the controlled equilibrium between nitrosative and oxidative chemistry is critically dependent on the flux of NO and O2/-. Since ONOO- reacts not only with NO and O2/- but also with CO2, the effects of bicarbonate (HCO3/-) on the biphasic oxidation profile of dihydrorhodamine-123 (DHR) and on the nitrosation of both 2,3- diaminonaphthalene and reduced glutathione were examined. Nitric oxide and O2/- were formed with DEA/NO [NaEt2NN(O)NO] and xanthine oxidase, respectively. The presence of HCO3/- did not alter either the oxidation profile of DHR with varying radical concentrations or the affinity of DHR for the oxidative species. This suggests that the presence of CO2 does not affect the scavenging of ONOOby either NO or O2/-. However, an increase in the rate of DHR oxidation by ONOO- in the presence of HCO3/- suggests that a CO2-ONOO- adduct does play a role in the interaction of NO or O2/- with a product derived from ONOO-. Further examination of the chemistry revealed that the intermediate that reacts with NO is neither ONOO- nor cis-HOONO. It was concluded that NO reacts with both trans-HOONO and a CO2 adduct of ONOO- to form nitrosating species which have similar oxidation chemistry and reactivity with O2/- and NO.

AB - The primary product of the interaction between nitric oxide (NO) and superoxide (O2/-) is peroxynitrite (ONOO-), which is capable of either oxidizing or nitrating various biological substrates. However, it has been shown that excess NO or O2/- can further react with ONOO- to form species which mediate nitrosation. Subsequently, the controlled equilibrium between nitrosative and oxidative chemistry is critically dependent on the flux of NO and O2/-. Since ONOO- reacts not only with NO and O2/- but also with CO2, the effects of bicarbonate (HCO3/-) on the biphasic oxidation profile of dihydrorhodamine-123 (DHR) and on the nitrosation of both 2,3- diaminonaphthalene and reduced glutathione were examined. Nitric oxide and O2/- were formed with DEA/NO [NaEt2NN(O)NO] and xanthine oxidase, respectively. The presence of HCO3/- did not alter either the oxidation profile of DHR with varying radical concentrations or the affinity of DHR for the oxidative species. This suggests that the presence of CO2 does not affect the scavenging of ONOOby either NO or O2/-. However, an increase in the rate of DHR oxidation by ONOO- in the presence of HCO3/- suggests that a CO2-ONOO- adduct does play a role in the interaction of NO or O2/- with a product derived from ONOO-. Further examination of the chemistry revealed that the intermediate that reacts with NO is neither ONOO- nor cis-HOONO. It was concluded that NO reacts with both trans-HOONO and a CO2 adduct of ONOO- to form nitrosating species which have similar oxidation chemistry and reactivity with O2/- and NO.

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The oxidative and nitrosative chemistry of the nitric oxide/superoxide reaction in the presence of bicarbonate

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