Rapid decomposition of peroxynitrite by manganese porphyrin-antioxidant redox couples

Lee Jinbo; Julianne A. Hunt; John Taylor Groves

doi:10.1016/S0960-894X(97)10109-3

Rapid decomposition of peroxynitrite by manganese porphyrin-antioxidant redox couples

Lee Jinbo
, Julianne A. Hunt
, John Taylor Groves

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

61 Scopus citations

Abstract

Mn(III)TMPyP reacts rapidly with the toxic oxidant peroxynitrite (ONOO^- ) to generate an oxoMn(IV) species, but Mn(III)TMPyP is not catalytic for ONOO^- decomposition due to the slow reduction of oxoMn(IV) back to the Mn(III) oxidation state. However, when redox-coupled with biological antioxidants that efficiently reduce oxoMn(IV), Mn(III)TMPyP is transformed into an efficient 'peroxynitrite reductase'.

Original language	English (US)
Pages (from-to)	2913-2918
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	7
Issue number	22
DOIs	https://doi.org/10.1016/S0960-894X(97)10109-3
State	Published - Nov 18 1997

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/S0960-894X(97)10109-3

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title = "Rapid decomposition of peroxynitrite by manganese porphyrin-antioxidant redox couples",

abstract = "Mn(III)TMPyP reacts rapidly with the toxic oxidant peroxynitrite (ONOO- ) to generate an oxoMn(IV) species, but Mn(III)TMPyP is not catalytic for ONOO- decomposition due to the slow reduction of oxoMn(IV) back to the Mn(III) oxidation state. However, when redox-coupled with biological antioxidants that efficiently reduce oxoMn(IV), Mn(III)TMPyP is transformed into an efficient 'peroxynitrite reductase'.",

author = "Lee Jinbo and Hunt, \{Julianne A.\} and Groves, \{John Taylor\}",

note = "Funding Information: We have shown that a water-soluble manganese porphyrin, Mn(III)TMPyP, can become an efficient {"}peroxynitrite reductase{"} when redox-coupled with biological antioxidants, though the direct reactions of ONOO-with these antioxidants are slow. Cells exist in a reducing environment rich in antioxidants, including vitamin C (ascorbate),28,29 glutathione,30 and vitamin E (tocopherol);31,32 thus, the {"}peroxynitrite reductase{"} pathway of manganese porphyrins and similar compounds could play an important role in the protection of cells from oxidative stress in 02-' and ONOO-related diseases. 33 Acknowledgment. We acknowledge the excellent technical assistance of Steven C. Tizio. Support of this research by the National Institutes of Health (GM36928), the National Science Foundation for the purchase of 500 and 600 MHz NMR spectrometers, and Princeton University for the purchase of a stopped-flow spectrophotometer are gratefully acknowledged. JAH is the recipient of an NIH NRSA fellowship (GM18490).",

year = "1997",

month = nov,

day = "18",

doi = "10.1016/S0960-894X(97)10109-3",

language = "English (US)",

volume = "7",

pages = "2913--2918",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

number = "22",

}

TY - JOUR

T1 - Rapid decomposition of peroxynitrite by manganese porphyrin-antioxidant redox couples

AU - Jinbo, Lee

AU - Hunt, Julianne A.

AU - Groves, John Taylor

N1 - Funding Information: We have shown that a water-soluble manganese porphyrin, Mn(III)TMPyP, can become an efficient "peroxynitrite reductase" when redox-coupled with biological antioxidants, though the direct reactions of ONOO-with these antioxidants are slow. Cells exist in a reducing environment rich in antioxidants, including vitamin C (ascorbate),28,29 glutathione,30 and vitamin E (tocopherol);31,32 thus, the "peroxynitrite reductase" pathway of manganese porphyrins and similar compounds could play an important role in the protection of cells from oxidative stress in 02-' and ONOO-related diseases. 33 Acknowledgment. We acknowledge the excellent technical assistance of Steven C. Tizio. Support of this research by the National Institutes of Health (GM36928), the National Science Foundation for the purchase of 500 and 600 MHz NMR spectrometers, and Princeton University for the purchase of a stopped-flow spectrophotometer are gratefully acknowledged. JAH is the recipient of an NIH NRSA fellowship (GM18490).

PY - 1997/11/18

Y1 - 1997/11/18

N2 - Mn(III)TMPyP reacts rapidly with the toxic oxidant peroxynitrite (ONOO- ) to generate an oxoMn(IV) species, but Mn(III)TMPyP is not catalytic for ONOO- decomposition due to the slow reduction of oxoMn(IV) back to the Mn(III) oxidation state. However, when redox-coupled with biological antioxidants that efficiently reduce oxoMn(IV), Mn(III)TMPyP is transformed into an efficient 'peroxynitrite reductase'.

AB - Mn(III)TMPyP reacts rapidly with the toxic oxidant peroxynitrite (ONOO- ) to generate an oxoMn(IV) species, but Mn(III)TMPyP is not catalytic for ONOO- decomposition due to the slow reduction of oxoMn(IV) back to the Mn(III) oxidation state. However, when redox-coupled with biological antioxidants that efficiently reduce oxoMn(IV), Mn(III)TMPyP is transformed into an efficient 'peroxynitrite reductase'.

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UR - https://www.scopus.com/pages/publications/0343554032#tab=citedBy

U2 - 10.1016/S0960-894X(97)10109-3

DO - 10.1016/S0960-894X(97)10109-3

M3 - Article

AN - SCOPUS:0343554032

SN - 0960-894X

VL - 7

SP - 2913

EP - 2918

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 22

ER -

Rapid decomposition of peroxynitrite by manganese porphyrin-antioxidant redox couples

Abstract

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