Activation of NO donors in mitochondria:: Peroxidase metabolism of (2-hydroxyamino-vinyl)-triphenyl-phosphonium by cytochrome c releases NO and protects cells against apoptosis

被引：19

作者：

Stoyanovsky, Detcho A. ^{[1
]}

Vlasova, Irina I. ^{[2
,3
]}

Belikova, Natalia A. ^{[2
,3
]}

Kapralov, Alexandr ^{[2
,3
]}

Tyurin, Vladimir ^{[2
,3
]}

Kagan, Valerian E. ^{[2
,3
]}

机构：

[1] Univ Pittsburgh, Dept Surg, Pittsburgh, PA 15213 USA

[2] Univ Pittsburgh, Dept Environm & Occupat Hlth, Pittsburgh, PA 15213 USA

[3] Univ Pittsburgh, Ctr Free Radical & Antioxidant Hlth, Pittsburgh, PA 15213 USA

来源：

FEBS LETTERS | 2008年 / 582卷 / 05期

关键词：

nitric oxide; apoptosis; cytochrome c; cardiolipin; hydroxylamine; oxime; triphenylphosphonium;

D O I：

10.1016/j.febslet.2008.01.047

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

In mitochondrial apoptosis, the formation of cytochrome c-cardiolipin complex ([CL-cyt c]) with peroxidase properties is an early event in the cascade of reactions that leads to cell death. Herein, we report the synthesis of a new prodrug, (2-hydroxyamino-vinyl)-triphenyl-phosphonium (HVTP), which compartmentalizes exclusively into mitochondria, undergoes a [CL-cyt c]-catalyzed bioactivation to nitric oxide (NO), inhibits peroxidase activity, and protects cells from apoptosis. (c) 2008 Published by Elsevier B.V. on behalf of the Federation of European Biochemical Societies.

引用

页码：725 / 728

页数：4

共 11 条

[1] Fine-tuning the hydrophobicity of a mitochondria-targeted antioxidant
Asin-Cayuela, J
Manas, ARB
James, AM
Smith, RAJ
Murphy, MP
[J]. FEBS LETTERS, 2004, 571 (1-3): : 9 - 16
[2] MECHANISM OF RADICAL PRODUCTION FROM THE REACTION OF CYTOCHROME-C WITH ORGANIC HYDROPEROXIDES - AN ESR SPIN-TRAPPING INVESTIGATION
BARR, DP
MASON, RP
[J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1995, 270 (21) : 12709 - 12716
[3] Oxidation of the ketoxime acetoxime to nitric oxide by oxygen radical-generating systems
Caro, AA
Cederbaum, AL
Stoyanovsky, DA
[J]. NITRIC OXIDE-BIOLOGY AND CHEMISTRY, 2001, 5 (04): : 413 - 424
[4] Microsomal cytochrome P450 dependent oxidation of N-hydroxyguanidines, amidoximes, and ketoximes: Mechanism of the oxidative cleavage of their C=N(OH) bond with formation of nitrogen oxides
Jousserandot, A
Boucher, JL
Henry, Y
Niklaus, B
Clement, B
Mansuy, D
[J]. BIOCHEMISTRY, 1998, 37 (49) : 17179 - 17191
[5] Cytochrome c acts as a cardiolipin oxygenase required for release of proapoptotic factors
Kagan, VE
Tyurin, VA
Jiang, JF
Tyurina, YY
Ritov, VB
Amoscato, AA
Osipov, AN
Belikova, NA
Kapralov, AA
Kini, V
Vlasova, II
Zhao, Q
Zou, MM
Di, P
Svistunenko, DA
Kurnikov, IV
Borisenko, GG
[J]. NATURE CHEMICAL BIOLOGY, 2005, 1 (04) : 223 - 232
[6] NITRIC-OXIDE, AN INHIBITOR OF LIPID OXIDATION BY LIPOXYGENASE, CYCLOOXYGENASE AND HEMOGLOBIN
KANNER, J
HAREL, S
GRANIT, R
[J]. LIPIDS, 1992, 27 (01) : 46 - 49
[7] Detection and imaging of nitric oxide with novel fluorescent indicators: Diaminofluoresceins
Kojima, H
Nakatsubo, N
Kikuchi, K
Kawahara, S
Kirino, Y
Nagoshi, H
Hirata, Y
Nagano, T
[J]. ANALYTICAL CHEMISTRY, 1998, 70 (13) : 2446 - 2453
[8] Fluorescence determination of nitric oxide production in stimulated and activated platelets
Ku, Chia-Jui
Karunarathne, Welivitiya
Kenyon, Stacy
Root, Paul
Spence, Dana
[J]. ANALYTICAL CHEMISTRY, 2007, 79 (06) : 2421 - 2426
[9] Drug delivery to mitochondria: the key to mitochondrial medicine
Murphy, MP
Smith, RAJ
[J]. ADVANCED DRUG DELIVERY REVIEWS, 2000, 41 (02) : 235 - 250
[10] Nitric oxide inhibits peroxidase activity of cytochrome c• cardiolipin complex and blocks cardiolipin oxidation
Vlasova, Irina I.
Tyurin, Vladimir A.
Kapralov, Alexandr A.
Kurnikov, Igor V.
Osipov, Anatoly N.
Potapovich, Maxim V.
Stoyanovsky, Detcho A.
Kagan, Valerian E.
[J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2006, 281 (21) : 14554 - 14562

← 1 2 →