Literature DB >> 18258194

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

Detcho A Stoyanovsky1, Irina I Vlasova, Natalia A Belikova, Alexandr Kapralov, Vladimir Tyurin, Joel S Greenberger, Valerian E Kagan.   

Abstract

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.

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Year:  2008        PMID： 18258194      PMCID： PMC2275320          DOI： 10.1016/j.febslet.2008.01.047

Source DB:  PubMed          Journal:  FEBS Lett        ISSN： 0014-5793            Impact factor:   4.124


  10 in total

1.  Nitric oxide inhibits peroxidase activity of cytochrome c.cardiolipin complex and blocks cardiolipin oxidation.

Authors:  Irina I Vlasova; Vladimir A Tyurin; Alexandr A Kapralov; Igor V Kurnikov; Anatoly N Osipov; Maxim V Potapovich; Detcho A Stoyanovsky; Valerian E Kagan
Journal:  J Biol Chem       Date:  2006-03-16       Impact factor: 5.157

2.  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.

Authors:  A Jousserandot; J L Boucher; Y Henry; B Niklaus; B Clement; D Mansuy
Journal:  Biochemistry       Date:  1998-12-08       Impact factor: 3.162

3.  Oxidation of the ketoxime acetoxime to nitric oxide by oxygen radical-generating systems.

Authors:  A A Caro; A I Cederbaum; D A Stoyanovsky
Journal:  Nitric Oxide       Date:  2001-08       Impact factor: 4.427

4.  Cytochrome c acts as a cardiolipin oxygenase required for release of proapoptotic factors.

Authors:  Valerian E Kagan; Vladimir A Tyurin; Jianfei Jiang; Yulia Y Tyurina; Vladimir B Ritov; Andrew A Amoscato; Anatoly N Osipov; Natalia A Belikova; Alexandr A Kapralov; Vidisha Kini; Irina I Vlasova; Qing Zhao; Meimei Zou; Peter Di; Dimitry A Svistunenko; Igor V Kurnikov; Gregory G Borisenko
Journal:  Nat Chem Biol       Date:  2005-08-14       Impact factor: 15.040

Review 5.  Drug delivery to mitochondria: the key to mitochondrial medicine.

Authors:  M P Murphy; R A Smith
Journal:  Adv Drug Deliv Rev       Date:  2000-03-30       Impact factor: 15.470

6.  Nitric oxide, an inhibitor of lipid oxidation by lipoxygenase, cyclooxygenase and hemoglobin.

Authors:  J Kanner; S Harel; R Granit
Journal:  Lipids       Date:  1992-01       Impact factor: 1.880

7.  Mechanism of radical production from the reaction of cytochrome c with organic hydroperoxides. An ESR spin trapping investigation.

Authors:  D P Barr; R P Mason
Journal:  J Biol Chem       Date:  1995-05-26       Impact factor: 5.157

8.  Fluorescence determination of nitric oxide production in stimulated and activated platelets.

Authors:  Chia-Jui Ku; Welivitiya Karunarathne; Stacy Kenyon; Paul Root; Dana Spence
Journal:  Anal Chem       Date:  2007-02-09       Impact factor: 6.986

9.  Detection and imaging of nitric oxide with novel fluorescent indicators: diaminofluoresceins.

Authors:  H Kojima; N Nakatsubo; K Kikuchi; S Kawahara; Y Kirino; H Nagoshi; Y Hirata; T Nagano
Journal:  Anal Chem       Date:  1998-07-01       Impact factor: 6.986

10.  Fine-tuning the hydrophobicity of a mitochondria-targeted antioxidant.

Authors:  Jordi Asin-Cayuela; Abdul-Rahman B Manas; Andrew M James; Robin A J Smith; Michael P Murphy
Journal:  FEBS Lett       Date:  2004-07-30       Impact factor: 4.124
  10 in total
  14 in total

Review 1.  Mitochondria as a target in treatment.

Authors:  Marie-Céline Frantz; Peter Wipf
Journal:  Environ Mol Mutagen       Date:  2010-06       Impact factor: 3.216

2.  Molecular design of new inhibitors of peroxidase activity of cytochrome c/cardiolipin complexes: fluorescent oxadiazole-derivatized cardiolipin.

Authors:  G G Borisenko; A A Kapralov; V A Tyurin; A Maeda; D A Stoyanovsky; V E Kagan
Journal:  Biochemistry       Date:  2008-12-23       Impact factor: 3.162

Review 3.  Targeted nanoparticles in mitochondrial medicine.

Authors:  Rakesh K Pathak; Nagesh Kolishetti; Shanta Dhar
Journal:  Wiley Interdiscip Rev Nanomed Nanobiotechnol       Date:  2014-10-27

Review 4.  Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications.

Authors:  Jacek Zielonka; Joy Joseph; Adam Sikora; Micael Hardy; Olivier Ouari; Jeannette Vasquez-Vivar; Gang Cheng; Marcos Lopez; Balaraman Kalyanaraman
Journal:  Chem Rev       Date:  2017-06-27       Impact factor: 60.622

Review 5.  Mitochondria as a drug target in ischemic heart disease and cardiomyopathy.

Authors:  Andrew M Walters; George A Porter; Paul S Brookes
Journal:  Circ Res       Date:  2012-10-12       Impact factor: 17.367

Review 6.  Cytochrome c/cardiolipin relations in mitochondria: a kiss of death.

Authors:  Valerian E Kagan; Hülya A Bayir; Natalia A Belikova; Olexandr Kapralov; Yulia Y Tyurina; Vladimir A Tyurin; Jianfei Jiang; Detcho A Stoyanovsky; Peter Wipf; Patrick M Kochanek; Joel S Greenberger; Bruce Pitt; Anna A Shvedova; Grigory Borisenko
Journal:  Free Radic Biol Med       Date:  2009-03-12       Impact factor: 7.376

Review 7.  Mitochondrial targeting of electron scavenging antioxidants: Regulation of selective oxidation vs random chain reactions.

Authors:  Valerian E Kagan; Peter Wipf; Detcho Stoyanovsky; Joel S Greenberger; Grigory Borisenko; Natalia A Belikova; Naveena Yanamala; Alejandro K Samhan Arias; Muhammad A Tungekar; Jianfei Jiang; Yulia Y Tyurina; Jing Ji; Judith Klein-Seetharaman; Bruce R Pitt; Anna A Shvedova; Hülya Bayir
Journal:  Adv Drug Deliv Rev       Date:  2009-08-27       Impact factor: 15.470

8.  Mitochondria-targeted (2-hydroxyamino-vinyl)-triphenyl-phosphonium releases NO(.) and protects mouse embryonic cells against irradiation-induced apoptosis.

Authors:  Natalia A Belikova; Jianfei Jiang; Detcho A Stoyanovsky; Ashley Glumac; Hülya Bayir; Joel S Greenberger; Valerian E Kagan
Journal:  FEBS Lett       Date:  2009-05-08       Impact factor: 4.124

9.  Signaling events in apoptotic photokilling of 5-aminolevulinic acid-treated tumor cells: inhibitory effects of nitric oxide.

Authors:  Reshma Bhowmick; Albert W Girotti
Journal:  Free Radic Biol Med       Date:  2009-06-11       Impact factor: 7.376

10.  Inhibition of glycogen synthase kinase-3β prevents NSAID-induced acute kidney injury.

Authors:  Hao Bao; Yan Ge; Shougang Zhuang; Lance D Dworkin; Zhihong Liu; Rujun Gong
Journal:  Kidney Int       Date:  2012-01-18       Impact factor: 10.612
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