Literature DB >> 15796534

Discrimination of nitroxyl and nitric oxide by water-soluble Mn(III) porphyrins.

Marcelo A Martí1, Sara E Bari, Darío A Estrin, Fabio Doctorovich.   

Abstract

The water-soluble manganese(III) meso-tetrakis (N-ethylpyridinium-2-yl) porphyrin (Mn(III)TEPyP) and manganese(III) meso-(tetrakis(4-sulfonato-phenyl)) porphyrinate (Mn(III)TPPS) are able to chemically distinguish between HNO and NO donors, reacting with the former in a fast, efficient, and selective manner with concomitant formation of the {MnNO}(7) complex (k(on(HNO)) approximately equal to 10(5) M(-1) s(-1)), while they are inert or react very slowly with NO donors. DFT calculations and kinetic data suggest that HNO trapping is operative at least in the case of Mn(III)TPPS, while catalytic decomposition of the HNO donors (sodium trioxodinitrate and toluene sulfohydroxamic acid) seems to be the main pathway for Mn(III)TEPyP. In the presence of oxygen, the product Mn(II)TEPyP(NO) oxidizes back to Mn(III)TEPyP, making it possible to process large ratios of nitroxyl donor with small amounts of porphyrin.

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Year:  2005        PMID: 15796534     DOI: 10.1021/ja044632n

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  26 in total

Review 1.  The pharmacology of nitroxyl (HNO) and its therapeutic potential: not just the Janus face of NO.

Authors:  Nazareno Paolocci; Matthew I Jackson; Brenda E Lopez; Katrina Miranda; Carlo G Tocchetti; David A Wink; Adrian J Hobbs; Jon M Fukuto
Journal:  Pharmacol Ther       Date:  2006-11-29       Impact factor: 12.310

2.  Direct detection of nitroxyl in aqueous solution using a tripodal copper(II) BODIPY complex.

Authors:  Joel Rosenthal; Stephen J Lippard
Journal:  J Am Chem Soc       Date:  2010-04-28       Impact factor: 15.419

Review 3.  The specificity of nitroxyl chemistry is unique among nitrogen oxides in biological systems.

Authors:  Wilmarie Flores-Santana; Debra J Salmon; Sonia Donzelli; Christopher H Switzer; Debashree Basudhar; Lisa Ridnour; Robert Cheng; Sharon A Glynn; Nazareno Paolocci; Jon M Fukuto; Katrina M Miranda; David A Wink
Journal:  Antioxid Redox Signal       Date:  2011-03-16       Impact factor: 8.401

Review 4.  Recent advances in the chemical biology of nitroxyl (HNO) detection and generation.

Authors:  Zhengrui Miao; S Bruce King
Journal:  Nitric Oxide       Date:  2016-04-20       Impact factor: 4.427

5.  HNO-Binding in Heme Proteins: Effects of Iron Oxidation State, Axial Ligand, and Protein Environment.

Authors:  Rahul L Khade; Yuwei Yang; Yelu Shi; Yong Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-31       Impact factor: 15.336

Review 6.  The chemistry of nitroxyl-releasing compounds.

Authors:  Jenna F DuMond; S Bruce King
Journal:  Antioxid Redox Signal       Date:  2011-03-02       Impact factor: 8.401

Review 7.  Detection and quantification of nitric oxide-derived oxidants in biological systems.

Authors:  Matías N Möller; Natalia Rios; Madia Trujillo; Rafael Radi; Ana Denicola; Beatriz Alvarez
Journal:  J Biol Chem       Date:  2019-08-12       Impact factor: 5.157

8.  Kinetic feasibility of nitroxyl reduction by physiological reductants and biological implications.

Authors:  Matthew I Jackson; Tae H Han; Laura Serbulea; Andrew Dutton; Eleonora Ford; Katrina M Miranda; K N Houk; David A Wink; Jon M Fukuto
Journal:  Free Radic Biol Med       Date:  2009-07-02       Impact factor: 7.376

Review 9.  Superoxide dismutase mimics: chemistry, pharmacology, and therapeutic potential.

Authors:  Ines Batinić-Haberle; Júlio S Rebouças; Ivan Spasojević
Journal:  Antioxid Redox Signal       Date:  2010-09-15       Impact factor: 8.401

10.  Detailed mechanism of the autoxidation of N-hydroxyurea catalyzed by a superoxide dismutase mimic Mn(III) porphyrin: formation of the nitrosylated Mn(II) porphyrin as an intermediate.

Authors:  József Kalmár; Bernadett Biri; Gábor Lente; István Bányai; Ana Budimir; Mladen Biruš; Ines Batinić-Haberle; István Fábián
Journal:  Dalton Trans       Date:  2012-08-22       Impact factor: 4.390

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