Nitric Oxide Synthases: Properties and Catalytic Mechanism

Griffith, Owen W.; Stuehr, Dennis J.

doi:10.1146/annurev.ph.57.030195.003423

Cited by 1,207 publications

(879 citation statements)

References 43 publications

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“…Tilting of the Fe-N NO vector, as described above, is an inherent characteristic of {FeNO} 7 porphyrinates. The Fe-N NO tilt shows an apparent temperature dependence; the tilt is smaller with increased temperature.…”

Section: Molecular Structures -Multiple Temperaturesmentioning

confidence: 94%

Reversible NO Motion in Crystalline [Fe(Porph)(1-MeIm)(NO)] Derivatives

Noll

et al. 2008

Inorg. Chem.

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The synthesis, characterization, and X-ray structures of three low-spin (nitrosyl)iron(II) tetraarylporphyrinates, [Fe(TpXPP)(NO)(1-MeIm)], where X = F (in a triclinic and a monoclinic form) and OCH 3 are reported. All three molecules, at 100 K, have a single orientation of NO. These structures are the first examples of ordered NO's in [Fe(Porph)(NO)(1-MeIm)] complexes. The three new derivatives have similar structural features including a previously unnoted "bowing" of the N NO -Fe-N Im angle caused by a concerted tilting of the axial Fe-N NO and Fe-N Im bonds. Structural features such as the displacement of Fe out of the mean porphyrin plane toward NO, tilting of the Fe-N NO bond off the heme normal, and the asymmetry of the Fe-N por bonds further strengthen and confirm observations from earlier studies. The [Fe(TpXPP)(NO)(1-MeIm)] complexes were also studied at temperatures between 125-350 K to investigate temperature-dependent variations and trends in the coordination group geometry. At varying temperatures (above 150 K), all three derivatives display a second orientation of the NO ligand. The population and depopulation of this second orientation is thermally driven, with no apparent hysteresis. Crystal packing appears to be the significant feature in defining the order/disorder of the NO ligand. The length of the bond trans to NO, Fe-N Im , was also found to be sensitive to temperature variation. The Fe-N Im bond length increases with increased temperature, whereas no other bonds change appreciably. The T-dependent Fe-N Im bond length change and cell volume changes are consistent with a "soft" Fe-N Im bond. Variable temperature measurements show that the N-O stretching frequency changes with the Fe-N Im bond length. Temperature-dependent changes in the Fe-N Im bond length and N-O stretching frequency were also found to be completely reversible with no apparent hysteresis.

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Section: Molecular Structures -Multiple Temperaturesmentioning

confidence: 94%

Reversible NO Motion in Crystalline [Fe(Porph)(1-MeIm)(NO)] Derivatives

Noll

et al. 2008

Inorg. Chem.

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“…A comprehensive description of the enzymology of NO biosynthesis is beyond the scope of this article and has been reviewed extensively elsewhere (for example, (16)(17)(18)(19)). However, of particular relevance to this article, the K m values of O 2 for the three major isoforms differ significantly, indicating · NO biosynthesis can be regulated by O 2 levels, depending on the isoform (19).…”

Section: Regulation Of Nitric Oxide Biosynthesis -General Considerationsmentioning

confidence: 99%

“…A brief review of how · NO production is regulated is provided later in this article; however, for a thorough analysis of NOS enzymology the reader is referred to extensive reviews by others (16)(17)(18)(19).…”

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confidence: 99%

The chemistry of cell signaling by reactive oxygen and nitrogen species and 4-hydroxynonenal

Forman

Fukuto

Miller

et al. 2008

Archives of Biochemistry and Biophysics

219

165

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During the past several years, major advances have been made in understanding how reactive oxygen species (ROS) and nitrogen species (RNS) participate in signal transduction. Identification of the specific targets and the chemical reactions involved still remains to be resolved with many of the signaling pathways in which the involvement of reactive species has been determined. Our understanding is that ROS and RNS have second messenger roles. While cysteine residues in the thiolate (ionized) form found in several classes of signaling proteins can be specific targets for reaction with H 2 O 2 and RNS, better understanding of the chemistry, particularly kinetics, suggests that for many signaling events in which ROS and RNS participate, enzymatic catalysis is more likely to be involved than non-enzymatic reaction. Due to increased interest in how oxidation products, particularly lipid peroxidation products, also are involved with signaling, a review of signaling by 4-hydroxy-2-nonenal (HNE) is included. This article focuses on the chemistry of signaling by ROS, RNS, and HNE and will describe reactions with selected target proteins as representatives of the mechanisms rather attempt to comprehensively review the many signaling pathways in which the reactive species are involved. Keywords signaling; glutathione; thioredoxin; oxidants; reactive oxygen species; thiols; peroxide; nitric oxide; peroxynitrite; 4-hydroxynonenal; cysteine; hydrogen peroxide; protein tyrosine phosphatase; reactive nitrogen species; eNOS; iNOS; nNOS; soluble guanylate cyclase; cGMP; tyrosine nitration; fatty acid nitration; NO-heme; NO-metal complexes; nitrite; protein kinase C; ERK; JNK; p38MAPK; tyrosine kinase receptors; calcium OVERVIEW OF SIGNALING BY REACTIVE SPECIESUnderstanding of the roles of reactive oxygen species (ROS), reactive nitrogen species (RNS) and the lipid peroxidation product, 4-hydroxy-2-nonenal (HNE) in signaling has evolved rapidly during the last decade. This has been markedly helped by identification of the specific targets in signaling pathways. In previous reviews, we defined how ROS, H 2 O 2 in particular,

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“…At the same time NH 2 OHrHCl NOS also can produce N G -hydroxy-L-arginine (HO-Arg) (4.05 g, 58 mmol) was stirred in heated EtOH (35 mL). The ethanolic (16), which can be oxidized by catalase and hydrogen solution of NH 2 OHrHCl was added to the solution of NaOEt and the white solid (NaCl) removed by filtration. To the stirring filtrate was peroxide to give NO 0 (17).…”

mentioning

confidence: 99%

The Cytotoxicity of Nitroxyl: Possible Implications for the Pathophysiological Role of NO

Wink

Feelisch

Fukuto

et al. 1998

Archives of Biochemistry and Biophysics

206

167

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or superoxide, can generate reactive nitrogen oxide spe-AS was found to be cytotoxic to Chinese hamster V79 cies (RNOS) 2 , which can oxidize nitrate, or nitrosate, lung fibroblast cells over a concentration range of 2-4 mM. The presence of equimolar ferricyanide (Fe(III)-other biomolecules (2, 3). RNOS are proposed to medi-(CN 6 ) 30 ), which converts NO 0 to NO, afforded dramatic ate various toxic and cytotoxic mechanisms. In conprotection against AS-mediated cytotoxicity. Treat-trast, NO can protect cells from damage caused by reacment of V79 cells with L-buthionine sulfoximine to re-tive oxygen species (ROS) (4-6), as a result of different duce intracellular glutathione markedly enhanced AS chemical reactions than those involving RNOS (7-10).cytotoxicity, which suggests that GSH is critical for NO participates in chemical reactions associated cellular protection against the toxicity of NO 0 . Fur-with both oxidative and nitrosative stress which can ther experiments showed that low molecular weight have deleterious consequences in vivo. Studies suggest transition metal complexes associated with the forma-that there exists a balance between NO and two of tion of reactive oxygen species are not involved in AS-the major reactive nitrogen oxide species, dinitrogen mediated cytotoxicity since metal chelators had no ef-trioxide (N 2 O 3 ) and peroxynitrite (ONOO 0 ) (11-13) fect. However, under aerobic conditions, AS was more that can determine the toxicological outcome under toxic than under hypoxic conditions, suggesting that oxygen dramatically enhanced AS-mediated cytotoxicity. At a molecular level, AS exposure resulted in DNA 2 Abbreviations used: RNOS, reactive nitrogen oxide species; AS, double strand breaks in whole cells, and this effect was Angelis's salt; DETAPAC, diethylenetriaminepentaacetic acid; DF, desferrioxime; TPH, tempol-H; NADPH, b-nicotinamide adenine dinucleotide phosphate; PBS, phosphate-buffered saline; GSH, intra-1 To whom correspondence and reprint requests should be ad-cellular glutathione; ER, enhancement ratio; ESR, electron spin resonance. dressed. Fax: (301) 480-2238. 66

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Nitric Oxide Synthases: Properties and Catalytic Mechanism

Cited by 1,207 publications

References 43 publications

Reversible NO Motion in Crystalline [Fe(Porph)(1-MeIm)(NO)] Derivatives

Reversible NO Motion in Crystalline [Fe(Porph)(1-MeIm)(NO)] Derivatives

The chemistry of cell signaling by reactive oxygen and nitrogen species and 4-hydroxynonenal

The Cytotoxicity of Nitroxyl: Possible Implications for the Pathophysiological Role of NO

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