Methods to Quantify Nitric Oxide en vivo: Concepts and Considerations
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1 Methods to Quantify Nitric Oxide en vivo: Concepts and Considerations R
2 Atmospheric Nitrogen Oxides Los Angeles
3 Nitric Oxide N O Colorless Gas Free Radical Potent Vasodilator (EDRF)
4 NO Production by Nitric Oxide Synthase H 2 N + NH 3 H 2 N N- OH H 2 N O NH NH NH O 2 NADPH O NADPH + NO - OOC NH - 3 OOC NH - 3 OOC NH 3 L-Arginine N G -Hydroxy-L-Arginine L-Citrulline
5 Nitric Oxide Synthase (NOS) Isoenzymes NOS Constitutive Inducible endothelial NOS (enos; NOS 3) neuronal NOS (nnos; NOS 1) inducible NOS (inos; NOS 2)
6 Nitric Oxide is a Pleiotropic Regulator of the Immune, Cardiovascular and Nervous Systems
7 The Chemistry of Nitric Oxide Dictates its Physiological Activity L-Arginine enos nnos inos NO O 2 or O 2 - Metal Complexes/Alkyl Radicals RNOS Guanylate Cyclase Cytochromes Lipid Radicals IRP-1 Ribonucleotide reductase Direct Indirect Nitration Nitrotyrosine Nitroguanosine Nitrosation Nitrosothiols Nitrosamines Oxidation DNA Strand Breaks Lipid Peroxidation Hydroxylation
8 Methods to Quantify NO and its Metabolites in Extracellular Fluids and/or Tissue Gas Phase Chemiluminescence (NO) Spectrophotometric Assays for Oxidized Metabolites of NO (Nitrite/Nitrate) Griess Assay Fluorescence Assay DAF-2 Bio-imaging Spectrophotometric Assays for RSNOs Saville Assay Modified Saville Assay
9 Methods to Quantify NO and its Metabolites in Extracellular Fluids and/or Tissue Gas Phase Chemiluminescence (NO) Spectrophotometric Assays for Oxidized Metabolites of NO (Nitrite/Nitrate) Griess Assay Fluorescence Assay DAF-2 Bio-imaging Spectrophotometric Assays for RSNOs Saville Assay Modified Saville Assay
10 NO Detection by Gas Phase Chemiluminescence Detection Principle: NO is purged from an aqueous solution using an innert gas such as Ar or He and transferred to a mixing chamber where it reacts with O 3 under reduced pressure. NO + O 3 NO 2 * + O 2 NO 2 * NO 2 + h. υ The light emitted by excited NO 2 upon returning to the ground state is measured by photon counting (fmol-pmol). Not very useful when attempting to quantify NO in physiological fluids such as serum, plasma or urine. Why?
11 Autoxidation of NO 2NO + O 2 2NO 2 2NO + 2NO 2 2N 2 O 3 2N 2 O 3 + H 2 O 4NO H + 4NO + O 2 + 2H 2 O 4NO H +
12 Methods to Quantify NO and its Metabolites in Extracellular Fluids and/or Tissue Gas Phase Chemiluminescence (NO) Spectrophotometric Assays for Oxidized Metabolites of NO (Nitrite/Nitrate) Griess Assay Fluorescence Assay DAF-2 Bio-imaging Spectrophotometric Assays for RSNOs Saville Assay Modified Saville Assay
13 Griess Reaction Sulfanilamide H 2 NSO + NO + +H + 3 NH 2 NO H 2 NSO 3 N N + NH NH 2 N-(1-Naphthyl)ethylenediamine H 2 NSO 3 N N NH NH 2 Azo Dye (λ max = 540 nm)
14 Although Nitrite is Produced from NO Autoxidation, Nitrate is the Major NO-Derived Metabolite in Plasma and Urine: Role of Hemoglobin 2Hb-Fe +2 O 2 + 3NO H + 2Hb-Fe NO H2 O 4Hb-Fe +2 O 2 + 4NO H + 4Hb-Fe NO O2 + 2H 2 O Hb-Fe +2 O 2 + NO Hb-Fe +3 + NO 3 -
15 Quantification of NO-Derived NO 3- and NO 2 - in Extracellular Fluids NR NO 3- + FAD + NADPH NO 2- + NADP + Nitrate Reductase (NR) Converts all NO 3- to NO 2 - All unreacted NADPH must be oxidized NO 2- quantified by Griess Reaction Grisham, M.B. et.al Quantitation of nitrate and nitrite in extracellular fluids. Methods Enzymol :
16 LPS Induces Nitric Oxide Production In Vivo Serum Nitrate and Nitrite (µm) Grisham et. al. Meth Enz, 1996 * 0 Saline +LPS
17 Measurement of NO 2- /NO 3- in Plasma Using the Griess Reagent: Problems and Considerations Heparin may produce precipitant upon addition of Griess Reagent. Addition of protamine sulfate will remove heparin (Suggestion: Use serum or calcium chelators such as EDTA or citrate). NO 2- /NO 3- may be underestimated in hemolyzed plasma or Serum due to Hb-catalyzed oxidation of NO 2- (Suggestion: Ultrafilterplasma or serum to obtain a low molecular weight fraction; < 15,000). The presence of some plasma or serum-associated proteins may inhibit nitrate reductase (Suggestion: Ultrafilter plasma or serum to obtain a low molecular weight fraction).
18 Simultaneous Quantification of Nitrite and Nitrate by HPLC Using the Griess Reaction Sensitivity: Rodriguez and Feelisch PNAS 100:336, nm NO nm NO 3-1 pmol/ml for either anion (injection volume 100µl) No interference by proteins or colored species
19 Sources of NO 2- /NO 3- in Extracellular Fluids (Blood, Lymph, Urine, Saliva): NO Bacteria (Enteric; Oral) Diet (need for fasting or nitrate/ nitrite-free chow)
20 Methods to Quantify NO and its Metabolites in Extracellular Fluids and/or Tissue Gas Phase Chemiluminescence (NO) Spectrophotometric Assays for Oxidized Metabolites of NO (Nitrite/Nitrate) Griess Assay Fluorescence Assay DAF-2 Bio-imaging Spectrophotometric Assays for RSNOs Saville Assay Modified Saville Assay
21 N-nitrosation of 2,3 diaminonaphthalene (DAN) to yield 2,3-naphthotriazole (NAT) DAN NO 2 - +H + NH 2 NO + H N NO NAT λ ex = 375nm λ em = 415nm NH 2 N N NH -H 2 O NH 2 N NH 2 N +
22 N-Nitrosation of DAN By Extravasated PMNs Triazole Formation (nm) Grisham et. al, Gastroenterology, x10 6 PMNs 2x10 6 PMNs 1x10 6 PMNs Time (hr)
23 Methods to Quantify NO and its Metabolites in Extracellular Fluids and/or Tissue Gas Phase Chemiluminescence (NO) Spectrophotometric Assays for Oxidized Metabolites of NO (Nitrite/Nitrate) Griess Assay Fluorescence Assay DAF-2 Bio-imaging Spectrophotometric Assays for RSNOs Saville Assay Modified Saville Assay
24 Bioimaging of Nitric Oxide Using Diaminofluoresceine-2 (DAF-2) DAF-2 DA DAF-2 DAF-2 T NH 2 NH 2 N N H H 2 N H 2 N N O esterases COO - NO x COO - O AcO O non-fluorescent, cell-permeable OAc - O O O non-fluorescent - O O fluorescent, Ex 495 nm, Em 515 nm O Advantages: Sensitivity for NO (5 nm in vitro) with high temporal and spatial resolution. No cross-reactivity to NO 2- /NO 3- and ONOO - Kojima et al., Biol.Pharm. Bull. (1997) Assay limitations: Possible interference by reducing agents and divalent cations, requires standardized illumination conditions
25 Propagation of NO Wave during Stimulation of Endothelial Cells with the Calcium Ionophor, A23187 (1 µm) t = min 1 min 1.5 min 2 min 5 min Feelisch et. al. Unpublished Observations
26 The Chemistry of Nitric Oxide Dictates its Physiological Activity L-Arginine enos nnos inos NO O 2 RNOS Metal Complexes/Alkyl Radicals Guanylate Cyclase Cytochromes C,O,N Radicals (Lipid Radicals) Direct Indirect Nitration Nitrotyrosine Nitroguanosine Nitrosation Nitrosothiols Nitrosamines Oxidation DNA Strand Breaks Lipid Peroxidation Hydroxylation
27 Physiological Roles of Nitrosothiols (RSNOs) RSNOs Potent vasorelaxants. Antiplatelet activity. S-Nitrosoglutathione (GSNO) S-Nitrosoalbumin (AlbSNO) S-Nitrosohemoglobin (HbSNO) Antimicrobial activity. Regulation of vasodilation/ oxygenation (hemoglobin). Intermediates in the metabolism of organic nitrites and nitrates. Regulation of cell signaling/ protein functions.
28 NO-Dependent Formation of S-Nitrosothiols (RSNOs): Large Amounts of NO 2NO + O 2 2 NO 2 2 NO NO 2 N 2 O 3 2 N 2 O RSH 2 RSNO + 2 NO 2 - RSNOs S-Nitrosohemoglobin (SNOHb) S-Nitrosoglutathione (SNOGSH) S-Nitrosoalbumin (SNOAlb)
29 NO-Dependent Formation of S-Nitrosothiols (RSNOs): Physiological Levels of Oxygen, NO and RSH 2NO + O 2 2 NO 2 2 NO RSH 2 NO RS + 2H + 2 NO + 2 RS 2 RSNO RSNOs S-Nitrosohemoglobin (SNOHb) S-Nitrosoglutathione (SNOGSH) S-Nitrosoalbumin (SNOAlb)
30 Methods to Quantify NO and its Metabolites in Extracellular Fluids and/or Tissue Gas Phase Chemiluminescence (NO) Spectrophotometric Assays for Oxidized Metabolites of NO (Nitrite/Nitrate) Griess Assay Fluorescence Assay DAF-2 Bio-imaging Spectrophotometric Assays for RSNOs Saville Assay Modified Saville Assay
31 Saville Reaction RSNO + Hg +2 RS - + Hg +3 + NO +
32 Sulfanilamide Saville/Griess Reaction H 2 NSO 3 NH 2 + NO + + RS - RSNO + Hg +2 + H 2 NSO 3 N N + NH NH 2 N-(1-Naphthyl)ethylenediamine H 2 NSO 3 N N NH NH 2 Azo Dye (λ max = 540 nm)
33 Methods to Quantify NO and its Metabolites in Extracellular Fluids and/or Tissue Gas Phase Chemiluminescence (NO) Spectrophotometric Assays for Oxidized Metabolites of NO (Nitrite/Nitrate) Griess Assay Fluorescence Assay DAF-2 Bio-imaging Spectrophotometric Assays for RSNOs Saville Assay Modified Saville Assay
34 Fluorometric Determination of S-Nitrosothiols (RSNO) H NH 2 N NO DAN NH 2 NO + NH 2 RSNO + Hg +2 -H 2 O NAT N N NH N NH 2 N +
35 S-Nitrosothiol Concentration (nm) S-Nitrosothiol Formation in Blood of LPS-Treated Rats * SNO-Alb SNO-Hb Control Jourd heuil et al BBRC, 2000 * + LPS
36 The Chemistry of Nitric Oxide Dictates its Physiological Activity L-Arginine enos nnos inos NO O 2 - RNOS Metal Complexes/Alkyl Radicals Guanylate Cyclase Cytochromes C,O,N Radicals (Lipid Radicals) Direct Indirect Nitration Nitrotyrosine Nitroguanosine Nitrosation Nitrosothiols Nitrosamines Oxidation DNA Strand Breaks Lipid Peroxidation Hydroxylation
37 Interaction Between Superoxide and Nitric Oxide: Formation of Peroxynitrite/Peroxynitrous Acid + H + O 2- + NO ONOO - ONOO - + H + ONOOH ONOOH ONOOH * ( OH. + NO 2. ) ONOOH * NO 3- + H + Sum: O 2- + NO NO 3 -
38 Peroxynitrite Nitrates Tyrosine to Yield 3-Nitrotyrosine Tyrosine OH 3-Nitrotyrosine OH + ONOO - NO 2 R R
39 3-Nitrotyrosine Formation in vivo: Specific Footprint for Peroxynitrite?
40 Generation of 3-Nitrotyrosine ONOO NO 2 + H + OH NO 2 O 2 NO NO 2 HOCl + NO 2 _ R Hemoproteins (MPO,Mb) _ + H 2 O 2 + NO 2 O 2 HNO
41 250 Myoglobin-Catalyzed Formation of 3-Nitrotyrosine (3-NT) 3-Nitrotyrosine Formation (um) Kilinc and Grisham BBRC, 2001 Mb H 2 O 2 + NO 2- + Tyr 3NT Time (min.)
42 LSU Health Sciences Center Martin Feelisch (NitroMed) Steve Laroux (Harvard) Kamer Kilinc (Ankara Univ) Albany College of Medicine David Jourd heuil Grambling State University Allen M. Miles LSU National Cancer Institute David A. Wink Mike Espey Katrina Miranda (Univ Arizona)
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