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Nitrosylation is the general term for covalent incorporation of a nitric oxide "nitrosyl" moiety into another (usually organic) molecule. There are multiple chemical mechanisms by which this can be achieved; including biological enzymes and industrial processes. The biological functions of nitrosylation are particularly important as S-nitrosylation, the conjugation of NO to cysteine thiols in proteins, is an important part of cell signalling.[1] Coordination of NO to transition metals to give metal nitrosyl complexes, is also referred to as nitrosylation.[2]
See also
Nitrosation
References
Mannick, Joan B.; Schonhoff, Christopher M. (7 July 2009). "Review: NO Means No and Yes: Regulation of Cell Signaling by Protein Nitrosylation". Free Radical Research. 38 (1): 1–7. doi:10.1080/10715760310001629065. PMID 15061648. S2CID 21787778.
Hayton, T. W.; Legzdins, P.; Sharp, W. B. (2002). "Coordination and Organometallic Chemistry of Metal-NO Complexes". Chem. Rev. 102 (1): 935–991. doi:10.1021/cr000074t. PMID 11942784.
vte
Nitric oxide signaling modulators
Forms
Nitroxyl anion (NO−; oxonitrate(1-), hyponitrite anion) Nitric oxide (NO⋅; nitrogen monoxide) Nitrosonium (NO+; nitrosyl cation)
Targets
sGC
Activators/stimulators: Ataciguat BAY 41-2272 BAY 41-8543 BAY 60-4552 BI-703704 Cinaciguat (BAY 58-2667) GSK-2181236A Praliciguat Riociguat Vericiguat
Inhibitors: ODQ
NO donors
(prodrugs)
Nitrates: Diethylene glycol dinitrate (DEGDN) Erythritol tetranitrate (ETN) Ethylene glycol dinitrate (EGDN; nitroglycol) Isosorbide mononitrate (ISMN) Isosorbide dinitrate (ISDN) Itramin tosilate Mannitol hexanitrate Naproxcinod (nitronaproxen; AZD-3582, HCT-3012) NCX-466 NCX-2216 NCX-4016 NCX 4040 NCX-4215 Nicorandil Nipradilol (K-351) Nitrate (NO−
3) Nitroatorvastatin (NCX-6560) Nitroflurbiprofen (HCT-1026) Nitrofluvastatin Nitroglycerin (glyceryl trinitrate (GTN)) Nitropravastatin (NCX-6550) Pentaerithrityl tetranitrate (PETN) Propatylnitrate Propylene glycol dinitrate (PGDN) Sodium trioxodinitrate (Angeli's salt) Tenitramine Trolnitrate
Nitroso compounds/nitrites: Nitrite (NO−
2); O-Nitroso compounds (alkyl nitrites): Amyl nitrite (isoamyl nitrite, isopentyl nitrite) Cyclohexyl nitrite Ethyl nitrite Hexyl nitrite Isobutyl nitrite (2-methylpropyl nitrite) Isopropyl nitrite Methyl nitrite n-Butyl nitrite Pentyl nitrite tert-Butyl nitrite; S-Nitroso compounds (thionitrites): LA810 S-Nitrosoalbumin (SNALB) S-Nitrosated AR545C S-Nitroso-N-acetylcysteine (SNAC) S-Nitroso-N-acetylpenicillamine (SNAP) S-Nitroso-N-valerylpenicillamine (SNVP) S-Nitrosocaptopril (SNO-Cap) S-Nitrosocysteine (SNC, CysNO, SNO-Cys) S-Nitrosodiclofenac S-Nitrosoglutathione (GSNO, SNOG) SNO-t-PA SNO-vWF; N-Nitroso compounds (e.g., nitrosamines): SIN-1A
Nitrosyl compounds: Metal nitrosyl complexes: Roussin's black salt Roussin's red salt Sodium nitroprusside (SNP)
NONOates (diazeniumdiolates): Diethylamine/NO (DEA/NO) Diethylenetriamine/NO (DETA/NO) GLO/NO JS-K Methylamine hexamethylene methylamine/NO (MAHMA/NO) PROLI/NO Spermine/NO (SPER/NO) V-PYRRO/NO
Heterocyclic compounds: Furoxans: Furoxan REC15/2739; Sydnonimines: Feprosidnine Linsidomine (SIN-1) Molsidomine (SIN-10) Sydnonimine
Unsorted: Cimlanod FK-409 FR144220 FR146881 N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide
Enzyme
(inhibitors)
NOS
nNOS
3-Bromo-7-nitroindazole 3-Chloroindazole 3-Chloro-5-nitroindazole 5-Nitroindazole 6-Nitroindazole 7-Nitroindazole A-84643 Aminoguanidine (pimagedine) ARL-17477 Indazole N5-(1-Iminoethyl)-L-ornithine (L-NIO) Nω-Methyl-L-arginine (L-NMA) Nω-Propyl-L-arginine (L-NPA) Nitroarginine (NNA, NOARG) Pentamidine isethionate TRIM
iNOS
1-Amino-2-hydroxyguanidine 2-Ethylaminoguanidine 2-Iminopiperidine 1400W AEITU Aminoguanidine (pimagedine) AMT AR-C 102222 BYK-191023 Canavanine Cindunistat (SD-6010) EITU IPTU MITU N5-(1-Iminoethyl)-L-ornithine (L-NIO) N6-(1-Iminoethyl)-L-lysine (L-NIL) Nω-Methyl-L-arginine (L-NMA) Ronopterin (VAS-203) TRIM
eNOS
Aminoguanidine (pimagedine) N5-(1-Iminoethyl)-L-ornithine (L-NIO) Nω-Methyl-L-arginine (L-NMA) Nitroarginine (NNA, NOARG)
Unsorted
Asymmetric dimethylarginine (ADMA) CKD-712 Guanidinoethyldisulfide (GED) GW-273629 Indospicine KD-7040 Nitroarginine methyl ester (NAME) NCX-456 NXN-462 ONO-1714 VAS-2381
Arginase
ABH Nω-Hydroxy-L-arginine (NOHA) chlorogenic acid ginseng epicatechin ornithine norvaline lysine alpha aminoacids
CAMK
Calmidazolium W-7
Others
Precursors: L-Arginine Nω-Hydroxy-L-arginine (NOHA)
Cofactors: NADPH FAD FMN Heme BH4 CaM O2 Ca2+
Indirect/downstream NO modulators: ACE inhibitors/AT-II receptor antagonists (e.g., captopril, losartan) ETB receptor antagonists (e.g., bosentan) L-Type calcium channel blockers (e.g., dihydropyridines: nifedipine) Nebivolol (beta blocker) PDE5 inhibitors (e.g., sildenafil) non-selective PDE inhibitors (e.g., caffeine) PDE9 inhibitors (e.g., paraxanthine) cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil) Statins (e.g., simvastatin)
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