Structure of a dinitrosyliron complex (DNIC)
In biochemistry , dinitrosyl iron complexes (DNIC' s) are coordination complexes with the formula [Fe(NO)2 (SR)2 ]− . Together with Roussin esters (Fe2 (NO)4 (SR)2 ), they result from the degradation of iron-sulfur proteins by nitric oxide. Commonly the thiolate ligands are cysteinyl residues or glutathione. These metal nitrosyl complexes have attracted much attention because they serve as biochemical signals in response to oxidative stress, manifested in the formation of NO. The anions are tetrahedral.[ 1] [ 2]
References
^ Crack, J. C.; Green, J.; Thomson, A. J.; Brun, N. E. L. (2014). "Iron–Sulfur Clusters as Biological Sensors: The Chemistry of Reactions with Molecular Oxygen and Nitric Oxide". Accounts of Chemical Research . 47 (10): 3196– 3205. doi:10.1021/ar5002507 . PMID 25262769 .
^ Jessica Fitzpatrick; Eunsuk Kim (2015). "Synthetic Modeling Chemistry of Iron–Sulfur Clusters in Nitric Oxide Signaling". Acc. Chem. Res . 48 (8): 2453– 2461. doi:10.1021/acs.accounts.5b00246 . PMID 26197209 .
Nitric oxide signaling modulators
Forms 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
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
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
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)
See also: Receptor/signaling modulators