| Identification | Back Directory | [Name]
L-N6-(1-IMINOETHYL)LYSINE DIHYDROCHLORIDE | [CAS]
159190-45-1 | [Synonyms]
L-NIL HCL
L-NIL DIHYDROCHLORIDE
L-N6-(1-Iminoethyl)lysine
OQIBCXRAFAHXMM-KLXURFKVSA-N
L-N6-(1-IMINOETHYL)-LYSINE 2HCL
L-N6-(1-IMINOETHYL)LYSINE, DIHCL
L-Lysine ω-acetamidine dihydrochloride
L-N6-(1-IMINOETHYL)LYSINE DIHYDROCHLORIDE
N6-(1-IMINOETHYL)-L-LYSINE DIHYDROCHLORIDE
L-Lysine, N6-(1-iMinoethyl)-, (Hydrochloride) (1:2) | [Molecular Formula]
C8H19Cl2N3O2 | [MDL Number]
MFCD00270890 | [MOL File]
159190-45-1.mol | [Molecular Weight]
260.16 |
| Chemical Properties | Back Directory | [storage temp. ]
-20°C | [solubility ]
DMF: 15 mg/mL; DMSO: 15 mg/mL; Ethanol: 1 mg/mL; PBS: 30 mg/mL; Water: 50 mg/ml | [form ]
White to off-white solid. | [biological source]
synthetic (organic) | [Water Solubility ]
water: 50mg/mL, clear, colorless | [InChI]
1S/C8H17N3O2.2ClH/c1-6(9)11-5-3-2-4-7(10)8(12)13;;/h7H,2-5,10H2,1H3,(H2,9,11)(H,12,13);2*1H/t7-;;/m0../s1 | [InChIKey]
OQIBCXRAFAHXMM-KLXURFKVSA-N | [SMILES]
Cl.Cl.CC(=N)NCCCC[C@H](N)C(O)=O |
| Hazard Information | Back Directory | [Description]
L-NIL is a relatively selective inhibitor of iNOS. It exhibits IC50 values of 0.4-3.3 μM for iNOS as opposed to 8-38 and 17-92 μM for eNOS and nNOS, respectively. L-NIL effectively inhibits iNOS both in vitro and in vivo. L-NIL has been used to demonstrate a critical role for iNOS in the immune response to infection by the protozoan L. major. | [Uses]
L-N6-(1-Iminoethyl)lysine dihydrochloride has been used as an inducible nitric oxide synthase (iNOS) inhibitor:
- to study its effects on leptin-induced modulation of fibronectin type III domain-containing five (FNDC5)/irisin in myocytes and fat cells of murine
- to study its effects on leptin-induced inflammation in hepatocytes
- to block the production of nitric oxide in mice bone marrow mesenchymal stromal cells (BMSCs)
| [Definition]
ChEBI: N(6)-acetimidoyl-L-lysine dihydrochloride is a hydrochloride salt prepared from N(6)-acetimidoyl-L-lysine and two equivalents of hydrogen chloride. A selective inhibitor of inducible nitric oxide synthase. It has a role as an EC 1.14.13.39 (nitric oxide synthase) inhibitor. It contains a N(6)-acetimidoyl-L-lysinium(2+). | [Biochem/physiol Actions]
Selective inhibitor of inducible nitric oxide synthase (iNOS). | [in vivo]
L-NIL (10 and 30 mg/kg, IP) prevents the inflammation, oxidative stress and autophagy induced by renal IR in mice[1]. | Animal Model: | Adult male Balb/c (20-25 g)[1]. | | Dosage: | 10 and 30?mg/kg. | | Administration: | Intraperitoneally at the end of CLP and at 6?h after sepsis induction. | | Result: | Led to a negligible increase in plasma NGAL compared to sham mice.
Led to a significant decrease in both TLR4 and IL1β?protein contents and clusterin transcript.
Showed an increase in NFAT5 mRNA levels, as compared with mice treated with vehicle.
Promoted a decrease in AR protein expression, as compared with animals treated with vehicle.
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| [IC 50]
iNOS | [References]
[1] WILLIAM M. MOORE. L-N6-(1-Iminoethyl)lysine: A Selective Inhibitor of Inducible Nitric Oxide Synthase[J]. Journal of Medicinal Chemistry, 1994, 37 23: 3886-3888. DOI: 10.1021/jm00049a007
[2] STEPHAN K. GRANT. Structural Requirements for Human Inducible Nitric Oxide Synthase Substrates and Substrate Analogue Inhibitors[J]. Biochemistry Biochemistry, 1998, 37 12: 4174-4180. DOI: 10.1021/bi972481d
[3] STEFFEN STENGER . l-N6-(1-Iminoethyl)-lysine potently inhibits inducible nitric oxide synthase and is superior to NG-monomethyl-arginine in vitro and in vivo[J]. European journal of pharmacology, 1995, 294 2: Pages 703-712. DOI: 10.1016/0014-2999(95)00618-4
[4] M. BUDZINSKI. Inhibition of inducible nitric oxide synthase in persistent pain[J]. Life sciences, 1999, 66 4: Pages 301-305. DOI: 10.1016/s0024-3205(99)00421-x
[5] W S FARACI. 2-Amino-4-methylpyridine as a potent inhibitor of inducible NO synthase activity in vitro and in vivo.[J]. British Journal of Pharmacology, 1996, 119 6: 1101-1108. DOI: 10.1111/j.1476-5381.1996.tb16010.x
[6] A DIEFENBACH. Type 1 interferon (IFNalpha/beta) and type 2 nitric oxide synthase regulate the innate immune response to a protozoan parasite.[J]. Immunity, 1998, 8 1: 77-87. DOI: 10.1016/s1074-7613(00)80460-4 |
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