L-N6-(1-Iminoethyl)lysine dihydrochloride

Product NameL-N6-(1-Iminoethyl)lysine dihydrochloride
CAS159190-45-1
MFC8H18ClN3O2
MW223.7
EINECS
MOL File159190-45-1.mol

Chemical Properties

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

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	37/39-26-36
WGK Germany	3
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ACROS	English

Usage And Synthesis

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 30mg/kg.
Administration:	Intraperitoneally at the end of CLP and at 6h 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 IL1βprotein 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.

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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