Description: L-NIL is a selective inhibitor of inducible nitric oxide synthase (iNOS) (IC50 = 3.3 μM for miNOS) with anti-inflammatory activity. L-NIL has an IC50 of 3.3 microM for miNOS compared to an IC50 of 92 microM for rat brain constitutive NOS indicating that L-NIL is 28-fold more selective for inducible NOS. L-N5-(1-Iminoethyl)ornithine (L-NIO), which differs from L-NIL by having one less methylene group, has very similar potency for inducible NOS, but lacks selectivity. DL-N7-(1-Iminoethyl)homolysine was also synthesized and found to be substantially less potent than L-NIL or L-NIO, with intermediate selectivity for inducible NOS. These data suggest that L-NIL may be useful as a selective inhibitor of inducible NOS for determining the role of this enzyme in disease models.

Physicochemical Properties

Molecular Formula	C8H17N3O2
Molecular Weight	187.23948
Exact Mass	187.132
CAS #	53774-63-3
Related CAS #	L-NIL hydrochloride;150403-89-7;L-NIL dihydrochloride;159190-45-1
PubChem CID	2733506
Appearance	White to off-white solid powder
LogP	1.346
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Heavy Atom Count	13
Complexity	192
Defined Atom Stereocenter Count	1
SMILES	CC(=NCCCC[C@@H](C(=O)O)N)N
InChi Key	ONYFNWIHJBLQKE-ZETCQYMHSA-N
InChi Code	InChI=1S/C8H17N3O2/c1-6(9)11-5-3-2-4-7(10)8(12)13/h7H,2-5,10H2,1H3,(H2,9,11)(H,12,13)/t7-/m0/s1
Chemical Name	(2S)-2-amino-6-(1-aminoethylideneamino)hexanoic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Both rat brain constitutive NOS (rcNOS) and mouse inducible NOS (miNOS) were inhibited concentration-dependently by L-NIL, with rcNOS being considerably more potent than miNOS. L-NIL was 28 times more selective for miNOS than rcNOS, as seen by its IC50 values of 3.3 and 92 pM with miNOS and rcNOS, respectively. Furthermore, L-NIL has a potency against miNOS that is about six times greater than that of L-NMA or L-NNA [3].
ln Vivo	In mouse kidneys, L-NIL (10 and 30 mg/kg, IP) inhibits oxidative damage, autophagy, and inflammation brought on by IR [1].
Animal Protocol	Animal/Disease Models: Adult male Balb/c (20-25 g)[1]. Doses: 10 and 30 mg/kg. Route of Administration: Intraperitoneally at the end of CLP and at 6 h after sepsis induction. Experimental Results: 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. demonstrated 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.
References	[1]. l-NIL prevents the ischemia and reperfusion injury involving TLR-4, GST, clusterin, and NFAT-5 in mice. Am J Physiol Renal Physiol. 2019 Apr 1;316(4):F624-F634. [2]. Intravenous Arginine Administration Downregulates NLRP3 Inflammasome Activity and Attenuates Acute Kidney Injury in Mice with Polymicrobial Sepsis. Mediators Inflamm. 2020 May 11;2020:3201635. [3]. L-N6-(1-iminoethyl)lysine: a selective inhibitor of inducible nitric oxide synthase. J Med Chem. 1994 Nov 11;37(23):3886-8.
Additional Infomation	N(6)-acetimidoyl-L-lysine is an L-lysine derivative that is L-lysine in which one of the hydrogens attached to N(6) is substituted by an acetimidoyl group It is a L-lysine derivative and a non-proteinogenic L-alpha-amino acid. It is a conjugate acid of a N(6)-acetimidoyl-L-lysinium(2+).

Solubility Data

Solubility (In Vitro)	H2O : ~50 mg/mL (~267.04 mM) DMSO : ~1 mg/mL (~5.34 mM)
Solubility (In Vivo)	Solubility in Formulation 1: 100 mg/mL (534.07 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.3407 mL	26.7037 mL	53.4074 mL
	5 mM	1.0681 mL	5.3407 mL	10.6815 mL
	10 mM	0.5341 mL	2.6704 mL	5.3407 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.