N-(5-AMINO-5-CARBOXYPENTYL)-ACETAMIDINE
N-(5-AMINO-5-CARBOXYPENTYL)-ACETAMIDINE Basic information
- Product Name:
- N-(5-AMINO-5-CARBOXYPENTYL)-ACETAMIDINE
- Synonyms:
-
- N-(5-AMINO-5-CARBOXYPENTYL)-ACETAMIDINE
- N-EPSILON-ACETIMIDOYL-L-LYSINE
- N-EPSILON-ACETIMIDOYL-L-LYSIN-EPSILON
- H-LYS(1-IMINOETHYL)-OH
- H-LYS(ACETIMIDOYL)-OH
- LYSINE(ACETIMIDOYL)-OH
- N-(5-Amino-5-carboxypentyl
- Ne-Acetimidoyl-L-lysine
- CAS:
- 53774-63-3
- MF:
- C8H17N3O2
- MW:
- 187.24
- Mol File:
- 53774-63-3.mol
N-(5-AMINO-5-CARBOXYPENTYL)-ACETAMIDINE Chemical Properties
- Boiling point:
- 335.2±52.0 °C(Predicted)
- Density
- 1.22±0.1 g/cm3(Predicted)
- storage temp.
- -15°C
- solubility
- Water: 50 mg/mL (267.04 mM); DMSO: < 1 mg/mL (insoluble or slightly soluble)
- form
- Solid
- pka
- 2.52±0.24(Predicted)
- color
- White to off-white
N-(5-AMINO-5-CARBOXYPENTYL)-ACETAMIDINE Usage And Synthesis
Uses
L-NIL is an inducible NO synthase inhibitor, with an IC50 of 3.3 μM for miNOS[1][2][3].
Biological Activity
L-NIL is an inhibitor of inducible nitric oxide synthase (iNOS) with an IC50 value of 3.3 μM for miNOS.
in vitro
L-NIL produces a concentration-dependent inhibition of both the mouse inducible NOS (miNOS) and the rat brain constitutive NOS (rcNOS) and is considerably more potent for miNOS. The IC 50 values for L-NIL with miNOS and rcNOS are 3.3 and 92 pM, respectively, indicating that it is 28-fold more selective for miNOS. In addition, L-NIL has approximately 6-fold greater potency for miNOS than either L -NMA or L-NNA.
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. |
target
IC50: 3.3 μM (mouse inducible NO synthase), 92 μM (rat brain constitutive NO synthase)
IC 50
iNOS
References
[1] Consuelo Pasten, et al. 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. DOI:10.1152/ajprenal.00398.2018
[2] Sharon Angela Tanuseputero, et al. Intravenous Arginine Administration Downregulates NLRP3 Inflammasome Activity and Attenuates Acute Kidney Injury in Mice with Polymicrobial Sepsis. Mediators Inflamm. 2020 May 11;2020:3201635. DOI:10.1155/2020/3201635
[3] Moore WM, et al. L-N6-(1-iminoethyl)lysine: a selective inhibitor of inducible nitric oxide synthase. J Med Chem. 1994 Nov 11;37(23):3886-8. DOI:10.1021/jm00049a007
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