Arginase inhibitor 1

• CAT Number: I001319
• CAS Number: 1345808-25-4
• Molecular Formula: C13H27BN2O4
• Molecular Weight: 286.18
• Purity: ≥95%
• Synonyms: (R)-2-amino-6-borono-2-(2-(piperidin-1-yl)ethyl)hexanoic acid
• Target: Metabolic Enzyme/Protease
• Solubility: DMSO: ≥ 48 mg/mL, H2O: ≥ 30 mg/mL
• Storage: Store at -20℃
• IC50: 223 nM (arginases I); 509 nM (arginases II) [1]
• IUPAC Name: (2R)-2-amino-6-borono-2-(2-piperidin-1-ylethyl)hexanoic acid
• InChI: InChI=1S/C13H27BN2O4/c15-13(12(17)18,6-2-3-8-14(19)20)7-11-16-9-4-1-5-10-16/h19-20H,1-11,15H2,(H,17,18)/t13-/m1/s1
• InChIKey: CHPILBYRQPOXMV-CYBMUJFWSA-N
• SMILES: B(CCCC[C@@](CCN1CCCCC1)(C(=O)O)N)(O)O

Arginase inhibitor 1 (Cat.No:I001319) is a small molecule that inhibits the enzyme arginase, which catalyzes the conversion of L-arginine to urea and ornithine. This inhibitor has potential therapeutic applications in the treatment of various diseases, including cancer, cardiovascular diseases, and immune-related disorders.

Reference

[1]. Van Zandt MC, et al. Discovery of (R)-2-amino-6-borono-2-(2-(piperidin-1-yl)ethyl)hexanoic acid and congeners as highly potentinhibitors of human arginases I and II for treatment of myocardial reperfusion injury. J Med Chem. 2013 Mar 28;56(6):2568-80.
Abstract
Recent efforts to identify treatments for myocardial ischemia reperfusion injury have resulted in the discovery of a novel series of highly potent α,α-disubstituted amino acid-based arginase inhibitors. The lead candidate, (R)-2-amino-6-borono-2-(2-(piperidin-1-yl)ethyl)hexanoic acid, compound 9, inhibits human arginases I and II with IC50s of 223 and 509 nM, respectively, and is active in a recombinant cellular assay overexpressing human arginase I (CHO cells). It is 28% orally bioavailable and significantly reduces the infarct size in a rat model of myocardial ischemia/reperfusion injury. Herein, we report the design, synthesis, and structure-activity relationships (SAR) for this novel series of inhibitors along with pharmacokinetic and in vivo efficacy data for compound 9 and X-ray crystallography data for selected lead compounds cocrystallized with arginases I and II.