BEC, also known as S-(2-boronoethyl)-L-cysteine, is an a slow-binding and competitive Arginase II inhibitor with Ki of 0.31 μM (ph 7.5). BEC significantly enhances NO-dependent relaxation of human penile corpus canvernosum smooth muscle in vitro at concentrations between 0.1-1.0 mM. S-(2-boronoethyl)-L-cysteine binds to arginase as a transition state analogue and enhances smooth muscle relaxation in human penile corpus cavernosum.
Chemical Formula: C5H13BClNO4S
Molecular Weight: 229.482
Elemental Analysis: C, 26.17; H, 5.71; B, 4.71; Cl, 15.45; N, 6.10; O, 27.89; S, 13.97
InChi Code: InChI=1S/C5H12BNO4S.ClH/c7-4(5(8)9)3-12-2-1-6(10)11;/h4,10-11H,1-3,7H2,(H,8,9);1H/t4-;/m0./s1
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The X-ray crystal structure of the arginase-BEC complex has been determined at 2.3 A resolution from crystals perfectly twinned by hemihedry. The structure of the complex reveals that the boronic acid moiety undergoes nucleophilic attack by metal-bridging hydroxide ion to yield a tetrahedral boronate anion that bridges the binuclear manganese cluster, thereby mimicking the tetrahedral intermediate (and its flanking transition states) in the arginine hydrolysis reaction.
Administration of the arginase inhibitor BEC decreases arginase activity and causes alterations in NO homeostasis, which are reflected by increases in S-nitrosylated and nitrated proteins in the lungs from inflamed mice. BEC enhances perivascular and peribronchiolar lung inflammation, mucus metaplasia, NF-κB DNA binding, and mRNA expression of the NF-κB-driven chemokine genes CCL20 and KC, and leads to further increases in airways hyperresponsiveness.
Kim NN, Cox JD, Baggio RF, Emig FA, Mistry SK, Harper SL, Speicher DW, Morris SM Jr, Ash DE, Traish A, Christianson DW. Probing erectile function: S-(2-boronoethyl)-L-cysteine binds to arginase as a transition state analogue and enhances smooth muscle relaxation in human penile corpus cavernosum. Biochemistry. 2001 Mar 6;40(9):2678-88. PubMed PMID: 11258879.
Kim SH, Langford ML, Boucher JL, Testerman TL, McGee DJ. Helicobacter pylori arginase mutant colonizes arginase II knockout mice. World J Gastroenterol. 2011 Jul 28;17(28):3300-9. doi: 10.3748/wjg.v17.i28.3300. PubMed PMID: 21876618; PubMed Central PMCID: PMC3160534.
Martens CR, Kuczmarski JM, Lennon-Edwards S, Edwards DG. Impaired L-arginine uptake but not arginase contributes to endothelial dysfunction in rats with chronic kidney disease. J Cardiovasc Pharmacol. 2014 Jan;63(1):40-8. doi: 10.1097/FJC.0000000000000022. PubMed PMID: 24084210.
You H, Gao T, Cooper TK, Morris SM Jr, Awad AS. Arginase inhibition: a new treatment for preventing progression of established diabetic nephropathy. Am J Physiol Renal Physiol. 2015 Sep 1;309(5):F447-55. doi: 10.1152/ajprenal.00137.2015. PubMed PMID: 26041444; PubMed Central PMCID: PMC4556892.
You H, Gao T, Cooper TK, Morris SM Jr, Awad AS. Arginase inhibition mediates renal tissue protection in diabetic nephropathy by a nitric oxide synthase 3-dependent mechanism. Kidney Int. 2013 Dec;84(6):1189-97. doi: 10.1038/ki.2013.215. PubMed PMID: 23760286; PubMed Central PMCID: PMC3783645.
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