BEC HCl

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.

Product information

CAS Number: 222638-67-7

Molecular Weight: 229.49

Formula: C5H13BClNO4S

Synonym:

S-(2-boronoethyl)-L-cysteine

BEC HCl

Chemical Name:    S-(2-boronoethyl)-L-cysteine hydrochloride

Smiles: Cl.N[C@@H](CSCCB(O)O)C(O)=O

InChiKey: GHPYJLCQYMAXGG-WCCKRBBISA-N

InChi: 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

Technical Data

Appearance: Solid Power.

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

In Vitro:

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.

In Vivo:

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.

References:

1. 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.
2. 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.
3. 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.

Products are for research use only. Not for human use.