BEC HCl
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Hodoodo CAT#: H530495

CAS#: 222638-67-7 (HCl).

Description: 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 Structure

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BEC HCl
CAS# 222638-67-7 (HCl).
Instruction

Theoretical Analysis

Hodoodo Cat#: H530495
Name: BEC HCl
CAS#: 222638-67-7 (HCl).
Chemical Formula: C5H13BClNO4S
Exact Mass: 0.00
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

Price and Availability

Size Price Availability Quantity
100mg USD 650 2 weeks
200mg USD 1050 2 weeks
500mg USD 1950 2 weeks
1g USD 2850 2 weeks
2g USD 3850 2 weeks
5g USD 5950 2 weeks
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Related CAS #: 222638-67-7 (HCl)   63107-40-4 (free base)    

Synonym: BEC HCl; S-(2-boronoethyl)-L-cysteine.

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

InChi Key: GHPYJLCQYMAXGG-WCCKRBBISA-N

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

SMILES Code: N[C@@H](CSCCB(O)O)C(O)=O.[H]Cl

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 229.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.

4: 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.

5: 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.

6: Pudlo M, Demougeot C, Girard-Thernier C. Arginase Inhibitors: A Rational Approach Over One Century. Med Res Rev. 2016 Nov 15. doi: 10.1002/med.21419. [Epub ahead of print] Review. PubMed PMID: 27862081.

7: Bordage S, Pham TN, Zedet A, Gugglielmetti AS, Nappey M, Demougeot C, Girard-Thernier C. Investigation of Mammal Arginase Inhibitory Properties of Natural Ubiquitous Polyphenols by Using an Optimized Colorimetric Microplate Assay. Planta Med. 2016 Oct 24. [Epub ahead of print] PubMed PMID: 27776374.

8: Chu Y, XiangLi X, Niu H, Wang H, Jia P, Gong W, Wu D, Qin W, Xing C. Arginase inhibitor attenuates pulmonary artery hypertension induced by hypoxia. Mol Cell Biochem. 2016 Jan;412(1-2):91-9. doi: 10.1007/s11010-015-2611-z. PubMed PMID: 26608181.

9: Ohnaka M, Okuda-Ashitaka E, Kaneko S, Ando A, Maeda M, Furuta K, Suzuki M, Takahashi K, Ito S. Induction of arginase II mRNA by nitric oxide using an in vitro model of gyrate atrophy of choroid and retina. Invest Ophthalmol Vis Sci. 2011 Mar 18;52(3):1493-500. doi: 10.1167/iovs.10-5516. PubMed PMID: 20811048.

10: McLarren KW, Cole AE, Weisser SB, Voglmaier NS, Conlin VS, Jacobson K, Popescu O, Boucher JL, Sly LM. SHIP-deficient mice develop spontaneous intestinal inflammation and arginase-dependent fibrosis. Am J Pathol. 2011 Jul;179(1):180-8. doi: 10.1016/j.ajpath.2011.03.018. PubMed PMID: 21640975; PubMed Central PMCID: PMC3123870.

11: Ckless K, Lampert A, Reiss J, Kasahara D, Poynter ME, Irvin CG, Lundblad LK, Norton R, van der Vliet A, Janssen-Heininger YM. Inhibition of arginase activity enhances inflammation in mice with allergic airway disease, in association with increases in protein S-nitrosylation and tyrosine nitration. J Immunol. 2008 Sep 15;181(6):4255-64. PubMed PMID: 18768883; PubMed Central PMCID: PMC2892856.

12: Zhang J, Zhang X, Wu C, Lu D, Guo G, Mao X, Zhang Y, Wang DC, Li D, Zou Q. Expression, purification and characterization of arginase from Helicobacter pylori in its apo form. PLoS One. 2011;6(10):e26205. doi: 10.1371/journal.pone.0026205. PubMed PMID: 22028830; PubMed Central PMCID: PMC3197605.

13: Khan M, Steppan J, Schuleri KH, Ryoo S, Tuday E, Bugaj L, Santhanam L, Berkowitz T, Nyhan D, Shoukas AA, Berkowitz DE. Upregulation of arginase-II contributes to decreased age-related myocardial contractile reserve. Eur J Appl Physiol. 2012 Aug;112(8):2933-41. doi: 10.1007/s00421-011-2257-9. Erratum in: Eur J Appl Physiol. 2012 Dec;112(12):4189. Schuleri, Karl [corrected to Schuleri, Karl H]. PubMed PMID: 22160208.

14: Lewis ND, Asim M, Barry DP, Singh K, de Sablet T, Boucher JL, Gobert AP, Chaturvedi R, Wilson KT. Arginase II restricts host defense to Helicobacter pylori by attenuating inducible nitric oxide synthase translation in macrophages. J Immunol. 2010 Mar 1;184(5):2572-82. doi: 10.4049/jimmunol.0902436. PubMed PMID: 20097867; PubMed Central PMCID: PMC2841360.

15: Prieto CP, Krause BJ, Quezada C, San Martin R, Sobrevia L, Casanello P. Hypoxia-reduced nitric oxide synthase activity is partially explained by higher arginase-2 activity and cellular redistribution in human umbilical vein endothelium. Placenta. 2011 Dec;32(12):932-40. doi: 10.1016/j.placenta.2011.09.003. PubMed PMID: 21962305.

16: Chen B, Calvert AE, Cui H, Nelin LD. Hypoxia promotes human pulmonary artery smooth muscle cell proliferation through induction of arginase. Am J Physiol Lung Cell Mol Physiol. 2009 Dec;297(6):L1151-9. doi: 10.1152/ajplung.00183.2009. PubMed PMID: 19801451.

17: Steppan J, Nyhan D, Berkowitz DE. Development of novel arginase inhibitors for therapy of endothelial dysfunction. Front Immunol. 2013 Sep 17;4:278. doi: 10.3389/fimmu.2013.00278. Review. PubMed PMID: 24062745; PubMed Central PMCID: PMC3774993.

18: Zharikov S, Krotova K, Hu H, Baylis C, Johnson RJ, Block ER, Patel J. Uric acid decreases NO production and increases arginase activity in cultured pulmonary artery endothelial cells. Am J Physiol Cell Physiol. 2008 Nov;295(5):C1183-90. doi: 10.1152/ajpcell.00075.2008. PubMed PMID: 18784379; PubMed Central PMCID: PMC2584985.

19: Peyton KJ, Ensenat D, Azam MA, Keswani AN, Kannan S, Liu XM, Wang H, Tulis DA, Durante W. Arginase promotes neointima formation in rat injured carotid arteries. Arterioscler Thromb Vasc Biol. 2009 Apr;29(4):488-94. doi: 10.1161/ATVBAHA.108.183392. PubMed PMID: 19164802; PubMed Central PMCID: PMC2662760.

20: Ming XF, Rajapakse AG, Carvas JM, Ruffieux J, Yang Z. Inhibition of S6K1 accounts partially for the anti-inflammatory effects of the arginase inhibitor L-norvaline. BMC Cardiovasc Disord. 2009 Mar 13;9:12. doi: 10.1186/1471-2261-9-12. PubMed PMID: 19284655; PubMed Central PMCID: PMC2664787.