BEC HCl
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 530495

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.


Price and Availability

Size
Price

100mg
USD 650
1g
USD 2850
Size
Price

200mg
USD 1050
2g
USD 3850
Size
Price

500mg
USD 1950
5g
USD 5950

BEC HCl, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 530495
Name: BEC HCl
CAS#: 222638-67-7 (HCl).
Chemical Formula: C5H13BClNO4S
Exact Mass:
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


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


Technical Data

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).

Harmonized System Code:
293490


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.

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.