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MedKoo Cat#: 561759 | Name: ABH Hydrochloride
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Description:

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

ABH Hydrochloride is an arginase inhibitor, enhancing both male and female sexual arousal responses. Oral inhibition of arginase with ABH results in improved erectile function in aged rats, resulting in erectile hemodynamics similar to young rats. This represents the first documentation of systemic arginase inhibition positively affecting corporal cavernosal function. ABH is considered a reference compound in arginase inhibition.

Chemical Structure

ABH Hydrochloride
ABH Hydrochloride
CAS#194656-75-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 561759

Name: ABH Hydrochloride

CAS#: 194656-75-2 (HCl)

Chemical Formula: C6H15BClNO4

Exact Mass: 0.0000

Molecular Weight: 211.44

Elemental Analysis: C, 34.08; H, 7.15; B, 5.11; Cl, 16.77; N, 6.62; O, 30.27

Price and Availability

Size Price Availability Quantity
5mg USD 425.00 2 Weeks
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Related CAS #
194656-75-2 (HCl) 222638-65-5 (free base)
Synonym
ABH Hydrochloride; ABH HCl; 6-borono-L-norleucine;
IUPAC/Chemical Name
2(S)-Amino-6-boronohexanoic acid hydrochloride
InChi Key
XCUVEZUCSHVMRK-JEDNCBNOSA-N
InChi Code
InChI=1S/C6H14BNO4.ClH/c8-5(6(9)10)3-1-2-4-7(11)12;/h5,11-12H,1-4,8H2,(H,9,10);1H/t5-;/m0./s1
SMILES Code
O=C(O)[C@@H](N)CCCCB(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
Certificate of Analysis
View CoA: current batch, Lot#C8M03C14
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 211.44 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
1: Golebiowski A, Paul Beckett R, Van Zandt M, Ji MK, Whitehouse D, Ryder TR, Jagdmann E, Andreoli M, Mazur A, Padmanilayam M, Cousido-Siah A, Mitschler A, Ruiz FX, Podjarny A, Schroeter H. 2-Substituted-2-amino-6-boronohexanoic acids as arginase inhibitors. Bioorg Med Chem Lett. 2013 Apr 1;23(7):2027-30. doi: 10.1016/j.bmcl.2013.02.024. Epub 2013 Feb 13. PMID: 23453840. 2: Velázquez-Libera JL, Navarro-Retamal C, Caballero J. Insights into the Structural Requirements of 2(S)-Amino-6-Boronohexanoic Acid Derivatives as Arginase I Inhibitors: 3D-QSAR, Docking, and Interaction Fingerprint Studies. Int J Mol Sci. 2018 Sep 28;19(10):2956. doi: 10.3390/ijms19102956. PMID: 30274146; PMCID: PMC6213053. 3: Tsai P, Cao GL, Tomczuk B, Suzdak PD, Cross AS, Shapiro P, Rosen GM. Effect of the mammalian arginase inhibitor 2(S)-amino-6-boronohexanoic acid on Bacillus anthracis arginase. Curr Microbiol. 2012 Apr;64(4):379-84. doi: 10.1007/s00284-012-0084-9. Epub 2012 Jan 24. PMID: 22271269. 4: Segal R, Hannan JL, Liu X, Kutlu O, Burnett AL, Champion HC, Kim JH, Steppan J, Berkowitz DE, Bivalacqua TJ. Chronic oral administration of the arginase inhibitor 2(S)-amino-6-boronohexanoic acid (ABH) improves erectile function in aged rats. J Androl. 2012 Nov-Dec;33(6):1169-75. doi: 10.2164/jandrol.111.015834. Epub 2012 Apr 5. PMID: 22492840; PMCID: PMC4029113. 5: Borek B, Gajda T, Golebiowski A, Blaszczyk R. Boronic acid-based arginase inhibitors in cancer immunotherapy. Bioorg Med Chem. 2020 Sep 15;28(18):115658. doi: 10.1016/j.bmc.2020.115658. Epub 2020 Jul 23. PMID: 32828425. 6: Oda K, Sakaguchi T, Matoba Y. Catalytic mechanism of DcsB: Arginase framework used for hydrolyzing its inhibitor. Protein Sci. 2022 Jun;31(6):e4338. doi: 10.1002/pro.4338. PMID: 35634777; PMCID: PMC9125327. 7: Golebiowski A, Whitehouse D, Beckett RP, Van Zandt M, Ji MK, Ryder TR, Jagdmann E, Andreoli M, Lee Y, Sheeler R, Conway B, Olczak J, Mazur M, Czestkowski W, Piotrowska W, Cousido-Siah A, Ruiz FX, Mitschler A, Podjarny A, Schroeter H. Synthesis of quaternary α-amino acid-based arginase inhibitors via the Ugi reaction. Bioorg Med Chem Lett. 2013 Sep 1;23(17):4837-41. doi: 10.1016/j.bmcl.2013.06.092. Epub 2013 Jul 8. PMID: 23886684. 8: Pudlo M, Demougeot C, Girard-Thernier C. Arginase Inhibitors: A Rational Approach Over One Century. Med Res Rev. 2017 May;37(3):475-513. doi: 10.1002/med.21419. Epub 2016 Nov 15. PMID: 27862081. 9: 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. PMID: 24062745; PMCID: PMC3774993. 10: Hai Y, Christianson DW. Crystal structures of Leishmania mexicana arginase complexed with α,α-disubstituted boronic amino-acid inhibitors. Acta Crystallogr F Struct Biol Commun. 2016 Apr;72(Pt 4):300-6. doi: 10.1107/S2053230X16003630. Epub 2016 Mar 16. PMID: 27050264; PMCID: PMC4822987. 11: Kim NN, Christianson DW, Traish AM. Role of arginase in the male and female sexual arousal response. J Nutr. 2004 Oct;134(10 Suppl):2873S-2879S; discussion 2895S. doi: 10.1093/jn/134.10.2873S. PMID: 15465804. 12: Blaszczyk R, Brzezinska J, Dymek B, Stanczak PS, Mazurkiewicz M, Olczak J, Nowicka J, Dzwonek K, Zagozdzon A, Golab J, Golebiowski A. Discovery and Pharmacokinetics of Sulfamides and Guanidines as Potent Human Arginase 1 Inhibitors. ACS Med Chem Lett. 2020 Mar 13;11(4):433-438. doi: 10.1021/acsmedchemlett.9b00508. PMID: 32292546; PMCID: PMC7153016. 13: Yao L, Bhatta A, Xu Z, Chen J, Toque HA, Chen Y, Xu Y, Bagi Z, Lucas R, Huo Y, Caldwell RB, Caldwell RW. Obesity-induced vascular inflammation involves elevated arginase activity. Am J Physiol Regul Integr Comp Physiol. 2017 Nov 1;313(5):R560-R571. doi: 10.1152/ajpregu.00529.2016. Epub 2017 Aug 23. PMID: 28835451; PMCID: PMC5792147. 14: Mohaissen T, Proniewski B, Targosz-Korecka M, Bar A, Kij A, Bulat K, Wajda A, Blat A, Matyjaszczyk-Gwarda K, Grosicki M, Tworzydlo A, Sternak M, Wojnar- Lason K, Rodrigues-Diez R, Kubisiak A, Briones A, Marzec KM, Chlopicki S. Temporal relationship between systemic endothelial dysfunction and alterations in erythrocyte function in a murine model of chronic heart failure. Cardiovasc Res. 2022 Sep 20;118(12):2610-2624. doi: 10.1093/cvr/cvab306. Erratum in: Cardiovasc Res. 2022 Sep 15;: PMID: 34617995; PMCID: PMC9491865. 15: Cama E, Pethe S, Boucher JL, Han S, Emig FA, Ash DE, Viola RE, Mansuy D, Christianson DW. Inhibitor coordination interactions in the binuclear manganese cluster of arginase. Biochemistry. 2004 Jul 20;43(28):8987-99. doi: 10.1021/bi0491705. PMID: 15248756. 16: van den Berg MPM, Kurhade SH, Maarsingh H, Erceg S, Hulsbeek IR, Boekema PH, Kistemaker LEM, van Faassen M, Kema IP, Elsinga PH, Dömling A, Meurs H, Gosens R. Pharmacological Screening Identifies SHK242 and SHK277 as Novel Arginase Inhibitors with Efficacy against Allergen-Induced Airway Narrowing In Vitro and In Vivo. J Pharmacol Exp Ther. 2020 Jul;374(1):62-73. doi: 10.1124/jpet.119.264341. Epub 2020 Apr 8. PMID: 32269169. 17: Di Costanzo L, Moulin M, Haertlein M, Meilleur F, Christianson DW. Expression, purification, assay, and crystal structure of perdeuterated human arginase I. Arch Biochem Biophys. 2007 Sep 1;465(1):82-9. doi: 10.1016/j.abb.2007.04.036. Epub 2007 May 21. PMID: 17562323; PMCID: PMC2018606. 18: Van Zandt MC, Jagdmann GE, Whitehouse DL, Ji M, Savoy J, Potapova O, Cousido-Siah A, Mitschler A, Howard EI, Pyle AM, Podjarny AD. Discovery of N-Substituted 3-Amino-4-(3-boronopropyl)pyrrolidine-3-carboxylic Acids as Highly Potent Third-Generation Inhibitors of Human Arginase I and II. J Med Chem. 2019 Sep 12;62(17):8164-8177. doi: 10.1021/acs.jmedchem.9b00931. Epub 2019 Aug 23. PMID: 31408339. 19: Toso A, Aránguiz O, Céspedes C, Navarrete O, Hernández C, Vio CP, Luco M, Casanello P, Kattan J. Congenital diaphragmatic hernia: phosphodiesterase-5 and Arginase inhibitors prevent pulmonary vascular hypoplasia in rat lungs. Pediatr Res. 2022 Nov 23. doi: 10.1038/s41390-022-02366-4. Epub ahead of print. PMID: 36418485. 20: Busnel O, Carreaux F, Carboni B, Pethe S, Goff SV, Mansuy D, Boucher JL. Synthesis and evaluation of new omega-borono-alpha-amino acids as rat liver arginase inhibitors. Bioorg Med Chem. 2005 Apr 1;13(7):2373-9. doi: 10.1016/j.bmc.2005.01.053. PMID: 15755639.