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ABH Hydrochloride

Alias: ABH HCl 6-borono-L-norleucine ABH Hydrochloride
Cat No.:V5664 Purity: ≥98%
ABH Hydrochloride (ABH HCl)is a novel and potent arginase inhibitor with anti-anti-inflammatory activity andcan enhance both male and female sexual arousal responses.
ABH Hydrochloride
ABH Hydrochloride Chemical Structure CAS No.: 194656-75-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
50mg
Other Sizes

Other Forms of ABH Hydrochloride:

  • ABH free base
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
ABH Hydrochloride (ABH HCl) is a novel and potent arginase inhibitor with anti-anti-inflammatory activity and can enhance both male and female sexual arousal responses.
ABH Hydrochloride (CAS#: 194656-75-2), also known as 6-borono-L-norleucine hydrochloride, is a potent, orally active inhibitor of the enzyme arginase. It is a boronic acid-containing amino acid derivative that functions by chelating the binuclear manganese cluster in the active site of arginase, thereby blocking the conversion of L-arginine to L-ornithine and urea. This inhibition leads to increased levels of L-arginine, which serves as the substrate for nitric oxide synthase (NOS), promoting the production of nitric oxide (NO). ABH Hydrochloride has demonstrated anti-inflammatory activity and is being researched for its potential to enhance sexual arousal responses and treat various pathological conditions. It is a valuable research tool for studying the roles of arginase and the arginine-NO pathway in inflammation, cardiovascular disease, and other disorders.
Biological Activity I Assay Protocols (From Reference)
Targets
ABH Hydrochloride primarily targets arginase, a binuclear manganese metalloenzyme that catalyzes the hydrolysis of L-arginine to L-ornithine and urea. This enzyme is a key regulator of the arginine-NO pathway, as it competes with nitric oxide synthase (NOS) for the common substrate L-arginine. By potently inhibiting arginase with a Ki of 8.5 nM, ABH Hydrochloride shifts the balance of L-arginine metabolism towards NOS, thereby increasing nitric oxide (NO) production. NO is a critical signaling molecule involved in vasodilation, neurotransmission, and immune function. The compound's effect on this pathway underlies its diverse biological activities, including the reduction of inflammatory markers and improvement in vascular and erectile function.
ln Vitro
In vitro, ABH Hydrochloride has been shown to effectively inhibit arginase activity, leading to a significant increase in NO production in various cell types. This increase in NO is associated with a reduction in the expression of key inflammatory response-related molecules, including intercellular adhesion molecule-1 (ICAM-1), vascular cell adhesion molecule-1 (VCAM-1), and monocyte chemoattractant protein-1 (MCP-1). By modulating the expression of these adhesion molecules and chemokines, ABH Hydrochloride can attenuate the recruitment of immune cells and the subsequent inflammatory cascade. These in vitro findings establish the compound's mechanism of action and its potential as an anti-inflammatory agent.
ln Vivo
In vivo studies have demonstrated that ABH Hydrochloride exerts significant therapeutic effects in various animal models. Orally administered ABH Hydrochloride has been shown to improve erectile function, reduce lung damage, promote wound healing, reduce arterial blood pressure, and improve vascular fibrosis. These effects are attributed to its ability to increase NO production and reduce inflammation. For instance, in models of pulmonary hypertension or fibrosis, the compound's ability to lower blood pressure and reduce tissue damage highlights its therapeutic potential in cardiovascular and inflammatory diseases. The compound is reported to be well-tolerated and effective when administered orally.
Enzyme Assay
In vitro enzyme activity assays for ABH Hydrochloride typically measure its inhibition of arginase. A common protocol involves incubating the enzyme with its substrate, L-arginine, and varying concentrations of the compound. The amount of urea produced, which is a direct product of the enzymatic reaction, is then quantified using a colorimetric assay, such as the Chinard method. The inhibition constant (Ki) is determined from the dose-response curve. For ABH Hydrochloride, this assay has established a Ki of 8.5 nM, confirming its high potency as an arginase inhibitor. The compound's boron-containing structure allows it to form a tight, reversible complex with the enzyme's active site.
Cell Assay
In vitro cell-based assays for ABH Hydrochloride are used to study its effects on NO production and inflammation in living cells. Typically, endothelial cells, macrophages, or other relevant cell types are cultured and treated with the compound. Nitric oxide (NO) production is measured indirectly by quantifying the accumulation of its stable metabolites, nitrite and nitrate, in the culture medium using the Griess reaction. The expression of inflammatory markers like ICAM-1, VCAM-1, and MCP-1 is assessed via techniques such as quantitative real-time PCR (qRT-PCR) or ELISA. These assays confirm that arginase inhibition by ABH Hydrochloride leads to increased NO and decreased inflammation at the cellular level.
Animal Protocol
In vivo animal experiments for ABH Hydrochloride are conducted in various disease models to evaluate its therapeutic potential. In a typical study, the compound is administered orally to animals. For example, in a model of erectile dysfunction, the compound's ability to improve erectile function is measured. In a model of lung injury, researchers assess the reduction in lung damage. Arterial blood pressure is monitored in hypertensive models to evaluate its vasodilatory effects. Wound healing is assessed by measuring the rate of wound closure. These experiments provide critical evidence for the compound's in vivo efficacy and support its development as a therapeutic agent for a range of conditions.
ADME/Pharmacokinetics
ABH Hydrochloride is characterized as an orally active compound, suggesting good bioavailability after oral administration. It has a molecular weight of 211.45 g/mol and a molecular formula of C6H15BClNO4. As a small molecule, it is expected to be distributed throughout the body. The compound is typically stored as a powder at -20°C for long-term stability. While a detailed pharmacokinetic profile is not fully described in the provided search results, its oral activity and potent in vivo effects indicate that it is well-absorbed and reaches its target tissues in sufficient concentrations to exert its pharmacological effects.
Toxicity/Toxicokinetics
ABH Hydrochloride is a research compound and is not approved for clinical use. Its toxicity profile has not been extensively detailed, but it has been used in various animal studies without reported overt toxicity at therapeutic doses. As a potent enzyme inhibitor, its primary effects are expected to be on-target, related to increased NO production and reduced inflammation. The compound should be handled with standard laboratory safety precautions, including the use of appropriate personal protective equipment (PPE). It is intended for research use only and is not for human or veterinary therapeutic applications.
References

[1]. Improved and high yield synthesis of the potent arginase inhibitor: 2 (S)-amino-6-boronohexanoic acid. Organic process research & development, 2005, 9(5): 677-679.

Additional Infomation
ABH Hydrochloride is a potent and selective arginase inhibitor with significant potential for studying and treating a wide range of diseases. By inhibiting arginase and increasing NO production, it has shown promise in models of inflammation, cardiovascular disease, and wound healing. Its mechanism of action makes it a valuable tool for studying the arginine-NO pathway and its role in various pathophysiological processes. The compound is not currently approved for clinical use, and its development is primarily focused on research applications. Further studies are needed to fully elucidate its safety and efficacy for potential therapeutic use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H15BCLNO4
Molecular Weight
211.44
Exact Mass
211.078
CAS #
194656-75-2
Related CAS #
194656-75-2 (HCl);222638-65-5;
PubChem CID
10104590
Appearance
White to off-white solid powder
LogP
0.543
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
6
Heavy Atom Count
13
Complexity
142
Defined Atom Stereocenter Count
1
SMILES
B(CCCC[C@@H](C(=O)O)N)(O)O.Cl
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
Chemical Name
(2S)-2-amino-6-boronohexanoic acid;hydrochloride
Synonyms
ABH HCl 6-borono-L-norleucine ABH Hydrochloride
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~31.25 mg/mL (~147.79 mM)
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.7295 mL 23.6474 mL 47.2947 mL
5 mM 0.9459 mL 4.7295 mL 9.4589 mL
10 mM 0.4729 mL 2.3647 mL 4.7295 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT01556932 COMPLETEDWITH RESULTS Drug: ABH gel
Other: placebo
Nausea
Vomiting
Virginia Commonwealth University 2012-03 Not Applicable
NCT01204255 COMPLETEDWITH RESULTS Drug: lorazepam
Drug: diphenhydramine hydrochloride
Drug: haloperidol
Healthy Virginia Commonwealth University 2010-11-15 Not Applicable
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