| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| 100mg |
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| 250mg | |||
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| Targets |
2-Iminobiotin hydrobromide targets two distinct classes of proteins. First, it binds with high affinity to avidin and streptavidin through the biotin-binding pocket. Second, it acts as a reversible inhibitor of inducible nitric oxide synthase (iNOS) and neuronal nitric oxide synthase (nNOS). The Ki values are 21.8 μM for murine iNOS and 37.5 μM for rat n-cNOS. It does not significantly inhibit endothelial NOS (eNOS), suggesting some isoform selectivity.
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| ln Vitro |
Lactate dehydrogenase (LDH) levels rise in response to hypoxia; however, this effect is reversed when low concentrations of 2-iminobiotin (2-IB; 10 ng/mL and 30 ng/mL) are applied on top of hypothermia. No distinction[1].
In vitro, 2-iminobiotin hydrobromide demonstrates reversible inhibition of nitric oxide synthases. The compound inhibits murine iNOS with a Ki of 21.8 μM and rat n-cNOS with a Ki of 37.5 μM. It also exhibits pH-dependent binding to avidin and streptavidin, making it valuable for affinity purification applications where gentle elution is required. Additionally, 2-iminobiotin has been shown to protect human neuronal cells from hypoxia-induced cell damage when combined with hypothermia. |
| ln Vivo |
In vivo, 2-iminobiotin hydrobromide has been studied for its neuroprotective properties. At a dose of 0.2 mg/kg, it has been evaluated in models of hypoxia-induced neuronal damage. The compound's ability to inhibit nNOS suggests potential applications in conditions involving excitotoxicity and ischemic injury. Its pH-dependent binding properties may also be exploited for in vivo applications requiring reversible biotin-streptavidin interactions.
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| Enzyme Assay |
Non-cellular enzyme/receptor binding assay protocols for 2-iminobiotin hydrobromide involve measuring NOS inhibition using the conversion of [³H]arginine to [³H]citrulline. The enzyme is incubated with various concentrations of the inhibitor, and the IC50 or Ki values are determined. For avidin binding studies, fluorescence-based or surface plasmon resonance (SPR) assays can be used to measure binding affinity at different pH conditions. The pH-dependent dissociation can be monitored by changes in fluorescence or absorbance.
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| Cell Assay |
Cellular assay protocols for 2-iminobiotin hydrobromide typically involve treating neuronal cell cultures under hypoxic conditions. Cells are exposed to the compound at various concentrations, and cell viability is assessed using MTT or LDH release assays. NOS activity in cell lysates can be measured by the conversion of arginine to citrulline. For biotin-avidin based applications, cells can be labeled with 2-iminobiotin-conjugated probes and detected using streptavidin-linked reporters under appropriate pH conditions.
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| Animal Protocol |
In vivo animal experiment protocols for 2-iminobiotin hydrobromide involve administering the compound to rodents via parenteral routes. Doses such as 0.2 mg/kg have been used in hypoxia models. Endpoints include measurement of NOS activity in tissues, assessment of neuronal damage, and evaluation of neuroprotective effects. Tissue samples are collected for biochemical analysis. Pharmacodynamic markers such as nitrite/nitrate levels may be measured to assess NOS inhibition in vivo.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 2-iminobiotin hydrobromide have not been extensively characterized. As a small molecule (MW 324.24 g/mol), it is expected to have reasonable oral bioavailability, though the compound is typically administered parenterally in research studies. The hydrobromide salt form enhances aqueous solubility. The compound's pH-dependent binding to proteins may affect its distribution and elimination. Further PK studies would be needed to fully characterize its absorption, distribution, metabolism, and excretion profile.
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| Toxicity/Toxicokinetics |
The toxicity profile of 2-iminobiotin hydrobromide has not been extensively reported. As a biotin analog, it is expected to have low inherent toxicity. However, its NOS inhibitory activity suggests potential effects on nitric oxide signaling pathways that could have physiological consequences. Standard toxicological evaluation would include acute toxicity studies in rodents, as well as assessments of cardiovascular, neurological, and reproductive effects. The compound is for research use only and not intended for human therapeutic applications.
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| References | |
| Additional Infomation |
2-Iminobiotin hydrobromide (CAS: 76985-52-9) has a molecular formula of C10H18BrN3O2S and a molecular weight of 324.24 g/mol. It is also known as Guanidinobiotin hydrobromide. The compound is a biotin analog that binds reversibly to avidin and streptavidin under pH-dependent conditions, making it useful for affinity purification applications requiring gentle elution of biomolecules. It is also a reversible inhibitor of iNOS and nNOS. The product is for research use only.
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| Molecular Formula |
C10H18BRN3O2S
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|---|---|
| Molecular Weight |
324.237820148468
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| Exact Mass |
323.03
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| CAS # |
76985-52-9
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| Related CAS # |
2-Iminobiotin;13395-35-2
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| PubChem CID |
131667834
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| Appearance |
White to off-white solid powder
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
17
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| Complexity |
308
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| Defined Atom Stereocenter Count |
3
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| SMILES |
Br.S1C[C@H]2[C@@H]([C@@H]1CCCCC(=O)O)N=C(N)N2
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| InChi Key |
JKIJLCYOCQWMQL-UFLZEWODSA-N
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| InChi Code |
InChI=1S/C10H17N3O2S.BrH/c11-10-12-6-5-16-7(9(6)13-10)3-1-2-4-8(14)15;/h6-7,9H,1-5H2,(H,14,15)(H3,11,12,13);1H/t6-,7-,9-;/m0./s1
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| Chemical Name |
5-[(3aS,4S,6aR)-2-amino-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid;hydrobromide
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| Synonyms |
2Iminobiotin hydrobromide; 2 Iminobiotin hydrobromide
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~125 mg/mL (~385.52 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.42 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (6.42 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (6.42 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0841 mL | 15.4207 mL | 30.8414 mL | |
| 5 mM | 0.6168 mL | 3.0841 mL | 6.1683 mL | |
| 10 mM | 0.3084 mL | 1.5421 mL | 3.0841 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.
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.
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