| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
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| Other Sizes |
| Targets |
2-Iminobiotin is a competitive inhibitor of nitric oxide synthase (NOS) isoforms.
Murine inducible NOS (iNOS): Ki = 21.8 ± 2.9 μM. Rat neuronal constitutive NOS (n-cNOS): Ki = 37.5 ± 1.7 μM. [1] |
|---|---|
| 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].
2-Iminobiotin reversibly inhibits both murine iNOS and rat n-cNOS in a concentration-dependent manner, as measured by L-citrulline formation from L-arginine. Inhibition is fully protected by saturating concentrations of substrate L-Arg, indicating competitive binding at or near the L-Arg binding site. The compound does not serve as an alternate substrate for NOS, as no nitrite production was detected after incubation with iNOS. 2-Iminobiotin does not inhibit the diaphorase activity of iNOS or n-cNOS. Biotin, 2-thiobiotin, diaminobiotin, and desthiobiotin do not inhibit NOS even at 500 μM, indicating the guanidino group is essential for inhibitory activity. Carboxy derivatives of 2-iminobiotin (e.g., hydrazide, N-hydroxysuccinimide ester) also inhibit iNOS, suggesting the free carboxyl group is not required for binding. [1] |
| Enzyme Assay |
NOS activity was measured using two methods: (1) a colorimetric Griess assay to detect nitrite formation, and (2) a radiometric HPLC assay to monitor conversion of L-[³H]Arg to L-[³H]Cit.
For the radiometric assay, incubations contained partially purified NOS, cofactors (FAD, FMN, BH₄, NADPH, DTT), and L-[³H]Arg in TES buffer at pH 7.5. Reactions were quenched with citrate buffer and analyzed by HPLC. Inhibition studies involved preincubating enzyme with inhibitor before adding substrate, or adding inhibitor directly to the assay mixture. Kinetic parameters (Ki) were determined using Dixon plots from initial velocity data at substrate concentrations below Km. Time-dependent inhibition was assessed by fitting progress curves to a first-order exponential decay model. [1] |
| References | |
| Additional Infomation |
Drug Indication
Treatment of perinatal asphyxia 2-Iminobiotin shares structural similarities with L-arginine, both containing a guanidine group, which may enable it to competitively bind to the active site of NOS. Its bicyclic structure can serve as a template for designing more effective and selective NOS inhibitors. 2-Iminobiotin immobilized on agarose has been tested as an affinity resin for NOS purification, but initial attempts were unsuccessful. This compound is known to be used as an affinity reagent for avidin purification. [1] |
| Molecular Formula |
C10H17N3O2S
|
|---|---|
| Molecular Weight |
243.32588
|
| Exact Mass |
243.104
|
| CAS # |
13395-35-2
|
| Related CAS # |
2-Iminobiotin hydrobromide;76985-52-9
|
| PubChem CID |
128878
|
| Appearance |
White to off-white solid powder
|
| Density |
1.6±0.1 g/cm3
|
| Boiling Point |
477.3±55.0 °C at 760 mmHg
|
| Flash Point |
242.5±31.5 °C
|
| Vapour Pressure |
0.0±2.6 mmHg at 25°C
|
| Index of Refraction |
1.737
|
| LogP |
-0.36
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
5
|
| Heavy Atom Count |
16
|
| Complexity |
308
|
| Defined Atom Stereocenter Count |
3
|
| SMILES |
C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)O)N=C(N2)N
|
| InChi Key |
WWVANQJRLPIHNS-ZKWXMUAHSA-N
|
| InChi Code |
InChI=1S/C10H17N3O2S/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)/t6-,7-,9-/m0/s1
|
| Chemical Name |
5-[(3aS,4S,6aR)-2-amino-3a,4,6,6a-tetrahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid
|
| 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 |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~12.5 mg/mL (~51.37 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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 : PEG300 ：Tween 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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.1096 mL | 20.5482 mL | 41.0965 mL | |
| 5 mM | 0.8219 mL | 4.1096 mL | 8.2193 mL | |
| 10 mM | 0.4110 mL | 2.0548 mL | 4.1096 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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