N2C1%3dO)C)CBr)CBr)
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| 10mg |
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| 25mg |
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| 100mg |
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Dibromobimane, fluorescent imaging agent
Dibromobimane (bBBr) (CAS#: 68654-25-1) is a thiol-reactive fluorogenic crosslinking reagent for proteins. It has a molecular formula of C10H10Br2N2O2 and a molecular weight of 350.01. Dibromobimane is a pyrazolopyrazole compound composed of 1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione with two methyl groups at positions 2 and 6, and two bromomethyl groups at positions 3 and 5. It is used to crosslink cysteine- and homocysteine-containing peptides.
| Targets |
Dibromobimane targets thiol groups (cysteine residues) in proteins and peptides. As a fluorogenic crosslinking reagent, it reacts with thiol groups to form fluorescent adducts. The compound is unlikely to fluoresce until both of its alkylating groups have reacted with thiols, providing a mechanism for detecting thiol-containing proteins and peptides.
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| ln Vitro |
In vitro, dibromobimane is used as a thiol-selective fluorescent imaging agent and crosslinking reagent. It crosslinks cysteine- and homocysteine-containing peptides. Its fluorescence is activated upon reaction with thiol groups. Its activity is concentration-dependent, with effective concentrations typically in the micromolar range. Its thiol reactivity and fluorogenic properties make it a valuable tool for studying protein structure and thiol-containing biomolecules.
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| ln Vivo |
In vivo, dibromobimane is not used as a therapeutic agent but as a research tool for protein labeling and imaging. Its in vivo applications are limited to research settings.
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| Enzyme Assay |
The in vitro thiol labeling assay for dibromobimane typically involves incubating the compound with proteins or peptides containing free thiol groups. The reaction is performed in buffer at pH 7-8 for 30-60 minutes at room temperature. The formation of fluorescent adducts is detected by fluorescence spectroscopy or gel electrophoresis.
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| Cell Assay |
For in vitro cellular assays, cells are treated with dibromobimane at concentrations ranging from 1 to 100 µM for 1-24 hours. Thiol-containing proteins are labeled and detected by fluorescence microscopy or flow cytometry. Cell viability is assessed using MTT or CellTiter-Glo assays. All experiments include appropriate controls and are performed in triplicate.
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| Animal Protocol |
For in vivo studies, dibromobimane is not typically administered to animals as a therapeutic agent. It may be used in ex vivo studies on tissue samples for protein labeling.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of dibromobimane are not relevant, as it is a fluorescent probe rather than a therapeutic agent. The compound has a molecular weight of 350.01. It is used in vitro for thiol labeling.
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| Toxicity/Toxicokinetics |
The toxicology of dibromobimane is primarily related to its use as a fluorescent probe. At the low concentrations used for labeling, it is generally considered non-toxic to cells.
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| References | |
| Additional Infomation |
Dibromobimane is a pyrazolopyrazole compound composed of 1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione, with two methyl groups attached to positions 2 and 6, and two bromomethyl groups attached to positions 3 and 5. It is a fluorescent dye. It is an organobromine compound and also a pyrazolopyrazole compound.
Dibromobimane (bBBr) is a thiol-reactive fluorogenic crosslinking reagent for proteins. It has a molecular formula of C10H10Br2N2O2 and a molecular weight of 350.01. It is used to crosslink cysteine- and homocysteine-containing peptides. It is not approved for human use and is intended for research purposes only. |
| Molecular Formula |
C10H10BR2N2O2
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| Molecular Weight |
350.01
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| Exact Mass |
349.909
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| PubChem CID |
125708
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| Appearance |
White to light yellow solid powder
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| Hydrogen Bond Donor Count |
0
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
16
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| Complexity |
414
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC1=C(N2C(=C(C(=O)N2C1=O)C)CBr)CBr
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| InChi Key |
OSIYFMVMZXJKSP-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H10Br2N2O2/c1-5-7(3-11)13-8(4-12)6(2)10(16)14(13)9(5)15/h3-4H2,1-2H3
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| Chemical Name |
1,7-bis(bromomethyl)-2,6-dimethylpyrazolo[1,2-a]pyrazole-3,5-dione
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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 |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| 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 | 2.8571 mL | 14.2853 mL | 28.5706 mL | |
| 5 mM | 0.5714 mL | 2.8571 mL | 5.7141 mL | |
| 10 mM | 0.2857 mL | 1.4285 mL | 2.8571 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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