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5-Bromouridine (5-bromo-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H )-diketone)

Cat No.:V55283 Purity: ≥98%
5-Bromouridine is an analogue of purine nucleoside.
5-Bromouridine (5-bromo-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H )-diketone)
5-Bromouridine (5-bromo-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H )-diketone) Chemical Structure CAS No.: 957-75-5
Product category: Nucleoside Antimetabolite/Analog
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
Other Sizes
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Product Description
5-Bromouridine is an analogue of purine nucleoside. Purine nucleoside analogues have broad-spectrum anticancer effect targeting indolent lymphoid malignancies. The anti-cancer mechanism in this process relies on inhibiting DNA synthesis and inducing apoptosis.
5-Bromouridine is a brominated analog of the nucleoside uridine that can be incorporated into RNA and subsequently detected by antibodies against bromodeoxyuridine. It is a purine nucleoside analog with broad antitumor activity that induces apoptosis in cancer cells by inhibiting DNA synthesis. It possesses anti-viral activity and inhibits viruses such as human immunodeficiency virus. It induces apoptosis and halts the cell cycle at the S phase in HL-60 cells (LC50 = 10 μM). It is photoreactive and used for cross-linking RNA. It is a research-grade compound not approved for human therapeutic use.
Biological Activity I Assay Protocols (From Reference)
Targets
DNA synthesis; RNA metabolism; viral reverse transcriptase. 5-Bromouridine is a purine nucleoside analog that inhibits DNA synthesis and induces apoptosis. It is incorporated into RNA and can be detected by antibodies. It possesses anti-viral activity and inhibits HIV. The compound is photoreactive and can cross-link RNA upon UV irradiation.
ln Vitro
5-Bromouridine demonstrates activity as a purine nucleoside analog in cellular assays. It induces apoptosis and halts the cell cycle at the S phase in HL-60 cells with an LC50 of 10 μM. It shows activity against MOLT-4 cells with an LC50 of 20 μM. It has broad antitumor activity and antiviral activity against HIV.
ln Vivo
5-Bromouridine possesses anti-viral activity and inhibits viruses such as human immunodeficiency virus. It induces apoptosis in cancer cells by inhibiting DNA synthesis. The compound is used as a marker for DNA and RNA, where the molecule is labeled with a radioisotope or pigment after being introduced into a DNA or RNA strand.
Enzyme Assay
In vitro assays for 5-Bromouridine involve measuring inhibition of DNA synthesis using radiolabeled thymidine incorporation. For RNA incorporation studies, cells are treated with the compound and RNA is extracted for detection using anti-bromodeoxyuridine antibodies. Cell viability is assessed by MTT assays. Apoptosis is evaluated by caspase activation or flow cytometry.
Cell Assay
Cells (e.g., HL-60, MOLT-4, or other cancer cell lines) are cultured and treated with 5-Bromouridine at concentrations typically ranging from 1–100 μM for 24–72 hours. DNA/RNA synthesis inhibition is measured by BrdU incorporation or nucleotide analog detection. Cell cycle analysis is performed by flow cytometry. Apoptosis is evaluated by standard assays. For photo-crosslinking, cells are exposed to UV light after treatment.
Animal Protocol
In vivo animal studies for 5-Bromouridine have not been extensively reported. The compound is primarily used as an in vitro research tool for RNA labeling and tracking. Its antiviral activity suggests potential for in vivo studies in viral infection models.
ADME/Pharmacokinetics
Pharmacokinetic data for 5-Bromouridine have not been published. The compound has a molecular weight of 323.10 and formula C9H11BrN2O6. As a nucleoside analog, it is expected to be taken up by cells via nucleoside transporters. In vivo PK parameters have not been characterized.
Toxicity/Toxicokinetics
Toxicology data for 5-Bromouridine have not been published. The compound is for research use only and not approved for human therapeutic applications. No systematic toxicological evaluation has been performed. Standard safety precautions for handling brominated compounds should be observed.
References

[1]. Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88.

Additional Infomation
5-Bromouridine is a uridine with a bromine substituent at the 5-position. It acts as a mutagen.
5-Bromouridine (CAS: 957-75-5, molecular formula C9H11BrN2O6, molecular weight 323.10) is a brominated uridine analog. It is incorporated into RNA and detected by antibodies. It induces apoptosis in HL-60 cells (LC50 = 10 μM). It has antiviral activity against HIV. It is photoreactive and used for RNA cross-linking. It is not in clinical trials.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H11BRN2O6
Molecular Weight
323.10
Exact Mass
321.98
CAS #
957-75-5
PubChem CID
91494
Appearance
White to off-white solid powder
Density
2.0±0.1 g/cm3
Melting Point
180-182 °C (dec.)(lit.)
Index of Refraction
1.691
LogP
-0.92
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
2
Heavy Atom Count
18
Complexity
414
Defined Atom Stereocenter Count
4
SMILES
C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)Br
InChi Key
AGFIRQJZCNVMCW-UAKXSSHOSA-N
InChi Code
InChI=1S/C9H11BrN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1
Chemical Name
5-bromo-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
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 Data
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
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 3.0950 mL 15.4751 mL 30.9502 mL
5 mM 0.6190 mL 3.0950 mL 6.1900 mL
10 mM 0.3095 mL 1.5475 mL 3.0950 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

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • 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

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

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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  • 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.

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