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2',3'-cUMP sodium

Alias: Uridine-2', 3'-cyclic monophosphate sodium salt
Cat No.:V91091 Purity: ≥98%
2',3'-cUMP sodium (Uridine-2', 3'-cyclic monophosphate sodium salt) is a competitive inhibitor of di-p-nitrophenyl phosphate hydrolysis.
2',3'-cUMP sodium
2',3'-cUMP sodium Chemical Structure CAS No.: 15718-50-0
Product category: Microorganisms
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
Other Sizes

Other Forms of 2',3'-cUMP sodium:

  • 2',3'-Cyclic UMP
Official Supplier of:
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Product Description
2',3'-cUMP sodium (Uridine-2', 3'-cyclic monophosphate sodium salt) is a competitive inhibitor of di-p-nitrophenyl phosphate hydrolysis.
2',3'-cUMP sodium (Uridine-2',3'-cyclic monophosphate sodium salt; CAS: 15718-50-0; C9H10N2NaO8P, MW 328.15) is a cyclic nucleotide analog. It is a transition-state analog of RNA hydrolysis by ribonuclease A (RNase A), acting as a competitive inhibitor of the enzyme. It is used as a research tool in the study of RNA degradation mechanisms and as a specific inhibitor in biochemical assays. The compound shows promise in biomedical research for the treatment of various ailments, including cancer and viral infections, though it is not an approved drug.
Biological Activity I Assay Protocols (From Reference)
Targets
2',3'-cUMP sodium acts as a competitive inhibitor of ribonuclease A (RNase A). By binding to the active site of the enzyme, it prevents the enzyme from binding to and cleaving RNA. Specifically, it is a transition-state analog, meaning it mimics the geometry and charge of the RNA molecule as it is being hydrolyzed, leading to tight binding to the enzyme's active site. It is also a competitive inhibitor of di-p-nitrophenyl phosphate hydrolysis.
ln Vitro
In vitro, 2',3'-cUMP is used in enzyme kinetics assays to inhibit the activity of RNase A. The inhibition constant (Ki) can be determined by measuring the enzyme's activity in the presence of varying concentrations of the inhibitor. It is also used to study the mechanism of RNA hydrolysis by providing a stable analog of the transition state. Its activity is not typically evaluated on whole cells, as it is a nucleotide analog that may have multiple effects.
ln Vivo
No specific in vivo activity data is reported. As a nucleotide analog, it could potentially interfere with cellular nucleic acid metabolism if administered in vivo. It shows promise in research for the treatment of cancer and viral infections, but this is at the stage of in vitro research only. No approved or widely studied in vivo animal models are documented for this compound.
Enzyme Assay
The standard assay for RNase A is performed in a 96-well plate. The reaction mixture (100 uL) contains 50 mM Tris-HCl (pH 7.5), 0.1 mg/mL BSA, and a fluorogenic RNA substrate (e.g., 0.5 uM of an RNAseAlert Substrate). 2',3'-cUMP is added at varying concentrations (0-1 mM). The reaction is initiated by adding 0.1-1 nM of RNase A. The increase in fluorescence (e.g., Ex/Em 490/520 nm) is measured over 15-60 minutes to determine the initial reaction rate. The Ki is calculated by fitting the data to a competitive inhibition model.
Cell Assay
2',3'-cUMP is a cell-permeable nucleotide analog, but it is not typically used in standard cell-based viability assays. For research, it could be added to the culture media of cancer cells at concentrations of 10-100 uM. After 24-72 hours, the effect on cell growth would be measured by MTT assay. However, its effect may be indirect, through inhibition of cellular RNases, and such uses are not standard. It can also be used as a standard in HPLC to quantify cyclic nucleotides in biological extracts.
Animal Protocol
No standard in vivo protocols exist for 2',3'-cUMP. As a potential anti-cancer lead, a xenograft mouse model could be used. The compound would be formulated in PBS and administered intraperitoneally or intravenously at a dose of 10-50 mg/kg. Tumor volume would be measured over 2-4 weeks, but such data is not available for this compound.
ADME/Pharmacokinetics
No specific pharmacokinetic data is available for 2',3'-cUMP sodium. As a sodium salt, it is water-soluble and soluble in DMSO. The compound is a cyclic phosphate, which is more stable than linear phosphates but can still be hydrolyzed by phosphodiesterases. For research, the compound is stored as a powder at -20degC, and solutions are prepared fresh in water or buffer. Its stability in plasma is unknown.
Toxicity/Toxicokinetics
No specific toxicology data is available. As a modified nucleotide, it is not expected to be highly toxic, but standard laboratory safety precautions should be followed. The compound may be a skin, eye, and respiratory tract irritant. Avoid inhalation, ingestion, and skin contact. It is strictly for research use only and not for human or veterinary use.
References

[1]. Kinetic studies on the cyclic phosphodiesterase with 3' nucleotidase activity from Proteus mirabilis. Arch Biochem Biophys. 1968 Sep 20;127(1):391-7.

Additional Infomation
2',3'-cUMP sodium is a cyclic nucleotide analog used as a research tool to study the mechanism of RNA hydrolysis. It is a transition-state analog and competitive inhibitor of RNase A. The compound has potential research applications in cancer and virology but is not a drug and has no approved therapeutic use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H10N2NAO8P
Molecular Weight
328.15
Exact Mass
328.007
CAS #
15718-50-0
Related CAS #
606-02-0 (Parent)
PubChem CID
44755149
Appearance
Typically exists as solid at room temperature
Density
1.85 g/cm3
Index of Refraction
1.65
Source
Originated from microorganisms: Proteus mirabilis
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
2
Heavy Atom Count
21
Complexity
542
Defined Atom Stereocenter Count
4
SMILES
C1=CN(C(=O)NC1=O)[C@H]2[C@H]3[C@@H]([C@H](O2)CO)OP(=O)(O3)[O-].[Na+]
InChi Key
LXUDDBXIXSYSRT-IAIGYFSYSA-M
InChi Code
InChI=1S/C9H11N2O8P.Na/c12-3-4-6-7(19-20(15,16)18-6)8(17-4)11-2-1-5(13)10-9(11)14;/h1-2,4,6-8,12H,3H2,(H,15,16)(H,10,13,14);/q;+1/p-1/t4-,6-,7-,8-;/m1./s1
Chemical Name
sodium;1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-oxido-2-oxo-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxaphosphol-4-yl]pyrimidine-2,4-dione
Synonyms
Uridine-2', 3'-cyclic monophosphate sodium salt
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 : 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).
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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 : PEG300:Tween 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 3.0474 mL 15.2369 mL 30.4739 mL
5 mM 0.6095 mL 3.0474 mL 6.0948 mL
10 mM 0.3047 mL 1.5237 mL 3.0474 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:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • 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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