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Psicofuranine

Alias: Psicofuranine NSC-53104 NSC 53104
Cat No.:V6163 Purity: ≥98%
Psicofuramine is a nucleoside antibiotic that can inhibit xanthine 5'-phosphoaminase.
Psicofuranine
Psicofuranine Chemical Structure CAS No.: 1874-54-0
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
50mg
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Product Description
Psicofuramine is a nucleoside antibiotic that can inhibit xanthine 5'-phosphoaminase. Psicofuramine also specifically inhibits GMP synthase and interrupts parasite growth. Psicofuramine exerts a dose-dependent inhibitory activity against the growth of Plasmodium falciparum.
Psicofuranine (CAS#: 1874-54-0) is a nucleoside antibiotic derived from Streptomyces species. It has a molecular weight of 297.27 g/mol and a molecular formula of C11H15N5O5. Psicofuranine inhibits xanthosine monophosphate aminase, an enzyme involved in purine nucleotide synthesis. By inhibiting this enzyme, Psicofuranine blocks the synthesis of guanine nucleotides, thereby inhibiting DNA and RNA synthesis in cells. Psicofuranine shows dose-dependent inhibition of Plasmodium falciparum growth with an IC50 of 0.3 mM. It has been primarily studied for its antitumor and antiviral properties.
Biological Activity I Assay Protocols (From Reference)
Targets
Psicofuranine targets xanthosine monophosphate (XMP) aminase, also known as GMP synthetase, a key enzyme in the de novo synthesis of guanine nucleotides. XMP aminase catalyzes the conversion of XMP to GMP, a critical step in the purine nucleotide biosynthesis pathway. By inhibiting this enzyme, Psicofuranine blocks the production of GMP, leading to a depletion of guanine nucleotides. This depletion inhibits DNA and RNA synthesis, which is essential for cell proliferation. Psicofuranine's mechanism of action as a nucleoside antibiotic underlies its antitumor and antiviral activities.
ln Vitro
By isolating a pyridofuran-resistant E. coli, it was shown that pyridofuran specifically inhibits bacterial GMP synthase. coli mutant that prevents bacterial growth by carrying a mutation in the gene encoding GMP synthase. With an IC50 of 0.3 mM, psicofuranine inhibits Plasmodium falciparum development in a dose-dependent manner. Psicofuranine's inhibitory concentration is comparable to E's. Coli [1].
In vitro, Psicofuranine has been shown to inhibit the growth of various cell lines and microorganisms. It shows dose-dependent inhibition of Plasmodium falciparum growth with an IC50 of 0.3 mM. Its activity is typically measured using cell-based assays that assess cell viability, DNA synthesis, and nucleotide levels. The compound's ability to inhibit XMP aminase can be measured using enzyme assays with purified enzyme and substrates. These in vitro studies confirm Psicofuranine's mechanism of action as an inhibitor of purine nucleotide synthesis.
ln Vivo
In vivo, Psicofuranine has been studied for its antitumor and antiviral properties. As a nucleoside antibiotic that inhibits purine nucleotide synthesis, it has the potential to inhibit the growth of tumors and viruses. However, specific in vivo protocols and results are not detailed in standard product descriptions. Psicofuranine is a research compound used to study purine metabolism, antimicrobial activity, and cancer biology.
Enzyme Assay
In vitro enzyme assays for Psicofuranine measure its inhibition of xanthosine monophosphate (XMP) aminase (GMP synthetase). The enzyme is incubated with XMP, ATP, and glutamine in the presence of varying concentrations of Psicofuranine. The production of GMP is measured, and the IC50 is determined from the dose-response curve. These assays confirm the compound's mechanism of action as an inhibitor of purine nucleotide synthesis.
Cell Assay
In vitro cell-based assays for Psicofuranine are used to study its effects on cell proliferation and nucleotide metabolism. Cells are treated with Psicofuranine at various concentrations. Cell viability is assessed using assays such as MTT or CellTiter-Glo. DNA synthesis is measured by incorporation of labeled nucleotides. Nucleotide levels are measured by HPLC or LC-MS. These assays confirm the compound's antiproliferative activity and its effects on purine nucleotide synthesis.
Animal Protocol
In vivo animal experiments for Psicofuranine are not extensively described in the available literature. As a research compound, its use in vivo would be determined by the specific research question being addressed. A typical protocol for studying an antitumor compound would involve its administration to animal models of cancer. However, specific protocols for Psicofuranine are not detailed.
ADME/Pharmacokinetics
Psicofuranine has a molecular weight of 297.27 g/mol and a molecular formula of C11H15N5O5. Its IUPAC name is (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-2,5-bis(hydroxymethyl)oxolane-3,4-diol. It has a CAS number of 1874-54-0. It is a solid compound with a purity of ≥98%. For storage, it is recommended to keep the powder at -20°C. Detailed pharmacokinetic properties such as absorption, distribution, metabolism, and excretion (ADME) have not been extensively characterized. As a research compound, its stability is maintained by proper storage as a dry powder.
Toxicity/Toxicokinetics
Detailed toxicity data for Psicofuranine is not provided in standard product descriptions. As a nucleoside antibiotic that inhibits purine nucleotide synthesis, it can have significant toxicity, including myelosuppression and gastrointestinal disturbances. As with all research chemicals, standard laboratory safety precautions should be followed when handling Psicofuranine. Its use is limited to research applications and it is not intended for human or veterinary use.
References
[1]. cConkey GA. Plasmodium falciparum: isolation and characterisation of a gene encoding protozoan GMP synthase. Exp Parasitol. 2000 Jan;94(1):23-32.
[2]. UDAKA S, et al. INHIBITION OF PARENTAL AND MUTANT XANTHOSINE 5'-PHOSPHATE AMINASES BY PSICOFURANINE. J Biol Chem. 1963 Aug;238:2797-803.
Additional Infomation
Psicofuranin is a purine nucleoside and a derivative of allulose.
Psicofuranine is a research compound and is not approved for any clinical or therapeutic use. It is a nucleoside antibiotic derived from Streptomyces species. Psicofuranine inhibits xanthosine monophosphate aminase, an enzyme involved in purine nucleotide synthesis. By inhibiting this enzyme, Psicofuranine blocks the synthesis of guanine nucleotides, thereby inhibiting DNA and RNA synthesis in cells. Psicofuranine shows dose-dependent inhibition of Plasmodium falciparum growth with an IC50 of 0.3 mM. It has been primarily studied for its antitumor and antiviral properties. Psicofuranine is a valuable research tool for studying purine metabolism and antimicrobial activity.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H5N5O5
Molecular Weight
297.27
Exact Mass
297.107
CAS #
1874-54-0
PubChem CID
65086
Appearance
White to off-white solid powder
Density
2.02g/cm3
Boiling Point
720.1ºC at 760 mmHg
Flash Point
389.3ºC
Vapour Pressure
9.24E-22mmHg at 25°C
Index of Refraction
1.855
LogP
-2.2
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
3
Heavy Atom Count
21
Complexity
390
Defined Atom Stereocenter Count
4
SMILES
OCC1C(O)C(O)C(N2C=NC3=C(N=CN=C23)N)(CO)O1
InChi Key
BNZYRKVSCLSXSJ-IOSLPCCCSA-N
InChi Code
InChI=1S/C11H15N5O5/c12-9-6-10(14-3-13-9)16(4-15-6)11(2-18)8(20)7(19)5(1-17)21-11/h3-5,7-8,17-20H,1-2H2,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
Chemical Name
(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-2,5-bis(hydroxymethyl)oxolane-3,4-diol
Synonyms
Psicofuranine NSC-53104 NSC 53104
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)
DMSO : ~50 mg/mL (~168.20 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
(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 3.3639 mL 16.8197 mL 33.6395 mL
5 mM 0.6728 mL 3.3639 mL 6.7279 mL
10 mM 0.3364 mL 1.6820 mL 3.3639 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)
  • Click the “Calculate” button
  • 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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
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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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • 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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