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6-Formylpterin

Cat No.:V52482 Purity: ≥98%
6-Formylpterin is an inhibitor (blocker/antagonist) of Xanthine Oxidase.
6-Formylpterin
6-Formylpterin Chemical Structure CAS No.: 712-30-1
Product category: Apoptosis
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
6-Formylpterin is an inhibitor (blocker/antagonist) of Xanthine Oxidase. 6-Formylpterin induces ROS production and apoptosis in HL-60 cells. 6-Formylpterin inhibits PanC-1 cell proliferation/growth.
6-Formylpterin (CAS 712-30-1), also known as 6-FP or Pterin-6-aldehyde, is a xanthine oxidase inhibitor that induces ROS generation and apoptosis in HL-60 cells and inhibits PanC-1 cell proliferation. It is a Vitamin B9 (folate) metabolite and a ligand to MHC class I-related protein 1 (MR1) antigens presented on mucosal-associated invariant T (MAIT) cells.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary targets of 6-Formylpterin include xanthine oxidase (XO), reactive oxygen species (ROS) generation, and apoptosis pathways. It is an EC 1.17.3.2 (xanthine oxidase) inhibitor and a reactive oxygen species generator. It binds to one of two active sites on XO nearly quantitatively and irreversibly, preventing the metabolism of other substrates at the second site. The compound induces apoptosis in HL-60 cells and inhibits PanC-1 cell proliferation.
ln Vitro
6-Formylpterin (2 mM) causes HL-60 cells to create ROS [1]. 6- Formylpterin (0.5, 1, and 2 mM, 3 hours) causes HL-60 and Jurkat cells to have higher 2O2 concentration, which causes apoptosis [1].
In vitro, 6-Formylpterin (2 mM) produces ROS in HL-60 cells. It (0.5, 1, and 2 mM, 3 hours) increases H2O2 content in HL-60 and Jurkat cells, leading to apoptosis. The compound induces apoptosis in HL-60 cells and inhibits Fas-mediated apoptosis in Jurkat cells at 0.5 mM. It also inhibits PanC-1 cell proliferation. The compound demonstrates concentration-dependent effects on ROS generation and apoptosis.
ln Vivo
In vivo activity of 6-Formylpterin has not been extensively characterized. As a xanthine oxidase inhibitor and folate metabolite, it has potential for studying purine metabolism and immune cell function. However, detailed in vivo pharmacokinetic and pharmacodynamic studies are limited. The compound is primarily studied for its in vitro activities.
Enzyme Assay
In vitro enzyme/receptor binding assays for 6-Formylpterin typically involve xanthine oxidase inhibition studies. The enzyme is incubated with varying concentrations of the compound (0.1-100 µM) in appropriate buffer at 37°C. Xanthine oxidase activity is measured by monitoring the conversion of xanthine to uric acid using spectrophotometric methods. The compound demonstrates concentration-dependent inhibition of xanthine oxidase activity.
Cell Assay
Apoptosis Analysis[1]
Cell Types: HL-60 cells, Jurkat cells
Tested Concentrations: 0.5, 1, and 2 mM
Incubation Duration: 3 h
Experimental Results: Induced apoptosis in HL-60 cells[1]. Inhibited Fas-mediated apoptosis in Jurkat cells in 0.5 mM[1].
In vitro cellular assays for 6-Formylpterin involve testing its effects on ROS generation and apoptosis. HL-60 and Jurkat cells are treated with varying concentrations of 6-Formylpterin (0.5, 1, and 2 mM) for 3 hours. ROS production is measured using fluorescent probes such as DCFH-DA. Apoptosis is assessed by Annexin V/PI staining and caspase activity assays. The compound demonstrates concentration-dependent induction of ROS and apoptosis.
Animal Protocol
In vivo animal studies for 6-Formylpterin are limited, as the compound is primarily studied in vitro. For efficacy testing, animal models of disease could be used. Animals would be treated with 6-Formylpterin via oral or intraperitoneal administration at various doses, and relevant biomarkers would be assessed. However, detailed in vivo protocols are not well established in the available literature.
ADME/Pharmacokinetics
6-Formylpterin has a molecular formula of C7H5N5O2 and a molecular weight of 191.15. It appears as a solid with a purity of ≥95%. It is soluble in water at 33.33 mg/mL (174.37 mM) with pH adjustment to 12 with 1 M NaOH. The compound is sparingly soluble in DMSO. It should be stored at -20°C, protected from light, and stored under nitrogen. In solvent, it is stable at -80°C for 6 months and at -20°C for 1 month (protected from light, stored under nitrogen). It is intended for research use only and is not for human consumption.
Toxicity/Toxicokinetics
The toxicity profile of 6-Formylpterin has not been extensively characterized. As a folate metabolite and xanthine oxidase inhibitor, it is generally considered to have low toxicity. Standard toxicity studies would include assessment of acute oral toxicity, repeated-dose toxicity, and genotoxicity in animal models. The compound is intended for research use only and is not approved for clinical use.
References

[1]. 6-formylpterin, a xanthine oxidase inhibitor, intracellularly generates reactive oxygen species involved in apoptosis and cell proliferation. Free Radic Biol Med. 2001 Feb 1;30(3):248-59.

Additional Infomation
6-Formylpterin is a pterin with a formyl group at the 6-position. It is an inhibitor of xanthine oxidase (EC 1.17.3.2) and a reactive oxygen species generator. It belongs to the pterin class of compounds and is also an aldehyde compound.
6-Formylpterin (CAS 712-30-1) is a xanthine oxidase inhibitor that induces ROS generation and apoptosis. It has a molecular formula of C7H5N5O2 and a molecular weight of 191.15. It is a Vitamin B9 (folate) metabolite and a ligand to MR1 antigens presented on MAIT cells. The compound inhibits xanthine oxidase and induces apoptosis in HL-60 cells. It is intended for research use only and is not approved for clinical use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C7H5N5O2
Molecular Weight
191.15
Exact Mass
191.044
CAS #
712-30-1
PubChem CID
135409352
Appearance
Light yellow to brown solid powder
Density
1.9±0.1 g/cm3
Boiling Point
489.1ºC at 760 mmHg
Flash Point
249.6ºC
Index of Refraction
1.893
LogP
-1.77
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
1
Heavy Atom Count
14
Complexity
303
Defined Atom Stereocenter Count
0
InChi Key
LLJAQDVNMGLRBD-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H5N5O2/c8-7-11-5-4(6(14)12-7)10-3(2-13)1-9-5/h1-2H,(H3,8,9,11,12,14)
Chemical Name
2-amino-4-oxo-3H-pteridine-6-carbaldehyde
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

Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.  (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
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 5.2315 mL 26.1575 mL 52.3149 mL
5 mM 1.0463 mL 5.2315 mL 10.4630 mL
10 mM 0.5231 mL 2.6157 mL 5.2315 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.

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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?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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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:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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