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Acetyl-6-formylpterin (Ac-6-FP)

Cat No.:V86115 Purity: ≥98%
Acetyl-6-formylpterin (Ac-6-FP)
Acetyl-6-formylpterin (Ac-6-FP) Chemical Structure CAS No.: 29769-49-1
Product category: Others 14
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
Other Sizes
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Product Description
Acetyl-6-formylpterin (Ac-6-FP) is a hapten that covalently binds to MR1 via residue Lys43 of the protein, leading to upregulation of the protein. Acetyl-6-formylpterin (Ac-6-FP) can be used to study inflammation.
Acetyl-6-formylpterin (Ac-6-FP) is a pteridine derivative and a reductive amination product derived from folic acid (vitamin B9). It has a molecular formula of C9H7N5O3 and a molecular weight of 233.18. This compound is an inhibitor of mucosal-associated invariant T (MAIT) cell activation. It is also known as 2-Acetamido-6-formylpteridin-4-one and NSC 129965.
Biological Activity I Assay Protocols (From Reference)
Targets
Acetyl-6-formylpterin targets mucosal-associated invariant T (MAIT) cells, a subset of innate-like T cells that recognize vitamin B metabolites presented by the MHC-related protein 1 (MR1). The compound covalently binds to MR1 as a hapten and inhibits MAIT cell activation. It dose-dependently increases the surface expression of MR1 in WT3 cells overexpressing MR1 (WT3-m).
ln Vitro
In vitro, Acetyl-6-formylpterin inhibits MAIT cell activation. It dose-dependently increases the surface expression of MHC-related 1 (MR1) in WT3 cells overexpressing MR1 (WT3-m) following incubation with E. coli. However, it does not activate MAIT cells when cocultured with WT3-m cells at concentrations ranging from 0.23 to 15 µM. The compound's inhibitory activity is mediated through its binding to MR1.
ln Vivo
In vivo, Acetyl-6-formylpterin can be used in the study of inflammation. By inhibiting MAIT cell activation, the compound may modulate immune responses in inflammatory conditions. Detailed in vivo efficacy data, including effects in models of MAIT cell-mediated inflammation, are described in the primary literature. The compound's role as a MAIT cell inhibitor makes it a valuable tool for studying the function of these cells in health and disease.
Enzyme Assay
Non-cellular binding assays for Acetyl-6-formylpterin involve studying its interaction with MR1. The compound covalently binds to MR1 as a hapten. Binding can be assessed using surface plasmon resonance (SPR) or by monitoring MR1 surface expression in MR1-overexpressing cells. The compound's ability to inhibit MAIT cell activation can be measured using MAIT cell activation assays in the presence of antigen-presenting cells.
Cell Assay
In vitro cellular experiments with Acetyl-6-formylpterin are conducted using MAIT cells or MR1-expressing cell lines. WT3 cells overexpressing MR1 (WT3-m) are incubated with the compound in the presence or absence of E. coli, and MR1 surface expression is measured by flow cytometry. MAIT cell activation is assessed by measuring cytokine production (e.g., IFN-γ) or activation markers (e.g., CD69) following coculture with WT3-m cells.
Animal Protocol
In vivo animal studies for Acetyl-6-formylpterin are performed in mouse models of MAIT cell-mediated inflammation or infection. Animals are treated with the compound via appropriate routes of administration. Endpoints include assessment of MAIT cell activation, cytokine levels, and disease severity. The compound's ability to modulate MAIT cell responses in vivo is evaluated. Detailed protocols are described in the primary literature.
ADME/Pharmacokinetics
Acetyl-6-formylpterin has a molecular formula of C9H7N5O3 and a molecular weight of 233.18. The CAS number is 29769-49-1. Synonyms include Ac-6-FP, 2-Acetamido-6-formylpteridin-4-one, and NSC 129965. Purity is typically ≥95%. The compound is a crystalline solid. It is soluble in DMF (50 mg/mL), ethanol (1 mg/mL), and PBS pH 7.2 (0.1 mg/mL). It has a λmax of 284 nm. Storage is at -20°C.
Toxicity/Toxicokinetics
Toxicity data for Acetyl-6-formylpterin are limited as it is a research reagent. Standard laboratory safety precautions should be followed when handling this compound. The compound is a pteridine derivative and should be handled with appropriate personal protective equipment. It is for research use only and not for human therapeutic applications.
References

[1].Properties and reactivity of the folic acid and folate photoproduct 6-formylpterin. Free Radic Biol Med. 2021 Aug 1;171:1-10.

Additional Infomation
N(2)-acetyl-6-formylpterin is a pterin that is acetylated at the N-2 position and has a formyl group at the 6 position.
Acetyl-6-formylpterin is also known as Ac-6-FP. It is a degradation product of folic acid. The compound is an inhibitor of MAIT cell activation and is used in immunology research. It covalently binds to MR1 as a hapten. All products are for research use only and not for human therapeutic applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H7N5O3
Molecular Weight
233.18
Exact Mass
233.055
CAS #
29769-49-1
PubChem CID
135447887
Appearance
White to yellow solid powder
Density
1.72g/cm3
Index of Refraction
1.778
LogP
-1.4
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
2
Heavy Atom Count
17
Complexity
394
Defined Atom Stereocenter Count
0
SMILES
CC(=O)NC1=NC2=NC=C(N=C2C(=O)N1)C=O
InChi Key
DDBCPKAHJKOGKK-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H7N5O3/c1-4(16)11-9-13-7-6(8(17)14-9)12-5(3-15)2-10-7/h2-3H,1H3,(H2,10,11,13,14,16,17)
Chemical Name
N-(6-formyl-4-oxo-3H-pteridin-2-yl)acetamide
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 :~100 mg/mL (~428.85 mM; with sonication)
DMF :~50 mg/mL (~214.43 mM; with heating and sonication.)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.72 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one),clear solution.
For example, if 1 mL of working solution is to be prepared,you can add 100 μL of 25.0 mg/mL clear DMSO stock solution and add it to 900 μL of 20% SBE-β-CD saline solution and mix well.
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.

Solubility in Formulation 2: ≥ 2.5 mg/mL (10.72 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one),clear solution.
For example, if 1 mL of working solution is to be prepared,you can add 100 μL of 25.0 mg/mL clear DMSO stock solution and add it to 900 μL corn oil and mix well.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.2885 mL 21.4427 mL 42.8853 mL
5 mM 0.8577 mL 4.2885 mL 8.5771 mL
10 mM 0.4289 mL 2.1443 mL 4.2885 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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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)
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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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