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| Targets |
Pteroic acid has a metabolic target, folylpolyglutamate synthetase (FPGS). It has been shown to activate the glutamylation of methotrexate by folylpolyglutamate synthetase. Pteroic acid is a degradation product of folic acid and is a component of the folic acid molecule, lacking the glutamate residue. It does not have a direct therapeutic target but is used as a tool to study folate metabolism and as an impurity marker in pharmaceutical quality control.
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| ln Vitro |
Pteroic acid has been shown to activate the glutamylation of methotrexate by folylpolyglutamate synthetase (FPGS). It does not have direct anticancer or antibacterial activity by itself, as it lacks the glutamate moiety required for polyglutamation and cellular retention. It is primarily used as a synthetic intermediate for folic acid derivatives and as an impurity standard for quality control.
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| ln Vivo |
Specific in vivo activity data for Pteroic acid is not provided. As a metabolite and degradation product of folic acid, it is not administered as a therapeutic agent. It may have activity in the folate pathway, but it is not a drug. The in vivo activity of pteroic acid is not characterized, as it is typically considered an inactive metabolite.
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| Enzyme Assay |
Pteroic acid can be used as a reference standard in cell-free assays for enzymes involved in folate metabolism. Procedure: Folylpolyglutamate synthetase (FPGS) activity is measured by incubating purified FPGS (10 ug) with varying concentrations of pteroic acid (0.1-100 uM) and [3H]-methotrexate (50 uM) in assay buffer (50 mM Tris-HCl, pH 8.4, 10 mM MgCl2, 10 mM ATP, 50 mM KCl) for 30-60 minutes at 37degC. The reaction is stopped, and the products are separated by HPLC or anion exchange chromatography. The amount of [3H]-methotrexate polyglutamates is quantified by scintillation counting.
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| Cell Assay |
Pteroic acid is not used in cell-based assays for cytotoxicity or cell proliferation. It can be used as an analytical standard to quantify pteroic acid levels in cell culture or biological samples by LC-MS/MS. Procedure: Cells are lysed, and the lysate is spiked with pteroic acid as an internal standard. Proteins are precipitated with acetonitrile. The supernatant is analyzed by LC-MS/MS using a C18 column. The concentration is calculated from a calibration curve generated with the pteroic acid standard.
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| Animal Protocol |
Not applicable. Pteroic acid is not used in animal studies as a test article for efficacy. It is an impurity standard and analytical chemical used in quality control. For toxicology studies, it may be used as a reference standard to quantify pteroic acid levels in biological samples after folic acid administration.
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| ADME/Pharmacokinetics |
Not applicable. Pteroic acid is a chemical reference standard, not an active pharmaceutical ingredient. Its own ADME properties are not relevant. It is slightly soluble in aqueous base and DMSO. The compound is stored at 2-8degC. It is a yellow powder that is slightly soluble in aqueous NaOH.
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| Toxicity/Toxicokinetics |
Specific toxicology data for Pteroic acid is not provided. As a component and degradation product of folic acid, it is likely to have low toxicity. However, pteroic acid is not a nutrient; folic acid is the essential vitamin. Standard laboratory safety precautions for handling organic compounds should be followed.
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| Additional Infomation |
Pteroic acid is a pteric acid. Functionally, it is associated with 2-aminopteridin-4-ol. It is the conjugate base of 2-amino-6-{[(4-carboxyphenyl)amino]methyl}-4-hydroxypteridin-1-onium. It is the conjugate acid of 4-{[(2-amino-4-hydroxypteridin-6-yl)methyl]amino}benzoic acid. It is a tautomer of 4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}benzoic acid and 4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}benzoic acid.
Structure Pteroic acid is a folic acid derivative and is a constituent as well as a degradation product of folic acid formed via enzymatic hydrolysis. It has been shown to activate the glutamylation of methotrexate by folylpolyglutamate synthetase. It is used as a synthetic intermediate for folic acid derivatives and as an impurity standard for quality control in pharmaceutical manufacturing. This product is for research use only and is not an approved drug. |
| Molecular Formula |
C14H12N6O3
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|---|---|
| Molecular Weight |
312.28
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| Exact Mass |
312.097
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| CAS # |
119-24-4
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| PubChem CID |
135398749
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| Appearance |
Typically exists as solids at room temperature
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| Density |
1.7±0.1 g/cm3
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| Boiling Point |
659.8ºC at 760mmHg
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| Melting Point |
>400ºC
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| Flash Point |
352.9ºC
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| Vapour Pressure |
2.61E-18mmHg at 25°C
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| Index of Refraction |
1.803
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| LogP |
-0.88
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
23
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| Complexity |
503
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C1C2C(N=C(N([H])[H])N1[H])=NC([H])=C(C([H])([H])N([H])C1C([H])=C([H])C(C(=O)O[H])=C([H])C=1[H])N=2
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| InChi Key |
JOAQINSXLLMRCV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C14H12N6O3/c15-14-19-11-10(12(21)20-14)18-9(6-17-11)5-16-8-3-1-7(2-4-8)13(22)23/h1-4,6,16H,5H2,(H,22,23)(H3,15,17,19,20,21)
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| Chemical Name |
4-[(2-amino-4-oxo-3H-pteridin-6-yl)methylamino]benzoic acid
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| Synonyms |
Pteroic acid
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
0.5 M NaOH : ~50 mg/mL (~160.11 mM; adjust pH to 12 with H2O)
DMSO : ~5.6 mg/mL (~17.93 mM; ultrasonic and warming and adjust pH to 11 with 1 M NaOH and heat to 60°C) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 0.62 mg/mL (1.99 mM) in 10% DMSO +40% PEG300 +5% Tween-80 +45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 0.62 mg/mL (1.99 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 the 6.2 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD in saline 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2023 mL | 16.0113 mL | 32.0225 mL | |
| 5 mM | 0.6405 mL | 3.2023 mL | 6.4045 mL | |
| 10 mM | 0.3202 mL | 1.6011 mL | 3.2023 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.
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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