| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
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| 500mg | |||
| 1g | |||
| Other Sizes |
| Targets |
Substrate for mammalian aminoimidazolecarboxamide ribotide (AICAR) transformylase (EC 2.1.2.3). [1]
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| ln Vitro |
10-HCO-H₂folate is identified as a better substrate for AICAR transformylase than 10-HCO-H₄folate, as noted from previous work cited in the introduction. [1]
It can be produced from 10-HCO-H₄folate via iron-catalyzed oxidation, which is inhibited by hydroxyl radical scavengers like mannitol and iron chelators like apotransferrin and deferoxamine, and stimulated by iron chelates like Fe³⁺-EDTA and Fe³⁺-citrate. [1] In microbiological assays using Lactobacillus casei, the growth response (measured by A₆₅₀) to 10-HCO-H₂folate (produced by ferric ammonium citrate oxidation) was 78% (±8%) that of a folic acid standard. In contrast, the unoxidized control (10-HCO-H₄folate) showed only 43% (±4%) activity. The higher activity is attributed to the loss of the asymmetric center at carbon 6 upon oxidation, allowing the microorganism to utilize the total folate concentration. [1] In an enzymatic assay, both air-oxidized and Fe³⁺-EDTA-catalyzed oxidation products of 10-HCO-H₄folate (which are 10-HCO-H₂folate) were able to convert 0.21 ± 0.2 μmol and 0.22 ± 0.3 μmol of AICAR to inosine monophosphate (IMP), respectively, in 1 hour using excess AICAR transformylase. This demonstrated that the product retains coenzyme activity. [1] |
| Enzyme Assay |
AICAR Transformylase Assay: The coenzyme activity of 10-HCO-H₂folate (produced by iron-catalyzed oxidation of 10-HCO-H₄folate) was assayed using a non-continuous colorimetric method with chicken liver AICAR transformylase. In the assay, 0.21 μmol of 10-HCO-H₄folate was oxidized (either by air or with Fe³⁺-EDTA) to produce the substrate. This product was then allowed to react with 0.50 μmol of AICAR in the presence of excess AICAR transformylase. The amount of IMP produced (0.21-0.22 μmol in 1 hour) was measured, confirming the enzymatic activity of the product as a formyl group donor. [1]
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| Cell Assay |
Microbiological Assay (L. casei): A 96-well microplate assay using Lactobacillus casei was performed to assess the folate activity of the oxidation product. Diluted samples of the iron-catalyzed oxidation product (10-HCO-H₂folate), a control (10-HCO-H₄folate), and a folic acid standard were tested at concentrations ranging from 20 to 1300 pM. Bacterial growth, measured as turbidity at 650 nm (A₆₅₀), was proportional to folate concentration. The biological activity of the product was expressed as a percentage of the folic acid standard's activity. [1]
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| References | |
| Additional Infomation |
10-Formyl dihydrofolate is a 10-formyl derivative of dihydrofolate. It is the conjugate acid of 10-formyl dihydrofolate (2-).
10-Formyl-7,8-dihydrofolic acid is a folate derivative where the pteridine ring is at the dihydro level of oxidation, with a formyl group attached at the N10 position. It is an intermediate oxidation state between the fully reduced tetrahydrofolate and the fully oxidized folic acid forms. [1] The study demonstrates that it can be formed non-enzymatically from 10-HCO-H₄folate through a reaction catalyzed by iron compounds. The mechanism is proposed to involve hydroxyl radicals (•OH) generated via Fenton chemistry, which abstract a hydrogen atom from carbon 6 of 10-HCO-H₄folate. [1] The removal of the chiral center at carbon 6 upon oxidation to the dihydro form means that 10-HCO-H₂folate is not a mixture of diastereomers, unlike the biologically active (6S) and inactive (6R) forms of 10-HCO-H₄folate. This explains its higher activity in the L. casei microbiological assay, as the bacterium can utilize the entire pool. [1] The presence of "free iron" (e.g., as iron citrate) in biological fluids like bile and cerebrospinal fluid, and intracellularly, suggests that this oxidation could occur in vivo. The authors speculate that 10-HCO-H₄folate may act as a hydroxyl radical scavenger. [1] The tentative identification of 10-HCO-H₂folate in human bile is mentioned as a potential example of its in vivo occurrence, linking it to enterohepatic circulation and folate homeostasis. [1] |
| Molecular Formula |
C20H21N7O7
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|---|---|
| Molecular Weight |
471.42344
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| Exact Mass |
471.15
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| CAS # |
28459-40-7
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| PubChem CID |
135398690
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.67g/cm3
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| LogP |
0.503
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
34
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| Complexity |
966
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| Defined Atom Stereocenter Count |
1
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| SMILES |
NC1NC(=O)C2=C(NCC(CC(NC3C=CC(C(NC(C(O)=O)CCC(O)=O)=O)=CC=3)=O)=N2)N=1
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| InChi Key |
UXFQDXABPXWSTK-ZDUSSCGKSA-N
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| InChi Code |
InChI=1S/C20H21N7O7/c21-20-25-16-15(18(32)26-20)23-11(7-22-16)8-27(9-28)12-3-1-10(2-4-12)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,13H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,22,25,26,32)/t13-/m0/s1
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| Chemical Name |
(2S)-2-[[4-[(2-amino-4-oxo-7,8-dihydro-3H-pteridin-6-yl)methyl-formylamino]benzoyl]amino]pentanedioic 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) |
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
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|---|---|
| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.1213 mL | 10.6063 mL | 21.2125 mL | |
| 5 mM | 0.4243 mL | 2.1213 mL | 4.2425 mL | |
| 10 mM | 0.2121 mL | 1.0606 mL | 2.1213 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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