10-Formyldihydrofolate
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    WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H597176

CAS#: 28459-40-7

Description: 10-Formyldihydrofolate is a Methotrexate metabolite; inhibits thymidylate synthetase and glycinamide ribotide transformylase.


Chemical Structure

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10-Formyldihydrofolate
CAS# 28459-40-7

Theoretical Analysis

Hodoodo Cat#: H597176
Name: 10-Formyldihydrofolate
CAS#: 28459-40-7
Chemical Formula: C20H21N7O7
Exact Mass: 471.1502
Molecular Weight: 471.43
Elemental Analysis: C, 50.96; H, 4.49; N, 20.80; O, 23.76

Price and Availability

Size Price Availability Quantity
5.0mg USD 355.0 2 Weeks
50.0mg USD 2000.0 2 Weeks
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Synonym: 10-Formyldihydrofolate;

IUPAC/Chemical Name: (4-(N-((2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl)formamido)benzoyl)-L-glutamic acid

InChi Key: UXFQDXABPXWSTK-ZDUSSCGKSA-N

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

SMILES Code: O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=C(N(CC2=NC3=C(NC(N)=NC3=O)NC2)C=O)C=C1)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

Instruction:

Preparing Stock Solutions

The following data is based on the product molecular weight 471.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Sah S, Shah RA, Govindan A, Varada R, Rex K, Varshney U. Utilisation of 10-formyldihydrofolate as substrate by dihydrofolate reductase (DHFR) and 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR) tranformylase/IMP cyclohydrolase (PurH) in Escherichia coli. Microbiology. 2018 May 25. doi: 10.1099/mic.0.000671. [Epub ahead of print] PubMed PMID: 29799386.

2: Naz N, Jimenez AR, Sanjuan-Vilaplana A, Gurney M, Miyan J. Neonatal hydrocephalus is a result of a block in folate handling and metabolism involving 10-formyltetrahydrofolate dehydrogenase. J Neurochem. 2016 Aug;138(4):610-23. doi: 10.1111/jnc.13686. Epub 2016 Jul 25. PubMed PMID: 27294849.

3: Baggott JE, Tamura T. Folate-Dependent Purine Nucleotide Biosynthesis in Humans. Adv Nutr. 2015 Sep 15;6(5):564-71. doi: 10.3945/an.115.008300. Print 2015 Sep. Review. PubMed PMID: 26374178; PubMed Central PMCID: PMC4561830.

4: Baggott JE, Tamura T. Evidence for the hypothesis that 10-formyldihydrofolate is the in vivo substrate for aminoimidazolecarboxamide ribotide transformylase. Exp Biol Med (Maywood). 2010 Mar;235(3):271-7. doi: 10.1258/ebm.2009.009151. Review. PubMed PMID: 20404044.

5: Brookes PS, Baggott JE. Oxidation of 10-formyltetrahydrofolate to 10-formyldihydrofolate by complex IV of rat mitochondria. Biochemistry. 2002 Apr 30;41(17):5633-6. PubMed PMID: 11969424.

6: Baggott JE, Tamura T. Metabolism of 10-formyldihydrofolate in humans. Biomed Pharmacother. 2001 Oct;55(8):454-7. Review. PubMed PMID: 11686579.

7: Baggott JE, Tamura T, Baker H. Re-evaluation of the metabolism of oral doses of racemic carbon-6 isomers of formyltetrahydrofolate in human subjects. Br J Nutr. 2001 Jun;85(6):653-7. Review. PubMed PMID: 11430769.

8: Baggott JE, Robinson CB, Johnston KE. Bioactivity of [6R]-5-formyltetrahydrofolate, an unusual isomer, in humans and Enterococcus hirae, and cytochrome c oxidation of 10-formytetrahydrofolate to 10-formyldihydrofolate. Biochem J. 2001 Feb 15;354(Pt 1):115-22. PubMed PMID: 11171086; PubMed Central PMCID: PMC1221635.

9: Baggott JE. Hydrolysis of 5,10-methenyltetrahydrofolate to 5-formyltetrahydrofolate at pH 2.5 to 4.5. Biochemistry. 2000 Nov 28;39(47):14647-53. PubMed PMID: 11087421.

10: Ruggeri S, Vahteristo LT, Aguzzi A, Finglas P, Carnovale E. Determination of folate vitamers in food and in Italian reference diet by high-performance liquid chromatography. J Chromatogr A. 1999 Sep 3;855(1):237-45. PubMed PMID: 10514988.

11: Baggott JE, Robinson CB, Eto I, Johanning GL, Cornwell PE. Iron compounds catalyze the oxidation of 10-formyl-5,6,7,8 tetrahydrofolic acid to 10-formyl-7,8 dihydrofolic acid. J Inorg Biochem. 1998 Sep;71(3-4):181-7. PubMed PMID: 9833324.

12: Baggott JE, Johanning GL, Branham KE, Prince CW, Morgan SL, Eto I, Vaughn WH. Cofactor role for 10-formyldihydrofolic acid. Biochem J. 1995 Jun 15;308 ( Pt 3):1031-6. PubMed PMID: 8948466; PubMed Central PMCID: PMC1136826.

13: Rhee MS, Coward JK, Galivan J. Depletion of 5,10-methylenetetrahydrofolate and 10-formyltetrahydrofolate by methotrexate in cultured hepatoma cells. Mol Pharmacol. 1992 Nov;42(5):909-16. PubMed PMID: 1435754.

14: Balinska M, Rhee M, Whiteley JM, Priest DG, Galivan J. Inhibition of mammalian thymidylate synthase by 10-formyltetrahydropteroylpolyglutamate. Arch Biochem Biophys. 1991 Jan;284(1):219-22. PubMed PMID: 1989499.

15: Drake JC, Baram J, Allegra CJ. Isolation and characterization of a novel dihydrofolate formylating enzyme from human MCF-7 breast cancer cells. Biochem Pharmacol. 1990 Feb 1;39(3):615-8. PubMed PMID: 2306274.

16: Baram J, Chabner BA, Drake JC, Fitzhugh AL, Sholar PW, Allegra CJ. Identification and biochemical properties of 10-formyldihydrofolate, a novel folate found in methotrexate-treated cells. J Biol Chem. 1988 May 25;263(15):7105-11. PubMed PMID: 3366769.

17: Pratt RF, Cooper BA. Folates in plasma and bile of man after feeding folic acid--3H and 5-formyltetrahydrofolate (folinic acid). J Clin Invest. 1971 Feb;50(2):455-62. PubMed PMID: 4992993; PubMed Central PMCID: PMC291942.

18: Pasquali P, Landi L, Bovina C, Marchetti M. Effects of thyroxine on the synthesis of folate coenzymes in rat liver. Biochem J. 1970 Jan;116(2):217-21. PubMed PMID: 5414097; PubMed Central PMCID: PMC1185348.