Dihydrofolate | CAS#4033-27-6 | mammalian conversion of dietary folic acid

MedKoo Cat#: 597167 | Name: Dihydrofolate

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Description:

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

Dihydrofolate is an intermediate in mammalian conversion of dietary folic acid to tetrahydrofolate by dihydrofolate reductase (DHFR). In bacteria, dihydrofolic acid is generated from 7,8-dihydropteroate by dihydrofolate synthetase.

Chemical Structure

Dihydrofolate

CAS#4033-27-6

Theoretical Analysis

MedKoo Cat#: 597167

Name: Dihydrofolate

CAS#: 4033-27-6

Chemical Formula: C19H21N7O6

Exact Mass: 443.1553

Molecular Weight: 443.42

Elemental Analysis: C, 51.47; H, 4.77; N, 22.11; O, 21.65

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 350.00	2 Weeks
25mg	USD 650.00	2 Weeks

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Synonym

Dihydrofolate; 7,8-Dihydrofolic acid; Dihydrofolic acid; NSC 165989; NSC-165989; NSC165989;

IUPAC/Chemical Name

(4-(((2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl)amino)benzoyl)-L-glutamic acid

InChi Key

OZRNSSUDZOLUSN-LBPRGKRZSA-N

InChi Code

InChI=1S/C19H21N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1

SMILES Code

O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=C(NCC2=NC3=C(NC(N)=NC3=O)NC2)C=C1)=O

Appearance

Solid powder

Purity

>90% (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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Dihydrofolic acid is a folic acid derivative acted upon by dihydrofolate reductase to produce tetrahydrofolic acid.

In vitro activity:

Results obtained showed that folic acid induced a dose-dependent decrease in IGF-IR protein and mRNA levels in the HCT116 +/+ colon cancer cell line. This effect was associated with a significant reduction in IGF-IR promoter activity. Similar effects were elicited by the folic acid metabolites dihydrofolic acid and tetrahydrofolic acid. Reference: Endocr Relat Cancer. 2006 Jun;13(2):571-81. https://pubmed.ncbi.nlm.nih.gov/16728583/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMF	1.0	2.26
	DMSO	5.0	11.28

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 443.42 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.

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

Formulation protocol:

1. Attias Z, Werner H, Vaisman N. Folic acid and its metabolites modulate IGF-I receptor gene expression in colon cancer cells in a p53-dependent manner. Endocr Relat Cancer. 2006 Jun;13(2):571-81. doi: 10.1677/erc.1.01156. PMID: 16728583.

In vitro protocol:

In vivo protocol:

TBD

1: Smith SJ, Kamara ARY, Sahr F, Samai M, Swaray AS, Menard D, Warsame M. Efficacy of artemisinin-based combination therapies and prevalence of molecular markers associated with artemisinin, piperaquine and sulfadoxine-pyrimethamine resistance in Sierra Leone. Acta Trop. 2018 Jun 19. pii: S0001-706X(18)30138-4. doi: 10.1016/j.actatropica.2018.06.016. [Epub ahead of print] PubMed PMID: 29932931. 2: Shiao SPK, Grayson J, Lie A, Yu CH. Personalized Nutrition-Genes, Diet, and Related Interactive Parameters as Predictors of Cancer in Multiethnic Colorectal Cancer Families. Nutrients. 2018 Jun 20;10(6). pii: E795. doi: 10.3390/nu10060795. PubMed PMID: 29925788. 3: Park S, Burke RE, Kareva T, Kholodilov N, Aimé P, Franke TF, Levy O, Greene LA. Context-dependent expression of a conditionally-inducible form of active Akt. PLoS One. 2018 Jun 19;13(6):e0197899. doi: 10.1371/journal.pone.0197899. eCollection 2018. PubMed PMID: 29920520. 4: Duff MR, Borreguero JM, Cuneo M, Ramanathan A, He J, Kamath G, Chennubhotla CS, Meilleur F, Howell EE, Herwig KW, Myles DAA, Agarwal PK. Modulating enzyme activity by altering protein dynamics with solvent. Biochemistry. 2018 Jun 14. doi: 10.1021/acs.biochem.8b00424. [Epub ahead of print] PubMed PMID: 29901984. 5: Francesconi V, Giovannini L, Santucci M, Cichero E, Costi MP, Naesens L, Giordanetto F, Tonelli M. Synthesis, biological evaluation and molecular modeling of novel azaspiro dihydrotriazines as influenza virus inhibitors targeting the host factor dihydrofolate reductase (DHFR). Eur J Med Chem. 2018 Jun 2;155:229-243. doi: 10.1016/j.ejmech.2018.05.059. [Epub ahead of print] PubMed PMID: 29886325. 6: Gomha SM, Edrees MM, Muhammad ZA, El-Reedy AA. 5-(Thiophen-2-yl)-1,3,4-thiadiazole derivatives: synthesis, molecular docking and in vitro cytotoxicity evaluation as potential anticancer agents. Drug Des Devel Ther. 2018 May 30;12:1511-1523. doi: 10.2147/DDDT.S165276. eCollection 2018. PubMed PMID: 29881258; PubMed Central PMCID: PMC5985782. 7: Corral MG, Haywood J, Stehl LH, Stubbs KA, Murcha MW, Mylne JS. Targeting plant DIHYDROFOLATE REDUCTASE with antifolates and mechanisms for genetic resistance. Plant J. 2018 Jun 7. doi: 10.1111/tpj.13983. [Epub ahead of print] PubMed PMID: 29876984. 8: Matange N, Bodkhe S, Patel M, Shah P. Trade-offs with stability modulate innate and mutationally acquired drug-resistance in bacterial dihydrofolate reductase enzymes. Biochem J. 2018 Jun 5. pii: BCJ20180249. doi: 10.1042/BCJ20180249. [Epub ahead of print] PubMed PMID: 29871875. 9: Organista-Nava J, Gómez-Gómez Y, Illades-Aguiar B, Rivera-Ramírez AB, Saavedra-Herrera MV, Leyva-Vázquez MA. Overexpression of dihydrofolate reductase is a factor of poor survival in acute lymphoblastic leukemia. Oncol Lett. 2018 Jun;15(6):8405-8411. doi: 10.3892/ol.2018.8429. Epub 2018 Apr 4. PubMed PMID: 29805575; PubMed Central PMCID: PMC5950508. 10: 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. 11: Schittmayer M, Birner-Gruenberger R, Zamboni N. Quantification of Cellular Folate Species by LC-MS after Stabilization by Derivatization. Anal Chem. 2018 Jun 19;90(12):7349-7356. doi: 10.1021/acs.analchem.8b00650. Epub 2018 Jun 5. PubMed PMID: 29792680; PubMed Central PMCID: PMC6011177. 12: Carey PR, Whitmer GR, Yoon MJ, Lombardo MN, Pusztai-Carey M, Heidari-Torkabadi H, Che T. Measuring Drug-Induced Changes in Metabolite Populations of Live Bacteria: Real Time Analysis by Raman Spectroscopy. J Phys Chem B. 2018 Jun 21;122(24):6377-6385. doi: 10.1021/acs.jpcb.8b03279. Epub 2018 Jun 7. PubMed PMID: 29792435. 13: Tobias AM, Toska D, Lange K, Eck T, Bhat R, Janson CA, Rotella DP, Gubler U, Goodey NM. Expression, purification, and inhibition profile of dihydrofolate reductase from the filarial nematode Wuchereria bancrofti. PLoS One. 2018 May 22;13(5):e0197173. doi: 10.1371/journal.pone.0197173. eCollection 2018. PubMed PMID: 29787565; PubMed Central PMCID: PMC5963757. 14: Zhang XJ, Wang XW, Sun JX, Su C, Yang S, Zhang WB. Synergistic Enhancement of Enzyme Performance and Resilience via Orthogonal Peptide-Protein Chemistry Enabled Multilayer Construction. Biomacromolecules. 2018 Jun 15. doi: 10.1021/acs.biomac.8b00306. [Epub ahead of print] PubMed PMID: 29768002. 15: Huang DB, Dryden M. Iclaprim, a dihydrofolate reductase inhibitor antibiotic in Phase III of clinical development: a review of its pharmacology, microbiology and clinical efficacy and safety. Future Microbiol. 2018 May 10. doi: 10.2217/fmb-2018-0061. [Epub ahead of print] PubMed PMID: 29742926. 16: Teles ALB, Silva RR, Ko M, Ferreira GM, Pita SDR, Trossini GHG, Carvalho P, Castilho MS. Identification, characterization and molecular modelling studies of Schistosoma mansoni Dihydrofolate Reductase inhibitors: From assay development to hit identification. Curr Top Med Chem. 2018 May 9. doi: 10.2174/1568026618666180509150134. [Epub ahead of print] PubMed PMID: 29741139. 17: Makita S, Maeshima AM, Maruyama D, Izutsu K, Tobinai K. Forodesine in the treatment of relapsed/refractory peripheral T-cell lymphoma: an evidence-based review. Onco Targets Ther. 2018 Apr 20;11:2287-2293. doi: 10.2147/OTT.S140756. eCollection 2018. Review. PubMed PMID: 29719411; PubMed Central PMCID: PMC5916385. 18: Charnaud SC, Jonsdottir TK, Sanders PR, Bullen HE, Dickerman BK, Kouskousis B, Palmer CS, Pietrzak HM, Laumaea AE, Erazo AB, McHugh E, Tilley L, Crabb BS, Gilson PR. Spatial organization of protein export in malaria parasite blood stages. Traffic. 2018 Apr 26. doi: 10.1111/tra.12577. [Epub ahead of print] PubMed PMID: 29696751. 19: Li H, Fang F, Liu Y, Xue L, Wang M, Guo Y, Wang X, Tian C, Liu J, Zhang Z. Inhibitors of dihydrofolate reductase as antitumor agents: design, synthesis and biological evaluation of a series of novel nonclassical 6-substituted pyrido[3,2-d]pyrimidines with a three- to five-carbon bridge. Bioorg Med Chem. 2018 May 15;26(9):2674-2685. doi: 10.1016/j.bmc.2018.04.035. Epub 2018 Apr 19. PubMed PMID: 29691154. 20: Shah K, Lin X, Queener SF, Cody V, Pace J, Gangjee A. Targeting species specific amino acid residues: Design, synthesis and biological evaluation of 6-substituted pyrrolo[2,3-d]pyrimidines as dihydrofolate reductase inhibitors and potential anti-opportunistic infection agents. Bioorg Med Chem. 2018 May 15;26(9):2640-2650. doi: 10.1016/j.bmc.2018.04.032. Epub 2018 Apr 17. PubMed PMID: 29691153; PubMed Central PMCID: PMC5967623.