Methotrexate

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Cat.No. 1230 - Methotrexate | C20H22N8O5 | CAS No. 59-05-2
Description: Cytotoxic agent
Chemical Name: N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid
Purity: ≥99% (HPLC)
Datasheet
Citations (1)
Reviews
Literature

Biological Activity

Cytotoxic agent. Inhibits thymidylate synthetase and de novo purine synthesis. Potent folic acid antagonist; inhibits dihydrofolate reductase. Also inhibits Ras carboxyl methylation in DKOB8 cells, leading to decreased p44 and Akt activation.

Technical Data

M. Wt 454.44
Formula C20H22N8O5
Storage Store at RT
Purity ≥99% (HPLC)
CAS Number 59-05-2
PubChem ID 126941
InChI Key FBOZXECLQNJBKD-ZDUSSCGKSA-N
Smiles O=C(N[C@H]([C@](O)=O)CCC(O)=O)C(C=C3)=CC=C3N(CC2=NC1=C(N)N=C(N)N=C1N=C2)C

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solubility Soluble to 100 mM in DMSO

Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

Allegra et al (1987) Evidence for direct inhibition of de novo protein synthesis in human MCF-7 breast cells as a principal mode of metabolic inhibition by methotrexate. J.Biol.Chem. 262 13520 PMID: 2443493

Chu et al (1990) Mechanism of thymidylate synthase inhibition by methotrexate in human neoplastic cell lines and normal human myeloid progenitor cells. J.Biol.Chem. 265 8470 PMID: 2341391

Jolivet et al (1983) The pharmacology and clinical use of methotrexate. N.Engl.J.Med. 309 1094 PMID: 6353235

Winter-Vann et al (2003) Targeting Ras signaling through inhibition of carboxyl methylation: an unexpected property of methotrexate. Proc.Natl.Acad.Sci.U.S.A. 100 6529 PMID: 12750467


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Keywords: Methotrexate, Methotrexate supplier, Cytotoxic, agent, Dihydrofolate, reductases, inhibitors, inhibits, Cell, Cycle, DHFR, chemotherapeutics, Reductase, Inhibitors, 1230, Tocris Bioscience

⚠ WARNING: This product can expose you to chemicals including Methotrexate, which is known to the State of California to cause reproductive toxicity with developmental effects. For more information, go to www.P65Warnings.ca.gov

1 Citation for Methotrexate

Citations are publications that use Tocris products. Selected citations for Methotrexate include:

Robinson et al (2013) RB1 status in triple negative breast cancer cells dictates response to radiation treatment and selective therapeutic drugs. PLoS One 8 e78641 PMID: 24265703


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Literature in this Area

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Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
Cell Cycle & DNA Damage Repair

Cell Cycle & DNA Damage Repair Poster

In normal cells, each stage of the cell cycle is tightly regulated, however in cancer cells many genes and proteins that are involved in the regulation of the cell cycle are mutated or over expressed. Adapted from the 2015 Cancer Product Guide, Edition 3, this poster summarizes the stages of the cell cycle and DNA repair. It also highlights strategies for enhancing replicative stress in cancer cells to force mitotic catastrophe and cell death.