氨甲蝶呤/甲氨蝶呤/甲氨基叶酸/氨甲叶酸/二水合氨甲嘌呤/Methotrexate/（+）-Amet

 Description
Biochem/physiol Actions Folic acid antagonist and potent anticancer agent. Blocks DNA synthesis by blocking the production of tetrahydrofolate covactors required for the synthesis of thymidine. Amethopterin is actively transported into cells by the folate transporter. In the cell, it is converted to a high molecular weight polyglutamate metabolite by folylpolyglutamate synthase that, in turn, binds to dihydrofolate reductase and inhibits its activity. Amethopterin-polyglutamate is degraded intracellularly by γ-glutamyl hydrolase.
Reconstitution Add a minimal amount of 0.1 N NaOH to solubilize, then dilute in neutral buffer or saline. Diluted stock is stable for 1 week refrigerated and for 1 month frozen at −20 °C. References: Cell & Tissue Culture: Laboratory Procedures, Chapter 27, Page 27D:3.2 （A. Doyle, et al., eds, John Wiley） and Cell Biology: A Laboratory Handbook, vol. 2, page 417 （Julio E. Celis, ed., Academic Press）.

Properties
assay ≥99%
form powder
color yellow to yellow with an orange cast
solubility H2O: insoluble
  NaOH: soluble （minimal amount of 0.1 N NaOH to solubilize, then dilute in neutral buffer or saline）
Gene Information human ... DHFRP1（573971）, FPGS（2356）, SLC19A1（6573）, TYMS（7298）
  rat ... Dhfr（24312）
  mouse ... Dhfr（13361）
storage temp. −20°C

Safety
Personal Protective Equipment Eyeshields, Faceshields, full-face particle respirator type N100 （US）, Gloves, respirator cartridge type N100 （US）, type P1 （EN143） respirator filter, type P3 （EN 143） respirator cartridges
Hazard Codes T
Risk Statements 61-25-36/38
Safety Statements 53-26-36/37-45
RIDADR UN1544 6.1/PG 2
WGK Germany 3
RTECS MA1224100

References
reference Sharif, K.A., et al., Concentrating capacity of the human reduced folate carrier （hRFC1） in human ZR-75 breast cancer cell lines. Biochem. Pharmacol. 55, 1683-1689, （1998） Abstract
  Jansen, G., et al., Regulation of carrier-mediated transport of folates and antifolates in methotrexate-sensitive and -resistant leukemia cells. Adv. Enzyme Regul. 37, 59-76, （1997） Abstract
  Longo, G. S., et al., γ-Glutamyl hydrolase and folylpolyglutamate synthetase activities predict polyglutamylation of methotrexate in acute leukemias. Oncol. Res. 9, 259-263, （1997） Abstract
  Kumar, P., et al., Interaction of polyglutamyl derivatives of methotrexate, 10-deazaaminopterin, and dihydrofolate with dihydrofolate reductase. Cancer Res. 46, 5020-5023, （1986） Abstract
  Kumar, P., et al., Inhibition of human dihydrofolate reductase by antifolyl polyglutamates. Biochem. Pharmacol. 38, 541-543, （1989） Abstract
  Rhee, M.S., et al., Characterization of human cellular γ-glutamyl hydrolase. Mol. Pharmacol. 53, 1040-1046, （1998） Abstract
  Doyle, J.B., et al. Cell and Tissue Culture: Laboratory Procedures, 27D
  Yao, R., et al., Human γ-glutamyl hydrolase: cloning and characterization of the enzyme expressed in vitro. Proc. Natl. Acad. Sci. U. S. A. 93, 10134-10138, （1996） Abstract
  Aldrich MSDS 1, 54:D / Corp MSDS 1 （1）, 129:B / FT-IR 2 （3）, 3973:A / FT-IR 1 （2）, 898:B / IR-Spectra （3）, 1416:F / RegBook 1 （3）, 3539:D / RegBook 1 （2）, 2663:G / Sigma FT-IR 1 （2）, 252:C / Structure Index 1, 419:B:1

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