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Description
Biochem/physiol Actions Folic acid antagonist. Aminopterin 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. Aminopterin-polyglutamate is degraded intracellularly by γ-glutamyl hydrolase.
Linkage More potent, but more toxic, than methotrexate.
Properties
assay ~98% (TLC)
form powder
color yellow
solubility 2 M NaOH: 50 mg/mL (Solutions may be stored for 1-2 days at 4°C.)
DMSO: soluble (Solutions may be stored for 1-2 days at 4°C.)
abs. ε1M/261 nm, 0.1 M NaOH 25,700
ε1M/282 nm, 0.1 M NaOH 24,500
ε1M/373 nm, 0.1 M NaOH 8,100
Gene Information human ... FPGS(2356)
mouse ... Fpgs(14287)
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 61-28
Safety Statements 53-28-36/37-45
RIDADR UN2811 6.1/PG 1
WGK Germany 3
RTECS MA1050000
References
reference Roy, K., et al., A single amino acid difference within the folate transporter encoded by the murine RFC-1 gene selectively alters its interaction with folate analogues. J. Biol. Chem. 273, 2526-2531, (1998)
Rumberger, B.G., et al., Differing specificities for 4-aminofolate analogues of folylpolyglutamyl synthetase from tumors and proliferative intestinal epithelium of the mouse. Cancer Res. 50, 4639-4643, (1990)
Matherly, L.H., et al., Enhanced polyglutamylation of aminopterin relative to methotrexate in the Ehrlich ascites tumor cell in vitro. Cancer Res. 45, 1073, (1985)
Merck Merck 13,471
Beilstein Beil. 26,IV,3831
FT-NMR 1 (3), 481:A / RegBook 1 (2), 2663:E / Sax 6, 247 / Structure Index 1, 418:E:8
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