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Merck

A3411

Sigma-Aldrich

Aminopterin

powder, BioReagent, suitable for cell culture

Synonym(e):

(S)-2-{4-[(2,4-Diaminopteridin-6-yl)-methylamino]-benzamido}-pentandisäure, 4-Amino-pteroyl-L-glutaminsäure, 4-Aminofolsäure, erythro-2-Amino-1-phenyl-1-propanol -hydrochlorid

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About This Item

Empirische Formel (Hill-System):
C19H20N8O5
CAS-Nummer:
Molekulargewicht:
440.41
Beilstein:
69045
EG-Nummer:
UNSPSC-Code:
12352205
PubChem Substanz-ID:
NACRES:
NA.75

Biologische Quelle

synthetic (organic)

Qualitätsniveau

Produktlinie

BioReagent

Assay

≥97%

Form

powder

Methode(n)

cell culture | mammalian: suitable

Farbe

yellow

Löslichkeit

2 M NaOH: 50 mg/mL
DMSO: soluble

ε (Extinktionskoeffizient)

24,500 at 282 nm in 0.1 M NaOH at 1 M
25,700 at 261 nm in 0.1 M NaOH at 1 M
8,100 at 373 nm in 0.1 M NaOH at 1 M

Versandbedingung

dry ice

Lagertemp.

−20°C

SMILES String

Nc1nc(N)c2nc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cnc2n1

InChI

1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27)/t12-/m0/s1

InChIKey

TVZGACDUOSZQKY-LBPRGKRZSA-N

Angaben zum Gen

human ... FPGS(2356)
mouse ... Fpgs(14287)

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Anwendung

Aminopterin has been used in the production of anti- neurogranin antibodies.

Biochem./physiol. Wirkung

Aminopterin is found to inhibit growth, embryogenesis and has toxic effects in mice models. It serves as a abortifacient. Aminopterin is known to reduce the effects of acute leukemia in children.
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.

Verlinkung

Wirksamer aber auch toxischer als Methotrexat

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Piktogramme

Skull and crossbonesHealth hazard

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 1 Oral - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2

Lagerklassenschlüssel

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Die Dokumentenbibliothek aufrufen

Serum neurogranin measurement as a biomarker of acute traumatic brain injury
Yang J, et al.
Clinical Biochemistry, 48, 843-848 (2015)
Drugs and Nutrients: The Interactive Effects, 308-308 (1984)
Drugs and Nutrients: The Interactive Effects, 308-308 (1984)
Phase II trial of oral aminopterin for adults and children with refractory acute leukemia
Cole PD, et al.
Clinical Cancer Research, 11(22), 8089-8096 (2005)
Aleem Gangjee et al.
Journal of medicinal chemistry, 48(16), 5329-5336 (2005-08-05)
We report, for the first time, the biological activities of four-carbon-atom bridged classical antifolates on dihydrofolate reductase (DHFR), thymidylate synthase (TS), and folylpolyglutamate synthetase (FPGS) as well as antitumor activity. Extension of the bridge homologation studies of classical two-carbon bridged

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