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SBR00016

Sigma-Aldrich

Aminopterin Ready Made Solution

50 mg/mL in DMSO

Synonim(y):

(S)-2-{4-[(2,4-Diaminopteridin-6-yl)methylamino]benzamido}pentanedioic acid, 4-Amino-PGA, 4-Aminofolic acid, 4-Aminopteroyl-L-glutamic acid

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About This Item

Wzór empiryczny (zapis Hilla):
C19H20N8O5
Numer CAS:
54-62-6
Masa cząsteczkowa:
440.41
Numer MDL:
MFCD00036692
Kod UNSPSC:
12352205
NACRES:
NA.76

Próba

≥85%

Poziom jakości

200

Postać

liquid

warunki przechowywania

protect from light

stężenie

50 mg/mL in DMSO

rozpuszczalność

DMSO: 50 mg/mL

Warunki transportu

dry ice

temp. przechowywania

−20°C

ciąg SMILES

OC(CC[C@@H](C(O)=O)NC(C1=CC=C(NCC2=NC3=C(N)N=C(N)N=C3N=C2)C=C1)=O)=O

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)

Klucz InChI

TVZGACDUOSZQKY-UHFFFAOYSA-N

Działania biochem./fizjol.

Aminopterin is a synthetic derivative of pterin. It is used as a folic acid antagonist. It competitively inhibits dihydrofolate reductase (DHFR) and blocks tetrahydrofolate synthesis. This inhibition blocks DNA, RNA and protein synthesis.

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.

Aminopterin was first administered for cancer therapy, as a drug targeting metabolism, specifically in pediatric leukemia. Later on it was demonstrated to be more potent yet more toxic than methotrexate.
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Piktogramy

Skull and crossbonesHealth hazard
GHS06,GHS08

Hasło ostrzegawcze

Danger

Zwroty wskazujące rodzaj zagrożenia

H301,H341,H360FD

Zwroty wskazujące środki ostrożności

P202 - P264 - P270 - P280 - P301 + P310 - P405

Klasyfikacja zagrożeń

Acute Tox. 3 Oral - Muta. 2 - Repr. 1B

Kod klasy składowania

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Klasa zagrożenia wodnego (WGK)

WGK 3

Temperatura zapłonu (°F)

188.6 °F

Temperatura zapłonu (°C)

87 °C

Certyfikaty analizy (CoA)

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Dokumenty związane z niedawno zakupionymi produktami zostały zamieszczone w Bibliotece dokumentów.

Odwiedź Bibliotekę dokumentów

A quantitative comparison of the antileukemic effectiveness of two folic acid antagonists in mice.
A GOLDIN et al.
Journal of the National Cancer Institute, 15(6), 1657-1664 (1955-06-01)
Michele Visentin et al.
Hematology/oncology clinics of North America, 26(3), 629-648 (2012-04-24)
This article focuses on the cellular, biochemical, and molecular pharmacology of antifolates and how a basic understanding of the mechanism of action of methotrexate, its cytotoxic determinants, mechanisms of resistance, and transport into and out of cells has led to
Temporary remissions in acute leukemia in children produced by folic acid antagonist, 4-aminopteroyl-glutamic acid.
S FARBER et al.
The New England journal of medicine, 238(23), 787-793 (1948-06-03)
Antagonist for pteroylglutamic acid.
D R SEEGER et al.
Journal of the American Chemical Society, 69(10), 2567-2567 (1947-10-01)

Produkty

Folic Acid Metabolism: A Role in Cancer's Cause and Cure

This article reviews some of our newest and most innovative technologies and their specific applications toward cancer research. It describes how complex the disease of cancer is, and how difficult it is to identify one topic that is completely unrelated to any other.

Folic Acid Metabolism in Cancer

This issue of Biofiles reviews some of our newest and most innovative technologies and their specific applications toward cancer research. In preparing this issue of Biofiles, one is reminded how complex the disease of cancer is, and how difficult it is to identify one topic that is completely unrelated to any other.

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