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A1784

Sigma-Aldrich

Aminopterin

powder

Sinônimo(s):

(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

Fórmula empírica (Notação de Hill):
C19H20N8O5
Número CAS:
54-62-6
Peso molecular:
440.41
Beilstein:
69045
Número CE:
200-209-9
Código UNSPSC:
12352200
ID de substância PubChem:
24278186
NACRES:
NA.77

fonte biológica

synthetic (organic)

Nível de qualidade

200

Ensaio

≥97% (TLC)

forma

powder

cor

yellow

pf

225 °C

solubilidade

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.)

ε (coeficiente de extinção)

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

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

chave InChI

TVZGACDUOSZQKY-LBPRGKRZSA-N

Informações sobre genes

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

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Ações bioquímicas/fisiológicas

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.

Características e benefícios

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Ligação

More potent, but more toxic, than methotrexate.

inibidor

Nº do produto
Descrição
Preços

Pictogramas

Skull and crossbonesHealth hazard
GHS06,GHS08

Palavra indicadora

Danger

Classificações de perigo

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

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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Methotrexate European Pharmacopoeia (EP) Reference Standard

M1000000

Methotrexate

Dihydrofolic acid ≥90%

Sigma-Aldrich

D7006

Dihydrofolic acid

Timidina powder, BioReagent, suitable for cell culture

Sigma-Aldrich

T1895

Timidina

Hypoxanthine powder, BioReagent, suitable for cell culture

Sigma-Aldrich

H9636

Hypoxanthine

Folinic acid calcium salt hydrate BioXtra, ≥99.0% (HPLC)

Sigma-Aldrich

47612

Folinic acid calcium salt hydrate

Timidina ≥99%

Sigma-Aldrich

T9250

Timidina

Tetrahydrofolic acid ≥65% (when packaged), powder

Sigma-Aldrich

T3125

Tetrahydrofolic acid

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
A Rosowsky
Current medicinal chemistry, 6(4), 329-352 (1999-04-02)
Nonpolyglutamatable antifolates are potentially of therapeutic interest for the treatment of tumors that are inherently refractory, or have become resistant, to classical antifolates as a result of decreased expression of the enzyme folylpolyglutamate synthetase. An interesting class of water-soluble nonpolyglutamatable
M Del Campo et al.
Teratology, 60(1), 10-12 (1999-07-21)
Maternal exposures to aminopterin and methotrexate have been associated with a pattern of malformation which includes prenatal-onset growth deficiency, severe lack of ossification of the calvarium, hypoplastic supraorbital ridges, small, low-set ears, micrognathia, and limb abnormalities. We report on a
Hatem A Azim et al.
Current opinion in oncology, 24(3), 325-331 (2012-02-22)
To discuss the clinical development of new formulations of old cytotoxic agents and highlight the value of adopting this strategy. Several drugs are currently in clinical development with high potential in improving clinical outcomes compared with their older counterparts. We
Edward C Keystone et al.
The Journal of rheumatology, 38(9), 1875-1883 (2011-07-05)
To investigate the potential efficacy, safety, and tolerability of daily use of CH-1504 in patients with active rheumatoid arthritis (RA). US National Institutes of Health database no. NCT00658047. In our phase II randomized double-blind double-dummy study, patients naive to methotrexate
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