A3411

Aminopterin

powder, BioReagent, suitable for cell culture

• Synonyme(s) : (S)-2-{4-[(2,4-Diaminopteridin-6-yl)methylamino]benzamido}pentanedioic acid, 4-Amino-PGA, 4-Aminofolic acid, 4-Aminopteroyl-L-glutamic acid
• Formule empirique (notation de Hill): C₁₉H₂₀N₈O₅
• Numéro CAS: 54-62-6
• Poids moléculaire : 440.41
• Numéro Beilstein : 69045
• Numéro CE : 200-209-9
• Code UNSPSC : 12352205
• ID de substance PubChem : 24890768
• Nomenclature NACRES : NA.75

Propriétés

• Source biologique: synthetic (organic)
• Niveau de qualité: 200
• Gamme de produits: BioReagent
• Pureté: ≥97%
• Forme: powder
• Technique(s): cell culture | mammalian: suitable
• Couleur: yellow
• Solubilité: 2 M NaOH: 50 mg/mL; DMSO: soluble
• ε (coefficient d'extinction): 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
• Conditions d'expédition: dry ice
• Température de stockage: −20°C
• Chaîne 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
• Clé InChI: TVZGACDUOSZQKY-LBPRGKRZSA-N
• Informations sur le gène: human ... FPGS(2356) ; mouse ... Fpgs(14287)

Description

Application

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

Actions biochimiques/physiologiques

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.

Liaison

More potent, but more toxic, than methotrexate.

Informations sur la sécurité

• Pictogrammes: GHS06,GHS08
• Mention d'avertissement: Danger
• Mentions de danger: H300,H315,H319,H341,H360FD
• Conseils de prudence: P202 - P264 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• Classification des risques: Acute Tox. 1 Oral - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2
• Code de la classe de stockage: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges