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
• Beilstein: 69045
• Numéro CE : 200-209-9
• Numéro MDL: MFCD00036692
• 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
• Essai: ≥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.[1]

Actions biochimiques/physiologiques

Aminopterin is found to inhibit growth, embryogenesis and has toxic effects in mice models. It serves as a abortifacient.[2] Aminopterin is known to reduce the effects of acute leukemia in children.[3]

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