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
• PubChem Substance ID: 24890768
• UNSPSC Code: 12352205
• MDL number: MFCD00036692
• NACRES: NA.75
• EC Number: 200-209-9
• Beilstein/REAXYS Number: 69045

Propriétés

• biological source: synthetic (organic)
• Quality Segment: 200
• product line: BioReagent
• assay: ≥97%
• form: powder
• technique(s): cell culture | mammalian: suitable
• color: yellow
• solubility: 2 M NaOH: 50 mg/mL, DMSO: soluble
• ε (extinction coefficient): 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
• shipped in: dry ice
• storage temp.: −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
• InChI key: TVZGACDUOSZQKY-LBPRGKRZSA-N
• Gene Information: human ... FPGS(2356) ; mouse ... Fpgs(14287)

Description

Application

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

Biochem/physiol Actions

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 that binds to dihydrofolate reductase and inhibits its activity.

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.

Other Notes

More potent, but more toxic, than methotrexate.

Informations sur la sécurité

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H300,H315,H319,H341,H360FD
• pcodes: P202 - P264 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 1 Oral - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2
• Classe de stockage: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges