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A3411

Sigma-Aldrich

Aminopterin

powder, BioReagent, suitable for cell culture

Synonym(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

Empirical Formula (Hill Notation):
C19H20N8O5
CAS Number:
Molecular Weight:
440.41
Beilstein:
69045
EC Number:
UNSPSC Code:
12352205
PubChem Substance ID:
NACRES:
NA.75

biological source

synthetic (organic)

Quality Level

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)

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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. 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.

Linkage

More potent, but more toxic, than methotrexate.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Drugs and Nutrients: The Interactive Effects, 308-308 (1984)
Phase II trial of oral aminopterin for adults and children with refractory acute leukemia
Cole PD, et al.
Clinical Cancer Research, 11(22), 8089-8096 (2005)
Serum neurogranin measurement as a biomarker of acute traumatic brain injury
Yang J, et al.
Clinical Biochemistry, 48, 843-848 (2015)
Drugs and Nutrients: The Interactive Effects, 308-308 (1984)
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

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