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Key Documents

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A1784

Sigma-Aldrich

Aminopterin

powder

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:
54-62-6
Molecular Weight:
440.41
Beilstein:
69045
EC Number:
200-209-9
MDL number:
MFCD00036692
UNSPSC Code:
12352200
PubChem Substance ID:
24278186
NACRES:
NA.77
Pricing and availability is not currently available.

biological source

synthetic (organic)

Quality Level

200

Assay

≥97% (TLC)

form

powder

color

yellow

mp

225 °C

solubility

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 (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

storage temp.

−20°C

SMILES string

Nc1nc(N)c2nc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cnc2n1

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This Item
EZFITSAM3EZFITSAM6EZFITMHTA3
EZ-Fit® Manifold 1-place manifold, for use with EZ-Fit® Filtration Unit, 316L stainless steel

EZFITSAM1

EZ-Fit® Manifold

EZ-Fit® Manifold 3-place manifold, for use with EZ-Fit® Filtration Unit, stainless steel

EZFITSAM3

EZ-Fit® Manifold

EZ-Fit® Manifold 6-place manifold, for use with EZ-Fit® Filtration Unit, 316L stainless steel

EZFITSAM6

EZ-Fit® Manifold

EZ-Fit® Manifold Filtration Head for use with EZ-Fit® Filtration Manifold, For use with EZ-Fit® filtration units, 3 units, pkg of 3 unit

EZFITMHTA3

EZ-Fit® Manifold Filtration Head

application(s)

pharmaceutical

application(s)

bioburden testing
food and beverages
industrial hygiene
industrial qc
pharmaceutical
water monitoring

application(s)

pharmaceutical

application(s)

-

packaging

pkg of 1 unit

packaging

pkg of 1 unit

packaging

pkg of 1 unit

packaging

pkg of 3 unit

material

316L stainless steel

material

stainless steel

material

316L stainless steel

material

316L stainless steel

sterilization compatibility

autoclavable compatible

sterilization compatibility

autoclavable compatible

sterilization compatibility

autoclavable compatible

sterilization compatibility

autoclavable compatible

manufacturer/tradename

EZ-Fit®

manufacturer/tradename

EZ-Fit®

manufacturer/tradename

EZ-Fit®

manufacturer/tradename

EZ-Fit®

Biochem/physiol Actions

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.

Features and Benefits

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.

Linkage

More potent, but more toxic, than methotrexate.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000361224
0000361224
0000389737
0000369110
0000335545

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Min Zhang et al.
Cell, 181(3), 637-652 (2020-04-10)
Many cytosolic proteins lacking a signal peptide, called leaderless cargoes, are secreted through unconventional secretion. Vesicle trafficking is a major pathway involved. It is unclear how leaderless cargoes enter into the vesicle. Here, we find a translocation pathway regulating vesicle
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
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
Steven M Horwitz et al.
Blood, 119(18), 4115-4122 (2012-03-08)
Systemic treatment for cutaneous T-cell lymphoma (CTCL) involves the use of less aggressive, well-tolerated therapies. Pralatrexate is a novel antifolate with high affinity for reduced folate carrier-1. A dose de-escalation strategy identified recommended pralatrexate dosing for patients with CTCL that
Yingjuan J Lu et al.
Cell reports. Medicine, 2(10), 100422-100422 (2021-11-11)
Provoked by sterile/nonsterile insults, prolonged monocyte mobilization and uncontrolled monocyte/macrophage activation can pose imminent or impending harm to the affected organs. Curiously, folate receptor beta (FRβ), with subnanomolar affinity for the vitamin folic acid (FA), is upregulated during immune activation
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