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Merck

A5159

Aminopterin

Hybri-Max, 50 ×, γ-irradiated, lyophilized powder, BioXtra, suitable for hybridoma

Synonim(y):

(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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Informacje o tej pozycji

Wzór empiryczny (zapis Hilla):
C19H20N8O5
Numer CAS:
Masa cząsteczkowa:
440.41
PubChem Substance ID:
UNSPSC Code:
12352205
MDL number:
NACRES:
NA.75
EC Number:
200-209-9
Beilstein/REAXYS Number:
69045
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InChI key

TVZGACDUOSZQKY-LBPRGKRZSA-N

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

SMILES string

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

biological source

synthetic

grade

Hybri-Max

sterility

γ-irradiated

product line

BioXtra

form

lyophilized powder

concentration

50 ×

technique(s)

cell culture | hybridoma: suitable

impurities

endotoxin, tested

solubility

10 mL/vial, clear, red (in TC Medium)

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

Quality Level

Gene Information

human ... FPGS(2356)
mouse ... Fpgs(14287)

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Application

Aminopterin concentrate supplement for hybridoma cell culture applications.

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.

Preparation Note

Reconstitute contents of vial with 10 mL sterile cell culture medium. Stock solution is sufficient to prepare 500 mL medium. Final working concentration: 0.4 μM aminopterin.

Other Notes

More potent, but more toxic, than methotrexate.

Legal Information

Hybri-Max is a trademark of Sigma-Aldrich Co. LLC
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pictograms

Skull and crossbonesHealth hazard

signalword

Danger

Hazard Classifications

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

Klasa składowania

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


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Dokumenty związane z niedawno zakupionymi produktami zostały zamieszczone w Bibliotece dokumentów.

Odwiedź Bibliotekę dokumentów

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
A Rosowsky
Current medicinal chemistry, 6(4), 329-352 (1999-04-02)
Nonpolyglutamatable antifolates are potentially of therapeutic interest for the treatment of tumors that are inherently refractory, or have become resistant, to classical antifolates as a result of decreased expression of the enzyme folylpolyglutamate synthetase. An interesting class of water-soluble nonpolyglutamatable
Sara C Hyoun et al.
Birth defects research. Part A, Clinical and molecular teratology, 94(4), 187-207 (2012-03-22)
Methotrexate and aminopterin are folic acid antagonists that inhibit dihydrofolate reductase, resulting in a block in the synthesis of thymidine and inhibition of DNA synthesis. Methotrexate has been used for the treatment of malignancy, rheumatic disorders, and psoriasis and termination
Alan Menter et al.
The Journal of pharmacology and experimental therapeutics, 342(3), 696-708 (2012-06-02)
N-[4-[[(2,4-diamino-6-pterdinyl)methyl]amino]benzoyl]-L/D-glutamic acid (L/D-AMT) is an investigational drug in phase 1 clinical development that consists of the L-and D-enantiomers of aminopterin (AMT). L/D-AMT is obtained from a novel process for making the L-enantiomer (L-AMT), a potent oral antiinflammatory agent. The purpose
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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