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A5159

Aminopterin

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

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
PubChem Substance ID:
24890950
UNSPSC Code:
12352205
MDL number:
MFCD00036692
NACRES:
NA.75
EC Number:
200-209-9
Beilstein/REAXYS Number:
69045
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biological source

synthetic

Quality Level

200

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

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)

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
GHS06,GHS08

signalword

Danger

Hazard Classifications

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

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number
SLCL0719
SLCD6037
SLBZ0306
SLBV1691
SLBS4237

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Hatem A Azim et al.
Current opinion in oncology, 24(3), 325-331 (2012-02-22)
To discuss the clinical development of new formulations of old cytotoxic agents and highlight the value of adopting this strategy. Several drugs are currently in clinical development with high potential in improving clinical outcomes compared with their older counterparts. We
Edward C Keystone et al.
The Journal of rheumatology, 38(9), 1875-1883 (2011-07-05)
To investigate the potential efficacy, safety, and tolerability of daily use of CH-1504 in patients with active rheumatoid arthritis (RA). US National Institutes of Health database no. NCT00658047. In our phase II randomized double-blind double-dummy study, patients naive to methotrexate
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
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Global Trade Item Number

SKUGTIN
A5159-10VL04061833375518