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Merck
CN

A1784

氨基蝶呤

synthetic (organic), ≥97% (TLC), dihydrofolate reductase inhibitor, powder

别名:

4-氨基-PGA, 4-氨基叶酸, N-[4-[[(2,4-二氨基-6-蝶啶)甲基]氨基]苯甲酰]-L-谷氨酸, （S）-2- {4 - [（2,4-二氨基胍-6-基）甲氨基]苯甲酰氨基}戊二酸

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关于此项目

经验公式（希尔记法）:
C19H20N8O5
化学文摘社编号:
54-62-6
分子量:
440.41
MDL number:
MFCD00036692
UNSPSC Code:
12352200
PubChem Substance ID:
24278186
NACRES:
NA.77
EC Number:
200-209-9
Beilstein/REAXYS Number:
69045

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产品名称

氨基蝶呤, powder

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

biological source

synthetic (organic)

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

Quality Level

200

Gene Information

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

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相关类别

Biochem/physiol Actions

与二氢叶酸还原酶结合并抑制其活性的叶酸拮抗剂。
叶酸拮抗剂。氨基蝶呤是由叶酸转运蛋白运输至细胞内的。在细胞内，它被叶酰聚谷氨酸合酶转化为一种高分子量的聚谷氨酸盐代谢物，该产物又与二氢叶酸还原酶结合并抑制其活性。氨基蝶呤-聚谷氨酸盐经 γ-谷氨酰基水解酶作用发生细胞内降解。

Features and Benefits

这种化合物是凋亡研究的特色产品。点击此处发现更多特色凋亡产品。在sigma.com/discover-bsm可了解更多关于生物活性小分子的其他研究领域。

Other Notes

比甲氨喋呤更有效，但毒性也更强。

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

存储类别

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

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000490219
0000490219
0000490215
0000490215
0000473802

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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
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
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
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