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Merck
CN

F3503

Sigma-Aldrich

5-氟-2′-脱氧尿苷 5′-单磷酸盐 钠盐

~85%

别名:

FdUMP

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About This Item

经验公式(希尔记法):
C9H12FN2O8P
分子量:
326.17
MDL编号:
UNSPSC代码:
41106305
PubChem化学物质编号:
NACRES:
NA.51

方案

~85%

质量水平

表单

solid

储存温度

−20°C

SMILES字符串

[Na].OC1CC(OC1COP(O)(O)=O)N2C=C(F)C(=O)NC2=O

InChI

1S/C9H12FN2O8P.Na.H/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18;;/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18);;

InChI key

DGEOOGBABXVZPJ-UHFFFAOYSA-N

相关类别

一般描述

5- 5-氟-2′-脱氧尿苷(FdUMP)是胞内生成的5-氟尿嘧啶(5-FU)的代谢产物,5-氟尿嘧啶是一种在分子生物学中应用广泛的试剂,用于研究DNA合成和代谢。

应用

它已被用于:

  • 作为抗有丝分裂剂用于培养小鼠原代皮层神经元(primary cortical neuron)。
  • 作为培养基成分用于培养小鼠原代皮层神经元。
  • 用于胸苷酸合成酶(TS)活性和功能的研究。

生化/生理作用

5-氟-2′-脱氧尿苷-5′-单磷酸盐(FdUMP)是一种 DNA 合成抑制剂。FdUMP 与 RNA 合成抑制剂 3′-C-ethinylcytidine 一起在纳摩尔浓度下诱导宫颈癌细胞死亡。

象形图

Health hazardExclamation mark

警示用语:

Warning

危险分类

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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访问文档库

Induction of apoptosis in cervical cancer cells by the duplex drug 5-FdU--ECyd, coupling 2?-deoxy-5-fluorouridine and 3?-C-ethinylcytidine
Schott S and Bruning A
Gynecologic Oncology, 135(2), 342-348 (2014)
Yoshihiro Nabeya et al.
Cancer science, 102(8), 1509-1515 (2011-05-13)
Thymidylate synthase (TS) plays a major role in the response to 5-fluorouracil (5-FU) by binding directly to the 5-FU metabolite, 5-fluoro-dUMP (FdUMP). The change in the TS expression levels after 5-FU administration was examined in parallel to 5-FU responsiveness in
W H Gmeiner
Current medicinal chemistry, 12(2), 191-202 (2005-01-11)
Thymidylate synthase (TS) is a well-validated target for cancer chemotherapy. TS was established as the principal target of the widely used anticancer drug 5-fluorouracil (5FU). The 5FU metabolite FdUMP forms a covalent complex with TS that is stabilized by 5-formyl
Adam Jarmuła et al.
Bioorganic & medicinal chemistry letters, 18(8), 2701-2708 (2008-03-26)
Molecular dynamics simulations and free energy calculations are presented, exploring previously described experimentally studied interactions of a series of 2'-fluoro-substituted dUMP/FdUMP analogues with thymidylate synthase (TS). The results show the inhibitory behaviors of 2'-F-ara-UMP, 2',2''-diF-dUMP and 2',5-diF-ara-UMP to be dependent
Manee Chanama et al.
Molecular biology reports, 38(2), 1029-1037 (2010-06-26)
Thymidylate synthase (TS) of Plasmodium dihydrofolate reductase-thymidylate synthase (DHFR-TS) functions as a homodimeric enzyme with two active sites located near the subunit interface. The dimerization is essential for catalysis, since the active site of each subunit contains amino acid residues

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