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F3503

Sigma-Aldrich

5-Fluoro-2′-deoxyuridine 5′-monophosphate sodium salt

~85%

Sinonimo/i:

FdUMP

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About This Item

Formula empirica (notazione di Hill):
C9H12FN2O8P
Numero CAS:
103226-10-4
Peso molecolare:
326.17
Numero MDL:
MFCD00057409
Codice UNSPSC:
41106305
ID PubChem:
24894845
NACRES:
NA.51

Saggio

~85%

Forma fisica

solid

Temperatura di conservazione

−20°C

Stringa SMILE

[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);;
DGEOOGBABXVZPJ-UHFFFAOYSA-N

Descrizione generale

5- 5-fluoro-2′-deoxyuridylate (FdUMP) is an intracellularly generated metabolite of 5-Fluorouracil (5-FU), a widely used reagent in molecular biology to study DNA synthesis and metabolism.

Applicazioni

It has been used:

  • as an anti-mitotic agent for culturing mouse primary cortical neurons.
  • as a component of feeding media in the culturing of mouse primary cortical neurons.
  • in studies on the activity and function of thymidylate synthase (TS).

Azioni biochim/fisiol

5-Fluoro-2′-deoxyuridine 5′-monophosphate sodium salt (FdUMP) is an DNA synthesis inhibitor. FdUMP along with RNA synthesis inhibitor 3′-C-ethinylcytidine induces cell death in cervical cancer cells at nanomolar concentrations.

Pittogrammi

Health hazardExclamation mark
GHS08,GHS07

Avvertenze

Warning

Indicazioni di pericolo

H302 + H312 + H332,H351

Classi di pericolo

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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

Certificati d'analisi (COA)

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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)
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
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
Paul J Sapienza et al.
Biochemistry, 58(30), 3302-3313 (2019-07-10)
Thymidylate synthase (TS) is a dimeric enzyme conserved in all life forms that exhibits the allosteric feature of half-the-sites activity. Neither the reason for nor the mechanism of this phenomenon is understood. We used a combined nuclear magnetic resonance (NMR)
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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