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F3503

Sigma-Aldrich

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

~85%

Synonym(s):

FdUMP

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About This Item

Empirical Formula (Hill Notation):
C9H12FN2O8P
CAS Number:
103226-10-4
Molecular Weight:
326.17
MDL number:
MFCD00057409
UNSPSC Code:
41106305
PubChem Substance ID:
24894845
NACRES:
NA.51

Assay

~85%

Quality Level

200

form

solid

storage temp.

−20°C

SMILES string

[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

General description

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.

Application

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).

Biochem/physiol Actions

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.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332,H351

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

F3503-BULK:
F3503-5MG:
F3503-VAR:
F3503-25MG:
F3503-1MG:

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Certificates of Analysis (COA)

Lot/Batch Number
075K7015
015K7021
126H7838
129F7125
124H7837

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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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