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D3876

Sigma-Aldrich

2′-Deoxyuridine 5′-monophosphate disodium salt

Sigma Grade

Synonym(e):

dUMP

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About This Item

Lineare Formel:
C9H11N2O8PNa2
CAS-Nummer:
42155-08-8
Molekulargewicht:
352.15
EG-Nummer:
255-687-1
MDL-Nummer:
MFCD00065282
UNSPSC-Code:
41106305
PubChem Substanz-ID:
24893787
NACRES:
NA.51

Biologische Quelle

synthetic (organic)

Qualitätsniveau

200

Qualität

Sigma Grade

Assay

≥98% (HPLC)

Form

powder

Lagertemp.

−20°C

SMILES String

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

InChI

1S/C9H13N2O8P.Na.H/c12-5-3-8(11-2-1-7(13)10-9(11)14)19-6(5)4-18-20(15,16)17;;/h1-2,5-6,8,12H,3-4H2,(H,10,13,14)(H2,15,16,17);;

InChIKey

WXIVKKBDJOCRNB-UHFFFAOYSA-N

Allgemeine Beschreibung

2′-Deoxyuridine 5′-monophosphate disodium salt (dUMP) is a substrate for thymidylate synthase and is converted to deoxythymidine monophosphate (dTMP).

Anwendung

2′-Deoxyuridine 5′-monophosphate (dUMP) is used by the enzyme thymidylate synthetase (TS) (EC 2.1.1.45) for the de novo production of dTMP. dUMP is used as the reference substrate in studies of dUMP analogues in potential chemotherapy applications.
2′-Deoxyuridine 5′-monophosphate disodium salt has been used:
  • in ultraperformance liquid chromatography-tandem mass spectrometry (UPLC/MS/MS) assay
  • to stimulate proliferation of peripheral blood mononuclear cell (PBMCs) exposed to influenza virus antigen
  • in thymidylate synthase activity assay Helicobacter pylori

Biochem./physiol. Wirkung

2′-Deoxyuridine 5′-monophosphate disodium salt (dUMP) conversion to pyrimidine is inhibited by methotrexate. The inhibition of dUMP to deoxythymidine monophosphate (dTMP) at the methylation step is a key in controlling bacterial and eukaryotic cell growth.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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Eric M Koehn et al.
Nature, 458(7240), 919-923 (2009-04-17)
Biosynthesis of the DNA base thymine depends on activity of the enzyme thymidylate synthase to catalyse the methylation of the uracil moiety of 2'-deoxyuridine-5'-monophosphate. All known thymidylate synthases rely on an active site residue of the enzyme to activate 2'-deoxyuridine-5'-monophosphate.
Adam Jarmuła et al.
Bioorganic & medicinal chemistry, 15(6), 2346-2358 (2007-02-06)
Thymidylate synthase (TS) is a target enzyme for a number of anticancer agents including the 5-fluorouracil metabolite, FdUMP. The present paper reports on molecular modeling studies of the effect of substitution at C(5) position in the pyrimidine ring of the
Xiaoli Zhang et al.
Protein and peptide letters, 19(11), 1225-1230 (2012-04-20)
ThyX, a flavin-dependent thymidylate synthase that is involved in the synthesis of dTMP from dUMP, is a promising target for the development of novel antibacterial drugs that aimed at blocking the biosynthesis of dTMP, one of the building blocks of
Abalo Chango et al.
Medical principles and practice : international journal of the Kuwait University, Health Science Centre, 18(2), 81-84 (2009-02-11)
To develop a method for the simultaneous measurement of 5-methylcytosine (5-metC) and 2'-deoxyuridine monophosphate (dU). Genomic DNA was extracted from the HepG2 cell line grown in experimental complete medium or in folate-depleted medium. Samples were treated with RNAse A and
Peter S Ludwig et al.
European journal of medicinal chemistry, 40(5), 494-504 (2005-05-17)
Amphiphilic anticancer prodrugs of 5'-fluoro-2'-deoxyuridine-5'-monophosphate (5-FdUMP) were synthesized according to the hydrogen phosphonate method by coupling lipophilic cytosine derivatives or a phospholipid with 5-fluoro-2'-deoxyuridine (5-FdU). Studies within the in vitro Anticancer Screen Program of the National Cancer Institute have demonstrated
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