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HomeProduct name list2'-Deoxyuridine

2'-Deoxyuridine

Synonym(s):1-(2-Deoxy-β-D-ribofuranosyl)uracil;Uracil deoxyriboside

  • CAS NO.:951-78-0
  • Empirical Formula: C9H12N2O5
  • Molecular Weight: 228.2
  • MDL number: MFCD00006527
  • EINECS: 213-455-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-09 19:38:33
2'-Deoxyuridine Structural

What is 2'-Deoxyuridine?

Description

2'-Deoxyuridine is an intermediate in the synthesis of thymidylate, which is a precursor for DNA synthesis. It has been shown to inhibit the enzymatic activity of enzymes responsible for synthesizing uridine and thymidylate, leading to neuronal death. 2'-Deoxyuridine has been used as a fluorescence probe for nucleic acids and as a polymerase chain reaction (PCR) substrate. It is also known to bind with toll-like receptor 4 (TLR4), which is involved in inflammatory responses.

Chemical properties

White crystalline powder

The Uses of 2'-Deoxyuridine

An uridine derivative as therapeutic agent for treating allergy, cancer, infection and autoimmune disease

The Uses of 2'-Deoxyuridine

2'-Deoxyuridine is frequently halogenated to create thymidine analogues useful for studies of DNA synthesis and degradation mechanisms. Derivatized 2'-Deoxyuridines used as labeling substrates include chloro-2'-deoxyuridine (CldU), bromodeoxyuridine (BrdU) and/or iododeoxyuridine (IdU). Other useful analogues of 2'-deoxyuridine include 5-ethynyl-2'-deoxyuridine (DdU) and 5-hydroxymethyl-2'-deoxyuridine (HmdU). Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies. Deoxyuridine (dU) is used to indirectly determine if there are sufficient levels of folate and cobalamin in cell or tissue samples.

Definition

ChEBI: 2'-deoxyuridine is a pyrimidine 2'-deoxyribonucleoside having uracil as the nucleobase. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a uracil.

Biological Activity

2'-deoxyuridine is frequently halogenated to create thymidine analogues useful for studies of dna synthesis and degradation mechanisms.

Properties of 2'-Deoxyuridine

Melting point: 167-169 °C(lit.)
Boiling point: 370.01°C (rough estimate)
alpha  D22 +50° (c = 1.1 in N NaOH)
Density  1.3705 (rough estimate)
refractive index  52 ° (C=1, 1mol/L NaOH)
storage temp.  Inert atmosphere,2-8°C
solubility  DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)
form  Powder
pka pKa 9.3(H2O t = 25) (Uncertain)
color  White to off-white
Water Solubility  300 g/L (20 ºC)
Sensitive  Air Sensitive
Merck  14,2910
BRN  24433
CAS DataBase Reference 951-78-0(CAS DataBase Reference)
EPA Substance Registry System Uridine, 2'-deoxy- (951-78-0)

Safety information for 2'-Deoxyuridine

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 2'-Deoxyuridine

InChIKey MXHRCPNRJAMMIM-ATRFCDNQSA-N

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