Compounds > propynyloxy-2'-deoxyuridine
Page last updated: 2024-12-07

propynyloxy-2'-deoxyuridine

Description

Propynyloxy-2'-deoxyuridine, also known as EdU (5-ethynyl-2'-deoxyuridine), is a synthetic nucleoside analog that is widely used as a thymidine analog for click chemistry-based cell proliferation assays. It is incorporated into the DNA of dividing cells during S-phase. After incorporation, the alkyne group of EdU can be specifically detected by reaction with an azide-containing fluorescent dye through a copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, known as the click reaction. This allows for the visualization and quantification of cell proliferation and DNA replication. EdU has several advantages over other thymidine analogs, including higher sensitivity, better cell permeability, and lower toxicity. It has been successfully used in various biological studies, such as cell cycle analysis, stem cell research, tumor growth studies, and developmental biology. The study of EdU is crucial for understanding cell proliferation and its role in various biological processes.'

propynyloxy-2'-deoxyuridine: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID99692
CHEMBL ID3143044
SCHEMBL ID1417668
MeSH IDM0065832

Synonyms (15)

Synonym
5-propynyloxy-durd
1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-prop-2-ynoxy-pyrimidine-2,4-dione
65367-85-3
uridine, 2'-deoxy-5-(2-propynyloxy)-
propynyloxy-2'-deoxyuridine
1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-prop-2-ynoxypyrimidine-2,4-dione
nsc 267459
SCHEMBL1417668
2'-deoxy-5-propargyloxyuridine
CHEMBL3143044
2'-deoxy-5-(2-propynyloxy)uridine
5-(propargyloxy)-2'-deoxyuridine
1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(prop-2-ynyloxy)pyrimidine-2,4(1h,3h)-dione
1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(prop-2-yn-1-yloxy)pyrimidine-2,4(1h,3h)-dione
1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(prop-2-yn-1-yloxy)-1,2,3,4-tetrahydropyrimidine-2,4-dione
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID156399Compound was evaluated for antiviral activity in rabbit kidney cells infected with vaccinia virus1981Journal of medicinal chemistry, Apr, Volume: 24, Issue:4
Synthesis and antiviral activity of 5-[(cyanomethylene)oxy]-2'-deoxyuridine.
AID1135601Cytotoxicity against mouse L cells assessed as suppression of replication at 10'-3 M1978Journal of medicinal chemistry, Feb, Volume: 21, Issue:2
5-O-Alkylated derivatives of 5-hydroxy-2'-deoxyuridine as potential antiviral agents. Anti-herpes activity of 5-propynyloxy-2'-deoxyuridine.
AID1135598Antiviral activity against Herpes simplex virus 1 KOS infected in human skin fibroblasts primed with interferon and superinduced with cyclohexamide and actinomycin D assessed as inhibition of virus-induced cytopathogenicity1978Journal of medicinal chemistry, Feb, Volume: 21, Issue:2
5-O-Alkylated derivatives of 5-hydroxy-2'-deoxyuridine as potential antiviral agents. Anti-herpes activity of 5-propynyloxy-2'-deoxyuridine.
AID1135603Antiviral activity against Vesicular stomatitis virus infected in human skin fibroblasts primed with interferon and superinduced with cyclohexamide and actinomycin D assessed as inhibition of virus-induced cytopathogenicity1978Journal of medicinal chemistry, Feb, Volume: 21, Issue:2
5-O-Alkylated derivatives of 5-hydroxy-2'-deoxyuridine as potential antiviral agents. Anti-herpes activity of 5-propynyloxy-2'-deoxyuridine.
AID1135597Antiviral activity against Herpes simplex virus 1 KOS infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity1978Journal of medicinal chemistry, Feb, Volume: 21, Issue:2
5-O-Alkylated derivatives of 5-hydroxy-2'-deoxyuridine as potential antiviral agents. Anti-herpes activity of 5-propynyloxy-2'-deoxyuridine.
AID156521Concentration required to reduce HSV-1(KOS) induced cytopathogenicity by 50% was measured1981Journal of medicinal chemistry, Apr, Volume: 24, Issue:4
Synthesis and antiviral activity of 5-[(cyanomethylene)oxy]-2'-deoxyuridine.
AID1135599Antiviral activity against Vesicular stomatitis virus infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity1978Journal of medicinal chemistry, Feb, Volume: 21, Issue:2
5-O-Alkylated derivatives of 5-hydroxy-2'-deoxyuridine as potential antiviral agents. Anti-herpes activity of 5-propynyloxy-2'-deoxyuridine.
AID156522Concentration required to reduce HSV-1(KOS) induced cytopathogenicity by 50% was measured by the addition of [1,'2'-3H]dUrd1981Journal of medicinal chemistry, Apr, Volume: 24, Issue:4
Synthesis and antiviral activity of 5-[(cyanomethylene)oxy]-2'-deoxyuridine.
AID1135602Ratio of I50 for DNA synthesis in primary rabbit kidney cells by [3H]-dT incorporation assay to MIC50 for Herpes simplex virus 1 KOS1978Journal of medicinal chemistry, Feb, Volume: 21, Issue:2
5-O-Alkylated derivatives of 5-hydroxy-2'-deoxyuridine as potential antiviral agents. Anti-herpes activity of 5-propynyloxy-2'-deoxyuridine.
AID1135596Antiviral activity against Vaccinia virus infected in human skin fibroblasts primed with interferon and superinduced with cyclohexamide and actinomycin D assessed as inhibition of virus-induced cytopathogenicity1978Journal of medicinal chemistry, Feb, Volume: 21, Issue:2
5-O-Alkylated derivatives of 5-hydroxy-2'-deoxyuridine as potential antiviral agents. Anti-herpes activity of 5-propynyloxy-2'-deoxyuridine.
AID156523Concentration required to reduce HSV-1(KOS) induced cytopathogenicity by 50% was measured by the addition of [Me-3H]-dThd1981Journal of medicinal chemistry, Apr, Volume: 24, Issue:4
Synthesis and antiviral activity of 5-[(cyanomethylene)oxy]-2'-deoxyuridine.
AID156515Concentration required to inhibit incorporation of [Me-3H]-dThd into DNA of primary rabbit kidney (PRK) cells by 50%1981Journal of medicinal chemistry, Apr, Volume: 24, Issue:4
Synthesis and antiviral activity of 5-[(cyanomethylene)oxy]-2'-deoxyuridine.
AID156530Concentration required to reduce HSV-2 induced cytopathogenicity by 50% in primary rabbit kidney (PRK) cells; 7-401981Journal of medicinal chemistry, Apr, Volume: 24, Issue:4
Synthesis and antiviral activity of 5-[(cyanomethylene)oxy]-2'-deoxyuridine.
AID156531Concentration required to reduce TK-HSV-1 (B2006) induced cytopathogenicity by 50% in primary rabbit kidney (PRK) cells1981Journal of medicinal chemistry, Apr, Volume: 24, Issue:4
Synthesis and antiviral activity of 5-[(cyanomethylene)oxy]-2'-deoxyuridine.
AID156517Concentration required to reduce HSV-1 induced cytopathogenicity by 50% in primary rabbit kidney (PRK) cells; 1-1.51981Journal of medicinal chemistry, Apr, Volume: 24, Issue:4
Synthesis and antiviral activity of 5-[(cyanomethylene)oxy]-2'-deoxyuridine.
AID1135595Antiviral activity against Vaccinia virus infected in primary rabbit kidney cells assessed as inhibition of virus-induced cytopathogenicity1978Journal of medicinal chemistry, Feb, Volume: 21, Issue:2
5-O-Alkylated derivatives of 5-hydroxy-2'-deoxyuridine as potential antiviral agents. Anti-herpes activity of 5-propynyloxy-2'-deoxyuridine.
AID156400Concentration required to inhibit incorporation of [1,'2'-3H]dUrd into DNA of primary rabbit kidney (PRK) cells by 50%1981Journal of medicinal chemistry, Apr, Volume: 24, Issue:4
Synthesis and antiviral activity of 5-[(cyanomethylene)oxy]-2'-deoxyuridine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (40.00)18.7374
1990's2 (40.00)18.2507
2000's1 (20.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.46

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.46 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.25 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.46)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
ethylene glycol
Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.		1.9910ethanediol;
glycol		metabolite;
mouse metabolite;
solvent;
toxin
pargyline
Pargyline: A monoamine oxidase inhibitor with antihypertensive properties.		2.0110aromatic amine
floxuridine
Floxuridine: An antineoplastic antimetabolite that is metabolized to fluorouracil when administered by rapid injection; when administered by slow, continuous, intra-arterial infusion, it is converted to floxuridine monophosphate. It has been used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.. floxuridine : A pyrimidine 2'-deoxyribonucleoside compound having 5-fluorouracil as the nucleobase; used to treat hepatic metastases of gastrointestinal adenocarcinomas and for palliation in malignant neoplasms of the liver and gastrointestinal tract.		1.9610nucleoside analogue;
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
radiosensitizing agent
idoxuridine
[no description available]		2.3620organoiodine compound;
pyrimidine 2'-deoxyribonucleoside		antiviral drug;
DNA synthesis inhibitor
methyl red
methyl red: RN given refers to parent cpd; structure. methyl red : An azo dye consisting of benzoic acid substituted at position 2 by a 4-[(dimethylamino)phenyl]diazenyl group.		2.0110
deoxyuridine
[no description available]		7.940pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
fluorescein
Fluorescein: A phthalic indicator dye that appears yellow-green in normal tear film and bright green in a more alkaline medium such as the aqueous humor.. fluorescein (lactone form) : A xanthene dye that is highly fluorescent, detectable even when present in minute quantities. Used forensically to detect traces of blood, in analytical chemistry as an indicator in silver nitrate titrations and in microscopy.		2.01102-benzofurans;
gamma-lactone;
organic heteropentacyclic compound;
oxaspiro compound;
polyphenol;
xanthene dye		fluorescent dye;
radioopaque medium
vidarabine
adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.		2.3620beta-D-arabinoside;
purine nucleoside		antineoplastic agent;
bacterial metabolite;
nucleoside antibiotic
5-hydroxy-2'-deoxyuridine
5-hydroxy-2'-deoxyuridine: a major oxidation product of 2'-deoxycytidine		6.9510
propargylamine
propargylamine: RN given refers to parent cpd; structure		2.0110
5-cyano-2'-deoxyuridine
5-cyano-2'-deoxyuridine: structure in first source		1.9610
deoxyribose
[no description available]		1.9910deoxypentosehuman metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
oligonucleotides
[no description available]		2.4120
ConditionIndicatedRelationship StrengthStudiesTrials
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