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D5412

Sigma-Aldrich

2′-Deoxyuridine

≥98.5%

Synonyme(s) :

1-(2-Deoxy-β-D-ribofuranosyl)uracil, Uracil deoxyriboside

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About This Item

Formule empirique (notation de Hill):
C9H12N2O5
Numéro CAS:
951-78-0
Poids moléculaire :
228.20
Numéro Beilstein :
24433
Numéro CE :
213-455-7
Numéro MDL:
MFCD00006527
Code UNSPSC :
41106305
ID de substance PubChem :
24893831
Nomenclature NACRES :
NA.51

Source biologique

synthetic (organic)

Pureté

≥98.5%

Forme

powder

Impuretés

Thymidine, free

Solubilité

water: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

Chaîne SMILES 

OC[C@H]1O[C@H](C[C@@H]1O)N2C=CC(=O)NC2=O

InChI

1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1

Clé InChI

MXHRCPNRJAMMIM-SHYZEUOFSA-N

Informations sur le gène

mouse ... Slc29a1(63959)

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Catégories apparentées

Application

2′-Deoxyuridine has been used as a:
  • precursor of [3H]thymidine triphosphate (TTP) in place of thymidine to avoid a potential thymidine block in relative proliferation assays
  • nucleoside supplement for cell cycle synchronization and DNA replication inhibition
  • mitotic inhibitor in culture media to minimize the proliferation of glial cells

Actions biochimiques/physiologiques

2′-Deoxyuridine (dU) is frequently halogenated to create thymidine analogs 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 analogs of 2′-deoxyuridine include 5-ethynyl-2′-deoxyuridine (DdU) and 5-hydroxymethyl-2′-deoxyuridine (HmdU).

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Yang Yang et al.
Cancer letters, 453, 170-183 (2019-04-08)
Overexpression of NQO1 is associated with poor prognosis in human cancers including lung, stomach, colon, cervical, and pancreatic cancers. However, the molecular mechanisms underlying the protumorigenic capacities of NQO1 have not been fully elucidated. Here, we investigated this question and
Gabriel Robert et al.
Chemical research in toxicology, 33(2), 565-575 (2019-12-11)
The reaction of hydroxyl radical (HO•) with thymine in DNA generates 5-(uracilyl)-methyl radicals (T•) and the corresponding methylperoxyl radical (TOO•) in the presence of O2, which in turn propagates damage by reacting with a vicinal nucleobase. This leads to so-called
Yingqiao Wang et al.
ACS nano, 15(9), 14662-14671 (2021-08-26)
Understanding cellular electrical communications in both health and disease necessitates precise subcellular electrophysiological modulation. Nanomaterial-assisted photothermal stimulation was demonstrated to modulate cellular activity with high spatiotemporal resolution. Ideal candidates for such an application are expected to have high absorbance at
Kaori Nomura-Komoike et al.
Scientific reports, 10(1), 1488-1488 (2020-02-01)
Müller glia, the principal glial cell type in the retina, have the potential to reenter the cell cycle after retinal injury. In mammals, proliferation of Müller glia is followed by gliosis, but not regeneration of neurons. Retinal injury is also
Quan-Liang Jian et al.
PeerJ, 6, e5739-e5739 (2018-10-09)
Both age and intensive exercise are generally considered critical risk factors for osteoarthritis. In this work, we intend to establish zebrafish models to assess the role of these two factors on cartilage homeostasis. We designed a swimming device for zebrafish
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