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Merck

D5412

2′-Deoxyuridine

≥98.5%, synthetic (organic), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C9H12N2O5
CAS Number:
951-78-0
Molecular Weight:
228.20
NACRES:
NA.51
PubChem Substance ID:
24893831
UNSPSC Code:
41106305
EC Number:
213-455-7
MDL number:
MFCD00006527
Beilstein/REAXYS Number:
24433

Key Documents

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Product Name

2′-Deoxyuridine, ≥98.5%

InChI key

MXHRCPNRJAMMIM-SHYZEUOFSA-N

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

SMILES string

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

biological source

synthetic (organic)

assay

≥98.5%

form

powder

impurities

Thymidine, free

solubility

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

Quality Level

300

Gene Information

mouse ... Slc29a1(63959)

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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

Biochem/physiol Actions

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).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG7457
BCCF6690
MKCH0558
MKBX4641V
MKBS0349V

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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
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
Hiroyuki Yamakoshi et al.
Journal of the American Chemical Society, 134(51), 20681-20689 (2012-12-04)
Alkyne has a unique Raman band that does not overlap with Raman scattering from any endogenous molecule in live cells. Here, we show that alkyne-tag Raman imaging (ATRI) is a promising approach for visualizing nonimmobilized small molecules in live cells.
Hongxiu Ning et al.
Cytotherapy, 15(1), 57-63 (2012-12-25)
Thymidine analog 5-ethynyl-2-deoxyuridine (EdU) has recently been used for tracking mesenchymal stem cells (MSCs). In the present study, we tested whether EdU was cytotoxic and whether it interfered with differentiation, cytokine secretion and migration of MSCs. EdU labeling was performed
Shao-yu Wu et al.
Nucleic acids research, 41(8), 4650-4659 (2013-03-02)
Therapeutic small interfering RNAs (siRNAs) are composed of chemically modified nucleotides, which enhance RNA stability and increase affinity in Watson-Crick base pairing. However, the precise fate of such modified nucleotides once the siRNA is degraded within the cell is unknown.
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