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B0631

Sigma-Aldrich

5-Bromo-2′-deoxyuridine 5′-triphosphate sodium salt

≥90%

Synonym(s):

5-BrdUTP

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About This Item

Empirical Formula (Hill Notation):
C9H14BrN2O14P3
CAS Number:
Molecular Weight:
547.04
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic (organic)

assay

≥90%

form

powder

solubility

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

storage temp.

−20°C

SMILES string

[Na].OC1CC(OC1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N2C=C(Br)C(=O)NC2=O

InChI

1S/C9H14BrN2O14P3.Na.H/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(24-7)3-23-28(19,20)26-29(21,22)25-27(16,17)18;;/h2,5-7,13H,1,3H2,(H,19,20)(H,21,22)(H,11,14,15)(H2,16,17,18);;

InChI key

UWZGQOWZUSBZMC-UHFFFAOYSA-N

Related Categories

General description

5-Bromo-2′-deoxyuridine 5′-triphosphate is used for incorporation into DNA for studying normal and tumor cell proliferation profiles.

Application

5-Bromo-2′-deoxyuridine 5′-triphosphate (5-BrdUTP) may be used as a labeling TdT substrate for terminal deoxynucleotidyl transferase (TdT) reactions or for DNA synthesis. BrdUTP is also used as an effective mutagenic agent. 5-BrdUTP labeling may be detected by immunological techniques or 5-BrdUTP may be derivitized by biotinylation or other methods for detection by fluorogenic or chromogenic methods.
5-Bromo-2′-deoxyuridine 5′-triphosphate sodium salt has been used:
  • in the labelling of 3′-OH termini of fragmented DNA with double stranded breaks in african green monkey kidney cells
  • to label cleaved DNA ends in apoptosis assay in avian tissue sections
  • for incorporation into mice prostates for immunohistochemistry studies

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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Visualization of heavy ion tracks by labeling 3'-OH termini of induced DNA strand breaks
Konishi T, et al.
Journal of Radiation Research, 52(4), 433-440 (2011)
Effect of 5-fluoro-2?-deoxyuridine (FdUrd) on 5-bromo-2?-deoxyuridine (BrdUrd) incorporation into DNA, measured with a monoclonal BrdUrd antibody and by the BrdUrd/hoechst quenching effect
Ellwart J and Dormer P
Cytometry, 6(6), 513-520 (1985)
Xiangdong Ma et al.
Molecular biology reports, 35(4), 663-667 (2007-09-18)
To explore the mutagenic properties of the nucleotide analogue bromodeoxyuridine triphosphate (BrdUTP), the wild type alpha-amylase (xamy) gene from Xanthomonas campestris pv. campestris 8004 was used as a mutational target. It was mutated using PCR techniques to partially replace deoxythymidine
Zbigniew Darzynkiewicz et al.
Methods in molecular biology (Clifton, N.J.), 682, 91-101 (2010-11-09)
Extensive DNA fragmentation that generates a multitude of DNA double-strand breaks (DSBs) is a hallmark of apoptosis. A widely used approach to identify apoptotic cells relies on labeling DSBs in situ with fluorochromes. Flow or image cytometry is then used
Eisuke Gotoh
Chromosoma, 116(5), 453-462 (2007-05-16)
A basic question of cell biology is how DNA folds to chromosome. Numbers of examples have suggested the involvement of DNA replication in chromosome structure formation. To visualize and identify the dynamics of chromosome structure formation and to elucidate the

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