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B0631

Sigma-Aldrich

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

≥90%

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Synonym(s):
5-BrdUTP
Empirical Formula (Hill Notation):
C9H14BrN2O14P3
CAS Number:
102212-99-7
Molecular Weight:
547.04
MDL number:
MFCD00057405
PubChem Substance ID:
24891527
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

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 Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Avian models in teratology and developmental toxicology
Developmental Toxicology, 85-103 (2012)
The impact of bcl-2 expression and bax deficiency on prostate homeostasis in vivo
Bruckheimer EM, et al.
Oncogene, 19(20), 2404-2404 (2000)
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
A Wojcik et al.
Cytogenetic and genome research, 104(1-4), 304-309 (2004-05-27)
The DNA lesions responsible for the formation of sister chromatid exchanges (SCEs) have been the object of research for a long time. SCEs can be visualized by growing cells for either two rounds of replication in the presence of 5-bromo-2'-deoxyuridine
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
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