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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:
Molecular Weight:
547.04
MDL number:
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

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This Item
B7166D4001D9250
biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

assay

≥90%

assay

≥93%

assay

≥95%

assay

≥90% (HPLC)

form

powder

form

powder

form

powder

form

powder

solubility

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

solubility

-

solubility

-

solubility

water: 50 mg/mL, clear, colorless

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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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
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
Visualization of heavy ion tracks by labeling 3'-OH termini of induced DNA strand breaks
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