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B5002

Sigma-Aldrich

5-Bromo-2′-deoxyuridine

≥99% (HPLC)

Synonym(s):
5-BrdU, 5-Bromo-1-(2-deoxy-β-D-ribofuranosyl)uracil, 5-Bromouracil deoxyriboside, BUdR
Empirical Formula (Hill Notation):
C9H11BrN2O5
CAS Number:
Molecular Weight:
307.10
Beilstein:
30395
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.51

Quality Level

assay

≥99% (HPLC)

form

powder

mp

191-194 °C (dec.) (lit.)

solubility

DMSO: 50 mg/mL, clear, colorless to very faintly yellow

storage temp.

−20°C

SMILES string

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

InChI

1S/C9H11BrN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1

InChI key

WOVKYSAHUYNSMH-RRKCRQDMSA-N

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Application

5-Bromo-2′-deoxyuridine (5-BrdU) is a thymidine analogue which is incorporated into DNA. 5-BrdU is routinely and extensively used to measure DNA synthesis and to label dividing cells. Consequently 5-BrdU is used to study cell signaling and other processes that induce cell proliferation.
5-Bromo-2′-deoxyuridine has been used:
  • as a supplement to study the effect of electroconvulsive seizures on hippocampal neurogenesis
  • as a supplement to study the loss-of-gene function in adult zebrafish heart
  • in T lymphocyte proliferation assay{133]

Packaging

100, 250, 500 mg in glass bottle
1, 5, 100 g in glass bottle

Biochem/physiol Actions

5-Bromo-2′-deoxyuridine (BrdU) is used to analyze cell proliferation, because of its facile incorporation into DNA during the S phase of the cell cycle. BrdU stimulates cellular differentiation and maturation in leukemia cell lines, while it inhibits differentiation of friend erythroleukemia cells. Studies of BrdU incorporation often subsequently use BrdU-specific antibodies with fluorescent tags, for detection of the incorporated BrdU, via such methods as flow cytometry or fluorescence microscopy.
Thymidine analog used as a mutagen in genetic research. Selectively incorporated into cellular DNA during S-phase.

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Muta. 1B - Repr. 2

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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