B5002

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: 59-14-3
• Molecular Weight: 307.10
• Beilstein/REAXYS Number: 30395
• EC Number: 200-415-9
• MDL number: MFCD00006529
• UNSPSC Code: 41106305
• PubChem Substance ID: 24278270
• NACRES: NA.51

Properties

• biological source: synthetic (organic)
• 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

Description

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]

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.

Safety Information

• pictograms: GHS08
• signalword: Danger
• hcodes: H340,H361fd
• pcodes: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Muta. 1B - Repr. 2
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 2
• ppe: Eyeshields, Gloves, type N95 (US)