bromouracil
Sign in to saveAlso known as 1,2,3,4-tetrahydro-5-bromo-2,4-pyrimidinedione, 5-bromo-2,4(1H,3H)-pyrimidinedione
5-Bromouracil (5-BrU, 5BrUra, or br5Ura) is a brominated derivative of uracil that acts as an antimetabolite or base analog, substituting for thymine in DNA, and can induce DNA mutation in the same way as 2-aminopurine. It is used mainly as an experimental mutagen, but its deoxyriboside derivative (5-bromo-2-deoxy-uridine) is used to treat neoplasms.
Research
869 papers- Bromouracil mutagenesis: mispairing or misrepair?Mutation research · 1974
- The lesions produced by ultraviolet light in DNA containing 5-bromouracil.Quarterly reviews of biophysics · 1973
- Binding of 5-bromouracil-containing S/MAR DNA to the nuclear matrix.DNA research : an international journal for rapid publication of reports on genes and genomes · 2002
- Bromouracil mutagenesis and mismatch repair in mutator strains of Escherichia coli.Mutation research · 1978
- [Effects of 5-bromouracil and 5-bromodeoxyuridine in combination with 8-aza-adenine on the UV sensitivity of bacteria].Zeitschrift fur allgemeine Mikrobiologie · 1983
via PubMed
Wikidata facts
- Mass
- 189.938
Show 3 more facts
- chemical formula
- C₄H₃BrN₂O₂
- canonical SMILES
- C1=C(C(=O)NC(=O)N1)Br
- Commons category
- 5-Bromouracil
Sources (2)
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Article
2 sectionsContents
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- References
5-Bromouracil (5-BrU, 5BrUra, or br5Ura) is a brominated derivative of uracil that acts as an antimetabolite or base analog, substituting for thymine in DNA, and can induce DNA mutation in the same way as 2-aminopurine. It is used mainly as an experimental mutagen, but its deoxyriboside derivative (5-bromo-2-deoxy-uridine) is used to treat neoplasms.
5-BrU exists in three tautomeric forms that have different base pairing properties. The keto form (shown in the infobox) is complementary to adenine, so it can be incorporated into DNA by aligning opposite adenine residues during DNA replication (see below left). Alternatively, the enol (below right) and ion forms are complementary to guanine. This means that 5-BrU can be present in DNA either opposite adenine or guanine.