5-Bromouracil

5-Bromouracil

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ImageFile = 5-Bromouracil structure.png ImageSize = 150px
IUPACName = 5-Bromo-1H-pyrimidine-2,4-dione
OtherNames = 5-Bromo-2,4-dihydroxypyrimidine
Section1 = Chembox Identifiers
Abbreviations = 5-BrU
5-BU
CASNo = 51-20-7
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PubChem = 5802
SMILES = C1=C(C(=O)NC(=O)N1)Br
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Section2 = Chembox Properties
Formula = C4H3BrN2O2
MolarMass = 190.983 g/mol
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Section7 = Chembox Hazards
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5-Bromouracil (or 5-bromo-2,4(1H,3H)-pyrimidinedione or 5-BrU or 5-BU) 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. Its structure can also be found in 5-bromo-2-deoxy-uridine.

5-BrU exists in three tautomeric forms that have different base pairing properties. The keto form (pictured) is complementary to adenine so this can be incorporated into DNA by aligning opposite adenine residues during DNA replication. Alternatively, the enol and ion forms are complementary to guanine. This means that 5-BrU can be present in DNA either opposite adenine or guanine.

The three forms frequently interchange so base-pairing properties can become altered at any time. The result of this is that during a subsequent round of replication a different base is aligned opposite the 5-BrU residue. Further rounds of replication 'fix' the change by incorporating a normal nitrogen base into the complementary strand.

Thus 5-BrU induces a point mutation via base substitution. This base pair will change from an A-T to a G-C or from a G-C to an A-T after a number of replication cycles, depending on whether 5-BU is within the DNA molecule or is an incoming base when it is enolized or ionized.

References

* Griffiths, Anthony J. et al (2005). "Introduction to Genetic Analysis (8th Ed.)". W.H. Freeman. ISBN 0-7167-4939-4


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Look at other dictionaries:

  • bromouracil — noun Date: 1960 a mutagenic uracil derivative C4H3N2O2Br that is an analog of thymine and pairs readily with adenine and sometimes with guanine …   New Collegiate Dictionary

  • bromouracil — /broh moh yoor euh sil/, n. Biochem. a uracil derivative, C4H3N2O2Br, that pairs with adenine and sometimes with guanine during phage and bacterial DNA synthesis. [1955 60; BROMO + URACIL] * * * …   Universalium

  • bromouracil — bro·mo·ura·cil .brō mō yu̇r ə .sil, səl n a mutagenic uracil derivative C4H3N2O2Br that is an analog of thymine and pairs readily with adenine and sometimes with guanine during bacterial or bacteriophage DNA synthesis …   Medical dictionary

  • bromouracil — bro·mo·ura·cil …   English syllables

  • bromouracil — ˌbrōmōˈyu̇rəˌsil, məˈ , sə̇l noun Etymology: brom + uracil : a mutagenic uracil derivative C4H3N2O2Br that is an analogue of thymine and pairs readily with adenine and sometimes with guanine during bacterial or phage DNA synthesis * * * /broh moh …   Useful english dictionary

  • 5-bromouracil — 5 bromouracil. См. 5 бромурацил. (Источник: «Англо русский толковый словарь генетических терминов». Арефьев В.А., Лисовенко Л.А., Москва: Изд во ВНИРО, 1995 г.) …   Молекулярная биология и генетика. Толковый словарь.

  • 5-bromouracil — Synthetic analog (antimetabolite) of thymine, in which a bromine atom takes the place of the methyl group in thymine; a mutagen. * * * 5 bro·mo·ura·cil (bro″mo uґrə sil) a pyrimidine analogue with mutagenic properties …   Medical dictionary

  • BrU — bromouracil …   Medical dictionary

  • BrU — • bromouracil …   Dictionary of medical acronyms & abbreviations

  • 5-бромурацил — 5 bromouracil 5 бромурацил. Аналог тимина, обладающий мутагенной активностью; использование 5 Б. в качестве мутагена З.Литман и А.Парди в 1955 положило начало работам по молекулярной природе мутационного процесса. (Источник: «Англо русский… …   Молекулярная биология и генетика. Толковый словарь.

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