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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/02/07 11:39:12」(JST)

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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.

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.

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-BrU 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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English Journal

Effect of substituents on the preferred modes of one-electron reductive cleavage of N-cl and N-br bonds.

O'Reilly RJ, Karton A, Radom L.SourceSchool of Chemistry and ARC Centre of Excellence for Free Radical Chemistry and Biotechnology, University of Sydney , Sydney, NSW 2006, Australia.
The journal of physical chemistry. A.J Phys Chem A.2013 Jan 17;117(2):460-72. doi: 10.1021/jp310048f. Epub 2013 Jan 3.
In this study, we investigate the effect of substituents in determining the modes of one-electron reductive cleavage of X-NRR' (X = Cl and Br) molecules. We achieve this through comparison of the calculated gas-phase electron affinities (EAs) and aqueous-phase one-electron reduction potentials (E°'
PMID 23282473

Photoreactivities of 5-bromouracil-containing RNAs.

Morinaga H, Kizaki S, Takenaka T, Kanesato S, Sannohe Y, Tashiro R, Sugiyama H.SourceDepartment of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8501, Japan.
Bioorganic & medicinal chemistry.Bioorg Med Chem.2013 Jan 15;21(2):466-9. doi: 10.1016/j.bmc.2012.11.010. Epub 2012 Nov 24.
5-Bromouracil ((Br)U) was incorporated into three types of synthetic RNA and the products of the photoirradiated (Br)U-containing RNAs were investigated using HPLC and MS analysis. The photoirradiation of r(GCA(Br)UGC)(2) and r(CGAA(Br)UUGC)/r(GCAAUUCG) in A-form RNA produced the corresponding 2'-ke
PMID 23266180

Determination of gemcitabine and its metabolite in extracellular fluid of rat brain tumor by ultra performance liquid chromatography-tandem mass spectrometry using microdialysis sampling after intralesional chemotherapy.

Sun Y, Tang D, Chen H, Zhang F, Fan B, Zhang B, Fang S, Lu Q, Wei Y, Yin J, Yin X.SourceKey Laboratory of New Drug and Clinical Application, Xuzhou Medical College, No. 209 Tongshan Road, Xuzhou 221004, Jiangsu, China; Department of Clinical Pharmacology, School of Pharmacy, Xuzhou Medical College, No. 209 Tongshan Road, Xuzhou 221004, Jiangsu, China.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.J Chromatogr B Analyt Technol Biomed Life Sci.2013 Jan 9;919-920C:10-19. doi: 10.1016/j.jchromb.2012.12.027. [Epub ahead of print]
The cytotoxic agent Gemcitabine (2',2'-difluoro-2'-deoxycytidine) has been proved to be effective in the treatment of malignant gliomas. A rapid, sensitive and specific ultra performance liquid chromatography with tandem mass spectrometry (UPLC-MS/MS) assay using microdialysis sampling was developed
PMID 23396113

Japanese Journal

<i>In vitro</i> comet assay in cultured human corneal epithelial cells

Fundamental Toxicological Sciences 2(4), 147-153, 2015
NAID 130005097696

Locating the uracil-5-yl radical formed upon photoirradiation of 5-bromouracil-substituted DNA.

Nucleic acids research 42(22), 13469-13473, 2014-12-16
NAID 120005666202

Sequence-specific electron injection into DNA from an intermolecular electron donor.

Nucleic acids research 41(8), 4724-4728, 2013-04-01
NAID 120005245128

Related Pictures

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★リンクテーブル★

リンク元	「5-ブロモウラシル」

「5-ブロモウラシル」

5-Bromouracil
	IUPAC name 5-Bromo-1H-pyrimidine-2,4-dione
	Other names 5-Bromo-2,4-dihydroxypyrimidine
Identifiers
Abbreviations	5-BrU; 5-BU
CAS number	51-20-7
PubChem	5802
ChemSpider	5597
ChEBI	CHEBI:20552
ChEMBL	CHEMBL144730
Jmol-3D images	Image 1
	SMILES Br/C1=C/NC(=O)NC1=O ;
	InChI InChI=1S/C4H3BrN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9) ; Key: LQLQRFGHAALLLE-UHFFFAOYSA-N InChI=1/C4H3BrN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9); Key: LQLQRFGHAALLLE-UHFFFAOYAN ;
Properties
Molecular formula	C4H3BrN2O2
Molar mass	190.983 g/mol
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

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英: 5-bromouracil, 5BU, 5-BU
関: ウラシル

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5-bromouracil