Bromodeoxyuridine
| Bromodeoxyuridine |
|
| Identifiers |
| CAS number |
59-14-3 Y |
| PubChem |
6918942 |
| ChemSpider |
5294121 Y |
| UNII |
G34N38R2N1 Y |
| MeSH |
Bromodeoxyuridine |
| ChEMBL |
CHEMBL222280 N |
| Jmol-3D images |
Image 1 |
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BrC=1C(=O)NC(=O)N(C=1)[C@H]2O[C@H]([C@H](O)C2)CO
|
-
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+/m1/s1 Y
Key: WOVKYSAHUYNSMH-VQVTYTSYSA-N Y
InChI=1/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+/m1/s1
Key: WOVKYSAHUYNSMH-VQVTYTSYBQ
|
| Properties |
| Molecular formula |
C9H11BrN2O5 |
| Molar mass |
307.098 |
N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
Bromodeoxyuridine (5-bromo-2'-deoxyuridine, BrdU) is a synthetic nucleoside that is an analogue of thymidine. BrdU is commonly used in the detection of proliferating cells in living tissues.[1]
BrdU can be incorporated into the newly synthesized DNA of replicating cells (during the S phase of the cell cycle), substituting for thymidine during DNA replication. Antibodies specific for BrdU can then be used to detect the incorporated chemical (see immunohistochemistry), thus indicating cells that were actively replicating their DNA. Binding of the antibody requires denaturation of the DNA, usually by exposing the cells to acid or heat.[2]
Because BrdU can replace thymidine during DNA replication, it can cause mutations, and its use is therefore potentially a health hazard.[2]
The Br substitution can also be used in X-Ray diffraction experiments in crystals containing either DNA or RNA. The Br atom acts as an anomalous scatterer and its larger size will affect the crystal's x-ray diffraction enough to detect isomorphous differences as well.[3][4]
See also
External links
References
- ^ Lehner, Bernadette; Sandner, Beatrice; Marschallinger, Julia; Lehner, Christine; Furtner, Tanja; Couillard-Despres, Sebastien; Rivera, Francisco J.; Brockhoff, Gero et al. (2011). "The dark side of BrdU in neural stem cell biology: Detrimental effects on cell cycle, differentiation and survival". Cell and Tissue Research. doi:10.1007/s00441-011-1213-7. PMID 21837406.
- ^ a b Konishi, Teruaki; Takeyasu, Akihiro; Natsume, Toshiyuki; Furusawa, Yoshiya; Hieda, Kotaro (2011). "Visualization of Heavy Ion Tracks by Labeling 3'-OH Termini of Induced DNA Strand Breaks". Journal of Radiation Research 52 (4): 433–40. doi:10.1269/jrr.10097. PMID 21785232.
- ^ Peterson, M. R.; Harrop, S. J.; McSweeney, S. M.; Leonard, G. A.; Thompson, A. W.; Hunter, W. N.; Helliwell, J. R. (1996). "MAD Phasing Strategies Explored with a Brominated Oligonucleotide Crystal at 1.65Å Resolution". Journal of Synchrotron Radiation 3 (Pt 1): 24–34. doi:10.1107/S0909049595013288. PMID 16702655.
- ^ Beck, Tobias; Gruene, Tim; Sheldrick, George M. (2010). "The magic triangle goes MAD: Experimental phasing with a bromine derivative". Acta Crystallographica Section D Biological Crystallography 66 (4): 374–80. doi:10.1107/S0907444909051609. PMC 2852301. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2852301.