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Because BrdU can replace thymidine during DNA replication, it can cause [[mutation]]s, and its use is therefore potentially a health hazard.<ref name=pmid21785232/> However, because it is neither [[radioactive]] nor [[myelotoxic]] at labeling concentrations, it is widely preferred for ''in vitro'' studies of [[cancer]] cell proliferation<ref name="Fujimaki Cancer">{{cite journal|last=Fujimaki, MD|first=Takamitsu|coauthors=Masao Matsutani, MD, Osamu Nakamura, MD, Akio Asai, MD, Nobuaki Funada, MD, Morio Koike, MD, Hiromu Segawa, MD, Kouichi Aritake, MD, Takanori Fukushima, MD, Shuntaro Houjo, MD, Akira Tamura, MD, Keiji Sano, MD|title=Correlation Between Bromodeoxyuridine- Labeling Indices and Patient Prognosis in Cerebral Astrocytic Tumors of Adults|journal=Cancer|date=29 June 2006|year=2006|month=June|volume=67|issue=6|pages=1629-1634|accessdate=19 August 2012}}</ref><ref name="Cytometry Myelotoxic">{{cite journal|last=Hoshino|first=Takao|coauthors=Tadashi Nagashima, Judith Murovic, Ellen M. Levin, Victor A. Levin, and Stephen M. Rupp|title=Cell Kinetic Studies of In Situ Human Brain Tumors With Bromodeoxyuridine|journal=Cytometry|year=1985|volume=6|issue=6|pages=627-632|accessdate=19 August 2012}}</ref>. However, at [[radiosensitizing]] concentrations, BrdU becomes myelosuppressive thus limiting its use for radiosensitizing<ref name="Cancer Research" />.
Because BrdU can replace thymidine during DNA replication, it can cause [[mutation]]s, and its use is therefore potentially a health hazard.<ref name=pmid21785232/> However, because it is neither [[radioactive]] nor [[myelotoxic]] at labeling concentrations, it is widely preferred for ''in vitro'' studies of [[cancer]] cell proliferation<ref name="Fujimaki Cancer">{{cite journal|last=Fujimaki, MD|first=Takamitsu|coauthors=Masao Matsutani, MD, Osamu Nakamura, MD, Akio Asai, MD, Nobuaki Funada, MD, Morio Koike, MD, Hiromu Segawa, MD, Kouichi Aritake, MD, Takanori Fukushima, MD, Shuntaro Houjo, MD, Akira Tamura, MD, Keiji Sano, MD|title=Correlation Between Bromodeoxyuridine- Labeling Indices and Patient Prognosis in Cerebral Astrocytic Tumors of Adults|journal=Cancer|date=29 June 2006|year=2006|month=June|volume=67|issue=6|pages=1629-1634|accessdate=19 August 2012}}</ref><ref name="Cytometry Myelotoxic">{{cite journal|last=Hoshino|first=Takao|coauthors=Tadashi Nagashima, Judith Murovic, Ellen M. Levin, Victor A. Levin, and Stephen M. Rupp|title=Cell Kinetic Studies of In Situ Human Brain Tumors With Bromodeoxyuridine|journal=Cytometry|year=1985|volume=6|issue=6|pages=627-632|accessdate=19 August 2012}}</ref>. However, at [[radiosensitizing]] concentrations, BrdU becomes myelosuppressive thus limiting its use for radiosensitizing<ref name="Cancer Research" />.


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.<ref>{{cite journal |pages=24–34 |doi=10.1107/S0909049595013288 |title=MAD Phasing Strategies Explored with a Brominated Oligonucleotide Crystal at 1.65Å Resolution |year=1996 |last1=Peterson |first1=M. R. |last2=Harrop |first2=S. J. |last3=McSweeney |first3=S. M. |last4=Leonard |first4=G. A. |last5=Thompson |first5=A. W. |last6=Hunter |first6=W. N. |last7=Helliwell |first7=J. R. |journal=Journal of Synchrotron Radiation |volume=3 |pmid=16702655 |issue=Pt 1}}</ref><ref>{{cite journal |pages=374–80 |doi=10.1107/S0907444909051609 |pmc=2852301 |title=The magic triangle goes MAD: Experimental phasing with a bromine derivative |year=2010 |last1=Beck |first1=Tobias |last2=Gruene |first2=Tim |last3=Sheldrick |first3=George M. |journal=Acta Crystallographica Section D Biological Crystallography |volume=66 |issue=4 |pmid=20382990}}</ref>
BrdU differs from thymidine in that BrdU substitutes a Br group for thymidine's CH<sub>3</sub> group. The Br substitution can 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.<ref>{{cite journal |pages=24–34 |doi=10.1107/S0909049595013288 |title=MAD Phasing Strategies Explored with a Brominated Oligonucleotide Crystal at 1.65Å Resolution |year=1996 |last1=Peterson |first1=M. R. |last2=Harrop |first2=S. J. |last3=McSweeney |first3=S. M. |last4=Leonard |first4=G. A. |last5=Thompson |first5=A. W. |last6=Hunter |first6=W. N. |last7=Helliwell |first7=J. R. |journal=Journal of Synchrotron Radiation |volume=3 |pmid=16702655 |issue=Pt 1}}</ref><ref>{{cite journal |pages=374–80 |doi=10.1107/S0907444909051609 |pmc=2852301 |title=The magic triangle goes MAD: Experimental phasing with a bromine derivative |year=2010 |last1=Beck |first1=Tobias |last2=Gruene |first2=Tim |last3=Sheldrick |first3=George M. |journal=Acta Crystallographica Section D Biological Crystallography |volume=66 |issue=4 |pmid=20382990}}</ref>


==See also==
==See also==

Revision as of 04:15, 19 August 2012

Bromodeoxyuridine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.378 Edit this at Wikidata
MeSH Bromodeoxyuridine
UNII
  • 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 checkY
    Key: WOVKYSAHUYNSMH-VQVTYTSYSA-N checkY
  • 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
  • BrC=1C(=O)NC(=O)N(C=1)[C@H]2O[C@H]([C@H](O)C2)CO
Properties
C9H11BrN2O5
Molar mass 307.098
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Bromodeoxyuridine (5-bromo-2'-deoxyuridine, BrdU, BUdR, BrdUrd) is a synthetic nucleoside that is an analogue of thymidine. BrdU is commonly used in the detection of proliferating cells in living tissues.[1] 5-bromodeoxycytidine is deaminated to form BrdU in vitro[2].

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.[3]

BrdU can be passed to daughter cells upon replication[4]. BrdU has been demonstrated to be detectable over two years post-infusion[5] .

Because BrdU can replace thymidine during DNA replication, it can cause mutations, and its use is therefore potentially a health hazard.[3] However, because it is neither radioactive nor myelotoxic at labeling concentrations, it is widely preferred for in vitro studies of cancer cell proliferation[6][7]. However, at radiosensitizing concentrations, BrdU becomes myelosuppressive thus limiting its use for radiosensitizing[2].

BrdU differs from thymidine in that BrdU substitutes a Br group for thymidine's CH3 group. The Br substitution can 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.[8][9]

See also

References

  1. ^ Lehner, Bernadette; Sandner, Beatrice; Marschallinger, Julia; Lehner, Christine; Furtner, Tanja; Couillard-Despres, Sebastien; Rivera, Francisco J.; Brockhoff, Gero; Bauer, Hans-Christian (2011). "The dark side of BrdU in neural stem cell biology: Detrimental effects on cell cycle, differentiation and survival". Cell and Tissue Research. 345 (3): 313–28. doi:10.1007/s00441-011-1213-7. PMID 21837406.
  2. ^ a b Russo, Angelo (1984). "Pharmacological Evaluation of Intravenous Delivery of 5-Bromodeoxyuridine to Patients with Brain Tumors". Cancer Research. 44: 1702–1705. {{cite journal}}: |access-date= requires |url= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)
  3. ^ 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.
  4. ^ Kee, N (2002). "The utility of Ki-67 and BrdU as proliferative markers of adult neurogenesis". Journal of Neuroscience Methods. 115 (1): 97–105. {{cite journal}}: |access-date= requires |url= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)
  5. ^ Eriksson, Peter (1998). "Neurogenesis in the adult human hippocampus". Nature Medicine. 1313-1317. 4: 1313–1317. {{cite journal}}: |access-date= requires |url= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)
  6. ^ Fujimaki, MD, Takamitsu (29 June 2006). "Correlation Between Bromodeoxyuridine- Labeling Indices and Patient Prognosis in Cerebral Astrocytic Tumors of Adults". Cancer. 67 (6): 1629–1634. {{cite journal}}: |access-date= requires |url= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)CS1 maint: date and year (link)
  7. ^ Hoshino, Takao (1985). "Cell Kinetic Studies of In Situ Human Brain Tumors With Bromodeoxyuridine". Cytometry. 6 (6): 627–632. {{cite journal}}: |access-date= requires |url= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)
  8. ^ 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.
  9. ^ 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. PMID 20382990.


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