fbpx
Wikipedia

Bromodeoxyuridine

April 12, 2024

Bromodeoxyuridine (5-bromo-2'-deoxyuridine, BrdU, BUdR, BrdUrd, broxuridine) is a synthetic nucleoside analogue with a chemical structure similar to thymidine. BrdU is commonly used to study cell proliferation in living tissues[1] and has been studied as a radiosensitizer[2] and diagnostic tool in people with cancer.[3]

Bromodeoxyuridine
Names
IUPAC name
5-Bromo-2′-deoxyuridine
Systematic IUPAC name
5-Bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4(1H,3H)-dione
Identifiers
  • 59-14-3 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL222280 N
ChemSpider
  • 5294121 Y
  • 5813 N
ECHA InfoCard 100.000.378
MeSH Bromodeoxyuridine
  • 6035
UNII
  • G34N38R2N1 Y
  • DTXSID7033105
  • 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+/m0/s1 N
    Key: WOVKYSAHUYNSMH-RRKCRQDMSA-N N
  • 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+/m0/s1
    Key: WOVKYSAHUYNSMH-RRKCRQDMBM
  • c1c(c(=O)[nH]c(=O)n1[C@H]2C[C@@H]([C@H](O2)CO)O)Br
Properties
C9H11BrN2O5
Molar mass 307.100 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

During the S phase of the cell cycle (when DNA replication occurs), BrdU can be incorporated in place of thymidine in newly synthesized DNA molecules of dividing cells.[4] Cells that have recently performed DNA replication or DNA repair can be detected with antibodies specific for BrdU using techniques such as immunohistochemistry or immunofluorescence.[5] BrdU-labelled cells in humans can be detected up to two years after BrdU infusion.[6]

Because BrdU can replace thymidine during DNA replication, it can cause mutations, and its use is therefore potentially a health hazard.[citation needed] However, because it is neither radioactive nor myelotoxic at labeling concentrations, it is widely preferred for in vivo studies of cancer cell proliferation.[7][8] However, at radiosensitizing concentrations, BrdU becomes myelosuppressive, thus limiting its use for radiosensitizing.[2]

BrdU differs from thymidine in that BrdU substitutes a bromine atom 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.[9][10]

Bromodeoxyuridine releases gene silencing caused by DNA methylation.[11]

BrdU can also be used to identify microorganisms that respond to specific carbon substrates in aquatic[12] and soil[13] environments. A carbon substrate added to the incubations of environmental samples will cause the growth of microorganisms that can utilize that substrate. These microorganisms will then incorporate BrdU into their DNA as they grow. Community DNA can then be isolated and BrdU-labeled DNA purified using an immunocapture technique.[14] Subsequent sequencing of the labeled DNA can then be used to identify the microbial taxa that participated in the degradation of the added carbon source.

However, it is not certain whether all microbes present in an environmental sample can incorporate BrdU into their biomass during de novo DNA synthesis. Therefore, a group of microorganisms may respond to a carbon source but go undetected using this technique. Additionally, this technique is biased towards identifying microorganisms with A- and T-rich genomes.

DNA with BrdU transcribes as usual DNA, with guanine included in RNA as a complement to BrdU.[15]

See also edit

References edit

  1. ^ Lehner, Bernadette; Sandner, Beatrice; Marschallinger, Julia; Lehner, Christine; Furtner, Tanja; Couillard-Despres, Sebastien; Rivera, Francisco J.; Brockhoff, Gero; Bauer, Hans-Christian; Weidner, Norbert; Aigner, Ludwig (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. S2CID 756261.
  2. ^ a b Russo A, Gianni L, Kinsella TJ, Klecker RW, Jenkins J, Rowland J, Glatstein E, Mitchell JB, Collins J, Myers C (1984). "Pharmacological evaluation of intravenous delivery of 5-bromodeoxyuridine to patients with brain tumors". Cancer Res. 44 (4): 1702–5. PMID 6704976.
  3. ^ Dolbeare, F (May 1995). "Bromodeoxyuridine: a diagnostic tool in biology and medicine, Part I: Historical perspectives, histochemical methods and cell kinetics". The Histochemical Journal. 27 (5): 339–69. doi:10.1007/BF02389022. PMID 7657555. S2CID 21785471.
  4. ^ Kee, N; S Sivalingam; R Boonstra; J.M Wojtowicz (March 2002). "The utility of Ki-67 and BrdU as proliferative markers of adult neurogenesis". Journal of Neuroscience Methods. 115 (1): 97–105. doi:10.1016/S0165-0270(02)00007-9. hdl:1807/357. PMID 11897369. S2CID 17572667.
  5. ^ 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. Bibcode:2011JRadR..52..433K. doi:10.1269/jrr.10097. PMID 21785232.
  6. ^ Eriksson, Peter; Ekaterina Perfilieva; Thomas Björk-Eriksson; Ann-Marie Alborn; Claes Nordborg; Daniel A. Peterson; Fred H. Gage (1998). "Neurogenesis in the adult human hippocampus". Nature Medicine. 1313-1317. 4 (11): 1313–1317. doi:10.1038/3305. PMID 9809557.
  7. ^ Fujimaki, Takamitsu; Masao Matsutani; Osamu Nakamura; Akio Asai; Nobuaki Funada; Morio Koike; Hiromu Segawa; Kouichi Aritake; Takanori Fukushima; Shuntaro Houjo; Akira Tamura; Keiji Sano (29 June 2006). "Correlation Between Bromodeoxyuridine- Labeling Indices and Patient Prognosis in Cerebral Astrocytic Tumors of Adults". Cancer. 67 (6): 1629–1634. doi:10.1002/1097-0142(19910315)67:6<1629::AID-CNCR2820670626>3.0.CO;2-E. PMID 2001552.
  8. ^ Hoshino, Takao; Tadashi Nagashima; Judith Murovic; Ellen M. Levin; Victor A. Levin; Stephen M. Rupp (1985). "Cell Kinetic Studies of In Situ Human Brain Tumors With Bromodeoxyuridine". Cytometry. 6 (6): 627–632. doi:10.1002/cyto.990060619. PMID 2998714.
  9. ^ 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.
  10. ^ Beck, Tobias; Gruene, Tim; Sheldrick, George M. (2010). "The magic triangle goes MAD: Experimental phasing with a bromine derivative". Acta Crystallographica Section D. 66 (4): 374–80. doi:10.1107/S0907444909051609. PMC 2852301. PMID 20382990.
  11. ^ Weiss RA (2013). "On the concept and elucidation of endogenous retroviruses". Philos. Trans. R. Soc. Lond. B Biol. Sci. 368 (1626): 20120494. doi:10.1098/rstb.2012.0494. PMC 3758183. PMID 23938748.
  12. ^ Tada, Yuya; Grossart, Hans-Peter (2013). "Community shifts of actively growing lake bacteria after N-acetyl-glucosamine addition: improving the BrdU-FACS method". The ISME Journal. 8 (2): 441–454. doi:10.1038/ismej.2013.148. ISSN 1751-7362. PMC 3906810. PMID 23985742.
  13. ^ Borneman J (1999). "Culture-independent identification of microorganisms that respond to specified stimuli". Appl. Environ. Microbiol. 65 (8): 3398–400. Bibcode:1999ApEnM..65.3398B. doi:10.1128/AEM.65.8.3398-3400.1999. PMC 91510. PMID 10427025.
  14. ^ Urbach, Ena; Kevin L. Vergin; Stephen J. Giovannoni (March 1999). "Immunochemical Detection and Isolation of DNA from Metabolically Active Bacteria". Applied and Environmental Microbiology. 65 (3): 1207–1213. Bibcode:1999ApEnM..65.1207U. doi:10.1128/AEM.65.3.1207-1213.1999. PMC 91166. PMID 10049885.
  15. ^ Hill BT, Baserga R (1975). "Effect of 5-bromodeoxyuridine on the transcriptional properties of the genome in WI-38 human diploid fibroblasts". Chem. Biol. Interact. 10 (5): 363–375. doi:10.1016/0009-2797(75)90058-7. PMID 1095238.

External links edit

  • BrdU at OpenWetWare
  • BrdU Modifications at IDT DNA

April 12, 2024
bromodeoxyuridine, this, article, technical, most, readers, understand, please, help, improve, make, understandable, experts, without, removing, technical, details, february, 2021, learn, when, remove, this, template, message, bromo, deoxyuridine, brdu, budr, . This article may be too technical for most readers to understand Please help improve it to make it understandable to non experts without removing the technical details February 2021 Learn how and when to remove this template message Bromodeoxyuridine 5 bromo 2 deoxyuridine BrdU BUdR BrdUrd broxuridine is a synthetic nucleoside analogue with a chemical structure similar to thymidine BrdU is commonly used to study cell proliferation in living tissues 1 and has been studied as a radiosensitizer 2 and diagnostic tool in people with cancer 3 Bromodeoxyuridine NamesIUPAC name 5 Bromo 2 deoxyuridineSystematic IUPAC name 5 Bromo 1 2R 4S 5R 4 hydroxy 5 hydroxymethyl oxolan 2 yl pyrimidine 2 4 1H 3H dioneIdentifiersCAS Number 59 14 3 Y3D model JSmol Interactive imageChEMBL ChEMBL222280 NChemSpider 5294121 Y5813 NECHA InfoCard 100 000 378MeSH BromodeoxyuridinePubChem CID 6035UNII G34N38R2N1 YCompTox Dashboard EPA DTXSID7033105InChI 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 m0 s1 NKey WOVKYSAHUYNSMH RRKCRQDMSA N NInChI 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 m0 s1Key WOVKYSAHUYNSMH RRKCRQDMBMSMILES c1c c O nH c O n1 C H 2C C H C H O2 CO O BrPropertiesChemical formula C 9H 11Br N 2O 5Molar mass 307 100 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references During the S phase of the cell cycle when DNA replication occurs BrdU can be incorporated in place of thymidine in newly synthesized DNA molecules of dividing cells 4 Cells that have recently performed DNA replication or DNA repair can be detected with antibodies specific for BrdU using techniques such as immunohistochemistry or immunofluorescence 5 BrdU labelled cells in humans can be detected up to two years after BrdU infusion 6 Because BrdU can replace thymidine during DNA replication it can cause mutations and its use is therefore potentially a health hazard citation needed However because it is neither radioactive nor myelotoxic at labeling concentrations it is widely preferred for in vivo studies of cancer cell proliferation 7 8 However at radiosensitizing concentrations BrdU becomes myelosuppressive thus limiting its use for radiosensitizing 2 BrdU differs from thymidine in that BrdU substitutes a bromine atom 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 9 10 Bromodeoxyuridine releases gene silencing caused by DNA methylation 11 BrdU can also be used to identify microorganisms that respond to specific carbon substrates in aquatic 12 and soil 13 environments A carbon substrate added to the incubations of environmental samples will cause the growth of microorganisms that can utilize that substrate These microorganisms will then incorporate BrdU into their DNA as they grow Community DNA can then be isolated and BrdU labeled DNA purified using an immunocapture technique 14 Subsequent sequencing of the labeled DNA can then be used to identify the microbial taxa that participated in the degradation of the added carbon source However it is not certain whether all microbes present in an environmental sample can incorporate BrdU into their biomass during de novo DNA synthesis Therefore a group of microorganisms may respond to a carbon source but go undetected using this technique Additionally this technique is biased towards identifying microorganisms with A and T rich genomes DNA with BrdU transcribes as usual DNA with guanine included in RNA as a complement to BrdU 15 See also edit5 Bromouracil 5 Bromouridine 5 Ethynyl 2 deoxyuridine Trypan blueReferences edit Lehner Bernadette Sandner Beatrice Marschallinger Julia Lehner Christine Furtner Tanja Couillard Despres Sebastien Rivera Francisco J Brockhoff Gero Bauer Hans Christian Weidner Norbert Aigner Ludwig 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 S2CID 756261 a b Russo A Gianni L Kinsella TJ Klecker RW Jenkins J Rowland J Glatstein E Mitchell JB Collins J Myers C 1984 Pharmacological evaluation of intravenous delivery of 5 bromodeoxyuridine to patients with brain tumors Cancer Res 44 4 1702 5 PMID 6704976 Dolbeare F May 1995 Bromodeoxyuridine a diagnostic tool in biology and medicine Part I Historical perspectives histochemical methods and cell kinetics The Histochemical Journal 27 5 339 69 doi 10 1007 BF02389022 PMID 7657555 S2CID 21785471 Kee N S Sivalingam R Boonstra J M Wojtowicz March 2002 The utility of Ki 67 and BrdU as proliferative markers of adult neurogenesis Journal of Neuroscience Methods 115 1 97 105 doi 10 1016 S0165 0270 02 00007 9 hdl 1807 357 PMID 11897369 S2CID 17572667 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 Bibcode 2011JRadR 52 433K doi 10 1269 jrr 10097 PMID 21785232 Eriksson Peter Ekaterina Perfilieva Thomas Bjork Eriksson Ann Marie Alborn Claes Nordborg Daniel A Peterson Fred H Gage 1998 Neurogenesis in the adult human hippocampus Nature Medicine 1313 1317 4 11 1313 1317 doi 10 1038 3305 PMID 9809557 Fujimaki Takamitsu Masao Matsutani Osamu Nakamura Akio Asai Nobuaki Funada Morio Koike Hiromu Segawa Kouichi Aritake Takanori Fukushima Shuntaro Houjo Akira Tamura Keiji Sano 29 June 2006 Correlation Between Bromodeoxyuridine Labeling Indices and Patient Prognosis in Cerebral Astrocytic Tumors of Adults Cancer 67 6 1629 1634 doi 10 1002 1097 0142 19910315 67 6 lt 1629 AID CNCR2820670626 gt 3 0 CO 2 E PMID 2001552 Hoshino Takao Tadashi Nagashima Judith Murovic Ellen M Levin Victor A Levin Stephen M Rupp 1985 Cell Kinetic Studies of In Situ Human Brain Tumors With Bromodeoxyuridine Cytometry 6 6 627 632 doi 10 1002 cyto 990060619 PMID 2998714 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 65A 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 66 4 374 80 doi 10 1107 S0907444909051609 PMC 2852301 PMID 20382990 Weiss RA 2013 On the concept and elucidation of endogenous retroviruses Philos Trans R Soc Lond B Biol Sci 368 1626 20120494 doi 10 1098 rstb 2012 0494 PMC 3758183 PMID 23938748 Tada Yuya Grossart Hans Peter 2013 Community shifts of actively growing lake bacteria after N acetyl glucosamine addition improving the BrdU FACS method The ISME Journal 8 2 441 454 doi 10 1038 ismej 2013 148 ISSN 1751 7362 PMC 3906810 PMID 23985742 Borneman J 1999 Culture independent identification of microorganisms that respond to specified stimuli Appl Environ Microbiol 65 8 3398 400 Bibcode 1999ApEnM 65 3398B doi 10 1128 AEM 65 8 3398 3400 1999 PMC 91510 PMID 10427025 Urbach Ena Kevin L Vergin Stephen J Giovannoni March 1999 Immunochemical Detection and Isolation of DNA from Metabolically Active Bacteria Applied and Environmental Microbiology 65 3 1207 1213 Bibcode 1999ApEnM 65 1207U doi 10 1128 AEM 65 3 1207 1213 1999 PMC 91166 PMID 10049885 Hill BT Baserga R 1975 Effect of 5 bromodeoxyuridine on the transcriptional properties of the genome in WI 38 human diploid fibroblasts Chem Biol Interact 10 5 363 375 doi 10 1016 0009 2797 75 90058 7 PMID 1095238 External links editBrdU at OpenWetWare BrdU Modifications at IDT DNA Retrieved from https en wikipedia org w index php title Bromodeoxyuridine amp oldid 1171070505, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.