5-Ethynyl-20-deoxycytidine as a new agent for DNA labeling: Detection of proliferating cells

Analytical Biochemistry

Volumn 417, Issue 1, 2011, Pages 112-121

  Qu, Dezhong ^a,b   Wang, Guoxing ^a   Wang, Zhe ^a   Zhou, Li ^a,b   Chi, Weilin ^a   Cong, Shujie ^a,b   Ren, Xiaoshuai ^a,c   Liang, Peizhou ^a,c   Zhang, Biliang ^a,d  

^a GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^d GUANGZHOU MEDICAL UNIVERSITY   (China)

Author keywords

"Click" chemistry; 5 Ethynyl 20 deoxycytidine; Cell proliferation; DNA labeling; dTMP synthetase; EdU

Indexed keywords

CELL PROLIFERATION; CYTOLOGY; DNA; RADIOGRAPHY;

5-ETHYNYL-20-DEOXYCYTIDINE; CLICK CHEMISTRY; EXPERIMENTAL TECHNIQUES; IMMUNOHISTOCHEMISTRY; INHIBITION EFFECT; NOVEL TECHNIQUES; PROLIFERATING CELLS; SYNTHETASES;

CELLS;

5 ETHYNYLDEOXYCYTIDINE; THYMIDINE DERIVATIVE; UNCLASSIFIED DRUG; 5 ETHYNYLDEOXYURIDINE; 5-ETHYNYL-2'-DEOXYURIDINE; DEOXYURIDINE; DNA; DRUG DERIVATIVE; THYMIDINE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CELL GROWTH; CELL PROLIFERATION; COLON; CYTOTOXICITY; DNA DENATURATION; DNA SYNTHESIS; HUMAN; HUMAN CELL; ILEUM; IMMUNOHISTOCHEMISTRY; IN VITRO STUDY; IN VIVO STUDY; KIDNEY; LIVER; LUNG CANCER; MOUSE; NONHUMAN; NUCLEIC ACID ANALYSIS; PRIORITY JOURNAL; SPLEEN; ANIMAL; ANTIBODY SPECIFICITY; BIOSYNTHESIS; CELL DEATH; CHEMISTRY; DRUG EFFECT; FLOW CYTOMETRY; METABOLISM; METHODOLOGY; STAINING; TIME; TUMOR CELL LINE;

ANIMALS; CELL DEATH; CELL LINE, TUMOR; CELL PROLIFERATION; DEOXYURIDINE; DNA; FLOW CYTOMETRY; HUMANS; MICE; ORGAN SPECIFICITY; STAINING AND LABELING; THYMIDINE; TIME FACTORS;

EID: 80655145651     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2011.05.037     Document Type: Article

References (30)

1. J.H. Taylor, P.S. Woods, W.L. Hughes, The organization and duplication of chromosomes as revealed by autoradiographic studies using tritium-labeled thymidine, Proc. Natl. Acad. Sci. USA 43 (1957) 122-128.
2. H. Gratzner, Monoclonal antibody to 5-bromo- and 5-iododeoxyuridine: a new reagent for detection of DNA replication, Science 218 (1982) 474-475. (Pubitemid 12000901)
3. A. Salic, T. Mitchison, A chemical method for fast and sensitive detection of DNA synthesis in vivo, Proc. Natl. Acad. Sci. USA 105 (2008) 2415-2420. (Pubitemid 351520528)
4. S. Buck, J. Bradford, K. Gee, B. Agnew, S. Clarke, A. Salic, Detection of S-phase cell cycle progression using 5-ethynyl-20-deoxyuridine incorporation with click chemistry, an alternative to using 5-bromo-20-deoxyuridine antibodies, BioTechniques 44 (2008) 927-929. (Pubitemid 352007369)
5. C.W. Tornøe, C. Christensen, M. Meldal, Peptidotriazoles on solid phase: [1, 2, 3]-Triazoles by regiospecific copper(I)-catalyzed 1, 3-dipolar cycloadditions of terminal alkynes to azides, J. Org. Chem. 67 (2002) 3057- 3064. (Pubitemid 34457265)
6. V.V. Rostovtsev, L.G. Green, V.V. Fokin, K.B. Sharpless, A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes, Angew. Chem. Intl. Ed. Engl. 41 (2002) 2596-2599. (Pubitemid 34803480)
7. F. Himo, T. Lovell, R. Hilgraf, V.V. Rostovtsev, L. Noodleman, K.B. Sharpless, V.V. Fokin, Copper(I)-catalyzed synthesis of azoles: DFT study predicts unprecedented reactivity and intermediates, J. Am. Chem. Soc. 127 (2004) 210-216. (Pubitemid 40094384)
8. F. Chehrehasa, A.C.B. Meedeniya, P. Dwyer, G. Abrahamsen, A. Mackay-Sim, EdU, a new thymidine analogue for labelling proliferating cells in the nervous system, J. Neurosci. Meth. 177 (2009) 122-130.
9. C. Zeng, F. Pan, L.A. Jones, M.M. Lim, E.A. Griffin, Y.I. Sheline, M.A. Mintun, D.M. Holtzman, R.H. Mach, Evaluation of 5-ethynyl-20-deoxyuridine staining as a sensitive and reliable method for studying cell proliferation in the adult nervous system, Brain Res. 1319 (2010) 21-32.
10. M. Warren, K. Puskarczyk, S. Chapman, Chick embryo proliferation studies using EdU labeling, Dev. Dyn. 238 (2009) 944-949.
11. S. Diermeier-Daucher, S. Clarke, D. Hill, A. Vollmann-Zwerenz, J. Bradford, G. Brockhoff, Cell type specific applicability of 5-ethynyl-20- deoxyuridine (EdU) for dynamic proliferation assessment in flow cytometry, Cytometry A 75 (2009) 535-546.
12. D.J. Ferullo, D.L. Cooper, H.R. Moore, S.T. Lovett, Cell cycle synchronization of Escherichia coli using the stringent response, with fluorescence labeling assays for DNA content and replication, Methods 48 (2009) 8-13.
13. Y. Yu, A. Arora, W. Min, C.M. Roifman, E. Grunebaum, EdU incorporation is an alternative non-radioactive assay to thymidine uptake for in vitro measurement of mice T-cell proliferations, J. Immunol. Methods 350 (2009) 29-35.
14. H. Boije, P-H.D. Edqvist, F. Hallböök, Horizontal cell progenitors arrest in G2- phase and undergo terminal mitosis on the vitreal side of the chick retina, Dev. Biol. 330 (2009) 105-113.
15. C. Kaiser, A. Kamien, P. Shah, B. Chapman, D. Cotanche, 5-Ethynyl-20- deoxyuridine labeling detects proliferating cells in the regenerating avian cochlea, Laryngoscope 119 (2009) 1770-1775.
16. E. Kotogany, D. Dudits, G. Horvath, F. Ayaydin, A rapid and robust assay for detection of S-phase cell cycle progression in plant cells and tissues by using ethynyl deoxyuridine, Plant Methods 6 (2010) 5.
17. S. Limsirichaikul, A. Niimi, H. Fawcett, A. Lehmann, S. Yamashita, T. Ogi, A rapid non-radioactive technique for measurement of repair synthesis in primary human fibroblasts by incorporation of ethynyl deoxyuridine (EdU), Nucleic Acids Res. 37 (2009) e31.
18. Y. Nakazawa, S. Yamashita, A.R. Lehmann, T. Ogi, A semi-automated nonradioactive system for measuring recovery of RNA synthesis and unscheduled DNA synthesis using ethynyluracil derivatives, DNA Repair 9 (2010) 506-516.
19. G. Lin, G. Wang, L. Banie, H. Ning, A.W. Shindel, T.M. Fandel, T.F. Lue, C.-S. Lin, Treatment of stress urinary incontinence with adipose tissue-derived stem cells, Cytotherapy 12 (2010) 88-95.
20. S. Meneni, I. Ott, C.D. Sergeant, A. Sniady, R. Gust, R. Dembinski, 5-Alkynyl-20- deoxyuridines: chromatography-free synthesis and cytotoxicity evaluation against human breast cancer cells, Bioorg. Med. Chem. 15 (2007) 3082-3088. (Pubitemid 46400457)
21. M. Bobek, I. Kavai, R.A. Sharma, S. Grill, G. Dutschman, Y.C. Cheng, Acetylenic nucleosides: 4. 1-(b-D-Arabinofuranosyl)-5-ethynylcytosine: Improved synthesis and evaluation of biochemical and antiviral properties, J. Med. Chem. 30 (1987) 2154-2157. (Pubitemid 18046081)
22. K. Fujikawa-Yamamoto, S. Odashima, Synergistic effects of hydroxyurea and thymidine on the growth inhibition of V79 cells, Cell Struct. Funct. 14 (1989) 399-405. (Pubitemid 19245785)
23. E. De Clercq, J. Balzarini, J. Descamps, G.F. Huang, P.F. Torrence, D.E. Bergstrom, A.S. Jones, P. Serafinowski, G. Verhelst, R.T. Walker, Antiviral, antimetabolic, and cytotoxic activities of 5-substituted 20-deoxycytidines, Mol. Pharmacol. 21 (1982) 217-223. (Pubitemid 12148647)
24. A. Saran, Molecular orbital studies on nucleoside antibiotics: IX. Conformation of 5-ethynyl- and 5-vinyl-20-deoxycytidines, J. Mol. Struct. 179 (1988) 215- 223.
25. S. Hazra, S. Ort, M. Konrad, A. Lavie, Structural and kinetic characterization of human deoxycytidine kinase variants able to phosphorylate 5-substituted deoxycytidine and thymidine analogues, Biochemistry 49 (2010) 6784-6790.
26. P.J. Barr, P.A. Nolan, D.V. Santi, M.J. Robins, Inhibition of thymidylate synthetase by 5-alkynyl-20-deoxyuridylates, J. Med. Chem. 24 (1981) 1385-1388.
27. M. Meuth, H. Green, Induction of a deoxycytidineless state in cultured mammalian cells by bromodeoxyuridine, Cell 2 (1974) 109-112.
28. E. De Clercq, J. Balzarini, P.F. Torrence, M.P. Mertes, C.L. Schmidt, D. Shugar, P.J. Barr, A.S. Jones, G. Verhelst, R.T. Walker, Thymidylate synthetase as target enzyme for the inhibitory activity of 5-substituted 20-deoxyuridines on mouse leukemia L1210 cell growth, Mol. Pharmacol. 19 (1981) 321-330. (Pubitemid 11004238)
29. H.A. Rolton, H.M. Keir, Deoxycytidylate deaminase: properties of the enzyme from cultured kidney cells of baby hamster, Biochem. J. 141 (1974) 211-217.
30. A.R. Van Rompay, M. Johansson, A. Karlsson, Phosphorylation of nucleosides and nucleoside analogs by mammalian nucleoside monophosphate kinases, Pharmacol. Ther. 87 (2000) 189-198.