Cellular Localisation of Antitumoral 6-Alkyl Thymoquinones Revealed by an Alkyne-Azide Click Reaction and the Streptavidin-Biotin System

ChemBioChem

Volumn 12, Issue 8, 2011, Pages 1237-1241

  Effenberger Neidnicht, Katharina ^a   Breyer, Sandra ^a   Mahal, Katharina ^a   Diestel, Randi ^b   Sasse, Florenz ^b   Schobert, Rainer ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

^b HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

Author keywords

Alkynes; Biotin; Click chemistry; Fluorescent probes; Thymoquinone

Indexed keywords

3 AZIDO 7 HYDROXYCOUMARIN; 6 (DEC 9 YNYL)THYMOQUINONE; ALKYNE; ANTINEOPLASTIC AGENT; BIOTIN; COUMARIN; STREPTAVIDIN; UNCLASSIFIED DRUG;

ANTIBODY SPECIFICITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL NUCLEUS; CELL STRUCTURE; CELLULAR DISTRIBUTION; CHEMICAL REACTION; CONTROLLED STUDY; CYCLOADDITION; GOLGI COMPLEX; HUMAN; HUMAN CELL; HUMAN TISSUE; KIDNEY CELL; MITOCHONDRION; PRIORITY JOURNAL;

ALKYNES; ANTINEOPLASTIC AGENTS; AZIDES; BENZOQUINONES; BIOTIN; CELL COMPARTMENTATION; CELL LINE, TUMOR; CLICK CHEMISTRY; FEMALE; FLUORESCENCE; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NEOPLASMS; STAINING AND LABELING; STREPTAVIDIN;

POTOROUS;

EID: 79955966975     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201000762     Document Type: Article

References (26)

1. Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless, M. G. Finn, J. Am. Chem. Soc. 2003, 125, 3192-3193.
2. W. G. Lewis, L. G. Green, F. Grynszpan, Z. Radić, P. R. Carlier, P. Taylor, M. G. Finn, K. B. Sharpless, Angew. Chem. 2002, 114, 1095-1099; Angew. Chem. Int. Ed. 2002, 41, 1053-1057.
3. K. E. Beatty, J. C. Liu, F. Xie, D. C. Dieterich, E. M. Schuman, Q. Wang, D. A. Tirrell, Angew. Chem. 2006, 118, 7524-7527; Angew. Chem. Int. Ed. 2006, 45, 7364-7367.
4. S. Maschauer, J. Einsiedel, R. Haubner, C. Hocke, M. Ocker, H. Hübner, T. Kuwert, P. Gmeiner, O. Prante, Angew. Chem. 2010, 122, 988-992; Angew. Chem. Int. Ed. 2010, 49, 976-979.
5. A. S. Raghavan, H. C. Hang, Drug Discovery Today 2009, 14, 178-184.
6. R. El Mezayen, M. El Gazzar, M. R. Nicolls, J. C. Marecki, S. C. Dreskin, H. Nomiyama, Immunol. Lett. 2006, 106, 72-81.
7. D. R. Worthen, O. A. Ghosheh, P. A. Crooks, Anticancer Res. 1998, 18, 1527-1532.
8. O. A. Badary, A. M. Gamal El-Din, Cancer Detect. Prev. 2001, 25, 362-368.
9. H. Gali-Muhtasib, A. Roessner, R. Schneider-Stock, Int. J. Biochem. Cell Biol. 2006, 38, 1249-1253.
10. H. Gali-Muhtasib, M. Ocker, D. Kuester, S. Krueger, Z. El-Hajj, A. Diestel, M. Evert, N. El-Najjar, B. Peters, A. Jurjus, A. Roessner, R. Schneider-Stock, J. Cell. Mol. Med. 2008, 12, 330-342.
11. H. Gali-Muhtasib, M. Diab-Assaf, C. Boltze, J. Al-Hmaira, R. Hartig, A. Roessner, R. Schneider-Stock, Int. J. Oncol. 2004, 25, 857-866.
12. M. A. El-Mahdy, Q. Zhu, Q. E. Wang, G. Wani, A. A. Wani, Int. J. Cancer 2005, 117, 409-417.
13. S. Breyer, K. Effenberger, R. Schobert, ChemMedChem 2009, 4, 761-768.
14. K. Effenberger, S. Breyer, R. Schobert, Chem. Biodiversity 2010, 7, 129-139.
15. G. Gitlin, E. A. Bayer, M. Wilchek, Biochem. J. 1990, 269, 527-530.
16. N. Jacobsen, K. Torssell, Justus Liebigs Ann. Chem. 1972, 763, 135-147.
17. R. Jockers, R. D. Schmid, H. Rieger, K. Krohn, Liebigs Ann. Chem. 1991, 315-321.
18. M. Delépine, Bull. Soc. Chim. Fr. 1895, 13, 352-361.
19. N. Blažzević, D. Kolbah, B. Belin, V. Šunjić, F. Kafjež, Synthesis 1979, 161-176.
20. W. König, R. Geiger, Chem. Ber. 1970, 103, 788-798.
21. T. Mosmann, J. Immunol. Methods 1983, 65, 55-63.
22. K. Effenberger-Neidnicht, R. Schobert, Cancer Chemother. Pharmacol. 2010, 67, 867-874.
23. R. Huisgen, Angew. Chem. 1963, 75, 742-754; Angew. Chem. Int. Ed. Engl. 1963, 2, 633-645.
24. R. Huisgen, Angew. Chem. 1963, 75, 604-637; Angew. Chem. Int. Ed. Engl. 1963, 2, 565-598.
25. K. Sivakumar, F. Xie, B. M. Cash, S. Long, H. N. Barnhill, Q. Wang, Org. Lett. 2004, 6, 4603-4606.
26. Y. I. Hassan, J. Zempleni, J. Nutr. 2006, 136, 1763-1765.