Luminescence studies of the intracellular distribution of a dinuclear gold(I) N-heterocyclic carbene complex

Angewandte Chemie - International Edition

Volumn 45, Issue 36, 2006, Pages 5966-5970

  Barnard, Peter J ^a   Wedlock, Louise E ^a   Baker, Murray V ^a   Berners Price, Susan J ^a   Joyce, David A ^b   Skelton, Brian W ^a   Steer, James H ^b  

^a UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

^b UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

Author keywords

Bioinorganic chemistry; Cellular distribution; Gold; Luminescent probes; N heterocyclic carbenes

Indexed keywords

BIOINORGANIC CHEMISTRY; CELLULAR DISTRIBUTION; LUMINESCENT PROBES; N-HETEROCYCLIC CARBENES;

CELLS; COMPLEXATION; LUMINESCENCE; MOLECULAR STRUCTURE; TUMORS;

GOLD;

CARBENE; DRUG DERIVATIVE; GOLD DERIVATIVE; HETEROCYCLIC COMPOUND; HYDROCARBON; METHANE;

ANIMAL; ARTICLE; CELL CULTURE; CHEMICAL MODEL; CHEMISTRY; CRYSTALLIZATION; LUMINESCENCE; METABOLISM; MOUSE; ULTRASTRUCTURE;

ANIMALS; CELLS, CULTURED; CRYSTALLIZATION; GOLD COMPOUNDS; HETEROCYCLIC COMPOUNDS; HYDROCARBONS; LUMINESCENCE; METHANE; MICE; MODELS, CHEMICAL;

EID: 33748767913     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601526     Document Type: Article

References (41)

1. a) W. F. Kean, L. Hart, W. W. Buchanan, Br. J. Rheumatol. 1997, 36, 560-572;
2. b) C. F. Shaw III, Chem. Rev. 1999, 99, 2589-2600;
3. c) E. R. T. Tiekink, Crit. Rev. Oncol. Hemat. 2002, 42, 225-248.
4. a) M. J. McKeage, S. J. Berners-Price, P. Galettis, R. J. Bowen, W. Brouwer, L. Ding, L. Zhuang, B. C. Baguley, Cancer Chemother. Pharmacol. 2000, 46, 343-350;
5. b) S. J. Berners-Price, R. J. Bowen, P. Galettis, P. C. Healy, M. J. McKeage, Coord. Chem. Rev. 1999, 185-186, 823-836.
6. P. J. Barnard, M. V. Baker, S. J. Berners-Price, D. A. Day, J. Inorg. Biochem. 2004, 98, 1642-1647.
7. P. J. Barnard, M. V. Baker, S. J. Berners-Price, B. W. Skelton, A. H. White, Dalton Trans. 2004, 1034-1047.
8. a) R. L. White-Morris, M. M. Olmstead, F. Jiang, D. S. Tinti, A. L. Balch, J. Am. Chem. Soc. 2002, 124, 2327-2336;
9. b) R. L. White-Morris, M. M. Olmstead, S. Attar, A. L. Balch, Inorg. Chem. 2005, 44, 5021-5029;
10. c) V. W.-W. Yam, C-L. Chan, C.-K. Li, K. M.-C. Wong, Coord. Chem. Rev. 2001, 216-217, 173-194;
11. d) S.-Y. Yu, Z.-X. Zhang, E. C.-C. Cheng, Y.-Z. Li, V. W.-W. Yam, H.-P. Huang, R. Zhang, J. Am. Chem. Soc. 2005, 127, 17994-17995;
12. e) V. J. Catalano, A. O. Etogo, J. Organomet. Chem. 2005, 690, 6041-6050;
13. f) V. J. Catalano, A. L. Moore, Inorg. Chem. 2005, 44, 6558-6566;
14. g) A. A. Mohamed, I. Kani, A. O. Ramirez, J. P. Fackler, Jr., Inorg. Chem. 2004, 43, 3833-3839.
15. a) H.-X. Zhang, C.-M. Che, Chem. Eur. J. 2001, 7, 4887-4893;
16. b) W-F. Fu, K.-C. Chan, V. M. Miskowski, C.-M. Che, Angew. Chem. 1999, 111, 2953-2955;
17. Angew. Chem. Int. Ed. 1999, 38, 2783-2785;
18. c) P. Pyykkö, Angew. Chem. 2004, 116, 4512-4557;
19. Angew. Chem. Int. Ed. 2004, 43, 4412-4456;
20. d) P. Pyykkö, Inorg. Chim. Acta 2005, 358, 4113-4130.
21. a) M. Bardaji, A. Laguna, Eur. J. Inorg. Chem. 2003, 3069-3079;
22. b) M. A. Mansour, W. B. Connick, R. J. Lachicotte, H. J. Gysling, R. Eisenberg, J. Am. Chem. Soc. 1998, 120, 1329-1330;
23. c) V. W.-W. Yam, C.-K. Li, C.-L. Chan, Angew. Chem. 1998, 110, 3041-3044;
24. Angew. Chem. Int. Ed. 1998, 37, 2857-2859;
25. d) V. W.-W. Yam, K.-L. Cheung, E. C.-C. Cheng, N. Zhu, K.-K. Cheung, Dalton Trans. 2003, 1830-1835.
26. a) G. A. Bowmaker in Gold: Progress in Chemistry Biochemistry and Technology (Ed.: H. Schmidbaur), Wiley, Chichester, 1999, pp. 841-881;
27. b) Z. Assefa, B. G. McBurnett, R. J. Staples, J. P. Fackler, Jr., Inorg. Chem. 1995, 34, 75-83;
28. c) W. E. van Zyl, J. M. Lopez-de-Luzuriaga, A. A. Mohamed, R. J. Staples, J. P. Fackler, Jr., Inorg. Chem. 2002, 41, 4579-4589;
29. d) N. L. Coker, J. A. Krause Bauer, R. C. Elder, J. Am. Chem. Soc. 2004, 126, 12-13.
30. Z. Assefa, B. G. McBurnett, R. J. Staples, J. P. Fackler, Jr., Inorg. Chem. 1995, 34, 4965-4972.
31. M. Luo, S. Guo, C. Zhou, R. Xie, Heterocycles 1995, 41, 1421-1424;
32. K. Sato, T. Onitake, S. Arai, T. Yamagishi, Heterocycles 2003, 60, 779-784.
33. -1; Ãca. 103 K. No hydrogens located in association with "O(1)"; Br(3) is modeled as disordered over a pair of well-separated, inversion related sites (3.291(2) Å). CCDC-295083 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
34. The color of 4 in solution is solvent dependent, with colorless solutions formed in organic solvents (methanol, ethanol, dimethyl sulfoxide (DMSO), and DMF) and pale green solutions formed in water. It is possible that the green color of solid samples of trans-4 results from the initially colorless crystals absorbing atmospheric water. The fascinating solvent dependence of the emissive behavior of 4 is currently under further investigation, and the results of these studies will be reported in due course.
35. P. Ralph, I. Nakoinz, J. Immunol. 1977, 119, 950-954.
36. J. Aaseth, M. Haugen, Ø. Førre, Analyst 1998, 123, 3-6.
37. A. R. Cowley, J. Davis, J. R. Dilworth, P. S. Donnelly, R. Dobson, A. Nightingale, J. M. Peach, B. Shore, D. Kerr, L. Seymour, Chem. Commun. 2005, 845-847.
38. a) B. A. Jansen, P. Wielaard, G. V. Kalayda, M. Ferrari, C. Molenaar, H. J. Tanke, J. Brouwer, H. J. Reedijk, J. Biol. Inorg. Chem. 2004, 9, 403-413;
39. b) G. V. Kalayda, B. A. Jansen, C. Molenaar, P. Wielaard, H. J. Tanke, H. J. Reedijk, J. Biol. Inorg. Chem. 2004, 9, 414-422.
40. a) R. Gallagher, S. Collins, J. Trujillo, K. Mcredie, M. Ahearn, S. Tsai, R. Metzgar, G. Aulakh, R. Ting, F. Ruscetti, R. Gallo, Blood 1979, 54, 713-733;
41. b) S. J. Collins, R. C. Gallo, R. E. Gallagher, Nature 1977, 270, 347-349.