Identification of the structural determinants for anticancer activity of a ruthenium arene peptide conjugate

Chemistry - A European Journal

Volumn 19, Issue 28, 2013, Pages 9297-9307

  Meier, Samuel M ^a   Novak, Maria ^a   Kandioller, Wolfgang ^a   Jakupec, Michael A ^a   Arion, Vladimir B ^a   Metzler Nolte, Nils ^b   Keppler, Bernhard K ^a   Hartinger, Christian G ^a,c  

^a UNIVERSITY OF VIENNA   (Austria)

^b RUHR UNIVERSITY BOCHUM   (Germany)

^c UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

antitumor agents; bioorganometallic chemistry; mass spectrometry; peptide bioconjugates; ruthenium complexes

Indexed keywords

ANTI-PROLIFERATIVE ACTIVITIES; ANTI-TUMOR AGENTS; BIO-ORGANOMETALLIC CHEMISTRY; BIOCONJUGATES; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; OVARIAN CARCINOMA CELL; RUTHENIUM COMPLEXES; STRUCTURAL DETERMINANTS;

BIOMOLECULES; CHLORINE COMPOUNDS; CYTOTOXICITY; HYDROCARBONS; MASS SPECTROMETRY; ORGANOMETALLICS; PEPTIDES; RUTHENIUM COMPOUNDS;

RUTHENIUM;

ANTINEOPLASTIC AGENT; COORDINATION COMPOUND; LIGAND; OLIGOPEPTIDE; PYRONE DERIVATIVE; RUTHENIUM; TERPENE; TRIAZOLE DERIVATIVE;

ANTITUMOR AGENTS; ARTICLE; BIOORGANOMETALLIC CHEMISTRY; CHEMISTRY; DRUG SCREENING; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; MASS SPECTROMETRY; PEPTIDE BIOCONJUGATES; RUTHENIUM COMPLEXES; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE; X RAY CRYSTALLOGRAPHY;

ANTITUMOR AGENTS; BIOORGANOMETALLIC CHEMISTRY; MASS SPECTROMETRY; PEPTIDE BIOCONJUGATES; RUTHENIUM COMPLEXES;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; COORDINATION COMPLEXES; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; LIGANDS; MONOTERPENES; OLIGOPEPTIDES; PYRONES; RUTHENIUM; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 84879881791     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201300889     Document Type: Article

References (63)

1. N. Yamamoto, N. S. Bryce, N. Metzler-Nolte, T. W. Hambley, Bioconjugate Chem. 2012, 23, 1110-1118.
2. F. Milletti, Drug Discovery Today 2012, 17, 850-860.
3. C. G. Hartinger, N. Metzler-Nolte, P. J. Dyson, Organometallics 2012, 31, 5677-5685.
4. Q. Geng, X. Sun, T. Gong, Z. R. Zhang, Bioconjugate Chem. 2012, 23, 1200-1210.
5. K. L. Horton, K. M. Stewart, S. B. Fonseca, Q. Guo, S. O. Kelley, Chem. Biol. 2008, 15, 375-382.
6. G. Gasser, N. Metzler-Nolte, Curr. Opin. Chem. Biol. 2012, 16, 84-91.
7. H. B. Albada, F. Wieberneit, I. Dijkgraaf, J. H. Harvey, J. L. Whistler, R. Stoll, N. Metzler-Nolte, R. H. Fish, J. Am. Chem. Soc. 2012, 134, 10321-10324.
8. S. Abramkin, S. M. Valiahdi, M. A. Jakupec, M. Galanski, N. Metzler-Nolte, B. K. Keppler, Dalton Trans. 2012, 41, 3001-3005.
9. S. H. van Rijt, H. Kostrhunova, V. Brabec, P. J. Sadler, Bioconjugate Chem. 2011, 22, 218-226.
10. A. Gross, M. Neukamm, N. Metzler-Nolte, Dalton Trans. 2011, 40, 1382-1386.
11. H. Struthers, T. L. Mindt, R. Schibli, Dalton Trans. 2010, 39, 675-696.
12. K. Splith, W. N. Hu, U. Schatzschneider, R. Gust, I. Ott, L. A. Onambele, A. Prokop, I. Neundorf, Bioconjugate Chem. 2010, 21, 1288-1296.
13. A. Pinto, U. Hoffmanns, M. Ott, G. Fricker, N. Metzler-Nolte, ChemBioChem 2009, 10, 1852-1860.
14. N. Metzler-Nolte, in Topics in Organometallic Chemistry Vol. 32 (Eds:, G. Jaouen, N. Metzler-Nolte,), Springer, Heidelberg, 2009, pp. 195-217.
15. I. Neundorf, J. Hoyer, K. Splith, R. Rennert, H. W. P. N'Dongo, U. Schatzschneider, Chem. Commun. 2008, 5604-5606.
16. M. A. Neukamm, A. Pinto, N. Metzler-Nolte, Chem. Commun. 2008, 232-234.
17. E. García-Garayoa, R. Schibli, P. A. Schubiger, Nucl. Sci. Tech. 2007, 18, 88-100.
18. D. B. Grotjahn, Coord. Chem. Rev. 1999, 190-192, 1125-1141.
19. A. Mooney, A. J. Corry, D. O'Sullivan, K. R. Dilip, P. T. M. Kenny, J. Organomet. Chem. 2009, 694, 886-894.
20. H. W. P. N'Dongo, I. Ott, R. Gust, U. Schatzschneider, J. Organomet. Chem. 2009, 694, 823-827.
21. S. D. Köster, H. Alborzinia, S. Z. Can, I. Kitanovic, S. Wolfl, R. Rubbiani, I. Ott, P. Riesterer, A. Prokop, K. Merz, N. Metzler-Nolte, Chem. Sci. 2012, 3, 2062-2072.
22. L. Gaviglio, A. Gross, N. Metzler-Nolte, M. Ravera, Metallomics 2012, 4, 260-266.
23. F. Barragán, D. Carrion-Salip, I. Gomez-Pinto, A. Gonzalez-Canto, P. J. Sadler, R. de Llorens, V. Moreno, C. Gonzalez, A. Massaguer, V. Marchan, Bioconjugate Chem. 2012, 23, 1838-1855.
24. J. Tauchman, G. Suss-Fink, P. Stepnicka, O. Zava, P. J. Dyson, J. Organomet. Chem. 2013, 723, 233-238.
25. J. Tauchman, B. Therrien, G. Suss-Fink, P. Stepnicka, Organometallics 2012, 31, 3985-3994.
26. A. M. Pizarro, A. Habtemariam, P. J. Sadler, in Medicinal Organometallic Chemistry (Eds:, G. Jaouen, N. Metzler-Nolte,), Springer, Heidelberg, 2010, pp. 21-56.
27. M. A. Santos, Coord. Chem. Rev. 2008, 252, 1213-1224.
28. W. Kandioller, A. Kurzwernhart, M. Hanif, S. M. Meier, H. Henke, B. K. Keppler, C. G. Hartinger, J. Organomet. Chem. 2011, 696, 999-1010.
29. M. Hanif, H. Henke, S. M. Meier, S. Martic, M. Labib, W. Kandioller, M. A. Jakupec, V. B. Arion, H. B. Kraatz, B. K. Keppler, C. G. Hartinger, Inorg. Chem. 2010, 49, 7953-7963.
30. M. G. Mendoza-Ferri, C. G. Hartinger, M. A. Mendoza, M. Groessl, A. E. Egger, R. E. Eichinger, J. B. Mangrum, N. P. Farrell, M. Maruszak, P. J. Bednarski, F. Klein, M. A. Jakupec, A. A. Nazarov, K. Severin, B. K. Keppler, J. Med. Chem. 2009, 52, 916-925.
31. W. Kandioller, C. G. Hartinger, A. A. Nazarov, M. L. Kuznetsov, R. O. John, C. Bartel, M. A. Jakupec, V. B. Arion, B. K. Keppler, Organometallics 2009, 28, 4249-4251.
32. W. Kandioller, C. G. Hartinger, A. A. Nazarov, J. Kasser, R. John, M. A. Jakupec, V. B. Arion, P. J. Dyson, B. K. Keppler, J. Organomet. Chem. 2009, 694, 922-929.
33. W. Kandioller, C. G. Hartinger, A. A. Nazarov, C. Bartel, M. Skocic, M. A. Jakupec, V. B. Arion, B. K. Keppler, Chem. Eur. J. 2009, 15, 12283-12291.
34. A. F. A. Peacock, M. Melchart, R. J. Deeth, A. Habtemariam, S. Parsons, P. J. Sadler, Chem. Eur. J. 2007, 13, 2601-2613.
35. M. Hanif, P. Schaaf, W. Kandioller, M. Hejl, M. A. Jakupec, A. Roller, B. K. Keppler, C. G. Hartinger, Aust. J. Chem. 2010, 63, 1521-1528.
36. J. H. Kasser, W. Kandioller, C. G. Hartinger, A. A. Nazarov, V. B. Arion, P. J. Dyson, B. K. Keppler, J. Organomet. Chem. 2010, 695, 875-881.
37. J. G. Atkinson, Y. Girard, J. Rokach, C. S. Rooney, C. S. Mcfarlane, A. Rackham, N. N. Share, J. Med. Chem. 1979, 22, 99-106.
38. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711
39. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
40. C. W. Tornoe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064.
41. C. F. C. Lam, A. C. Giddens, N. Chand, V. L. Webb, B. R. Copp, Tetrahedron 2012, 68, 3187-3194.
42. S. G. Agalave, S. R. Maujan, V. S. Pore, Chem. Asian J. 2011, 6, 2696-2718.
43. H. Struthers, B. Spingler, T. L. Mindt, R. Schibli, Chem. Eur. J. 2008, 14, 6173-6183.
44. I. A. Papayannopoulos, Mass Spectrom. Rev. 1995, 14, 49-73.
45. L. M. Mikesh, B. Ueberheide, A. Chi, J. J. Coon, J. E. Syka, J. Shabanowitz, D. F. Hunt, Biochim. Biophys. Acta Proteins Proteomics 2006, 1764, 1811-1822.
46. H. Ben Hamidane, D. Chiappe, R. Hartmer, A. Vorobyev, M. Moniatte, Y. O. Tsybin, J. Am. Soc. Mass Spectrom. 2009, 20, 567-575.
47. S. M. Meier, Y. O. Tsybin, P. J. Dyson, B. K. Keppler, C. G. Hartinger, Anal. Bioanal. Chem. 2012, 402, 2655-2662.
48. S. M. Meier, M. Hanif, W. Kandioller, B. K. Keppler, C. G. Hartinger, J. Inorg. Biochem. 2012, 108, 91-95.
49. N. Zhang, Y. Du, M. Cui, J. Xing, Z. Liu, S. Liu, Anal. Chem. 2012, 84, 6206-6212.
50. J. P. Williams, H. I. A. Phillips, I. Campuzano, P. J. Sadler, J. Am. Soc. Mass Spectrom. 2010, 21, 1097-1106.
51. J. P. Williams, J. M. Brown, I. Campuzano, P. J. Sadler, Chem. Commun. 2010, 46, 5458-5460.
52. A. Casini, C. Gabbiani, E. Michelucci, G. Pieraccini, G. Moneti, P. J. Dyson, L. Messori, J. Biol. Inorg. Chem. 2009, 14, 761-770.
53. A. Casini, A. Guerri, C. Gabbiani, L. Messori, J. Inorg. Biochem. 2008, 102, 995-1006.
54. D. Gibson, C. E. Costello, Eur. Mass Spectrom. 1999, 5, 501-510.
55. W. Kandioller, E. Balsano, S. M. Meier, U. Jungwirth, S. Goschl, A. Roller, M. A. Jakupec, W. Berger, B. K. Keppler, C. G. Hartinger, Chem. Commun. 2013, 49, 3348-3350.
56. L. Konermann, D. J. Douglas, Biochemistry 1997, 36, 12296-12302.
57. M. A. Bennett, A. K. Smith, J. Chem. Soc. Dalton Trans. 1974, 233-241.
58. M. A. Bennett, T. N. Huang, T. W. Matheson, A. K. Smith, Inorg. Synth. 1982, 21, 74-78.
59. M. R. Pressprich, J. Chambers, SAINT+Integration Engine, Program for Crystal Structure Integration, Bruker Analytical X-ray systems, Madison, 2004.
60. G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen (Germany), 1997.
61. C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, P. A. Wood, J. Appl. Crystallogr. 2008, 41, 466-470.
62. D. R. van Staveren, N. Metzler-Nolte, Chem. Commun. 2002, 1406-1407.
63. S. D. Köster, J. Dittrich, G. Gasser, N. Husken, I. C. H. Castaneda, J. L. Jios, C. O. Della Vedova, N. Metzler-Nolte, Organometallics 2008, 27, 6326-6332.