Excellent correlation between drug release and portal size in metalla-cage drug-delivery systems

Chemistry - A European Journal

Volumn 17, Issue 35, 2011, Pages 9669-9677

  Barry, Nicolas P E ^a   Zava, Olivier ^b   Dyson, Paul J ^b   Therrien, Bruno ^a  

^a UNIVERSITY OF NEUCHÂTEL   (Switzerland)

^b EPFL   (Switzerland)

Author keywords

bioorganometallic chemistry; drug delivery; endocytosis; host guest systems; ruthenium

Indexed keywords

BIO-ORGANOMETALLIC CHEMISTRY; BUILDING BLOCKES; CANCER CELLS; DELIVERY SYSTEMS; DRUG RELEASE; DRUG-DELIVERY SYSTEMS; ENDOCYTOSIS; GUEST MOLECULES; HOST-GUEST SYSTEM; HOST-GUESTS; STABILITY CONSTANTS; UPTAKE MECHANISM;

DRUG DELIVERY; FLUORESCENCE SPECTROSCOPY; MOLECULAR BIOLOGY; PALLADIUM;

RUTHENIUM;

4-CYMENE; ANTINEOPLASTIC AGENT; LIGAND; ORGANOMETALLIC COMPOUND; PARA CYMENE; PYRENE DERIVATIVE; RUTHENIUM; TERPENE; TRIAZINE DERIVATIVE; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DELIVERY SYSTEM; DRUG EFFECT; ENDOCYTOSIS; HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG DELIVERY SYSTEMS; ENDOCYTOSIS; HUMANS; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; MONOTERPENES; ORGANOMETALLIC COMPOUNDS; PYRENES; RUTHENIUM; TRIAZINES; WATER;

EID: 80051730152     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201003530     Document Type: Article

References (80)

1. W. M. Nau, Nat. Chem. 2010, 2, 248-250
2. K. K. Cotí, M. E. Belowich, M. Liong, M. W. Ambrogio, Y. A. Lau, H. A. Khatib, J. I. Zink, N. M. Khashab, J. F. Stoddart, Nanoscale 2009, 1, 16-39
3. G. Wenz, Clin. Drug Invest. 2000, 19, 21-25.
4. M. Vallet-Regí, F. Balas, D. Arcos, Angew. Chem. 2007, 119, 7692-7703
5. Angew. Chem. Int. Ed. 2007, 46, 7548-7558
6. E. Gabano, M. Ravera, D. Osella, Curr. Med. Chem. 2009, 16, 4544-4580.
7. P. J. Dyson, G. Sava, Dalton Trans. 2006, 1929-1933
8. S. H. van Rijt, P. J. Sadler, Drug Discovery Today 2009, 14, 1089-1097
9. C. Sanchez-Cano, M. J. Hannon, Dalton Trans. 2009, 10702-10711.
10. T. Boulikas, M. Vougiouka, Oncol. Rep. 2003, 10, 1663-1682
11. K. S. Lovejoy, S. J. Lippard, Dalton Trans. 2009, 10651-10659.
12. N. W. Shi Kam, T. C. Jessop, P. A. Wender, H. Dai, J. Am. Chem. Soc. 2004, 126, 6850-6851.
13. Z. Yang, X. Wang, H. Diao, J. Zhang, H. Li, H. Sun, Z. Guo, Chem. Commun. 2007, 3453-3455.
14. A. M. Krause-Heuer, N. J. Wheate, M. J. Tilby, D. G. Pearson, C. J. Ottley, J. R. Aldrich-Wright, Inorg. Chem. 2008, 47, 6880-6888
15. N. J. Wheate, A. I. Day, R. J. Blanch, A. P. Arnold, C. Cullinane, J. G. Collins, Chem. Commun. 2004, 1424-1425
16. N. J. Wheate, D. P. Buck, A. I. Day, J. G. Collins, Dalton Trans. 2006, 451-458
17. N. J. Wheate, R. I. Taleb, A. M. Krause-Heuer, R. L. Cook, S. Wang, V. J. Higgins, J. R. Aldrich-Wright, Dalton Trans. 2007, 5055-5064.
18. J. M. Rademaker-Lakhai, C. Terret, S. B. Howell, C. M. Baud, R. F. de Boer, D. Pluim, J. H. Beijnen, J. H. M. Schellens, J. P. Droz, Clin. Cancer Res. 2004, 10, 3386-3395
19. M. Campone, J. M. Rademaker-Lakhai, J. Bennouna, S. B. Howell, D. P. Nowotnik, J. H. Beijnen, J. H. M. Schellens, Cancer Chemother. Pharmacol. 2007, 60, 523-533
20. P. Govender, N. C. Antonels, J. Mattsson, A. K. Renfrew, P. J. Dyson, J. R. Moss, B. Therrien, G. S. Smith, J. Organomet. Chem. 2009, 694, 3470-3476.
21. Y. Matsumura, H. Maeda, Cancer Res. 1986, 46, 6387-6392.
22. M. Fujita, M. Tominaga, A. Hori, B. Therrien, Acc. Chem. Res. 2005, 38, 369-380
23. B. H. Northrop, Y.-R. Zheng, K.-W. Chi, P. J. Stang, Acc. Chem. Res. 2009, 42, 1554-1563.
24. F. A. Cotton, C. Y. Liu, C. A. Murillo, X. Wang, Inorg. Chem. 2006, 45, 2619-2626
25. M. D. Ward, Chem. Commun. 2009, 4487-4499
26. C. Desmarets, F. Poli, X. F. Le Goff, K. Müller, H. Amouri, Dalton Trans. 2009, 10429-10432
27. M. D. Pluth, R. G. Bergman, K. N. Raymond, Acc. Chem. Res. 2009, 42, 1650-1659
28. S. J. Dalgarno, N. P. Power, J. L. Atwood, Coord. Chem. Rev. 2008, 252, 825-841
29. A. Granzhan, T. Riis-Johannessen, R. Scopelliti, K. Severin, Angew. Chem. 2010, 122, 5647-5650
30. Angew. Chem. Int. Ed. 2010, 49, 5515-5518
31. W. Meng, B. Breiner, K. Rissanen, J. D. Thoburn, J. K. Clegg, J. R. Nitschke, Angew. Chem. 2011, 123, 3541-3545
32. Angew. Chem. Int. Ed. 2011, 50, 3479-3483.
33. J. I. van der Vlugt, T. S. Koblenz, J. Wassenaar, J. N. H. Reek, in Molecular Encapsulation (Eds.:, U. H. Brinker, J.-L. Mieusset,), Wiley, New York, 2010, pp. 145-174
34. J.-L. Mieusset, U. H. Brinker, in Molecular Encapsulation (Eds.:, U. H. Brinker, J.-L. Mieusset,), Wiley, New York, 2010, pp. 269-308
35. M. Yoshizawa, J. K. Klosterman, M. Fujita, Angew. Chem. 2009, 121, 3470-3490
36. Angew. Chem. Int. Ed. 2009, 48, 3418-3438
37. M. Wang, V. Vajpayee, S. Shanmugaraju, Y.-R. Zheng, Z. Zhao, H. Kim, P. S. Mukherjee, K.-W. Chi, P. J. Stang, Inorg. Chem. 2011, 50, 1506-1512.
38. A. V. Davis, K. N. Raymond, J. Am. Chem. Soc. 2005, 127, 7912-7919
39. M. D. Pluth, K. N. Raymond, Chem. Soc. Rev. 2007, 36, 161-171.
40. W. Han Ang, P. J. Dyson, Eur. J. Inorg. Chem. 2006, 4003-4018
41. A. F. A. Peacock, P. J. Sadler, Chem. Asian J. 2009, 4, 1890-1899
42. A. Levina, A. Mitra, P. A. Lay, Metallomics 2009, 1, 458-470
43. G. Süss-Fink, Dalton Trans. 2010, 39, 1673-1688.
44. T. B. Rauchfuss, K. Severin, in Organic Nanostructures (Eds.:, J. L. Atwood, J. W. Steed,), Wiley-VCH, Weinheim, 2008, pp. 179-203
45. B. Therrien, Eur. J. Inorg. Chem. 2009, 2445-2453
46. Y.-F. Han, W.-G. Jia, W.-B. Yu, G.-X. Jin, Chem. Soc. Rev. 2009, 38, 3419-3434.
47. J. Mattsson, P. Govindaswamy, J. Furrer, Y. Sei, K. Yamaguchi, G. Süss-Fink, B. Therrien, Organometallics 2008, 27, 4346-4356
48. P. Govindaswamy, J. Furrer, G. Süss-Fink, B. Therrien, Z. Anorg. Allg. Chem. 2008, 634, 1349-1352
49. J. Mattsson, O. Zava, A. K. Renfrew, Y. Sei, K. Yamaguchi, P. J. Dyson, B. Therrien, Dalton Trans. 2010, 39, 8248-8255
50. A. Pitto-Barry, N. P. E. Barry, O. Zava, R. Deschenaux, P. J. Dyson, B. Therrien, Chem. Eur. J. 2011, 17, 1966-1971.
51. B. Therrien, G. Süss-Fink, P. Govindaswamy, A. K. Renfrew, P. J. Dyson, Angew. Chem. 2008, 120, 3833-3836
52. Angew. Chem. Int. Ed. 2008, 47, 3773-3776.
53. O. Zava, J. Mattsson, B. Therrien, P. J. Dyson, Chem. Eur. J. 2010, 16, 1428-1431.
54. N. P. E. Barry, B. Therrien, Eur. J. Inorg. Chem. 2009, 4695-4700.
55. J. Freudenreich, N. P. E. Barry, G. Süss-Fink, B. Therrien, Eur. J. Inorg. Chem. 2010, 2400-2405.
56. I. Mathew, Y. Li, Z. Li, W. Sun, Dalton Trans. 2010, 39, 11201-11209.
57. D. Astruc, Chimie Organométallique, EDP Sciences, Les Ulis, 2000, pp. 31-54.
58. A. Pitto-Barry, N. P. E. Barry, O. Zava, R. Deschenaux, B. Therrien, Chem. Asian J. 2011, 6, 1595-1603.
59. D. Wu, A. Chen, C. S. Johnson, Jr., J. Magn. Reson. Ser. A. 1995, 115, 123-126
60. C. S. Johnson, Jr., Prog. Nucl. Magn. Reson. Spectrosc. 1999, 34, 203-256
61. D. Ajami, J. Rebek, Jr., Angew. Chem. 2007, 119, 9443-9446
62. Angew. Chem. Int. Ed. 2007, 46, 9283-9286
63. J.-F. Lemonnier, S. Floquet, A. Kachmar, M.-M. Rohmer, M. Bénard, J. Marrot, E. Terazzi, C. Piguet, E. Cadot, Dalton Trans. 2007, 3043-3054
64. N. P. E. Barry, J. Furrer, J. Freudenreich, G. Süss-Fink, B. Therrien, Eur. J. Inorg. Chem. 2010, 725-728
65. N. P. E. Barry, J. Furrer, B. Therrien, Helv. Chim. Acta 2010, 93, 1313-1328.
66. Y. Tsukube, H. Furuta, A. Odani, Y. Takeda, Y. Kudo, Y. Inoue, Y. Liu, H. Sakamoto, K. Kimura, in Comprehensive Supramolecular Chemistry (Eds.:, J. L. Atwood, J. E. D. Davies, D. D. Macnicol, F. Vögtle,), Pergamon Press, Oxford, 1996, pp. 425-482.
67. M. J. Hynes, J. Chem. Soc. Dalton Trans. 1993, 311-312.
68. N. Bouquin, V. L. Malinovskii, R. Häner, Chem. Commun. 2008, 1974-1976.
69. HyperChem Computational Chemistry Software Package Version 7.5, Hypercube Inc., Gainesville, Florida (2003).
70. A. C. Eifler, C. S. Thaxton, Methods Mol. Biol. 2011, 726, 325-338.
71. R. Kjeken, S. A. Mousavi, A. Brech, G. Griffiths, T. Berg, Biochem. J. 2001, 357, 497-503.
72. S. Falcone, E. Cocucci, P. Podini, T. Kirchhausen, E. Clementi, J. Meldolesi, J. Cell Sci. 2006, 119, 4758-4769.
73. C. A. Puckett, J. K. Barton, J. Am. Chem. Soc. 2009, 131, 8738-8739.
74. W. I. Lencer, P. Weyer, A. S. Verkman, D. A. Ausiello, D. Brown, Am. J. Physiol. 1990, 258, C 309 -C 317.
75. H. L. Anderson, S. Anderson, J. K. M. Sanders, J. Chem. Soc. Perkin Trans. 1 1995, 2231-2245.
76. F. Kühlwein, K. Polborn, W. Beck, Z. Anorg. Allg. Chem. 1997, 623, 1931-1944.
77. TopSpin Software, Version 2.0, Bruker BioSpin, Rheinstetten, 2005.
78. Origin Scientific Graphing and Data Analysis Software, Version 7.5, OriginLab, Northampton, 2006.
79. Zen Software, Carl Zeiss MicroImaging, Germany, 2007.
80. FlowJo Software, Version 8.0 for the Analysis of Flow Cytometry Data, Tree Star, Stanford, 2006.