Review

Advances in Ru(II)-based Photoactivated Chemotherapy Agents

  • Zhou Qianxiong ,
  • Wang Xuesong
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  • Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190

Received date: 2016-09-05

  Revised date: 2016-10-09

  Online published: 2016-10-10

Supported by

Project supported by the National Natural Science Foundation of China (Grant Nos. 21273259, 21571181).

Abstract

Many Ru(II) complexes can undergo photoinduced ligand dissociation in aqueous solutions, and the formed aqua Ru(II) species may bind to DNA covalently. This property has been applied to develop novel photoactivated chemotherapy (PACT) agents for cancer treatment in recent years. By finely tuning ligand structures and coordination configurations, PACT may realize highly selective and on-demand release of active species in cancer tissues, leading to an improved efficacy and diminished side effects. In this review, the progress in Ru(II)-based PACT agents was fully discussed and a perspective for their future development was included.

Cite this article

Zhou Qianxiong , Wang Xuesong . Advances in Ru(II)-based Photoactivated Chemotherapy Agents[J]. Acta Chimica Sinica, 2017 , 75(1) : 49 -59 . DOI: 10.6023/A16090470

References

[1] Romero-Canelón, I.; Sadler, P. J. Inorg. Chem. 2013, 52, 12276.
[2] Mjos, K. D.; Orvig, C. Chem. Rev. 2014, 114, 4540.
[3] Gaynor, D.; Griffith, D. M. Dalton Trans. 2012, 41, 13239.
[4] Liu, Y.; Chen, X.; Zhang, L.; Sun, D.; Zhou, Y.; Chen, L.; Liu, J. Acta Chim. Sinica 2014, 72, 473 (in Chinese). (刘莹, 陈小曼, 张郎棋, 孙冬冬, 周艳晖, 陈兰美, 刘杰, 化学学报, 2014, 72, 473.)
[5] Zhou, S.; Xue, X.; Jiang, B.; Lu, C.; Tian, Y.; Jiang, M. Acta Chim. Sinica 2011, 69, 2335 (in Chinese). (周双生, 薛璇, 姜波, 鲁传华, 田玉鹏, 蒋明华, 化学学报, 2011, 69, 2335.)
[6] Xia, Q.; He, Q.; Xu, D.; Li, X.; Sun, D. Acta Chim. Sinica 2010, 68, 775 (in Chinese). (夏庆春, 何其庄, 许东芳, 李兴玉, 孙大志, 化学学报, 2010, 68, 775.)
[7] Yin, F.-L.; Shen, J.; Zou, J.-J.; Li, R.-C.; Acta Chim. Sinica 2003, 61, 556 (in Chinese). (尹富玲, 申佳, 邹佳嘉, 李荣昌, 化学学报, 2003, 61, 556.)
[8] Rosenberg, B.; Vancamp, L.; Krigas, T. Nature 1965, 205, 698.
[9] Rosenberg, B.; VanCamp, L.; Trosko, J. E.; Mansour, V. H. Nature 1969, 222, 385.
[10] Wheate, N. J.; Walker, S.; Craig, G. E.; Oun, R. Dalton Trans. 2010, 39, 8113.
[11] Bugar?i?, ?. D.; Bogojeski, J.; Petrovi?, B.; Hochreuther, S.; van Eldik, R. Dalton Trans. 2012, 41, 12329.
[12] Fanelli, M.; Formica, M.; Fusi, V.; Giorgi, L.; Micheloni, M.; Paoli, P. Coord. Chem. Rev. 2016, 310, 41.
[13] Johnstone, T. C.; Suntharalingam, K.; Lippard, S. J. Chem. Rev. 2016, 116, 3436.
[14] Mackay, F. S.;Woods, J. A.; Heringova, P.; Kašpárková, J.; Pi-zarro, A. M.; Moggach, S. A.; Parsons, S.; Brabec, V.; Sadler, P. J. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 20743.
[15] Farrer, N. J.; Woods, J. A.; Salassa, L.; Zhao, Y.; Robinson, K. S.; Clarkson, G.; Mackay, F. S.; Sadler, P. J. Angew. Chem. Int. Ed. 2010, 49, 8905.
[16] Kasparkova, J.; Kostrhunova, H.; Novakova, O.; K?ikavová, R.; Van?o, J.; Trávní?k, Z.; Brabec, V. Angew. Chem. Int. Ed. 2015, 54, 14478.
[17] Glazer, E. C. Isr. J. Chem. 2013, 53, 391.
[18] Farrer, N. J.; Salassa, L.; Sadler, P. J. Dalton Trans. 2009, 10690.
[19] Detty, M. R.; Gibson, S. L.; Wagner, S. J. J. Med. Chem. 2004, 47, 3897.
[20] Brown, J. M.; Wilson, W. R. Nat. Rev. Cancer 2004, 4, 437.
[21] Minchinton, A. I.; Tannock, I. F. Nat. Rev. Cancer 2006, 6, 583.
[22] Knoll, J. D.; Turro, C. Coord. Chem. Rev. 2015, 282-283, 110.
[23] Gianferrara, T.; Bratsos, I.; Alessio, E. Dalton Trans. 2009, 7588.
[24] Lincoln, R.; Kohler, L.; Monro, S.; Yin, H.; Stephenson, M.; Zong, R.; Chouai, A.; Dorsey, C.; Hennigar, R.; Thummel, R. P.; McFarland, S. A. J. Am. Chem. Soc. 2013, 135, 17161.
[25] Sun, Y.; Joyce, L. E.; Dickson, N. M.; Turro, C. Chem. Commun. 2010, 46, 2426.
[26] Zhou, Q. X.; Lei, W. H.; Chen, J. R.; Li, C.; Hou, Y. J.; Wang, X. S.; Zhang, B. W. Chem.-Eur. J. 2010, 16, 3157.
[27] Zhou, Q. X.; Lei, W. H.; Sun, Y.; Chen, J. R.; Li, C.; Hou, Y. J.; Wang, X. S.; Zhang, B. W. Inorg. Chem. 2010, 49, 4729.
[28] Zhou, Q. X.; Yang, F.; Lei, W. H.; Chen, J. R.; Li, C.; Hou, Y. J.; Ai, X. C.; Zhang, J. P.; Wang, X. S.; Zhang, B. W. J. Phys. Chem. B 2009, 113, 11521.
[29] Liu, Y.; Hammitt, R.; Lutterman, D. A.; Joyce, L. E.; Thummel, R. P.; Turro, C. Inorg. Chem. 2009, 48, 375.
[30] Poteet, S. A.; Majewski, M. B.; Breitbach, Z. S.; Griffith, C. A.; Singh, S.; Armstrong, D. W.; Wolf, M. O.; MacDonnell, F. M. J. Am. Chem. Soc. 2013, 135, 2419.
[31] Vanderlinden, W.; Blunt, M.; David, C. C.; Moucheron, C.; Kirsch-De Mesmaeker, A.; De Feyter, S. J. Am. Chem. Soc. 2012, 134, 10214.
[32] Boggio-Pasqua, M.; Vicendo, P.; Oubal, M.; Alary, F.; Heully, J.-L. Chem.-Eur. J. 2009, 15, 2759.
[33] Lecomte, J.-P.; Kirsch-De Mesmaeker, A.; Feeney, M. M.; Kelly, J. M. Inorg. Chem. 1995, 34, 6481.
[34] Zayat, L.; Calero, C.; Alborés P.; Baraldo, L.; Etchenique, R. J. Am. Chem. Soc. 2003, 125, 882.
[35] Bonnet, S.; Limburg, B.; Meeldijk, J. D.; Klein Gebbink, R. J. M.; Killian, J. A. J. Am. Chem. Soc. 2011, 133, 252.
[36] Respondek, T.; Garner, R. N.; Herroon, M. K.; Podgorski, I.; Turro, C.; Kodanko, J. J. J. Am. Chem. Soc. 2011, 133, 17164.
[37] Miguel, V. S.; Álvarez, M.; Filevich, O.; Etchenique, R.; del Campo, A. Langmuir 2012, 28, 1217.
[38] Mosquera, J.; Sánchez, M. R.; Mascareñas, J. L.; Vázquez, M. E. Chem. Commun. 2015, 51, 5501.
[39] Nakanishi, K.; Koshiyama, T.; Iba, S.; Ohba, M. Dalton Trans. 2015, 44, 14200.
[40] Griepenburg, J. C.; Rapp, T. L.; Carroll, P. J.; Eberwineb, J.; Dmochowski, I. J. Chem. Sci. 2015, 6, 2342.
[41] Li, A.; White, J. K.; Arora, K.; Herroon, M. K.; Martin, P. D.; Bernhard Schlegel, H.; Podgorski, I.; Turro, C.; Kodanko, J. J. Inorg. Chem. 2016, 55, 10.
[42] Sharma, R.; Knoll, J. D.; Ancona, N.; Martin, P. D.; Turro, C.; Kodanko, J. J. Inorg. Chem. 2015, 54, 1901.
[43] Ford, P. C. Coord. Chem. Rev. 1982, 44, 61.
[44] Tfouni, E. Coord. Chem. Rev. 2000, 196, 281.
[45] Van Houten, J.; Watts, R. J. Inorg. Chem. 1978, 17, 3381.
[46] Durante, V. A.; Ford, P. C. Inorg. Chem. 1979, 18, 588.
[47] Singh, T. N.; Turro, C. Inorg. Chem. 2004, 43, 7260.
[48] Rillema, D. P.; Blanton, C. B.; Shaver, R. J.; Jackman, D. C.; Boldaji, M.; Bundy, S.; Worl, L. A.; Meyer, T. J. Inorg. Chem. 1992, 31, 1600.
[49] Liu, Y.; Turner, D. B.; Singh, T. N.; Angeles-Boza, A. M.; Chouai, A.; Dunbar, K. R.; Turro, C. J. Am. Chem. Soc. 2009, 131, 26.
[50] Arora, K.; White, J. K. Sharma, R.; Mazumder, S.; Martin, P. D.; Schlegel, H. B.; Turro, C.; Kodanko, J. K. Inorg. Chem. 2016, 55, 6968.
[51] Knoll, J. D.; Albani, B. A.; Durr, C. B.; Turro, C. J. Phys. Chem. A 2014, 118, 10603.
[52] Albani, B. A.; Durr, C. B.; Turro, C. J. Phys. Chem. A 2013, 117, 13885.
[53] Garner, R. N.; Joyce, L. E.; Turro, C. Inorg. Chem. 2011, 50, 4384.
[54] Howerton, B. S.; Heidary, D. K.; Glazer, E. C. J. Am. Chem. Soc. 2012, 134, 8324.
[55] Hidayatullah, A. N.; Wachter, E.; Heidary, D. K.; Parkin, S.; Glazer, E. C. Inorg. Chem. 2014, 53, 10030.
[56] Wachter, E.; Heidary, D. K.; Howerton, B. S.; Parkin, S.; Glazer, E. C. Chem. Commun. 2012, 48, 9649.
[57] Dickerson, M.; Howerton, B.; Baeb, Y.; Glazer, E. C. J. Mater. Chem. B 2016, 4, 394.
[58] Friedman, A. E.; Chambron, J.-C.; Sauvage, J.-P.; Turro, N. J.; Barton, J. K. J. Am. Chem. Soc. 1990, 112, 4960.
[59] Wachter, E.; Howerton, B. S.; Hall, E. C.; Parkin, S.; Glazer, E. C. Chem. Commun. 2014, 50, 311.
[60] Wachter, E.; Glazer, E. C. J. Phys. Chem. A 2014, 118, 10474.
[61] Wachter, E.; Moyá, D.; Parkin, S.; Glazer, E. C. Chem.-Eur. J. 2016, 22, 550.
[62] Cleare, M. J.; Hoeschele, J. D. Bioinorg. Chem. 1973, 2, 187.
[63] Farrell, N. Transition Metal Complexes as Drugs and Chemotherapeutic Agents, Kluwer, Dordrecht, Netherlands, 1989.
[64] Van Rixel, V. H. S; Siewert, B.; Hopkins, S. L.; Askes, S. H. C.; Busemann, A.; Siegler, M. A.; Bonnet, S. Chem. Sci. 2016, 7, 4922.
[65] Wachter, E.; Zamora, A.; Heidary, D. K.; Ruizb, J.; Glazer, E. C. Chem. Commun. 2016, 52, 10121.
[66] D?browski, J. M.; Arnaut, L. G. Photochem. Photobiol. Sci. 2015, 14, 1765.
[67] Sears, R. B.; Joyce, L. E.; Ojaimi, M.; Gallucci, J. C.; Thummel, R. P.; Turro, C. J. Inorg. Biochem. 2013, 121, 77.
[68] Albani, B. A.; Peña, B.; Dunbar, K. R.; Turro, C. Photochem. Photobiol. Sci. 2014, 13, 272.
[69] Huang, H.; Zhang, P.; Chen, Y.; Ji, L.; Chao, H. Dalton Trans. 2015, 44, 15602.
[70] Ruminski, R. R.; Degroff, C.; Smith, S. J. Inorg. Chem. 1992, 31, 3325.
[71] Rillema, D. P.; Mack, K. B. Inorg. Chem. 1982, 21, 3849.
[72] Ernst, S.; Kasack, V.; Kaim, W. Inorg. Chem. 1988, 27, 1146.
[73] Albani, B. A.; Peña, B.; Saha, S.; White, J. K.; Schaeffer, A. M.; Dunbar, K. R.; Turro, C. Chem. Commun. 2015, 51, 16522.
[74] Chen, Y.; Jiang, G.; Zhou, Q.; Zhang, Y.; Li, K.; Zheng, Y.; Zhang, B.; Wang, X. RSC Adv. 2016, 6, 23804.
[75] Greenough, S. E.; Horbury, M. D.; Smith, N. A.; Sadler, P. J.; Paterson, M. J.; Stavros, V. G. ChemPhysChem 2016, 17, 221.
[76] Albani, B. A.; Peña, B.; Leed, N. A.; Paula, N. A. B. G. D.; Pavani, C.; Baptista, M. S.; Dunbar, K. R.; Turro, C. J. Am. Chem. Soc. 2014, 136, 17095.
[77] Knoll, J. D.; Albani, B. A.; Turro, C. Chem. Commun. 2015, 51, 8777.
[78] Knoll, J. D.; Albani, B. A.; Turro, C. Acc. Chem. Res. 2015, 48, 2280.
[79] Loftus, L. M.; White, J. K.; Albani, B. A.; kohler, L.; Kodanko, J. K.; Thummel, R. P.; Dunba, K. R.; Turro, C. Chem.-Eur. J. 2016, 22, 3704.
[80] Zheng, Y.; Zhou, Q.-X.; Lei, W.-H.; Hou, Y.-J.; Li, K.; Chen, Y.-J.; Zhang, B.-W.; Wang, X.-S. Chem. Commun. 2015, 51, 428.
[81] Zheng, Y.; Zhou, Q.-X.; Zhang, Y.-Y.; Li, C.; Hou, Y.-J.; Wang, X.-S. Dalton Trans. 2016, 45, 2897.
[82] Gamer, B. N.; Gallucci, J. C.; Dunbar, K. R.; Turro, C. Inorg. Chem. 2011, 50, 9213.
[83] Sgambellone, M. A.; David, A.; Garner, R. N.; Dunbar, K. R.; Turro, C. J. Am. Chem. Soc. 2013, 135, 11274.
[84] Respondek, T.; Garmer, R. N.; Herroon, M. K.; Podgorski, I.; Turro, C.; Kodanko, J. J. J. Am. Chem. Soc. 2011, 133, 17164.
[85] Respondek, T.; Sharma, R.; Herroon, M. K.; Garmer, R. N.; Knoll, J. D.; Cueny, E.; Turro, C.; Podgorski, I.; Kodanko, J. J. ChemMedChem 2014, 9, 1306.
[86] Ramalho, S. D.; Sharma, R.; White, J. K.; Aggarwal, N.; Chalasani, A.; Sameni, M.; Moin, K.; Vieira, P. C.; Turro, C.; Kodanko, J. J.; Sloane, B. F. Plos One 2015, DOI:10.1371/journal.pone.0142527
[87] Zhou, Q.-X.; Zheng, Y.; Wang, T.-J.; Chen, Y.-J.; Li, K.; Zhang, Y.-Y.; Li. C.; Hou, Y.-J.; Wang, X.-S. Chem. Commun. 2015, 51, 10684.
[88] Magennis, S. W.; Habtemariam, A.; Novakova, O.; Henry, J. B.; Meier, S.; Parsons, S.; Oswald, L. D. H.; Brabec, V.; Sadler, P. J. Inorg. Chem. 2007, 46, 5059.
[89] Betanzos-Lara, S.; Salassa, L.; Habtemariam, A.; Sadler, P. J. Chem. Commun. 2009, 43, 6622.
[90] Barragán, F.; López-Senín, P.; Salassa, L.; Betanzos-Lara, S.; Habtemariam, A.; Moreno, V.; Sadler, P. J.; Marchán, V. J. Am. Chem. Soc. 2011, 133, 14098.
[91] Zhou, Q.-X.; Lei, W.-H.; Hou, Y.-J.; Chen, Y.-J.; Li, C.; Zhang, B.-W.; Wang, X.-S. Dalton Trans. 2013, 42, 2786.
[92] Wang, T.-J.; Zhou, Q.-X.; Zhang, Y.-Y.; Zheng, Y.; Wang, W.-B.; Hou, Y.-J.; Jiang, G.-Y.; Cheng, X.-X.; Wang, X.-S. RSC Adv. 2016, 6, 45652.
[93] Chen, Y.-J.; Lei, W.-H.; Jiang, G.-Y.; Hou, Y.-J.; Li, C.; Zhang, B.-W.; Zhou, Q.-X.; Wang, X.-S. Dalton Trans. 2014, 43, 15375.
[94] Chen, Y.-J.; Lei, W.-H.; Hou, Y.-J.; Li, C.; Jiang, G.-Y.; Zhang, B.-W.; Zhou, Q.-X.; Wang, X.-S. Dalton Trans. 2015, 44, 7347.
[95] Chen, Y.-M.; Jiang, G.-Y.; Wang, X.-S. Imaging Sci. Photochem. 2016, 34, 297 (in Chinese). (陈雨濛, 姜国玉, 王雪松, 影像科学与光化学, 2016, 34, 297.)

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