The Library
Arene control over thiolate to sulfinate oxidation in albumin by organometallic ruthenium anticancer complexes
Tools
Hu, Wenbing, Luo, Qun, Ma, Xiaoyan, Wu, Kui, Liu, Jianan, Chen, Yi, Xiong, Shaoxiang, Wang, Jianping, Sadler, P. J. and Wang, Fuyi. (2009) Arene control over thiolate to sulfinate oxidation in albumin by organometallic ruthenium anticancer complexes. Chemistry - A European Journal, Vol.15 (No.27). pp. 6586-6594. ISSN 0947-6539
Full text not available from this repository.
Official URL: http://dx.doi.org/10.1002/chem.200900699
Abstract
Interactions of organometallic ruthenium anticancer complexes [Ru(eta(6)-arcne)Cl(en)][PF6] (arene = p-cymene (1) or biphenyl (2), en=ethylenediamine) with human serum albumin were investigated by means of mass spectrometry combined with trypsin digestion, specific sidechain modifications and computational modelling. Both complexes were shown to bind to surface histidine (His128, His247, His510) and methionine (Met298) residues in human albumin, but only the p-cymene complex can gain entry to the crevice containing the free cysteine thiolate (Cys34) and induce oxidation to sulfinate. The two complexes exhibit a similar coordination preference for histidine and methionine residues on the protein surface. His128 binding is favoured both kinetically and thermodynamically. At 310 K, six days of incubation of recombinant human albumin (rHA) with complex I (rHA:Ru 50:250 pm) led to about 18% ruthenation of His128 in the protein. However, the extent of ruthenation of albumin by complex 2 was less than that by I., due to the steric hindrance from the biphenyl ligand. These results imply that the arene ligand in the organometallic ruthenium anticancer complexes plays a crucial role in interactions with proteins.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry Q Science > QP Physiology |
| Divisions: | Faculty of Science > Chemistry |
| Library of Congress Subject Headings (LCSH): | Ruthenium, Mass spectrometry, Antineoplastic agents, Bioorganic chemistry, Albumins |
| Journal or Publication Title: | Chemistry - A European Journal |
| Publisher: | Wiley - V C H Verlag GmbH & Co. KGaA |
| ISSN: | 0947-6539 |
| Date: | 6 July 2009 |
| Volume: | Vol.15 |
| Number: | No.27 |
| Number of Pages: | 9 |
| Page Range: | pp. 6586-6594 |
| Identification Number: | 10.1002/chem.200900699 |
| Status: | Peer Reviewed |
| Publication Status: | Published |
| Access rights to Published version: | Restricted or Subscription Access |
| Funder: | Guo jia zi ran ke xue ji jin wei yuan hui (China) [National Natural Science Foundation (China)] (NSFC), Zhongguo ke xue yuan [Chinese Academy of Sciences], National Basic Research Program of China (973 Program) |
| Grant number: | 20745002 (NSFC), 20773136 (NSFC), 90713020 (NSFC), 2007CB (NSFC), 935601 (NBRPC) |
| References: | [1] D. C. Carter, J. X. Ho, Adv. Protein Chem. 1994, 45, 153 –203. [2] A. R. Timerbaev, C. G. Hartinger, S. S. Aleksenko, B. K. Keppler, Chem. Rev. 2006, 106, 2224 –2248. [3] B. P. Esposito, R. Najjar, Coord. Chem. Rev. 2002, 232, 137 –149. [4] E. I. Montero, B. T. Benedetti, J. B. Mangrum, M. J. Oehlsen, Y. Qu, N. P. Farrell, Dalton Trans. 2007, 4938 –4942. [5] W. H. Ang, E. Daldini, L. Juillerat-Jeanneret, P. J. Dyson, Inorg. Chem. 2007, 46, 9048 –9050. [6] A. I. Ivanov, J. Christodoulou, J. A. Parkinson, K. J. Barnham, A. Tucker, J. Woodrow, P. J. Sadler, J. Biol. Chem. 1998, 273, 14721 – 14730. [7] J. Will, D. A. Wolters, W. S. Sheldrick, ChemMedChem 2008, 3, 1696 – 1707. [8] M. A. Jakupec, M. Galanski, V. B. Arion, C. G. Hartinger, B. K. Keppler, Dalton Trans. 2008, 183 –194. [9] F. Y. Wang, A. Habtemariam, E. P. L. van der Geer, R. Fernandez, M. Melchart, R. J. Deeth, R. Aird, S. Guichard, F. P. A. Fabbiani, P. Lozano-Casal, I. D. H. Oswald, D. I. Jodrell, S. Parsons, P. J. Sadler, Proc. Natl. Acad. Sci. USA 2005, 102, 18269 –18274. [10] P. C. A. Bruijnincx, P. J. Sadler, Curr. Opin. Chem. Biol. 2008, 12, 197 – 206. [11] X. M. He, D. C. Carter, Nature 1992, 358, 209 – 215. [12] R. H. L. Marks, R. D. Miller, Biochem. Biophys. Res. Commun. 1979, 88, 661 –667. [13] R. E. Morris, R. E. Aird, P. D. Murdoch, H. M. Chen, J. Cummings, N. D. Hughes, S. Parsons, A. Parkin, G. Boyd, D. I. Jodrell, P. J. Sadler, J. Med. Chem. 2001, 44, 3616 –3621. [14] A. Casini, A. Guerri, C. Gabbiani, L. Messori, J. Inorg. Biochem. 2008, 102, 995 –1006. [15] J. Will, A. Kyas, W. S. Sheldrick, J. Biol. Inorg. Chem. 2007, 12, 883 – 894. [16] C. S. Allardyce, P. J. Dyson, J. Coffey, N. Johnson, Rapid Commun. Mass Spectrom. 2002, 16, 933 – 935. [17] F. Y. Wang, H. M. Chen, J. A. Parkinson, P. D. Murdoch, P. J. Sadler, Inorg. Chem. 2002, 41, 4509 –4523. [18] F. Y. Wang, J. J. Xu, A. Habtemariam, J. Bella, P. J. Sadler, J. Am. Chem. Soc. 2005, 127, 17734 –17743. [19] I. W. McNae, K. Fishburne, A. Habtemariam, T. M. Hunter, M. Melchart, F. Y. Wang, M. D. Walkinshaw, P. J. Sadler, Chem. Commun. 2004, 1786 – 1787. [20] F. Y. Wang, J. Bella, J. A. Parkinson, P. J. Sadler, J. Biol. Inorg. Chem. 2005, 10, 147 – 155. [21] S. L. Gonias, S. V. Pizzo, J. Biol. Chem. 1983, 258, 5764 –5769. [22] S. Sugio, A. Kashima, S. Mochizuki, M. Noda, K. Kobayashi, Protein Eng. 1999, 12, 439 –446. [23] F. Y. Wang, S. Weidt, J. J. Xu, C. L. Mackay, P. R. R. Langridge- Smith, P. J. Sadler, J. Am. Soc. Mass Spectrom. 2008, 19, 544 – 549. [24] T. J. Peters, All About Albumin: Biochemistry Genetics, and Medical Applications, Academic Press, New York, 1995, p. 54. [25] N. Ohta, D. Chen, S. Ito, T. Futo, T. Yotsuyanagi, K. Ikeda, Int. J. Pharm. 1995, 118, 85–93. [26] N. Ohta, T. Yotsuyanagi, D. Chen, R. Ono, S. Ito, K. Ikeda, Int. J. Pharm. 1992, 85, 39–44. [27] R. E. Aird, J. Cummings, A. A. Ritchie, M. Muir, R. E. Morris, H. Chen, P. J. Sadler, D. I. Jodrell, Br. J. Cancer 2002, 86, 1652 – 1657. [28] H. K. Liu, S. J. Berners-Price, F. Y. Wang, J. A. Parkinson, J. J. Xu, J. Bella, P. J. Sadler, Angew. Chem. 2006, 118, 8333 – 8336; Angew. Chem. Int. Ed. 2006, 45, 8153 – 8156. [29] O. Novakova, J. Kasparkova, V. Bursova, C. Hofr, M. Vojtiskova, H. M. Chen, P. J. Sadler, V. Brabec, Chem. Biol. 2005, 12, 121 – 129. [30] F. Wang, H. M. Chen, S. Parsons, L. D. H. Oswald, J. E. Davidson, P. J. Sadler, Chem. Eur. J. 2003, 9, 5810 – 5820. [31] A. Claiborne, T. C. Mallett, J. I. Yeh, J. Luba, D. Parsonage, Adv. Protein Chem. 2001, 54, 215 – 276. [32] L. Song, M. Z. Wang, J. J. Shi, Z. Q. Xue, M. X. Wang, S. J. Qian, Biochem. Biophys. Res. Commun. 2007, 362, 319 –324. [33] M. Tsujimura, N. Dohmae, M. Odaka, M. Chijimatsu, K. Takio, M. Yohda, M. Hoshino, S. Nagashima, I. Endo, J. Biol. Chem. 1997, 272, 29454 – 29459. [34] C. L. Wa, R. Cerny, D. S. Hage, Anal. Biochem. 2006, 349, 229 –241. [35] N. L. Allinger, J. Am. Chem. Soc. 1977, 99, 8127 –8134. |
| URI: | http://wrap.warwick.ac.uk/id/eprint/27658 |
Data sourced from Thomson Reuters' Web of Knowledge
Actions (login required)
![]() |
View Item |
Tools
Tools

