Sanchez-Cano, Carlos, Huxley, Martin, 1980-, Ducani, Cosimo, Hamad, Amal E., Browning, Michael J., Navarro-Ranninger, Carmen, Quiroga, Adoracion G., Rodger, Alison and Hannon, M. J. (Michael J.). (2010) Conjugation of testosterone modifies the interaction of mono-functional cationic platinum(II) complexes with DNA, causing significant alterations to the DNA helix. Dalton Transactions, Vol.39 (No.47). pp. 11365-11374. ISSN 1477-9226

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Abstract

Previously a range of androgen conjugates with non-conventional platinum(II) complexes have been synthesised with the aim of enhancing cellular delivery, and which have shown increased cytotoxic activity compared with non-steroidal compounds (M. J. Hannon et al., Dalton Trans., 2010, DOI: 10.1039/c0dt00838a). To further study this, the complexes have been assessed for their ability to bind to and alter the structure of DNA. All platinum(II) complexes studied herein bind to model nucleo-bases and DNA, but to our surprise, testosterone-based complexes caused the DNA helix to undergo significant unwinding and bending, whereas non-steroidal control complexes caused minimal structural alterations. These effects are similar to those cisplatin induces on DNA structure despite the fact that these compounds produce a monofunctional lesion. This ability attributed to interactions between the DNA helix and bulky steroidal skeleton of testosterone, coupled with the enhanced cellular delivery induced by the steroid make the steroid approach an exciting way to explore non-conventional platinum drug delivery.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry Q Science > QP Physiology
Divisions:	Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH):	Bioconjugates, Testosterone, Metal complexes, Platinum, Drug delivery systems, DNA
Journal or Publication Title:	Dalton Transactions
Publisher:	Royal Society of Chemistry
ISSN:	1477-9226
Date:	21 December 2010
Volume:	Vol.39
Number:	No.47
Number of Pages:	10
Page Range:	pp. 11365-11374
Identification Number:	10.1039/c0dt00839g
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access
Funder:	Biotechnology and Biological Sciences Research Council (Great Britain) (BBSRC), University of Birmingham, University of Warwick, European Union, Spain. Comisión Interministerial de Ciencia y Tecnología (CICYT)
Grant number:	SAF 2006-03296 (CICYT), SAF 2009-0431 (CICYT)
References:	1 B. Rosenberg, L. Van Camp, E. B. Grimley and A. J. Thompson, J. Biochem., 1967, 242, 1347. 2 (a) B. Lippert, Cisplatin, Chemistry and Biochemistry of A Leading Anticancer Drug,Wiley-VCH,Weinheim, 1999; (b)M. J.Hannon, Pure and Applied Chemistry, 2007, 79, 2243. 3 E. R. Jamieson and S. J. Lippard, Chem. Rev., 1999, 99, 2467. 4 G. Natile and M. Coluccia, Coord. Chem. Rev., 2001, 216–217, 383. 5 M. Ohndorf, M. A. Rould, Q. He, C. O. Pabo and S. J. Lippard, Nature, 1999, 399, 708. 6 A. Eastman, Biochemistry, 1986, 25, 3912. 7 S. F. Bellon, J. H. Colleman and S. J. Lippard, Biochemistry, 1991, 30, 8026. 8 P.M. Takahara, A. C. Rosenzweig, C. A. Frederick and S. J. Lippard., Nature, 1995, 377, 649. 9 J.-S. Hoffmann, D. Locker, G. Villani andM. Leng, J. Mol. Biol., 1997, 270, 539. 10 L. Li, X. Liu, A. B. Glassman, M. J. Keating, M. Stros, W. Plunkett and L. Y. Yang, Cancer Res., 1997, 57, 1487. 11 R. Dalbies,D. Payet and M. Leng, Proc. Natl. Acad. Sci. U. S. A., 1994, 91, 8147. 12 U. Bierbach and N. Farrell, Inorg. Chem., 1997, 36, 3657. 13 Y. Zuo, B. Van Houten and N. Farrell, Biochemistry, 1993, 32, 9632. 14 M. J. Cleare and J. D. Hoeschele, Bioinorg. Chem., 1973, 2, 187. 15 (a) N. Farrell, T. T. B. Ha, J.-P. Souchard, F. L. Wimmer, S. Cros and N. P. Johnson, J. Med. Chem., 1989, 32, 2240; (b) E. I. Montero, S. Diaz, A.M. Gonzalez-Vadillo, J.M. Perez, C. Alonso and C. Navarro- Ranninger, J. Med. Chem., 1999, 42, 4264; (c) M. Coluccia and G. Natile, Anti-Cancer Agents Med. Chem., 2007, 7, 111; (d) N. Farrell, Met. Ions Biol. Syst., 2004, 41, 252; (e) L. S. Hollis, A. R. Amundsen and E. W. Stern, J. Med. Chem., 1989, 32, 128; (f) L. S. Hollis, W. I. Sundquist, J. N. Burstyn, W. J. Heiger-Bernays, S. F. Bellon, K. J. Ahmed, A. R. Amundsen, E. W. Stern and S. J. Lippard, Cancer Res., 1991, 51, 1866; (g) K. S. Lovejoy, R. C. Todd, S. Zhang, M. S. McCormick, J. A. D’Aquino, J. T. Reardon, A. Sancar, K. M. Giacomini and S. J. Lippard, Proc. Natl. Acad. Sci. U. S. A., 2008, 105, 8902. 16 D. Jodrell, T. Evans,W. Steward,D. Cameron, J. Prendiville,C.Aschele, C. Noberasco, M. Lind, J. Carmichael and N. Dobbs, Eur. J. Cancer, 2004, 40, 1872. 17 M. Huxley, C. Sanchez-Cano, M. J. Browning, C. Navarro-Ranninger, A. G. Quiroga, A. Rodger and M. J. Hannon, Dalton Trans., 2010, 39, DOI: 10.1039/c0dt00838a. 18 (a) R. Devraj, J. F. Barrett, J. A. Fernandez, J. A. Katzenellenbogen and M. Cushman, J. Med. Chem., 1996, 39, 3367; (b) S. Top, A. Vessi`eres, C. Cabestaing, I. Laios,G. Leclerq, C. Provot andG. Jaouen, J. Organomet. Chem., 2001, 637–639, 500; (c) S. Top, E. B. Kaloun, A. Vessieres, G. Leclercq, I. Laios, M. Ourevitch, C. Deuschel, M. J. McGlinchey and G. Jaouen, ChemBioChem, 2003, 4, 754; (d) K. R. Barnes, A. Kutikov and S. J. Lippard, Chem. Biol., 2004, 11, 557; (e) C. Cassino, E. Gabano, M. Ravera, G. Cravotto, G. Palmisano, A. Vessi`eres, G. Jaouen, S. Mundwiler, R. Alberto and D. Osella, Inorg. Chim. Acta, 2004, 357, 2157; (f) E. Gabano, C. cassino, S. Bonetti, C. Prandi,D. Colangelo,A. L. Ghiglia andD.Osella, Org. Biomol. Chem., 2005, 3, 3531; (g) V. Gagnon, M. E. St-Germain, C. Descˆoteaux, J. Provencher-Mandeville, S. Parent, S. K. Mandal, E. Asselin and G. B´erub´e, Bioorg. Med. Chem. Lett., 2004, 14, 5919; (h) V. Perron, D. Rabouin, E. Asselin, S. Parent, R. C. C. Gaudreault and G. B´erub´e, Bioorg. Chem., 2005, 33, 1; (i)M. J. Hannon, P. S. Green, D. M. Fisher, P. J. Derrick, J. L. Beck, S. J. Watt, M. M. Sheil, P. R. Barker, N. W. Alcock, R. J. Price, K. J. Sanders, R. Pither, J. Davis and A. Rodger, Chem.–Eur. J., 2006, 12, 8000. 19 For an example ofDNA binding studies of non-covalentDNA binding steroidal complexes see: C. Sanchez-Cano and M. J. Hannon, Dalton Trans., 2009, 10765. 20 E. L. M. Lempers, M. J. Bloemink, H. Brouwer, Y. Kidani and J. Reedijk, J. Inorg. Biochem., 1990, 40, 23. 21 (a) Y. Ma, C. S. Day and U. Bierbach, J. Inorg. Biochem., 2005, 99, 2013; (b) T. Peleg-Shulman, J. Katzhendler and D. Gibson, J. Inorg. Biochem., 2000, 81, 313. 22 V. X. Jin, S. I. Tan and J. D. Ranford, Inorg. Chim. Acta, 2005, 358, 677.
URI:	http://wrap.warwick.ac.uk/id/eprint/4755

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