ISBN: 978-83-60043-10-3 - eurobic9

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Eurobic9, 2-6 September, 2008, Wrocław, Poland P103. Square-Planar Metallointercalators as Potential Anticancer Agents A. Krause-Heuer a , N. Orkey a , B. Singh a , J. Aldrich-Wright a a School of Biomedical and Health Sciences, University of Western Sydney, Narellen Road, 2560, Campbelltown, Australia e-mail: j.Aldrich-Wright@uws.edu.au The majority of clinically used platinum-based anticancer agents (eg cisplatin and carboplatin) effect their cytotoxic action by coordinating to specific atoms in the base-pairs of the DNA helix. However, unfavourable side effects such as nephrotoxicity and neurotoxicity are associated with these drugs. In an attempt to overcome the potential side effects with such drugs, a series of platinum(II) compounds have been innovatively designed which interact via a completely different mechanism – intercalation. These square-planar metallointercalators are composed of two bidentate ligands positioned around the platinum(II) metal centre: an intercalating moiety and a non-intercalating (ancillary) group. The planar intercalating segment is comprised of a minimum of three aromatic rings fused together and both chiral and achiral ancillary ligands have been utilised. The first compound in our series of platinum(II) metallointercalators was 1S, 2S diaminocyclohexane-1, 10-phenanthroline platinum(II). This compound displays a higher level of activity than cisplatin in all cell lines tested and is up to twenty times more soluble in water. These features suggest that this and similar compounds may demonstrate higher clinical effectiveness and lower toxicity than platinum-based compounds in clinical use. In vitro experiments have shown these complexes to be biologically active. The binding affinities of these compounds have also been investigated through UV-vis and CD spectroscopy. References: [1] Fenton, R. R.; Aldrich-Wright, J. R. In PCT Int. Appl.: Australia, 2002, pp 1-26. _____________________________________________________________________ 222
Eurobic9, 2-6 September, 2008, Wrocław, Poland P104. N-H⋅⋅⋅S and N-H⋅⋅⋅O Hydrogen Bonds as a Structure Forming Factor in Metal Silanethiolate Complexes with Additional N-donors A. Kropidłowska a , I. Turowska-Tyrk b , B. Becker a a Chemical Faculty, Gdańsk University of Technology, 11/12 Narutowicza Str., 80-952 Gdańsk, Poland e-mail: anna@urethan.chem.pg.gda.pl b Chemical Faculty, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland The N–H···S interactions are known for their important role in biological systems since the sulfur and nitrogen atoms of the side-chain of cysteine and histidine residues are two of the most common donors in biochemistry. They can bind to metal ions and form the active centers of numerous metalloenzymes and metalloproteins. Two Cys and two His residues bind e.g. to the zinc ion in the zinc finger proteins (transcription factor IIIA, enhancer binding protein in the human immunodeficiency virus type 1 (HIV-EPI) [1] and related nucleic acid binding proteins) [2]. Also a copper protein, Alcaligenes azurin, possesses SSN2 binding in the active site [3], although the role of N-H⋅⋅⋅S interaction in this system remains unclear. It was the reason which has stimulated scientists to search for the structural models of the S2N2 binding sites (see e.g. [4]). Since zinc is a spectroscopically silent metal, therefore cadmium and cobalt have been substituted in the native proteins to further aid in the study of the spectroscopic features of zinc centers [5]. For this reason, the study of Cd(II) coordination by protein-related ligands has attained renewed interest and attention. Our research efforts are also prompted towards the goal of generating complexes supported by a mixed nitrogen/sulfur coordination environment. Recently we reported on silanethiolate complexes containing aminopyridines [6] and diamines [7] as coligands with a sulfur atom serving as the N-H···S hydrogen bond acceptor. Now, we turned our attention to other N-donors capable of providing the NH donor group, reasoning that hydrogen bonding interactions might prove useful towards the stabilization and isolation of a nitrogen/sulfur ligated species.Using [Cd{SSi(OBu t )3}2]2 [8] as a substrate and cyclic aliphatic amines as coligands we synthesized new heteroleptic silanethiolate complexes with S2N2 binding sites. Thus, we have obtained four tetrahedral complexes i.e. [Cd{SSi(OBu t )3}2(NC4H9)2] 1 with pyrrolidine, [Cd{SSi(OBu t )3}2(NC5H11)2] with piperidine 2, [Cd{SSi(OBu t )3}2(NC4H9O)2] with morpholine 3 and [Cd{SSi(OBu t )3}2(N2C4H10)2] with piperazine 4. The X-ray structural analysis revealed basic forms of supramolecular packing mediated by inter- (see 3 in Fig. 1) and intramolecular hydrogen bonds of the N-H···S and N-H···O types. Fig.1. Acknowledgement: The research was supported by the grant of the Polish Ministry of Education and Science (grant No. 1 T09A 117 30). A. Kropidłowska thanks The Foundation for Polish Science for the fellowship. References: [1] A. J. van Wijnen, K. L. Wright, J. B. Lian, J. L. Stein, G. S. Stein, J . Biol. Chem., 264 (1989) 15034. [2] R. M. Evans and S. M. Hollenberg, Cell, 52 (1988) 1. [3] E. N. Baker, J. Mol. Biol., 203 (1988) 1071. [4] C. E. Forde, A. J. Lough, R. H. Morris, R. Ramachandran, Inorg. Chem., 35 (1996) 2747. [5] B. L. Vallee, in Zinc Proteins (T. G. Spiro, ed.) Wiley-lnterscience, New York, 1983. [6] A. Kropidłowska, I. Turowska-Tyrk, B. Becker, 18 ICPOC, Warsaw (2006) Book of Abstracts, 72. [7] A. Kropidłowska, I. Turowska-Tyrk, B. Becker, XVth Winter School on Coordination Chemistry, Karpacz (2006) Book of Abstracts, 61. [8] W. Wojnowski, B. Becker, L. Walz, K. Peters, E.-M. Peters, H.G. von Schnering, Polyhedron 11 (1992) 607. _____________________________________________________________________ 223
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ISBN: 978-83-60043-10-3 - eurobic9

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