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P-11 ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum Synthesis, Characterizatiotion and Biological Evaluation of New Organometallic Rhenium(I) Complex with Ferulic Acid Dmytro Bobukhov, a Maksym Izumsky, a and Alexander Shtemenko *a a Ukrainian State Chemical Technological University, Department of Inorganic Chemistry, Gagarin Avenue 8, 49005, Dnipropetrovs’k, Ukraine. E-mail: dbobukhov@googlemail.com The aqueous chemistry of the organometallic cation [Re(CO)3(H2O)3] + has received much attention over the past decade, due to its relevance to the design of 186/188 Re radiopharmaceuticals as well as its ability to act as a surrogate for the chemistry of [ 99m Tc(CO)3] + . In many cases, these investigations have focused on reactions between biomolecules and [Re(CO)3(H2O)3] + . The attractiveness of this low-valent precursor results from its particularly high thermodynamic stability, that is, high substitution stability of CO ligands and substitution lability of water molecules, which can be easily replaced by a variety of mono, bis, and tridentate ligands of different size, shape, and donor atom sets. 1 Here we report the synthesis, characterization and biological evaluation of new rhenium(I) complex with ferulic acid (3-(4-hydroxy-3-methoxyphenyl)-2-propenoic acid, C10H10O4). Ferulic acid is a phenolic acid of low toxicity, it can be absorbed and easily metabolized in the human body. Ferulic acid has been reported to have many physiological functions, including antioxidant, antiinflammatory, antithrombosis, and anticancer activities. 2 Because of these properties and its low toxicity, we decided to study interaction between trans-ferulic acid and [Re(CO)3(H2O)3] + cation, and possibility of using phenolic acid – rhenium(I) complexes in biomedicine. The corresponding complex was synthesized in a stepwise manner from [Re(CO)3(H2O)3]Br and trans-ferulic acid in methanol. The compound has been characterized by 1 H NMR, ESI-MS and IR spectroscopy. Crystal structure and biological activity of the corresponding complex will be discussed. References 1. S. Alves, A. Paulo, J. D. G. Gorreia, L. Gano, C. J. Smith, T. J. Hoffman, I. Santos, Bioconjugate Chem. 2005, 16, 438-449. 2. S. Ou, K.-C. Kwok, J. Sci. Food Agric. 2004, 84, 1261-1269. 69
P-12 ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum Synthesis of Ferrocene Peptide Conjugates and their Application as Inhibitors of Peptide Association Samaneh Beheshti, a and Heinz-Bernhard Kraatz a a The University of Western Ontario, Faculty of Science, Department of Chemistry, 1151 Richmond St, N6A 5B7, London, Ontario, Canada. Email: sbehesh@uwo.ca The amyloid beta peptide (Aβ) with 40-42 amino acids is the major constituent of plaques found in the brain of people affected with Alzheimer’s disease. 1 There is a hypothesis that conformational switching from α-helical to β-sheet ultimately leads to amyloid fibril formation . On this basis, finding compounds that are able to destabilize the β-sheet structure and to interfere with the assembly of peptide strands is a useful strategy to prevent peptide aggregation and fibril formation. Synthetic peptides have been reported as β-sheet breakers that preclude amyloid formation. 2 For example, a novel pentapeptide inhibitor that has a proline in place of valine and an aspartic acid in place of alanine in the Aβ17-21 (Leu-Val-Phe-Phe-Ala) fragment has been reported with the ability to inhibit the formation of amyloid fibrils. 3 In this work, a series of Fc-peptide conjugates is prepared of the type FcCO-Val-Phe-Phe-OR (1:R = Me, 2:R = H), Fc[CO-Val-Phe-Phe-OR]2 (3:R = Me, 4:R = H), Fc[CO- Val-Phe-OR]2 (5:R = Me, 6:R = H) and Fc[CO-Leu-Val-OR]2 (7:R = Me, 8:R = H) . Conformational properties of these ferrocene peptide conjugates and their interaction with several sequences of Aβ have been studied in solution by circular dichroism and scanning electron microscopy. In addition, the interaction of Aβ attached on the gold surface with these ferrocene peptide conjugates has been studied by using electrochemical methods. References 1. L. O. Tjernberg, J. Naslund, F. Lindqvist, J. Johansson, A.R. Karlstrom, J.Thyberg, L. Terenius,C. Nordstedt, J. Biol. Chem. 1996, 271, 8545-8548. 2. C. Soto, E.M. Sigurdsson, L. Morelli, R.A. Kumar, E.M. Castano, B. Frangione, Nat. Med. 1998, 4, 822-826. 3. C. Adessi, M.J. Frossard, C. Boissard, S. Fraga, S. Bieler, T. Ruckle,F. Vilbois, S.M. Robinson, M. Mutters, W.A. Banks, C. Soto, J. Biol. Chem. 2003, 278, 13905-13911. 70
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ISBOMC ‘10 5th International Symp
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Foreword ISBOMC `10 5.7 - 9.7. 2010
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Sergey Abramkin Universität Wien,
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Tensim Dallagi ENSCP, France t.dall
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Prof. Dr. Toshikazu Hirao Osaka Uni
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Obiora Augustine Orakwue Hyqid Nige
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Book of Abstracts - Ruhr-Universität Bochum

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