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

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Eurobic9, 2-6 September, 2008, Wrocław, Poland P143. High Selective Epoxidation of Cyclohexene by Non-heme Ruthenium Complexes Incorporated into Mesoporous Silicate K. Okumura, K. Jitsukawa, T. Ozawa, Y. Funahashi, and H. Masuda Department of Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan e-mail: masuda.hideki@nitech.ac.jp Binding and activation of oxygen species in biological metallo-enzymes are regulated by the metal coordination structures and the non-covalent interaction groups surrounding them, such as hydrophobic and hydrogen bonding interaction ones. On the basis of the active site structures in biological systems, we have designed and synthesized some new artificial metallo-enzymes containing transition metal ions. The objective of our research project is to construct the artificial metallo-enzymes using these transition metal complexes and to develop environmentally-benign catalysts. We recently prepared the biomimetic materials consisted of metal complexes as an active site and nanoporous silicate as a reaction field, and the oxidation reaction with some substrates were carried out.[1][2][3] In this paper, we newly designed and synthesized new ruthenium(II) complex of 6,6’bis(benzoylamido)-2,2’-bipyridine (BABP) as an oxidation catalyst. This catalyst exhibited high efficient oxidations for cyclohexene when tert-butyl hydroperoxide was employed as an oxidant, but it does not show any selectivity. So we tried the immobilization of the ruthenium(II) complex into the nanoporous silicate FSM-16 that is often used as the substrate-specific reaction field in biological enzyme systems. Interestingly, it showed a higher epoxidation selectivity for cyclohexene. The material after the oxidation reaction was ESR active, indicating that the starting material for the catalytic reaction is Ru(III) species and the oxidation active species is Ru(V)=O. So we can propose that the oxidation reaction was carried out with cycle of Ru(III) and Ru(V)=O. Interestingly, this Ru(III) species was repeatedly used for epoxidation reaction. These findings indicate the nano-silicate FSM-16 can stabilize the active species and promote the effective capturing of the substrates. Acknowledgment: We gratefully acknowledge the support of this work from a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture, and in part by a grant from the NITECH 21st Century COE program. References: [1] T. Okumura, H. Takagi, Y. Funahashi, T. Ozawa, Y. Fukushima, K. Jitsukawa, and H. Masuda, Chem. Lett., 36, 122-123 (2007) [2] Y. Honda, H. Arii, T. Okumura, A. Wada, Y. Funahashi, T. Ozawa, K. Jitsukawa, and H. Masuda, Bull. Chem. Soc. Jpn. (Accounts, Invited), 80, 1288-1295 (2007). [3] T. Okumura, Y. Morishima, H. Shiozaki, T. Yagyu, Y. Funahashi, T. Ozawa, K. Jitsukawa, and H. Masuda, Bull. Chem. Soc. Jpn., 80, 507-517 (2007). _____________________________________________________________________ 262
Eurobic9, 2-6 September, 2008, Wrocław, Poland P144. New Complexes with N, N-dimethylbiguanide Displaying Low Cytotoxicity as Potential Large Spectrum Antimicrobial Agents R. Olar a , M. Badea a , D. Marinescu a , G. Vasile b , V. Lazar c , C. Chifiriuc Balotescu c a Faculty of Chemistry University of Bucharest Panduri, 050663, Bucharest, Romania, b Agrochemistry, University of Agronomical Sciences and Veterinary, Marasti, , Bucharest, Romania c Faculty of Biology, University of Bucharest, Aleea portocalelor, 060<strong>10</strong>1, Bucharest, Romania e-mail: rodica_m_olar@yahoo.com Selective and effective antimicrobial activities against Gram-positive and Gram-negative bacteria were found for a series of new complexes with N, N-dimethylbiguanide (DMBG). The complexes with general formula M(DMBG)2(ClO4)2 ((1) M:Mn; (2) M:Ni, (3) M:Cu and (4) M:Zn) have been synthesized. The methods used in order to characterize the bonding and the stereochemistry of the complexes were IR, EPR, 1 H NMR and electronic spectroscopy. Recrystallization from DMF of (2) afforded crystals of type [Ni(DMBG)2](ClO4)2·2CHON(CH3)2 (2a) in the monoclinic P2(1)/c space group. The antimicrobial activities of complexes was investigated by qualitative (disk diffusion) and quantitative (liquid medium serial microdillution) methods on planktonic and biofilm embedded bacterial and fungal strains. Metal-free N, N-dimethylbiguanide derivatives and the complexes exhibited specific antiinfective properties as demonstrated by the low MIC values, the large antimicrobial spectrum and by the inhibition of the microbial ability to colonize the inert surfaces. At the same time, excepting the complex (2), the other metal complexes exhibited low citotoxicity levels on HeLa cells, this representing a great advantage for the in vivo use of the tested complexes as antimicrobial agents. Acknowledgement: This work was partially supported by the grants PNII nr. 61-48/2007 and VIASAN 142/2006 of the Romanian Ministry of Education and Research. _____________________________________________________________________ 263
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ISBN: 978-83-60043-10-3 - eurobic9

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