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

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Eurobic9, 2-6 September, 2008, Wrocław, Poland P97. Peptides Conjugated with Quinoxalines and Their Affinity to Metal Ions Analysed by High Resolution Mass Spectrometry A. Kluczyk, B. Predko, A. Staszewska, P. Stefanowicz, M. Jeżowska-Bojczuk, Z. Szewczuk Faculty of Chemistry, University of Wroclaw, F. Joliot-Curie 14, 50-3<strong>83</strong> Wroclaw, Poland e-mail: kluczyk@wchuwr.pl The search for new bioactive peptides directed our attention to new methods for introducing heterocyclic motifs into peptide side chains [1]. Considering the biological activity and complexing abilities of quinoxalines we developed a direct solid-phase synthesis of quinoxaline-peptide conjugates, expecting these new compounds to express novel biological properties [2]. We investigated two solid phase protocols of synthesis of quinoxaline-containing peptides. The first method uses the commercially available 4-amino-3-nitrobenzoic acid, which could be attached to the ε-amino group of lysine or the N-terminal α-amino group of peptide. For the second procedure we developed a special phenylalanine derivative, Fmoc-Phe(4’-NH2-3’-NO2)-OH, which can be used as a building block for standard Fmoc protocol for peptide synthesis [2]. In both these methods the quinoxaline formation involves reduction of the aromatic nitro group and the subsequent condensation of the o-phenylenediamine intermediate with α-dicarbonyl reagents. N N N N N N _____________________________________________________________________ 216 A N N O Aaa O NH NH Peptides containing quinoxaline motifs: A - as a modification of amino groups, B - in the form of a novel amino acid residue. Aaa represents amino acid residue or peptide fragment. Using these procedures we obtained a series of peptides conjugated with quinoxalines containing various substituents. We concentrated our attention on compounds with two 2-pyridil moieties attached to the quinoxaline skeletons. Such heterocyclic systems are known for their affinity to metal ions [3], whereas bipyridine-peptide conjugates complexed with ruthenium ion and additional quinoxaline derivative were investigated as metallointercalators [4]. We investigated the binding of copper (II) ions to both types of quinoxaline-peptide conjugates using high resolution electrospray mass spectrometry. The method is ideal for initial screening of potential high affinity ligands because of minimal sample consumption and the insight into the structure of the complex through the fragmentation analysis and the experiments involving proton-deuter exchange. Acknowledgements: Supported in part by Grant No. N N204 1616 33 from the MSHE (Poland). References: [1] A. Kluczyk, A. Staszewska, P. Stefanowicz et al., J. Peptide Sci., 12, 111 (2006). [2] A. Staszewska, P. Stefanowicz, Z. Szewczuk, Tetrahedron Lett., 46, 5525 (2005). [3] A.A. Abdel-Shafi, M.M.H. Khalil, H.H. Abdalla, R.M. Ramadan, Transition Metal Chemistry, 27, 69 (2002). [4] K.D. Copeland, A.M.K. Lueras, E.D.A. Stemp, J.K. Barton, Biochemistry, 41, 12785 (2002). O Aaa N Aaa B N N NH O N Aaa
Eurobic9, 2-6 September, 2008, Wrocław, Poland P98. Dinuclear Metal Complexes of a bis-intercalater Ligand as a Strong DNA-binder M. Kodera, K. Hamada, T. Nakamura, Y. Hitomi, T. Funabiki, K. Kano Molecular Chemistry and Biochemistry, Doshisha University, Tatara Miyakotani, 6<strong>10</strong>-0321, Kyotanabe, Japan e-mail: mkodera@mail.doshisha.ac.jp In order to explore a strong DNA-binder we have synthesized dinuclear metal complexes with a new bis-intercalater ligand (H2L1) that has two phenanthrene groups. The ligand reacts with Zn(OAc)2 and Cu(OAc)2 in MeOH to form dinuclear complexes [Zn2(AcO)2(L1)] and [Cu2(AcO)2(L1)], respectively. The dicopper complex is stable in an aqueous solution at pH 7.1, but the dizinc complex decomposes to mononuclear complex under aqueous conditions. The crystal structure of the dicopper complex was determined by X-ray analysis. DNA-binding studies are carried out with both the ligand and the dicopper complex. The dicopper complex binds DNA much more strongly than the ligand. DNA-binding affinity of the dicopper complex may be enhanced by synergistic intercalation of the phenanthrene groups with binding of phosphate group of DNA to the dicopper center. _____________________________________________________________________ 217
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ISBN: 978-83-60043-10-3 - eurobic9

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