Book of Abstracts - Ruhr-Universität Bochum
Book of Abstracts - Ruhr-Universität Bochum Book of Abstracts - Ruhr-Universität Bochum
P-37 ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum Cytotoxicity Studies on Rhenium(I) Tricarbonyl Complexes Teck-Tian Wong, Li-Peng Wong, Peng-Foo Peter Lee and Yaw-Kai Yan* Nanyang Technological University, National Institute of Education, Natural Sciences & Science Education Department, 1 Nanyang Walk, Singapore 637616. E-mail: yawkai.yan@nie.edu.sg Since the late 1980’s, there has been a steady growth of interest in ruthenium anti-cancer drugs as reflected in the accelerating growth of publications in this area. 1 In particular, a series of water soluble and stable ruthenium(II) arene ethylenediamine complexes (1) was shown to exhibit promising anticancer activity in vitro and in vivo. 2 Anti-cancer activity has also been observed in rhenium(I) tricarbonyl complexes. 3 Since both rhenium(I) and ruthenium(II) are d 6 configuration metal ions, it would be interesting to investigate the anti-cancer activity of rhenium(I) tricarbonyl complexes with N,N- and P,P- chelating agents. The three CO ligands of the Re(I) complexes correspond to the arene ligand of the Ru(II) complexes in that both donate six electrons. The chelating N,N- and P,P- ligands of the Re(I) complexes correspond to the ethylenediamine ligand of the Ru(II) complexes and both types of complexes have a single ligand exchange site occupied by a monoanionic ligand. In this study, we are concerned with the synthesis and bio-physicochemical characterization of a series of mononuclear rhenium(I) tricarbonyl complexes [Re(X)(CO)3L2] (2) [where X = Br, Cl, Cl2HCCO2; L2 = ethylenediammine (en), N,N,N ′ ,N ′ -tetramethylethylenediamine (tmen), 2,2 ′ -bipyridine (bpy), N,N ′ -dimethylethylenediamine (dmen), 2,2 ′ -bipyridine-4,4 ′ -dicarboxylic acid (H2bpdc), 1,3-bis(diphenylphosphino)propane (dppp) and 1,1′-bis(diphenylphosphino)ferrocene (dppf)]. All the complexes were characterized by IR and 1 H NMR spectroscopy and elemental analysis. The rhenium complexes and their respective ligands were screened using the human leukaemia (MOLT-4) cell line via the MTT assay. The results will be presented in the poster. References Cl Ru N N R + 95 OC OC Re 1 2 1. A. Levina, A. Mitra, P. L. Lay, Metallomics 2009, 1, 458-470. 2. Y. K. Yan, M. Melchart, A. Habtemariam, P. J. Sadler, Chem. Commun. 2005, 4764-4776. 3. (a) J. Zhang, J. J. Vittal, W. Henderson, J. Wheaton, I. H. Hall, T. S. A. Hor, Y. K. Yan, J. Organomet. Chem. 2002, 650, 123-132. (b) Y. K. Yan, S. E. Cho, K. A. Shaffer, J. E. Rowell, B. J. Barnes, I. H. Hall, Pharmazie 2000, 55, 307-313. (c) W. Wang, Y. K. Yan, T. S. A. Hor, J. J. Vittal, J. R. Wheaton, I. H. Hall, Polyhedron 2002, 21, 1991-1999. X L CO L
P-38 ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum Bioorthogonal Coupling Strategies in the Synthesis of CORM-peptide Conjugates a Hendrik Pfeiffer, a Johanna Niesel, b and Ulrich Schatzschneider* a Ruhr-Universität Bochum, Department of Chemistry and Biochemistry, Universitätsstrasse 150, 44801 Bochum, Germany, hendrik.pfeiffer@rub.de In the human body carbon monoxide possesses versatile properties as a signalling mediator and participates in important biological processes. Beside being a potent vasodilator, CO can exert antiinflammatory, anti-apoptotic, and anti-proliferative effects. 1,2 Since it is a toxic gas and difficult to handle, there is considerable interest in the development of CO releasing molecules (CORMs) as "solid storage forms" for carbon monoxide. Therefore, transition metal carbonyl complexes are highly interesting target structures. 3 Compared to thermally induced liberation of CO, photoactivated CO release will allow for a precise spatial and temporal control of its biological action. 4 We have recently synthesized several tungsten, molybdenum, and manganese complexes with bidentate as well as tridentate nitrogen donor ligands as promising new photoCORMs, which are inert in the dark in aqueous solution, but release CO upon irradiation. 5 Carrier peptides are important vehicles to achieve accumulation of bioactive cargos in specific biological target sites. Thus, we have explored the functionalization of the parent photoCORMs with model peptides using bioorthogonal coupling strategies, such as oxime ligation, Sonogashira crosscoupling, or the alkyne-azide 1,3-dipolar cycloaddition (click reaction). 6 References 1. S. W. Ryter, J. Alam, A. M. K. Choi, Physiol. Rev. 2006, 86, 583-650. 2. T. R. Johnson, B. E. Mann, J. E. Clark, R. Foresti, C. J. Green, R. Motterlini, Angew. Chem. Int. Ed. 2003, 42, 3722-3729. 3. J. Boczkowski, J. J. Poderoso, R. Motterlini, Trends Biochem. Sci 2006, 31, 614-621. 4. U. Schatzschneider, Eur. J. Inorg. Chem. 2010, 1451-1467. 5. J. Niesel, A. Pinto, H. W. Peindy N'Dongo, K. Merz, I. Ott, R. Gust, U. Schatzschneider, Chem. Commun. 2008, 1798-1800. 6. H. Pfeiffer, A. Rojas, J. Niesel, U. Schatzschneider, Dalton Trans. 2009, 4292-4298. 96
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P-38<br />
ISBOMC `10 5.7 – 9.7. 2010 <strong>Ruhr</strong>-<strong>Universität</strong> <strong>Bochum</strong><br />
Bioorthogonal Coupling Strategies in the Synthesis <strong>of</strong> CORM-peptide Conjugates<br />
a<br />
Hendrik Pfeiffer, a Johanna Niesel, b and Ulrich Schatzschneider* a<br />
<strong>Ruhr</strong>-<strong>Universität</strong> <strong>Bochum</strong>, Department <strong>of</strong> Chemistry and Biochemistry,<br />
<strong>Universität</strong>sstrasse 150, 44801 <strong>Bochum</strong>, Germany, hendrik.pfeiffer@rub.de<br />
In the human body carbon monoxide possesses versatile properties as a signalling mediator and<br />
participates in important biological processes. Beside being a potent vasodilator, CO can exert antiinflammatory,<br />
anti-apoptotic, and anti-proliferative effects. 1,2 Since it is a toxic gas and difficult to<br />
handle, there is considerable interest in the development <strong>of</strong> CO releasing molecules (CORMs) as<br />
"solid storage forms" for carbon monoxide. Therefore, transition metal carbonyl complexes are highly<br />
interesting target structures. 3 Compared to thermally induced liberation <strong>of</strong> CO, photoactivated CO<br />
release will allow for a precise spatial and temporal control <strong>of</strong> its biological action. 4 We have recently<br />
synthesized several tungsten, molybdenum, and manganese complexes with bidentate as well as<br />
tridentate nitrogen donor ligands as promising new photoCORMs, which are inert in the dark in<br />
aqueous solution, but release CO upon irradiation. 5<br />
Carrier peptides are important vehicles to achieve accumulation <strong>of</strong> bioactive cargos in specific<br />
biological target sites. Thus, we have explored the functionalization <strong>of</strong> the parent photoCORMs with<br />
model peptides using bioorthogonal coupling strategies, such as oxime ligation, Sonogashira crosscoupling,<br />
or the alkyne-azide 1,3-dipolar cycloaddition (click reaction). 6<br />
References<br />
1. S. W. Ryter, J. Alam, A. M. K. Choi, Physiol. Rev. 2006, 86, 583-650.<br />
2. T. R. Johnson, B. E. Mann, J. E. Clark, R. Foresti, C. J. Green, R. Motterlini, Angew. Chem. Int. Ed.<br />
2003, 42, 3722-3729.<br />
3. J. Boczkowski, J. J. Poderoso, R. Motterlini, Trends Biochem. Sci 2006, 31, 614-621.<br />
4. U. Schatzschneider, Eur. J. Inorg. Chem. 2010, 1451-1467.<br />
5. J. Niesel, A. Pinto, H. W. Peindy N'Dongo, K. Merz, I. Ott, R. Gust, U. Schatzschneider, Chem.<br />
Commun. 2008, 1798-1800.<br />
6. H. Pfeiffer, A. Rojas, J. Niesel, U. Schatzschneider, Dalton Trans. 2009, 4292-4298.<br />
96
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