Book of Abstracts - Ruhr-Universität Bochum

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OP-15 ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum Arjunolic acid: The First Renewable-Nano Triterpenoid in Bioorganometallics Braja G. Bag, *a Partha P. Dey, a Rakhi Majumdar, a Shaishab K. Dinda, a and Shib S. Das a a Vidyasagar University, Department of Chemistry and Chemical Technolgy, Midnapore 721 102, India. E-mail: bgopalbag@yahoo.co.in Utilization of plant metabolites as renewables in various facets of bioorganic, bioorganometallic and organic chemistry research has become significant in recent years because such investigations aim at the development of sustainable chemical feedstocks. 1 Ferrocene moiety has been utilized in the design of peptide analogues, redox-responsive gelators, enhanced antimalarial drugs, etc. 2 However, inspite of the abundance of a large variety of triterpenoids, having nano-metric dimensions with varied lengths of rigid and flexible parts, 3 according to our knowledge, no ferroceno-triterpenoid has been reorted so far. Availability of arjunolic acid 1, extractable from the heavy wood of Terminalia Arjuna became the first choice for such investigations. 4 Figure 1: (a) A redox-responsive organogel from ferrocenylidene arjunolic acid 2, (b) SEM image reveals self-assembled fibrillar network having fibers of nano-meter diameters, (c) TEM image of CdS nano-particles templated by self-assembled nano-fibers from arjunolic acid derivatives. The ferrocenylidene arjunolic acid 2, synthesized in one-step from arjunolic acid 1 and formylferrocene in high yield, self-assembled in various organic media to form soft solid-like materials (Figure 1a, Table 1). Scanning electron micrographs of the soft-solids showed fibrillar net-work structures having fibers of nano-metric dimensions (Figure 1b). Solvent State Conc. (g/100 mL) Toluene Gel 10 o-Xylene Gel 9 m-Xylene Gel 10 p-Xylene Gel 10 Table 1: Gelation Test Results of 2 Detailed investigations on the self-assembly of arjunolic acid or its derivatives revealed that most of these derivatives selfassemble in aqueous or organic liquids leading to the formation of fibers of nano-metric diameters. 5,6 When H2S gas was diffused through a gel of an arjunolic acid derivative in ethanol saturated with Cd(OAc)2, then porous CdS nanoparticles templated by the self-assembled nano-fibers were formed (Figure 1c). Recent results from our laboratory will be presented describing various approaches towards bioorganometallic chemistry for the utilization triterpenoids. Acknowledgements: Financial assistance from AvH foundation Germany and DRDO India are gratefully acknowledged. References 1. B.G. Bag, S.K. Dinda, Pure Appl. Chem. 2007, 79, 2031. 2. (a) D.R. van Staveren , N. Metzler-Nolte, Chem. Rev. 2004, 104, 5931; (b) F. Dubar, G. Anquetin, B. Pradines, D. Dive, J. Khalife, C. Biot, J. Med. Chem. 2009, 52, 7954. 3. B.G. Bag, C. Garai, R. Majumdar, unpublished results. 4. B.G. Bag, P.P. Dey, S.K. Dinda, W.S. Sheldrick, I.M. Oppel, Beil. J. Org. Chem. 2008, 4, 24. 5. B.G. Bag, S.K. Dinda, P.P. Dey, A.V. Mallia, R.G. Weiss, Langmuir 2009, 25, 8663. 6. B.G. Bag, G.C. Maity, S.K. Dinda, Org. Lett. 2006, 8, 5457. 31
OP-16 Ru N Cl Cl N Ru Cl Cl ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum Anticancer Activity of Multinuclear Ruthenium-Arene Complexes Coordinated to Dendritic Poly(propyleneimine) Scaffolds R R O N R Cl Ru Cl N N Ru Cl O Cl N R N R N Cl Cl N Ru N Cl Cl R Gregory S. Smith *a and P. Govender a a University of Cape Town, Faculty of Science, Department of Chemistry, 7701, Cape Town, South Africa. E-mail: Gregory.Smith@uct.ac.za Dendrimers have found potential as molecular tools in biological applications, especially as nanocarriers, diagnostic agents and as chemotherapeutics. 1-4 An advantage of using dendrimers is their multivalency, which leads to increased interaction between a dendrimer-drug conjugate and a target bearing multiple receptors, further improving the selectivity to cancer cells. Large macromolecules, like dendrimers, can also specifically target tumours by exploiting the ‘enhanced permeability and retention’ (EPR) effect, in which macromolecules can accumulate at the tumour site due to an increase in blood vessel permeability within diseased tissues compared to normal tissues. 5 In this presentation, we report a series of multinuclear ruthenium-arene complexes based on first- and second-generation poly(propyleneimine) dendritic scaffolds (Fig. 1). Their cytotoxicity against the A2780 human ovarian cancer cell line will also be discussed. O N Ru N O N Cl Cl Ru N Cl Cl N Ru N 32 R R Cl Cl N Ru N R R N N Ru Cl Cl = N R R N Ru N N Cl Cl R N Ru N Cl Cl Fig. 1: Ruthenium-arene metallodendrimers based on a poly(propyleneimine) scaffold. References 1. (a) U. Boas, J. B. Christensen, P. M. H. Heegaard: Dendrimers in Medicine and Biotechnology: New Molecular Tools, RSC Publishing (2006). (b) C. C. Lee, J. A. MacKay, J. M. J. Fréchet, F. C. Szoka, Nature Biotech. 2005, 23, 1517-1526. 2. F. Aulenta, W. Hayes, S. Rannard, Eur. Polym. J. 2003, 39, 1741-1771 and references therein. 3. J. B. Wolinsky, M. W. Grinstaff, Adv. Drug Deliv. Rev. 2008, 60, 1037-1055 and references therein. 4. (a) A. Agarwal, S. Saraf, A. Asthana, U. Gupta, V. Gajbhiye, N. K. Jain, Int. J. Pharm. 2008, 350, 3-13. (b) E. R. Gillies, J. M. J. Fréchet, Drug Discov. Today 2005, 10, 35- 43. 5. D.F. Baban, L.W. Seymour, Adv. Drug Delivery Rev. 1998, 34, 109-119. 4+ O O H
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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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