Senior Lecturer in Medicinal Chemistry
5 West - 3.6
Tel: +44 (0) 1225 385709
Dr Lorenzo Caggiano
The central focus of the group is to achieve the efficient synthesis of biologically active small molecules, using known and new synthetic methodologies.
Basic synthetic steps are often used to make elegant molecules; we wish to establish a programme of research using elegant chemistry to synthesise basic molecules, which have been shown to display potent biological activities.
Structural complexity does not necessarily correlate with biological activity...
Efficient Synthesis of Biologically Active Molecules
We are currently investigating the efficient synthesis of simplified analogues of various biologically active compounds as potential therapeutics and have several projects at various stages. Our work in the design and synthesis of novel analogues of natural products obtained from daffodils also features in the University of Bath Research Brochure.
Capture and Functionalisation of CO2
During the course of our investigations, we discovered a new transformation in which CO2 was sequestered from the atmosphere and functionalised. We are investigating the potential of using this transformation to industrial applications.
Novel Prenylation Reactions
We have discovered an efficient procedure for the prenylation of various substituted arenes.
Design and Synthesis of Fluorescent Sensors for Cd2+ and Zn2+
We are currently investigating the potential of some of our compounds as "turn on" fluorescent sensors for Cd2+ and Zn2+, which will find various applications.
Use of Metal Chelates as Molecular Scaffolds
Our interests also include the design and synthesis of metal chelators and their application as molecular scaffolds, generating 3D biological systems. We report the synthesis of a maltol-derived hydrazide and its potential to induce rapid multicellular aggregation of modified cells selectively in the presence of Fe3+ ions.
Ali Khan, M., Wood, P. J., Lamb-Guhren, N. M., Caggiano, L., Kociok-Köhn, G., Tosh, D. and Lewis, S. E., 2014. The enone motif of (+)-grandifloracin is not essential for 'anti-austerity' antiproliferative activity. Bioorganic & Medicinal Chemistry Letters, 24 (13), pp. 2815-2819.
Ciupa, A., De Bank, P. A. and Caggiano, L., 2013. Multicellular aggregation of maltol-modified cells triggered by Fe3+ ions. Chemical Communications, 49 (86), pp. 10148-10150.
Tunbridge, G. A., Baruchello, R. and Caggiano, L., 2013. Mild and efficient capture and functionalisation of CO2 using silver(I) oxide and application to 13C-labelled dialkyl carbonates. RSC Advances, 3 (14), pp. 4613-4621.
Tunbridge, G. A., Oram, J. and Caggiano, L., 2013. Design, synthesis and antiproliferative activity of indole analogues of indanocine. MedChemComm, 4 (11), pp. 1452-1456.
Ciupa, A., Mahon, M., De Bank, P. and Caggiano, L., 2012. Simple pyrazoline and pyrazole “turn on” fluorescent sensors selective for Cd2+ and Zn2+ in MeCN. Organic and Biomolecular Chemistry, 10 (44), pp. 8753-8757.
Ciupa, A., Griffiths, N. J., Light, S. K., Wood, P. J. and Caggiano, L., 2011. Design, synthesis and antiproliferative activity of urocanic-chalcone hybrid derivatives. MedChemComm, 2 (10), pp. 1011-1015.
Judd, K. E. and Caggiano, L., 2011. Bi(OTf)3-catalysed prenylation of electron-rich aryl ethers and phenols with isoprene: a direct route to prenylated derivatives. Organic and Biomolecular Chemistry, 9 (14), pp. 5201-5210.
Judd, K. E., Mahon, M. F. and Caggiano, L., 2009. Efficient synthesis of tetrahydro-β-carbolin-1-one and dihydroisoquinolin-1-one derivatives as versatile intermediates. Synthesis, 2009 (16), pp. 2809-2817.
Nolasco, L., Perez Gonzalez, M., Caggiano, L. and Jackson, R. F. W., 2009. Application of Negishi Cross-Coupling to the Synthesis of the Cyclic Tripeptides OF4949-III and K-13. Journal of Organic Chemistry, 74 (21), pp. 8280-8289.
Drago, C., Walker, E. J., Caggiano, L. and Jackson, R. F. W., 2009. Enantioselective oxidation of an alkyl aryl sulfide:Synthesis of (S)-(-)-methyl p-Bromophenyl sulfoxide. Organic Syntheses, 86, pp. 121-129.
Caggiano, L., Jackson, R. F. W., Meijer, A. J. H. M., Pickup, B. T. and Wilkinson, K. A., 2008. Ionisation of the zinc/iodine bond of alkylzinc iodides in dimethylformamide from theory and experiment. Chemistry - A European Journal, 14 (29), p. 8798.
Oswald, C. L., Carrillo-Marquez, T., Caggiano, L. and Jackson, R. F. W., 2008. Negishi cross-coupling reactions of alpha-amino acid-derived organozinc reagents and aromatic bromides. Tetrahedron, 64 (4), pp. 681-687.
Bartrum, H. E., Adams, H., Caggiano, L. and Jackson, R. F. W., 2008. Synthesis of β2-homophenylalanine derivatives by Negishi cross-coupling reactions. Tetrahedron, 64 (17), pp. 3701-3712.
Loghmani-Khouzani, H., Poorheravi, M. R., Sadeghi, M. M. M., Caggiano, L. and Jackson, R. F. W., 2008. α-Fluorination of β-ketosulfones by Selectfluor™ F–TEDA–BF4. Tetrahedron, 64 (30-31), pp. 7419-7425.