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Dr Lorenzo Caggiano

Senior Lecturer in Medicinal Chemistry

Telephone: (01225) 385709
E-mail: L.Caggiano@bath.ac.uk

Department of Pharmacy and Pharmacology
University of Bath (5 West - 3.6)
Claverton Down
Bath
BA2 7AY
ENGLAND

Google Scholar profile

Group Interests

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.

- From Daffodils to Drugs - Our work in the design and synthesis of novel analogues of natural products obtained from daffodils for the treatment of brain tumours was the subject of several recent interviews:

       





With Jonathan Ray

With Claire Cavanagh

Flower farmers have known for thousands of years that a freshly cut daffodil (narcissus) placed in a vase with other flowers will cause them to wilt and die prematurely. This simple observation led to the discovery that some molecules found in the daffodil bulb inhibit the growth of other plants, but much more importantly, that they also inhibit cancer in humans. Narciclasine and pancratistatin are molecules found in daffodil and are believed to be the “active ingredients” responsible for this anticancer activity. They display powerful activity against a wide range of cancers with little toxicity, and have shown excellent promise against Glioblastoma multiforme. This is a crucial area since only 10% of patients with Glioblastoma are alive 5 years after diagnosis.

Unfortunately, these molecules are difficult to isolate from the daffodil bulb so there is only a limited supply. Furthermore, these molecules are structurally complex, so chemical synthesis is also difficult, again limiting their availability. These issues have prevented further biological evaluation and clinical development of these molecules as potential new drugs to treat brain tumours.

Our research aim is to develop synthetic approaches to narciclasine derivatives that are easier to make, yet retain the potent therapeutic activities. Our research group has developed new ways of making the core structure of narciclasine in an efficient high-yielding single chemical step. Research funds will allow us to exploit our expertise and work closely in a multidisciplinary team with collaborations in Exeter, Bristol and Cardiff to develop compounds towards achieving our ultimate goal and identify new drugs to treat brain tumours. Funding from charities and Research Councils are vial in developing this research and we are very grateful of all of Sophie's fund-raising activities to-date and fully support her latest challenge Ride4Simon 2019.

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- Potential new route for treating pancreatic cancer from tropical flowers - In collaboration with Dr Simon Lewis (University of Bath) and Prof. Suresh Awale (University of Toyama, Japan), we have chemically synthesised compounds originally isolated from flowering plants in SE-Asia, which were well-known locally as medicinal plants. The natural product of interest is "Grandifloracin" which reduces the ability of pancreatic cancer cells to survive their environment. We report two novel derivatives that display enhanced activity that is of great interest in a new approach to treating pancreatic cancers. Publication


Treatment of Pancreatic cancer cells (PANC‐1) with our new derivative inhibits cell mobility within 30 minutes and induced cell death within 4 h. PANC‐1 cells cultured under the same conditions in nutrient deprived media (NDM, control) continued to survive until the end of the experiment (24 h). This study demonstrates the first live evidence of the anticancer therapeutic potential of our new derivative.

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We are also interested in other research projects and in collaboration with Dr Giordano Pula, we have been awarded £219,000 by the British Heart Foundation to explore novel prodrugs developed by our group for preventing strokes. News item.

Related publications
  • Sidechain diversification of grandifloracin allows identification of analogues with enhanced anti-austerity activity against human PANC-1 pancreatic cancer cells. Alexander BE, Sun S, Palframan MJ, Kociok-Köhn G, Caggiano L, Awale S and Lewis SEChemMedChem, 202015, 125-135 Open Access
  • The Enone Motif of (+)-Grandifloracin is Not Essential for Anti-Austerity Antiproliferative Activity. Ali Khan M, Wood PJ, Lamb-Guhren NM, Caggiano L, Kociok-Kohn G, Tosh D, Lewis SE Bioorg. Med. Chem. Lett., 201424, 2815-2819 Open Access
  • Design, synthesis and antiproliferative activity of indole analogues of indanocine.
  • Tunbridge GA, Oram J and Caggiano L MedChemComm, 20134, 1452-1456 Open Access
  • Synthesis and antiproliferative activity of some 3-(pyrid-2-yl)-pyrazolines.
  • Ciupa A, De Bank PA, Mahon MF, Wood PJ and Caggiano L MedChemComm, 20134, 956 - 961 Open Access
  • Design, synthesis and growth inhibition of urocanic-chalcone hybrid derivatives.
  • Ciupa A, Griffiths NJ, Light SK, Wood PJ and Caggiano L MedChemComm, 2011, 2, 1011-1015
  • Efficient Synthesis of Tetrahydro-b-carbolin-1-one and Dihydroisoquinolin-1-one Derivatives as Versatile Intermediates.
  • Judd KE; Mahon MF and Caggiano L. Synthesis, 2009, 16, 2809-2817

    Cancer Research at Bath (CR@B)
    Lorenzo Caggiano is a member of the organising committee of Cancer Research at Bath (CR@B). Gave an overview of cancer research activities in Medicinal Chemistry in Bath during a public lecture as part of the FutureLearn Massive Open Online Course (MOOC) on cancer.

    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.

  • Mild and Efficient Capture and Functionalisation of CO2 using Silver(I) Oxide and Application to 13C-labelled Dialkyl Carbonates. Tunbridge GA, Baruchello R and Caggiano L RSC Advances. 2013, 3, 4613 - 4621


  • Novel Prenylation Reactions
    We have discovered an efficient procedure for the prenylation of various substituted arenes.

  • Bi(OTf)3-catalysed prenylation of electron-rich aryl ethers and phenols with isoprene: a direct route to prenylated derivatives. Judd KE and Caggiano L Org. Biomol. Chem., 2011, 9, 5201-5210


  • 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.

  • Simple pyrazoline and pyrazole "turn on" fluorescent sensors selective for Cd2+ and Zn2+ in MeCN. Ciupa A, Mahon MF, De Bank PA and Caggiano L Org. Biomol. Chem., 201210, 8753-8757


  • 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 multicellular aggregation of modified cells selectively in the presence of Fe(III) ions within minutes.

  • Multicellular aggregation of maltol-modified cells triggered by Fe3+ ions. Ciupa A, De Bank PA and Caggiano L ChemCommun., 201349, 10148-10150 Open Access

  • Administrative Duties

    Director of Studues for Postgraduate Research Students; Departmental Higher Degrees Committee member; Member of the Department Learning, Teaching & Quality Committee (DLTQC); Deputy Work Load Model co-ordinator; member of the Research Staff Working Group; Departmental Research Staff Co-ordinator; Widening Participations departmental representative; Departmental Outreach Contact; Departmental Web Contact for News and Twitter.

    Recent awards/nominations:
    - Nominated for the University John Willis Teaching Award 2014.
    - Received a Faculty of Science "Recognising Excellence" Award 2014
    - Nominated and awarded the University John Willis Teaching Award 2015.
    - Received an Outstanding Contribution Award 2015, "in recognition for sustained exceptional performance over the past year".
    - Nominated for the University Mary Tasker Award for teaching 2016
    - Nominated for the University Mary Tasker Award for teaching 2017
    - Nominated for University Innovation in Learning & Teaching Award 2017
    - Nominated for the Faculty Teaching Award 2017
    - Nominated “Personal Tutor of the year” University of Bath SU 2018
    - Nominated for the Faculty Teaching Award 2019
    - Nominated for the University Mary Tasker Award for teaching 2020

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