Royal College of Surgeons in Ireland Coláiste Ríoga na Máinleá in Éirinn

Professor Donal O'Shea

Photograph

Professor Donal O'Shea PhD

Head of Department of Pharmaceutical & Medicinal Chemistry

email: donalfoshea@rcsi.ie    Tel: +353-1-4022155


Biography

Professor, Hear of Department, Pharmaceutical & Medicinal Chemistry, Royal College of Surgeons in Ireland, 2013 - to date 

Associate Professor, Head of Organic Chemistry Section, School of Chemistry and Chemical Biology, Conway Institute, University College Dublin, 2007-2013

Senior Lecturer, School of Chemistry and Chemical Biology, University College Dublin, 2005-2007

Co-Director of the Centre for Synthesis and Chemical Biology, University College Dublin, 2002-2003

College Lecturer, Department of Chemistry, University College Dublin, 1999-2004

Research Scientist; Color Technology Research Division, Eastman Kodak Company, Rochester, New York, USA, 1997-1999

Postdoctoral Research Fellow; North Carolina State University, Raleigh, NC, USA, 1996-1997

Postdoctoral Research Fellow; Carnegie Mellon University, Pittsburgh, PA, USA, 1995-1996

Postdoctoral Research Fellow; University of Edinburgh, UK, 1993-1995

PhD (NUI) in Chemistry, University College Galway, 1993 

BSc (NUI) in Chemistry, University College Galway, 1990 


Research Interests

Overview

The central theme of my research lies in the advancement of new strategies for the synthesis and functional assessment of structurally complex molecules. Specific goals include the development of new light activated anti-cancer and anti-microbial agents, the investigation of novel concepts for drug selectivity and the generation of chemical tools to assist in gaining a molecular level insight into biological processes. My research has its foundations in medicinal organic chemistry and chemical biology with strong collaborative links with pharmacology, biological imaging and medicine.

On-going Research Projects (Details of on-going Research Projects)

Near-infrared fluorochromes for real-time in vitro and in vivo imaging; tools for chemical biology and fluorescence guided surgery.
A new class of photodynamic therapeutic agent with anti-cancer and anti-bacterial potential.
Innovative methodologies for pharmaceutical synthesis utilizing microflow reactors.
Mixed metal Li/K amides (LiNK chemistry) as new reagents for synthetic chemistry.

Research Group

Current Research Group:
Research group currently consists of four Ph.D. students and two postdoctoral researchers.

Students Graduated:
Twelve PhD and four MSc students graduated to date.


Representative Publications 
(Full List of Publications)

1. Daly, H.C.; Sampedro, G.; Bon, C.; Wu, D.; Ismail, G.; Cahill, R.A.; O'Shea D.F. BF2-azadipyrromethene NIR-emissive fluorophores with research and clinical potential. European Journal of Medicinal Chemistry, 2017, 135, 392-400.

2. Das M., Manvar A., Fox I., Roberts D.J., O'Shea D.F., Bu4N+-Controlled Addition and Olefination with Ethyl 2-(Trimethylsilyl) acetate via Silicon Activation. Synlett, 2017, 28, A-F.

3. Bao, L.L.; Bian, J.; Yan, Y.J.; Zhang, L.J.; O'Shea, D.F.; Chen, Z.L. In vitro and in vivo evaluation of a pyropheophorbide-a derivative as a potential photosensitizer for age-related macular degeneration. Biomedicine and Pharmacotherapy, 2017, 88, 1220.

4. Ge, Y.; O'Shea, D.F. Azadipyrromethenes: From Traditional Dye Chemistry to Leading Edge Applications. Chem. Soc. Rev., 2016, 45, 3846.  .

5. Grossi, M.; Morgunova, M.; Cheung, S; Dimitri Scholz, D.; Conroy, E.; Terrile, M.; Panarella, A.; Simpson, J.C.; Gallagher, W.M. O'Shea, D.F. Lysosome Triggered Near Infra-Red Fluorescence; Imaging of Cellular Trafficking Processes in Real-time. Nature Communications, 2016, 7, 10855.

6. Das, M.; O'Shea, D.F. Z-Stereoselective Aza-Peterson Olefinations with Bis(trimethylsilane) Reagents and Sulfinyl Imines. Organic Letters, 2016, 18, 336.

7. Wu, D.; Cheung, S.; Devocelle, M.; Zhang, L.; Chen, Z.L.; O'Shea, D.F. Synthesis and Assessment of a Maleimide Functionalized BF2 Azadipyrromethene Near-Infrared Fluorochrome. Chemical Communications, 2015, 51, 16667.

8. Manvar, A.; O'Shea, D.F. Trimethylsilyloxide Catalysed Peterson Olefinations with 2,2-Bis-(trimethylsilyl)-1,3-dithiane. European Journal of Organic Chemistry, 2015, 7259. 

9. Das, M.; O'Shea, D.F. Highly Selective Addition of a Broad Spectrum of TMS Pro-nucleophiles to N-tert-Butanesulfinylimines. Chemistry - A European Journal, 2015, 21, 18723.

10. Das, M.; O'Shea, D.F. Silyloxide-Promoted Diastereoselective Addition of Aryl and Heterocyclic Trimethylsilanes to N-tert-Butanesulfinylimines. Organic Letters, 2015, 17, 1962.

11. Manvar, A.; Fleming, P. O'Shea, D.F. General Ambient Temperature Benzylic Metalations Using Mixed-Metal Li/K-TMP Amide. Journal of Organic Chemistry, 2015, 80, 8727.

12. Das, M.; Manvar, A.; Jacolot, M.; Blangetti, M.; Jones, R.; O'Shea, D.F. Stereoselective Peterson Olefinations from Bench-stable Reagents and N-Phenyl Imines. Chemistry European Journal, 2015, 21, 8737. (Featured on front cover).

13. Wu, D.; Cheung, S.; Daly, R.; Burke, H.; Scanlan, E.M.; O'Shea, D.F. Synthesis and Glycoconjugation of an Azido-BF2-Azadipyrromethene Near-Infrared Fluorochrome. European Journal of Organic Chemistry, 2014, 6841.

14. Das, M., O'Shea, D.F. Bu4N+ Alkoxide-Initiated/Autocatalytic Addition Reactions with Organotrimethylsilanes. Journal of Organic Chemistry, 2014, 79, 5595. 

15. Unkelbach C, O’Shea DF. Strohmann C. Insight into the Metalation of Benzene and Toluene by Schlosser’s Base: A Bimetallic, Superbasic Cluster comprising PhK, PhLi and tBuOLi. Angew. Chem. Int. Ed., 2014, 53, 553.

16. Blangetti M, Muller-Bunz H. O'Shea DF.  First asymmetric synthesis of planar chiral [2.2]metacyclophanes. Chemical Communications, 2013, 49, 6125.

17. Wu Dan, O'Shea DF. Synthesis and Properties of BF2-3,3-Dimethyldiarylazadipyrromethene Near-Infrared Fluorophores. Organic Letters, 2013, 15, 3392.

18. Das M, O'Shea DF. Synthesis and application of benzyl-TMS derivatives as bench stable benzyl anion equivalents. Tetrahedron, 2013, 69, 6448.

19. Palma A, McDonnell S O, Rai D, Hall MJ, Grossi M, O'Shea DF. Mechanistic Insight into the Formation of Tetraarylazadipyrromethenes. Journal of Organic Chemistry, 2012, 77, 9304.

20. O'Connor AE, McGee MM, Likar Y, Ponomarev V, Callanan JJ, O'Shea DF, Byrne AT,
Gallagher WM. Mechanism of Cell Death Mediated by a Novel Non-Porphyrin Photodynamic Therapeutic: Dissection of the Apoptotic Pathway In Vitro and In Vivo.  International Journal of Cancer, 2012, 130, 705.

21. Blangetti M, Fleming P, O'Shea DF. Homo- and Hetero-Oxidative Coupling of Benzyl Anions. Journal of Organic Chemistry, 2012, 77, 2870.

22. Palma A, Alvarez LA, Scholz D, Frimannsson DO, Grossi M, Quinn SJ, O'Shea DF. Cellular Uptake Mediated Off/On Responsive Near-Infrared Fluorescent Nanoparticles. Journal of the American Chemical Society, 2011, 133, 19618.


Highlighted in C&EN News
http://cen.acs.org/articles/89/i49/SwitchFluorescence.html
see YouTube for example movie
http://www.youtube.com/watch?v=FjipbGTf8w4

23. Batat P, Cantuel M, Jonusauskas G, Palma A, O'Shea DF, McClenaghan N.D. BF2-Azadipyrromethenes: Probing the Excited-state Dynamics of a NIR Fluorophore and Photodynamic Therapy Agent. Journal of Physical Chemistry A, 2011, 115, 14034.

24. Fleming P, O'Shea DF. Controlled Anion Migrations with a Mixed Metal Li/K-TMP Amide: General Application to Benzylic Metalations. Journal of the American Chemical Society, 2011, 113, 1698.

25. Flavin K, Lawrence K, Bartelmess J, Tasior M, Navio C, Bittencourt C, O'Shea DF, Guldi DM, Giordani S. Synthesis and Characterization of Boron Azadipyrromethene Single-Wall Carbon Nanotube Electron Donor-Acceptor Conjugate. ACS Nano, 2011, 5, 1198.

26. Gessner VH, Strohmann C, Hogan A-ML, O'Shea DF. Mechanistic Insight into Stereoselective Intermolecular Carbolithiations. Chemistry A European Journal, 2011, 17, 2996.

27. Frimannsson DO, Grossi M, Murtagh J, Paradisis F, O'Shea DF. Light-Induced Antimicrobial Properties of a Brominated BF2-Chelated Tetraarylazadipyrromethene Photosensitizer.  Journal of Medicinal Chemistry, 2010, 53, 7337.

28. Tricotet T, O'Shea DF. Automated Generation and Reactions of 3-Hydroxymethylindoles in Continuous Flow Microreactors.  Chemistry A European Journal, 2010, 16, 6678.

29. Tasior M, O'Shea DF. BF2-Chelated Tetraarylazadipyrromethenes as NIR Fluorochromes. Bioconjugate Chemistry, 2010, 21, 1130.

30. Tricotet T, Fleming P, Cotter J, Hogan A-ML, Strohmann C, Gessner VH, O'Shea DF. Selective Vinyl C-H Lithiation of cis-Stilbenes.  Journal of the American Chemical Society, 2009, 131, 3142.

31. Hogan A-ML, O'Shea DF. Enantioselective Carbolithiation Initiated Cascade Reactions.  Journal of the American Chemical Society, 2006, 128, 10360.

32. McDonnell SO, Hall MJ, Allen LT, Byrne A. Gallagher WM, O'Shea DF. Supramolecular Photonic Therapeutic Agents.  Journal of the American Chemical Society, 2005, 127, 16360.
Highlighted in C&EN News, Science and Technology Concentrates, 2005, 28, p.27.

33. Gorman A, Killoran J, O'Shea C, Kenna T, Gallagher WM, O'Shea DF. In vitro demonstration of the heavy-atom effect for photodynamic therapy. Journal of the American Chemical Society, 2004, 126, 10619.

34. Coleman, CM; O'Shea, DF. New Organolithium addition methodology to diversely functionalised indoles. Journal of the American Chemical Society, 2003, 125, 4054.

Patents

1. O'Shea, DF, Killoran J, Gallagher WM. Compounds useful as photodynamic therapeutic agents. United States Patent No. 7,220,732, May 22, 2007.

2. O'Shea DF, Killoran J, Gallagher W.M. Compounds useful as photodynamic therapeutic agents. European Patent Application No: 03720375.9

3. O'Shea DF. Novel fluorescent near-infrared (NIR) dyes.  International Patent Application No: PCT/EP2010/065991.


Awards and Distinctions

Royal Society of Chemistry, Inaugural 2012 North/South of Ireland lectureship award.
Visiting Professor, March 2012 at Donghua University, Shanghai, China.
Visiting Professor, June 2011 at the University of Rennes 1, France.
Ulysses France / Ireland research exchange award.
Teacher of the Year Award 2011 and 2008 from the School of Medicine and Medical Sciences.
Visiting Professor, June 2008 at the École Nationale Supérieure de Cachan, CNRS, UniverSud, 61 av President Wilson, F-94230, Cachan, France.
Organizer of the 1st, 2nd and 3rd Bilateral Sino-Ireland Symposia on Frontiers in Synthetic Chemistry.
Research has been highlighted in international publications and media such as:
SciBX (Science-Business Exchange) 2010, Oct 14, Vol 3, No 40. see SciBX 3(40); doi:10.1038/scibx.2010.1220.
SYNFACTS, see Synfacts 2009, 6, 0656 and Synfacts 2005, 1, 0115.
Chemical & Engineering News, 2005, 28, p.27.
Chemical & Engineering News, 2011, Vol 89, Dec 5th, p.8.
http://cen.acs.org/articles/89/i49/SwitchFluorescence.html
YouTube: http://www.youtube.com/watch?v=FjipbGTf8w4