Dr Vittorio Caprio
Dr Vittorio Caprio
Senior Lecturer in Organic/Medicinal Chemistry and Admissions Tutor Chemistry Programmes
My profile
Biography
Vittorio Caprio graduated with a degree in Chemistry from The University of Reading in 1994 and gained a PhD, in Organic Synthesis, under the supervision of Prof. John Mann, from the same institution in 1998. He subsequently moved to The University of Auckland, New Zealand to carry out postdoctoral work with Prof. Margaret Brimble and began a lectureship at the same institute in 2001.
In 2009 he relocated back to the UK to take up his current post at Manchester Metropolitan University where he is , currently, a Senior Lecturer in Organic and Pharmaceutical Chemistry pursuing research interests in total synthesis, biocatalyst-mediated synthetic strategies and medicinal chemistry with a focus on the design of anti-inflammatory and neuroactive small molecules. Vittorio also serves as Admissions Tutor for Chemistry Programmes.
Other academic service (administration and management)
Admissions Tutor Chemistry Programmes
Alumni Relations Coordinator Chemistry Programmes
Outreach Coordinator Chemistry Programmes
Interests and expertise
Our interests focus on the design and synthesis of molecules of therapeutic interest. These range from small molecules as part of medicinal chemistry programmes to structurally complex, natural product-like targets. A main aim is the design of highly efficient strategies that can be applied to provide enabling quantities of targets and analogues. Thus, we have developed an interest in the use of nitrone-functionalised core structure motifs which display a sufficently diverse reactivity profile to conveniently provide access to a wide range of analogues.
In addition, we have developed interests in the high regiospecificity and stereoselectivity of biocatalysts to achieve our aim. Specifically, in collaboration with Bea Macia at MMU and Elaine O’Reilly at UCD, we have applied a transaminase-triggered aza-Michael process to access multiply stereogenic alkaloid skeleta in high ee in one step from simple, achiral, acyclic precursors.
Our interests have generated projects in medicinal chemistry. We have developed novel molecules for the inhibition of proinflammatory CRP dissociation in collaboration with Targu-Mures University in Romania and Immunitat Und Seele in Munich and we have programme based on the design of interleukin-1 inhibitors with Baoqiang Guo at MMU.
Projects
The main research interests of the Caprio group are focused on the development of novel synthetic routes to bioactive natural products and their use in interdisciplinary studies in chemical biology/drug lead generation. We have special interests in:
1. The use of nitrones in organic synthesis. We have developed routes to chiral, non-racemic nitrone derivatives of 3-hydroxypiperidines and functionalised tetrahydroisoquinolines which provide access to a range of sterodefined products for use in total synthesis and as novel scaffolds in drug discovery.
2. Construction of spirocyclic alkaloid scaffolds. The group utilize an intramolecular cycloaddition/oxidative ring opening strategy to access core structure analogues of a range of spirocyclic alkaloids including pinnaic acid, halichlorine and histrionicotoxin.
3. Biocatalysis in the total synthesis of complex alkaloids. We work in collaboration with Dr Elaine O’Reilly at UCD, Dublin on the application of ecoupling of a transaminase mediated-reductive amination/aza-Michael cascade we pioneered towardsthe highly efficient enantioselective preparation of alkaloid scaffolds.
4. Development of drug leads which to disrupt a number of antiinflammatory mechanisms included inhibition of CRP dissociation, Il-1 antagonism and inhibition of PLA2 activity.
Applications for PhD and postdoctoral positions, working broadly on the research projects highlighted, are welcomed. Please contact me directly via email: [email protected].
Teaching
I teach organic and medicinal chemistry across all levels from 1st yr to MChem:
1st Yr. Introduction to Drug Discovery - Pharmacokinetics and Drug Sources
2nd Yr. Chemistry of the Carbonyl Group - Enolates and Conjugate Additions
3rd Yr. Advanced Pharmaceutical Chemistry - Drug-Target Binding, General SAR Tactics, Case Studies - Cholinergic, Adrenergic and Opiate drugs.
MChem. Advanced Synthesis, Analysis and Catalysis - Protecting Group Strategies. Stabililsed Carbanions and Umpolung Strategies.
Supervision
Vittorio has supervised numerous PhD and Masters students to completion.
Applications for PhD and postdoctoral positions, working broadly on the research projects highlighted, are welcomed. Please contact me directly via email: [email protected].
Research outputs
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Books (authored/edited/special issues)
Caprio, V., Williams, J., Caprio, Williams, (2009) Catalysis in Asymmetric Synthesis. John Wiley & Sons.
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Chapters in books
Caprio, V. (2008) 'Pyridines and their benzo derivatives: Reactivity of substituents.' Comprehensive Heterocyclic Chemistry III. pp. 101-169.
Caprio, V. (2004) 'Ketones: Dialkyl ketones.' Comprehensive Organic Functional Group Transformations II. pp. 135-214.
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Reports
Caprio, V., Sutcliffe, O.B., Mewis, R. (2018) Analysis of the reduction product of 3-nitrobenzaldehyde using Pulsar. Oxford Instruments.
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Journal articles
Griffiths, E.F., Dixon, J.A., Caffyn, A.J.M., Langley, S.K., Maciá, B., Caprio, V., Mewis, R.E. (2024) 'Determination of the pK a Value of a Brønsted Acid by 19 F NMR Spectroscopy.' Magnetic Resonance in Chemistry,
Pastorello, Y., Russo, A.P., Bănescu, C., Caprio, V., Gáll, Z., Potempa, L., Cordoș, B., Di Napoli, M., Slevin, M. (2024) 'Brain Vascular Expression of Monomeric C-Reactive Protein Is Blocked by C10M Following Intraperitoneal Injection in an ApoE-/- Murine Model of Dyslipidemia: An Immunohistochemical Analysis.' Cureus, 16(5)
Pastorello, Y., Manu, D., Sawkulycz, X., Caprio, V., Banescu, C., Dobreanu, M., Potempa, L., Di Napoli, M., Slevin, M. (2024) 'mCRP-Induced Focal Adhesion Kinase-Dependent Monocyte Aggregation and M1 Polarization, which was partially blocked by the C10M Inhibitor.' International Journal of Molecular Sciences, 25(6)
Taday, F., Ryan, J., Argent, S.P., Caprio, V., Maciá, B., O'Reilly, E. (2020) 'Asymmetric Construction of Alkaloids Employing a Key ω-Transaminase Cascade.' Chemistry - A European Journal, 26(17) pp. 3729-3732.
Eastman, H., Ryan, J., Caprio, V., Maciá, B., O'Reilly, E. (2019) 'Alcohol Dehydrogenase Triggered Oxa‐Michael Reaction for the Asymmetric Synthesis of Disubstituted Tetrahydropyrans and Tetrahydrofurans.' ChemCatChem, 11(16) pp. 3760-3762.
Slevin, M., Iemma, R.S., Zeinolabediny, Y., Liu, D., Ferris, G.R., Caprio, V., Phillips, N., Di Napoli, M., Guo, B., Zeng, X., AlBaradie, R., Binsaleh, N.K., McDowell, G., Fang, W.H. (2018) 'Acetylcholine Inhibits Monomeric C-Reactive Protein Induced Inflammation, Endothelial Cell Adhesion, and Platelet Aggregation; A Potential Therapeutic?.' Frontiers in immunology, 9
Flores-Ferrándiz, J., Carter, N., González-Soria, M.J., Wasinska, M., Gill, D., Maciá, B., Caprio, V. (2018) 'Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines vial-phenylalanine-derived dihydroisoquinoline N-oxides..' Organic and Biomolecular Chemistry, 16(38) pp. 6961-6968.
Caprio, V., Badimon, L., Di Napoli, M., Fang, W.H., Ferris, G.R., Guo, B., Iemma, R.S., Liu, D., Zeinolabediny, Y., Slevin, M. (2018) 'pCRP-mCRP dissociation mechanisms as potential targets for the development of small-molecule anti-inflammatory chemotherapeutics.' Frontiers in Immunology, 9
Caprio, V., McLachlan, A.S., Sutcliffe, O.B., Williamson, D.C., Mewis, R.E. (2018) 'Structural elucidation of unknowns: a spectroscopic investigation with an emphasis on 1D and 2D nuclear magnetic resonance spectroscopy.' Chemistry: Bulgarian Journal of Science Education, 27(2) pp. 223-234.
Ryan, J., Šiaučiulis, M., Gomm, A., Maciá, B., O’Reilly, E., Caprio, V. (2016) 'Transaminase Triggered Aza-Michael Approach for the Enantioselective Synthesis of Piperidine Scaffolds.' Journal of the American Chemical Society, 138(49) pp. 15798-15800.
Archibald, G., Lin, C.P., Boyd, P., Barker, D., Caprio, V. (2012) 'A divergent approach to 3-piperidinols: A concise syntheses of (+)-swainsonine and access to the 1-substituted quinolizidine skeleton.' Journal of Organic Chemistry, 77(18) pp. 7968-7980.
Stubbing, L.A., Li, F.F., Furkert, D.P., Caprio, V.E., Brimble, M.A. (2012) 'Access to 2-alkyl chromanones via a conjugate addition approach.' Tetrahedron, 68(34) pp. 6948-6956.
Ward, J., Johnson, A.B., Clark, G.R., Caprio, V. (2009) 'The synthesis of functionalised bicyclo[3.3.1]nonanes related to huperzine A.' Synthesis, (20) pp. 3411-3418.
Ward, J., Caprio, V. (2009) 'Synthesis of the bicyclo[3.3.1]nonane core of huperzine a and novel pyridine-fused tricycles by cyclisation of pyridine-based radicals.' Heterocycles, 79(C) pp. 791-804.
Yang, S.H., Clark, G.R., Caprio, V. (2009) 'A concise approach to the core structures of pinnaic acid and halichlorine.' Organic & Biomolecular Chemistry, 7(14) pp. 2981-2981.
Ashoorzadeh, A., Archibald, G., Caprio, V. (2009) 'Synthetic evaluation of an enantiopure tetrahydropyridine N-oxide. Synthesis of (+)-febrifugine.' Tetrahedron, 65(24) pp. 4671-4680.
Crimmins, D., Dimitrov, I., O'Connor, P.D., Caprio, V., Brimble, M.A. (2008) 'A facile synthesis of a spironitrone and a study of its cycloaddition and nuoleophilic addition reactions.' Synthesis, (20) pp. 3319-3325.
Yang, S.H., Caprio, V. (2007) 'A concise and flexible synthesis of the core structure of pinnaic acid.' Synlett, (8) pp. 1219-1222.
Peng, H., Soeller, C., Vigar, N.A., Caprio, V., Travas-Sejdic, J. (2007) 'Label-free detection of DNA hybridization based on a novel functionalized conducting polymer.' Biosensors and Bioelectronics, 22(9-10) pp. 1868-1873.
Caprio, V. (2006) 'Recent advances in organocopper chemistry.' Letters in Organic Chemistry, 3(5) pp. 339-349.
Ward, J., Caprio, V. (2006) 'A radical mediated approach to the core structure of huperzine A.' Tetrahedron Letters, 47(4) pp. 553-556.
Ashoorzadeh, A., Caprio, V. (2005) 'A convergent enantioselective synthesis of the anti-malarial agent (+)-febrifugine.' Synlett, (2) pp. 346-348.
Caprio, V., Brimble, M.A., Furkert, D.P. (2001) 'Synthesis of the novel 1,7,9-trioxadispiro[4.1.5.2]-tetradecane ring system present in the spirolides.' Tetrahedron, 57(18) pp. 4023-4034.
Caprio, V.E., Jones, M.W., Brimble, M.A. (2001) '1-(Pyridin-3-yl)-4-(triethylsilyloxy)-2-butyn-1-ol.' Molecules, 6(3)
Caprio, V.E., Jones, M.W., Brimble, M.A. (2001) '1-(Pyridin-3-yl)but-2-yn-1,4-diol.' Molecules, 6(3)
Caprio, V.E., Jones, M.W., Brimble, M.A. (2001) 'Pyridine-3-carboxaldehyde O-methyloxime.' Molecules, 6(3)
Caprio, V.E., Jones, M.W., Brimble, M.A. (2001) 'tert-Butyl methoxy(2-propynyl)carbamate.' Molecules, 6(3)
Brimble, M.A., Caprio, V., Johnston, A.D., Sidford, M. (2001) 'Synthesis of Arylspiroketals Related to the Papulacandins via Generation of Phthalide Oxycarbenium Ions.' Synthesis, 2001(06) pp. 0855-0862.
Brimble, M.A., Caprio, V., Johnston, A.D., Sidford, M. (2001) 'Synthesis of arylspiroketals related to the papulacandins via generation of phthalide oxycarbenium ions.' Synthesis, (6) pp. 855-862.
Caprio, V.E., Jones, M.W., Brimble, M.A. (2001) '1-(2-Vinyl-pyridin-3-yl)propanal O-methyloxime and 1-(6-Vinyl-pyridin-3-yl) propanal O-methyloxime.' Molecules, 6(3)
Caprio, V., Guyen, B., Opoku-Boahen, Y., Mann, J., Gowan, S.M., Kelland, L.M., Read, M.A., Neidle, S. (2000) 'A novel inhibitor of human telomerase derived from 10h-indolo[3,2-b]quinoline.' Bioorganic and Medicinal Chemistry Letters, 10(18) pp. 2063-2066.
Brimble, M.A., Caprio, V.E., Johnston, A.D., Sidford, M.H. (2000) 'Synthesis of aryl spiroketals related to the papulacandins via allylation of phthalides.' Tetrahedron Letters, 41(20) pp. 3955-3958.
Baron, A., Caprio, V., Mann, J. (1999) 'Synthesis of key intermediates for a concise and convergent approach to the marine natural product eleutherobin.' Tetrahedron Letters, 40(52) pp. 9321-9324.
Caprio, V., Mann, J. (1998) 'Synthesis of novel chromeno[3,4-b]pyridinones.' Journal of the Chemical Society - Perkin Transactions 1, (19) pp. 3151-3155.