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Dr Matthew Tredwell
Senior Lecturer in Medicinal Chemistry and Senior Researcher Fellow
- Available for postgraduate supervision
Overview
Tredwell Group – core research areas
- organofluorine chemistry
- transition-metal catalysis
- radiochemical synthesis
- radiotracer development
- automated synthesis
- clinical translation
Publication
2024
- Ortalli, S., Ford, J., Szpera, R., Stoessel, B., Trabanco, A. A., Tredwell, M. and Gouverneur, V. 2024. 18F-Difluoromethyl(ene) motifs via oxidative fluorodecarboxylation with [18F]Fluoride. Organic Letters 26(43), pp. 9368-9372. (10.1021/acs.orglett.4c03611)
- Ford, J., Ortalli, S., Chen, Z., Sap, J., Tredwell, M. and Gouverneur, V. 2024. Expedient access to 18F-fluoroheteroarenes via deaminative radiofluorination of aniline-derived pyridinium salts. Angewandte Chemie 63(26), article number: e202404945. (10.1002/anie.202404945)
- Ortalli, S., Ford, J., Trabanco, A. A., Tredwell, M. and Gouverneur, V. 2024. Photoredox nucleophilic (radio)fluorination of alkoxyamines. Journal of the American Chemical Society 146(17), pp. 11599-11604. (10.1021/jacs.4c02474)
2022
- Sap, J. B. I. et al. 2022. [18F]Difluorocarbene for Positron Emission Tomography. Nature 606, pp. 102-108. (10.1038/s41586-022-04669-2)
- Gendron, T. et al. 2022. Multi‐patient dose synthesis of [18F] Flumazenil via a copper‐mediated 18F‐fluorination. EJNMMI Radiopharmacy and Chemistry 7, article number: 5. (10.1186/s41181-022-00158-z)
2019
- Tredwell, M. 2019. Expanding the 18F-radiochemical space: synthesis and applications of 1,1-18F-difluorinated alkenes. SYNLETT 30(12), pp. 1371-1376. (10.1055/s-0037-1611764)
- Frost, A. B., Brambilla, M., Exner, R. and Tredwell, M. 2019. Synthesis and derivatization of 1,1-[18 F] difluorinated alkenes. Angewandte Chemie 131(2), pp. 482-486. (10.1002/ange.201810413)
- Frost, A. B., Brambilla, M., Exner, R. M. and Tredwell, M. 2019. Synthesis and derivatization of 1,1-[18 F] difluorinated alkenes. Angewandte Chemie International Edition 58(2), pp. 472-476. (10.1002/anie.201810413)
2018
- Verhoog, S. et al. 2018. 18F-trifluoromethylation of unmodified peptides with 5-18F-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate. Journal of the American Chemical Society 140(5), pp. 1572-1575. (10.1021/jacs.7b10227)
2017
- Brambilla, M. and Tredwell, M. 2017. Palladium-catalyzed Suzuki-Miyaura cross-coupling of secondary α-(trifluoromethyl)benzyl tosylates. Angewandte Chemie 129(39), pp. 12143-12147. (10.1002/ange.201706631)
- Brambilla, M. and Tredwell, M. 2017. Palladium-catalyzed Suzuki-Miyaura cross-coupling of secondary α-(trifluoromethyl)benzyl tosylates. Angewandte Chemie International Edition 56(39), pp. 11981-11985. (10.1002/anie.201706631)
- Taylor, N. J. et al. 2017. Derisking the Cu-mediated 18F-fluorination of heterocyclic positron emission tomography radioligands. Journal of the American Chemical Society 139(24), pp. 8267-8276. (10.1021/jacs.7b03131)
2016
- Wilson, T. C., McSweeney, G., Preshlock, S., Verhoog, S., Tredwell, M., Cailly, T. and V{e, . 2016. Radiosynthesis of SPECT tracers via a copper mediated123I iodination of (hetero)aryl boron reagents. Chemical Communications 52(90), pp. 13277--13280. (10.1039/c6cc07417k)
- Preshlock, S. et al. 2016. Enhanced copper-mediated 18F-fluorination of aryl boronic esters provides eight radiotracers for PET applications. Chemical Communications 52(54), pp. 8361-8364. (10.1039/c6cc03295h)
- Preshlock, S., Tredwell, M. and Gouverneur, V. 2016. 18F-labeling of arenes and aeteroarenes for applications in Positron Emission Tomography. Chemical Reviews 116(2), pp. 719-766. (10.1021/acs.chemrev.5b00493)
2015
- Buckingham, F. et al. 2015. Oxidative fluorination of N-arylsulfonamides. Journal of Fluorine Chemistry 180, pp. 33--39. (10.1016/j.jfluchem.2015.07.030)
- Khotavivattana, T. et al. 2015. 18F-Labeling of Aryl-SCF3, -OCF3and -OCHF2with [18F]Fluoride. Angewandte Chemie International Edition 54(34), pp. 9991-9995. (10.1002/anie.201504665)
- Verhoog, S. et al. 2015. Silver-mediated 18F-labeling of aryl-CF3 and aryl-CHF2 with 18F-fluoride. SYNLETT 27(1), pp. 25-28. (10.1055/s-0035-1560592)
- Hueting, R. et al. 2015. A dual radiolabelling approach for tracking metal complexes: investigating the speciation of copper bis(thiosemicarbazonates) in vitro and in vivo.. Metallomics : integrated biometal science 7(5), pp. 795-804. (10.1039/c4mt00330f)
2014
- Tredwell, M. et al. 2014. A general copper-mediated nucleophilic18F fluorination of arenes. Angewandte Chemie International Edition 53(30), pp. 7751-7755. (10.1002/anie.201404436)
- Emer, E. et al. 2014. Diversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(diazo-2,2,2-trifluoroethyl)arenes.. Organic Letters 16(22), pp. 6004-6007. (10.1021/ol5030184)
- O'Brien, E. R. et al. 2014. Glial activation in the early stages of brain metastasis: TSPO as a diagnostic biomarker.. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 5(2), pp. 275-280. (10.2967/jnumed.113.127449)
- Anthony, D. C. et al. 2014. Anti-CD20 inhibits T cell-mediated pathology and microgliosis in the rat brain.. Annals of Clinical and Translational Neurology 1(9), pp. 659-669. (10.1002/acn3.94)
- Hueting, R. et al. 2014. A comparison of the behavior of (64)Cu-acetate and (64)Cu-ATSM in vitro and in vivo.. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 55(1), pp. 128-134. (10.2967/jnumed.113.119917)
2013
- Huiban, M. et al. 2013. A broadly applicable [18F]trifluoromethylation of aryl and heteroaryl iodides for PET imaging. Nature Chemistry 5(11), pp. 941-944. (10.1038/nchem.1756)
- Benedetto, E., Tredwell, M., Hollingworth, C., Khotavivattana, T., Brown, J. M. and Gouverneur, V. 2013. Regio- and stereoretentive synthesis of branched, linear (E)- and (Z)-allyl fluorides from allyl carbonates under Ir-catalysis. Chem. Sci. 4(1), pp. 89-96. (10.1039/c2sc21789a)
- Mizuta, S. et al. 2013. Catalytic decarboxylative fluorination for the synthesis of tri- and difluoromethyl arenes.. Organic Letters 15(11), pp. 2648-2651. (10.1021/ol4009377)
2012
- Benedetto, E., Keita, M., Tredwell, M., Hollingworth, C., Brown, J. M. and Gouverneur, V. 2012. Platinum-catalyzed substitution of allylic fluorides. Organometallics 31(4), pp. 1408-1416. (10.1021/om201029m)
- Tredwell, M. and Gouverneur, V. 2012. 1.5 fluorine in medicinal chemistry: importance of chirality. In: Comprehensive chirality., Vol. 1. Reference module in Chemistry, Molecular Sciences and Chemical Engineering London: Elsevier, pp. 70--85., (10.1016/b978-0-08-095167-6.00106-3)
- Gao, Z. et al. 2012. Metal-free oxidative fluorination of phenols with [18F]fluoride. Angewandte Chemie International Edition 51(27), pp. 6733-6737. (10.1002/anie.201201502)
- Tredwell, M. and Gouverneur, V. 2012. 18F labeling of arenes. Angewandte Chemie International Edition 51(46), pp. 11426-11437. (10.1002/anie.201204687)
2011
- Hollingworth, C. et al. 2011. Palladium-catalyzed allylic fluorination. Angewandte Chemie International Edition 50(11), pp. 2613-2617. (10.1002/anie.201007307)
- Kersemans, V. et al. 2011. Hypoxia imaging using PET and SPECT: the effects of anesthetic and carrier gas on [Cu]-ATSM, [Tc]-HL91 and [F]-FMISO tumor hypoxia accumulation.. PLoS One 6(11), article number: e25911. (10.1371/journal.pone.0025911)
2010
- Tredwell, M. J., Gulias, M., Gaunt Bremeyer, N., Johansson, C. C. C., Collins, B. S. L. and Gaunt, M. J. 2010. Palladium(II)-catalyzed C-H bond arylation of electron-deficient arenes at room temperature. Angewandte Chemie International Edition 50(5), pp. 1076-1079. (10.1002/anie.201005990)
2008
- Tredwell, M., Luft, J. A. R., Schuler, M., Tenza, K., Houk, K. N. and Gouverneur, V. 2008. Fluorine-directed diastereoselective iodocyclizations. Angewandte Chemie International Edition 47(2), pp. 357-360. (10.1002/anie.200703465)
2007
- Kostov, G., Tredwell, M., Gouverneur, V. and Ameduri, B. 2007. Kinetics of radical copolymerization of [1-(fluoromethyl)vinyl]benzene with chlorotrifluoroethylene. Journal of Polymer Science Part A: Polymer Chemistry 45(17), pp. 3843-3850. (10.1002/pola.22134)
- Teare, H., Huguet, F., Tredwell, M., Thibaudeau, S., Luthra, S. and Gouveneur, V. 2007. A convergent approach for the synthesis of fluorinated sphingosine analogues. Archive for Organic Chemistry 2007(10), pp. 232-244. (10.3998/ark.5550190.0008.a14)
- Sawicki, M., Kwok, A., Tredwell, M. and Gouverneur, V. 2007. Single and double stereoselective fluorination of (E)-allylsilanes. Beilstein Journal of Organic Chemistry 3(1), pp. 34. (10.1186/1860-5397-3-34)
2006
- Tredwell, M. and Gouverneur, V. 2006. Electrophilic fluorination of organosilanes. Org. Biomol. Chem. 4(1), pp. 26-32. (10.1039/b513399h)
2005
- Tredwell, M., Tenza, K., Pacheco, M. C. and Gouverneur, V. 2005. Synthesis of novel enantiopure fluorinated building blocks from acyclic chiral allylsilanes.. Organic Letters 7(20), pp. 4495-4497. (10.1021/ol0518535)
Articles
- Ortalli, S., Ford, J., Szpera, R., Stoessel, B., Trabanco, A. A., Tredwell, M. and Gouverneur, V. 2024. 18F-Difluoromethyl(ene) motifs via oxidative fluorodecarboxylation with [18F]Fluoride. Organic Letters 26(43), pp. 9368-9372. (10.1021/acs.orglett.4c03611)
- Ford, J., Ortalli, S., Chen, Z., Sap, J., Tredwell, M. and Gouverneur, V. 2024. Expedient access to 18F-fluoroheteroarenes via deaminative radiofluorination of aniline-derived pyridinium salts. Angewandte Chemie 63(26), article number: e202404945. (10.1002/anie.202404945)
- Ortalli, S., Ford, J., Trabanco, A. A., Tredwell, M. and Gouverneur, V. 2024. Photoredox nucleophilic (radio)fluorination of alkoxyamines. Journal of the American Chemical Society 146(17), pp. 11599-11604. (10.1021/jacs.4c02474)
- Sap, J. B. I. et al. 2022. [18F]Difluorocarbene for Positron Emission Tomography. Nature 606, pp. 102-108. (10.1038/s41586-022-04669-2)
- Gendron, T. et al. 2022. Multi‐patient dose synthesis of [18F] Flumazenil via a copper‐mediated 18F‐fluorination. EJNMMI Radiopharmacy and Chemistry 7, article number: 5. (10.1186/s41181-022-00158-z)
- Tredwell, M. 2019. Expanding the 18F-radiochemical space: synthesis and applications of 1,1-18F-difluorinated alkenes. SYNLETT 30(12), pp. 1371-1376. (10.1055/s-0037-1611764)
- Frost, A. B., Brambilla, M., Exner, R. and Tredwell, M. 2019. Synthesis and derivatization of 1,1-[18 F] difluorinated alkenes. Angewandte Chemie 131(2), pp. 482-486. (10.1002/ange.201810413)
- Frost, A. B., Brambilla, M., Exner, R. M. and Tredwell, M. 2019. Synthesis and derivatization of 1,1-[18 F] difluorinated alkenes. Angewandte Chemie International Edition 58(2), pp. 472-476. (10.1002/anie.201810413)
- Verhoog, S. et al. 2018. 18F-trifluoromethylation of unmodified peptides with 5-18F-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate. Journal of the American Chemical Society 140(5), pp. 1572-1575. (10.1021/jacs.7b10227)
- Brambilla, M. and Tredwell, M. 2017. Palladium-catalyzed Suzuki-Miyaura cross-coupling of secondary α-(trifluoromethyl)benzyl tosylates. Angewandte Chemie 129(39), pp. 12143-12147. (10.1002/ange.201706631)
- Brambilla, M. and Tredwell, M. 2017. Palladium-catalyzed Suzuki-Miyaura cross-coupling of secondary α-(trifluoromethyl)benzyl tosylates. Angewandte Chemie International Edition 56(39), pp. 11981-11985. (10.1002/anie.201706631)
- Taylor, N. J. et al. 2017. Derisking the Cu-mediated 18F-fluorination of heterocyclic positron emission tomography radioligands. Journal of the American Chemical Society 139(24), pp. 8267-8276. (10.1021/jacs.7b03131)
- Wilson, T. C., McSweeney, G., Preshlock, S., Verhoog, S., Tredwell, M., Cailly, T. and V{e, . 2016. Radiosynthesis of SPECT tracers via a copper mediated123I iodination of (hetero)aryl boron reagents. Chemical Communications 52(90), pp. 13277--13280. (10.1039/c6cc07417k)
- Preshlock, S. et al. 2016. Enhanced copper-mediated 18F-fluorination of aryl boronic esters provides eight radiotracers for PET applications. Chemical Communications 52(54), pp. 8361-8364. (10.1039/c6cc03295h)
- Preshlock, S., Tredwell, M. and Gouverneur, V. 2016. 18F-labeling of arenes and aeteroarenes for applications in Positron Emission Tomography. Chemical Reviews 116(2), pp. 719-766. (10.1021/acs.chemrev.5b00493)
- Buckingham, F. et al. 2015. Oxidative fluorination of N-arylsulfonamides. Journal of Fluorine Chemistry 180, pp. 33--39. (10.1016/j.jfluchem.2015.07.030)
- Khotavivattana, T. et al. 2015. 18F-Labeling of Aryl-SCF3, -OCF3and -OCHF2with [18F]Fluoride. Angewandte Chemie International Edition 54(34), pp. 9991-9995. (10.1002/anie.201504665)
- Verhoog, S. et al. 2015. Silver-mediated 18F-labeling of aryl-CF3 and aryl-CHF2 with 18F-fluoride. SYNLETT 27(1), pp. 25-28. (10.1055/s-0035-1560592)
- Hueting, R. et al. 2015. A dual radiolabelling approach for tracking metal complexes: investigating the speciation of copper bis(thiosemicarbazonates) in vitro and in vivo.. Metallomics : integrated biometal science 7(5), pp. 795-804. (10.1039/c4mt00330f)
- Tredwell, M. et al. 2014. A general copper-mediated nucleophilic18F fluorination of arenes. Angewandte Chemie International Edition 53(30), pp. 7751-7755. (10.1002/anie.201404436)
- Emer, E. et al. 2014. Diversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(diazo-2,2,2-trifluoroethyl)arenes.. Organic Letters 16(22), pp. 6004-6007. (10.1021/ol5030184)
- O'Brien, E. R. et al. 2014. Glial activation in the early stages of brain metastasis: TSPO as a diagnostic biomarker.. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 5(2), pp. 275-280. (10.2967/jnumed.113.127449)
- Anthony, D. C. et al. 2014. Anti-CD20 inhibits T cell-mediated pathology and microgliosis in the rat brain.. Annals of Clinical and Translational Neurology 1(9), pp. 659-669. (10.1002/acn3.94)
- Hueting, R. et al. 2014. A comparison of the behavior of (64)Cu-acetate and (64)Cu-ATSM in vitro and in vivo.. Journal of nuclear medicine : official publication, Society of Nuclear Medicine 55(1), pp. 128-134. (10.2967/jnumed.113.119917)
- Huiban, M. et al. 2013. A broadly applicable [18F]trifluoromethylation of aryl and heteroaryl iodides for PET imaging. Nature Chemistry 5(11), pp. 941-944. (10.1038/nchem.1756)
- Benedetto, E., Tredwell, M., Hollingworth, C., Khotavivattana, T., Brown, J. M. and Gouverneur, V. 2013. Regio- and stereoretentive synthesis of branched, linear (E)- and (Z)-allyl fluorides from allyl carbonates under Ir-catalysis. Chem. Sci. 4(1), pp. 89-96. (10.1039/c2sc21789a)
- Mizuta, S. et al. 2013. Catalytic decarboxylative fluorination for the synthesis of tri- and difluoromethyl arenes.. Organic Letters 15(11), pp. 2648-2651. (10.1021/ol4009377)
- Benedetto, E., Keita, M., Tredwell, M., Hollingworth, C., Brown, J. M. and Gouverneur, V. 2012. Platinum-catalyzed substitution of allylic fluorides. Organometallics 31(4), pp. 1408-1416. (10.1021/om201029m)
- Gao, Z. et al. 2012. Metal-free oxidative fluorination of phenols with [18F]fluoride. Angewandte Chemie International Edition 51(27), pp. 6733-6737. (10.1002/anie.201201502)
- Tredwell, M. and Gouverneur, V. 2012. 18F labeling of arenes. Angewandte Chemie International Edition 51(46), pp. 11426-11437. (10.1002/anie.201204687)
- Hollingworth, C. et al. 2011. Palladium-catalyzed allylic fluorination. Angewandte Chemie International Edition 50(11), pp. 2613-2617. (10.1002/anie.201007307)
- Kersemans, V. et al. 2011. Hypoxia imaging using PET and SPECT: the effects of anesthetic and carrier gas on [Cu]-ATSM, [Tc]-HL91 and [F]-FMISO tumor hypoxia accumulation.. PLoS One 6(11), article number: e25911. (10.1371/journal.pone.0025911)
- Tredwell, M. J., Gulias, M., Gaunt Bremeyer, N., Johansson, C. C. C., Collins, B. S. L. and Gaunt, M. J. 2010. Palladium(II)-catalyzed C-H bond arylation of electron-deficient arenes at room temperature. Angewandte Chemie International Edition 50(5), pp. 1076-1079. (10.1002/anie.201005990)
- Tredwell, M., Luft, J. A. R., Schuler, M., Tenza, K., Houk, K. N. and Gouverneur, V. 2008. Fluorine-directed diastereoselective iodocyclizations. Angewandte Chemie International Edition 47(2), pp. 357-360. (10.1002/anie.200703465)
- Kostov, G., Tredwell, M., Gouverneur, V. and Ameduri, B. 2007. Kinetics of radical copolymerization of [1-(fluoromethyl)vinyl]benzene with chlorotrifluoroethylene. Journal of Polymer Science Part A: Polymer Chemistry 45(17), pp. 3843-3850. (10.1002/pola.22134)
- Teare, H., Huguet, F., Tredwell, M., Thibaudeau, S., Luthra, S. and Gouveneur, V. 2007. A convergent approach for the synthesis of fluorinated sphingosine analogues. Archive for Organic Chemistry 2007(10), pp. 232-244. (10.3998/ark.5550190.0008.a14)
- Sawicki, M., Kwok, A., Tredwell, M. and Gouverneur, V. 2007. Single and double stereoselective fluorination of (E)-allylsilanes. Beilstein Journal of Organic Chemistry 3(1), pp. 34. (10.1186/1860-5397-3-34)
- Tredwell, M. and Gouverneur, V. 2006. Electrophilic fluorination of organosilanes. Org. Biomol. Chem. 4(1), pp. 26-32. (10.1039/b513399h)
- Tredwell, M., Tenza, K., Pacheco, M. C. and Gouverneur, V. 2005. Synthesis of novel enantiopure fluorinated building blocks from acyclic chiral allylsilanes.. Organic Letters 7(20), pp. 4495-4497. (10.1021/ol0518535)
Book sections
- Tredwell, M. and Gouverneur, V. 2012. 1.5 fluorine in medicinal chemistry: importance of chirality. In: Comprehensive chirality., Vol. 1. Reference module in Chemistry, Molecular Sciences and Chemical Engineering London: Elsevier, pp. 70--85., (10.1016/b978-0-08-095167-6.00106-3)
Research
Research in the Tredwell Group has two main directions, organofluorine chemistry and fluorine-18 radiochemistry. We have fully equipped laboratories that allows us to perform both synthetic chemistry and radiochemistry in-house.
Fluorinated molecules have found widespread applications in agrochemistry, pharmaceuticals, through to fields such as materials science. Our research looks to develop novel methods for the selective and efficient synthesis of complex fluorinated compounds. Our current research programmes in this area includes
- Transition metal-catalysed synthesis of C-CF3 stereogenic centres
- Electrochemical fluorination
- Development of novel fluorinated motifs
Positron emission tomography (PET) imaging is a medicial imaging technique that is used both for clinical diagnosis of disease and to support drug discovery. This technique relies on the use of PET radiotracers, molecules containing positron-emitting radionuclides, designed to probe specific biochemical interactions. Fluorine-18 is positron-emitting radionuclide (t1/2 = 109.7 minutes) that is ideally suited for the radiolabelling of small molecules. Many of our synthetic chemistry programmes are intergrated in our radiochemistry research. Our current research in this area includes
- synthesis of 18F-perfluorinated motifs
- radiotracer development
- clinical translation of radiochemical technologies
For more information on specific projects available with Dr Matthew Tredwell please review the Molecular synthesis section of our research project themes.
Biography
- Senior Lecturer in Medicinal Chemistry 2023-current
- Senior Research Fellow, Cardiff University, 2023-current
- Lecturer in Medicinal Chemistry 2020-2023
- Research Fellow, Cardiff University, 2019-2023
Professional memberships
Member of Royal Society of Chemistry (MRSC)
Chartered Chemist (CChem)
Academic positions
- Group Leader, Max-Planck-Institut für Kohlenforschung, 2015-2019
- Postdoctoral Researcher, University of Oxford, 2009-2015
- Postdoctoral Researcher, University of Cambridge, 2007-2009
- DPhil, University of Oxford, 2003-2007
- MChem University of Oxford, 1999-2003
Supervisions
Radiochemistry
Organic chemistry
Radiotracer design
Medicinal chemistry
Contact Details
Research themes
Specialisms
- Organic chemical synthesis
- Biomedical imaging
- Medicinal and biomolecular chemistry
- radiochemistry