Imperial College London

Dr Matthew J. Fuchter

Faculty of Natural SciencesDepartment of Chemistry

Reader in Chemistry
 
 
 
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Contact

 

+44 (0)20 7594 5815m.fuchter

 
 
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Location

 

739ChemistrySouth Kensington Campus

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Summary

 

Publications

Publication Type
Year
to

96 results found

Montgomery KS, Davidson RWM, Cao B, Williams B, Simpson GW, Nilsson SK, Chiefari J, Fuchter MJet al., 2018, Effective macrophage delivery using RAFT copolymer derived nanoparticles, POLYMER CHEMISTRY, Vol: 9, Pages: 131-137, ISSN: 1759-9954

JOURNAL ARTICLE

Rice B, LeBlanc LM, Otero-de-la-Roza A, Fuchter MJ, Johnson ER, Nelson J, Jelfs KEet al., 2018, A computational exploration of the crystal energy and charge-carrier mobility landscapes of the chiral [6]helicene molecule., Nanoscale

The potential of a given π-conjugated organic molecule in an organic semiconductor device is highly dependent on molecular packing, as it strongly influences the charge-carrier mobility of the material. Such solid-state packing is sensitive to subtle differences in their intermolecular interactions and is challenging to predict. Chirality of the organic molecule adds an additional element of complexity to intuitive packing prediction. Here we use crystal structure prediction to explore the lattice-energy landscape of a potential chiral organic semiconductor, [6]helicene. We reproduce the experimentally observed enantiopure crystal structure and explain the absence of an experimentally observed racemate structure. By exploring how the hole and electron-mobility varies across the energy-structure-function landscape for [6]helicene, we find that an energetically favourable and frequently occurring packing motif is particularly promising for electron-mobility, with a highest calculated mobility of 2.9 cm2 V-1 s-1 (assuming a reorganization energy of 0.46 eV). We also calculate relatively high hole-mobility in some structures, with a highest calculated mobility of 2.0 cm2 V-1 s-1 found for chains of helicenes packed in a herringbone fashion. Neither the energetically favourable nor high charge-carrier mobility packing motifs are intuitively obvious, and this demonstrates the utility of our approach to computationally explore the energy-structure-function landscape for organic semiconductors. Our work demonstrates a route for the use of computational simulations to aid in the design of new molecules for organic electronics, through the a priori prediction of their likely solid-state form and properties.

JOURNAL ARTICLE

Brandt JR, Pospisil L, Bednarova L, da Costa RC, White AJP, Mori T, Teply F, Fuchter MJet al., 2017, Intense redox-driven chiroptical switching with a 580 mV hysteresis actuated through reversible dimerization of an azoniahelicene, CHEMICAL COMMUNICATIONS, Vol: 53, Pages: 9059-9062, ISSN: 1359-7345

JOURNAL ARTICLE

Brandt JR, Salerno F, Fuchter MJ, 2017, The added value of small-molecule chirality in technological applications, NATURE REVIEWS CHEMISTRY, Vol: 1, ISSN: 2397-3358

JOURNAL ARTICLE

Calbo J, Weston CE, White AJP, Rzepa HS, Contreras-Garcia J, Fuchter MJet al., 2017, Tuning Azoheteroarene Photoswitch Performance through Heteroaryl Design, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Vol: 139, Pages: 1261-1274, ISSN: 0002-7863

JOURNAL ARTICLE

Hazel P, Kroll SHB, Bondke A, Barbazanges M, Patel H, Fuchter MJ, Coombes RC, Ali S, Barrett AGM, Freemont PSet al., 2017, Inhibitor Selectivity for Cyclin-Dependent Kinase7: AStructural, Thermodynamic, and Modelling Study, CHEMMEDCHEM, Vol: 12, Pages: 372-380, ISSN: 1860-7179

JOURNAL ARTICLE

Scott DJ, Fuchter MJ, Ashley AE, 2017, Designing effective 'frustrated Lewis pair' hydrogenation catalysts, CHEMICAL SOCIETY REVIEWS, Vol: 46, Pages: 5689-5700, ISSN: 0306-0012

JOURNAL ARTICLE

Sundriyal S, Chen PB, Lubin AS, Lueg GA, Li F, White AJP, Malmquist NA, Vedadi M, Scherf A, Fuchter MJet al., 2017, Histone lysine methyltransferase structure activity relationships that allow for segregation of G9a inhibition and anti-Plasmodium activity, MEDCHEMCOMM, Vol: 8, Pages: 1069-1092, ISSN: 2040-2503

JOURNAL ARTICLE

Sundriyal S, Moniot S, Mahmud Z, Yao S, Di Fruscia P, Reynolds CR, Dexter DT, Sternberg MJ, Lam EW, Steegborn C, Fuchter MJet al., 2017, Thienopyrimidinone based sirtuin-2 (SIRT2)-selective inhibitors bind in the ligand induced 'selectivity pocket'., Journal of Medicinal Chemistry, Vol: 60, Pages: 1928-1945, ISSN: 0022-2623

Sirtuins (SIRTs) are NAD-dependent deacylases, known to be involved in a variety of pathophysiological processes and thus remain promising therapeutic targets for further validation. Previously, we reported a novel thienopyrimidinone SIRT2 inhibitor with good potency and excellent selectivity for SIRT2. Herein, we report an extensive SAR study of this chemical series and identify the key pharmacophoric elements and physiochemical properties that underpin the excellent activity observed. New analogues have been identified with submicromolar SIRT2 inhibtory activity and good to excellent SIRT2 subtype-selectivity. Importantly, we report a co-crystal structure of one of our compounds (29c) bound to SIRT2. This reveals our series to induce the formation of a previously reported 'selectivity pocket', but to bind in an inverted fashion to what might be intuitively expected. We believe these findings will contribute significantly to understanding of the mechanism of action of SIRT2 inhibitors and to the identification of refined, second generation inhibitors.

JOURNAL ARTICLE

Sundriyal S, Moniot S, Mahmud Z, Yao S, Di Fruscia P, Reynolds CR, Dexter DT, Sternberg MJE, Lam EW-F, Steegborn C, Fuchter MJet al., 2017, Thienopyrimidinone Based Sirtuin-2 (SIRT2)-Selective Inhibitors Bind in the Ligand Induced Selectivity Pocket, JOURNAL OF MEDICINAL CHEMISTRY, Vol: 60, Pages: 1928-1945, ISSN: 0022-2623

JOURNAL ARTICLE

Weston CE, Kraemer A, Colin F, Yildiz O, Baud MGJ, Meyer-Almes F-J, Fuchter MJet al., 2017, Toward Photopharmacological Antimicrobial Chemotherapy Using Photoswitchable Amidohydrolase Inhibitors, ACS INFECTIOUS DISEASES, Vol: 3, Pages: 152-161, ISSN: 2373-8227

JOURNAL ARTICLE

Weston CE, Krämer A, Colin F, Yildiz Ö, Baud MGJ, Meyer-Almes F-J, Fuchter MJet al., 2017, Toward Photopharmacological Antimicrobial Chemotherapy Using Photoswitchable Amidohydrolase Inhibitors., ACS Infect Dis, Vol: 3, Pages: 152-161

Photopharmacological agents exhibit light-dependent biological activity and may have potential in the development of new antimicrobial agents/modalities. Amidohydrolase enzymes homologous to the well-known human histone deacetylases (HDACs) are present in bacteria, including resistant organisms responsible for a significant number of hospital-acquired infections and deaths. We report photopharmacological inhibitors of these enzymes, using two classes of photoswitches embedded in the inhibitor pharmacophore: azobenzenes and arylazopyrazoles. Although both classes of inhibitor show excellent inhibitory activity (nM IC50 values) of the target enzymes and promising differential activity of the switchable E- and Z-isomeric forms, the arylazopyrazoles exhibit better intrinsic photoswitch performance (more complete switching, longer thermal lifetime of the Z-isomer). We also report protein-ligand crystal structures of the E-isomers of both an azobenzene and an arylazopyrazole inhibitor, bound to bacterial histone deacetylase-like amidohydrolases (HDAHs). These structures not only uncover interactions important for inhibitor binding but also reveal conformational differences between the two photoswitch inhibitor classes. As such, our data may pave the way for the design of improved photopharmacological agents targeting the HDAC superfamily.

JOURNAL ARTICLE

Yang Y, Rice B, Shi X, Brandt JR, Correa da Costa R, Hedley GJ, Smilgies D-M, Frost JM, Samuel IDW, Otero-de-la-Roza A, Johnson ER, Jelfs KE, Nelson J, Campbell AJ, Fuchter MJet al., 2017, Emergent Properties of an Organic Semiconductor Driven by its Molecular Chirality, ACS Nano, Vol: 11, Pages: 8329-8338, ISSN: 1936-0851

Chiral molecules exist as pairs of nonsuperimposable mirror images; a fundamental symmetry property vastly underexplored in organic electronic devices. Here, we show that organic field-effect transistors (OFETs) made from the helically chiral molecule 1-aza[6]helicene can display up to an 80-fold difference in hole mobility, together with differences in thin-film photophysics and morphology, solely depending on whether a single handedness or a 1:1 mixture of left- and right-handed molecules is employed under analogous fabrication conditions. As the molecular properties of either mirror image isomer are identical, these changes must be a result of the different bulk packing induced by chiral composition. Such underlying structures are investigated using crystal structure prediction, a computational methodology rarely applied to molecular materials, and linked to the difference in charge transport. These results illustrate that chirality may be used as a key tuning parameter in future device applications.

JOURNAL ARTICLE

Ali S, Patel H, Periyasamy M, Bondke A, Slafer BW, Ottaviani S, Harrod A, Buluwela L, Fuchter MJ, Barrett AGM, Coombes RCet al., 2016, ICEC0942, an orally bioavailable selective inhibitor of CDK7 for breast cancer, UK Breast Cancer Research Symposium, Publisher: SPRINGER, Pages: 195-195, ISSN: 0167-6806

CONFERENCE PAPER

Brandt JR, Wang X, Yang Y, Campbell AJ, Fuchter MJet al., 2016, Circularly Polarized Phosphorescent Electroluminescence with a High Dissymmetry Factor from PHOLEDs Based on a Platinahelicene, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Vol: 138, Pages: 9743-9746, ISSN: 0002-7863

JOURNAL ARTICLE

Chen PB, Ding S, Zanghi G, Soulard V, DiMaggio PA, Fuchter MJ, Mecheri S, Mazier D, Scherf A, Malmquist NAet al., 2016, Plasmodium falciparum PfSET7: enzymatic characterization and cellular localization of a novel protein methyltransferase in sporozoite, liver and erythrocytic stage parasites, SCIENTIFIC REPORTS, Vol: 6, ISSN: 2045-2322

JOURNAL ARTICLE

Davidson RWM, Fuchter MJ, 2016, Direct NHC-catalysed redox amidation using CO2 for traceless masking of amine nucleophiles, CHEMICAL COMMUNICATIONS, Vol: 52, Pages: 11638-11641, ISSN: 1359-7345

JOURNAL ARTICLE

Scott DJ, Phillips NA, Sapsford JS, Deacy AC, Fuchter MJ, Ashley AEet al., 2016, Versatile Catalytic Hydrogenation Using A Simple Tin(IV) Lewis Acid, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, Vol: 55, Pages: 14738-14742, ISSN: 1433-7851

JOURNAL ARTICLE

Weston CE, Richardson RD, Fuchter MJ, 2016, Photoswitchable basicity through the use of azoheteroarenes, CHEMICAL COMMUNICATIONS, Vol: 52, Pages: 4521-4524, ISSN: 1359-7345

JOURNAL ARTICLE

Weston CE, Richardson RD, Haycock PR, White AJP, Fuchter MJet al., 2016, "Arylazopyrazoles: Azoheteroarene Photoswitches Offering Quantitative Isomerization and Long Thermal Half-Lives (vol 136, pg 11878, 2014), JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Vol: 138, Pages: 10716-10716, ISSN: 0002-7863

JOURNAL ARTICLE

Anwar A, Archibald S, Audisio D, Badman G, Bergin J, Bew SP, Bloom J, Bushby N, Busigin A, Chan MY, Davies J, Dilworth J, Dunscombe M, Elmore CS, Engstrom P, Fuchter MJ, Geach NJ, Georgin D, Griffiths A, Hansen P, Hardcastle G, Hiatt-Gipson GD, Hickey MJ, Kitson SL, Lashford A, Lenz E, Lewinton S, Lockley WJ, Loreau O, Maddocks S, Marlière P, McEwen A, Moody TS, Morgan P, Roe SJ, Schenk DJ, Speed DJ, Stockman RA, Sumal K, Taran F, Thurston S, Waring M, Watters WHet al., 2015, Abstracts., J Labelled Comp Radiopharm, Vol: 58, Pages: 147-155

JOURNAL ARTICLE

Bultinck P, Cherblanc FL, Fuchter MJ, Herrebout WA, Lo Y-P, Rzepa HS, Siligardi G, Weimar Met al., 2015, Chiroptical Studies on Brevianamide B: Vibrational and Electronic Circular Dichroism Confronted, JOURNAL OF ORGANIC CHEMISTRY, Vol: 80, Pages: 3359-3367, ISSN: 0022-3263

JOURNAL ARTICLE

Curry E, Green I, Chapman-Rothe N, Shamsaei E, Kandil S, Cherblanc FL, Payne L, Bell E, Ganesh T, Srimongkolpithak N, Caron J, Li F, Uren AG, Snyder JP, Vedadi M, Fuchter MJ, Brown Ret al., 2015, Dual EZH2 and EHMT2 histone methyltransferase inhibition increases biological efficacy in breast cancer cells, CLINICAL EPIGENETICS, Vol: 7, ISSN: 1868-7083

JOURNAL ARTICLE

Di Fruscia P, Zacharioudakis E, Liu C, Moniot S, Laohasinnarong S, Khongkow M, Harrison IF, Koltsida K, Reynolds CR, Schmidtkunz K, Jung M, Chapman KL, Steegborn C, Dexter DT, Sternberg MJE, Lam EW-F, Fuchter MJet al., 2015, The Discovery of a Highly Selective 5,6,7,8-Tetrahydrobenzo[4,5]thieno[ 2,3-d] pyrimidin-4(3H)-one SIRT2 Inhibitor that is Neuroprotective in an in vitro Parkinson's Disease Model, CHEMMEDCHEM, Vol: 10, Pages: 69-82, ISSN: 1860-7179

JOURNAL ARTICLE

Fuchter MJ, 2015, Young Career Focus: Dr. Matthew J. Fuchter (Imperial College London, UK), SYNTHESIS-STUTTGART, Vol: 47, Pages: A152-A155, ISSN: 0039-7881

JOURNAL ARTICLE

Fuchter MJ, 2015, Carbon-14 reprocessing at cardiff, Publisher: WILEY-BLACKWELL, Pages: 149-150, ISSN: 0362-4803

CONFERENCE PAPER

Malmquist NA, Sundriyal S, Caron J, Chen P, Witkowski B, Menard D, Suwanarusk R, Renia L, Nosten F, Belen Jimenez-Diaz M, Angulo-Barturen I, Santos Maritnez M, Ferrer S, Sanz LM, Gamo F-J, Wittlin S, Duffy S, Avery VM, Ruecker A, Delves MJ, Sinden RE, Fuchter MJ, Scherf Aet al., 2015, Histone Methyltransferase Inhibitors Are Orally Bioavailable, Fast-Acting Molecules with Activity against Different Species Causing Malaria in Humans, ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, Vol: 59, Pages: 950-959, ISSN: 0066-4804

JOURNAL ARTICLE

Richardson RD, Baud MGJ, Weston CE, Rzepa HS, Kuimova MK, Fuchter MJet al., 2015, Dual wavelength asymmetric photochemical synthesis with circularly polarized light, CHEMICAL SCIENCE, Vol: 6, Pages: 3853-3862, ISSN: 2041-6520

JOURNAL ARTICLE

Scott DJ, Simmons TR, Lawrence EJ, Wildgoose GG, Fuchter MJ, Ashley AEet al., 2015, Facile Protocol for Water-Tolerant "Frustrated Lewis Pair"-Catalyzed Hydrogenation, ACS CATALYSIS, Vol: 5, Pages: 5540-5544, ISSN: 2155-5435

JOURNAL ARTICLE

Udemba A, Smith G, Nguyen Q-D, Kaliszczak M, Carroll L, Fortt R, Fuchter MJ, Aboagye EOet al., 2015, Design, synthesis and initial characterisation of a radiolabelled [F-18]pyrimidoindolone probe for detecting activated caspase-3/7, ORGANIC & BIOMOLECULAR CHEMISTRY, Vol: 13, Pages: 5418-5423, ISSN: 1477-0520

JOURNAL ARTICLE

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