Mike Edwards

Biography

I was appointed as a lecturer at Keele in the summer of 2011. I obtained first my undergraduate degree (MChem) from the University of Bath undertaking a final year project, synthesising anti-malarial agents, under the supervision of Prof. Malcolm Sainsbury. Having loved my 4 years in Bath I stayed to complete a PhD working with Prof. Jon Williams. My research pioneered a new approach to C-C bond formation using alcohols as alkylating agents and transition metal catalysis to “borrow hydrogen” – this remains an area of worldwide research interest today.

Following this I undertook two postdoctoral research stints, first at the University of Illinois Urbana−Champaign (USA) working with Prof. Scott Denmark in the area of Lewis base catalysis and organoelement chemistry, and more recently with Prof Richard Taylor at the University of York working on the synthesis of natural products and biologically relevant heterocycles.

Research and scholarship

Scholarship
I’m interested in the following areas of chemical education and curriculum development:

(a) Student understanding and learning of organic reaction mechanisms
(b) Development of a modern medicinal chemistry curriculum
(c) The use of technology and digital resources to improve student engagement
(c) Transnational degree programs in chemistry

Research
Our research is targeted in the broad area of heterocycle synthesis and its application to medicinal chemistry. We aim to develop new and efficient methods to prepare interesting molecules and apply them to interesting problems, particularly as molecular probes. The current projects are of particular interest:

(a) Targeted Autotaxin inhibitors as a therapy for Ovarian Cancer (in collaboration with Alan Richardson and Steve Allin)

Ovarian tumours represent a challenging drug target, many of the best chemotherapies displaying poor pharmacokinetic properties and undergoing extensive in vivo metabolism. We are examining methods for the effective treatment of such tumours by delivering inhibitors which target autotaxin (ATX), an enzyme which plays an important role in the proliferation of ovarian tumours. We have recently reported two studies using PAMAM (a common dendrimer) to deliver S32826, 1a; and icodextrin (a common polysaccharide used in dialysis) as a vehicle to deliver HA–155, 1b.

(b) Novel Anti-malarial agents (in collaboration with Tess Phillips, Paul Horrocks and Steve Allin)

We are investigating the synthesis and evaluation of alkaloids based on a series of heterocyclic templates e.g. 2 which possess anti-malarial activity via novel mechanisms of action.

The organoselenium heterocycle ebselen 3 is a mimic of the enzyme Glutathione Peroxidase (GPx), a key element in the body’s defence against reactive oxygen species (ROS) and oxidants. It has been investigated in phase III clinical trials for the treatment of reperfusion injury, but despite showing excellent in vitro activity it has limited in vivo activity. We are interested in the evaluation of alternative GPx mimetics based on selenium(IV) derivatives e.g. 4 which have an alternative mechanism of action.

Teaching

I teach on the Chemistry and Medicinal Chemistry degree programmes in the following modules:

CHE-10061: Practical and Professional Chemistry Skills
CHE-10063: Chemical Structure and Reactivity
CHE-20027: Medicinal and Biological Chemistry 1
CHE-20055: Molecular Chemistry and Reactions
CHE-30037: Topics in Chemistry (Module Leader)
CHE-30039: Advanced Organic Chemistry
CHE-30044: Topics in Medicinal Chemistry (Module Leader)
CHE-30046: Synoptic Topics in Chemistry (Module Leader)
CHE-30047: Medicinal and Biological Chemistry 2
CHE-30050: Chemistry/Medicinal Chemistry Research Project
CHE-30051: Chemistry/Medicinal Chemistry Dissertation
CHE-40021: MChem Research Project
CHE-40023: Applied Chemistry Topics

Selected Publications

Cranwell PB, Edwards MG, Haxton KJ, Hyde J, Page EM, Plana D, Sedhi G, Wright JS. Chinese Students’ Expectations Versus Reality When Studying on a UK-China Transnational Chemistry Degree Program. New Directions in the Teaching of Physical Sciences. doi> link> full text>
Fisher N, Edwards MG, Hemming R, Allin SM, Wallis JD, Bulman Page PC, Mckenzie MJ, Jones SM, Elsegood MRJ, King-Underwood J, Richardson A. 2018. Synthesis and Activity of a Novel Autotaxin Inhibitor-Icodextrin Conjugate. J Med Chem. link> doi> full text>
Hancock LM, Edwards MG, Jones GR, O'Brien M. 2017. Cram's Rule: Diastereoselective Grignard addition to 2-phenylpropanal. In Comprehensive Organic Chemistry Experiments for the Laboratory Classroom. Alfonso CAM, Candeias NR, Simao DP, Trindade AF, Coelho JAS, Tan B, Franzen R (Eds.). Royal Society of Chemistry.
Fisher N, Hilton-Bolt T, Edwards MG, Haxton KJ, McKenzie M, Allin SM, Richardson A. 2014. Dendrimer Conjugate of [4-(Tetradecanoylamino)benzyl]phosphonic Acid (S32826) as an Autotaxin Inhibitor. ACS Med Chem Lett, 34-39, vol. 5(1). link> doi>
Bastin R, Dale JW, Edwards MG, Papillon JPN, Webb MR, Taylor RJK. 2011. Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route. TETRAHEDRON, 10026-10044, vol. 67(51). link> doi>

Full Publications Listshow

Journal Articles

Cranwell PB, Edwards MG, Haxton KJ, Hyde J, Page EM, Plana D, Sedhi G, Wright JS. Chinese Students’ Expectations Versus Reality When Studying on a UK-China Transnational Chemistry Degree Program. New Directions in the Teaching of Physical Sciences. doi> link> full text>
Fisher N, Edwards MG, Hemming R, Allin SM, Wallis JD, Bulman Page PC, Mckenzie MJ, Jones SM, Elsegood MRJ, King-Underwood J, Richardson A. 2018. Synthesis and Activity of a Novel Autotaxin Inhibitor-Icodextrin Conjugate. J Med Chem. link> doi> full text>
Fisher N, Hilton-Bolt T, Edwards MG, Haxton KJ, McKenzie M, Allin SM, Richardson A. 2014. Dendrimer Conjugate of [4-(Tetradecanoylamino)benzyl]phosphonic Acid (S32826) as an Autotaxin Inhibitor. ACS Med Chem Lett, 34-39, vol. 5(1). link> doi>
Bastin R, Dale JW, Edwards MG, Papillon JPN, Webb MR, Taylor RJK. 2011. Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route. TETRAHEDRON, 10026-10044, vol. 67(51). link> doi>
Beltran-Rodil S, Edwards MG, Pugh DS, Reid M, Taylor RJK. 2010. The Preparation of Substituted Pyrazoles from beta,beta-Dibromo-enones by a Tandem Condensation/Suzuki-Miyaura Cross-Coupling Process. SYNLETT, 602-606. link> doi>
Catozzi N, Edwards MG, Raw SA, Wasnaire P, Taylor RJK. 2009. Synthesis of the louisianin alkaloid family via a 1,2,4-triazine inverse-electron-demand Diels-Alder approach. J Org Chem, 8343-8354, vol. 74(21). link> doi>
Beltran-Rodil S, Donald JR, Edwards MG, Raw SA, Taylor RJK. 2009. Tandem retro-aldol/Wittig/Michael and related cascade processes. TETRAHEDRON LETTERS, 3378-3380, vol. 50(26). link> doi>
Edwards MG, Pugh DS, Whitwood AC, Taylor RJK. 2009. gem-Dimethylcyclopropanation of dibenzylideneacetone using triisopropyl sulfoxonium tetrafluoroborate. Acta Crystallogr C, o39-o41, vol. 65(Pt 2). link> doi>
Edwards MG, Kenworthy MN, Kitson RRA, Perry A, Scott MS, Whitwood AC, Taylor RJK. 2008. The preparation of alpha-alkylidene-gamma-butyrolactones using a telescoped intramolecular Michael/olefination (TIMO) sequence: Synthesis of (+)-paeonilactone B. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 4769-4783, vol. 2008(28). link> doi>
Edwards MG, Paxton RJ, Pugh DS, Whitwood AC, Taylor RJK. 2008. gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations. SYNTHESIS-STUTTGART, 3279-3288. link> doi>
Edwards MG, Paxton RJ, Pugh DS, Taylor RJK. 2008. An improved gem-dimethylcyclopropanation procedure using triisopropylsulfoxonium tetrafluoroborate. SYNLETT, 521-524. link> doi>
Edwards MG, Kenworthy MN, Kitson RRA, Scott MS, Taylor RJK. 2008. The telescoped intramolecular michael/olefination (TIMO) approach to alpha-alkylidene-gamma-butyrolactones: synthesis of (+)-paeonilactone B. Angew Chem Int Ed Engl, 1935-1937, vol. 47(10). link> doi>
Barfoot CW, Burns AR, Edwards MG, Kenworthy MN, Ahmed M, Shanahan SE, Taylor RJK. 2008. A convergent synthesis of the tricyclic core of the dictyosphaeric acids. Org Lett, 353-356, vol. 10(2). link> doi>
Donald JR, Edwards MG, Taylor RJK. 2007. Tandem oxime formation - epoxide ring opening sequences for the preparation of oxazines related to the trichodermamides. TETRAHEDRON LETTERS, 5201-5204, vol. 48(30). link> doi>
Black PJ, Edwards MG, Williams JMJ. 2006. Borrowing hydrogen: Indirect "Wittig" olerination for the formation of C-C bonds from alcohols. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 4367-4378, vol. 2006(19). link> doi>
Denmark SE and Edwards MG. 2006. On the mechanism of the selenolactonization reaction with selenenyl halides. J Org Chem, 7293-7306, vol. 71(19). link> doi>
Black PJ, Cami-Kobeci G, Edwards MG, Slatford PA, Whittlesey MK, Williams JMJ. 2006. Borrowing hydrogen: iridium-catalysed reactions for the formation of C-C bonds from alcohols. Org Biomol Chem, 116-125, vol. 4(1). link> doi>
Black PJ, Edwards MG, Williams JMJ. 2005. Catalytic electronic activation as a tool for the addition of stabilised nucleophiles to allylic alcohols. TETRAHEDRON, 1363-1374, vol. 61(5). link> doi>
Edwards MG, Jazzar RFR, Paine BM, Shermer DJ, Whittlesey MK, Williams JMJ, Edney DD. 2004. Borrowing hydrogen: a catalytic route to C-C bond formation from alcohols. Chem Commun (Camb), 90-91. link> doi>
Adair GRA, Edwards MG, Williams JMJ. 2003. Triphenylphosphine-catalysed conversion of maleic anhydride into acrylate esters. TETRAHEDRON LETTERS, 5523-5525, vol. 44(29). link> doi>
Edwards MG and Williams JMJ. 2002. Catalytic electronic activation: indirect "Wittig" reaction of alcohols. Angew Chem Int Ed Engl, 4740-4743, vol. 41(24). link> doi>
Edwards MG, Phillips TR, Horrocks PD, Tunstall LV, Allin SMA. FORTHCOMING: Preparation and Anti-malarial activity of 2-Aminobenzimidazoles. TBC.
Phillips TR, Edwards MG, Horrocks PD, Allin SM, Tunstall LV. FORTHCOMING: Spiroindolines paper (title to be confirmed).
Fisher N, Edwards MG, Allin SM, McKenzie MJ, Jones SM, Elsegood MRJ, King-Underwood J, Richardson A. FORTHCOMING: Synthesis and Activity of a Novel Autotaxin Inhibitor-Icodextrin Conjugate.
Fisher N, Edwards MG, Allin SM, McKenzie MJ, Jones SM, Elsegood MRJ, King-Underwood J, Richardson A. FORTHCOMING: Synthesis and Activity of a Novel Autotaxin Inhibitor-Icodextrin Conjugate.
Phillips TR, Edwards MG, Horrocks P, Tunstall LV, Allin S. FORTHCOMING: Tetrahydro-beta-carbolines paper (title to be confirmed).

Chapters

Hancock LM, Edwards MG, Jones GR, O'Brien M. 2017. Cram's Rule: Diastereoselective Grignard addition to 2-phenylpropanal. In Comprehensive Organic Chemistry Experiments for the Laboratory Classroom. Alfonso CAM, Candeias NR, Simao DP, Trindade AF, Coelho JAS, Tan B, Franzen R (Eds.). Royal Society of Chemistry.

School address

Lennard-Jones School of Chemical and Physical Sciences
Lennard-Jones Building
Keele University
Staffordshire
ST5 5BG, UK
Phone: +44 (0)1782 734921 (School Office)
Email: chemistry@keele.ac.uk, forensics@keele.ac.uk, physics@keele.ac.uk

Programme directors

Chemistry and Medicinal Chemistry
Dr Matthew O'Brien
Tel : +44 (0)1782 734371
Email : m.obrien@keele.ac.uk

Forensic Science
Dr Richard Darton
Tel : +44 (0)1782 733345
Email : r.j.darton@keele.ac.uk

Physics and Astrophysics
Dr Arumugam Mahendrasingam
Tel : +44 (0)1782 733312
Email : a.mahendrasingam@keele.ac.uk

Admission tutors

Chemistry and Medicinal Chemistry
Dr Natalie Capel
Tel : +44 (0)1782 733584
Email : n.j.capel@keele.ac.uk

Forensic Science
Victoria Cartwright
Tel : +44 (0)1782 733584
Email : v.cartwright@keele.ac.uk

Physics and Astrophysics
Dr Patrick Connell
Tel : +44 (0)1782 733892
Email : physics@keele.ac.uk or p.j.connell@keele.ac.uk

Dr Mike Edwards