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Dr Alison Edwards

Senior Lecturer in Pharmaceutical Chemistry

Medway School of Pharmacy

 

Alison obtained her BSc (Hons) in Chemistry from the University of Dundee in 1999 and received her DPhil from the University of Oxford in 2003. Prior to appointment at the Medway School of Pharmacy in November 2006, she held a postdoctoral researcher position at Imperial College London. Her early research focused on the synthesis and conformational study of sugar derived peptidomimetics (commonly known as sugar amino acids) and has published numerous papers in this area since 2003. Her current research interests include the use of chiroptical spectroscopy, the conformational preference of novel foldamer systems and the preparation of supramolecular hydrogels using carbohydrate scaffolds.

She is currently module convener for the science elective Advanced Therapeutic Agents (4th year, MPharm). She teaches a range of topics including 'Carbohydrates as drugs'; spectroscopy; organic, physical and general chemistry.

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Alison’s early research background employed carbohydrate and peptide synthetic methods to prepare novel molecules such as sugar amino acids. These molecules have since been utilized as highly functionalized stereodiverse molecular scaffolds for a range of applications such as compound libraries and for hydrogel materials. In parallel to this, she has a keen interest in understanding the conformational preference of novel systems which have the propensity to fold into specific conformations (foldamers). This has led to the extensive utilization of circular dichroism, combined with other techniques, to explore the conformational space sampled by novel peptidomimetic foldamers. These systems offer therapeutic advantages such as improved bioavailability, specificity and ability to penetrate into cells. In addition to peptide mimicry, such foldamer systems may also be employed to mimic oligosaccharides, DNA and RNA. 

With this in mind, areas of interest are:
  • The development of new biomaterials such as hydrogels for pharmaceutical and food applications.
  • The use of carbohydrates in multidisciplinary fields of chemistry and biology with emphasis on their exploitation as highly functionalised stereodiverse molecular scaffolds.
  • The study of hybrid peptide-carbohydrate systems, in particular to establish conformational preference and to investigate molecular interaction e.g. with probe molecules.
  • Developing new insight into the conformational understanding of biopolymer systems.
  • Utilization of chiroptical spectroscopies, such as circular dichroism, for exploration of molecular interactions and the conformational study of biopolymer systems.
  • The interplay between molecular self-assembly, molecular structure and conformation.
  • Utilization of small molecular weight carbohydrates for the preparation of novel drug candidates.

Keywords: carbohydrate/peptide synthesis; secondary structure; conformational investigation; circular dichroism; supramolecular hydrogels; materials.

Current Projects

Research currently focuses in three main areas:

The study of novel foldamer systems.

Peptidomimetic foldamers have been prepared (in collaboration with groups in UK, France and Denmark) which have been studied for secondary structural preference. Expertise has evolved in the use of circular dichroism to explore secondary structural preference of novel backbones and to utilise a combined approach with other techniques such as NMR, IR, X-ray and VOA to ascertain the maximum understanding of conformational preference. Recent collaboration will also include the use of molecular dynamics to gain improved understanding of systems which have intrinsic flexibility. A range of different foldamer systems have been studied to date: carbopeptoids, α,β-peptoids and arylopeptoids.
Currently working on this project: Mrs Emiliana De Santis (PhD, 2008-2012) and Miss Soumya Sasi (PhD, 2011- ).

Collaborators: Prof. Taillefumier, Clermont-Ferrand, France. Dr Hjelmgaard, Copenhagen, Denmark. Dr Alexander, Greenwich, UK. Prof. Fleet, Oxford, UK. Dr Tranter, Chiralabs, UK.

current project fig 1.

Supramolecular hydrogels.

In recent years there has been increased interest in the use of hydrogels which arise from small molecular weight compounds utilising self-assembly mechanisms. A number of research groups are working on peptide-based gelators and exploit proteinogenic building blocks for a wide range of gelation triggers and applications e.g. cell culture. Our carbohydrate expertise lets us utilise the saccharide building blocks to prepare stereodiverse scaffolds from which small molecular weight hydrogelators can be prepared in short synthetic sequences by exploitation of peptide chemistry. Initial work in this area has identified aromatic carbohydrate amphiphiles which form hydrogels via a novel CH-π self assembly process. Reported in Chemical Science 2(7).

Collaborator: Prof. Ulijn, University of Strathclyde, Glasgow, UK

Currently working on this project: Dr Andrew Hall, Miss Carmen Piras (PhD, 2013-).

current project fig 2.

Targeting of chemotactic vasoactive peptide receptor signalling in neurovascular diseases

silica NP imageThe scope of the project is to synthesize novel hybrid silica-core-noble-metal shell based nanocarriers and investigate their capacity for the targeted delivery and controlled release of neuroactive peptides into malignant brain tumours. The nanocarriers will be evaluated by the collaborating research team at the University of Rouen, France to ascertain their efficiency of delivery in vitro and in vivo. Working closely with researchers at Rouen, the design of the nanocarriers is expected to be further optimised to enhance the delivery and the therapeutic effect.

 

This project forms part of the “Peptide Research Network of Excellence” (PeReNE) and is funded by the Interreg-IVA program France (Channel) - England. The purpose of PeReNE is to place the Channel region at the forefront of peptide research by bringing together efforts of 23 research teams and 3 core facilities from INSERM, CNRS and Universities of Amiens, Rouen, Caen, Rennes, Brest, Exeter, Southampton, Portsmouth, Brighton, Sussex and Kent.

Project Collaborator: Dr Helene Castel, Inserm U982, Institute of Research and Biomedical Innovation, University of Rouen, Rouen, France

Funding: Interreg-IVA program France (Channel) – England

Staff working on the project (Medway): Dr Vladimir Gubala, Dr Alison Edwards, Dr Matthew Freddi, Mr Mo Momin

News items for the project:  March 2013 - New researcher appointed at Medway for PeReNE project, October 2012 - European funding success for peptide researchers.

PeReNE logo interreg logo


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Selected publications

  • Wang S-H, Lin Y, Todorova N, Xu Y, Mazo M, Rana S, Leonardo V, Amdursky N, Spicer CD, Alexander BD, Edwards AA, Matthews SJ, Yarovsky I and Stevens MM (2017). Facet-Dependent Interactions of Islet Amyloid Polypeptide with Gold Nanoparticles: Implications for Fibril Formation and Peptide-Induced Lipid Membrane Disruption. Chemistry of Materials, 29(4): 1550–1560. DOI: 10.1021/acs.chemmater.6b04144
  • Giovannini G, Kunc F, Piras CC, Ondrej Stranik, Edwards AA, Hall AJ and Gubala V (2017).  Stabilizing silica nanoparticles in hydrogels: impact on storage and polydispersity. RSC Advances, 7: 19924-19933. DOI: 10.1039/C7RA02427D
  • De Santis E, Edwards AA, Alexander BD, Holder SJ, Biesse-Martin A-S, Nielsen BV, Mistry D, Waters L,  Siligardi G, Hussain R, Faure S and Taillefumier C (2016). Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer: a spectroscopic and computational study. Organic and Biomolecular Chemistry [Online]. Available at: http://doi.org/10.1039/C6OB01954D. Selected to be front cover of the issue. Available as open access.
  • Birchall LS, Roy S, Jayawarna V, Hughes M, Irvine E, Okorogheye GT, Saudi N, De Santis E, Tuttle T, Edwards AA, Ulijn RV (2011).  Exploiting CH-π interactions in supramolecular hydrogels of aromatic carbohydrate amphiphiles. Chemical Science 2(7): 1349-1355.  Selected to be on front cover of issue.
    http://pubs.rsc.org/en/content/articlelanding/2011/sc/c0sc00621a
  • Edwards AA, Fleet GWJ, Tranter GE (2006). Classification of conformation for sugar amino acid systems using chiroptical spectroscopy. Chirality 18: 265-272. http://onlinelibrary.wiley.com/doi/10.1002/chir.20248/abstract
  • Edwards AA, Ichihara O, Murfin S, Wilkes R, Whittaker M, Watkin DJ, Fleet GWJ (2004). Tetrahydrofuran-based amino acids as library scaffolds. Journal of Combinatorial Chemistry 6: 230-238.http://pubs.acs.org/doi/abs/10.1021/cc034054r

Book chapters

  • Edwards A, Jenkinson S (2012). “Perspective and Concepts: Overview of Techniques for Assigning Stereochemistry.” Volume 8, pp. 39-53. Comprehensive Chirality. Editors: Carreira E, Yamamoto, H. Elsevier, ISBN: 9780080951676
  • Edwards AA, Alexander BD (2010). “Organic Applications of UV-Visible Absorption Spectroscopy.” Volume 2, 2030-2039. Encyclopedia of Spectroscopy and Spectrometry, 2nd Edition. Editors: Lindon J, Tranter GE, Koppenaal D. ACADEMIC PRESS, ISBN 978-0-12-374417-3.
    book pic

Full publication history

  • Wang S-H, Lin Y, Todorova N, Xu Y, Mazo M, Rana S, Leonardo V, Amdursky N, Spicer CD, Alexander BD, Edwards AA, Matthews SJ, Yarovsky I and Stevens MM (2017). Facet-Dependent Interactions of Islet Amyloid Polypeptide with Gold Nanoparticles: Implications for Fibril Formation and Peptide-Induced Lipid Membrane Disruption. Chemistry of Materials, 29(4): 1550–1560. DOI: 10.1021/acs.chemmater.6b04144
  • Giovannini G, Kunc F, Piras CC, Ondrej Stranik, Edwards AA, Hall AJ and Gubala V (2017).  Stabilizing silica nanoparticles in hydrogels: impact on storage and polydispersity. RSC Advances, 7: 19924-19933. DOI: 10.1039/C7RA02427D
  • De Santis E, Edwards AA, Alexander BD, Holder SJ, Biesse-Martin A-S, Nielsen BV, Mistry D, Waters L,  Siligardi G, Hussain R, Faure S and Taillefumier C (2016). Selective complexation of divalent cations by a cyclic α,β-peptoid hexamer: a spectroscopic and computational study. Organic and Biomolecular Chemistry [Online]. Available at: http://doi.org/10.1039/C6OB01954D. Selected to be front cover of the issue. Available as open access.
  • Al-Hamidi H, Edwards AA, Douroumis D, Asare-Addo, K, Nayebi, AM, Reyhani-Rad S, Mahmoudi J, Nokhodchi A (2013).  Effect of glucosamine HCl on dissolution and solid state behaviours of piroxicam upon milling. Colloids and Surfaces B: Biointerfaces 103: 189-199.[Abstract] http://www.sciencedirect.com/science/article/pii/S0927776512005802
  • Hjelmgaard T, Faure S, De Santis E, Staerk D, Alexander BD, Edwards AA, Taillefumier C, Nielsen J (2012). Improved solid-phase synthesis and study of arylopeptoids with conformation-directing side chains. Tetrahedron 68(23): 4444-4454.
    http://www.sciencedirect.com/science/article/pii/S0040402011019405
  • De Santis E, Edwards AA (2012). Conformational study of peptoids. Chemistry Today, Monographic supplement series: Chiral Technologies, 30 (5): 32-36. [Open access journal].
    http://www.teknoscienze.com/Articles/Chimica-Oggi-Chemistry-Today-Conformational-study-of-peptoids.aspx#.VFd0Eecbv5o
  • De Santis E, Hjelmgaard T, Caumes C, Faure S, Alexander BD, Holder SJ, Siligardi G, Taillefumier C, Edwards AA (2012). Effect of capping groups at the N- and C-termini on the conformational preference of α,β-peptoids. Organic and Biomolecular Chemistry 10(5): 1108-1122.
  • De Santis E, Hjelmgaard T, Faure S, Roy O, Didierjean C, Alexander BD, Siligardi G, Hussain R, Jávorfi T, Edwards AA, Taillefumier C (2011). Cyclic α,β-peptoid octamers with differing side chain patterns: synthesis and conformational investigation. Amino Acids 41(3):663-672.
  • Simone MI, Edwards AA, Tranter GE, Fleet GWJF (2011) C-3 branched δ-3,5-cis- and trans-THF sugar amino acids: synthesis of the first generation of branched homooligomers. Amino Acids 41(3): 643-661.
  • Birchall LS, Roy S, Jayawarna V, Hughes M, Irvine E, Okorogheye GT, Saudi N, De Santis E, Tuttle T, Edwards AA, Ulijn RV (2011).  Exploiting CH-π interactions in supramolecular hydrogels of aromatic carbohydrate amphiphiles. Chemical Science 2(7): 1349-1355. 
  • Simone MI, Edwards AA, Cowley AR, Fleet GWJ, Watkin DJ (2010). (3R,4R,5R )-5-(Acetamidomethyl)-N-benzyl-3,4-dihydroxytetrahydrofuran-3-carboxamide. Acta Crystallographica Section E E66: o2750-o2751.
  • Simone MI, Edwards AA, Parker SG, Tranter GE, Fleet GWJ, Watkin DJ (2010). Pentafluorophenyl (3R,4R,5S )-5-{[(3R,4R,5S )-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxamido]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate. Acta Crystallographica Section E E66: o2699-o2700.
  • Al-Hamidi H, Edwards AA, Mohammad MA, Nokhodchi A (2010). Glucosamine HCl as a new carrier for improved dissolution behaviour: effect of grinding. Colloids and Surfaces B: Biointerfaces 81: 96-109.
  • Al-Hamidi H, Edwards AA, Mohamman MA, Nokhodchi A (2010). To enhance dissolution rate of poorly water soluble drugs:  Glucosamine hydrochloride as a potential carrier in solid dispersion formulations. Colloids and Surfaces B: Biointerfaces 76(1): 170-178.
  • Hjelmgaard T, Faure S, Caumes C, De Santis E, Edwards AA and Taillefumier C (2009). Convenient Solution-Phase Synthesis and Conformational Studies of Novel Linear and Cyclic α,β-Alternating Peptoids. Organic Letters 11(18): 4100-4103.
  • Simone MI, Edwards AA, Tranter GE, Fleet GWJ (2008). Carbon-branched δ-tetrahydrofuran sugar amino acids (SAAs) as dipeptide isostere scaffolds. Tetrahedron: Asymmetry 19: 2887-2894.
  • Edwards AA, Alexander BD, Fleet GWJ, Tranter GE (2008). Spectroscopic studies of oligomers containing 2,5-trans furanoid sugar amino acids. Chirality 20: 969-972.
  • Le Pevelen D, Edwards AA, Tranter GE, Watkin DJ, Fleet GWJ (2007). Isopropyl 6-amino-2,5-anhydro-6-N-(2,5-anhydro-6-azido-3,6-dideoxy-L-lyxo-hexonyl)-3,6-dideoxy-L-lyxo-hexonate 2.5-hydrate. Acta Crystallographica Section E E63: o4719-o4720.
  • Edwards AA, Sanjayan GJ, Hachisu S, Tranter GE, Fleet GWJ (2006). A novel series of oligomers from 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans stereochemistry. Tetrahedron 62: 7718-7725.
  • Edwards AA, Sanjayan GJ, Hachisu S, Soengas R, Stewart A, Tranter GE, Fleet GWJ (2006). Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships. Tetrahedron 62: 4110-4119.
  • Bream R, Watkin DJ, Soengas R, Edwards AA, Hunter SJ, Tranter GE, Fleet GWJ (2006). Cyclo {[(6-amino-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonic acid)-(D-Phe)]2}. Acta Crystallographica Section E E62: o1851-o1853.
  • Punzo F, Cowley AR, Watkin DJ, Simone MI, Edwards AA, Tranter GE, Fleet GWJ (2006). Pentafluorophenyl (3R,4R,5R)-5-{[(3R,4R,5R)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carbonylamino]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate. Acta Crystallographica Section E E62: o473-o475.
  • Watkin DJ, Watterson M, Tranter GE, Edwards AA, Fleet GWJ (2006). Isopropyl 2,5-anhydro-6-azido-3,6-dideoxy-D-xylo-hexonate. Acta Crystallographica Section E E62: o363-o365.
  • Edwards AA, Fleet GWJ, Tranter GE (2006). Classification of conformation for sugar amino acid systems using chiroptical spectroscopy. Chirality 18: 265-272.
  • Glawar AFG, Watkin DJ, Sanjayan GJ, Tranter GE, Edwards AA, Fleet GWJ (2005). Isopropyl 2,5-anhydro-3,4-di-O-tert-butyldiphenylsilyl-L-ribonate. Acta Crystallographica Section E E61: o2724-o2726.
  • Claridge TDW, Long DD, Baker CM, Odell B, Grant GH, Edwards AA, Tranter GE, Fleet GWJ, Smith MD (2005). Helix-forming carbohydrate amino acids. Journal of Organic Chemistry 70: 2082-2090.
  • Johnson SW, Jenkinson (nee Barker) SF, Perez-Victoria I, Edwards A, Claridge TDW, Tranter G, Fleet GWJ, Jones JH (2005). Conformational studies of oligomeric oxetane-based dipeptide isosteres derived from L-rhamnose or D-xylose. Journal of Peptide Science 11: 517-524.
  • Edwards AA, Fleet GWJ, Mayes BA, Hunter SJ, Tranter GE (2005). Circular dichroism studies of carbopeptoid-cyclodextrins. Chirality 17: S114-S119.
  • Humphreys S, Watkin DJ, Sanjayan GJ, Tranter GE, Edwards AA, Fleet GWJ (2005). Isopropyl 2,5-anhydro-4-(2,5-anhydro-4-azido-3-O-tert-butyldiphenylsilyl-4-deoxy-L-ribonyl-amino)-3-O-tert-butyldiphynylsilyl-4-deoxy-L-ribonate. Acta Crystallographica Section E E61: o918-o919.
  • Mayes BA, Stetz RJE, Watterson MP, Edwards A, Ansell CWG, Tranter GE, Fleet GWJ (2004). Towards hydroxylated nylon 6: Linear and cyclic oligomers from a protected 6-amino-6-deoxy-D-galactonate - a novel class of carbopeptoid-cyclodextrin (CPCD). Tetrahedron: Asymmetry 15: 627-638.
  • Cooper RI, Edwards A, Fleet GWJ, Watkin DJ (2003). Isopropyl 6-amino-2,5-anhydro-3,6-dideoxy-6-N-(2,5-anhydro-6-azido-3,6-dideoxy-L-arabino-hexonyl)-L-arabino-hexonate. Acta Crystallographica Section E E59: o1712-o1714.
  • Watterson MP, Edwards AA, Leach JA, Smith MD, Ichihara O, Fleet GWJ (2003). Synthesis of all diastereomeric methyl 2,5-anhydro-3-deoxy-hexonates: C-glycosyl derivatives of 2-deoxy-ribose and precursors to tetrahydrofuran templated gamma-amino acids. Tetrahedron Letters 44: 5853-5857.

Book chapters

  • Edwards A, Jenkinson S (2012). “Perspective and Concepts: Overview of Techniques for Assigning Stereochemistry.” Volume 8, pp. 39-53. Comprehensive Chirality. Editors: Carreira E, Yamamoto, H. Elsevier, ISBN: 9780080951676
  • Edwards AA, Alexander BD (2010). “Organic Applications of UV-Visible Absorption Spectroscopy.” Volume 2, 2030-2039. Encyclopedia of Spectroscopy and Spectrometry, 2nd Edition. Editors: Lindon J, Tranter GE, Koppenaal D. ACADEMIC PRESS, ISBN 978-0-12-374417-3.

Conference preceedings

  • Edwards AA, Birchall LS, Jayawarna V, Roy S, Hughes M, Tuttle T, Saudi N, Okorgheye G, Ulijn RV (2010). Fmoc hydrogels from aromatic carbohydrate amphiphiles. Journal of Pharmacy and Pharmacology, 62: 1331-1332.
  • Al-Hamidi H, Edwards AA, Mohammad MA, Nokhodchi A (2010). Gluconolactone as a Potential Carrier to Improve Dissolution Rate of Carbamezepine from Physical Mixtures and Solid Dispersion Formulations. Journal of Pharmacy and Pharmacology 62: 1437-1438.
  • Al-Hamidi H, Edwards A, Mohammad MA, Nokhodchi A (2009). Dissolution enhancement of carbamazepine: solid dispersion formulations with glucosamine and the effect of different solvents.Journal of Pharmacy and Pharmacology 61: A58.
  • Edwards AA, Fleet GWJ, Mayes BA, et al. (2005). Chiroptical spectroscopy and sugar amino acid systems. Abstracts of papers of the American Chemical Society 230: U682.

Other

  • De Santis E, Edwards AA (2012). Effect of side chains on the conformational preference of cyclic α,β-peptoids. Diamond Light Source Annual Report, 36-37.
  • Edwards AA (2010). Establishing the conformational preference of a novel α,β-peptoid backbone. Diamond Light Source Annual Report, 76-77.

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