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• Journal article
  Smith LD, Leatherbarrow RJ, Spivey AC, 2013,

  Development of small molecules to target the IgE:FcεRI protein-protein interaction in allergies

  , FUTURE MEDICINAL CHEMISTRY, Vol: 5, Pages: 1423-1435, ISSN: 1756-8919
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  • Citations: 9
• Journal article
  George GPC, Pisaneschi F, Stevens E, Nguyen QD, Åberg O, Spivey ACet al., 2013,

  Scavenging strategy for specific activity improvement: application to a new CXCR4-specific cyclopentapeptide positron emission tomography tracer

  , J. Label Compd. Radiopharm.

  Huisgen cycloaddition is attractive to label peptide because of its rapidity and bioorthogonality. However, for larger tracers, the physico-chemical differences between the precursor and the tracer are usually insufficient to allow their separation by HPLC, reducing the specific activity. This is of importance for peptidic tracers because the combination of their high-affinity receptor with low specific activity results in the precursor saturating the receptors, causing non-specific tracer binding. Here, we report a fast, one-pot, general strategy to circumvent this issue, yielding a tracer of improved specific activity. It consists in adding a lipophilic azide after the labeling step to scavenge unreacted precursor into a more lipophilic species that does not co-elute with the tracer. We applied this strategy to a new fluorinated cyclopentapeptidic CXCR4 antagonist for the PET imaging of cancer, CCIC15, for which we managed to reduce the apparent peptide concentration by a factor of 34 in 10 min. This tracer was radiolabeled by click chemistry with 2-[18F]fluoroethylazide, yielding the tracer in 18 ±6% (n = 5) end-of-synthesis radiochemical yields (EOS-RCY) in 1.5 h from [18F]fluoride with a specific activity of 19.4 GBq μmol 1. Preliminary biological evaluation of the probe confirmed potency and specificity for CXCR4; further biological evaluation is underway.

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• Journal article
  Murray JI, Spivey AC, Woscholski R, 2013,

  Alternative synthetic tools to phospho-specific antibodies for phosphoproteome analysis: progress and prospects.

  , J Chem Biol, Vol: 6, Pages: 175-184, ISSN: 1864-6158

  Signal transduction cascades in living systems are often controlled via post-translational phosphorylation and dephosphorylation of proteins. These processes are catalyzed in vivo by kinase and phosphatase enzymes, which consequently play an important role in many disease states, including cancer and immune system disorders. Current techniques for studying the phosphoproteome (isotopic labeling, chromatographic techniques, and phosphospecific antibodies), although undoubtedly very powerful, have yet to provide a generic tool for phosphoproteomic analysis despite the widespread utility such a technique would have. The use of small molecule organic catalysts that can promote selective phosphate esterification could provide a useful alternative to current state-of-the-art techniques for use in, e.g., the labeling and pull-down of phosphorylated proteins. This report reviews current techniques used for phosphoproteomic analysis and the recent use of small molecule peptide-based catalysts in phosphorylation reactions, indicating possible future applications for this type of catalyst as synthetic alternatives to phosphospecific antibodies for phosphoproteome analysis.

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• Journal article
  Evans HL, Carroll L, Nguyen Q-D, Aboagye EO, Spivey Aet al., 2013,

  Copper-free 'click' chemistry as a potential pre-targeting tool for PET imaging

  , JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, Vol: 56, Pages: S204-S204, ISSN: 0362-4803
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  • Citations: 1
• Journal article
  George GPC, Stevens E, Pisaneschi F, Aberg O, Nguyen Q-D, Spivey AC, Aboagye EOet al., 2013,

  Synthesis, radiolabelling and biological evaluation of new PET probes for CXCR4-specific imaging

  , JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, Vol: 56, Pages: S409-S409, ISSN: 0362-4803
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  • Citations: 1
• Book chapter
  Spivey AC, Arseniyadis S, 2013,

  Regio-and Position Selective Reactions and Desymmetrizations

  , Comprehensive Enantioselective Organocatalysis Catalysts Reactions and Applications Volume 1 Privileged Catalysts Volume 2 Activations Volume 3 Reactions and Applications, Pages: 1225-1284

  This chapter contains sections titled: • Kinetic Resolution of Alcohols • Kinetic Resolution of Amines.

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• Journal article
  Webber MJ, Warren SA, Grainger DM, Weston M, Clark S, Woodhead SJ, Powell L, Stokes S, Alanine A, Stonehouse JP, Frampton CS, White AJP, Spivey ACet al., 2013,

  Towards the enantioselective synthesis of (-)-euonyminol - preparation of a fully functionalised lower-rim model

  , ORGANIC & BIOMOLECULAR CHEMISTRY, Vol: 11, Pages: 2514-2533, ISSN: 1477-0520
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  • Citations: 17
• Book chapter
  Spivey AC, Arseniyadis S, 2013,

  Regio- and Position Selective Reactions and Desymmetrizations

  , COMPREHENSIVE ENANTIOSELECTIVE ORGANOCATALYSIS: CATALYSTS, REACTIONS, AND APPLICATIONS, VOLS 1-3, Editors: Dalko, Publisher: BLACKWELL SCIENCE PUBL, Pages: 1225-1284, ISBN: 978-3-527-33236-6
  • Author Web Link
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  • Citations: 5
• Journal article
  Larionov E, Mahesh M, Spivey AC, Wei Y, Zipse Het al., 2012,

  Theoretical Prediction of Selectivity in Kinetic Resolution of Secondary Alcohols Catalyzed by Chiral DMAP Derivatives

  , JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Vol: 134, Pages: 9390-9399, ISSN: 0002-7863
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  • Citations: 70
• Journal article
  Offermann DA, McKendrick JE, Sejberg JJP, Mo B, Holdom MD, Helm BA, Leatherbarrow RJ, Beavil AJ, Sutton BJ, Spivey ACet al., 2012,

  Synthesis and Incorporation into Cyclic Peptides of Tolan Amino Acids and Their Hydrogenated Congeners: Construction of an Array of A-B-loop Mimetics of the Cε3 Domain of Human IgE.

  , J Org Chem

  The disruption of the human immunolobulin E-high affinity receptor I (IgE-FcεRI) protein-protein interaction (PPI) is a validated strategy for the development of anti asthma therapeutics. Here, we describe the synthesis of an array of conformationally constrained cyclic peptides based on an epitope of the A-B loop within the Cε3 domain of IgE. The peptides contain various tolan (i.e., 1,2-biarylethyne) amino acids and their fully and partially hydrogenated congeners as conformational constraints. Modest antagonist activity (IC(50) ∼660 μM) is displayed by the peptide containing a 2,2'-tolan, which is the one predicted by molecular modeling to best mimic the conformation of the native A-B loop epitope in IgE.

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• Journal article
  Evans HL, Slade RL, Carroll L, Smith G, Nguyen Q-D, Iddon L, Kamaly N, Stoeckmann H, Leeper FJ, Aboagye EO, Spivey ACet al., 2012,

  Copper-free click-a promising tool for pre-targeted PET imaging

  , CHEMICAL COMMUNICATIONS, Vol: 48, Pages: 991-993, ISSN: 1359-7345
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  • Citations: 40
• Journal article
  Warren SA, Stokes S, Frampton CS, White AJP, Spivey ACet al., 2012,

  Synthesis of <i>anti</i> and <i>syn</i> hydroxy-<i>iso</i>-evoninic acids

  , ORGANIC & BIOMOLECULAR CHEMISTRY, Vol: 10, Pages: 4685-4688, ISSN: 1477-0520
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  • Citations: 4
• Journal article
  Webber MJ, Weston M, Grainger DM, Lloyd S, Warren SA, Powell L, Alanine A, Stonehouse JP, Frampton CS, White AJP, Spivey ACet al., 2011,

  An Ireland-Claisen Rearrangement/Lactonisation Cascade as a Key Step in Studies Towards the Synthesis of (-)-Euonyminol

  , SYNLETT, Pages: 2693-2696, ISSN: 0936-5214
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  • Citations: 6
• Journal article
  Carr JL, Sejberg JJP, Saab F, Holdom MD, Davies AM, White AJ, Leatherbarrow RJ, Beavil AJ, Sutton BJ, Lindell SD, Spivey ACet al., 2011,

  Synthesis of the C19 methyl ether of aspercyclide A via germyl-Stille macrocyclisation and ELISA evaluation of both enantiomers following optical resolution.

  , Org Biomol Chem, Vol: 9, Pages: 6814-6824

  Aspercyclide A (1) is a biaryl ether containing 11-membered macrocyclic natural product antagonist of the human IgE-FcεRI protein-protein interaction (PPI); a key interaction in the signal transduction pathway for allergic disorders such as asthma. Herein we report a novel approach to the synthesis of the C19 methyl ether of aspercyclide A, employing a Pd(0)-catalysed, fluorous-tagged alkenylgermane/arylbromide macrocyclisation (germyl-Stille reaction) as the key step, and evaluation of both enantiomers of this compound via ELISA following optical resolution by CSP-HPLC. A crystal structure for germyl hydride 27 is also reported.

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• Journal article
  Tseng C-C, Li M, Mo B, Warren SA, Spivey ACet al., 2011,

  Stereocontrolled Formation of Styrenes by Pd(0)-catalyzed Cross-coupling of Photoactivated (<i>E</i>)-Alkenylgermanes with Aryl Bromides

  , CHEMISTRY LETTERS, Vol: 40, Pages: 995-997, ISSN: 0366-7022
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  • Citations: 10
• Patent
  Spivey AC, Aboagye E, Pisaneschi F, Smith Get al., 2011,

  Quinoline Derivaties used as PET Imaging Agents

  , WO/2011/077095

  There is provided compounds of formula (I), wherein R1, R2, X1, X2, and X3 have meanings given in the description, and pharmaceutically-acceptable salts thereof, which compounds are useful as positron emission tomography (PET) imaging agents, useful in the treatment of diseases in which inhibition of epidermal growth factor receptor tyrosine kinase activity or the inhibition of HER2 activity is desired and/or required, and useful in the treatment of cancer.

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• Journal article
  Thiruchelvam PTR, Lai C-F, Hua H, Thomas RS, Hurtado A, Hudson W, Bayly AR, Kyle FJ, Periyasamy M, Photiou A, Spivey AC, Ortlund EA, Whitby RJ, Carroll JS, Coombes RC, Buluwela L, Ali Set al., 2011,

  The liver receptor homolog-1 regulates estrogen receptor expression in breast cancer cells

  , BREAST CANCER RESEARCH AND TREATMENT, Vol: 127, Pages: 385-396, ISSN: 0167-6806
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  • Citations: 61
• Journal article
  Paddock VL, Phipps RJ, Conde-Angulo A, Blanco-Martin A, Giro-Manas C, Martin LJ, White AJP, Spivey ACet al., 2011,

  (±)-<i>trans,cis</i>-4-Hydroxy-5,6-di-<i>O</i>-isopropylidenecyclohex-2-ene-1-one: Synthesis and Facile Dimerization to Decahydrodibenzofurans

  , JOURNAL OF ORGANIC CHEMISTRY, Vol: 76, Pages: 1483-1486, ISSN: 0022-3263
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  • Citations: 22
• Journal article
  Pisaneschi F, Sejberg JJP, Blain C, Ng WH, Aboagye EO, Spivey ACet al., 2011,

  2-Substituted-2,3-dihydro-1<i>H</i>-quinolin-4-ones via Acid-Catalyzed Tandem Rupe Rearrangement-Donnelly-Farrell Ring Closure of 2-(3′-Hydroxypropynyl)anilines

  , SYNLETT, Pages: 241-244, ISSN: 0936-5214
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  • Citations: 21
• Journal article
  Haning H, Giro-Manas C, Paddock VL, Bochet CG, White AJP, Bernardinelli G, Mann I, Oppolzer W, Spivey ACet al., 2011,

  Total synthesis of the Amaryllidaceae alkaloid clivonine

  , ORGANIC & BIOMOLECULAR CHEMISTRY, Vol: 9, Pages: 2809-2820, ISSN: 1477-0520
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  • Citations: 16
• Journal article
  Arseniyadis S, Mahesh M, McDaid P, Hampel T, Davey SG, Spivey ACet al., 2011,

  STUDIES TOWARDS THE <i>N</i>-ACYLATIVE KINETIC RESOLUTION OF NOBIN

  , COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, Vol: 76, Pages: 1239-1253, ISSN: 0010-0765
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  • Citations: 16
• Journal article
  Pisaneschi F, Nguyen Q-D, Shamsaei E, Glaser M, Robins E, Kaliszczak M, Smith G, Spivey AC, Aboagye EOet al., 2010,

  Development of a new epidermal growth factor receptor positron emission tomography imaging agent based on the 3-cyanoquinoline core: Synthesis and biological evaluation

  , BIOORGANIC & MEDICINAL CHEMISTRY, Vol: 18, Pages: 6634-6645, ISSN: 0968-0896
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  • Citations: 49
• Journal article
  Manas CG, Paddock VL, Bochet CG, Spivey AC, White AJP, Mann I, Oppolzer Wet al., 2010,

  Total Synthesis of the Lycorenine-Type Amaryllidaceae Alkaloid (±)-Clivonine via a Biomimetic Ring-Switch from a Lycorine-Type Progenitor

  , JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, Vol: 132, Pages: 5176-5178, ISSN: 0002-7863
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  • Citations: 15
• Journal article
  Spivey AC, Laraia L, Bayly AR, Rzepa HS, White AJPet al., 2010,

  Stereoselective Synthesis of <i>cis</i>- and <i>trans</i>-2,3-Disubstituted Tetrahydrofurans via Oxonium-Prins Cyclization: Access to the Cordigol Ring System

  , ORGANIC LETTERS, Vol: 12, Pages: 900-903, ISSN: 1523-7060
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  • Citations: 73
• Journal article
  Carr JL, Offermann DA, Holdom MD, Dusart P, White AJP, Beavil AJ, Leatherbarrow RJ, Lindell SD, Sutton BJ, Spivey ACet al., 2010,

  Total synthesis of (±)-aspercyclide A and its C19 methyl ether

  , CHEMICAL COMMUNICATIONS, Vol: 46, Pages: 1824-1826, ISSN: 1359-7345
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  • Citations: 25
• Journal article
  Spivey AC, Arseniyadis S, 2010,

  Amine, alcohol and phosphine catalysts for acyl transfer reactions.

  , Top Curr Chem, Vol: 291, Pages: 233-280, ISSN: 0340-1022

  An overview of the area of organocatalytic asymmetric acyl transfer processes is presented including O- and N-acylation. The material has been ordered according to the structural class of catalyst employed rather than reaction type with the intention to draw mechanistic parallels between the manner in which the various reactions are accelerated by the catalysts and the concepts employed to control transfer of chiral information from the catalyst to the substrates.

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• Journal article
  Spivey AC, Tseng C-C, 2010,

  A method for parallel solid-phase synthesis of iodinated analogs of the cannabinoid receptor type I (CB₁) inverse agonist rimonabant.

  , Methods Enzymol, Vol: 485, Pages: 499-525

  Rimonabant (acomplia) is a 1,5-diarylpyrazole derivative that acts as a type 1 cannabinoid receptor (CB₁) inverse agonist. Here, we overview the role of this type of molecule in regulation of these receptors and their potential as starting points for the development of molecular probes to image the central nervous system (CNS). We then describe a novel protocol for the solid-phase parallel chemical synthesis of iodinated rimonabant analogs using germanium-functionalized, cross-linked polystyrene as the solid-support (or "resin"). The method allows for rapid derivatization at the key C-3 position of rimonabant from a common resin-bound precursor. The desired iodinated analogs are then obtained by ipso-iododegermylative cleavage from the resin using sodium iodide/N-chlorosuccinimide (NCS) in a fashion that ought to be readily adapted to the rapid preparation of isotopically labeled iodine derivatives for molecular imaging of CNS activity by positron emission tomography (PET, using ¹²⁴I) and single photon emission computerized tomography (SPECT, using (¹²³I) techniques. Toward this goal, we also show that the NCS-derived succinimide by-product that is released from the resin concomitantly with the potential imaging probe molecules can be readily and selectively removed by treatment of the crude soluble product mixture with a solid-supported hydrazide scavenger resin.

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• Journal article
  Spivey AC, Tseng C-C, 2010,

  A METHOD FOR PARALLEL SOLID-PHASE SYNTHESIS OF IODINATED ANALOGS OF THE CANNABINOID RECEPTOR TYPE I (CB₁) INVERSE AGONIST RIMONABANT

  , METHODS IN ENZYMOLOGY, VOLUME 485: CONSTITUTIVE ACTIVITY IN RECEPTORS AND OTHER PROTEINS, PART B, Vol: 485, Pages: 499-525, ISSN: 0076-6879
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• Journal article
  Spivey AC, Diaper CM, 2009,

  Silicon and Germanium Linker Units

  , Pages: 467-504
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  • Citations: 1
• Journal article
  Spivey AC, Tseng C-C, Jones TC, Kohler AD, Ellames GJet al., 2009,

  A Method for Parallel Solid-Phase Synthesis of Iodinated Analogues of the CB₁ Receptor Inverse Agonist Rimonabant

  , ORGANIC LETTERS, Vol: 11, Pages: 4760-4763, ISSN: 1523-7060
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  • Citations: 11

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