PEGylated Protein Drugs: Basic Science and Clinical Applications PDF
Preview PEGylated Protein Drugs: Basic Science and Clinical Applications
8678 MDT Veronese 3. Umbruch,28.7.2009 Satz: Klaus Hensler, Kreuzlingen [email protected] Milestones in Drug Therapy MDT Series Editors Prof. Dr. Michael J. Parnham PhD Prof. Dr. J. Bruinvels Director of Preclinical Discovery Sweelincklaan 75 Centre of Excellence in Macrolide NL-3723 JC Bilthoven Drug Discovery The Netherlands GlaxoSmithKline Research Centre Zagreb Ltd. Prilaz baruna Filipovic´a 29 HR-10000 Zagreb Croatia PEGylated Protein Drugs: Basic Science and Clinical Applications Edited by Francesco M. Veronese Birkhäuser Basel · Boston · Berlin Editors Francesco M. Veronese Department of Pharmaceutical Sciences University of Padova 35131 Padova Italy Advisory Board J.C. Buckingham (Imperial College School of Medicine,London,UK) R.J.Flower (The William Harvey Research Institute,London,UK) A.G. Herman (Universiteit Antwerpen,Antwerp,Belgium) P.Skolnick (NYU Langone Medical Center,New York,NY,USA) Library of Congress Control Number:2009928445 Bibliographic information published by Die Deutsche Bibliothek Die Deutsche Bibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data is available in the Internet at <://dnb.ddb.de>. ISBN 978-3-7643-8678-8 Birkhäuser Verlag,Basel - Boston - Berlin The publisher and editor can give no guarantee for the information on drug dosage and administration contained in this publication. The respective user must check its accuracy by consulting other sources of reference in each individual case. The use of registered names,trademarks etc. in this publication,even if not identified as such,does not implythat they are exempt from the relevant protective laws and regulations or free for general use. This work is subject to copyright. All rights are reserved,whether the whole or part of the material is concerned,specifically the rights of translation,reprinting,re-use of illustrations,recitation,broad- casting,reproduction on microfilms or in other ways,and storage in data banks. For any kind of use, permission of the copyright owner must be obtained. ©2009 Birkhäuser Verlag,P.O. Box 133,CH-4010 Basel,Switzerland Part of Springer Sciebnce+Business Media Printed on acid-free paper produced from chlorine-free pulp. TCF ∞ Cover illustration:see p. 191. Reproduced with kind permission of Taylor and Francis Group LLC. Printed in Germany ISBN 978-3-7643-8678-8 e-ISBN:978-3-7643-8679-5 987654321 www.birkhauser.ch V Contents List of contributors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . VII Ruth Duncan and Francesco M. Veronese Preface:PEGylated protein conjugates:A new class of therapeutics for the 21st century . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 Francesco M. Veronese,Anna Mero and Gianfranco Pasut Protein PEGylation,basic science and biological applications . . . . . . . 11 Gian Maria Bonora and Sara Drioli Reactive PEGs for protein conjugation . . . . . . . . . . . . . . . . . . . . . . . . . 33 Ji-Won Choi,Antony Godwin,Sibu Balan,Penny Bryant,Yuehua Cong,EsteraPawlisz,Manuchehr Porssa,Norbert Rumpf,Ruchi Singh,Keith Powell and Steve Brocchini Rebridging disulphides:site-specific PEGylation by sequential bis-alkylation ............................................. 47 MauroSergi,Francesca Caboi,Carlo Maullu,Gaetano Orsini andGiancarlo Tonon Enzymatic techniques for PEGylation of biopharmaceuticals . . . . . . . 75 Angelo Fontana,Barbara Spolaore,Anna Mero and Francesco M. Veronese The site-specific TGase-mediated PEGylation of proteins occurs at flexible sites . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 89 Conan J.Fee Protein conjugates purification and characterization . . . . . . . . . . . . . . . 113 Rob Webster,Victoria Elliott,B. Kevin Park,Donald Walker, Mark Hankin and Philip Taupin PEG and PEG conjugates toxicity:towards an understanding of the toxicity of PEG and its relevance to PEGylated biologicals . . . . . . 127 Jonathan K. Armstrong The occurrence,induction,specificity and potential effect of antibodies against poly(ethylene glycol) . . . . . . . . . . . . . . . . . . . . . . . . 147 VI Contents Graham Molineux Pegfilgrastim – designing an improved form of rmetHuG-CSF . . . . . . 169 Rory F. Finn PEGylation of human growth hormone:strategies and properties . . . . 187 Gianfranco Pasut PEGylated αinterferons:two different strategies to achieve increased efficacy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 205 Michael S. Hershfield,John S. Sundy,Nancy J. Ganson and Susan J. Kelly Development of PEGylated mammalian urate oxidase as a therapy for patients with refractory gout . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 217 AndrewM. Nesbitt,Sue Stephens and Elliot K. Chartash Certolizumabpegol:a PEGylated anti-tumour necrosis factor alpha biological agent . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 229 Anna Mero,Gianfranco Pasut and Francesco M. Veronese PEG:auseful technologyin anticancer therapy .................. 255 TaceyX. Viegas and Francesco M. Veronese Regulatory strategy and approval processes considered for PEG-drug conjugates and other nanomedicines . . . . . . . . . . . . . . . . . . 273 Index .................................................... 283 VII List of contributors Jonathan K. Armstrong, Department of Physiology and Biophysics, Keck School of Medicine, University of Southern California, 1333 San Pablo Street, Los Angeles, California 90033, USA; e-mail: jonathan.armstrong@ usc.edu Sibu Balan, PolyTherics Ltd. London Bioscience Innovation Centre, 2 Royal College Street, London, NW1 0TU, UK; e-mail: sibu.balan@ polytherics.co.uk Gian Maria Bonora, Department of Chemical Sciences, Via Giorgieri 1, University of Trieste,34127 Trieste,Italy; e-mail:[email protected] Steve Brocchini, PolyTherics Ltd. London Bioscience Innovation Centre, 2Royal College Street,London,NW1 0TU,UK; e-mail:steve.brocchini@ polytherics.co.uk Penny Bryant, PolyTherics Ltd. London Bioscience Innovation Centre, 2 Royal College Street, London, NW1 0TU, UK; e-mail: penny.bryant@ polytherics.co.uk Francesca Caboi, Bio-Ker S.r.l, Parco Scientifico e Tecnologico della Sardegna,09010 Pula,Cagliari,Italy Elliot K. Chartash,Clinical Development,UCB Inc,Atlanta,GA,USA Ji-Won Choi, PolyTherics Ltd. London Bioscience Innovation Centre, 2 Royal College Street, London, NW1 0TU, UK; e-mail: ji-won.choi@ polytherics.co.uk Yuehua Cong, PolyTherics Ltd. London Bioscience Innovation Centre, 2 Royal College Street, London, NW1 0TU, UK; e-mail: yuehua.cong@ polytherics.co.uk Sara Drioli, Department of Chemical Sciences,Via Giorgieri 1, University of Trieste,34127 Trieste,Italy; e-mail:[email protected] Ruth Duncan, Centre for Polymer Therapeutics, Welsh School of Pharmacy, Redwood Building, King Edward VII Avenue, Cardiff, CF10 3NB, UK; e-mail:[email protected] Victoria Elliott, University of Liverpool, MRC Centre for Drug Safety Science, Department of Pharmacology and Therapeutics, Liverpool. L69 3BX,UK; e-mail:[email protected] Conan J. Fee, Department of Chemical & Process Engineering, University of Canterbury, Private Bag 4800, Christchurch 8040, New Zealand; e-mail: [email protected] Rory F. Finn, Pfizer Inc, 700 Chesterfield Parkway West, Chesterfield, MO 63017,USA; e-mail:[email protected] Angelo Fontana,CRIBI,Biotechnology Centre,University of Padua,Viale G. Colombo 3,35121 Padua,Italy; e-mail:[email protected] VIII List of contributors Nancy J. Ganson,Duke University Medical Center,Durham,NC 27710,USA Antony Godwin, PolyTherics Ltd. London Bioscience Innovation Centre, 2 Royal College Street, London, NW1 0TU, UK; e-mail: antony.godwin@ polytherics.co.uk Mark Hankin, DSRD, Pfizer Global Research and Development, Kent, CT13 9NJ,UK; e-mail:[email protected] Michael S. Hershfield, Box 3049, 418 Sands Building, Duke University Medical Center, Durham, NC 27710, USA; e-mail: msh@biochem. duke.edu Susan J. Kelly,Duke University Medical Center,Durham,NC 27710,USA Carlo Maullu, Bio-Ker S.r.l, Parco Scientifico e Tecnologico della Sardegna, 09010 Pula,Cagliari,Italy Anna Mero,Department of Pharmaceutical Sciences,University of Padua,Via F. Marzolo 5,35131 Padua,Italy; e-mail:[email protected] Graham Molineux,Amgen Inc., Mailstop 15-2-A, One Amgen Center Drive, Thousand Oaks,California 91320,USA; e-mail:[email protected] Andrew M. Nesbitt, Inflammation Research, UCB Celltech, 208 Bath Road, Slough SL1 3WE,United Kingdom; e-mail:[email protected] Gaetano Orsini,Bio-Ker S.r.l,Parco Scientifico e Tecnologico della Sardegna, 09010 Pula,Cagliari,Italy B. Kevin Park,University of Liverpool,MRC Centre for Drug Safety Science, Department of Pharmacology and Therapeutics, Liverpool. L69 3BX, UK; e-mail:[email protected] Gianfranco Pasut, Department of Pharmaceutical Sciences, University of Padua, Via F. Marzolo 5, 35131 Padua, Italy; e-mail: gianfranco.pasut@ unipd.it Estera Pawlisz, PolyTherics Ltd. London Bioscience Innovation Centre, 2 Royal College Street, London, NW1 0TU, UK; e-mail: estera.pawlisz@ polytherics.co.uk Manuchehr Porssa, PolyTherics Ltd. London Bioscience Innovation Centre, 2 Royal College Street, London, NW1 0TU, UK; e-mail: manu.porssa@ polytherics.co.uk Keith Powell,PolyTherics Ltd. London Bioscience Innovation Centre,2 Royal College Street, London, NW1 0TU, UK; e-mail: keith.powell@ polytherics.co.uk Norbert Rumpf, PolyTherics Ltd. London Bioscience Innovation Centre, 2 Royal College Street, London, NW1 0TU, UK; e-mail: norbert.rumpf@ polytherics.co.uk Mauro Sergi, Ablynx nv, Technologiepark 4, 9052 Zwijnaarde, Belgium; e-mail:[email protected] Ruchi Singh, PolyTherics Ltd. London Bioscience Innovation Centre, 2 Royal College Street, London, NW1 0TU, UK; e-mail: ruchi.singh@ polytherics.co.uk Barbara Spolaore, CRIBI, Biotechnology Centre, University of Padua, Viale G.Colombo 3,35121 Padua,Italy; e-mail:[email protected] List of contributors IX Sue Stephens, Non-Clinical Development, UCB Celltech, Slough SL1 3WE, UK John S. Sundy,Duke University Medical Center,Durham,NC 27710,USA Philip Taupin, DSRD, Pfizer Global Research and Development, Kent, CT13 9NJ,UK; e-mail:[email protected] Giancarlo Tonon, Bio-Ker S.r.l, Parco Scientifico e Tecnologico della Sardegna,09010 Pula,Cagliari,Italy Francesco M. Veronese,Department of Pharmaceutical Sciences,University of Padua,Via F. Marzolo 5, 35131 Padua, Italy; e-mail: francesco.veronese@ unipd.it Tacey X. Viegas,Serina Therapeutics,Inc.,601 Genome Way,Huntsville,AL 35806,USA; e-mail:[email protected] Donald Walker, Pharmacokinetics, Dynamics and Metabolism, Pfizer Global Research and Development, Kent. CT13 9NJ, UK; e-mail: don.walker@ pfizer.com Rob Webster, Pharmacokinetics, Dynamics and Metabolism, Pfizer Global Research and Development, Kent. CT13 9NJ, UK; e-mail: rob.webster@ pfizer.com
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