1,554
Views
268
CrossRef citations to date
0
Altmetric
Reviews

Advances in PEGylation of important biotech molecules: delivery aspects

, , , &
Pages 371-383 | Published online: 21 Apr 2008

Bibliography

  • Beck A, Klinguer-Hamour C, Bussat MC, et al. Peptides as tools and drugs for immunotherapies. J Pept Sci 2007;13:588-602
  • Malik DK, Baboota S, Ahuja A, et al. Recent advances in protein and peptide drug delivery systems. Curr Drug Deliv 2007;4:141-51
  • Syed S, Schuyler PD, Kulczycky M, et al. Potent antithrombin activity and delayed clearance from the circulation characterize recombinant hirudin genetically fused to albumin. Blood 1997;89:3243-52
  • Prego C, Torres D, Fernandez-Megia E, et al. Chitosan-PEG nanocapsules as new carriers for oral peptide delivery. Effect of chitosan pegylation degree. J Control Rel 2006;11:299-308
  • Schmidt PG, Campbell KM, Hinds KD, et al. PEGylated bioactive molecules in biodegradable polymer microparticles. Expert Opin Biol Ther 2007;7:1427-36
  • Veronese FM, Pasut G. PEGylation, successful approach to drug delivery. Drug Discov Today 2005;10:1451-8
  • Abuchowski A, McCoy JR, Palczuk NC, et al. Effect of covalent attachment of polyethylene glycol on immunogenicity and circulating life of bovine liver catalase. J Biol Chem 1977;252:3582-6
  • Abuchowski A, van Es T, Palczuk NC, et al. Alteration of immunological properties of bovine serum albumin by covalent attachment of polyethylene glycol. J Biol Chem 1977;252:3578-81
  • Zalipsky S. Chemistry of polyethylene glycol conjugates with biologically active molecules. Adv Drug Deliv Rev 1995;16:157-82
  • Fee CJ. Size comparison between proteins PEGylated with branched and linear poly(ethylene glycol) molecules. Biotechnol Bioeng 2007;98:725-31
  • Fung WJ, Porter JE, Bailon P. Strategies for the preparation and characterization of polyethylene glycol (PEG) conjugated pharmaceutical proteins. Polym Preprints 1997;38:565-6
  • Youn YS, Jung JY, Oh SH, et al. Improved intestinal delivery of salmon calcitonin by Lys18-amine specific PEGylation: stability, permeability, pharmacokinetic behavior and in vivo hypocalcemic efficacy. J Control Rel 2006;114:334-42
  • Bailon P, Palleroni A, Schaffer CA, et al. Rational design of a potent, long-lasting form of interferon: a 40 kDa branched polyethylene glycol-conjugated interferon alpha-2a for the treatment of hepatitis C. Bioconjug Chem 2000;12:195-202
  • Chang LC, Lee HF, Chung MJ, Yang VC. PEG-modified protamine with improved pharmacological/pharmaceutical properties as a potential protamine substitute: synthesis and in vitro evaluation. Bioconjug Chem 2005;16:147-55
  • Gregoriadis G, Jain S, Papaioannou I, et al. Improving the therapeutic efficacy of peptides and proteins: a role for polysialic acids. Int J Pharm 2005;300:125-30
  • Roberts MJ, Bentley MD, Harris JM. Chemistry for peptide and protein PEGylation. Adv Drug Deliv Rev 2002;54:459-76
  • Bailey FE, Koleske JV. Poly(Ethylene Oxide). New York: Academic Press; 1976
  • Rabkin R, Dahl DC. Biological Barriers in Protein Delivery: Plenum Press, New York; 1993
  • Webster R, Didier E, Harris P, et al. PEGylated proteins: evaluation of their safety in the absence of definitive metabolism studies. Drug Metab Dispos 2007;35:9-16
  • Modi MW, Fulton JS, Buchmann DK, et al. Clearance of PEGylated (40 kDa) interferon alfa-2a (Pegasys®) is primarily hepatic. Hepatol 2000;32:371A
  • Pasut G, Veronese FM. Polymer drug conjugation, recent achievements and general strategies. Prog Polym Sci 2007;32:933-61
  • Pasut AG, Veronese FM. Protein, peptide and non-peptide drug PEGylation for therapeutic application. Expert Opin Ther Patents 2004;14:859-94
  • Herman S, Hooftman G, Schacht E. Poly(ethylene glycol) with reactive end groups: I Modification of proteins. J Bioact Biocomp Polymer 1995;10:145-87
  • Veronese FM. Peptide and protein PEGylation: a review of problems and solutions. Biomaterials 2001;22:405-17
  • Caliceti P, Veronese FM. Pharmacokinetic and biodistribution properties of poly(ethylene glycol)-protein conjugates. Adv Drug Deliv Rev 2003;55:1261-77
  • Fishburn CS. The pharmacology of PEGylation: Balancing PD with PK to generate novel therapeutics. J Pharm Sci 2008: published online 15 Jan 2008, doi:10.1002/jps.21278
  • Helmlinger G, Yuan F, Dellian M, et al. Interstitial pH and pO2 gradients in solid tumors in vivo: high-resolution measurements reveal a lack of correlation. Nat Med 1997;3:177-82
  • Tannock IF, Rotin D. Acid pH in tumors and its potential for therapeutic exploitation. Cancer Res 1989;49:4373-84
  • Zalipsky S, Seltzer R, Menon-Rudolph S. Evaluation of a new reagent for covalent attachment of polyethylene glycol to proteins. Biotech App Biochem 1992;15:100-14
  • Bentley MD, Roberts MJ, Harris JM. Reductive amination using poly(ethylene glycol) acetaldehyde hydrate generated in situ: applications to chitosan and lysozyme. J Pharm Sci 1998;87:1446-9
  • Bentley MD, Harris JM, Kozlowski A. Heterobifunctional poly(ethylene glycol) derivatives and methods for their preparation. PCT US99/23536 (1999)
  • Crawford J. Once-per-cycle pegfilgrastim (Neulasta®) for the management of chemotherapy-induced neutropenia. Semin Oncol 2003;4:24-30
  • Pedder SC. Pegylation of interferon alfa: structural and pharmacokinetic properties. Semin Liver Dis 2003;23:19-22
  • Brocchini S, Godwin A, Balan S, et al. Disulfide bridge based PEGylation of proteins. Adv Drug Deliv Rev 2008;60:3-12
  • Brocchini S, Balan S, Godwin A, et al. PEGylation of native disulfide bonds in proteins. Nat Protocols 2006;1:2241-52
  • Balan S, Choi JW, Godwin A, et al. Site-specific PEGylation of protein disulfide bonds using a three-carbon bridge. Bioconjug Chem 2007;18:61-76
  • Shaunak S, Godwin A, Choi JW, et al. Site-specific PEGylation of native disulfide bonds in therapeutic proteins. Nat Chem Biol 2006;2:312-3
  • Li XQ, Lei JD, Su ZG, et al. Comparison of bioactivities of monopegylated rhG-CSF with branched and linear mPEG. Process Biochem 2007;42:1625-31
  • Krinner EM, Hepp J, Hoffmann P, et al. A highly stable polyethylene glycol-conjugated human single-chain antibody neutralizing granulocyte-macrophage colony stimulating factor at low nanomolar concentration. Protein Eng Des Sel 2006;19:461-70
  • Zhao H, Yang K, Martinez A, et al. Linear and branched bicin linkers for releasable PEGylation of macromolecules: controlled release in vivo and in vitro from mono- and multi-PEGylated proteins. Bioconjug Chem 2006;17:341-51
  • Talpaz M, Rakhit A, Rittweger K, et al. Phase I evaluation of a 40-kDa branched-chain long-acting PEGylated IFN-alpha -2a with and without cytarabine in patients with chronic myelogenous leukemia. Clin Cancer Res 2005;11:6247-55
  • Schiavon O, Caliceti P, Ferruti P, et al. Therapeutic proteins: a comparison of chemical and biological properties of uricase conjugated to linear or branched poly(ethylene glycol) and poly(N-acryloylmorpholine). Farmaco 2000;55:264-9
  • Lecolley F, Tao L, Mantovani G, et al. A new approach to bioconjugates for proteins and peptides (“pegylation”) utilizing living radical polymerisation. Chem Commun 2004;18:2026-7
  • Kamigaito M, Ando T, Sawamoto M. Metal-catalyzed living radical polymerization. Chem Rev 2001;101:3689-746
  • Tao L, Mantovani G, Lecolley F, et al. Alpha-aldehyde terminally functional methacrylic polymers from living radical polymerization: application in protein conjugation “pegylation”. J Am Chem Soc 2004;126:13220-1
  • Mantovani G, Lecolley F, Tao L, et al. Design and synthesis of N-maleimido-functionalized hydrophilic polymers via copper-mediated living radical polymerization: a suitable alternative to PEGylation chemistry. J Am Chem Soc 2005;127:2966-73
  • Asayama S, Nogawa M, Takei Y, et al. Synthesis of novel polyampholyte comb-type copolymers consisting of a poly(L-lysine) backbone and hyaluronic acid side chains for a DNA carrier. Bioconjug Chem 1998;9:476-81
  • Filpula D, Zhao H. Releasable PEGylation of proteins with customized linkers. Adv Drug Deliv Rev 2008;60:29-49
  • Asayama S, Maruyama A, Cho CS, Akaike T. Design of comb-type polyamine copolymers for a novel pH-sensitive DNA carrier. Bioconjug Chem 1997;8:833-8
  • Srividhya M, Preethi S, Gnanamani A, Reddy BS. Sustained release of protein from poly(ethylene glycol) incorporated amphiphilic comb like polymers. Int J Pharm 2006;326:119-27
  • Heredia KL, Bontempo D, Ly T, et al. In situ preparation of protein-“Smart” polymer conjugates with retention of bioactivity. J Am Chem Soc 2005;127:16955-60
  • Bontempo D, Maynard HD. Streptavidin as a macroinitiator for polymerization: in situ protein-polymer conjugate formation. J Am Chem Soc 2005;127:6508-9
  • Le Droumaguet B, Mantovani G, Haddleton DM, et al. Formation of giant amphiphiles by post-functionalization of hydrophilic protein–polymer conjugates. J Mater Chem 2007;19:1916-22
  • Rang HP. Drug discovery and development. Elsevier 2006
  • Read ML, Logan A, Seymour LW. Barriers to gene delivery using synthetic vectors. Adv Genet 2005;53:19-46
  • Patton JS, Byron PR. Inhaling medicines: delivering drugs to the body through the lungs. Nat Rev 2007;6:67-74
  • Mack GS. Pfizer dumps Exubera. Nat Biotech 2007;25:1331-2
  • Muchmore DB, Silverman B, De La Pena A, et al. The AIR inhaled insulin system: system components and pharmacokinetic/glucodynamic data. Diabetes Technol Ther 2007;9:S41-7
  • Rosenstock J, Muchmore D, Swanson D, et al. AIR Inhaled Insulin System: a novel insulin-delivery system for patients with diabetes. Expert Rev Med Devices 2007;4:683-92
  • Odegard PS, Capoccia KL. Inhaled insulin: exubera. Ann Pharmacother 2005;39:843-53
  • Patton JS, Bukar JG, Eldon MA. Clinical pharmacokinetics and pharmacodynamics of inhaled insulin. Clin Pharmacokinet 2004;43:781-801
  • Barrett R. Post exubera: can new life be breathed back into inhaled insulin? Drug Deliv Rep 2008:19-21
  • Leach CL. Modifying the pulmonary absorption and retention of proteins through PEGylation. Respir Drug Deliv 2004;9:69-78
  • Niven RW, Whitcomb KL, Shaner L, et al. The pulmonary absorption of aerosolized and intratracheally instilled rhG-CSF and monoPEGylated rhG-CSF. Pharm Res 1995;12:1343-9
  • Garcia-Contreras L, Morcol T, Bell SJ, et al. Evaluation of novel particles as pulmonary delivery systems for insulin in rats. AAPS Pharm Sci 2003;5:E9
  • Anabousi S, Kleemann E, Bakowsky U, et al. Effect of PEGylation on the stability of liposomes during nebulisation and in lung surfactant. J Nanosci Nanotech 2006;6:3010-6
  • Anabousi S, Bakowsky U, Schneider M, et al. In vitro assessment of transferrin-conjugated liposomes as drug delivery systems for inhalation therapy of lung cancer. Eur J Pharm Sci 2006;29:367-74
  • Lee YH, Sinko PJ. Oral delivery of salmon calcitonin. Adv Drug Deliv Rev 2000;42:225-38
  • Lee WA, Ennis RD, Longenecker JP, et al. The bioavailability of intranasal salmon calcitonin in healthy volunteers with and without a permeation enhancer. Pharm Res 1994;11:747-50
  • McHorney CA, Schousboe JT, Cline RR, et al. The impact of osteoporosis medication beliefs and side-effect experiences on non-adherence to oral bisphosphonates. Curr Med Res Opin 2007;12:3137-52
  • Youn YS, Na DH, Lee KC. High-yield production of biologically active mono-PEGylated salmon calcitonin by site-specific PEGylation. J Control Rel 2007;117:371-9
  • Nicolas J, San Miguel V, Mantovani G, et al. Fluorescently tagged polymer bioconjugates from protein derived macroinitiators. Chem Commun (Camb) 2006;45:4697-9
  • Tomalia DA. A new class of polymers: starburst dendritic macromolecules. Polym J 1985;17:117-32
  • Tomalia DA, Esfand R. Dendrons, dendrimers and dendrigrafts. Chem Ind 1997;11:416-20
  • Svenson S, Tomalia DA. Dendrimers in biomedical applications, reflections on the field. Adv Drug Deliv Rev 2005;57:2106-29
  • Yang H, Lopina ST. Stealth dendrimers for antiarrhythmic quinidine delivery. J Mater Sci Mater Med 2007;18:2061-5
  • Kobayashi H, Kawamoto S, Jo SK, et al. Macromolecular MRI contrast agents with small dendrimers: pharmacokinetic differences between sizes and cores. Bioconjug Chem 2003;14:388-94
  • Chaltin P, Margineanu A, Marchand D, et al. Delivery of antisense oligonucleotides using cholesterol-modified sense dendrimers and cationic lipids. Bioconjug Chem 2005;16:827-36
  • Juliano RL. Intracellular delivery of oligonucleotide conjugates and dendrimer complexes. Ann NY Acad Sci 2006;1082:18-26
  • Kang H, DeLong R, Fisher MH, et al. Tat-conjugated PAMAM dendrimers as delivery agents for antisense and siRNA oligonucleotides. Pharm Res 2005;22:2099-106
  • Fu HL, Cheng SX, Zhang XZ, et al. Dendrimer/DNA complexes encapsulated in a water soluble polymer and supported on fast degrading star poly(dl-lactide) for localized gene delivery. J Control Rel 2007;124:181-8
  • Huang RQ, Qu YH, Ke WL, et al. Efficient gene delivery targeted to the brain using a transferrin-conjugated polyethyleneglycol-modified polyamidoamine dendrimer. FASEB J 2007;21:1117-25
  • Zhong H, He ZG, Li Z, et al. Studies on polyamidoamine dendrimers as efficient gene delivery vector. J Biomater Appl 2007: published on 10 July 2007, doi:10.1177/0885328207080005
  • Kolhatkar RB, Kitchens KM, Swaan PW, et al. Surface Acetylation of Polyamidoamine (PAMAM) dendrimers decreases cytotoxicity while maintaining membrane permeability. Bioconjug Chem 2007;18:2054-60
  • Najlah M, Freeman S, Attwood D, et al. In vitro evaluation of dendrimer prodrugs for oral drug delivery. Int J Pharm 2007;336:183-90
  • Bhadra D, Bhadra S, Jain S, et al. A PEGylated dendritic nanoparticulate carrier of fluorouracil. Int J Pharm 2003;257:111-24
  • Kojima C, Kono K, Maruyama K, et al. Synthesis of polyamidoamine dendrimers having poly(ethylene glycol) grafts and their ability to encapsulate anticancer drugs. Bioconjug Chem 2000;11:910-7
  • Paleos CM, Tsiourvas D, Sideratou Z. Molecular engineering of dendritic polymers and their application as drug and gene delivery systems. Mol Pharm 2007;4:169-88
  • Borm PJ, Muller-Schulte D. Nanoparticles in drug delivery and environmental exposure: same size, same risks? Nanomedicine 2006;1:235-49
  • Elsayed MM, Abdallah OY, Naggar VF, et al. Lipid vesicles for skin delivery of drugs: reviewing three decades of research. Int J Pharm 2007;332:1-16
  • Kazakov S, Levon K. Liposome-nanogel structures for future pharmaceutical applications. Curr Pharm Design 2006;12:4713-28
  • Minko T, Pakunlu RI, Wang Y, et al. New generation of liposomal drugs for cancer. Anti Cancer Agents Med Chem 2006;6:537-52
  • Nahar M, Dutta T, Murugesan S, et al. Functional polymeric nanoparticles: an efficient and promising tool for active delivery of bioactives. Crit Rev Ther Drug Carrier Syst 2006;23:259-318
  • Huang A, Kennel SJ, Huang L. Interactions of immunoliposomes with target cells. J Biol Chemistry 1983;258:14034-40
  • Straubinger RM, Hong K, Friend DS, et al. Endocytosis of liposomes and intracellular fate of encapsulated molecules: encounter with a low pH compartment after internalization in coated vesicles. Cell 1983;32:1069-79
  • Dijkstra J, Van Galen M, Scherphof GL. Effects of ammonium chloride and chloroquine on endocytic uptake of liposomes by Kupffer cells in vitro. Biochimica et Biophysica Acta 1984;804:58-67
  • Koukourakis MI, Koukouraki S, Giatromanolaki A, et al. Liposomal doxorubicin and conventionally fractionated radiotherapy in the treatment of locally advanced non-small-cell lung cancer and head and neck cancer. J Clin Oncol 1999;17:3512-21
  • Colbern GT, Dykes DJ, Engbers C, et al. Encapsulation of the topoisomerase I inhibitor GL147211C in pegylated (STEALTH) liposomes: pharmacokinetics and antitumor activity in HT29 colon tumor xenografts. Clin Cancer Res 1998;4:3077-82
  • Hatakeyama H, Akita H, Ishida E, et al. Tumor targeting of doxorubicin by anti-MT1-MMP antibody-modified PEG liposomes. Int J Pharm 2007;342:194-200
  • Han HD, Lee A, Hwang T, et al. Enhanced circulation time and antitumor activity of doxorubicin by comblike polymer-incorporated liposomes. J Control Rel 2007;120:161-8
  • Lasic D, Martin F. Stealth Liposomes (Pharmacology and Toxicology Series). CRC Press Boca Raton FL 1995
  • Douglas JL, Gustin JK, Dezube B, et al. Kaposi's sarcoma: a model of both malignancy and chronic inflammation. Panminerva Med 2007;49:119-38
  • Rowinsky EK, Donehower RC. Paclitaxel (taxol). N Eng J Med 1995;332:1004-14
  • Rowinsky EK, Wright M, Monsarrat B, et al. Clinical pharmacology and metabolism of Taxol (paclitaxel): update 1993. Ann Oncol 1994;5:S7-16
  • Aagaard L, Rossi JJ. RNAi therapeutics: principles, prospects and challenges. Adv Drug Deliv Rev 2007;59:75-86
  • Wasungu L, Hoekstra D. Cationic lipids, lipoplexes and intracellular delivery of genes. J Control Rel 2006;116:255-64
  • DeRouchey J, Schmidt C, Walker GF, et al. Monomolecular Assembly of siRNA and Poly(ethylene glycol)–Peptide Copolymers. Biomacromolecules 2008;9:724-32
  • Vandenbroucke RE, Lentacker I, Demeester J, et al. Ultrasound assisted siRNA delivery using PEG-siPlex loaded microbubbles. J Control Rel 2007: published online 14 Dec 2007, doi:10.1016
  • Graham ML. Pegaspargase: a review of clinical studies. Adv Drug Deliv Rev 2003;55:1293-302
  • Chakravarti VS, Borns P, Lobell J, et al. Chondroosseous dysplasia in severe combined immunodeficiency due to adenosine deaminase deficiency (chondroosseous dysplasia in ADA deficiency SCID). Pediatr Radiol 1991;21:447-8
  • Goffin V, Touraine P. Pegvisomant Pfizer/Sensus. Curr Opin Investig Drugs 2004;5:463-8
  • Regehly M, Greish K, Rancan F, et al. Water-soluble polymer conjugates of ZnPP for photodynamic tumor therapy. Bioconjug Chem 2007;18:494-9
  • Greenwald RB, Zhao H, Xia J, et al. Poly(ethylene glycol) prodrugs of the CDK inhibitor, alsterpaullone (NSC 705701): synthesis and pharmacokinetic studies. Bioconjug Chem 2004;15:1076-83
  • Reddy KR. Development and pharmacokinetics and pharmacodynamics of pegylated interferon alfa-2a (40 kD). Semin Liver Dis 2004;24:33-8
  • Bukowski RM, Tendler C, Cutler D, et al. Treating cancer with PEG Intron: pharmacokinetic profile and dosing guidelines for an improved interferon-alpha-2b formulation. Cancer 2002;95:389-96
  • Molineux G. The design and development of pegfilgrastim (PEG-rmetHuG-CSF, Neulasta). Curr Pharm Des 2004;10:1235-44
  • Moshfeghi AA, Puliafito CA. Pegaptanib sodium for the treatment of neovascular age-related macular degeneration. Expert Opin Invest Drugs 2005;14:671-82

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.