Site-specific functionalization of proteins and their applications to therapeutic antibodies

Computational and Structural Biotechnology Journal

Volumn 9, Issue 14, 2014, Pages e201402001-

  Van Vught, Remko ^a   Pieters, Roland J ^b   Breukink, Eefjan ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Antibodies; Bioconjugation; Bioorthogonal chemistry; Protein labeling; Site specific modifications

Indexed keywords

EID: 84902211996     PISSN: None     EISSN: 20010370     Source Type: Journal    
DOI: 10.5936/csbj.201402001     Document Type: Short Survey

References (173)

1. Sélo I, Négroni L, Créminon C, Grassi J, Wal JM (1996) Preferential labeling of alpha-amino N-terminal groups in peptides by biotin: application to the detection of specific anti-peptide antibodies by enzyme immunoassays. J Immunol Methods 199:127-138. (Pubitemid 26412942)
2. Chen X, Muthoosamy K, Pfisterer A, Neumann B, Weil T (2012) Site-selective lysine modification of native proteins and peptides via kinetically controlled labeling. Bioconjug Chem 23:500-508.
3. Xu G, Shin SBY, Jaffrey SR (2011) Chemoenzymatic labeling of protein C-termini for positive selection of C-terminal peptides. ACS Chem Biol 6:1015-1020.
4. Kratz H, Haeckel A, Michel R, Schonzart L, Hanisch U, et al. (2012) Straightforward thiol-mediated protein labelling with DTPA: Synthesis of a highly active 111 In-annexin A5-DTPA tracer. EJNMMI Res 2:17.
5. Shen B-Q, Xu K, Liu L, Raab H, Bhakta S, et al. (2012) Conjugation site modulates the in vivo stability and therapeutic activity of antibody-drug conjugates. Nat Biotechnol 30:184-189.
6. Shaunak S, Godwin A, Choi J-W, Balan S, Pedone E, et al. (2006) Site-specific PEGylation of native disulfide bonds in therapeutic proteins. Nat Chem Biol 2:312-313. (Pubitemid 43787211)
7. Stadtman TC (1994) Emerging awareness of the critical roles of S-phosphocysteine and selenophosphate in biological systems. Biofactors 4:181-185. (Pubitemid 24182399)
8. Zhang FL, Casey PJ (1996) Protein prenylation: molecular mechanisms and functional consequences. Annu Rev Biochem 65:241-269. (Pubitemid 26250610)
9. Stepper J, Shastri S, Loo TS, Preston JC, Novak P, et al. (2011) Cysteine S-glycosylation, a new post-translational modification found in glycopeptide bacteriocins. FEBS Lett 585:645-650.
10. Chalker JM, Gunnoo SB, Boutureira O, Gerstberger SC, Fernandez-Gonzalez M, et al. (2011) Methods for converting cysteine to dehydroalanine on peptides and proteins. Chem Sci 2:1666.
11. Geoghegan KF, Stroh JG (n. d.) Site-directed conjugation of nonpeptide groups to peptides and proteins via periodate oxidation of a 2-amino alcohol. Application to modification at N-terminal serine. Bioconjug Chem 3:138-146.
12. Kung KK-Y, Wong K-F, Leung K-C, Wong M-K (2013) N-Terminal a-amino group modification of peptides by an oxime formation-exchange reaction sequence. Chem Commun (Camb) 49:6888-6890.
13. Temming RP, Eggermont L, van Eldijk MB, van Hest JCM, van Delft FL (2013) N-Terminal dual protein functionalization by strain-promoted alkyne-nitrone cycloaddition. Org Biomol Chem 11:2772-2779.
14. Dawson PE, Muir TW, Clark-Lewis I, Kent SB (1994) Synthesis of proteins by native chemical ligation. Science 266:776-779. (Pubitemid 24359280)
15. Ghosh I, Considine N, Maunus E, Sun L, Zhang A, et al. (2011) Site-specific protein labeling by intein-mediated protein ligation. Methods Mol Biol 705:87-107.
16. Schoffelen S, Van Eldijk MB, Rooijakkers B, Raijmakers R, Heck AJR, et al. (2011) Metal-free and pH-controlled introduction of azides in proteins. Chem Sci 2:701.
17. Gilmore JM, Scheck RA, Esser-Kahn AP, Joshi NS, Francis MB (2006) N-terminal protein modification through a biomimetic transamination reaction. Angew Chem Int Ed Engl 45:5307-5311. (Pubitemid 44289366)
18. Scheck RA, Dedeo MT, Iavarone AT, Francis MB (2008) Optimization of a biomimetic transamination reaction. J Am Chem Soc 130:11762-11770.
19. Witus LS, Netirojjanakul C, Palla KS, Muehl EM, Weng C-H, et al. (2013) Site-specific protein transamination using N-methylpyridinium-4-carboxaldehyde. J Am Chem Soc 135:17223-17229.
20. Chan AO-Y, Ho C-M, Chong H-C, Leung Y-C, Huang J-S, et al. (2012) Modification of N-terminal a-amino groups of peptides and proteins using ketenes. J Am Chem Soc 134:2589-2598.
21. COHEN GN, MUNIER R (1956) [Incorporation of structural analogues of amino acids in bacterial proteins]. Biochim Biophys Acta 21:592-593.
22. COWIE DB, COHEN GN, BOLTON ET, DE ROBICHON-SZULMAJSTER H (1959) Amino acid analog incorporation into bacterial proteins. Biochim Biophys Acta 34:39-46.
23. Van Hest JC, Tirrell DA (1998) Efficient introduction of alkene functionality into proteins in vivo. FEBS Lett 428:68-70. (Pubitemid 28266830)
24. Kiick KL, Saxon E, Tirrell DA, Bertozzi CR (2002) Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation. Proc Natl Acad Sci U S A 99:19-24. (Pubitemid 34060308)
25. Sletten EM, Bertozzi CR (2009) Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed Engl 48:6974-6998.
26. Schoffelen S, Lambermon MHL, van Eldijk MB, van Hest JCM (2008) Site-specific modification of Candida antarctica lipase B via residue-specific incorporation of a non-canonical amino acid. Bioconjug Chem 19:1127-1131. (Pubitemid 351874933)
27. Ibba M, Kast P, Hennecke H (1994) Substrate specificity is determined by amino acid binding pocket size in Escherichia coli phenylalanyl-tRNA synthetase. Biochemistry 33:7107-7112. (Pubitemid 24208747)
28. Ibba M, Hennecke H (1995) Relaxing the substrate specificity of an aminoacyl-tRNA synthetase allows in vitro and in vivo synthesis of proteins containing unnatural amino acids. FEBS Lett 364:272-275.
29. Tang Y, Tirrell DA (2002) Attenuation of the editing activity of the Escherichia coli leucyl-tRNA synthetase allows incorporation of novel amino acids into proteins in vivo. Biochemistry 41:10635-10645. (Pubitemid 34913323)
30. Kast P, Hennecke H (1991) Amino acid substrate specificity of Escherichia coli phenylalanyl-tRNA synthetase altered by distinct mutations. J Mol Biol 222:99-124. (Pubitemid 121003991)
31. Doring V, Mootz HD, Nangle LA, Hendrickson TL, de Crecy-Lagard V, et al. (2001) Enlarging the amino acid set of Escherichia coli by infiltration of the valine coding pathway. Science 292:501-504. (Pubitemid 32335952)
32. Noren CJ, Anthony-Cahill SJ, Griffith MC, Schultz PG (1989) A general method for site-specific incorporation of unnatural amino acids into proteins. Science 244:182-188.
33. Bain JD, Diala ES, Glabe CG, Dix TA, Chamberlin AR (1989) Biosynthetic site-specific incorporation of a non-natural amino acid into a polypeptide. J Am Chem Soc 111:8013-8014.
34. Nowak M, Kearney P, Saks M, Labarca C, Silverman S, et al. (1995) Nicotinic receptor binding site probed with unnatural amino acid incorporation in intact cells. Science (80-) 268:439-442.
35. Liu DR, Schultz PG (1999) Progress toward the evolution of an organism with an expanded genetic code. Proc Natl Acad Sci 96:4780-4785. (Pubitemid 29214488)
36. Young TS, Ahmad I, Yin JA, Schultz PG (2010) An enhanced system for unnatural amino acid mutagenesis in E. coli. J Mol Biol 395:361-374.
37. Liu CC, Schultz PG (2010) Adding New Chemistries to the Genetic Code. Annu Rev Biochem 79:413-444.
38. Hohsaka T, Ashizuka Y, Murakami H, Sisido M (1996) Incorporation of Nonnatural Amino Acids into Streptavidin through In Vitro Frame-Shift Suppression. J Am Chem Soc 118:9778-9779. (Pubitemid 26358340)
39. Rodriguez EA, Lester HA, Dougherty DA (2006) In vivo incorporation of multiple unnatural amino acids through nonsense and frameshift suppression. Proc Natl Acad Sci U S A 103:8650-8655. (Pubitemid 43878075)
40. Karve TM, Cheema AK (2011) Small Changes Huge Impact: The Role of Protein Posttranslational Modifications in Cellular Homeostasis and Disease. J Amino Acids 2011:1-13.
41. Resh MD (2006) Trafficking and signaling by fatty-acylated and prenylated proteins. Nat Chem Biol 2:584-590. (Pubitemid 44610342)
42. Casey PJ, Seabra MC (1996) Protein prenyltransferases. J Biol Chem 271:5289-5292. (Pubitemid 26083855)
43. van't Hof W, Resh MD (1999) Dual fatty acylation of p59 (Fyn) is required for association with the T cell receptor zeta chain through phosphotyrosine-Src homology domain-2 interactions. J Cell Biol 145:377-389. (Pubitemid 29198308)
44. Heal WP, Wickramasinghe SR, Leatherbarrow RJ, Tate EW (2008) N-Myristoyl transferase-mediated protein labelling in vivo. Org Biomol Chem 6:2308-2315. (Pubitemid 351852834)
45. Kho Y, Kim SC, Jiang C, Barma D, Kwon SW, et al. (2004) A tagging-via-substrate technology for detection and proteomics of farnesylated proteins. Proc Natl Acad Sci U S A 101:12479-12484. (Pubitemid 39122049)
46. Greenberg CS, Birckbichler PJ, Rice RH (1991) Transglutaminases: multifunctional cross-linking enzymes that stabilize tissues. FASEB J 5:3071-3077. (Pubitemid 21892867)
47. Lee J-H, Song C, Kim D-H, Park I-H, Lee S-G, et al. (2013) Glutamine (Q)-peptide screening for transglutaminase reaction using mRNA display. Biotechnol Bioeng 110:353-362.
48. Lin C-W, Ting AY (2006) Transglutaminase-catalyzed site-specific conjugation of small-molecule probes to proteins in vitro and on the surface of living cells. J Am Chem Soc 128:4542-4543.
49. Carrico IS, Carlson BL, Bertozzi CR (2007) Introducing genetically encoded aldehydes into proteins. Nat Chem Biol 3:321-322. (Pubitemid 46789266)
50. Wu P, Shui W, Carlson BL, Hu N, Rabuka D, et al. (2009) Sitespecific chemical modification of recombinant proteins produced in mammalian cells by using the genetically encoded aldehyde tag. Proc Natl Acad Sci U S A 106:3000-3005.
51. Rabuka D, Rush JS, Dehart GW, Wu P, Bertozzi CR (2012) Sitespecific chemical protein conjugation using genetically encoded aldehyde tags. Nat Protoc 7:1052-1067.
52. Keppler A, Gendreizig S, Gronemeyer T, Pick H, Vogel H, et al. (2003) A general method for the covalent labeling of fusion proteins with small molecules in vivo. Nat Biotechnol 21:86-89. (Pubitemid 36055833)
53. Mannesse ML, Boots JW, Dijkman R, Slotboom AJ, van der Hijden HT, et al. (1995) Phosphonate analogues of triacylglycerols are potent inhibitors of lipase. Biochim Biophys Acta 1259:56-64.
54. Pries F, Kingma J, Krooshof GH, Jeronimus-Stratingh CM, Bruins AP, et al. (1995) Histidine 289 is essential for hydrolysis of the alkyl-enzyme intermediate of haloalkane dehalogenase. J Biol Chem 270:10405-10411.
55. Gronemeyer T, Chidley C, Juillerat A, Heinis C, Johnsson K (2006) Directed evolution of 06-alkylguanine-DNA alkyltransferase for applications in protein labeling. Protein Eng DesSel 19:309-316. (Pubitemid 43999641)
56. Bonasio R Carman C V, Kim E, Sage PT, Love KR, et al. (2007) Specific and covalent labeling of a membrane protein with organic fiuorochromes and quantum dots. Proc Natl Acad Sci U S A 104:14753-14758. (Pubitemid 350003215)
57. Los G V, Wood K (2007) The HaloTag: a novel technology for cell imaging and protein analysis. Methods Mol Biol 356:195-208.
58. Gautier A, Juillerat A, Heinis C, Correa IR, Kindermann M, et al. (2008) An engineered protein tag for multiprotein labeling in living cells. Chem Biol 15:128-136. (Pubitemid 351253620)
59. Chen I, Howarth M, Lin W, Ting AY (2005) Site-specific labeling of cell surface proteins with biophysical probes using biotin ligase. Nat Methods 2:99-104. (Pubitemid 41131030)
60. Fernandez-Suarez M, Baruah H, Martinez-Hernandez L, Xie KT, Baskin JM, et al. (2007) Redirecting lipoic acid ligase for cell surface protein labeling with small-molecule probes. Nat Biotechnol 25:1483-1487. (Pubitemid 350233135)
61. Yao JZ, Uttamapinant C, Poloukhtine A, Baskin JM, Codelli JA, et al. (2012) Fluorophore targeting to cellular proteins via enzymemediated azide ligation and strain-promoted cycloaddition. J Am Chem Soc 134:3720-3728.
62. Baruah H, Puthenveetil S, Choi Y-A, Shah S, Ting AY (2008) An engineered aryl azide ligase for site-specific mapping of proteinprotein interactions through photo-cross-linking. Angew Chem Int Ed Engl 47:7018-7021.
63. Cohen JD, Thompson S, Ting AY (2011) Structure-guided engineering of a Pacific Blue fluorophore ligase for specific protein imaging in living cells. Biochemistry 50:8221-8225.
64. Liu DS, Tangpeerachaikul A, Selvaraj R, Taylor MT, Fox JM, et al. (2012) Diels-Alder cycloaddition for fluorophore targeting to specific proteins inside living cells. J Am Chem Soc 134:792-795.
65. Lambalot RH, Gehring AM, Flugel RS, Zuber P, La Celle M, et al. (1996) A new enzyme superfamily - the phosphopantetheinyl transferases. Chem Biol 3:923-936. (Pubitemid 27017091)
66. Lambalot RH, Walsh CT (1995) Cloning, overproduction, and characterization of the Escherichia coli holo-acyl carrier protein synthase. J Biol Chem 270:24658-24661.
67. Fichtlscherer F, Wellein C, Mittag M, Schweizer E (2000) A novel function of yeast fatty acid synthase. Eur J Biochem 267:2666-2671.
68. Yin J, Liu F, Schinke M, Daly C, Walsh CT (2004) Phagemid encoded small molecules for high throughput screening of chemical libraries. J Am Chem Soc 126:13570-13571. (Pubitemid 39407209)
69. Yin J, Straight PD, McLoughlin SM, Zhou Z, Lin AJ, et al. (2005) Genetically encoded short peptide tag for versatile protein labeling by Sfp phosphopantetheinyl transferase. Proc Natl Acad Sci U S A 102:15815-15820. (Pubitemid 41552825)
70. Zhou Z, Cironi P, Lin AJ, Xu Y, Hrvatin S, et al. (2007) Genetically encoded short peptide tags for orthogonal protein labeling by Sfp and AcpS phosphopantetheinyl transferases. ACS Chem Biol 2:337-346. (Pubitemid 350001582)
71. Mazmanian SK, Liu G, Ton-That H, Schneewind O (1999) Staphylococcus aureus sortase, an enzyme that anchors surface proteins to the cell wall. Science 285:760-763.
72. Marraffini LA, Dedent AC, Schneewind O (2006) Sortases and the art of anchoring proteins to the envelopes of gram-positive bacteria. Microbiol Mol Biol Rev 70:192-221.
73. Popp MW-L, Ploegh HL (2011) Making and breaking peptide bonds: protein engineering using sortase. Angew Chemie Int Ed 50:5024-5032.
74. Popp MW, Artavanis-Tsakonas K, Ploegh HL (2009) Substrate filtering by the active site crossover loop in UCHL3 revealed by sortagging and gain-of-function mutations. J Biol Chem 284:3593-3602.
75. Antos JM, Chew G-L, Guimaraes CP, Yoder NC, Grotenbreg GM, et al. (2009) Site-specific N- and C-terminal labeling of a single polypeptide using sortases of different specificity. J Am Chem Soc 131:10800-10801.
76. Antos JM, Popp MW-L, Ernst R, Chew G-L, Spooner E, et al. (2009) A straight path to circular proteins. J Biol Chem 284:16028-16036.
77. Wu Z, Guo X, Guo Z (2011) Sortase A-catalyzed peptide cyclization for the synthesis of macrocyclic peptides and glycopeptides. Chem Commun 47:9218-9220.
78. Popp MW, Dougan SK, Chuang T-Y, Spooner E, Ploegh HL (2011) Sortase-catalyzed transformations that improve the properties of cytokines. Proc Natl Acad Sci USA 108:3169-3174.
79. Levary DA, Parthasarathy R, Boder ET, Ackerman ME (2011) Protein-Protein Fusion Catalyzed by Sortase A. PLoS One 6:6.
80. Chen I, Dorr BM, Liu DR (2011) A general strategy for the evolution of bond-forming enzymes using yeast display. Proc Natl Acad Sci U S A 108:11399-11404.
81. Perler FB, Davis EO, Dean GE, Gimble FS, Jack WE, et al. (1994) Protein splicing elements: inteins and exteins - a definition of terms and recommended nomenclature. Nucleic Acids Res 22:1125-1127. (Pubitemid 24162112)
82. Xu MQ, Evans TC (2001) Intein-mediated ligation and cyclization of expressed proteins. Methods 24:257-277.
83. Mohlmann S, Bringmann P, Greven S, Harrenga A (2011) Sitespecific modification of ED-B-targeting antibody using inteinfusion technology. BMC Biotechnol 11:76.
84. Wood RJ, Pascoe DD, Brown ZK, Medlicott EM, Kriek M, et al. (n. d.) Optimized conjugation of a fluorescent label to proteins via intein-mediated activation and ligation. Bioconjug Chem 15:366-372.
85. Gottlieb D, Grunwald C, Nowak C, Kuhlmann J, Waldmann H (2006) Intein-mediated in vitro synthesis of lipidated Ras proteins. Chem Commun: 260-262.
86. Reulen SWA, van Baal I, Raats JMH, Merkx M (2009) Efficient, chemoselective synthesis of immunomicelles using single-domain antibodies with a C-terminal thioester. BMC Biotechnol 9:66.
87. Muir TW, Sondhi D, Cole PA (1998) Expressed protein ligation: a general method for protein engineering. Proc Natl Acad Sci U S A 95:6705-6710. (Pubitemid 28278044)
88. Girish A, Sun H, Yeo DSY, Chen GYJ, Chua T-K, et al. (2005) Site-specific immobilization of proteins in a microarray using intein-mediated protein splicing. Bioorg Med Chem Lett 15:2447-2451. (Pubitemid 40614968)
89. Yeo DSY, Srinivasan R, Uttamchandani M, Chen GYJ, Zhu Q, et al. (2003) Cell-permeable small molecule probes for site-specific labeling of proteins. Chem Commun: 2870-2871. (Pubitemid 37485412)
90. Southworth MW, Amaya K, Evans TC, Xu MQ, Perler FB (1999) Purification of proteins fused to either the amino or carboxy terminus of the Mycobacterium xenopi gyrase A intein. Biotechniques 27:110-114, 116, 118-120.
91. Bracher PJ, Snyder PW, Bohall BR, Whitesides GM (2011) The relative rates of thiol-thioester exchange and hydrolysis for alkyl and aryl thioalkanoates in water. Orig Life Evol Biosph 41:399-412.
92. Walsh G, Jefferis R (2006) Post-translational modifications in the context of therapeutic proteins. Nat Biotechnol 24:1241-1252. (Pubitemid 44564769)
93. Spiro RG (2002) Protein glycosylation: nature, distribution, enzymatic formation, and disease implications of glycopeptide bonds. Glycobiology 12:43R-56R. (Pubitemid 34760066)
94. Comer FI, Hart GW (2000) O-Glycosylation of Nuclear and Cytosolic Proteins: DYNAMIC INTERPLAY BETWEEN O-GlcNAc ANDO-PHOSPHATE. J Biol Chem 275:29179-29182. (Pubitemid 32043784)
95. Sola RJ, Griebenow K (2009) Effects of glycosylation on the stability of protein pharmaceuticals. J Pharm Sci 98:1223-1245.
96. Saxon E, Bertozzi CR (2000) Cell surface engineering by a modified Staudinger reaction. Science 287:2007-2010. (Pubitemid 30158675)
97. Laughlin ST, Bertozzi CR (2007) Metabolic labeling of glycans with azido sugars and subsequent glycan-profiling and visualization via Staudinger ligation. Nat Protoc 2:2930-2944.
98. Clark PM, Dweck JF, Mason DE, Hart CR, Buck SB, et al. (2008) Direct in-gel fluorescence detection and cellular imaging of O-GlcNAc-modified proteins. J Am Chem Soc 130:11576-11577.
99. Robert Aggeler JBQLBA (2012) Site-specific Labeling of Antibody N-glycans using a Click Chemistry-mediated Chemoenzymatic Approach. J Biomol Tech 23:S28.
100. Zhang X-L (2006) Roles of glycans and glycopeptides in immune system and immune-related diseases. Curr Med Chem 13:1 Hill 47.
101. Newman DJ, Cragg GM (2007) Natural products as sources of new drugs over the last 25 years. J Nat Prod 70:461-477. (Pubitemid 46595760)
102. Leader B, Baca QJ, Golan DE (2008) Protein therapeutics: a summary and pharmacological classification. Nat Rev Drug Discov 7:21-39.
103. Brown LR (2005) Commercial challenges of protein drug delivery. Expert Opin Drug Deliv 2:29-42. (Pubitemid 40123881)
104. Morishita M, Peppas NA (2006) Is the oral route possible for peptide and protein drug delivery? Drug Discov Today 11:905-910. (Pubitemid 44403178)
105. Jenkins N (2007) Modifications of therapeutic proteins: challenges and prospects. Cytotechnology 53:121-125. (Pubitemid 46944878)
106. Brater DC (2002) Measurement of renal function during drug development. Br J Clin Pharmacol 54:87-95. (Pubitemid 36124761)
107. Harmsen MM, De Haard HJ (2007) Properties, production, and applications of camelid single-domain antibody fragments. Appl Microbiol Biotechnol 77:13-22. (Pubitemid 47573319)
108. Flanagan RJ, Jones AL (2004) Fab antibody fragments: some applications in clinical toxicology. Drug Saf an Int J Med Toxicol drug Exp 27:1115-1133. (Pubitemid 39647853)
109. Sola RJ, Griebenow K (2010) Glycosylation of therapeutic proteins: an effective strategy to optimize efficacy. BioDrugs Clin Immunother Biopharm gene Ther 24:9-21.
110. Baker K, Rath T, Blumberg R (2013) Regulation of Immunological Responses by the Neonatal Fc Receptor for IgG, FcRn. In: Nimmerjahn F, editor. Molecular and Cellular Mechanisms of Antibody Activity SE - 8. Springer New York. pp. 189-219.
111. Veronese FM, Mero A (2008) The impact of PEGylation on biological therapies. BioDrugs Clin Immunother Biopharm gene Ther 22:315-329.
112. Veronese FM, Caliceti P, Schiavon O (1997) Branched and Linear Poly (Ethylene Glycol): Influence of the Polymer Structure on Enzymological, Pharmacokinetic, and Immunological Properties of Protein Conjugates. J Bioact Compat Polym 12:196-207. (Pubitemid 27470395)
113. Leong SR De Forge L, Presta L, Gonzalez T, Fan A, et al. (2001) Adapting pharmacokinetic properties of a humanized antiinterleukin-8 antibody for therapeutic applications using sitespecific pegylation. Cytokine 16:106-119. (Pubitemid 34081705)
114. Vugmeyster Y, Entrican CA, Joyce AP, Lawrence-Henderson RF, Leary BA, et al. (2012) Pharmacokinetic, biodistribution, and biophysical profiles of TNF nanobodies conjugated to linear or branched poly (ethylene glycol). Bioconjug Chem 23:1452-1462.
115. Richter AW, Akerblom E (1983) Antibodies against polyethylene glycol produced in animals by immunization with monomethoxy polyethylene glycol modified proteins. Int Arch Allergy Appl Immunol 70:124-131. (Pubitemid 13171427)
116. Armstrong JK, Hempel G, Koling S, Chan LS, Fisher T, et al. (2007) Antibody against poly (ethylene glycol) adversely affects PEG-asparaginase therapy in acute lymphoblastic leukemia patients. Cancer 110:103-111. (Pubitemid 46986423)
117. Ganson NJ, Kelly SJ, Scarlett E, Sundy JS, Hershfield MS (2006) Control of hyperuricemia in subjects with refractory gout, and induction of antibody against poly (ethylene glycol) (PEG), in a phase I trial of subcutaneous PEGylated urate oxidase. Arthritis Res Ther 8.
118. Knop K, Hoogenboom R Fischer D, Schubert US (2010) Poly (ethylene glycol) in drug delivery: pros and cons as well as potential alternatives. Angew Chem Int Ed Engl 49:6288-6308.
119. Jefferis R Pound J, Lund J, Goodall M (1994) Effector mechanisms activated by human IgG subclass antibodies: clinical and molecular aspects. Review article. Ann Biol Clin (Paris) 52:57-65. (Pubitemid 24086446)
120. Jefferis R (2009) Recombinant antibody therapeutics: the impact of glycosylation on mechanisms of action. Trends Pharmacol Sci 30:356-362.
121. Nesbitt A, Fossati G, Bergin M, Stephens P, Stephens S, et al. (2007) Mechanism of action of certolizumab pegol (CDP870): in vitro comparison with other anti-tumor necrosis factor alpha agents. Inflamm Bowel Dis 13:1323-1332. (Pubitemid 350206841)
122. Jiang X-R, Song A, Bergelson S, Arroll T, Parekh B, et al. (2011) Advances in the assessment and control of the effector functions of therapeutic antibodies. Nat Rev Drug Discov 10:101-111.
123. Pedley RB, Boden JA, Boden R, Begem RH, Turner A, et al. (1994) The potential for enhanced tumour localisation by poly (ethylene glycol) modification of anti-CEA antibody. Br J Cancer 70:1126-1130. (Pubitemid 24358949)
124. Di Paolo A, Bocci G (2007) Drug distribution in tumors: mechanisms, role in drug resistance, and methods for modification. Curr Oncol Rep 9:109-114. (Pubitemid 46332382)
125. Klein A V, Hambley TW (2009) Platinum drug distribution in cancer cells and tumors. Chem Rev 109:4911-4920.
126. Thurber GM, Schmidt MM, Wittrup KD (2008) Factors determining antibody distribution in tumors. Trends Pharmacol Sci 29:57-61.
127. Fujimori K, Covell DG, Fletcher JE, Weinstein JN (1989) Modeling analysis of the global and microscopic distribution of immunoglobulin G, F (ab') 2, and Fab in tumors. Cancer Res 49:5656-5663. (Pubitemid 19256448)
128. Saga T, Neumann RD, Heya T, Sato J, Kinuya S, et al. (1995) Targeting cancer micrometastases with monoclonal antibodies: a binding-site barrier. Proc Natl Acad Sci U S A 92:8999-9003.
129. Rudnick SI, Adams GP (2009) Affinity and avidity in antibodybased tumor targeting. Cancer Biother Radiopharm 24:155-161.
130. Roopenian DC, Akilesh S (2007) FcRn: the neonatal Fc receptor comes of age. Nat Rev Immunol 7:715-725. (Pubitemid 47327396)
131. Ghetie V, Hubbard JG, Kim JK, Tsen MF, Lee Y, et al. (1996) Abnormally short serum half-lives of IgG in beta 2-microglobulindeficient mice. Eur J Immunol 26:690-696. (Pubitemid 26091401)
132. Junghans RP, Anderson CL (1996) The protection receptor for IgG catabolism is the beta2-microglobulin-containing neonatal intestinal transport receptor. Proc Natl Acad Sci U S A 93:5512-5516.
133. Israel EJ, Wilsker DF, Hayes KC, Schoenfeld D, Simister NE (1996) Increased clearance of IgG in mice that lack beta 2-microglobulin: possible protective role of FcRn. Immunology 89:573-578. (Pubitemid 26419660)
134. Datta-Mannan A, Witcher DR, Lu J, Wroblewski VJ (2012) Influence of improved FcRn binding on the subcutaneous bioavailability of monoclonal antibodies in cynomolgus monkeys. MAbs 4.
135. Vugmeyster Y, Xu X, Theil F-P, Khawli LA, Leach MW (2012) Pharmacokinetics and toxicology of therapeutic proteins: Advances and challenges. World J Biol Chem 3:73-92.
136. Casi G, Neri D (2012) Antibody-drug conjugates: basic concepts, examples and future perspectives. J Control Release 161:422-428.
137. Dosio F, Brusa P, Cattel L (2011) Immunotoxins and anticancer drug conjugate assemblies: the role of the linkage between components. Toxins (Basel) 3:848-883.
138. Chari RVJ (2008) Targeted cancer therapy: conferring specificity to cytotoxic drugs. Ace Chem Res 41:98-107.
139. Hudis CA (2007) Trastuzumab-mechanism of action and use in clinical practice. N Engl J Med 357:39-51. (Pubitemid 47026733)
140. Lewis Phillips GD, Li G, Dugger DL, Crocker LM, Parsons KL, et al. (2008) Targeting HER2-positive breast cancer with trastuzumab-DM 1, an antibody-cytotoxic drug conjugate. Cancer Res 68:9280-9290.
141. Hurvitz SA, Dirix L, Kocsis J, Bianchi G V, Lu J, et al. (2013) Phase II randomized study of trastuzumab emtansine versus trastuzumab plus docetaxel in patients with human epidermal growth factor receptor 2-positive metastatic breast cancer. J Clin Oncol 31:1157-1163.
142. Girish S, Gupta M, Wang B, Lu D, Krop IE, et al. (2012) Clinical pharmacology of trastuzumab emtansine (T-DM1): an antibodydrug conjugate in development for the treatment of HER2-positive cancer. Cancer Chemother Pharmacol 69:1229-1240.
143. Francisco JA, Cerveny CG, Meyer DL, Mixan BJ, Klussman K, et al. (2003) cAClO-vcMMAE, an anti-CD30-monomethyl auristatin E conjugate with potent and selective antitumor activity. Blood 102:1458-1465. (Pubitemid 36988057)
144. Hamblett KJ, Senter PD, Chace DF, Sun MMC, Lenox J, et al. (2004) Effects of drug loading on the antitumor activity of a monoclonal antibody drug conjugate. Clin Cancer Res 10:7063-7070. (Pubitemid 39383058)
145. Kim CH, Axup JY, Dubrovska A, Kazane SA, Hutchins BA, et al. (2012) Synthesis of bispecific antibodies using genetically encoded unnatural amino acids. J Am Chem Soc 134:9918-9921.
146. Axup JY, Bajjuri KM, Ritland M, Hutchins BM, Kim CH, et al. (2012) Synthesis of site-specific antibody-drug conjugates using unnatural amino acids. Proc Natl Acad Sci U S A 109:16101-16106.
147. Kazane SA, Axup JY, Kim CH, Ciobanu M, Wold ED, et al. (2013) Self-assembled antibody multimers through peptide nucleic acid conjugation. J Am Chem Soc 135:340-346.
148. Dowell JA, Korth-Bradley J, Liu H, King SP, Berger MS (2001) Pharmacokinetics of gemtuzumab ozogamicin, an antibodytargeted chemotherapy agent for the treatment of patients with acute myeloid leukemia in first relapse. J Clin Pharmacol. 41(11):1206-14. (Pubitemid 32983219)
149. Chames P, Baty D (n. d.) Bispecific antibodies for cancer therapy: the light at the end of the tunnel? MAbs 1:539-547.
150. Staerz UD, Kanagawa O, Bevan MJ (n. d.) Hybrid antibodies can target sites for attack by T cells. Nature 314:628-631.
151. Karpovsky B, Titus JA, Stephany DA, Segal DM (1984) Production of target-specific effector cells using hetero-cross-linked aggregates containing anti-target cell and anti-Fc gamma receptor antibodies. J Exp Med 160:1686-1701. (Pubitemid 15193997)
152. Perez P, Hoffman RW, Shaw S, Bluestone JA, Segal DM (n. d.) Specific targeting of cytotoxic T cells by anti-T3 linked to antitarget cell antibody. Nature 316:354-356.
153. Reusch U, Sundaram M, Davol PA, Olson SD, Davis JB, et al. (2006) Anti-CD3 x anti-epidermal growth factor receptor (EGFR) bispecific antibody redirects T-cell cytolytic activity to EGFR-positive cancers in vitro and in an animal model. Clin Cancer Res 12:183-190. (Pubitemid 43166193)
154. Shalaby MR, Shepard HM, Presta L, Rodrigues ML, Beverley PC, et al. (1992) Development of humanized bispecific antibodies reactive with cytotoxic lymphocytes and tumor cells overexpressing the HER2 protooncogene. J Exp Med 175:217-225.
155. Spiess C, Merchant M, Huang A, Zheng Z, Yang N-Y, et al. (2013) Bispecific antibodies with natural architecture produced by co-culture of bacteria expressing two distinct half-antibodies. Nat Biotechnol 31:753-758.
156. Shen J, Zhu Z (2008) Catumaxomab, a rat/murine hybrid trifunctional bispecific monoclonal antibody for the treatment of cancer. Curr Opin Mol Ther 10:273-284. (Pubitemid 351799279)
157. Lindhofer H, Mocikat R, Steipe B, Thierfelder S (1995) Preferential species-restricted heavy/light chain pairing in rat/mouse quadromas. Implications for a single-step purification of bispecific antibodies. J Immunol 155:219-225.
158. Linke R, Klein A, Seimetz D (n. d.) Catumaxomab: clinical development and future directions. MAbs 2:129-136.
159. Martinelli E, De Palma R, Orditura M, De Vita F, Ciardiello F (2009) Anti-epidermal growth factor receptor monoclonal antibodies in cancer therapy. Clin Exp Immunol 158:1-9.
160. Hutchins BM, Kazane SA, Staflin K, Forsyth JS, Felding-Habermann B, et al. (2011) Site-specific coupling and sterically controlled formation of multimeric antibody fab fragments with unnatural amino acids. J Mol Biol 406:595-603.
161. Dykman LA, Khlebtsov NG (2011) Gold nanoparticles in biology and medicine: recent advances and prospects. Acta Naturae 3:34-55.
162. Kontermann RE (2006) Immunoliposomes for cancer therapy. Curr Opin Mol Ther 8:39-45. (Pubitemid 43230899)
163. Meng F, Engbers GHM, Feijen J (2005) Biodegradable polymersomes as a basis for artificial cells: encapsulation, release and targeting. J Control Release 101:187-198. (Pubitemid 39600982)
164. Lin JJ, Ghoroghchian PP, Zhang Y, Hammer DA (2006) Adhesion of antibody-functionalized polymersomes. Langmuir Acs J Surfaces Colloids 22:3975-3979.
165. Lee JS, Groothuis T, Cusan C, Mink D, Feijen J (2011) Lysosomally cleavable peptide-containing polymersomes modified with anti-EGFR antibody for systemic cancer chemotherapy. Biomaterials 32:9144-9153.
166. Debets MF, Leenders WPJ, Verrijp K, Zonjee M, Meeuwissen SA, et al. (2013) Nanobody-Functionalized Polymersomes for Tumor-Vessel Targeting. Macromol Biosci. 13(7):938-945.
167. Fang J, Nakamura H, Maeda H (2011) The EPR effect: Unique features of tumor blood vessels for drug delivery, factors involved, and limitations and augmentation of the effect. Adv Drug Deliv Rev 63:136-151.
168. Albanese A, Tang PS, Chan WCW (2012) The effect of nanoparticle size, shape, and surface chemistry on biological systems. Annu Rev Biomed Eng 14:1-16.
169. MacDiarmid JA, Mugridge NB, Weiss JC, Phillips L, Burn AL, et al. (2007) Bacterially derived 400 nm particles for encapsulation and cancer cell targeting of chemotherapeutics. Cancer Cell 11:431-445. (Pubitemid 46670079)
170. Senzer N, Nemunaitis J, Nemunaitis D, Bedell C, Edelman G, et al. (2013) Phase I Study of a Systemically Delivered p53 Nanoparticle in Advanced Solid
171. Wickham T, Futch K (2012) A Phase I Study of MM-302, a HER2-targeted Liposomal Doxorubicin. Patients with Adv HER2-Positive Breast Cancer Cancer Res 72:P5-18.
172. Mamot C, Ritschard R, Wicki A, Stehle G, Dieterle T, et al. (2012) Tolerability, safety, pharmacokinetics, and efficacy of doxorubicin-loaded anti-EGFR immunoliposomes in advanced solid tumours: a phase 1 dose-escalation study. Lancet Oncol 13:1234-1241.
173. Matsumura Y, Gotoh M, Muro K, Yamada Y, Shirao K, et al. (2004) Phase I and pharmacokinetic study of MCC-465, a doxorubicin (DXR) encapsulated in PEG immunoliposome, in patients with metastatic stomach cancer. Ann Oncol 15:517-525. (Pubitemid 38444560)