N-terminal α-amino group modification of antibodies using a site-selective click chemistry method

References

• Leavy O. Therapeutic antibodies: past, present and future. Nat Rev Immunol. 2010;10:297. doi:10.1038/nri2763. PMID:20422787.
   PubMed Web of Science ®Google Scholar
• Adler MJ, Dimitrov DS. Therapeutic antibodies against cancer. Hematol Oncol Clin North AMa. 2012;26:447–81. vii. doi:10.1016/j.hoc.2012.02.013. PMID:22520975.
   PubMed Web of Science ®Google Scholar
• Bakhtiar R. Antibody drug conjugates. Biotechnol lett. 2016;38:1655–64. doi:10.1007/s10529-016-2160-x. PMID:27334710. DOI.
   PubMed Web of Science ®Google Scholar
• Borcoman E, Le Tourneau C. Antibody drug conjugates: the future of chemotherapy? Curr Opin Oncol. 2016;28:429–36. doi:10.1097/CCO.0000000000000310. PMID:27366963.
   PubMed Web of Science ®Google Scholar
• Diamantis N, Banerji U. Antibody-drug conjugates–an emerging class of cancer treatment. Br J Cancer. 2016;114:362–7. doi:10.1038/bjc.2015.435. PMID:26742008.
   PubMed Web of Science ®Google Scholar
• Thomas A, Teicher BA, Hassan R. Antibody-drug conjugates for cancer therapy. Lancet Oncol. 2016;17:e254–62. doi:10.1016/S1470-2045(16)30030-4. PMID:27299281.
   PubMed Web of Science ®Google Scholar
• Boutureira O, Bernardes GJ. Advances in chemical protein modification. Chem Rev. 2015;115:2174–95. doi:10.1021/cr500399p. PMID:25700113.
   PubMed Web of Science ®Google Scholar
• Chudasama V, Maruani A, Caddick S. Recent advances in the construction of antibody-drug conjugates. Nat Chem. 2016;8:114–9. doi:10.1038/nchem.2467. PMID:26892562.
   PubMed Web of Science ®Google Scholar
• Hoffmann RM, Coumbe BGT, Josephs DH, Mele S, Ilieva KM, Cheung A, Tutt AN, Spicer JF, Thurston DE, Crescioli S, et al. Antibody structure and engineering considerations for the design and function of Antibody Drug Conjugates (ADCs). Oncoimmunology. 2018;7:e1395127. DOI:10.1080/2162402X.2017.1395127. PMID:29375935.
   PubMed Web of Science ®Google Scholar
• Peters C, Brown S. Antibody-drug conjugates as novel anti-cancer chemotherapeutics. Biosci Rep. 2015;35:e00225. doi:10.1042/BSR20150089. PMID:26182432.
   PubMed Web of Science ®Google Scholar
• Panowski S, Bhakta S, Raab H, Polakis P, Junutula JR. Site-specific antibody drug conjugates for cancer therapy. mAbs. 2014;6:34–45. PMID:24423619.
   PubMed Web of Science ®Google Scholar
• Junutula JR, Raab H, Clark S, Bhakta S, Leipold DD, Weir S, Chen Y, Simpson M, Tsai SP, Dennis MS, et al. Site-specific conjugation of a cytotoxic drug to an antibody improves the therapeutic index. Nat Biotechnol. 2008;26:925–32. doi:10.1038/nbt.1480. PMID:18641636.
   PubMed Web of Science ®Google Scholar
• Casi G, Huguenin-Dezot N, Zuberbuhler K, Scheuermann J, Neri D. Site-specific traceless coupling of potent cytotoxic drugs to recombinant antibodies for pharmacodelivery. J Am Chem Soc. 2012;134:5887–92. doi:10.1021/ja211589m. PMID:22394212.
   PubMed Web of Science ®Google Scholar
• Basle E, Joubert N, Pucheault M. Protein chemical modification on endogenous amino acids. Chem Biol. 2010;17:213–27. doi:10.1016/j.chembiol.2010.02.008. PMID:20338513.
   PubMed Web of Science ®Google Scholar
• Axup JY, Bajjuri KM, Ritland M, Hutchins BM, Kim CH, Kazane SA, Halder R, Forsyth JS, Santidrian AF, Stafin K, et al. Synthesis of site-specific antibody-drug conjugates using unnatural amino acids. Proc Natl Acad Sci U S A. 2012;109:16101–6. doi:10.1073/pnas.1211023109. PMID:22988081.
   PubMed Web of Science ®Google Scholar
• Zimmerman ES, Heibeck TH, Gill A, Li X, Murray CJ, Madlansacay MR, Tran C, Uter NT, Yin G, Rivers PJ, et al. Production of site-specific antibody-drug conjugates using optimized non-natural amino acids in a cell-free expression system. Bioconjug Chem. 2014;25:351–61. doi:10.1021/bc400490z. PMID:24437342.
   PubMed Web of Science ®Google Scholar
• Zhu Z, Ramakrishnan B, Li J, Wang Y, Feng Y, Prabakaran P, Colantonio S, Dyba MA, Qasba PK, Dimitrov DS. Site-specific antibody-drug conjugation through an engineered glycotransferase and a chemically reactive sugar. MAbs. 2014;6:1190–200. doi:10.4161/mabs.29889. PMID:25517304.
   PubMed Web of Science ®Google Scholar
• Zhou Q, Stefano JE, Manning C, Kyazike J, Chen B, Gianolio DA, Park A, Busch M, Bird J, Zheng X, et al. Site-specific antibody-drug conjugation through glycoengineering. Bioconjug Chem. 2014;25:510–20. doi:10.1021/bc400505q. PMID:24533768.
   PubMed Web of Science ®Google Scholar
• Jeger S, Zimmermann K, Blanc A, Grunberg J, Honer M, Hunziker P, Struthers H, Schibli R. Site-specific and stoichiometric modification of antibodies by bacterial transglutaminase. Angew Chem. 2010;49:9995–7. doi:10.1002/anie.201004243. PMID:21110357.
   PubMedGoogle Scholar
• Shen BQ, Xu K, Liu L, Raab H, Bhakta S, Kenrick M, Parsons-Reponte KL, Tien J, Yu SF, Mai E, et al. Conjugation site modulates the in vivo stability and therapeutic activity of antibody-drug conjugates. Nat Biotechnol. 2012;30:184–9. doi:10.1038/nbt.2108. PMID:22267010.
   PubMed Web of Science ®Google Scholar
• Stephanopoulos N, Francis MB. Choosing an effective protein bioconjugation strategy. Nat Chem Biol. 2011;7:876–84. doi:10.1038/nchembio.720. PMID:22086289.
   PubMed Web of Science ®Google Scholar
• Varland S, Osberg C, Arnesen T. N-terminal modifications of cellular proteins: The enzymes involved, their substrate specificities and biological effects. Proteomics. 2015;15:2385–401. doi:10.1002/pmic.201400619. PMID:25914051.
   PubMed Web of Science ®Google Scholar
• Chelius D, Shaler TA. Capture of peptides with N-terminal serine and threonine: a sequence-specific chemical method for Peptide mixture simplification. Bioconjug Chem. 2003;14:205–11. doi:10.1021/bc025605u. PMID:12526710.
   PubMed Web of Science ®Google Scholar
• Witus LS, Francis M. Site-Specific Protein Bioconjugation via a Pyridoxal 5′-Phosphate-Mediated N-Terminal Transamination Reaction. Curr Protoc Chem Biol. 2010;2:125–34. doi:10.1002/9780470559277.ch100018. PMID:23836553.
   PubMedGoogle Scholar
• Witus LS, Netirojjanakul C, Palla KS, Muehl EM, Weng CH, Iavarone AT, Francis MB. Site-specific protein transamination using N-methylpyridinium-4-carboxaldehyde. J Am Chem Soc. 2013;135:17223–9. doi:10.1021/ja408868a. PMID:24191658.
   PubMed Web of Science ®Google Scholar
• Obermeyer AC, Jarman JB, Francis MB. N-terminal modification of proteins with o-aminophenols. J Am Chem Soc. 2014;136:9572–9. doi:10.1021/ja500728c. PMID:24963951.
   PubMed Web of Science ®Google Scholar
• Chan AO, Ho CM, Chong HC, Leung YC, Huang JS, Wong MK, Che CM. Modification of N-terminal alpha-amino groups of peptides and proteins using ketenes. J Am Chem Soc. 2012;134:2589–98. doi:10.1021/ja208009r. PMID:22288779.
   PubMed Web of Science ®Google Scholar
• MacDonald JI, Munch HK, Moore T, Francis MB. One-step site-specific modification of native proteins with 2-pyridinecarboxyaldehydes. Nat Chem Biol. 2015;11:326–31. doi:10.1038/nchembio.1792. PMID:25822913.
   PubMed Web of Science ®Google Scholar
• Eliot AC, Kirsch JF. Pyridoxal phosphate enzymes: mechanistic, structural, and evolutionary considerations. Annu Rev Biochem. 2004;73:383–415. doi:10.1146/annurev.biochem.73.011303.074021. PMID:15189147.
   PubMed Web of Science ®Google Scholar
• Toney MD. Reaction specificity in pyridoxal phosphate enzymes. Arch Biochem Biophys. 2005;433:279–87. doi:10.1016/j.abb.2013.10.002. PMID:24121043.
   PubMed Web of Science ®Google Scholar
• Gilmore JM, Scheck RA, Esser-Kahn AP, Joshi NS, Francis MB. N-terminal protein modification through a biomimetic transamination reaction. Angewandte Chemie. 2006;45:5307–11. doi:10.1002/anie.200600368. PMID:16847857.
   PubMedGoogle Scholar
• Zhao Q, Ahmed M, Guo HF, Cheung IY, Cheung NK. Alteration of Electrostatic Surface Potential Enhances Affinity and Tumor Killing Properties of Anti-ganglioside GD2 Monoclonal Antibody hu3F8. J Biol Chem. 2015;290:13017–27. doi:10.1074/jbc.M115.650903. PMID:25851904.
   PubMed Web of Science ®Google Scholar
• Zhao Q, Feng Y, Zhu Z, Dimitrov DS. Human monoclonal antibody fragments binding to insulin-like growth factors I and II with picomolar affinity. Mol Cancer Ther. 2011;10:1677–85. doi:10.1158/1535-7163.MCT-11-0281. PMID:21750218.
   PubMed Web of Science ®Google Scholar
• Argmann CA, Auwerx J. Collection of blood and plasma from the mouse. Curr Protoc Mol Biol. 2006;Chapter 29:Unit 29A 3. doi:10.1002/0471142727.mb29a03s75. PMID:18265383.
   PubMedGoogle Scholar