Methods for site-specific drug conjugation to antibodies

References

• Chabner BA, Roberts TG Jr.. Timeline: Chemotherapy and the war on cancer. Nat Rev Cancer 2005; 5:65 - 72; http://dx.doi.org/10.1038/nrc1529; PMID: 15630416
   PubMed Web of Science ®Google Scholar
• Minchinton AI, Tannock IF. Drug penetration in solid tumours. Nat Rev Cancer 2006; 6:583 - 92; http://dx.doi.org/10.1038/nrc1893; PMID: 16862189
   PubMed Web of Science ®Google Scholar
• Wu AM, Senter PD. Arming antibodies: prospects and challenges for immunoconjugates. Nat Biotechnol 2005; 23:1137 - 46; http://dx.doi.org/10.1038/nbt1141; PMID: 16151407
   PubMed Web of Science ®Google Scholar
• Yang HM, Reisfeld RA. Doxorubicin conjugated with a monoclonal antibody directed to a human melanoma-associated proteoglycan suppresses the growth of established tumor xenografts in nude mice. Proc Natl Acad Sci USA 1988; 85:1189 - 93; http://dx.doi.org/10.1073/pnas.85.4.1189; PMID: 3422487
   PubMed Web of Science ®Google Scholar
• Hinman LM, Hamann PR, Wallace R, Menendez AT, Durr FE, Upeslacis J. Preparation and characterization of monoclonal antibody conjugates of the calicheamicins: a novel and potent family of antitumor antibiotics. Cancer Res 1993; 53:3336 - 42; PMID: 8324745
   PubMed Web of Science ®Google Scholar
• Chari RV, Martell BA, Gross JL, Cook SB, Shah SA, Blättler WA, McKenzie SJ, Goldmacher VS. Immunoconjugates containing novel maytansinoids: promising anticancer drugs. Cancer Res 1992; 52:127 - 31; PMID: 1727373
   PubMed Web of Science ®Google Scholar
• Koehn FE. Natural Product Cytotoxins as Payloads for Antibody Drug Conjugates. Natural Products and Cancer Drug Discovery. 2013. 97–119.
   Google Scholar
• Anderl J, Faulstich H, Hechler T, Kulke M. Antibody-drug conjugate payloads. Methods Mol Biol 2013; 1045:51 - 70; http://dx.doi.org/10.1007/978-1-62703-541-5_4; PMID: 23913141
   PubMedGoogle Scholar
• Nolting B. Linker technologies for antibody-drug conjugates. Methods Mol Biol 2013; 1045:71 - 100; http://dx.doi.org/10.1007/978-1-62703-541-5_5; PMID: 23913142
   PubMedGoogle Scholar
• Thudium K, Bilic S, Leipold D, Mallet W, Kaur S, Meibohm B, Erickson H, Tibbitts J, Zhao H, Gupta M. American Association of Pharmaceutical Scientists National Biotechnology Conference Short Course: Translational Challenges in Developing Antibody-Drug Conjugates: May 24, 2012, San Diego, CA. MAbs 2013; 5:5 - 12; http://dx.doi.org/10.4161/mabs.22909; PMID: 23255090
   PubMed Web of Science ®Google Scholar
• Sievers EL, Senter PD. Antibody-drug conjugates in cancer therapy. Annu Rev Med 2013; 64:15 - 29; http://dx.doi.org/10.1146/annurev-med-050311-201823; PMID: 23043493
   PubMed Web of Science ®Google Scholar
• Teicher BA, Chari RV. Antibody conjugate therapeutics: challenges and potential. Clin Cancer Res 2011; 17:6389 - 97; http://dx.doi.org/10.1158/1078-0432.CCR-11-1417; PMID: 22003066
   PubMed Web of Science ®Google Scholar
• Chari RV. Targeted cancer therapy: conferring specificity to cytotoxic drugs. Acc Chem Res 2008; 41:98 - 107; http://dx.doi.org/10.1021/ar700108g; PMID: 17705444
   PubMed Web of Science ®Google Scholar
• Harper J, Mao S, Strout P, Kamal A. Selecting an optimal antibody for antibody-drug conjugate therapy: internalization and intracellular localization. Methods Mol Biol 2013; 1045:41 - 9; http://dx.doi.org/10.1007/978-1-62703-541-5_3; PMID: 23913140
   PubMedGoogle Scholar
• Bander NH. Antibody-drug conjugate target selection: critical factors. Methods Mol Biol 2013; 1045:29 - 40; http://dx.doi.org/10.1007/978-1-62703-541-5_2; PMID: 23913139
   PubMedGoogle Scholar
• Gerber H-P, Koehn FE, Abraham RT. The antibody-drug conjugate: an enabling modality for natural product-based cancer therapeutics. Nat Prod Rep 2013; 30:625 - 39; http://dx.doi.org/10.1039/c3np20113a; PMID: 23525375
   PubMed Web of Science ®Google Scholar
• Carter PJ, Senter PD. Antibody-drug conjugates for cancer therapy. Cancer J 2008; 14:154 - 69; http://dx.doi.org/10.1097/PPO.0b013e318172d704; PMID: 18536555
   PubMed Web of Science ®Google Scholar
• Ducry L, Stump B. Antibody-drug conjugates: linking cytotoxic payloads to monoclonal antibodies. Bioconjug Chem 2010; 21:5 - 13; http://dx.doi.org/10.1021/bc9002019; PMID: 19769391
   PubMed Web of Science ®Google Scholar
• Schrama D, Reisfeld RA, Becker JC. Antibody targeted drugs as cancer therapeutics. Nat Rev Drug Discov 2006; 5:147 - 59; http://dx.doi.org/10.1038/nrd1957; PMID: 16424916
   PubMed Web of Science ®Google Scholar
• Stephanopoulos N, Francis MB. Choosing an effective protein bioconjugation strategy. Nat Chem Biol 2011; 7:876 - 84; http://dx.doi.org/10.1038/nchembio.720; PMID: 22086289
   PubMed Web of Science ®Google Scholar
• Hermanson GT. Bioconjugate Techniques. Elsevier; 2008.
   Google Scholar
• Baslé E, Joubert N, Pucheault M. Protein chemical modification on endogenous amino acids. Chem Biol 2010; 17:213 - 27; http://dx.doi.org/10.1016/j.chembiol.2010.02.008; PMID: 20338513
   PubMed Web of Science ®Google Scholar
• Senter PD, Sievers EL. The discovery and development of brentuximab vedotin for use in relapsed Hodgkin lymphoma and systemic anaplastic large cell lymphoma. Nat Biotechnol 2012; 30:631 - 7; http://dx.doi.org/10.1038/nbt.2289; PMID: 22781692
   PubMed Web of Science ®Google Scholar
• van de Donk NW, Dhimolea E. Brentuximab vedotin. MAbs 2012; 4:458 - 65; http://dx.doi.org/10.4161/mabs.20230; PMID: 22684302
   PubMed Web of Science ®Google Scholar
• Dubowchik GM, Firestone RA, Padilla L, Willner D, Hofstead SJ, Mosure K, Knipe JO, Lasch SJ, Trail PA. Cathepsin B-labile dipeptide linkers for lysosomal release of doxorubicin from internalizing immunoconjugates: model studies of enzymatic drug release and antigen-specific in vitro anticancer activity. Bioconjug Chem 2002; 13:855 - 69; http://dx.doi.org/10.1021/bc025536j; PMID: 12121142
   PubMed Web of Science ®Google Scholar
• Doronina SO, Toki BE, Torgov MY, Mendelsohn BA, Cerveny CG, Chace DF, DeBlanc RL, Gearing RP, Bovee TD, Siegall CB, et al. Development of potent monoclonal antibody auristatin conjugates for cancer therapy. Nat Biotechnol 2003; 21:778 - 84; http://dx.doi.org/10.1038/nbt832; PMID: 12778055
   PubMed Web of Science ®Google Scholar
• Sun MM, Beam KS, Cerveny CG, Hamblett KJ, Blackmore RS, Torgov MY, Handley FG, Ihle NC, Senter PD, Alley SC. Reduction-alkylation strategies for the modification of specific monoclonal antibody disulfides. Bioconjug Chem 2005; 16:1282 - 90; http://dx.doi.org/10.1021/bc050201y; PMID: 16173809
   PubMed Web of Science ®Google Scholar
• Pollack VA, Alvarez E, Tse KF, Torgov MY, Xie S, Shenoy SG, MacDougall JR, Arrol S, Zhong H, Gerwien RW, et al. Treatment parameters modulating regression of human melanoma xenografts by an antibody-drug conjugate (CR011-vcMMAE) targeting GPNMB. Cancer Chemother Pharmacol 2007; 60:423 - 35; http://dx.doi.org/10.1007/s00280-007-0490-z; PMID: 17541593
   PubMed Web of Science ®Google Scholar
• Ma D, Hopf CE, Malewicz AD, Donovan GP, Senter PD, Goeckeler WF, Maddon PJ, Olson WC. Potent antitumor activity of an auristatin-conjugated, fully human monoclonal antibody to prostate-specific membrane antigen. Clin Cancer Res 2006; 12:2591 - 6; http://dx.doi.org/10.1158/1078-0432.CCR-05-2107; PMID: 16638870
   PubMed Web of Science ®Google Scholar
• Li D, Poon KA, Yu S-F, Dere R, Go M, Lau J, Zheng B, Elkins K, Danilenko D, Kozak KR, et al. DCDT2980S, an anti-CD22-monomethyl auristatin E antibody-drug conjugate, is a potential treatment for non-Hodgkin lymphoma. Mol Cancer Ther 2013; 12:1255 - 65; http://dx.doi.org/10.1158/1535-7163.MCT-12-1173; PMID: 23598530
   PubMed Web of Science ®Google Scholar
• Govindan SV, Cardillo TM, Sharkey RM, Tat F, Gold DV, Goldenberg DM. Milatuzumab-SN-38 conjugates for the treatment of CD74+ cancers. Mol Cancer Ther 2013; 12:968 - 78; http://dx.doi.org/10.1158/1535-7163.MCT-12-1170; PMID: 23427296
   PubMed Web of Science ®Google Scholar
• Lewis Phillips GD, Li G, Dugger DL, Crocker LM, Parsons KL, Mai E, Blättler WA, Lambert JM, Chari RV, Lutz RJ, et al. Targeting HER2-positive breast cancer with trastuzumab-DM1, an antibody-cytotoxic drug conjugate. Cancer Res 2008; 68:9280 - 90; http://dx.doi.org/10.1158/0008-5472.CAN-08-1776; PMID: 19010901
   PubMed Web of Science ®Google Scholar
• Wang L, Amphlett G, Blättler WA, Lambert JM, Zhang W. Structural characterization of the maytansinoid-monoclonal antibody immunoconjugate, huN901-DM1, by mass spectrometry. Protein Sci 2005; 14:2436 - 46; http://dx.doi.org/10.1110/ps.051478705; PMID: 16081651
   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; http://dx.doi.org/10.1038/nbt.1480; PMID: 18641636
   PubMed Web of Science ®Google Scholar
• Tassone P, Gozzini A, Goldmacher V, Shammas MA, Whiteman KR, Carrasco DR, Li C, Allam CK, Venuta S, Anderson KC, et al. In vitro and in vivo activity of the maytansinoid immunoconjugate huN901-N2′-deacetyl-N2′-(3-mercapto-1-oxopropyl)-maytansine against CD56+ multiple myeloma cells. Cancer Res 2004; 64:4629 - 36; http://dx.doi.org/10.1158/0008-5472.CAN-04-0142; PMID: 15231675
   PubMed Web of Science ®Google Scholar
• Ikeda H, Hideshima T, Fulciniti M, Lutz RJ, Yasui H, Okawa Y, Kiziltepe T, Vallet S, Pozzi S, Santo L, et al. The monoclonal antibody nBT062 conjugated to cytotoxic Maytansinoids has selective cytotoxicity against CD138-positive multiple myeloma cells in vitro and in vivo. Clin Cancer Res 2009; 15:4028 - 37; http://dx.doi.org/10.1158/1078-0432.CCR-08-2867; PMID: 19509164
   PubMed Web of Science ®Google Scholar
• Blanc V, Bousseau A, Caron A, Carrez C, Lutz RJ, Lambert JM. SAR3419: an anti-CD19-Maytansinoid Immunoconjugate for the treatment of B-cell malignancies. Clin Cancer Res 2011; 17:6448 - 58; http://dx.doi.org/10.1158/1078-0432.CCR-11-0485; PMID: 22003072
   PubMed Web of Science ®Google Scholar
• Hamblett KJ, Senter PD, Chace DF, Sun MMC, Lenox J, Cerveny CG, Kissler KM, Bernhardt SX, Kopcha AK, Zabinski RF, et al. Effects of drug loading on the antitumor activity of a monoclonal antibody drug conjugate. Clin Cancer Res 2004; 10:7063 - 70; http://dx.doi.org/10.1158/1078-0432.CCR-04-0789; PMID: 15501986
   PubMed Web of Science ®Google Scholar
• Alley SC, Benjamin DR, Jeffrey SC, Okeley NM, Meyer DL, Sanderson RJ, Senter PD. Contribution of linker stability to the activities of anticancer immunoconjugates. Bioconjug Chem 2008; 19:759 - 65; http://dx.doi.org/10.1021/bc7004329; PMID: 18314937
   PubMed Web of Science ®Google Scholar
• Chalker JM, Bernardes GJL, Lin YA, Davis BG. Chemical modification of proteins at cysteine: opportunities in chemistry and biology. Chem Asian J 2009; 4:630 - 40; http://dx.doi.org/10.1002/asia.200800427; PMID: 19235822
   PubMed Web of Science ®Google Scholar
• Gomez N, Vinson AR, Ouyang J, Nguyen MD, Chen X-N, Sharma VK, Yuk IH. Triple light chain antibodies: factors that influence its formation in cell culture. Biotechnol Bioeng 2010; 105:748 - 60; PMID: 19845001
   PubMed Web of Science ®Google Scholar
• Junutula JR, Flagella KM, Graham RA, Parsons KL, Ha E, Raab H, Bhakta S, Nguyen T, Dugger DL, Li G, et al. Engineered thio-trastuzumab-DM1 conjugate with an improved therapeutic index to target human epidermal growth factor receptor 2-positive breast cancer. Clin Cancer Res 2010; 16:4769 - 78; http://dx.doi.org/10.1158/1078-0432.CCR-10-0987; PMID: 20805300
   PubMed Web of Science ®Google Scholar
• Shen B-Q, Xu K, Liu L, Raab H, Bhakta S, Kenrick M, Parsons-Reponte KL, Tien J, Yu S-F, Mai E, et al. Conjugation site modulates the in vivo stability and therapeutic activity of antibody-drug conjugates. Nat Biotechnol 2012; 30:184 - 9; http://dx.doi.org/10.1038/nbt.2108; PMID: 22267010
   PubMed Web of Science ®Google Scholar
• Kung Sutherland MS, Walter RB, Jeffrey SC, Burke PJ, Yu C, Kostner H, Stone I, Ryan MC, Sussman D, Lyon RP, et al. SGN-CD33A: a novel CD33-targeting antibody-drug conjugate using a pyrrolobenzodiazepine dimer is active in models of drug-resistant AML. Blood 2013; 122:1455 - 63; http://dx.doi.org/10.1182/blood-2013-03-491506; PMID: 23770776
   PubMed Web of Science ®Google Scholar
• Strop P, Liu S-H, Dorywalska M, Delaria K, Dushin RG, Tran T-T, Ho W-H, Farias S, Casas MG, Abdiche Y, et al. Location matters: site of conjugation modulates stability and pharmacokinetics of antibody drug conjugates. Chem Biol 2013; 20:161 - 7; http://dx.doi.org/10.1016/j.chembiol.2013.01.010; PMID: 23438745
   PubMed Web of Science ®Google Scholar
• Lorand L, Graham RM. Transglutaminases: crosslinking enzymes with pleiotropic functions. Nat Rev Mol Cell Biol 2003; 4:140 - 56; http://dx.doi.org/10.1038/nrm1014; PMID: 12563291
   PubMed Web of Science ®Google Scholar
• Jeger S, Zimmermann K, Blanc A, Grünberg J, Honer M, Hunziker P, Struthers H, Schibli R. Site-specific and stoichiometric modification of antibodies by bacterial transglutaminase. Angew Chem Int Ed Engl 2010; 49:9995 - 7; http://dx.doi.org/10.1002/anie.201004243; PMID: 21110357
   PubMed Web of Science ®Google Scholar
• Ohtsuka T, Sawa A, Kawabata R, Nio N, Motoki M. Substrate specificities of microbial transglutaminase for primary amines. J Agric Food Chem 2000; 48:6230 - 3; http://dx.doi.org/10.1021/jf000302k; PMID: 11141280
   PubMed Web of Science ®Google Scholar
• Kim CH, Axup JY, Schultz PG. Protein conjugation with genetically encoded unnatural amino acids. Curr Opin Chem Biol 2013; 17:412 - 9; http://dx.doi.org/10.1016/j.cbpa.2013.04.017; PMID: 23664497
   PubMed Web of Science ®Google Scholar
• Sletten EM, Bertozzi CR. Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed Engl 2009; 48:6974 - 98; http://dx.doi.org/10.1002/anie.200900942; PMID: 19714693
   PubMed Web of Science ®Google Scholar
• Best MD. Click chemistry and bioorthogonal reactions: unprecedented selectivity in the labeling of biological molecules. Biochemistry 2009; 48:6571 - 84; http://dx.doi.org/10.1021/bi9007726; PMID: 19485420
   PubMed Web of Science ®Google Scholar
• Wang L, Brock A, Herberich B, Schultz PG. Expanding the genetic code of Escherichia coli. Science 2001; 292:498 - 500; http://dx.doi.org/10.1126/science.1060077; PMID: 11313494
   PubMed Web of Science ®Google Scholar
• Wang L, Schultz PG. Expanding the genetic code. Angew Chem Int Ed Engl 2004; 44:34 - 66; http://dx.doi.org/10.1002/anie.200460627; PMID: 15599909
   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 USA 2012; 109:16101 - 6; http://dx.doi.org/10.1073/pnas.1211023109; PMID: 22988081
   PubMed Web of Science ®Google Scholar
• Jencks WP. Mechanism and Catalysis of Simple Carbonyl Group Reactions. Prog Phys Org Chem 1964; 2:63 - 128; http://dx.doi.org/10.1002/9780470171813.ch2
   Web of Science ®Google Scholar
• Kalia J, Raines RT. Hydrolytic stability of hydrazones; oximes. Angew Chem Int Ed Engl 2008; 47:7523 - 6; http://dx.doi.org/10.1002/anie.200802651; PMID: 18712739
   PubMed Web of Science ®Google Scholar
• Doronina SO, Mendelsohn BA, Bovee TD, Cerveny CG, Alley SC, Meyer DL, Oflazoglu E, Toki BE, Sanderson RJ, Zabinski RF, et al. Enhanced activity of monomethylauristatin F through monoclonal antibody delivery: effects of linker technology on efficacy and toxicity. Bioconjug Chem 2006; 17:114 - 24; http://dx.doi.org/10.1021/bc0502917; PMID: 16417259
   PubMed Web of Science ®Google Scholar