Current ADC Linker Chemistry

Pharmaceutical Research

Volumn 32, Issue 11, 2015, Pages 3526-3540

  Jain, Nareshkumar ^a   Smith, Sean W ^a   Ghone, Sanjeevani ^a   Tomczuk, Bruce ^a  

^a Chemistry Research Solution LLC   (United States)

Author keywords

ADC; ADC clinical candidates; antibody drug conjugates; bioconjugates; linker chemistry

Indexed keywords

ANTIBODY CONJUGATE; BRENTUXIMAB VEDOTIN; CALICHEAMICIN; CYSTEINE; CYTOTOXIN; DRUG ANTIBODY; FIRTECAN; LYSINE; TRASTUZUMAB EMTANSINE; DRUG; MONOCLONAL ANTIBODY;

ANTIBODY SPECIFICITY; CHEMISTRY; CROSS LINKING; DRUG CONJUGATION; DRUG RESEARCH; GENETIC ENGINEERING; PRIORITY JOURNAL; REVIEW; PROCEDURES; PROTEIN ENGINEERING;

ANTIBODIES, MONOCLONAL; CYSTEINE; IMMUNOCONJUGATES; LYSINE; PHARMACEUTICAL PREPARATIONS; PROTEIN ENGINEERING;

EID: 84943585919     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-015-1657-7     Document Type: Review

References (41)

1. Schwartz RS. Paul Ehrlich's magic bullets. N Engl J Med. 2004;350:1079-80.
2. Lapusan S, Vidriales MB, Thomas X, de Botton S, Vekhoff A, Tang R, et al. Phase I studies of AVE9633, an anti-CD33 antibody-maytansinoid conjugate, in adult patients with relapsed/refractory acute myeloid leukemia. Investig New Drugs. 2012;30:1121-31.
3. Lonberg N. Human antibodies from transgenic animals. Nat Biotechnol. 2005;23:1117-25.
4. Teicher BA, Chari RVJ. Antibody conjugate therapeutics: challenges and potential. Clin Cancer Res. 2011;17:6389-97.
5. Trail PA. Antibody drug conjugates as cancer therapeutics. Antibodies. 2013;2:113-29.
6. Lambert JM. Drug-conjugated antibodies for the treatment of cancer. Br J Clin Pharmacol. 2012;76:248-62.
7. Perez HL, Cardarelli PM, Deshpande S, Gangwar S, Schroeder GM, Vite GD, et al. Drug Discov Today. 2014;19:869-81.
8. Jarvis LM. Rethinking antibody-drug conjugates. Chem Eng News. 2012;90:12-8.
9. Joubert MK, Hokom M, Eakin C, Zhou L, Despande M, Baker MP, et al. Highly aggregated antibody therapeutics can enhance the in vitro innate and late-stage T-cell immune responses. J Biol Chem. 2012;287:25266-79.
10. Kovtun YV, Audette CA, Mayo MF, Jones GE, Doherty H, Maloney EK, et al. Antibody-maytansinoid conjugates designed to bypass multidrug resistance. Cancer Res. 2010;70:2528-37.
11. Panowski S, Bhakta S, Raab H, Polakis P, Junutula JR. Site-specific antibody drug conjugates for cancer therapy. mAbs. 2014;6:1-12.
12. Junutula JR, Raab H, Clark S, Bhakta S, Leipold DD, Weir S, et al. Site-specific conjugation of a cytotoxic drug to an antibody improves the therapeutic index. Nat Biotechnol. 2008;26:925-32.
13. Dubowchik GM, Firestone RA, Padilla L, Willner D, Hofstead SJ, Mosure K, et al. 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.
14. Ritchie M, Tchistiakova L, Scott N. Implications of receptor-mediated endocytosis and intracellular trafficking dynamics in the development of antibody drug conjugates. mAbs. 2013;5:13-21.
15. Lyon RP, Setter JR, Bovee TD, Doronina SO, Hunter JH, Anderson ME, et al. Self-hydrolyzing maleimides improve the stability and pharmacological properties of antibody-drug conjugates. Nat Biotechnol. 2014;32:1059-62.
16. 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.
17. Dorinina SO, Mendelsohn BA, Bovee TD, Cerveny CG, Alley SC, Meyer DL, 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.
18. Antonow D, Thurston DE. Synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines (PBDs). Chem Rev. 2011;111:2815-64.
19. Hartley JA, Hamaguchi A, Suggitt M, Gregson SJ, Thurston DE, Howard PW. DNA interstrand cross-linking and in vivo antitumor activity of the extended pyrrolo[2,1-c][1,4]benzodiazepine dimer SG2057. Investig New Drugs. 2012;30:950-8.
20. Dokter W, Ubink R, van der Lee M, van der Vleuten M, van Acgterberg T, Jacobs D, et al. Impressive efficacy and safety profile of a novel generation duocarmycin-based HER2-targeting ADC. Am Assoc Cancer Res. 2014; Poster #2651, San Diego, CA.
21. Dotan E, Berlin JD, Starodub AN, Guarino MJ, Cohen SJ, Maliakal PP, et al. Activity of IMMU-130 anti-CEACAM5-SN-38 antibody-drug conjugate (ADC) on metastatic colorectal cancer (mCRC) having relapsed after CPT-11: Phase I study. J Clin Oncol. 2014; 32(5s):abst 3106.
22. Cardillo TM, Govindan SV, Sharkey RM, Trisal P, Goldenberg DM. Humanized Anti-TROP-2 IgG-SN-38 conjugate for effective treatment of diverse epithelial cancers: preclinical studies in human cancer xenograft models and monkeys. Clin Cancer Res. 2011;17:3157-69.
23. 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.
24. Guo J, Kumar S, Prashad A, Starkey J, Singh SK. Assessment of physical stability of an antibody drug conjugate by higher order structure analysis: impact of thiol-maleimide chemistry. Pharm Res. 2014;31:1710-23.
25. Badescu G, Bryant P, Bird M, Henseleit K, Swierkosz J, Parekh V, et al. Bridging disulfides for stable and defined antibody drug conjugates. Bioconjug Chem. 2014;25:1124-36.
26. Kim MT, Chen Y, Marhoul J, Jacobson F. Statistical modeling of the drug load distribution on trastuzumab emtansine (Kadcyla), a lysine-linked antibody drug conjugate. Bioconjug Chem. 2014;25:1223-32.
27. Phillips GDL, Li G, Dugger DL, Crocker LM, Parsons KL, Mai E, et al. Targeting HER2-positive breast cancer with trastuzumab-DM1, an antibody-drug conjugate. Cancer Res. 2008;68:9280-90.
28. Zhao RY, Wilheim SD, Audette C, Jones G, Leece BA, Lazar AC, et al. Synthesis and evaluation of hydrophilic linkers for antibody-maytansinoid conjugates. J Med Chem. 2011;54:3603-23.
29. DiJoseph JF, Khandke K, Dougher MM, Evans DY, Armellino DC, Hamann PR, et al. CMC-544 (inotuzumab ozogamicin): a CD22-targeted immunoconjugate of calicheamicin. Hematol Meet Rep. 2008;2:74-7.
30. Walker S, Landovitz R, Ding WD, Ellestad GA, Kahne D. Cleavage behavior of calicheamicin gamma 1 and calicheamicin T. Proc Natl Acad Sci U S A. 1992;89:4608-12.
31. Prokop A, Wrasidlo W, Lode H, Herold R, Lang F, Henze G, et al. Induction of apoptosis by enediyne antibiotic calicheamicin II proceeds through a caspase-mediated mitochondrial amplication loop in an entirely Bax-dependent manner. Oncogene. 2003;22:9107-20.
32. Junutula JR, Flagella KM, Graham RA, Parsons KL, Ha E, Raab H, 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.
33. Hofer T, Skeffington LR, Chapman CM, Rader C. Molecularly defined antibody conjugation through a selenocysteine interface. Biochemistry. 2009;48:12047-57.
34. Axup JY, Bajjuri KM, Ritland M, Hutchins BM, Kim CH, Kazane SA, et al. Synthesis of site-specific antibody-drug conjugates using unnatural amino acids. Proc Natl Acad Sci U S A. 2012;109:16101-6.
35. Agarwal P, van der Weijden J, Sletten EM, Rabuka D, Bertozzi CR. A Pictet-Spengler ligation for protein chemical modification. Proc Natl Acad Sci U S A. 2013;110:46-51.
36. Agarwal P, Kudirka R, Albers AE, Barfield RM, de Hart GW, Drake PM, et al. Hydrazino-Pictet-Spengler ligation as a biocompatible method for the generation of stable protein conjugates. Bioconjug Chem. 2013;24:846-51.
37. Zimmerman ES, Heibeck TH, Gill A, Li X, Murray CJ, Madlansacay MR, 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.
38. Boeggeman E, Ramakrishnan B, Pasek M, Manzoni M, Puri A, Loomis KH, et al. Site specific conjugation of fluoroprobes to the remodeled Fc N-glycans of monoclonal antibodies using mutant glycosyltransferases: application for cell-surface antigen detection. Bioconjug Chem. 2009;20:1228-36.
39. Farias SE, Strop P, Delaria K, Casas MG, Dorywalska M, Shelton DL, et al. Mass spectrometric characterization of transglutaminase based site-specific antibody-drug conjugate. Bioconjug Chem. 2014;25:240-50.
40. Strop P. Versatility of microbial transglutaminase. Bioconjug Chem. 2014;25:855-62.
41. Tian F, Lu Y, Manibusan A, Sellers A, Tran H, Sun Y, et al. A general approach to site-specific antibody drug conjugates. Proc Natl Acad Sci U S A. 2014;111:1766-71.