Factors involved in the design of cytotoxic payloads for antibody-drug conjugates

Antibody-Drug Conjugates and Immunotoxins: From Pre-Clinical Development to Therapeutic Applications

Volumn , Issue , 2013, Pages 93-115

  Widdison, Wayne C ^a   Chari, Ravi V J ^a  

^a IMMUNOGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84939955422     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-1-4614-5456-4_6     Document Type: Chapter

References (59)

1. Zheng B, Fuji RN, Elkins K, Yu SF, Fuh FK, Chuh J et al (2009) In vivo effects of targeting CD79b with antibodies and antibody-drug conjugates. Mol Cancer Ther 8:2937-2946
2. Kraus M, Severin T, Wolf B (1994) Relevance of microenvironmental pH for self-organized tumor growth and invasion. Anticancer Res 14:1573-1583
3. Kraus M, Wolf B (1996) Implications of acidic tumor microenvironment for neoplastic growth and cancer treatment: a computer analysis. Tumour Biol 17:133-154
4. Madri JA (2003) The evolving roles of cell surface proteases in health and disease: implications for developmental, adaptive, inflammatory, and neoplastic processes. Curr Top Dev Biol 54:391-410
5. Saito G, Swanson JA, Lee KD (2003) Drug delivery strategy utilizing conjugation via reversible disulfide linkages: role and site of cellular reducing activities. Adv Drug Deliv Rev 55:199-215
6. Stephan JP, Chan P, Lee C, Nelson C, Elliott JM, Bechtel C et al (2008) Anti-CD22-MCC-DM1 and MC-MMAF conjugates: impact of assay format on pharmacokinetic parameters determination. Bioconjug Chem 19:1673-1683
7. Junutula JR, Flagella KM, Graham RA, Parsons KL, Ha E, Raab H et al (2010) Engineered thio-trastuzumab-DM1 conjugate with an improved therapeutic index to target human epidermal growth factor receptor 2-positive breast cancer. Clin Cancer Res 16:4769-4778
8. Hamblett KJ, Senter PD, Chace DF, Sun MM, Lenox J, Cerveny CG et al (2004) Effects of drug loading on the antitumor activity of a monoclonal antibody drug conjugate. Clin Cancer Res 10:7063-7070
9. Chari Ravi VJ (2008) Targeted cancer therapy: conferring specificity to cytotoxic drugs. Acc Chem Res 41:98-107
10. Le PU, Nabi IR (2003) Distinct caveolae-mediated endocytic pathways target the Golgi apparatus and the endoplasmic reticulum. J Cell Sci 116:1059-1071
11. Katz J, Janik JE, Younes A (2011) Brentuximab Vedotin (SGN-35). Clin Cancer Res 17:6428-6436
12. Sedlacek HH et al (1992) Antibodies as carriers of cytotoxicity in contributions to oncology 43, 1-145, H. Huber, W. Queisser eds, Karger, Basel
13. Uadia P, Blair AH, Ghose T (1984) Tumor and tissue distribution of a methotrexate-anti-EL4 immunoglobulin conjugate in EL4 lymphoma-bearing mice. Cancer Res 44:4263-4266
14. Tabrizi MA, Tseng CM, Roskos LK (2006) Elimination mechanisms of therapeutic monoclonal antibodies. Drug Discov Today 11:81-88
15. Shen H, Kauvar L, Tew KD (1997) Importance of glutathione and associated enzymes in drug response. Oncol Res 9:295-302
16. Ishikawa T, Kuo MT, Furuta K, Suzuki M (2000) The human multidrug resistance-associated protein (MRP) gene family: from biological function to drug molecular design. Clin Chem Lab Med 38:893-897
17. Nooter K, Stoter G (1996) Molecular mechanisms of multidrug resistance in cancer chemotherapy. Pathol Res Pract 192:768-780
18. Kovtun YV, Audette CA, Mayo MF, Jones GE, Doherty H, Maloney EK et al (2010) Antibody- maytansinoid conjugates designed to bypass multidrug resistance. Cancer Res 70:2528-2537
19. Vaupel P, Mayer A (2007) Hypoxia in cancer: significance and impact on clinical outcome. Cancer Metastasis Rev 26:225-239
20. Sullivan R, Paré GC, Frederiksen LJ, Semenza GL, Graham CH (2008) Hypoxia-induced resistance to anticancer drugs is associated with decreased senescence and requires hypoxia- inducible factor-1 activity. Mol Cancer Ther 7:1961-1973
21. Teicher BA (1994) Hypoxia and drug resistance. Cancer Metastasis Rev 13:139-168
22. Caglic D, Kosec G, Bojic L, Reinheckel T, Turk V, Turk B (2009) Murine and human cathepsin B exhibit similar properties: possible implications for drug discovery. Biol Chem 390:175-179
23. Puente XS, Sanchez LM, Overall CM, Lopez-Otin C (2003) Human and mouse proteases: a comparative genomic approach. Nat Rev Genet 4:544-558
24. Bai R, Edler MC, Bonate PL, Copeland TD, Pettit GR, Luduena RF et al (2009) Intracellular activation and deactivation of tasidotin, an analog of dolastatin 15: correlation with cytotoxicity. Mol Pharmacol 75:218-226
25. Erickson HK, Park PU, Widdison WC, Kovtun YV, Garrett LM, Hoffman K et al (2006) Antibody-maytansinoid conjugates are activated in targeted cancer cells by lysosomal degradation and linker-dependent intracellular processing. Cancer Res 66:4426-4433
26. Doronina SO, Mendelsohn BA, Bovee TD, Cerveny CG, Alley SC, Meyer DL et al (2006) Enhanced activity of monomethylauristatin F through monoclonal antibody delivery: effects of linker technology on efficacy and toxicity. Bioconjug Chem 17:114-124
27. Dubowchik GM, Firestone RA, Padilla L, Willner D, Hofstead SJ, Mosure K et al (2002) 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 13:855-869
28. Zhao RY, Wilhelm SD, Audette C, Jones G, Leece BA, Lazar AC et al (2011) Synthesis and evaluation of hydrophilic linkers for antibody-maytansinoid conjugates. J Med Chem 54:3606-3623
29. Wu G, Fang YZ, Yang S, Lupton JR, Turner ND (2004) Glutathione metabolism and its implications for health. J Nutr 134:489-492
30. Mills BJ, Lang CA (1996) Differential distribution of free and bound glutathione and cyst(e) ine in human blood. Biochem Pharmacol 52:401-406
31. Kupchan SM, Komoda Y, Court WA, Thomas GJ, Smith RM, Karim A et al (1972) Maytansine, a novel antileukemic ansa macrolide from Maytenus ovatus. J Am Chem Soc 94:1354-1356
32. Remillard S, Rebhun LI, Howie GA, Kupchan SM (1975) Antimitotic activity of the potent tumor inhibitor maytansine. Science 189:1002-1005
33. Gerber HP, Kung-Sutherland M, Stone I, Morris-Tilden C, Miyamoto J, McCormick R et al (2009) Potent antitumor activity of the anti-CD19 auristatin antibody drug conjugate hBU12- vcMMAE against rituximab-sensitive and -resistant lymphomas. Blood 113:4352-4361
34. Thorson JS, Sievers EL, Ahlert J, Shepard E, Whitwam RE, Onwueme KC et al (2000) Understanding and exploiting nature's chemical arsenal: the past, present and future of cali- cheamicin research. Curr Pharm Des 6:1841-1879
35. Boger D (1994) Design, synthesis, and evaluation of DNA minor groove binding agents: the duocarmycins. Pure Appl Chem 66:837-844
36. Gascoigne KE, Taylor SS (2009) How do anti-mitotic drugs kill cancer cells? J Cell Sci 122:2579-2585
37. Jordan MA, Himes RH, Wilson L (1985) Comparison of the effects of vinblastine, vincristine, vindesine, and vinepidine on microtubule dynamics and cell proliferation in vitro. Cancer Res 45:2741-2747
38. Hadfield JA, Ducki S, Hirst N, McGown AT (2003) Tubulin and microtubules as targets for anticancer drugs. Prog Cell Cycle Res 5:309-325
39. Lopus M, Oroudjev E, Wilson L, Wilhelm S, Widdison W, Chari R et al (2010) Maytansine and cellular metabolites of antibody-maytansinoid conjugates strongly suppress microtubule dynamics by binding to microtubules. Mol Cancer Ther 9:2689-2699
40. Cassady JM, Chan KK, Floss HG, Leistner E (2004) Recent developments in the maytansinoid antitumor agents. Chem Pharm Bull (Tokyo) 52:1-26
41. Widdison WC, Wilhelm SD, Cavanagh EE, Whiteman KR, Leece BA, Kovtun Y et al (2006) Semisynthetic maytansine analogues for the targeted treatment of cancer. J Med Chem 49:4392-4408
42. Kellogg BA, Garrett L, Kovtun Y, Lai KC, Leece B, Miller M et al (2011) Disulfide-linked antibody-maytansinoid conjugates: optimization of in vivo activity by varying the steric hindrance at carbon atoms adjacent to the disulfide linkage. Bioconjug Chem 22:717-727
43. Kovtun YV, Audette CA, Ye Y, Xie H, Ruberti MF, Phinney SJ et al (2006) Antibody-drug conjugates designed to eradicate tumors with homogeneous and heterogeneous expression of the target antigen. Cancer Res 66:3214-3221
44. Oroudjev E, Lopus M, Wilson L, Audette C, Provenzano C, Erickson H et al (2010) Maytansinoid-antibody conjugates induce mitotic arrest by suppressing microtubule dynamic instability. Mol Cancer Ther 9:2700-2713
45. Pettit RK, Pettit GR, Hazen KC (1998) Specific activities of dolastatin 10 and peptide derivatives against Cryptococcus neoformans. Antimicrob Agents Chemother 42:2961-2965
46. Pettit GR, Srirangam JK, Barkoczy J, Williams MD, Boyd MR, Hamel E et al (1998) Antineoplastic agents 365. Dolastatin 10 SAR probes. Anticancer Drug Des 13:243-277
47. Okeley NM, Miyamoto JB, Zhang X, Sanderson RJ, Benjamin DR, Sievers EL et al (2010) Intracellular activation of SGN-35, a potent anti-CD30 antibody-drug conjugate. Clin Cancer Res 16:888-897
48. Silverman RB (2004) The organic chemistry of drug design and drug action, 2nd edn. Elsevier Academic Press, Amsterdam/Boston
49. Reich Z, Ghirlando R, Arad T, Weinberger S, Minsky A (1990) Extensive interference of DNA packaging processes affected by chemotherapeutic drugs. J Biol Chem 265:16004-16006
50. Leijen S, Beijnen JH, Schellens JH (2010) Abrogation of the G2 checkpoint by inhibition of Wee-1 kinase results in sensitization of p53-deficient tumor cells to DNA-damaging agents. Curr Clin Pharmacol 5:186-191
51. Burden DA, Osheroff N (1998) Mechanism of action of eukaryotic topoisomerase II and drugs targeted to the enzyme. Biochim Biophys Acta 1400:139-154
52. Sapra P, Stein R, Pickett J, Qu Z, Govindan SV, Cardillo TM et al (2005) Anti-CD74 antibody- doxorubicin conjugate, IMMU-110, in a human multiple myeloma xenograft and in monkeys. Clin Cancer Res 11:5257-5264
53. Mitsiades CS, Mitsiades NS, Munshi NC, Richardson PG, Anderson KC (2006) The role of the bone microenvironment in the pathophysiology and therapeutic management of multiple myeloma: interplay of growth factors, their receptors and stromal interactions. Eur J Cancer 42:1564-1573
54. Lee MD, Dunne TS, Chang CC, Ellestad GA, Siegel MM, Morton GO, McGahren WJ, Borders DB (1987) Calichemicins, a novel family of antitumor antibiotics. 2. Chemistry and structure of calichemicin gamma 1. J Am Chem Soc 109:3466-3468
55. Hamann PR, Hinman LM, Beyer CF, Greenberger LM, Lin C, Lindh D et al (2005) An anti- MUC1 antibody-calicheamicin conjugate for treatment of solid tumors. Choice of linker and overcoming drug resistance. Bioconjug Chem 16:346-353
56. Rajvanshi P, Shulman HM, Sievers EL, McDonald GB (2002) Hepatic sinusoidal obstruction after gemtuzumab ozogamicin (Mylotarg) therapy. Blood 99:2310-2314
57. Advani A, Coiffier B, Czuczman MS, Dreyling M, Foran J, Gine E et al (2010) Safety, pharmacokinetics, and preliminary clinical activity of inotuzumab ozogamicin, a novel immuno- conjugate for the treatment of B-cell non-Hodgkin's lymphoma: results of a phase I study. J Clin Oncol 28:2085-2093
58. Fuerst M (2011) NHL: Inotuzumab ozogamicin shows activity both alone & combined with rituximab. Oncol Times 33:52-53
59. Ichimura M, Ogawa T, Katsumata S, Takahashi K, Takahashi I, Nakano H (1991) Duocarmycins, new antitumor antibiotics produced by Streptomyces; producing organisms and improved production. J Antibiot (Tokyo) 44:1045-1053