Development of novel quaternary ammonium linkers for antibody-drug conjugates

Molecular Cancer Therapeutics

Volumn 15, Issue 5, 2016, Pages 938-945

  Burke, Patrick J ^a   Hamilton, Joseph Z ^a   Pires, Thomas A ^a   Setter, Jocelyn R ^a   Hunter, Joshua H ^a   Cochran, Julia H ^a   Waight, Andrew B ^a   Gordon, Kristine A ^a   Toki, Brian E ^a   Emmerton, Kim K ^a   Zeng, Weiping ^a   Stone, Ivan J ^a   Senter, Peter D ^a   Lyon, Robert P ^a   Jeffrey, Scott C ^a  

^a SEATTLE GENETICS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AURISTATIN E; BETA GLUCURONIDASE; CD30 ANTIGEN; CYTOTOXIC AGENT; DESMETHYLTUBULYSIN; GLUCURONIDE; MONOCLONAL ANTIBODY; MONOMETHYLAURISTATIN E; TUBULYSIN; TUBULYSIN HYDRAZIDE; UNCLASSIFIED DRUG; AMMONIUM DERIVATIVE; ANTIBODY CONJUGATE; PROTEIN BINDING; TUBULIN;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING COMPETITION; CANCER CELL; CANCER CELL LINE; CONTROLLED STUDY; DRUG CONJUGATION; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG STABILITY; FLUORESCENCE POLARIZATION; HODGKIN DISEASE; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; KB CELL LINE; MOUSE; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REVERSED PHASE LIQUID CHROMATOGRAPHY; SIZE EXCLUSION CHROMATOGRAPHY; TUMOR ENGRAFTMENT; TUMOR REGRESSION; TUMOR VOLUME; TUMOR XENOGRAFT; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; DISEASE MODEL; DRUG SCREENING; KINETICS; RAT; TUMOR CELL LINE;

AMMONIUM COMPOUNDS; ANIMALS; ANTIBODIES, MONOCLONAL; CELL LINE, TUMOR; DISEASE MODELS, ANIMAL; DRUG LIBERATION; DRUG STABILITY; HUMANS; IMMUNOCONJUGATES; KINETICS; MICE; MOLECULAR STRUCTURE; PROTEIN BINDING; RATS; TUBULIN; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84969570456     PISSN: 15357163     EISSN: 15388514     Source Type: Journal    
DOI: 10.1158/1535-7163.MCT-16-0038     Document Type: Article

References (28)

1. Senter PD, Sievers EL. The discovery and development of brentuximab vedotin for use in relapsed Hodgkin lymphoma and systemic anaplastic large cell lymphoma. Nat Biotech 2012;30:631-7.
2. Verma S, Miles D, Gianni L, Krop IE, Welslau M, Baselga J, et al. Trastuzumab emtansine for HER2-positive advanced breast cancer. N Engl J Med 2012;367:1783-91.
3. Chari RV, Miller ML, Widdison WC. Antibody-drug conjugates: an emerging concept in cancer therapy. Angewandte Chemie 2014;53:3796-827.
4. Ducry L, Stump B. Antibody-drug conjugates: linking cytotoxic payloads to monoclonal antibodies. Bioconjugate Chem 2010;21:5-13.
5. Flygare JA, Pillow TH, Aristoff P. Antibody-drug conjugates for the treatment of cancer. Chem Biol Drug Des 2013;81:113-21.
6. Burke PJ, Senter PD, Meyer DW, Miyamoto JB, Anderson M, Toki BE, et al. Design, synthesis, and biological evaluation of antibody-drug conjugates comprised of potent camptothecin analogues. Bioconjugate Chem 2009;20:1242-50.
7. 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. Bioconjugate Chem 2002;13:855-69.
8. Doronina SO, Toki BE, Torgov MY, Mendelsohn BA, Cerveny CG, Chace DF, et al. Development of potent monoclonal antibody auristatin conjugates for cancer therapy. Nature Biotech 2003;21:778-84.
9. Dokter W, Ubink R, van der Lee M, van der Vleuten M, van Achterberg T, Jacobs D, et al. Preclinical profile of the HER2-targeting ADC SYD983/SYD985: introduction of a new duocarmycin-based linker-drug platform. Mol Cancer Ther 2014;13:2618-29.
10. Widdison WC, Wilhelm SD, Cavanagh EE, Whiteman KR, Leece BA, Kovtun Y, et al. Semisynthetic maytansine analogues for the targeted treatment of cancer. J Med Chem 2006;49:4392-408.
11. Pettit GR. The dolastatins. Fortschr Chem Org Naturst 1997;70:1-79.
12. Sasse F, Steinmetz H, Heil J, Hofle G, Reichenbach H. Tubulysins, new cytostatic peptides from myxobacteria acting on microtubuli. Production, isolation, physico-chemical and biological properties. J Antibiot 2000;53: 879-85.
13. Khalil MW, Sasse F, Lunsdorf H, Elnakady YA, Reichenbach H. Mechanism of action of tubulysin, an antimitotic peptide from myxobacteria. Chem-BioChem 2006;7:678-83.
14. Kaur G, Hollingshead M, Holbeck S, Schauer-Vukasinovic V, Camalier RF, Domling A, et al. Biological evaluation of tubulysin A: a potential anticancer and antiangiogenic natural product. Biochemical J 2006;396: 235-42.
15. Raghavan B, Balasubramanian R, Steele JC, Sackett DL, Fecik RA. Cytotoxic simplified tubulysin analogues. J Med Chem 2008;51:1530-3.
16. Leamon CP, Reddy JA, VetzelM, Dorton R,Westrick E, Parker N, et al. Folate targeting enables durable and specific antitumor responses from a therapeutically null tubulysin B analogue. Cancer Res 2008;68:9839-44.
17. Cheng H, Cong Q, Gangwar S, inventors; Antiproliferative compounds, conjugates thereof, methods therefor, and uses thereof; US patent US 8,394,922 B2. Mar 12, 2013.
18. Jeffrey SC, Andreyka JB, Bernhardt SX, Kissler KM, Kline T, Lenox JS, et al. Development and properties of beta-glucuronide linkers for monoclonal antibody-drug conjugates. Bioconjugate Chem 2006;17:831-40.
19. Lyon RP, Bovee TD, Doronina SO, Burke PJ, Hunter JH, Neff-LaFord HD, et al. Reducing hydrophobicity of homogeneous antibody-drug conjugates improves pharmacokinetics and therapeutic index. Nature Biotech 2015;33:733-5.
20. Lewis TS, Gordon KA, Li F, Weimann A, Bruders R, Miyamoto JB, et al. Characterization and circumvention of drug resistance mechanisms in SGN-35 resistant HL and ALCL clonal cell lines. [abstract]. In: Proceedings of the 105th Annual Meeting of the American Association for Cancer Research; 2014 Apr 5-9; San Diego, CA. Philadelphia (PA): AACR. Abstract nr 688.
21. Burke PJ, Toki BE, Meyer DW, Miyamoto JB, Kissler KM, Anderson M, et al. Novel immunoconjugates comprised of streptonigrin and 17-amino-geldanamycin attached via a dipeptide-p-aminobenzyl-amine linker system. Bioorg Med Chem Lett 2009;19:2650-3.
22. Jeffrey SC, Burke PJ, Lyon RP, Meyer DW, Sussman D, Anderson M, et al. A potent anti-CD70 antibody-drug conjugate combining a dimeric pyrrolobenzodiazepine drug with site-specific conjugation technology. Bioconjugate Chem 2013;24:1256-63.
23. de Graaf M, Boven E, Scheeren HW, Haisma HJ, Pinedo HM. Betaglucuronidase-mediated drug release. Curr Pharm Des 2002;8:1391-403.
24. Jeffrey SC, Nguyen MT, Moser RF, Meyer DL, Miyamoto JB, Senter PD. Minor groove binder antibody conjugates employing a water soluble betaglucuronide linker. Bioorg Med Chem Lett 2007;17:2278-80.
25. 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 Biotech 2014;32:1059-62.
26. Tercel M, Lee AE, Hogg A, Anderson RF, Lee HH, Siim BG, et al. Hypoxiaselective antitumor agents. 16 Nitroarylmethyl quaternary salts as bioreductive prodrugs of the alkylating agent mechlorethamine. J Med Chem 2001;44:3511-22.
27. Desbene S, Van HD, Michel S, Tillequin F, Koch M, Schmidt F, et al. Application of the ADEPT strategy to the MDR resistance in cancer chemotherapy. Anti-cancer Drug Des 1999;14:93-106.
28. Lehar SM, Pillow T, Xu M, Staben L, Kajihara KK, Vandlen R, et al. Novel antibody-antibiotic conjugate eliminates intracellular S. aureus. Nature 2015;527:323-8.