A plug-and-play approach to antibody-based therapeutics via a chemoselective dual click strategy

Nature Communications

Volumn 6, Issue , 2015, Pages

  Maruani, Antoine ^a   Smith, Mark E B ^a   Miranda, Enrique ^b   Chester, Kerry A ^b   Chudasama, Vijay ^a   Caddick, Stephen ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODY; DRUG ANTIBODY; EPIDERMAL GROWTH FACTOR RECEPTOR 2; ANTIBODY CONJUGATE; ANTINEOPLASTIC AGENT; ERBB2 PROTEIN, HUMAN; TRASTUZUMAB;

ANTIBODY; CANCER; CHEMICAL BINDING; CYTOLOGY;

ANTIBODY STRUCTURE; ANTIGEN BINDING; ARTICLE; BREAST CANCER CELL LINE; CHEMOSELECTIVE DUAL CLICK STRATEGY; CONJUGATE; CONTROLLED STUDY; CYTOTOXICITY ASSAY; INTERNALIZATION; THERAPY; BREAST NEOPLASMS; CHEMISTRY; CLICK CHEMISTRY; CONFOCAL MICROSCOPY; DRUG DELIVERY SYSTEM; HUMAN; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; POLYACRYLAMIDE GEL ELECTROPHORESIS; PROCEDURES; TUMOR CELL LINE; X RAY PHOTOELECTRON SPECTROSCOPY;

ANTIBODIES; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE, TUMOR; CHROMATOGRAPHY, LIQUID; CLICK CHEMISTRY; DRUG DELIVERY SYSTEMS; ELECTROPHORESIS, POLYACRYLAMIDE GEL; HUMANS; IMMUNOCONJUGATES; MASS SPECTROMETRY; MICROSCOPY, CONFOCAL; PHOTOELECTRON SPECTROSCOPY; RECEPTOR, ERBB-2; TRASTUZUMAB;

EID: 84926284885     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms7645     Document Type: Article

References (41)

1. Sapra, P., Hooper, A. T., O'Donnell, C. J., amp; Gerber, H.-P. Investigational antibody drug conjugates for solid tumors. Expert Opin. Investig. Drugs 20, 1131-1149 (2011).
2. Alley, S. C., Okeley, N. M., amp; Senter, P. D. Antibody-drug conjugates: targeted drug delivery for cancer. Curr. Opin. Chem. Biol. 14, 529-537 (2010).
3. Hess, C., Venetz, D., amp; Neri, D. Emerging classes of armed antibody therapeutics against cancer. Med. Chem. Comm. 5, 408-431 (2014).
4. Adair, J. R., Howard, P. W., Hartley, J. A., Williams, D. G., amp; Chester, K. A. Antibody-drug conjugates-a perfect synergy. Expert Opin. Biol. Ther. 12, 1191-1206 (2012).
5. Mullard, A. Maturing antibody-drug conjugate pipeline hits 30. Nat. Rev. Drug Discov. 12, 329-332 (2013).
6. Sassoon, I., amp; Blanc, V. Antibody-drug conjugate (ADC) clinical pipeline: a review. Methods Mol. Biol. 1045, 1-27 (2013).
7. Flygare, J. A., Pillow, T. H., amp; Aristoff, P. Antibody-drug conjugates for the treatment of cancer. Chem. Biol. Drug Des. 81, 113-121 (2013).
8. Ducry, L., amp; Stump, B. Antibody-drug conjugates: linking cytotoxic payloads to monoclonal antibodies. Bioconjug. Chem. 21, 5-13 (2010).
9. Junutula, J. R. 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. 16, 4769-4778 (2010).
10. Junutula, J. R. et al. Site-specific conjugation of a cytotoxic drug to an antibody improves the therapeutic index. Nat. Biotechnol. 26, 925-932 (2008).
11. Zimmerman, E. S. et al. Production of site-specific antibody-drug conjugates using optimized non-natural amino acids in a cell-free expression system. Bioconjug. Chem. 25, 351-361 (2014).
12. Castañeda, L. et al. Acid-cleavable thiomaleamic acid linker for homogeneous antibody-drug conjugation. Chem. Commun. 49, 8187-8189 (2013).
13. Schumacher, F. F. et al. Homogeneous antibody fragment conjugation by disulfide bridging introduces 'spinostics'. Sci. Rep. 3, 1525 (2013).
14. Ryan, C. P. et al. Tunable reagents for multi-functional bioconjugation: reversible or permanent chemical modification of proteins and peptides by control of maleimide hydrolysis. Chem. Commun. 47, 5452-5454 (2011).
15. Schumacher, F. F. et al. Next generation maleimides enable the controlled assembly of antibody-drug conjugates via native disulfide bond bridging. Org. Biomol. Chem. 12, 7261-7269 (2014).
16. Schumacher, F. F. et al. In situ maleimide bridging of disulfides and a new approach to protein PEGylation. Bioconjug. Chem. 22, 132-136 (2011).
17. Smith, M. E. B. et al. Protein modification, bioconjugation, and disulfide bridging using bromomaleimides. J. Am. Chem. Soc. 132, 1960-1965 (2010).
18. Chudasama, V. et al. Bromopyridazinedione-mediated protein and peptide bioconjugation. Chem. Commun. 47, 8781-8783 (2011).
19. Maruani, A. et al. A mild TCEP-based para-azidobenzyl cleavage strategy to transform reversible cysteine thiol labelling reagents into irreversible conjugates. Chem. Commun. 51, 5279-5282 (2015).
20. Badescu, G. et al. Bridging disulfides for stable and defined antibody drug conjugates. Bioconjug. Chem. 25, 1124-1136 (2014).
21. Hudis, C. A. Trastuzumab-mechanism of action and use in clinical practice. N. Engl. J. Med. 357, 39-51 (2007).
22. Verma, S. et al. Trastuzumab emtansine for HER2-positive advanced breast cancer. N. Engl. J. Med. 367, 1783-1791 (2012).
23. Jalota, S., Bhaduri, S. B., amp; Tas, A. C. Using a synthetic body fluid (SBF) solution of 27 mM HCO3-to make bone substitutes more osteointegrative. Mater. Sci. Eng. C 28, 129-140 (2008).
24. Thorp-Greenwood, F. L., amp; Coogan, M. P. Multimodal radio-(PET/SPECT) and fluorescence imaging agents based on metallo-radioisotopes: current applications and prospects for development of new agents. Dalton Trans. 40, 6129-6143 (2011).
25. Crawley, N., Thompson, M., amp; Romaschin, A. Theranostics in the growing field of personalized medicine: an analytical chemistry perspective. Anal. Chem. 86, 130-160 (2014).
26. Schmidt, M. M., amp; Wittrup, K. D. A modeling analysis of the effects of molecular size and binding affinity on tumor targeting. Mol. Cancer Ther. 8, 2861-2871 (2009).
27. Yokota, T., Milenic, D. E., Whitlow, M., amp; Schlom, J. Rapid tumor penetration of a single-chain Fv and comparison with other immunoglobulin forms. Cancer Res. 52, 3402-3408 (1992).
28. Thurber, G. M., Schmidt, M. M., amp; Wittrup, K. D. Antibody tumor penetration: transport opposed by systemic and antigen-mediated clearance. Adv. Drug Deliv. Rev. 60, 1421-1434 (2008).
29. Holliger, P., amp; Hudson, P. J. Engineered antibody fragments and the rise of single domains. Nat. Biotechnol. 23, 1126-1136 (2005).
30. Milenic, D. E. et al. Construction, binding properties, metabolism, and tumor targeting of a single-chain Fv derived from the pancarcinoma monoclonal antibody CC49. Cancer Res. 51, 6363-6371 (1991).
31. Williams, L. E. et al. Numerical selection of optimal tumor imaging agents with application to engineered antibodies. Cancer Biother. Radiopharm. 16, 25-35 (2001).
32. Holt, L. J., Herring, C., Jespers, L. S., Woolven, B. P., amp; Tomlinson, I. M. Domain antibodies: proteins for therapy. Trends Biotechnol. 21, 484-490 (2003).
33. Deen, W. M., Lazzara, M. J., amp; Myers, B. D. Structural determinants of glomerular permeability. Am. J. Physiol. Renal Physiol. 281, 579-596 (2001).
34. Chapman, A. P. et al. Therapeutic antibody fragments with prolonged in vivo half-lives. Nat. Biotechnol. 17, 780-783 (1999).
35. Yang, K. et al. Tailoring structure-function and pharmacokinetic properties of single-chain Fv proteins by site-specific PEGylation. Protein Eng. 16, 761-770 (2003).
36. Fishburn, C. S. The pharmacology of PEGylation: balancing PD with PK to generate novel therapeutics. J. Pharm. Sci. 97, 4167-4183 (2008).
37. Brocchini, S. et al. Disulfide bridge based PEGylation of proteins. Adv. Drug Deliv. Rev. 60, 3-12 (2008).
38. Das, M., Jain, R., Agrawal, A. K., Thanki, K., amp; Jain, S. Macromolecular bipill of gemcitabine and methotrexate facilitates tumor-specific dual drug therapy with higher benefit-to-risk ratio. Bioconjug. Chem. 25, 501-509 (2014).
39. Thiyagarajan, D., Goswami, S., Kar, C., Das, G., amp; Ramesh, A. A prospective antibacterial for drug-resistant pathogens: a dual warhead amphiphile designed to track interactions and kill pathogenic bacteria by membrane damage and cellular DNA cleavage. Chem. Commun. 50, 7434-7436 (2014).
40. Silver, L. L. Challenges of antibacterial discovery. Clin. Microbiol. Rev. 24, 71-109 (2011).
41. O'Connell, K. M. G. et al. Combating multidrug-resistant bacteria: current strategies for the discovery of novel antibacterials. Angew. Chem. Int. Ed. 52, 10706-10733 (2013).