Template-directed covalent conjugation of DNA to native antibodies, transferrin and other metal-binding proteins

Nature Chemistry

Volumn 6, Issue 9, 2014, Pages 804-809

  Rosen, Christian B ^a,b   Kodal, Anne L B ^a,b   Nielsen, Jesper S ^a   Schaffert, David H ^a   Scavenius, Carsten ^a   Okholm, Anders H ^a   Voigt, Niels V ^a,b   Enghild, Jan J ^a   Kjems, Jørgen ^a   Tørring, Thomas ^a,b   Gothelf, Kurt V ^a,b  

^a AARHUS UNIVERSITY   (Denmark)

^b Department of Chemistry ^*  (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODY; CARRIER PROTEIN; DNA; GREEN FLUORESCENT PROTEIN; HISTIDINE; METAL; TRANSFERRIN;

AMINO ACID SEQUENCE; ANIMAL; CHEMISTRY; HUMAN; METABOLISM; MOLECULAR GENETICS;

AMINO ACID SEQUENCE; ANIMALS; ANTIBODIES; CARRIER PROTEINS; DNA; GREEN FLUORESCENT PROTEINS; HISTIDINE; HUMANS; METALS; MOLECULAR SEQUENCE DATA; TRANSFERRIN;

EID: 84906555208     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.2003     Document Type: Article

References (40)

1. Niemeyer C. M. Semisynthetic DNA-protein conjugates for biosensing and nanofabrication. Angew. Chem. Int. Ed. 49 1200-1216 (2010).
2. Stephanopoulos N. & Francis M. B. Choosing an effective protein bioconjugation strategy. Nature Chem. Biol. 7 876-884 (2011).
3. Corey D. R. & Schultz P. G. Generation of a hybrid sequence-specific singlestranded deoxyribonuclease. Science 238 1401-1403 (1987).
4. Saghatelian A. Guckian K. M. Thayer D. A. & Ghadiri M. R. DNA detection and signal amplification via an engineered allosteric enzyme. J. Am. Chem. Soc. 125 344-345 (2003).
5. Howorka S. Cheley S. & Bayley H. Sequence-specific detection of individual DNA strands using engineered nanopores. Nature Biotechnol. 19 636-639 (2001).
6. Rabuka D. Rush J. S. deHart G. W. Wu P. & Bertozzi C. R. Site-specific chemical protein conjugation using genetically encoded aldehyde tags. Nature Protoc. 7 1052-1067 (2012).
7. Kazane S. A. et al. Site-specific DNA-antibody conjugates for specific and sensitive immuno-PCR. Proc. Natl Acad. Sci. USA 109 3731-3736 (2012).
8. Kazane S. A. et al. Self-assembled antibody multimers through peptide nucleic acid conjugation. J. Am. Chem. Soc. 135 340-346 (2013).
9. Netirojjanakul C. et al. Synthetically modified Fc domains as building blocks for immunotherapy applications. Chem. Sci. 4 266-272 (2013).
10. Barbuto S. et al. Induction of innate and adaptive immunity by delivery of poly dA:dT to dendritic cells. Nature Chem. Biol. 9 250-256 (2013).
11. Keppler A. et al. A general method for the covalent labeling of fusion proteins with small molecules in vivo. Nature Biotechnol. 21 86-89 (2003).
12. Los G. V. et al. HaloTag: a novel protein labeling technology for cell imaging and protein analysis. ACS Chem. Biol. 3 373-382 (2008).
13. Gautier A. et al. An engineered protein tag for multiprotein labeling in living cells. Chem. Biol. 15 128-136 (2008).
14. Niemeyer C. M. Sano T. Smith C. L. & Cantor C. R. Oligonucleotide-directed self-assembly of proteins: semisynthetic DNA-streptavidin hybrid molecules as connectors for the generation of macroscopic arrays and the construction of supramolecular bioconjugates. Nucleic Acids Res. 22 5530-5539 (1994).
15. Tsukiji S. Miyagawa M. Takaoka Y. Tamura T. & Hamachi I. Liganddirected tosyl chemistry for protein labeling in vivo. Nature Chem. Biol. 5 341-343 (2009).
16. Hughes C. C. et al. Marinopyrrole A target elucidation by acyl dye transfer. J. Am. Chem. Soc. 131 12094-12096 (2009).
17. Uchinomiya S-H. et al. Site-specific covalent labeling of His-tag fused proteins with a reactive Ni(II)-NTA probe. Chem. Commun. 5880-5882 (2009).
18. Koshi Y. et al. Target-specific chemical acylation of lectins by ligand-tethered DMAP catalysts. J. Am. Chem. Soc. 130 245-251 (2008).
19. Meredith G. D. Wu H. Y. & Allbritton N. L. Targeted protein functionalization using His-tags. Bioconjugate Chem. 15 969-982 (2004).
20. Li G. et al. Photoaffinity labeling of small-molecule-binding proteins by DNAtemplated chemistry. Angew. Chem. Int. Ed. 52 9544-9549 (2013).
21. Vinkenborg J. L. Mayer G. & Famulok M. Aptamer-based affinity labeling of proteins. Angew. Chem. Int. Ed. 51 9176-9180 (2012).
22. Li X. & Liu D. R. DNA-templated organic synthesis: nature's strategy for controlling chemical reactivity applied to synthetic molecules. Angew. Chem. Int. Ed. 43 4848-4870 (2004).
23. Goodman R. P. et al. A facile method for reversibly linking a recombinant protein to DNA. ChemBioChem 10 1551-1557 (2009).
24. Snyder T. M. & Liu D. R. Ordered multistep synthesis in a single solution directed by DNA templates. Angew. Chem. Int. Ed. 44 7379-7382 (2005).
25. Hemdan E. S. Zhao Y. J. Sulkowski E. & Porath J. Surface topography of histidine residues: a facile probe by immobilized metal ion affinity chromatography. Proc. Natl Acad. Sci. USA 86 1811-1815 (1989).
26. Waldron K. J. Rutherford J. C. Ford D. & Robinson N. J. Metalloproteins and metal sensing. Nature 460 823-830 (2009).
27. Aisen P. & Listowsky I. Iron transport and storage proteins. Annu. Rev. Biochem. 49 357-393 (1980).
28. Douglas S. M. Bachelet I. & Church G. M. A logic-gated nanorobot for targeted transport of molecular payloads. Science 335 831-834 (2012).
29. Tran T. N. N. et al. A universal DNA-based protein detection system. J. Am. Chem. Soc. 135 14008-14011 (2013).
30. Rudchenko M. et al. Autonomous molecular cascades for evaluation of cell surfaces. Nature Nanotech. 8 580-586 (2013).
31. Jungmann R. et al. Multiplexed 3D cellular super-resolution imaging with DNA-PAINT and Exchange-PAINT. Nature Methods 11 313-318 (2014).
32. Hale J. E. & Beidler D. E. Purification of humanized murine and murine monoclonal antibodies using immobilized metal-affinity chromatography. Anal. Biochem. 222 29-33 (1994).
33. Irving H. & Williams R. J. P. The stability of transition-metal complexes. J. Chem. Soc. 3192-3210 (1953).
34. Gatter K. C. Brown G. Trowbridge I. S. Woolston R. E. & Mason D. Y. Transferrin receptors in human tissues: their distribution and possible clinical relevance. J. Clin. Pathol. 36 539-545 (1983).
35. Qian Z. M. Li H. Sun H. & Ho K. Targeted drug delivery via the transferrin receptor-mediated endocytosis pathway. Pharmacol. Rev. 54 561-587 (2002).
36. Cvetkovic A. et al. Microbial metalloproteomes are largely uncharacterized. Nature 466 779-782 (2010).
37. Sliwkowski M. X. & Mellman I. Antibody therapeutics in cancer. Science 341 1192-1198 (2013).
38. Mullard A. Maturing antibody-drug conjugate pipeline hits Nature Rev. Drug. Discov. 12 329-332 (2013).
39. Kim C. H. et al. Bispecific small molecule-antibody conjugate targeting prostate cancer. Proc. Natl Acad. Sci. USA 110 17796-17801 (2013).
40. Kularatne S. A. et al. Recruiting cytotoxic T cells to folate-receptor-positive cancer cells. Angew. Chem. Int. Ed. 52 12101-12104 (2013).