Comparison of strain-promoted alkyne-azide cycloaddition with established methods for conjugation of biomolecules to magnetic nanoparticles

IEEE Transactions on Magnetics

Volumn 49, Issue 1, 2013, Pages 172-176

  Gruttner, Cordula ^a   Muller, Knut ^a   Teller, Joachim ^a  

^a MICROMOD PARTIKELTECHNOLOGIE GMBH   (Germany)

Author keywords

Antibody; carbodiimide; click chemistry; magnetic nanoparticle; maleimide; strain promoted alkyne azide cycloaddition (SPAAC); streptavidin

Indexed keywords

CARBODIIMIDES; CLICK CHEMISTRY; MAGNETIC NANOPARTICLES; MALEIMIDES; STRAIN-PROMOTED ALKYNE-AZIDE CYCLOADDITION (SPAAC); STREPTAVIDIN;

ACETYLENE; AMIDES; CHEMICAL BONDS; NANOMAGNETICS; NANOPARTICLES;

ANTIBODIES;

EID: 84871841996     PISSN: 00189464     EISSN: None     Source Type: Journal    
DOI: 10.1109/TMAG.2012.2218581     Document Type: Article

References (25)

1. K. Vigor, P. G. Kyrtatos, S. Minogue, K. T. Al-Jamal, H. Kogelberg, and B. Tolner et al., "Nanoparticles functionalised with recombinant single chain Fv antibody fragments (scFv) for the magnetic resonance imaging of cancer cells," Biomaterials, vol. 31, pp. 1307-1315, 2010.
2. S. J. DeNardo, G. L. DeNardo, A. Natarajan, L. A. Miers, A. R. Foreman, and C. Grüttner et al., "Thermal dosimetry predictive of efficacy of nanoparticle AMF-induced thermoablative therapy for human breast cancer in mice," J. Nucl. Med., vol. 48, pp. 437-444, 2007. (Pubitemid 47604930)
3. Q. A. Pankhurst, N. K. T. Thanh, S. K. Jones, and J. Dobson, "Progress in applications of magnetic nanoparticles in biomedicine," J. Phys. D: Appl. Phys., vol. 42, p. 224001(15pp), 2009.
4. O. Veiseh, J. W. Gunn, and M. Zhang, "Design and fabrication of magnetic nanoparticles for targeted drug delivery and imaging," Adv. Drug Delivery Rev., vol. 62, pp. 284-304, 2009.
5. J. A. Prescher and C. R. Bertozzi, "Chemistry in living systems," Nat. Chem. Biol., vol. 1, pp. 13-21, 2005.
6. P.-C. Lin, S.-H. Ueng, S.-C. Yu, M.-D. Jan, A. K. Adak, C.-C. Yu, and C.-C. Lin, "Surface modification of magnetic nanoparticle via Cu(I)-catalyzed alkyne-azide [2 3] cycloaddition," Organic Letters, vol. 9, pp. 2131-2134, 2007.
7. C. Tassa, S. Y. Shaw, and R. Weissleder, "Dextran-coated iron oxide nanoparticles: A versatile platform for targeted molecular imaging, molecular diagnostics and therapy," Acc. Chem. Res., vol. 44, pp. 842-852, 2011.
8. L. Gao, J. Zhuang, L. Nie, J. Zhang, Y. Zhang, and N. Gu et al., "Intrinsic peroxidase-like activity of ferromagnetic nanoparticles," Nature Nanotechn., vol. 2, pp. 577-583, 2007. (Pubitemid 47367542)
9. C. Grüttner, K. Müller, and J. Teller, "A rapid assay to measure the shielding of iron oxide cores by the particle shell," IEEE Trans. Magn., to be published.
10. S. T. Laughlin, J. M. Baskin, S. L. Amacher, and C. R. Bertozzi, "In vivo imaging of membrane-associated glycans in developing zebrafish," Science, vol. 320, pp. 664-667, 2008. (Pubitemid 351928348)
11. J. C. M. van Hest and F. L. van Delft, "Protein modification by strain-promoted alkyne-azide cycloaddition," ChemBioChem, vol. 12, pp. 1309-1312, 2011.
12. J. Dommerholt, S. Schmidt, R. Temming, L. J. A. Hendriks, F. P. J. T. Rutjes, and J. C. M. van Hest et al., "Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells," Angew. Chem. Int. Ed., vol. 49, pp. 9422-9425, 2010.
13. See for bicyclononyne derivatives: [Online]. Available: www. synaffix. com
14. C. L. Dennis, A. J. Jackson, J. A. Borchers, R. Ivkov, A. R. Foreman, and P. J. Hoopes et al., "The influence of magnetic and physiological behaviour on the effectiveness of iron oxide nanoparticles for hyperthermia," J. Phys. D: Appl. Phys., vol. 41, pp. 134020-134025, 2008.
15. A. J. Giustini, R. Ivkov, and P. J. Hoopes, "Magnetic nanoparticle biodistribution following intratumoral administration," Nanotechnology, vol. 22, p. 345101 (5pp), 2011.
16. J. Zhang, A. H. Dewilde, P. Chinn, A. R. Foreman, S. Barry, D. Kanne, and S. J. Braunhut, "Herceptin-directed nanoparticles activated by an alternating magnetic field selectively kill HER-2 positive human breast cancer cells in vitro via hyperthermia," Int. J. Hyperthermia, vol. 27, pp. 682-697, 2011.
17. T. Z. Gomez de la Torre, M. Strömberg, C. Russell, J. Göransson, M. Nilsson, P. Svedlindh, and M. Stromme, "Investigation of immobilization of functionalized magnetic nanobeads in rolling circle amplified DNA coils," J. Phys. Chem. B, vol. 114, pp. 3707-3713, 2010.
18. J. B. Weaver and E. Kuehlert, "Measurement of magnetic nanoparticle relaxation time," Med. Phys., vol. 39, pp. 2765-2770, 2012.
19. C. Grüttner, K. Müller, J. Teller, F. Westphal, A. R. Foreman, and R. Ivkov, "Synthesis and antibody conjugation of magnetic nanoparticles with improved specific power absorption rates for alternating magnetic field cancer therapy," J. Magn. Magn. Mater., vol. 311, pp. 181-186, 2007. (Pubitemid 46401005)
20. M. Colombo, S. Sommaruga, S. Mazzucchelli, L. Polito, P. Verderio, and P. Galeffi et al., "Site-specific conjugation of scFvs antibodies to nanoparticles by bioorthogonal strain-promoted alkyne-nitrone cycloaddition," Angew. Chem. Int. Ed., vol. 51, pp. 496-499, 2012.
21. X. Ning, R. P. Temming, J. Dommerholt, J. Guo, D. B. Ania, and M. F. Debets et al., "Protein modification by strain-promoted alkyne-nitrone cycloaddition," Angew. Chem., vol. 122, pp. 3129-3132, 2010.
22. C. S. McKay, J. A. Blake, J. Cheng, D. C. Danielson, and J. P. Pezacki, "Strain-promoted alkyne-nitrone cycloadditions for labeling human cancer cells," Chem. Commun., vol. 47, pp. 10040-10042, 2011.
23. J. M. Baskin, J. A. Prescher, D. T. Laughlin, N. J. Agard, P. V. Chang, and I. A. Miller, "Copper-free click chemistry for dynamic in vivo imaging," Proc. Natl. Acad. Sci., vol. 104, pp. 16793-16797, 2007. (Pubitemid 350210944)
24. M. F. Debets, S. S. vanBerkel, S. Schoffelen, F. P. J. T. Rutjes, J. C. M. van Hest, and F. L. van Delft, "Aza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3 2) cycloaddition," Chem. Commun., vol. 46, pp. 97-99, 2010.
25. T. Plass, S. Milles, C. Koehler, J. Szymanski, R. Mueller, and M. Wießler et al., "Amino acids for diels-alder reactions in living cells," Angew. Chem. Int. Ed., vol. 51, pp. 4166-4170, 2012.