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Copper-Free Click Chemistry for Highly Luminescent Quantum Dot Conjugates: Application to in Vivo Metabolic Imaging
Abstract
Quantum dots (QD) are inorganic nanocrystals with outstanding optical properties, specially suited for biological imaging applications. Their attachment to biomolecules in mild aqueous conditions for the design of bioconjugates is therefore highly desirable. 1,3-dipolar [3 + 2] cycloaddition between azides and terminal alkynes ("click chemistry") could represent an attractive QD functionalization method. Unfortunately, the use of the popular Cu(I)-catalyzed version of this reaction is not applicable for achieving this goal, since the presence of copper dramatically alters the luminescence properties of QD dispersions. We demonstrate here that copper-free click chemistry, between strained cyclooctyne functionalized QD and azido-biomolecules, leads to highly luminescent conjugates. In addition, we show that QD-cyclooctyne can be used at previously unreported low concentration (250 nM) for imaging the incorporation of azido-modified sialic acid in cell membrane glycoproteins.
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Cited by
Quantum dots in biomedical applications
Wagner, A. M., Knipe, J. M., Orive, G., & Peppas, N. A. (2019) · Acta Biomaterialia · doi:10.1016/j.actbio.2019.05.022 · Cited by 632
Functionalization of Inorganic Nanoparticles for Bioimaging Applications
Erathodiyil, N., & Ying, J. Y. (2011) · Accounts of Chemical Research · doi:10.1021/ar2000327 · Cited by 622
Algar, W. R., Prasuhn, D. E., Stewart, M. H., Jennings, T. L., Blanco-Canosa, J. B., Dawson, P. E., & Medintz, I. L. (2011) · Bioconjugate Chemistry · doi:10.1021/bc200065z · Cited by 502
Tu, Q., Ma, C., Tian, C., Yuan, M., Han, X., Wang, D.-E., Cao, C., & Wang, J. (2016) · The Analyst · doi:10.1039/c6an00725b · Cited by 5
Metadata
- Authors
- Bernardin, A., Cazet, A., Guyon, L., Delannoy, P., Vinet, F., Bonnaffé, D., & Texier, I.
- Venue
- Bioconjugate Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-03-11
- Volume
- 21
- Issue
- 4
- Pages
- 583-588
- ISSN
- 1043-1802 (ISSN-L)
- 1520-4812
- OpenAlex
- W1987838171
- Cited by
- 165
- References
- 0
- FWCI
- 11.89
- Type
- journal article
- Language
- en
- Open access
- closed
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- Bernardin, A., Cazet, A., Guyon, L., Delannoy, P., Vinet, F., Bonnaffé, D., & Texier, I. (2010). Copper-Free Click Chemistry for Highly Luminescent Quantum Dot Conjugates: Application to in Vivo Metabolic Imaging. Bioconjugate Chemistry. https://doi.org/10.1021/bc900564w
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