Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 17, Pages 4652-4656Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201801113
Keywords
capping ligand; cell labeling; click chemistry; quantum dots; surface modification
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Funding
- U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences, Division of Materials Science and Engineering [DE-FG02-07ER46454]
- U.S. Army Research Office through the Institute for Soldier Nanotechnologies [W911NF-13-D-0001]
- U.S. National Science Foundation [ECCS-1449291]
- MIT Deshpande Center Innovation Grant
- Boehringer Ingelheim Fonds
- National Science Foundation [DMR-14-19807]
- Directorate For Engineering [1449291] Funding Source: National Science Foundation
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We present a novel ligand, 5-norbornene-2-nonanoic acid, which can be directly added during established quantum dot (QD) syntheses in organic solvents to generate clickable QDs at a few hundred nmol scale. This ligand has a carboxyl group at one terminus to bind to the surface of QDs and a norbornene group at the opposite end that enables straightforward phase transfer of QDs into aqueous solutions via efficient norbornene/tetrazine click chemistry. Our ligand system removes the traditional ligand-exchange step and can produce water-soluble QDs with a high quantum yield and a small hydrodynamic diameter of approximately 12 nm at an order of magnitude higher scale than previous methods. We demonstrate the effectiveness of our approach by incubating azido-functionalized CdSe/CdS QDs with 4T1 cancer cells that are metabolically labeled with a dibenzocyclooctyne-bearing unnatural sugar. The QDs exhibit high targeting efficiency and minimal nonspecific binding.
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