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Versatile naphthalimide tetrazines for fluorogenic bioorthogonal labelling
- Source :
- RSC Chemical Biology
- Publication Year :
- 2021
- Publisher :
- Royal Society of Chemistry (RSC), 2021.
-
Abstract
- Fluorescent probes for biological imaging have revealed much about the functions of biomolecules in health and disease. Fluorogenic probes, which are fluorescent only upon a bioorthogonal reaction with a specific partner, are particularly advantageous as they ensure that fluorescent signals observed in biological imaging arise solely from the intended target. In this work, we report the first series of naphthalimide tetrazines for bioorthogonal fluorogenic labelling. We establish that all of these compounds can be used for imaging through photophysical, analytical and biological studies. The best candidate was Np6mTz, where the tetrazine ring is appended to the naphthalimide at its 6-position via a phenyl linker in a meta configuration. Taking our synthetic scaffold, we generated two targeted variants, LysoNpTz and MitoNpTz, which successfully localized within the lysosomes and mitochondria respectively, without the requirement of genetic modification. In addition, the naphthalimide tetrazine system was used for the no-wash imaging of insulin amyloid fibrils in vitro, providing a new method that can monitor their growth kinetics and morphology. Since our synthetic approach is simple and modular, these new naphthalimide tetrazines provide a novel scaffold for a range of bioorthogonal tetrazine-based imaging agents for selective staining and sensing of biomolecules.<br />New naphthalimide tetrazine probes permit fluorescent imaging of biomolecules in vitro and in living cells. They can be modified to provide previously unknown information about health and disease in biological systems.
- Subjects :
- chemistry.chemical_classification
Biological studies
010405 organic chemistry
Biomolecule
010402 general chemistry
01 natural sciences
Biochemistry, Genetics and Molecular Biology (miscellaneous)
Biochemistry
Combinatorial chemistry
Fluorescence
0104 chemical sciences
3. Good health
Chemistry
Tetrazine
chemistry.chemical_compound
chemistry
Chemistry (miscellaneous)
Labelling
Bioorthogonal chemistry
Biological imaging
Molecular Biology
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Subjects
Details
- ISSN :
- 26330679
- Volume :
- 2
- Database :
- OpenAIRE
- Journal :
- RSC Chemical Biology
- Accession number :
- edsair.doi.dedup.....f3af9727305e6c70e634bff25d345f80