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Modulation of Mitochondriotropic Properties of Cyanine Dyes by in Organello Copper‐Free Click Reaction
Authors:Inka Negwer  Dr. Markus Hirsch  Dr. Stefka Kaloyanova  Prof. Dr. Tom Brown  Prof. Dr. Kalina Peneva  Prof. Dr. Hans‐Jürgen Butt  Dr. Kaloian Koynov  Prof. Dr. Mark Helm
Affiliation:1. Pharmaceutical Chemistry, Institute of Pharmacy and Biochemistry, Johannes Gutenberg University, Mainz, Germany;2. Max Planck Institute for Polymer Research, Mainz, Germany;3. University of Oxford, Department of Chemistry, Chemistry Research Laboratory, Oxford, UK;4. Laboratory of Organic and Macromolecular Chemistry, Jena Center of Soft Matter, Friedrich-Schiller-University Jena, Jena, Germany
Abstract:Cyanine (Cy) dyes show a general propensity to localize in polarized mitochondria. This mitochondriotropism was used to perform a copper‐free click reaction in the mitochondria of living cells. The in organello reaction of dyes Cy3 and Cy5 led to a product that was easily traceable by Förster resonance energy transfer (FRET). As determined by confocal laser scanning microscopy, the Cy3–Cy5 conjugate showed enhanced retention in mitochondria, relative to that of the starting compounds. This enhancement of a favorable property can be achieved by synthesis in organello, but not outside mitochondria.
Keywords:click chemistry  fluorescent probes  FRET  in organello synthesis  mitochondrial targeting
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