Design and Synthesis of Near-Infrared Mechanically Interlocked Molecules for Specific Targeting of Mitochondria
Rabi Sankar Das, Pranab Chandra Saha, Nayim Sepay, Ayan Mukherjee, Sudipta Chatterjee, Samit Guha
Abstract
The entrapment of squaraine (SQ) within a molecular container to form rotaxane has been shown to improve the dye stability and the fluorescence proficiency inside the mitochondria. The macrocycle provides shelter and protects the near-infrared (NIR) SQ chromophore from nucleophilic attacks made by the exposed thiol of Cys-containing mitochondrial proteins and mitochondrial glutathione. Herein a microwave-assisted template-directed clipping reaction on low-loading 2-chlorotrityl chloride resin is used to develop an NIR unsymmetrical squaraine rotaxane in high quantum yield.
Topics & Concepts
ChemistryChromophoreRotaxaneMoleculeInfraredPhotochemistryQuantum yieldFluorescenceMitochondrionYield (engineering)NucleophileNucleophilic additionCombinatorial chemistryOrganic chemistryBiochemistryMaterials scienceMetallurgyQuantum mechanicsOpticsPhysicsSupramolecular chemistryCatalysisSupramolecular Chemistry and ComplexesPhotoreceptor and optogenetics researchMolecular Sensors and Ion Detection