Mitochondria-targetable fluorescent chemosensors, Rhodamine-B and rhodamine 6G bearing syringaldehyde based receptors were designed and synthesized for efficient chemosensing of Zinc(II) ions. The probes showed the very selective naked eye color change to pink from colorless upon addition of Zinc(II) ions, further these probes showing turn-on fluorescence enhancement with Zn(II) ions by opening of rhodamine spirolactam. The probes are very sensitive towards Zn(II) ions among other ions. These probes RBS and R6S will be applicable to detect zinc ions upto the low level concentration 0.18 and 0.19 nano molar respectively. The affinity of these sensors RBS and R6S for Zinc (II) ions was found to be in the range of 1.12 × 104 M-1 and 7.28 × 104 M-1 respectively. 1H-nmr titrations of the probes with Zn(II) ions clearly indicating the spiroring opening of the spirolactam. DFT calculations supporting that the perceived photophysical changes of the probes on appendage of the zinc ions. Probes RBS and R6S are useable for selective staining mitochondria. Both of the probes are applicable to reveal labile Zn(II) in live Hela and MCF-7 cells via fluorescence imaging. RBS and R6S are also finding application on quantification of Zinc(II) ions inside mitochondria via fluorescence imaging.
Keywords: Fluorescence; Imaging; Mitochondria; Rhodamine; Sensor; Zinc.
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