"Lighting up" fluoride: cellular imaging and zebrafish model interrogations using a simple ESIPT-based mycophenolic acid precursor-based probe.

The discovery and implementation of media that derive from bioinspired designs and bear optical readouts featuring large Stokes shifts are of continued interest to a wide variety of researchers and clinicians. Myco-F, a novel mycophenolic acid precursor-based probe features a cleavable tert-butyldimethylsiloxy group to allow for fluoride detection. Myco-F exhibits high selectivity and specificity towards F- (Stokes shift = 120 nm). All measurements were performed in complete aqueous media (LOD=0.38 μM). Myco-F enables detection of fluoride ions in living HEK293 cells and localizes in the eye region (among other regions) of the zebrafish. DFT calculations support the proposed ESIPT working photomechanism.

[1]  Hong Wang,et al.  Highly Specific and Sensitive Naked-Eye Fluoride Ion Recognition via Unzipping a Helical Poly(phenylacetylene) , 2022, Macromolecules.

[2]  L. Wang,et al.  A deep-red emission fluorescent probe for visualization of fluoride anion accumulation in a murine model of acute fluoride toxicity and the roots of Arabidopsis thaliana , 2022, Sensors and Actuators B: Chemical.

[3]  Cheol‐Hee Kim,et al.  Phosphinate-benzoindocyanin fluorescent probe for endogenous mitochondrial peroxynitrite detection in living cells and gallbladder access in inflammatory zebrafish animal models. , 2021, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[4]  M. Selvaraj,et al.  A novel indolehydrazone appended salicyaldehyde platform for detection of multianalytes (Al3+, Zn2+ and F- ions): Live cell imaging , 2021, Inorganic Chemistry Communications.

[5]  Y. Mary,et al.  Theoretical model study of adsorbed antimalarial-graphene dimers: doping effects, photophysical parameters, intermolecular interactions, edge adsorption, and SERS , 2021, Journal of biomolecular structure & dynamics.

[6]  Juhyeon Kim,et al.  A water-soluble boronate masked benzoindocyanin fluorescent probe for the detection of endogenous mitochondrial peroxynitrite in live cells and zebrafish as inflammation models , 2021, Dyes and Pigments.

[7]  Cuiping Ma,et al.  A novel ICT-based chemosensor for F- and its application in real samples and bioimaging. , 2021, Journal of hazardous materials.

[8]  D. Churchill,et al.  Discussions of Fluorescence in Selenium Chemistry: Recently Reported Probes, Particles, and a Clearer Biological Knowledge † , 2021, Molecules.

[9]  Yongqing Li,et al.  Theoretical insights into ESIPT mechanism of the two protons system BH-BA in dichloromethane solution , 2020 .

[10]  V. Patial,et al.  Zebrafish: An emerging model system to study liver diseases and related drug discovery , 2020, Journal of applied toxicology : JAT.

[11]  S. Pramanik,et al.  Correction to Small Molecule as Fluorescent Probes for Monitoring Intracellular Enzymatic Transformations. , 2020, Chemical reviews.

[12]  Zhihua Zhou,et al.  Symmetrical bis-salophen probe serves as a selectively and sensitively fluorescent switch of gallium ions in living cells and zebrafish. , 2019, Talanta.

[13]  Lauren M. Saunders,et al.  A Single-Cell Transcriptome Atlas for Zebrafish Development , 2019, bioRxiv.

[14]  D. Churchill,et al.  Mycophenolic Acid: Biogenesis, Compound Isolation, Biological Activity, and Historical Advances in Total Synthesis , 2019, European Journal of Organic Chemistry.

[15]  S. Velmathi,et al.  Phenazine-Based Fluorescence “Turn-Off” Sensor for Fluoride: Application on Real Samples and to Cell and Zebrafish Imaging , 2019, ChemistrySelect.

[16]  Yi Zhou,et al.  Fluorescence turn-on detection of fluoride using HPQ-silyl ether reactive probes and its in vivo application , 2018, Dyes and Pigments.

[17]  D. Churchill,et al.  Overriding Phthalate Decomposition When Exploring Mycophenolic Acid Intermediates as Selenium-Based ROS Biological Probes , 2018, ACS omega.

[18]  Xingbin Yang,et al.  In Vivo Fluoride Ion Detection and Imaging in Mice Using a Designed Near-Infrared Ratiometric Fluorescent Probe Based on IR-780. , 2018, Journal of agricultural and food chemistry.

[19]  Xinghua Wang,et al.  A novel fluorescein-coumarin-based fluorescent probe for fluoride ions and its applications in imaging of living cells and zebrafish in vivo , 2018, Sensors and Actuators B: Chemical.

[20]  D. Churchill,et al.  Diels-Alder and Stille Coupling Approach for the Short Protecting-Group-Free Synthesis of Mycophenolic Acid, Its Phenylsulfenyl and Phenylselenyl Analogues, and Reactive Oxygen Species (ROS) Probing Capacity in Water. , 2018, Organic letters.

[21]  Yongqing Li,et al.  Theoretical Study of the ESIPT Process for a New Natural Product Quercetin , 2016, Scientific Reports.

[22]  Pinaki Talukdar,et al.  A cascade reaction based fluorescent probe for rapid and selective fluoride ion detection. , 2014, Chemical communications.

[23]  Fang Zeng,et al.  A PEGylated fluorescent turn-on sensor for detecting fluoride ions in totally aqueous media and its imaging in live cells. , 2013, Chemistry.

[24]  B. Key,et al.  HuC–eGFP mosaic labelling of neurons in zebrafish enables in vivo live cell imaging of growth cones , 2012, Journal of Molecular Histology.

[25]  P. Grandjean,et al.  Developmental Fluoride Neurotoxicity: A Systematic Review and Meta-Analysis , 2012, Environmental health perspectives.

[26]  Chang-Hee Lee,et al.  Highly sensitive fluorescence "turn-on" indicator for fluoride anion with remarkable selectivity in organic and aqueous media. , 2011, The Journal of organic chemistry.

[27]  C. Wade,et al.  Fluoride ion complexation and sensing using organoboron compounds. , 2010, Chemical reviews.

[28]  K. Paeng,et al.  Determination of Fluoride in Water by Reversed-Phase High-Performance Liquid Chromatography using F−-La3+-Alizarin Complexone Ternary Complex , 2004 .

[29]  T. Swager,et al.  A fluorescent self-amplifying wavelength-responsive sensory polymer for fluoride ions. , 2003, Angewandte Chemie.

[30]  J. Namieśnik,et al.  Comparison of Fluoride Ion-Selective Electrode Based Potentiometric Methods of Fluoride Determination in Human Urine , 2000, Bulletin of environmental contamination and toxicology.

[31]  P. He,et al.  Dose-effect relationship between drinking water fluoride levels and damage to liver and kidney functions in children. , 2007, Environmental research.