Development of a New Hydrogen Sulfide Fluorescent Probe Based on Coumarin–Chalcone Fluorescence Platform and Its Imaging Application

Hydrogen sulfide (H2S), as one of the critical gaseous signaling molecules, has important physiological functions in the human body, and abnormal levels of hydrogen sulfide are closely related to tumors, Parkinson’s disease, Alzheimer’s disease, and other diseases. In order to enable the detection of H2S in the physiological environment, herein, a new H2S fluorescence probe, named C-HS, based on a coumarin–chalcone fluorescence platform was developed. The fluorescence probe provides specific recognition of H2S within a wide pH detection range (5.5–8.5), a rapid recognition response (within 10 min) for H2S molecules, and a high selectivity for competing species. The probe C-HS possesses low cytotoxicity and is used to achieve the detection of exogenous/ endogenous H2S in living cells, indicating that the constructed probe C-HS has the ability to track changes in intracellular H2S levels. Therefore, probe C-HS could be a potential tool for the early diagnosis of H2S-related diseases.

[1]  Weiying Lin,et al.  Two Ratiometric Fluorescent Probes Based on the Hydroxyl Coumarin Chalcone Unit with Large Fluorescent Peak Shift for the Detection of Hydrazine in Living Cells. , 2022, Analytical chemistry.

[2]  Jibin Song,et al.  Ratiometric Detection of H2S in Liver Injury by Activated Two-Wavelength Photoacoustic Imaging. , 2022, Analytical chemistry.

[3]  Jiangyan Wang,et al.  Development of a Multi-Task Formaldehyde Specific Fluorescent Probe for Bioimaging in Living Systems and Decoration Materials Analysis , 2022, SSRN Electronic Journal.

[4]  Jiangyan Wang,et al.  An Activatable Photoacoustic Probe for Imaging Upregulation of Hydrogen Sulfide in Inflammation , 2022, SSRN Electronic Journal.

[5]  Ling Zhang,et al.  Photophysical properties and sensing mechanism of fluorescent coumarin–chalcone hybrid for biothiols: A theoretical study , 2022, Journal of Physical Organic Chemistry.

[6]  P. Viswanathamurthi,et al.  Dinitrobenzene ether reactive turn-on fluorescence probes for the selective detection of H2S. , 2021, Analytical methods : advancing methods and applications.

[7]  Junjie Yan,et al.  Small-molecule fluorescent probes for H2S detection: Advances and perspectives , 2020 .

[8]  Amrita Ghosh,et al.  Sensing and Bioimaging of the Gaseous Signaling Molecule Hydrogen Sulfide by Near-Infrared Fluorescent Probes. , 2020, ACS sensors.

[9]  Yonghong Hu,et al.  Novel turn-on fluorescence sensor for detection and imaging of endogenous H2S induced by sodium nitroprusside. , 2020, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[10]  Xi‐Cun Wang,et al.  A multifunctional fluorescent probe for highly selective detection of hydrazine and discovering the interplay between AIE and ICT , 2020 .

[11]  Yunping Liu,et al.  TDDFT study on the photophysical properties of coumarinyl chalcones and sensing mechanism of a derived fluorescent probe for hydrogen sulfide. , 2020, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[12]  Wencai Huang,et al.  The synthesis and bioimaging of a biocompatible hydrogen sulfide fluorescent probe with high sensitivity and selectivity. , 2020, The Analyst.

[13]  Zhen Qiao,et al.  A highly selective and sensitive fluorescent probe based on the chromone fluorophore for imaging hydrogen sulfide in living cells , 2020, New Journal of Chemistry.

[14]  Ben Zhong Tang,et al.  Assembly strategies of organic-based imaging agents for fluorescence and photoacoustic bioimaging applications. , 2019, Chemical Society reviews.

[15]  Yingsheng Cheng,et al.  J-aggregates of Cyanine Dye for NIR-II In-vivo Dynamic Vascular Imaging Beyond 1500 nm. , 2019, Journal of the American Chemical Society.

[16]  Yanping Hong,et al.  A NIR fluorescent probe for the detection and visualization of hydrogen sulfide in colorectal cancer cell , 2019, Sensors and Actuators B: Chemical.

[17]  Yongbin Zhang,et al.  An ICT lighten ratiometric and NIR fluorogenic probe to visualize endogenous/exogenous hydrogen sulphide and imaging in mice , 2019, Sensors and Actuators B: Chemical.

[18]  Weisheng Liu,et al.  A coumarin-based colorimetric fluorescent probe for rapid response and highly sensitive detection of hydrogen sulfide in living cells. , 2019, Talanta.

[19]  Qingyang Zhang,et al.  A fluorescent probe based on tetrahydro[5]helicene derivative with large Stokes shift for rapid and highly selective recognition of hydrogen sulfide. , 2019, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[20]  KeWei Wang,et al.  A highly sensitive and responsive fluorescent probe based on 6-azide-chroman dye for detection and imaging of hydrogen sulfide in cells. , 2019, Talanta.

[21]  Qingyun Liu,et al.  Recent advances in dual-emission ratiometric fluorescence probes for chemo/biosensing and bioimaging of biomarkers , 2019, Coordination Chemistry Reviews.

[22]  Ming-tao Run,et al.  A new turn-on fluorescent probe for the detection of palladium(0) and its application in living cells and zebrafish , 2019, New Journal of Chemistry.

[23]  Xiangzhi Song,et al.  Simultaneous Discrimination of Cysteine, Homocysteine, Glutathione, and H2S in Living Cells through a Multisignal Combination Strategy. , 2018, Analytical chemistry.

[24]  Songfang Zhao,et al.  Cyanide and biothiols recognition properties of a coumarin chalcone compound as red fluorescent probe. , 2018, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[25]  Weiying Lin,et al.  A novel red light emissive two-photon fluorescent probe for hydrogen sulfide (H2S) in nucleolus region and its application for H2S detection in zebrafish and live mice , 2018 .

[26]  Huibin Zhang,et al.  A near-infrared fluorescent probe based on nucleophilic substitution–cyclization for selective detection of hydrogen sulfide and bioimaging , 2017, Dyes and Pigments.

[27]  Ben Zhong Tang,et al.  AIE Luminogens for Bioimaging and Theranostics: From Organelles to Animals , 2017 .

[28]  Zhihong Liu,et al.  A ratiometric two-photon fluorescent probe for imaging hydrogen sulfide in lysosomes. , 2017, Talanta.

[29]  C. S. Lim,et al.  A two-photon fluorescent probe for specific detection of hydrogen sulfide based on a familiar ESIPT fluorophore bearing AIE characteristics. , 2017, Chemical communications.

[30]  Yue Wang,et al.  A reaction-based and highly selective fluorescent probe for hydrogen sulfide , 2017 .

[31]  Oh Seok Kwon,et al.  A near-infrared "turn-on" fluorescent probe with a self-immolative linker for the in vivo quantitative detection and imaging of hydrogen sulfide. , 2017, Biosensors & bioelectronics.

[32]  Tao Yi,et al.  pH-Dependent Fluorescent Probe That Can Be Tuned for Cysteine or Homocysteine. , 2017, Organic letters.

[33]  Wei Chen,et al.  A Single Fluorescent Probe to Visualize Hydrogen Sulfide and Hydrogen Polysulfides with Different Fluorescence Signals. , 2016, Angewandte Chemie.

[34]  Weiying Lin,et al.  A TICT-based fluorescent probe for rapid and specific detection of hydrogen sulfide and its bio-imaging applications. , 2016, Chemical communications.

[35]  Kyoung Chul Ko,et al.  Mitochondria-Targeted Reaction-Based Fluorescent Probe for Hydrogen Sulfide. , 2016, Analytical chemistry.

[36]  Jing Zhao,et al.  A highly selective and sensitive near-infrared fluorescent probe for imaging of hydrogen sulphide in living cells and mice , 2016, Scientific Reports.

[37]  Junfen Li,et al.  A ratiometric fluorescent probe for sensitive and selective detection of hydrogen sulfide and its application for bioimaging , 2015 .

[38]  Chen-Ho Tung,et al.  Design strategies of fluorescent probes for selective detection among biothiols. , 2015, Chemical Society reviews.

[39]  Wei Chen,et al.  Chemical probes for molecular imaging and detection of hydrogen sulfide and reactive sulfur species in biological systems. , 2015, Chemical Society reviews.

[40]  Hongyan Sun,et al.  A highly selective and sensitive fluorescent thiol probe through dual-reactive and dual-quenching groups. , 2015, Chemical communications.

[41]  Lingxin Chen,et al.  Fluorescent probes for hydrogen sulfide detection and bioimaging. , 2014, Chemical communications.

[42]  R. Martínez‐Máñez,et al.  Thiol-addition reactions and their applications in thiol recognition. , 2013, Chemical Society reviews.

[43]  Juyoung Yoon,et al.  Recent progress in luminescent and colorimetric chemosensors for detection of thiols. , 2013, Chemical Society reviews.

[44]  Wen Sun,et al.  A two-photon fluorescent probe with near-infrared emission for hydrogen sulfide imaging in biosystems. , 2013, Chemical communications.

[45]  Lin Qiu,et al.  A ratiometric fluorescent probe for rapid detection of hydrogen sulfide in mitochondria. , 2013, Angewandte Chemie.

[46]  K. Hanaoka,et al.  Development of a highly selective fluorescence probe for hydrogen sulfide. , 2011, Journal of the American Chemical Society.

[47]  Christopher J. Chang,et al.  Reaction-based fluorescent probes for selective imaging of hydrogen sulfide in living cells. , 2011, Journal of the American Chemical Society.

[48]  K. Ohkubo,et al.  Rational principles for modulating fluorescence properties of fluorescein. , 2004, Journal of the American Chemical Society.