Design and Synthesis of a Dinuclear Copper(II) Probe for Selective Fluorescence Sensing of Pyrophosphate

A novel coumarin-based compound DPAC with two dipicolylamine (DPA) arms as the chelator sites was designed and synthesized. The compound DPAC exhibits a highly selective response to Cu2+ ions with a distinctly emission-quenching phenomenon. Moreover, the in situ formed complex DPAC-Cu2+ was used for the detection of pyrophosphate (PPi). The binding manner of probe DPAC-Cu2+ with PPi in 1 : 1 stoichiometry was supported by the Benesi-Hildebrand fitting, ESI-MS and HPLC analysis. The linear range of PPi concentration was 1-4 μM, and the detection limit was 0.53 μM. The competing experiments illustrated that the probe DPAC-Cu2+ had good sensitivity and selectivity for PPi than other anions, including ATP, ADP, AMP, and Pi in CH3CN : HEPES (3 : 2, v/v, pH=7.20) buffer. Further, cell fluorescence imaging experiments indicated that the probe DPAC-Cu2+ had a potential to be used to detect PPi in vivo.

[1]  Linlin Yang,et al.  Synthesis and application of a highly selective copper ions fluorescent probe based on the coumarin group. , 2018, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[2]  S. Kubik.  Anion Recognition in Aqueous Media by Cyclopeptides and Other Synthetic Receptors. , 2017, Accounts of chemical research.

[3]  Xiaobo Liu,et al.  Design and synthesis of a fluorescent probe based on naphthalene anhydride and its detection of copper ions , 2017, PloS one.

[4]  Cuiling Zhang,et al.  Label-free upconversion nanoparticles-based fluorescent probes for sequential sensing of Cu2+, pyrophosphate and alkaline phosphatase activity. , 2017, Biosensors & bioelectronics.

[5]  P. Anzenbacher,et al.  Biguanides, anion receptors and sensors. , 2017, Chemical communications.

[6]  K. Jolliffe.  Pyrophosphate Recognition and Sensing in Water Using Bis[zinc(II)dipicolylamino]-Functionalized Peptides. , 2017, Accounts of chemical research.

[7]  Feng Gao,et al.  Ratiometric detection of copper ions and alkaline phosphatase activity based on semiconducting polymer dots assembled with rhodamine B hydrazide. , 2017, Biosensors & bioelectronics.

[8]  P. Iyer,et al.  An efficient strategy to assemble water soluble histidine-perylene diimide and graphene oxide for the detection of PPi in physiological conditions and in vitro. , 2017, Biosensors & bioelectronics.

[9]  Dingbin Liu,et al.  Live-Cell Pyrophosphate Imaging by in Situ Hot-Spot Generation. , 2017, Analytical chemistry.

[10]  A. Ojida,et al.  Fluorescence Sensing of Inorganic Phosphate and Pyrophosphate Using Small Molecular Sensors and Their Applications , 2017, Topics in Current Chemistry.

[11]  Qingzhi Wang,et al.  Synthesis of a fluorogenic probe for thiols based on a coumarin schiff base copper complex and its use for the detection of glutathione , 2017 .

[12]  K. Aguan,et al.  Ruthenium(II) Complex-Based Luminescent Bifunctional Probe for Ag+ and Phosphate Ions: Ag+-Assisted Detection and Imaging of rRNA. , 2017, Inorganic chemistry.

[13]  Hong-Cheu Lin,et al.  Facile rhodamine-based colorimetric sensors for sequential detections of Cu(II) ions and pyrophosphate (P2O74−) anions , 2016 .

[14]  Guimei Wang,et al.  A near-infrared squaraine dye for cascade recognition of copper ion and biological phosphate and its application in IMPLICATION logic gate , 2016 .

[15]  Wei Chen,et al.  Water-soluble gold nanoclusters prepared by protein-ligand interaction as fluorescent probe for real-time assay of pyrophosphatase activity. , 2016, Biosensors & bioelectronics.

[16]  Xin Wu,et al.  Copper-Mediated DNA-Scaffolded Silver Nanocluster On-Off Switch for Detection of Pyrophosphate and Alkaline Phosphatase. , 2016, Analytical chemistry.

[17]  B. Liu,et al.  A novel flavonoid-based bioprobe for intracellular recognition of Cu2+ and its complex with Cu2+ for secondary sensing of pyrophosphate , 2016 .

[18]  Peng Zhou,et al.  A new copper(II) selective fluorescence probe based on naphthalimide: Synthesis, mechanism and application in living cells , 2016 .

[19]  M. Berberan-Santos,et al.  Dinuclear Zinc(II) Macrocyclic Complex as Receptor for Selective Fluorescence Sensing of Pyrophosphate. , 2016, Inorganic chemistry.

[20]  R. Montis,et al.  Fluorescent asymmetric bis-ureas for pyrophosphate recognition in pure water. , 2016, Dalton transactions.

[21]  P. Beer,et al.  Anion Recognition in Water: Recent Advances from a Supramolecular and Macromolecular Perspective , 2015, Angewandte Chemie.

[22]  Philip A. Gale,et al.  Anion sensing by small molecules and molecular ensembles. , 2015, Chemical Society reviews.

[23]  K. Jolliffe,et al.  Fluorescent and colorimetric chemosensors for pyrophosphate. , 2015, Chemical Society reviews.

[24]  R. Nandhakumar,et al.  Multi-analyte, ratiometric and relay recognition of a 2,5-diphenyl-1,3,4-oxadiazole-based fluorescent sensor through modulating ESIPT , 2015 .

[25]  Xiaoqiang Chen,et al.  Ammonium-bearing dinuclear copper(II) complex: a highly selective and sensitive colorimetric probe for pyrophosphate. , 2014, Organic letters.

[26]  P. Zhou,et al.  A simple click generated probe for highly selective sequential recognition of Cu(II) and pyrophosphate , 2013 .

[27]  Nellore Bhanu Chandar,et al.  Role of metal ion in specific recognition of pyrophosphate ion under physiological conditions and hydrolysis of the phosphoester linkage by alkaline phosphatase. , 2013, Inorganic chemistry.

[28]  R. C. Deka,et al.  A New On-fluorescent Probe for Manganese (II) Ion , 2013, Journal of Fluorescence.

[29]  K. Jolliffe,et al.  Anion recognition and sensing with Zn(II)-dipicolylamine complexes. , 2012, Chemical Society reviews.

[30]  H. Tian,et al.  A novel NIR fluorescent turn-on sensor for the detection of pyrophosphate anion in complete water system. , 2012, Chemical communications.

[31]  K. Ahn,et al.  Mononuclear Zn(II)- and Cu(II)-complexes of a hydroxynaphthalene-derived dipicolylamine: fluorescent sensing behaviours toward pyrophosphate ions. , 2011, Organic & biomolecular chemistry.

[32]  Qingbiao Yang,et al.  Layer-by-layer assembled Fe3O4@C@CdTe core/shell microspheres as separable luminescent probe for sensitive sensing of Cu2+ ions. , 2011, Langmuir : the ACS journal of surfaces and colloids.

[33]  Jong Seung Kim,et al.  An iminocoumarin-Cu(II) ensemble-based chemodosimeter toward thiols. , 2011, Chemical communications.

[34]  Bradley D. Smith,et al.  In vivo targeting of cell death using a synthetic fluorescent molecular probe , 2011, Apoptosis.

[35]  Jae-Hoon Jung,et al.  A highly selective and sensitive fluorescence sensing system for distinction between diphosphate and nucleoside triphosphates. , 2011, The Journal of organic chemistry.

[36]  W. M. Leevy,et al.  Optical imaging of mammary and prostate tumors in living animals using a synthetic near infrared zinc(II)-dipicolylamine probe for anionic cell surfaces. , 2010, Journal of the American Chemical Society.

[37]  Juyoung Yoon,et al.  Pyrophosphate selective fluorescent chemosensors based on coumarin-DPA-Cu(II) complexes. , 2009, Chemical communications.

[38]  Hiroshi Nonaka,et al.  Turn-on fluorescence sensing of nucleoside polyphosphates using a xanthene-based Zn(II) complex chemosensor. , 2008, Journal of the American Chemical Society.

[39]  Sung-Jin Kim,et al.  Pyrophosphate-selective fluorescent chemosensor at physiological pH: formation of a unique excimer upon addition of pyrophosphate. , 2007, Journal of the American Chemical Society.

[40]  W. Matthew Leevy,et al.  Optical imaging of bacterial infection in living mice using a fluorescent near-infrared molecular probe. , 2006, Journal of the American Chemical Society.

[41]  Christopher J. Chang,et al.  A FRET-based approach to ratiometric fluorescence detection of hydrogen peroxide. , 2006, Journal of the American Chemical Society.

[42]  Philip A. Gale,et al.  Anion Receptor Chemistry , 2006 .

[43]  G. Burnstock.  Pathophysiology and Therapeutic Potential of Purinergic Signaling , 2006, Pharmacological Reviews.

[44]  Alexander V. Gourine,et al.  ATP is a mediator of chemosensory transduction in the central nervous system , 2005, Nature.

[45]  Bradley D. Smith,et al.  Fluorophore-linked zinc(II)dipicolylamine coordination complexes as sensors for phosphatidylserine-containing membranes , 2004 .

[46]  P. Quinn,et al.  Design, synthesis, physicochemical properties, and evaluation of novel iron chelators with fluorescent sensors. , 2004, Journal of medicinal chemistry.

[47]  Jong‐In Hong,et al.  An azophenol-based chromogenic pyrophosphate sensor in water. , 2003, Journal of the American Chemical Society.

[48]  M. Ronaghi,et al.  Real-time DNA sequencing using detection of pyrophosphate release. , 1996, Analytical biochemistry.

[49]  A. Jones,et al.  Association between synovial fluid levels of inorganic pyrophosphate and short term radiographic outcome of knee osteoarthritis. , 1996, Annals of the rheumatic diseases.