A new fluorescent turn-on chemodosimeter for mercury ions in solution and its application in cells and organisms.

Using the Hg(2+)-induced desulfurization reaction of thiosemicarbazide derivative, we designed and synthesized a novel "turn on" coumarin-based fluorescent probe L with a simple structure for detecting mercury ion (II). Spectroscopy revealed that the probe responds selectively to mercury ions over other metal ions with marked fluorescence enhancement. Detection of Hg(2+) was effective at pH 7.0-9.5, with high selectivity and significant effect in HeLa cells, human umbilical vein endothelial cells and Escherichia coli, but no cytotoxicity. This probe could be an ideal and practical Hg(2+) probe with important biological significance.

[1]  Weiping Zhu,et al.  Trace mercury (II) detection and separation in serum and water samples using a reusable bifunctional fluorescent sensor. , 2009, Analytica chimica acta.

[2]  Dandan Song,et al.  Layered titanate nanosheets as an enhanced sensing platform for ultrasensitive stripping voltammetric detection of mercury(II) , 2013 .

[3]  De-Sheng Mei,et al.  A simple selective protocol for continuous two-stage fluorescent sensing of both MeHg+ and anti-MeHg+ agents in living cells , 2012 .

[4]  C. Stalikas,et al.  A layered magnetic iron/iron oxide nanoscavenger for the analytical enrichment of ng-L(-1) concentration levels of heavy metals from water. , 2012, Analytica chimica acta.

[5]  Injae Shin,et al.  In vivo monitoring of mercury ions using a rhodamine-based molecular probe. , 2006, Journal of the American Chemical Society.

[6]  S. Ibeas,et al.  A selective and highly sensitive fluorescent probe of Hg2+ in organic and aqueous media: The role of a polymer network in extending the sensing phenomena to water environments , 2011 .

[7]  S. Gummadi,et al.  Biochemical evidence for lead and mercury induced transbilayer movement of phospholipids mediated by human phospholipid scramblase 1. , 2013, Chemical research in toxicology.

[8]  Minglei Zhao,et al.  A rhodamine-based Hg2+-selective fluorescent probe in aqueous solution , 2009 .

[9]  Chih-Ching Huang,et al.  Synthesis of photoluminescent Au ND-PNIPAM hybrid microgel for the detection of Hg2+. , 2013, ACS applied materials & interfaces.

[10]  F. Dumitrascu,et al.  Mesomorphic behaviour of N-benzoyl-N′-aryl thioureas liquid crystalline compounds , 2011 .

[11]  Meng Li,et al.  Turn-on fluorescent sensor for selective detection of Zn(2+), Cd(2+), and Hg(2+) in water. , 2012, The Journal of organic chemistry.

[12]  Chih-Ching Huang,et al.  Gold nanoparticle probes for the detection of mercury, lead and copper ions. , 2011, The Analyst.

[13]  A. Mahapatra,et al.  A new colorimetric chemodosimeter for mercury ion via specific thioacetal deprotection in aqueous solution and living cells , 2012 .

[14]  Chih-Ching Huang,et al.  Catalytic gold nanoparticles for fluorescent detection of mercury(II) and lead(II) ions. , 2012, Analytica chimica acta.

[15]  Hongkai Wu,et al.  Nanoporous gold based optical sensor for sub-ppt detection of mercury ions. , 2013, ACS nano.

[16]  X. Jia,et al.  Speciation of mercury in liquid cosmetic samples by ionic liquid based dispersive liquid–liquid microextraction combined with high-performance liquid chromatography-inductively coupled plasma mass spectrometry , 2011 .

[17]  B. Winblad,et al.  Relationship between mercury concentration in blood, cognitive performance, and blood pressure, in an elderly urban population , 2002, Biometals.

[18]  Yanmei Zhou,et al.  Highly selective fluorescence enhancement chemosensor for Hg2+ based on rhodamine and its application in living cells and aqueous media , 2013 .

[19]  Yuan Fang,et al.  A thiophen-thiooxorhodamine conjugate fluorescent probe for detecting mercury in aqueous media and living cells. , 2010, Organic & biomolecular chemistry.

[20]  Y. Lei,et al.  Fluorene‐based conjugated polymer with tethered thymines: click postpolymerization synthesis and optical response to mercury(II) , 2013 .

[21]  Zhong-Liang Gong,et al.  Synthesis, X-ray crystal structure and optical properties research of novel diphenyl sulfone-based bis-pyrazoline derivatives , 2012 .

[22]  Sung-Kyun Ko,et al.  Fluorescent detection of methylmercury by desulfurization reaction of rhodamine hydrazide derivatives. , 2009, Organic & biomolecular chemistry.

[23]  Juyoung Yoon,et al.  Rhodamine hydrazone derivatives bearing thiophene group as fluorescent chemosensors for Hg2 , 2013 .

[24]  T. James,et al.  A ditopic fluorescence sensor for saccharides and mercury based on a boronic-acid receptor and desulfurisation reaction. , 2011, Chemistry, an Asian journal.

[25]  Lingxin Chen,et al.  Highly sensitive and selective voltammetric detection of mercury(II) using an ITO electrode modified with 5-methyl-2-thiouracil, graphene oxide and gold nanoparticles , 2013, Microchimica Acta.

[26]  Huimin Ma,et al.  4-(8-Quinolyl)amino-7-nitro-2,1,3-benzoxadiazole as a new colorimetric probe for rapid and visual detection of Hg2+. , 2013, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[27]  Jae Jun Lee,et al.  A NBD-based selective colorimetric and fluorescent chemosensor for Hg2+ , 2013 .

[28]  A. Patra,et al.  Detection of Hg2+ and F- ions by using fluorescence switching of quantum dots in an Au-cluster-CdTe QD nanocomposite. , 2013, Chemistry.

[29]  R. Rossignol,et al.  Zebrafish: a model animal for analyzing the impact of environmental pollutants on muscle and brain mitochondrial bioenergetics. , 2013, The international journal of biochemistry & cell biology.

[30]  Anthony W. Czarnik,et al.  Fluorimetric chemodosimetry. Mercury(II) and silver(I) indication in water via enhanced fluorescence signaling , 1992 .

[31]  Xiaoling Zhang,et al.  A new rhodamine–chitosan fluorescent material for the selective detection of Hg2+ in living cells and efficient adsorption of Hg2+ in natural water , 2012 .

[32]  M. Balali-Mood,et al.  Mercury Contamination of Fish and Shrimp Samples Available in Markets of Mashhad, Iran , 2013, Bulletin of Environmental Contamination and Toxicology.

[33]  L. Alonso,et al.  Mercury, methylmercury, and selenium in blood of bird species from Doñana National Park (Southwestern Spain) after a mining accident , 2013, Environmental Science and Pollution Research.

[34]  Jing Liu,et al.  A naphthalimide–rhodamine ratiometric fluorescent probe for Hg2+ based on fluorescence resonance energy transfer , 2012 .

[35]  Y. Lei,et al.  Triphenylamine-based conjugated polymer/I− complex as turn-on optical probe for mercury(II) ion , 2013 .

[36]  G. Shen,et al.  Through bond energy transfer: a convenient and universal strategy toward efficient ratiometric fluorescent probe for bioimaging applications. , 2012, Analytical chemistry.

[37]  T W Clarkson,et al.  Methylmercury poisoning in Iraq. , 1973, Science.

[38]  C. Wade,et al.  Colorimetric turn-on sensing of fluoride ions in H2O/CHCl3 mixtures by pyridinium boranes. , 2009, Dalton transactions.

[39]  C. A. Roberts,et al.  Ratiometric fluorescence detection of mercury ions in water by conjugated polymer nanoparticles. , 2012, Analytical chemistry.

[40]  Juyoung Yoon,et al.  Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives. , 2012, Chemical reviews.

[41]  S. Adeloju,et al.  Speciation of mercury in fish samples by flow injection catalytic cold vapour atomic absorption spectrometry. , 2012, Analytica chimica acta.

[42]  J. Noh,et al.  Spacer dependency of the Hg2+-selective fluorescent signalling by desulfurization of thioamide as a turn-on switch , 2013 .

[43]  A Highly Sensitive and Selective Fluorescent Chemodosimeter for Hg2+ in Neutral Aqueous Solution , 2007, Journal of Fluorescence.

[44]  J. Leaner,et al.  Photoelectrochemical determination of inorganic mercury in aqueous solutions. , 2010, Analytica chimica acta.

[45]  Yuqing Wu,et al.  A highly selective fluorescent sensor for mercury ions in aqueous solution: Detection based on target-induced aggregation , 2010 .

[46]  I. Dumazet-Bonnamour,et al.  Electrochemical analysis of a PPV derivative thin film doped with ß-ketoimine calix[4]arene in the dark and under illumination for the detection of Hg2+ ions , 2013 .

[47]  Meng Zhang,et al.  Three-dimensional paper-based electrochemiluminescence device for simultaneous detection of Pb2+ and Hg2+ based on potential-control technique. , 2013, Biosensors & bioelectronics.

[48]  H. Katerinopoulos,et al.  A "turn-on" coumarin-based fluorescent sensor with high selectivity for mercury ions in aqueous media. , 2010, Chemical communications.

[49]  M. Xian,et al.  Reaction based fluorescent probes for hydrogen sulfide. , 2012, Organic letters.

[50]  M. Machida,et al.  Screening search for organic fluorophores: syntheses and fluorescence properties of 3-azolyl-7-diethylaminocoumarin derivatives. , 2000, Chemical & pharmaceutical bulletin.

[51]  Anup Kumar,et al.  Benzimidazole-based optical probe for selective detection of multiple-cations via dual-channel analysis , 2012 .

[52]  N. Hara,et al.  Lower urinary tract symptoms in patients with Niigata Minamata disease: A case–control study 50 years after methyl mercury pollution , 2013, International journal of urology : official journal of the Japanese Urological Association.

[53]  Lok Nath Neupane,et al.  Turn-on fluorescent chemosensor based on an amino acid for Pb(II) and Hg(II) ions in aqueous solutions and role of tryptophan for sensing. , 2013, Organic letters.

[54]  J. Roy,et al.  Hg2+-selective “turn-on” fluorescent chemodosimeter derived from glycine and living cell imaging , 2012 .

[55]  G. Shen,et al.  A highly selective fluorescent probe for Hg(2+) based on a rhodamine-coumarin conjugate. , 2010, Analytica chimica acta.

[56]  Jun-Ying Miao,et al.  Fluorescence turn-on chemodosimeter for rapid detection of mercury (II) ions in aqueous solution and blood from mice with toxicosis. , 2013, Analytica chimica acta.

[57]  C. Carasco,et al.  Prompt gamma neutron activation analysis of toxic elements in radioactive waste packages. , 2012, Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine.

[58]  Leah E. Page,et al.  Detection of toxic mercury ions using a ratiometric CdSe/ZnS nanocrystal sensor. , 2011, Chemical communications.

[59]  Q. Guo,et al.  Highly sensitive and selective fluorescent chemosensors for Hg(II) in an aqueous environment based on carbamodithioate , 2006 .

[60]  B. Tang,et al.  A Sensitive and Selective Near‐Infrared Fluorescent Probe for Mercuric Ions and Its Biological Imaging Applications , 2008, Chembiochem : a European journal of chemical biology.

[61]  Wenhui Ma,et al.  A Hg2+-selective chemodosimeter based on desulfurization of coumarin thiosemicarbazide in aqueous media. , 2010, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[62]  A. Kulkarni,et al.  Synthesis, characterization, DNA cleavage and in vitro antimicrobial studies of La(III), Th(IV) and VO(IV) complexes with Schiff bases of coumarin derivatives. , 2009, European journal of medicinal chemistry.

[63]  Hao Wang,et al.  Spiropyran-based optical approaches for mercury ion sensing: improving sensitivity and selectivity via cooperative ligation interactions using cysteine. , 2009, Analytica chimica acta.

[64]  S. Tanabe,et al.  Mercury contamination in human hair and fish from Cambodia: levels, specific accumulation and risk assessment. , 2005, Environmental pollution.

[65]  Jinming Hu,et al.  Hg2+-reactive double hydrophilic block copolymer assemblies as novel multifunctional fluorescent probes with improved performance. , 2010, Langmuir : the ACS journal of surfaces and colloids.

[66]  Sundargopal Ghosh,et al.  Sensitive and selective redox, chromogenic, and "turn-on" fluorescent probe for Pb(II) in aqueous environment. , 2013, Analytical chemistry.

[67]  Xingjiu Huang,et al.  High adsorptive γ-AlOOH(boehmite)@SiO2/Fe3O4 porous magnetic microspheres for detection of toxic metal ions in drinking water. , 2011, Chemical communications.

[68]  Deqing Zhang,et al.  A sensitive and selective “turn on” fluorescent chemosensor for Hg(II) ion based on a new pyrene–thymine dyad , 2005 .

[69]  Jianping Xie,et al.  Highly selective and ultrasensitive detection of Hg(2+) based on fluorescence quenching of Au nanoclusters by Hg(2+)-Au(+) interactions. , 2010, Chemical communications.

[70]  W. Tseng,et al.  Ultrasensitive sensing of Hg(2+) and CH(3)Hg(+) based on the fluorescence quenching of lysozyme type VI-stabilized gold nanoclusters. , 2010, Analytical chemistry.