Co-reporter:Fangjun Huo, Yaqiong Zhang, Jin Kang, Jianbin Chao, Yongbin Zhang, Caixia Yin
Sensors and Actuators B: Chemical 2017 Volume 243() pp:429-434
Publication Date(Web):May 2017
DOI:10.1016/j.snb.2016.11.034
•The fluorescent sensor was the first alkyne fluorescent probe with excellent water-solubility for the detection of Pd2+.•The mechanism via catalytic-depropargylation to form oxime.•This probe also could be used to bioimaging.Palladium is significant in chemistry, biology and environmental science, while as a toxic metal, it could have adverse effects on our health and the environment. It is thus critical to monitor the changes of Pd (II) in living cells. Here, we developed a new colorimetric and fluorometric probe (TP1) based on palladium(II)-involved reactivity. Compared with the reported Pd (II) sensors, TP1 was the first alkyne compound fluorescent probe with excellent water-solubility for Pd2+, which was via catalytic-depropargylation to form oxime for the detection of Pd2+ within a rapid response time 80 s. The detection limit of TP1 toward Pd(II) was estimated as 0.47 μM. In addition, the ability of the TP1 to detect Pd(II) in living cells (HepG2 cells) has been also proven. These results indicated that TP1 was a highly sensitive turn-off Pd(II) dye with promising biological applications.A new fluorescent prob e for Pd2+ based on triphenylamine was developed. Among the tested metal ions, only Pd2+ could turn off the fluorescence intensity suggesting that the probe was a highly selective sensor for Pd2+. More importantly, the probe featured a rapid signal response time (within 80 s). In addition, the ability of the probe to detect Pd(II) in living cells (HepG2 cells) via quenching of the fluorescence had also been proved.
Co-reporter:Huifang Zhang, Tao Liu, Caixia Yin, Yin Wen, Jianbin Chao, Yongbin Zhang, Fangjun Huo
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2017 Volume 174() pp:230-235
Publication Date(Web):5 March 2017
DOI:10.1016/j.saa.2016.11.039
•The compound is the first ratiometric fluorescent probe for the detection of Ho3 +.•The probe exhibits a lower detection limit (6 × 10− 8 M).•Its potential application in bioimaging was also illustrated.A ratiometric fluorescent probe for the detection of Ho3 + in DMSO-aqueous medium was designed and synthesized based on 1, 8-naphthalimide. The probe displayed response to Ho3 + with a fluorescence decrease at 512 nm and enhancement at 480 nm, accompanying with a distinct fluorescence change from bright yellow-green to cyan. Besides, the probe exhibited a lower detection limit (6 × 10− 8 M) and could be used in intracellular fluorescence imaging. To the best of the knowledge, it was the first ratiometric fluorescent probe for Ho3 + detection. This probe was expected to be a useful tool for further elucidating the roles of Ho3 + in materials, biology and environment.Based on the coordination reaction between probe and Ho3+ under mild conditions, we herein report the first ratiometric fluorescent probe which features a rapid signal response time (within 200 s), a good linearity range and a low detection limit (6 × 10− 8M). The potential application of this ratiometric fluorescent probe was demonstrated by fluorescent imaging in living cells.
Co-reporter:Jiawei Li, Tao Liu, Fangjun Huo, Jianbin Chao, Yongbin Zhang, Caixia Yin
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2017 Volume 174() pp:17-24
Publication Date(Web):5 March 2017
DOI:10.1016/j.saa.2016.11.019
•Two probes had excellent sensitivity and high selectivity for ClO−.•The recognition mechanisms were studied confirmed by density functional theory calculations.•Two probes in practical application was demonstratedTwo simple, efficient turn-on fluorescent probes for hypochlorite have been rationally designed and developed by utilizing the oxidation of hypochlorite. Notably, probe 1 and 2 displayed rapid and remarkable turn-on responses to ClO− in PBS buffer solution (pH 7.4). Further, the optical properties of two probes and their ClO−-addition products were confirmed by density functional theory calculations. And detection limits of two probes for ClO− based on the definition by IUPAC were calculated for 2.882 nM and 0.354 μM. More importantly, cell imaging experiments demonstrated that probe 1 was more suitable for detecting the ClO− in living A549 cells. And both two probes had the possibility of potentially applied in practical applications such as detecting the hypochlorite concentration of tap water and river water.In this study, two efficient turn-on fluorescent probes based on 1, 8-Naphthalimide for hypochlorite have been rationally devised and constructed. The detection limits of probe 1 and 2 for ClO− were calculated for 2.882 nM and 0.354 μM. Moreover, the optical properties of two probes and their ClO−-addition products were confirmed by density functional theory calculations. And both two probes had the possibility of potentially applied in practical applications such as detecting the hypochlorite concentration of tap water and river water.
Co-reporter:Huifang zhang, Caixia Yin, Tao Liu, Jianbin Chao, Yongbin Zhang, Fangjun Huo
Dyes and Pigments 2017 Volume 146(Volume 146) pp:
Publication Date(Web):1 November 2017
DOI:10.1016/j.dyepig.2017.07.033
•The probe is a novel fluorescent probe for the detection of Mg2+ with a 2: 1 coordination between probe and Mg2+.•The probe showed a low detection limit 5.01 × 10−8 M and 45 s response time for Mg2+ detection.•The probe is nearly non-toxic and could be applied in bioimaging.A novel “off-on” fluorescent probe based on 1, 8-naphthalimide derivative for the detection of Mg2+ in ethanol solution was designed and synthesized. The probe displayed responses to Mg2+ with a fluorescence enhancement at 523 nm, accompanying with a distinct fluorescence change from nearly colorless to bright yellow-green. Besides, the probe showed a rapid detection process (45 s), high fluorescence enhancement (up to 15-fold), a good binding constant (6.17 × 105 M−1) and a low detection limit of Mg2+ (5.01 × 10−8 M). Moreover, density functional theory (DFT) calculations were also performed to support the responding mechanism between the probe and the coordination complex. In addition, the cell cytotoxicity experiments suggested that the probe is nearly non-toxic and the fluorescence scanning microscopic experiments demonstrated that the probe was capable of monitoring at the intracellular Mg2+ level successfully.Download high-res image (157KB)Download full-size image
Co-reporter:Fangjun Huo, Yaqiong Zhang, Yongkang Yue, Jianbin Chao, Yongbin Zhang, Caixia Yin
Dyes and Pigments 2017 Volume 143(Volume 143) pp:
Publication Date(Web):1 August 2017
DOI:10.1016/j.dyepig.2017.04.050
•A novel ratiometric fluorescent chemodosimeter for selective detection of cyanide was obtained.•The probe showed a long emission wavelengths (>600 nm) and relatively large Stokes shifts (>100 nm).•This probe also could be used to bioimaging.A new red-emitting fluorescent materials (EP1) has been designed by taking consideration of the typical asymmetrical π-conjugation structure of the isophorone skeleton, which showed a special nucleophilicity for cyanide ion. The novel probe EP1 using an isophorone-based aldehyde as color reporting group to detect CN−, which was the first time to put forward this skeleton as new color reporting group to detect analytes in the library of chemsensor. Moreover, this new saturated red-emitting fluorescent probe with a typical donor-π-acceptor structure to detect CN− was by hampered ESIPT effect, which had a prominent fluorescence “ratiometric” changes accompanied with a large stokes shifts around 150 nm. In addition, the ability of this unique probe to detect cyanide anion in living cells (A549 cells) had also been proved. These results indicated that EP1 was a highly sensitive “ratiometric” dye with promising biological applications.Download high-res image (220KB)Download full-size image
Co-reporter:Jin Kang, Fangjun Huo, Caixia Yin
Dyes and Pigments 2017 Volume 146(Volume 146) pp:
Publication Date(Web):1 November 2017
DOI:10.1016/j.dyepig.2017.07.016
•A ratiometric fluorescent probe for detection of H2S was prepared.•The fluorescent probe displayed excellent water solubility.•The fluorescent probe with biocompatibility can detect endogenous H2S in living cells.The third gasotransmitter hydrogen sulfide (H2S) plays a vital role to human health and diseases. A water-soluble ratiometric fluorescent probe (HS-1) for hydrogen sulfide (H2S) has been developed, which resulted in an increase of the emission at 403 nm along with a concomitant decrease of fluorescence peak at 519 nm, the ratios of emission intensities at 403 and 519 nm (I403/I519) displayed an increase from 0.27 to 8.54. This probe showed excellent selectivity toward H2S over other common anions and biothiols. Furthermore, these successes of intracellular imaging experiments in A549 cells indicated that this probe is suitable for imaging of ex-/endogenous hydrogen sulfide in living cells.A novel fluorescence H2S probe based on tandem nucleophilic substitution/cyclization reaction was obtained, which is a ratiometric fluorescent probe possessing good water solubility, membrane permeability, and compatibility with living cells for selective detection of ex-/endogenous H2S in living cells.Download high-res image (263KB)Download full-size image
Co-reporter:Xiaoqi Li, Fangjun Huo, Yongkang Yue, Yongbin Zhang, Caixia Yin
Sensors and Actuators B: Chemical 2017 Volume 253(Volume 253) pp:
Publication Date(Web):1 December 2017
DOI:10.1016/j.snb.2017.06.120
•A new “off-on” sensor which can fluorescence discriminate GSH from Cys/Hcy at intracellular concentrations.•The significantly different mechanisms enable the discrimination of GSH over Cys/Hcy through fluorescence response.•The probe has a good cell membrane permeability that can be applied in bioimaging in living cells.Glutathione (GSH) is the most abundant intracellular thiol with the concentration in the millimolar range. It has also been reported that GSH plays a crucial role in human pathologies, so it is meaningful to develop an effective probe for GSH. In this work, we report a coumarin-chlorine malononitrile “off-on” sensor for highly selective fluorescence detection of GSH over Cys/Hcy. The chlorine of the probe can be rapidly replaced by thiolates of biothiols through thiol-halogen nucleophilic substitution. The amino groups of Cys/Hcy but not GSH further replace the thiolate to form amino-substituted compound. Subsequently, an intramolecular Michael addition between the α,β-unsaturated malonitrile and thiol group may occur. However, GSH only forms thiol-substituted compound. The significantly different mechanisms enable the discrimination of GSH over Cys/Hcy through fluorescence response. Finally, fluorescence imaging of A549 cells indicated that probe 1 could be used for monitoring GSH in living cells. It would be a useful tool to understand the mechanisms of many related diseases.The statement: A coumarin-based “off-on” sensor was designed and synthesized, which was able to fluorescence selectivily discriminate GSH from Cys/Hcy. The significantly different mechanisms enable the discrimination of GSH over Cys/Hcy through fluorescence response. Finally, fluorescence imaging of A549 cells indicated that 1 could be used for monitoring GSH in living cells.Download high-res image (85KB)Download full-size image
Co-reporter:Jin Kang, Fangjun Huo, Peng Ning, Xiangming Meng, Jianbin Chao, Caixia Yin
Sensors and Actuators B: Chemical 2017 Volume 250(Volume 250) pp:
Publication Date(Web):1 October 2017
DOI:10.1016/j.snb.2017.04.180
•Two red-emission fluorescent probes were synthesized by a ‘one-pot’ reaction.•We concentrated on the comparative investigation on two probes abilities for H2S.•The long-emission probe can be used to imaging endogenous H2S using S-Nitroso-N-acetyl-DL- penicillamine (SNP) stimulating in cells and zebrafish.The gasotransmitter hydrogen sulfide (H2S) has attracted attention in recent years for its contributions to human health and diseases. In this work, the design strategy relied on ‘one-pot’ by employing BODIPY 1 dye and P-hydroxybenzaldehyde afforded two key intermediates, then further reacted with NBD thus obtaining products ‘single’ and ‘double’ arms types molecules (BDP-N1 and BDP-N2). Firstly we concentrated on the comparative investigation their response abilities for hydrogen sulfide. The response mechanisms are all based on the selective thiolysis of 7-nitrobenzo[c-1,2,5] oxadiazole(NBD) moiety attached to the styryl-BODIPY scaffold by H2S. However, it is worth mentioned that double‘arms’showed longer wavelength excitation and emission resulting from extended conjugation. Furthermore, these successes of intracellular imaging experiments in A549 cells indicated that the two probes are suitable for imaging of exogenous or endogenous hydrogen sulfide in living cells or living zebrafish.
Co-reporter:Fangjun Huo;Yaqiong Zhang;Peng Ning;Xiangming Meng;Caixia Yin
Journal of Materials Chemistry B 2017 vol. 5(Issue 15) pp:2798-2803
Publication Date(Web):2017/04/12
DOI:10.1039/C7TB00299H
The sulfide anion is significant in industrial processes, biology and environmental science. Hence, robust fluorescent sensors for sulfide which are water soluble and biocompatible are highly desirable. Here, we developed a novel red-emitting fluorescent probe (SP1) for the sulfide anion based on cleaving the dinitrobenzenesulfonate ester to restore the fluorescence, accompanied by a long wavelength emission at 644 nm. The detection process took place in 100% PBS buffer, which suggested it had excellent water solubility. Most importantly, the ability of SP1 to detect sulfide anions in living cells (MCF-7 cells) and zebrafish has also been proven.
Co-reporter:Xiaoqi Li, Yongkang Yue, Yin Wen, Caixia Yin, Fangjun Huo
Dyes and Pigments 2016 Volume 134() pp:291-296
Publication Date(Web):November 2016
DOI:10.1016/j.dyepig.2016.07.033
•The probe displayed excellent water solubility which could detect pH in aqueous solution.•The probe can be applied in bioimaging in living cells.•The distinct color changes promoted probe to be used for precise pH paper preparation.To obtain a better insight into the physiological and pathological functions of pH, probes with supra optical properties in water are still needed urgently. Focused on this situation, we herein reported a hemicyanine based probe for pH detection in aqueous solution. The probe has excellent water-solubility, high selectivity and sensitivity. Also, the structure of the probe from phenol to phenoxide induced a turn-on fluorescent response within a certain pH range of 4.5–10.7 and peaked with 30-fold enhancement, and the pKa value was determined to be 8.5. Simultaneously with the pH increase, a prominent solution color of the system changed from yellow to amaranth. More importantly, the biological experiments demonstrated the applicable of the probe to monitor the pH changes in living cells. This work illustrates that the probe could be practical and ideal pH indicator with good biological significance.Connected vanilline with benzoindoles moiety, we developed a novel pH probe which featured turn-on fluorescent responses and distinct color changes from yellow to amaranth within the pH range of 4.5–9.7 in aqueous solution. The probe has excellent water-solubility and high selectivity and sensitivity. Also, the probe could be used to monitor pH changes in living cells.
Co-reporter:Tao Liu, Fangjun Huo, Caixia Yin, Jianfang Li, Jianbin Chao, Yongbin Zhang
Dyes and Pigments 2016 Volume 128() pp:209-214
Publication Date(Web):May 2016
DOI:10.1016/j.dyepig.2015.12.031
•A green turn on fluorescent probe for biothiols in solution was developed.•The detection limit is as low as 10−8 M.•The probe can be applied in bioimaging.With the biological importance of biothiols, the development of probes for thiols has been an active research area in recent years. Here, we report a novel thiol-reactive fluorescent probe based on Michael addition reaction for selectively detecting thiols over other relevant biological species. The thiol adduct was characterized using NMR and mass spectroscopy and detection mechanism was further confirmed. This sensor with excellent selectivity for biothiols over other amino acids features a rapid signal response time, a good linearity range and a low detection limit. For the practical application of the sensor, it can be used to monitor thiol in live cells with turn-on fluorescence imaging.Based on the Michael addition reaction of thiol with the CC bond under mild conditions, we herein report a new fluorescent probe which features a rapid signal response time, a good linearity range and a low detection limit. The potential application of this new fluorescent probe was demonstrated by fluorescent imaging of thiol in living cells.
Co-reporter:Weijie Zhang, Fangjun Huo, Tao Liu, Yin Wen, Caixia Yin
Dyes and Pigments 2016 Volume 133() pp:248-254
Publication Date(Web):October 2016
DOI:10.1016/j.dyepig.2016.06.009
•The interaction between probe 1 and thiophenol in solution was studied in detailed.•The probe can be applied in bioimaging.•The detection limit is as low as 13 nM.Thiophenols, a class of toxic and polluting compounds, are widely used in industrial production. Meanwhile, some aliphatic thiols play important roles in living organisms. Therefore, the development of probes for specific thiophenol detection is of great importance. Herein, a novel highly sensitive and selective ‘off-on’ fluorescent probe for detecting thiophenols has been developed by an ICT mechanism through a rational design. The probe displays a large Stokes shift (140 nm) and 60-fold fluorescence intensity enhancement. More importantly, the probe features a rapid signal response time (within 100 s), a good linearity range and the detection limit is as low as 13 nM. In addition, the ability of the probe to detect thiophenols in living cells (HepG2 cells) via an enhancement of the fluorescence has also been demonstrated.A novel highly sensitive and selective ‘off-on’ fluorescent probe for detecting thiophenols has been developed by an ICT mechanism through a rational design. It displays a large Stokes shift (140 nm), a good linearity range, a rapid signal response time (within 100 s) and the detection limit is as low as 13 nM. In addition, the ability of the probe to detect thiophenols in living cells (HepG2 cells) via an enhancement of the fluorescence has also been proved.
Co-reporter:Jianfang Li, Caixia Yin, Fangjun Huo
Dyes and Pigments 2016 Volume 131() pp:100-133
Publication Date(Web):August 2016
DOI:10.1016/j.dyepig.2016.03.043
•All kinds of fluorophores in Zn2+ fluorescent probes were classified.•Sensing applications results from their complexing and basic properties were discussed.•This review brings forward the current status in the design and development of Zn2+ fluorescent probes.With the biological importance of zinc, the development of probes for zinc has been an active research area in recent years. With the aim of designing, synthesising and applying fluorescent sensors for Zn2+, this review provides an insight into Zn2+ sensors based on different fluorophores over past decades and their applications in the detection of zinc. Several types of fluorophores have been reported, including quinoline, rhodamine, coumarin, fluorescein, 4-amino-1,8-naphthalimide, Dipyrrometheneboron Difluoride, pyrene, porphyrin and others. It is of greatest importance that selects the suitable fluorophores for the design and synthesis of outstanding selective colorimetric or fluorimetric probes for detection of Zn2+ in living cell. Based on the versatile means of modification in these fluorophores, we can envision that there still present ample opportunities for designing efficient and novel fluorescent probes for the detection of Zn2+ in biological and environmental.The detection of zinc has long held the attention of the research area because of the biological importance. This review highlights the advances in the development of fluorescent and/or colorimetric probes, and the probes are classified according to fluorophores into seven categories including (1) quinoline, (2) rhodamine, (3) coumarin, (4) fluorescein, (5) 4-amino-1,8-naphthalimide, (6) BODIPY, (7) pyrene, (8) porphyrin. We hope that this review will help to design highly selective simple fluorescent and/or colorimetric probes for Zn2+ detection of in living cell.
Co-reporter:Weijie Zhang, Caixia Yin, Yongbin Zhang, Jianbin Chao, Fangjun Huo
Sensors and Actuators B: Chemical 2016 Volume 233() pp:307-313
Publication Date(Web):5 October 2016
DOI:10.1016/j.snb.2016.04.089
•Based on thiol nucleophilic substitution fluorescent probe was synthesized.•The compound exhibits highly selective recognition of thiol over other amino acids.•Its potential application in bioimaging was also illustrated.Herein we report a highly selective thiol-reactive fluorescent probe based on a nucleophilic substitution reaction for detecting thiols over other relevant biological species. The probe, triphenylamine as a fluorophore and 2,4-dinitrobenzenesulfonyl chloride as a nucleophilic substitution group was synthesized and characterized. The ability to specially recognizing thiol was investigated by UV–vis and fluorescence spectrometers. Among the tested amino acids, only Cys, Hcy and GSH could turn on the fluorescence emission. It suggested that the system was a highly selective sensor for thiols. More importantly, the compound features a good linearity range and the detection limit is as low as 10−8 mol/L. In addition, as a typical biological thiol, the ability of probe to detecting Cys in living cells (HepG2 cells) via an enhancement of the fluorescence was proved.
Co-reporter:Jiawei Li, Caixia Yin, Fangjun Huo, Kangming Xiong, Jianbin Chao, Yongbin Zhang
Sensors and Actuators B: Chemical 2016 Volume 231() pp:547-551
Publication Date(Web):August 2016
DOI:10.1016/j.snb.2016.03.067
•Two “turn-on” fluorescent probes, which are conveniently prepared were presented.•Two probes showed high selective and sensitive recognition for ClO−.•The mechanism was proved by 1H NMR and ESI-MS.In this work, 2-naphthol (1) and its derivative 1-(2-hydroxynaphthalen-1-yl)naphthalen-2-ol (BINOL) (2) as two ratiometric fluorescence probes are used to detect hypochlorite, which is one of the biologically important reactive oxygen species (ROS), by UV–vis and fluorescent spectrometers. The fluorescence intensity of probe 1 and 2 were gradually decreased when addition of ClO−. Also, the detailed signal mechanism was elucidated by 1H NMR and ESI-MS. In addition, the detection limits of probe 1 and 2 for ClO− were found to be 81 nM and 49 nM. Both two probes showed high selectivity for hypochlorite.In this study, we have developed two ratiometric fluorescence probes based on 2-naphthol and its derivative BINOL for the detection of ClO− over other analytes. We speculate the mechanism is based on a specific reaction promoted by hypochlorite: probe 1 and probe 2 can undertake intermolecular dehydration reaction in the presence of hypochlorite. In order to elucidate the detailed signal mechanism, 1H NMR and ESI-MS were carried out. In addition, the detection limits of probe 1 and 2 for ClO− were found to be 81 nM and 49 nM. Both two probes showed high selectivity for hypochlorite.
Co-reporter:Tao Liu, Fangjun Huo, Jianfang Li, Jianbin Chao, Yongbin Zhang, Caixia Yin
Sensors and Actuators B: Chemical 2016 Volume 232() pp:619-624
Publication Date(Web):September 2016
DOI:10.1016/j.snb.2016.04.014
•1,8-naphthalimide-based probe bearing maleimide group was synthesized.•The compound exhibits highly selective recognition of thiol over other amino acids with fast response.•Its potential application to bioimaging was also illustrated.Up to date, the design of highly selective and fast response probes for Cys, Hcy, and GSH is still a challenge and very few examples have been reported so far. In this study, we synthesized a 1,8-naphthalimide-based probe bearing maleimide group to selectively detect thiol. After introduce thiol, the fluorescence intensity of probe showed significant enhancement, but other amino acids did not generate any change. The kinetic study showed that the reaction was complete within 120 s for Cys, Hcy and GSH, indicating that probe reacts rapidly with thiol under the experimental conditions. Furthermore, the ability of probe to detect thiol in living cells via an enhancement of the fluorescence was proved.1,8-naphthalimide-based probe bearing maleimide group was synthesized to selectively detect thiol with fast response. The detection limit was found to be as low as 0.045 μmol/L. Its potential application to bioimaging was also illustrated.
Co-reporter:Kangming Xiong, Fangjun Huo, Caixia Yin, Yueying Chu, Yutao Yang, Jianbin Chao, Anmin Zheng
Sensors and Actuators B: Chemical 2016 Volume 224() pp:307-314
Publication Date(Web):1 March 2016
DOI:10.1016/j.snb.2015.10.047
•We have developed two new colorimetric and fluorescent probes for hypochlorite based on a novel recognition mechanism: amido oxidized nitroso-group by hypochlorites.•The optical properties of the probe 2 and its ClO−-addition product were studied based on DFT and TDDFT were explored at the m062x/6-31+G (d) level.•The probe 2 could be applied in practical applications such as detecting the hypochlorite concentration of sodium hypochlorite disinfectant and bioimagings.We have developed two new colorimetric and fluorescent probes for hypochlorite based on a novel recognition mechanism: amido oxidized nitroso-group by hypochlorites, which realized the preparation of nitroso compounds. Furthermore, 1H NMR, ESI-MS and theoretical calculation proved the recognition mechanism. In addition, the probe 2 was applied in practical applications such as detecting the hypochlorite concentration of sodium hypochlorite disinfectant and bioimagings.In this study, we have developed two new colorimetric and fluorescent probes for hypochlorite based on a novel recognition mechanism: amido oxidized nitroso-group by hypochlorites, which realized the preparation of nitroso compounds. Furthermore, 1H NMR, ESI-MS and TD-DFT calculations proved the novel recognition mechanism. In addition, the probe 2 was applied in practical applications such as detecting the hypochlorite concentration of sodium hypochlorite disinfectant and bioimagings.
Co-reporter:Yongkang Yue, Caixia Yin, Fangjun Huo, Jianbin Chao, Yongbin Zhang
Sensors and Actuators B: Chemical 2016 Volume 223() pp:496-500
Publication Date(Web):February 2016
DOI:10.1016/j.snb.2015.09.127
•We designed and synthesized a new chromene derivative.•The probe can specially recognize Cys.•The ability of probe to detect Cys in living cells was proved.A turn-on fluorescent probe for specific detection of cysteine (Cys) was developed based on the thiol-chromene click chemistry. Because of the relatively strong nucleophilic reactivity of SH of Cys compared with Hcy and GSH, this chromene derivate displayed excellent selectivity for Cys. The chromene derivate (probe 1) displayed non-fluorescent emission in DMSO/HEPES (v/v, 1:1, pH 7.4) system. However, the nucleophilic attack of Cys to the α,β-unsaturated ketone in probe 1 induced a 10 fold fluorescent emission enhancement at 515 nm. With the excellent properties including rapid, high selectivity and sensitivity toward Cys in aqueous solution, probe 1 was promoted to detect Cys quantitatively. The detection limit of this probe for Cys was found to be 64 nmol/L. The further bioimaging experiment of intracellular Cys detection by this probe was successfully applied in living cells, indicating that this probe holds great potential for biological applications.Based on the thiol ‘click’ chromene ring-open reaction, we designed and synthesized a chromene derivative as turn-on fluorescent probe for the Cys detection. With high sensitivity and selectivity, the probe could be used for intracellular Cys detection and bioimaging.
Co-reporter:Kangming Xiong, Caixia Yin, Jianbin Chao, Yongbin Zhang, Fangjun Huo
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2016 Volume 166() pp:79-83
Publication Date(Web):5 September 2016
DOI:10.1016/j.saa.2016.05.016
•Two new fluorescent probes for hypochlorite were developed.•The detection could be realized in quasi-aqueous phase with low detection.•The probe could be used to monitor intracellular ClO− in HepG2 cells.In this work, two high selective and sensitive fluorescent probes for ClO−, 7-Hydroxycoumarin and 4-Hydroxycoumarin were designed. The reaction mechanism that we speculated was the oxidized ring opening reaction and hydrolysis. The detection could be realized in quasi-aqueous phase and the detection limits of probe [7] and probe [4] for ClO− were found to be 56.8 nM and 70.5 nM. Furthermore, the probes can be used to cell imagings.
Co-reporter:Yutao Yang, FangJun Huo, Caixia Yin, Jianbin Chao, Yongbin Zhang
Dyes and Pigments 2015 Volume 114() pp:105-109
Publication Date(Web):March 2015
DOI:10.1016/j.dyepig.2014.11.004
•The compound, N-[4-Methylcoumarin-7-yl]maleimide was firstly synthesized.•The compound exhibits highly selective recognition of cysteine over Hcy and GSH.•Its potential application to bioimaging was also illustrated.Up to date, the design of highly selective probes for Cys, Hcy, and GSH is still a challenge and very few examples have been reported so far. In this work, the compound, N-[4-Methylcoumarin-7-yl] maleimide was synthesized and it can specially recognize on Cys as an ‘OFF–ON’ fluorescent probe. For specific recognition on Cys of probe depends on its maleimide group, the structural and acidic differences of biothiol itself. Furthermore, the ability of probe to detect Cys in living cells (HepG2 cells) via an enhancement of the fluorescence was proved.N-[4-Methylcoumarin-7-yl]maleimide was firstly to be developed as a probe which exhibits highly selective recognition of cysteine. The detection limit was found to be as low as 74 nmol/L. Its potential application to bioimaging was also illustrated.
Co-reporter:Jianfang Li, Caixia Yin and Fangjun Huo
RSC Advances 2015 vol. 5(Issue 3) pp:2191-2206
Publication Date(Web):19 Nov 2014
DOI:10.1039/C4RA11870G
The development of probes for the biologically important gas hydrogen sulfide (H2S) has been an active area of research in recent years. This review summarizes recent work on the recognition mechanisms used by chromogenic and fluorogenic sensors and their applications in the detection of H2S. Several types of recognition mechanisms have been reported, including cleavage of the alcoxyl (R–O) bond, cleavage of the S–O bond, reduction of the azide group, the reduction of nitro groups to amines, the replacement of a copper complex and double bond addition reactions. In all instances the reactions are accompanied by changes in color and/or emission. These recognition mechanisms are important and straightforward procedures for use in the design of highly selective colorimetric or fluorimetric probes for the detection of H2S in living cells.
Co-reporter:Jianfang Li, Caixia Yin, Fangjun Huo, Jianbin Chao, Yongbin Zhang and Lixi Niu
Analytical Methods 2015 vol. 7(Issue 20) pp:8545-8549
Publication Date(Web):20 Aug 2015
DOI:10.1039/C5AY01834J
A fluorescent probe has been synthesized and characterized as a selective and sensitive sensor for thiol detection. The probe exhibits a rapid response and high sensitivity to thiols in HEPES:DMF = 1:1 (v/v pH = 7.0) solution. The practical utility of the probe was demonstrated by its application to the detection of thiols in living cells.
Co-reporter:Fangjun Huo, Jin Kang, Caixia Yin, Jianbin Chao, Yongbin Zhang
Sensors and Actuators B: Chemical 2015 215() pp: 93-98
Publication Date(Web):
DOI:10.1016/j.snb.2015.03.047
Co-reporter:Cai-Xia Yin, Li-Jun Qu, Fang-Jun Huo
Chinese Chemical Letters 2014 Volume 25(Issue 9) pp:1230-1234
Publication Date(Web):September 2014
DOI:10.1016/j.cclet.2014.06.017
A pyridoxal-based chemosensor was synthesized by reacting hydrazine hydrate and pyridoxal hydrochloride in ethanol and characterized by NMR and ESI-MS. The optical properties of the compound were investigated in a methanol: HEPES solution. The compound displayed selectivity for Cu2+, as evidenced by a colorless to yellow color change, which was characterized using UV–vis spectroscopy. The fluorescence of the compound can be quenched only by Cu2+, accompanying by a color change from blue to colorless. Furthermore, it can be used in bioimaging.A pyridoxal-based compound was used as a colorimetric and fluorescent probe for Cu2+, and it can be used in bioimaging.
Co-reporter:Wei Gao, Yutao Yang, Fangjun Huo, Caixia Yin, Ming Xu, Yongbin Zhang, Jianbin Chao, Shuo Jin, Shuping Zhang
Sensors and Actuators B: Chemical 2014 193() pp: 294-300
Publication Date(Web):
DOI:10.1016/j.snb.2013.11.078
Co-reporter:Caixia Yin, Fangjun Huo, Jingjing Zhang, Ramón Martínez-Máñez, Yutao Yang, Haigang Lv and Sidian Li
Chemical Society Reviews 2013 vol. 42(Issue 14) pp:6032-6059
Publication Date(Web):23 May 2013
DOI:10.1039/C3CS60055F
Because of the biological importance of thiols, the development of probes for thiols has been an active research area in recent years. In this review, we summarize the results of recent exciting reports regarding thiol-addition reactions and their applications in thiol recognition. The examples reported can be classified into four reaction types including 1,1, 1,2, 1,3, 1,4 addition reactions, according to their addition mechanisms, based on different Michael acceptors. In all cases, the reactions are coupled to color and/or emission changes, although some examples dealing with electrochemical recognition have also been included. The use of thiol-addition reactions is a very simple and straightforward procedure for the preparation of thiol-sensing probes.
Co-reporter:Caixia Yin, Jingjing Zhang, Fangjun Huo
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2013 Volume 115() pp:772-777
Publication Date(Web):November 2013
DOI:10.1016/j.saa.2013.06.095
•The interaction between 1,4-dihydroxyanthraquinone and metal ions in solution was studied in detailed.•1,4-Dihydroxyanthraquinone has better response for Hg2+ and Er3+ over other metal ions.•1,4-Dihydroxyanthraquinone has a potential application in the design of metal ions probe.The interaction between 1,4-dihydroxyanthraquinone (1,4-DHA) and metal ions was studied by UV–Visible and fluorescence spectroscopies in solution. Time-dependent density functional theory calculations confirmed complex structures. The investigation results showed 1,4-DHA can selectively respond some metal ions and can be monitored by UV–Vis, fluorescence spectra and naked-eye. So 1,4-DHA has a potential application in the design of metal ions probe. More, as typical metal ions, Hg2+ and Er3+, their reaction abilities for 1,4-DHA were studied in detailed. Experimental results showed they have better response for 1,4-DHA. And theoretical calculation concluded that Er3+ easily reacts with 1,4-DHA over Hg2+ attributed to the low reaction energy of Er3+-1,4-DHA than Hg2+-1,4-DHA.The statement: Hg2+ and Er3+, their reaction abilities for 1,4-DHA were studied by UV–Visible and fluorescence spectroscopies in solution. They all have better response for 1,4-DHA in the spectra with distinct and regular changes. And theoretical calculation concluded that Er3+ easily react with 1,4-DHA over Hg2+ attributed to the low reaction energy of Er3+-1,4-DHA than Hg2+-1,4-DHA.
Co-reporter:Fangjun Huo, Long Wang, Caixia Yin, Yutao Yang, Hongbo Tong, Jianbin Chao, Yongbin Zhang
Sensors and Actuators B: Chemical 2013 Volume 188() pp:735-740
Publication Date(Web):November 2013
DOI:10.1016/j.snb.2013.07.102
•Three isomers of rhodamine derivative were synthesized and fully characterized.•Compound 1 can recognize Cu2+.•The probe is a fluorescence probe thus can be applied in bioimaging.Three isomers of rhodamine derivative, ortho-pyridylaldehyde rhodamine hydrazone (1), meta-pyridylaldehyde rhodamine hydrazone (2), and para-pyridylaldehyde rhodamine hydrazone (3) were synthesized and characterized. And their recognition abilities for Cu2+ were studied by UV–Vis spectra. The result showed that ortho-pyridylaldehyde rhodamine hydrazone (1) due to having a suitable space coordination structure is a best selective probe for Cu2+ over other metal ions in 10 mmol/L HEPES buffer, pH 7.0/CH3OH (v/v, 1:1), and that it is a quick colorimetric and lagged fluorometric dual-model probe for Cu2+. Because it is a fluorescence turn-on probe, cell experiments show probe can permeate through cell membranes and react to Cu2+ within living cells.Three isomers of rhodamine derivative, ortho-pyridylaldehyde rhodamine hydrazone (1), meta-pyridylaldehyde rhodamine hydrazone (2), and para-pyridylaldehyde rhodamine hydrazone (3) were synthesized and characterized. And their recognition abilities for Cu2+ were studied. The result showed that ortho-pyridylaldehyde rhodamine hydrazone (1) is best probe for Cu2+, furthermore 1 is a colorimetric and fluorometric dual-model probe for Cu2+. It was also applied in bioimaging.
Co-reporter:Yutao Yang, Caixia Yin, Fangjun Huo, Yueyin Chu, Hongbo Tong, Jianbin Chao, Fangqin Cheng, Anmin Zheng
Sensors and Actuators B: Chemical 2013 Volume 186() pp:212-218
Publication Date(Web):September 2013
DOI:10.1016/j.snb.2013.06.013
The salicylaldehyde derivative, 9-formyl-8-hydroxyjulolidine was developed as a fluorescent probe to detect weak acid ions. With the salicylaldehyde moiety as the chromophore, the probe exhibits pH sensitive detection of hydrogen sulfide and silicate in aqueous solution. It displays an excellent selectivity for hydrogen sulfide and silicate over other weak acid salts. Time-dependent density functional theory calculations confirmed that the fluorescence turn-on mechanism involved blocking intramolecular charge transfer. The probe detects S2− in live cells, providing a powerful method to study H2S chemistry in biological systems.9-Formyl-8-hydroxyjulolidine, with the salicylaldehyde moiety as the chromophore, was developed as a fluorescent probe to detect hydrogen sulfide and silicate in aqueous solution. Time-dependent density functional theory calculations confirmed that the fluorescence turn-on mechanism involved blocking intramolecular charge transfer. The probe detects S2− in live cells, providing a powerful method to study H2S chemistry in biological systems.
Co-reporter:Lijun Qu, Caixia Yin, Fangjun Huo, Yongbin Zhang, Yingqi Li
Sensors and Actuators B: Chemical 2013 Volume 183() pp:636-640
Publication Date(Web):5 July 2013
DOI:10.1016/j.snb.2013.04.017
The commercially available fluorescent probe, 1,8-diamino naphthalene with a naphthalene ring as a chromophore and two amino groups as binding sites has been developed for sensitive detection of copper ions by fluorescence spectrometer in aqueous solution. It displayed an excellent selectivity and sensitivity for Cu2+ over other metal ions. The mechanism is that the fluorescence of probe was quenched by the paramagnetic effect from spin–orbit coupling of the Cu2+ after probe coordinated with Cu2+, and mechanism was proved by ESI-MS. The probe can be used to react to Cu2+ in live cells, providing a potentially powerful approach for probing Cu2+ chemistry in biological system.The commercially available fluorescent probe with a naphthalene ring as a chromophore and two amino groups as binding sites has been developed for sensitive detection of copper ions in aqueous solution. It displayed an excellent selectivity and sensitivity for Cu2+ over other metal ions, and mechanism was proved by ESI-MS. The probe can be used to react to Cu2+ in live cells, providing a potentially powerful approach for probing Cu2+ chemistry in biological system.
Co-reporter:Caixia YIN;Fangjun HUO;Yanbo WU;Yanlin LIU;Pin YANG
Chinese Journal of Chemistry 2009 Volume 27( Issue 1) pp:63-68
Publication Date(Web):
DOI:10.1002/cjoc.200990027
Abstract
Two kinds of Ln complexes of [Ln(TTA)4]·HP (Ln=Yb or Er, TTA=2-[(Trifluoroaceto)aceto]thinophene, HP=piperidine) have been synthesized and characterized, and their DNA-binding properties investigated using UV spectra, fluorescent spectra, viscometry and molecular modeling. The results show that they can intercalate into the double helices of DNA. More important thing is that their fluorescence intensity can be enhanced by DNA, thererfore, a sensitive fluorescence method for the determination of DNA may be developed. The cleavage reaction on plasmid DNA has been monitored by agarose gel electrophoresis. Interestingly, the complexes can cleave circular plasmid pBR322 DNA at pH=7.2 and 37 °C. In addition, BDNPP [bis(2,4-dinitrophenyl)-phosphate] was chosen as a model compound to further study their cleavage mechanism of pBR322 DNA. From the first-order kinetics equation, it was proved indirectly that the mechanism may be a hydrolytic cleavage.
Co-reporter:Caixia YIN;Fangjun HUO;Wenzhen WANG;Rayyat-H ISMAYILOY;Genehsiang LEE;Chenyu YEH;Shieming PENG;Pin YANG
Chinese Journal of Chemistry 2009 Volume 27( Issue 7) pp:1295-1299
Publication Date(Web):
DOI:10.1002/cjoc.200990216
Abstract
The synthesis, crystal structure, electrochemical and magnetic properties of a type of pyridine-modulated linear pentanuclear complex, [Ni5(µ-dmpzda)4(NCS)2] [dmpzda-H2=N,N′-di(4-methyl pyridin-2-yl)pyrazine-2,6-diamine], were studied. The complex involves a Ni5 linear chain unit with all of the Ni-Ni-Ni being nearly 180°, terminated by the two axial ligands. This pentanuclear linear metal chain is helically wrapped by four syn-syn-syn-syn type dmpzda ligands. There are two types of Ni–Ni distances existing in the complex. The terminal Ni–Ni distances bonded with the axial ligand are longer (2.3821 Å) affected by the axial ligands. The inner Ni–Ni distances are very short and remain constant (2.2959 Å). Two terminal Ni(II) ions bonded with the axial ligands are in a square-pyramidal (NiN4NCS) environment and exhibit long Ni–N bonds (2.103 Å), which are consistent with a high-spin Ni(II) configuration. The inner three Ni(II) ions display short Ni–N (1.886–1.906 Å) bond distances, which are consistent with a squareplanar (NiN4), diamagnetic arrangement of a low-spin Ni(II) configuration. This compound exhibits similar [Ni5(µ-tpda)4(NCS)2] magnetic behavior, indicating an antiferromagnetic interaction of two terminal high-spin Ni(II) ions in these complexes.
Co-reporter:Caixia Yin, Xiaoqi Li, Yongkang Yue, Jianbin Chao, Yongbin Zhang, Fangjun Huo
Sensors and Actuators B: Chemical (July 2017) Volume 246() pp:615-622
Publication Date(Web):July 2017
DOI:10.1016/j.snb.2017.02.127
Co-reporter:Caixia Yin, Fangjun Huo, Jingjing Zhang, Ramón Martínez-Máñez, Yutao Yang, Haigang Lv and Sidian Li
Chemical Society Reviews 2013 - vol. 42(Issue 14) pp:NaN6059-6059
Publication Date(Web):2013/05/23
DOI:10.1039/C3CS60055F
Because of the biological importance of thiols, the development of probes for thiols has been an active research area in recent years. In this review, we summarize the results of recent exciting reports regarding thiol-addition reactions and their applications in thiol recognition. The examples reported can be classified into four reaction types including 1,1, 1,2, 1,3, 1,4 addition reactions, according to their addition mechanisms, based on different Michael acceptors. In all cases, the reactions are coupled to color and/or emission changes, although some examples dealing with electrochemical recognition have also been included. The use of thiol-addition reactions is a very simple and straightforward procedure for the preparation of thiol-sensing probes.
Co-reporter:Fangjun Huo, Yaqiong Zhang, Peng Ning, Xiangming Meng and Caixia Yin
Journal of Materials Chemistry A 2017 - vol. 5(Issue 15) pp:NaN2803-2803
Publication Date(Web):2017/03/16
DOI:10.1039/C7TB00299H
The sulfide anion is significant in industrial processes, biology and environmental science. Hence, robust fluorescent sensors for sulfide which are water soluble and biocompatible are highly desirable. Here, we developed a novel red-emitting fluorescent probe (SP1) for the sulfide anion based on cleaving the dinitrobenzenesulfonate ester to restore the fluorescence, accompanied by a long wavelength emission at 644 nm. The detection process took place in 100% PBS buffer, which suggested it had excellent water solubility. Most importantly, the ability of SP1 to detect sulfide anions in living cells (MCF-7 cells) and zebrafish has also been proven.
Co-reporter:
Analytical Methods (2009-Present) 2015 - vol. 7(Issue 20) pp:NaN8549-8549
Publication Date(Web):2015/08/20
DOI:10.1039/C5AY01834J
A fluorescent probe has been synthesized and characterized as a selective and sensitive sensor for thiol detection. The probe exhibits a rapid response and high sensitivity to thiols in HEPES:DMF = 1:1 (v/v pH = 7.0) solution. The practical utility of the probe was demonstrated by its application to the detection of thiols in living cells.
