CN113149952A - Chromene sulfonyl hydrazone derivative fluorescent probe and preparation method and application thereof - Google Patents
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- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 60
- -1 Chromene sulfonyl hydrazone derivative Chemical class 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 34
- 238000000799 fluorescence microscopy Methods 0.000 claims abstract description 19
- 210000002472 endoplasmic reticulum Anatomy 0.000 claims abstract description 13
- 239000013078 crystal Substances 0.000 claims abstract description 8
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims abstract description 8
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 5
- RISKINCQRSLFRK-UHFFFAOYSA-N 2h-chromene-3-carbaldehyde Chemical compound C1=CC=C2OCC(C=O)=CC2=C1 RISKINCQRSLFRK-UHFFFAOYSA-N 0.000 claims description 4
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 238000001035 drying Methods 0.000 abstract description 4
- 238000001914 filtration Methods 0.000 abstract description 4
- 238000005406 washing Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- 230000004962 physiological condition Effects 0.000 abstract 1
- 239000000523 sample Substances 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 238000010586 diagram Methods 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 9
- 238000001514 detection method Methods 0.000 description 8
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 5
- SQLUEMCLILPGSJ-UHFFFAOYSA-N 2h-benzo[h]chromene-3-carbaldehyde Chemical compound C1=CC=CC2=C(OCC(C=O)=C3)C3=CC=C21 SQLUEMCLILPGSJ-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 238000002073 fluorescence micrograph Methods 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 230000006907 apoptotic process Effects 0.000 description 2
- 229910001914 chlorine tetroxide Inorganic materials 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 2
- 230000035790 physiological processes and functions Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000008685 targeting Effects 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000004770 chalcogenides Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 231100000196 chemotoxic Toxicity 0.000 description 1
- 230000002604 chemotoxic effect Effects 0.000 description 1
- 150000008371 chromenes Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000003712 lysosome Anatomy 0.000 description 1
- 230000001868 lysosomic effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000003463 organelle Anatomy 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
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- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
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Abstract
本发明提供了一种色烯磺酰腙衍生物荧光探针及其制备方法和应用，其中所述色烯磺酰腙衍生物的化学结构式如下：
The invention provides a chromenesulfonylhydrazone derivative fluorescent probe and a preparation method and application thereof, wherein the chemical structural formula of the chromenesulfonylhydrazone derivative is as follows:
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a chromene sulfonyl hydrazone derivative fluorescent probe as well as a preparation method and application thereof.
Background
Hypochlorous acid (HClO)/hypochlorite (ClO)-) Is widely used as a disinfectant in daily life. At the same time, ClO-Is also an important bioactive oxygen (ROS) that participates in numerous physiological processes. However, concentrations in excess of the normal range can cause a variety of diseases including cancer. The endoplasmic reticulum is an important class of organelles whose normal physiological functions are impaired when cells are stimulated by chemotoxic substances, so-called endoplasmic reticulum stress. Too much or too long endoplasmic reticulum stress can cause apoptosis. The endoplasmic reticulum is one of the major sites for the intracellular production of ROS. Thus, ClO in endoplasmic reticulum-The detection and analysis of (A) have very important research values and are helpful for understanding the endoplasmic reticulum-induced apoptosis process.
The fluorescent probe technology has the advantages of high sensitivity, simple operation, real-time online detection and the like, and is considered to detect the ClO-The ideal means of the method. In recent years, ClO has been targeted-The fluorescent probe of (1) has been developed, and the design strategy thereof is generally to use methoxyphenol, chalcogenides, hydrazides, hydroxylamines, C = C, etc. as a recognition group and use ClO-The strong oxidizing property of the probe oxidizes the recognition group to cause the fluorescence change of the probe, thereby realizing the purpose of detection. However, most probes rely solely on the change of fluorescence intensity at a single emission wavelength to realize detection, and are easily influenced by environmental factors such as instrument efficiency and probe concentration. To ratiometric fluorescent probesThe ratio of the intensities of the two different emission peaks is used as a signal reference, so that the interference can be effectively eliminated. Furthermore, ratiometric ClO targeting endoplasmic reticulum-Fluorescent probes are not widely reported.
In view of the above, the present invention is particularly proposed.
Disclosure of Invention
In view of the problems in the prior art, consider 2H-benzo [ 2 ]h]Chromene-3-carbaldehyde has excellent optical properties, and sulfonylhydrazone can be used as ClO-The invention synthesizes a high-sensitivity and high-selectivity ratio type ClO based on chromene sulfonyl hydrazone derivatives-A fluorescent probe. The probe has an endoplasmic reticulum targeting function and can be used for ClO in the endoplasmic reticulum of cells-And (4) detecting the concentration.
The invention mainly aims to provide a novel polypeptide for ClO in endoplasmic reticulum-The ratio type chromene sulfonyl hydrazone derivative fluorescent probe has high sensitivity and good selectivity; another purpose is to provide a preparation method and application of the fluorescent probe.
In order to achieve the purpose, the invention adopts the following technical scheme: a chromene sulfonyl hydrazone derivative fluorescent probe is disclosed, wherein the chromene sulfonyl hydrazone derivative has the following structural formula:
the invention also provides a preparation method of the chromene sulfonyl hydrazone derivative fluorescent probe, which comprises the following steps:
s1: dissolving 2H-benzo [ H ] chromene-3-formaldehyde and p-toluenesulfonyl hydrazide in ethanol;
s2: stirring for 12h under reflux;
s3: and cooling to room temperature, filtering, washing with ethanol, and drying to obtain yellow flaky crystals, namely the chromene sulfonyl hydrazone derivative fluorescent probe.
Further, the ethanol of steps S1 and S3 is 95% ethanol or absolute ethanol.
Further, the molar ratio of the 2H-benzo [ H ] chromene-3-carbaldehyde to p-toluenesulfonyl hydrazide added in step S1 was 1: 1.
Further, specifically, a mixture of 2H-benzo [ H ] chromene-3-carbaldehyde (210 mg, 1 mmol) and p-toluenesulfonyl hydrazide (190 mg, 1 mmol) was added to 10 mL of ethanol, and the mixture was stirred under reflux for 12 hours. And cooling to room temperature, filtering, washing with ethanol, and drying to obtain yellow flaky crystals, namely the chromene sulfonyl hydrazone derivative fluorescent probe.
The invention also provides an application of the chromene sulfonyl hydrazone derivative fluorescent probe, namely the chromene sulfonyl hydrazone derivative fluorescent probe is used as ClO-Application of fluorescent probe, especially in detecting cell endoplasmic reticulum ClO-The fluorescent probe of (1).
Compared with the prior art, the invention has the advantages and positive effects that:
the chromene sulfonyl hydrazone derivative fluorescent probe is prepared through condensation reaction, raw materials are easy to obtain, and the synthesis and post-treatment methods are simple. Among the various common anions and active oxygen, para-ClO-The fluorescent recognition performance of the ratio is higher. The probe can target the endoplasmic reticulum of the cell and has wide potential application value.
Drawings
FIG. 1 shows a chromene sulfonyl hydrazone derivative fluorescent probe prepared in example 1 of the present invention1H NMR spectrum;
FIG. 2 shows the chromene sulfonyl hydrazone derivative fluorescent probe prepared in example 1 of the present invention13C NMR spectrum;
FIG. 3 is a mass spectrum of the chromene sulfonyl hydrazone derivative fluorescent probe prepared in example 1 of the present invention;
FIG. 4 is a crystal structure diagram of the chromene sulfonyl hydrazone derivative fluorescent probe prepared in example 1 of the present invention;
FIG. 5 shows a chromene sulfonylhydrazone derivative fluorescent probe (1X 10) prepared in example 1 of the present invention-5mol/L) in DMSO/PBS (2/8, v/v, 10 mM, pH =7.0) was added 5X 10 each-4mol/L anion (HSO)3 -、SO4 2-、PPi、HSO4 -、PO4 3-、H2PO4 -、CN-、ClO4 -、HPO4 2-、I-、Br-、F-、S2-、Cl-、OAC-、SO3 2-) And active oxygen (ClO)-、H2O2、1O2OH, NO and O2 −) The fluorescence spectrum of (excitation wavelength is 400 nm), and the inset shows the probe under 365 nm UV lamp and the probe + ClO-A color change of the solution of (a);
FIG. 6a is a drawing showing a chromene sulfonylhydrazone derivative fluorescent probe (1X 10) prepared in example 1 of the present invention-5mol/L) in DMSO/PBS (2/8, v/v, 10 mM, pH =7.0) solution titrated with different concentrations of ClO−Fluorescence spectrum (excitation wavelength 400 nm). FIG. 6b shows the ratio of fluorescence intensity at 525 nm and 475 nm with ClO-Linear trend plot of concentration.
FIG. 7 is a photograph of a co-stained fluorescent image of a chromenesulfonylhydrazone derivative fluorescent probe with a commercial endoplasmic reticulum-positioning dye ER Tracker Red in HeLa cells; 1X 10 for HeLa cells-5After 30 minutes of co-incubation of the mol/L fluorescent probe with ER Tracker Red, fluorescence imaging was performed using an Olympus FV500-IX70 confocal laser microscope.
Wherein: a is a blue channel fluorescence imaging picture; b is a red channel fluorescence imaging graph; c is a picture obtained after the blue channel and the red channel are superposed; d is a bright field diagram; e is a picture obtained by superposing a blue channel, a red channel and a bright field; and f is an overlay of the intensity distributions of the blue and red channels.
FIG. 8 shows the chromene sulfonyl hydrazone derivative fluorescent probe and ClO in HeLa cells−A fluorescence imaging map of; 1X 10 for HeLa cells-5Incubation with mol/L fluorescent probe for 30 min and addition of 5X 10-4 mol/L ClO−After incubation for a further 30 minutes, fluorescence imaging was carried out using an Olympus FV500-IX70 confocal laser microscope.
Wherein: a is a fluorescence imaging diagram of the blue channel of the fluorescence probe; b is a fluorescence imaging diagram of the green channel of the fluorescence probe; c is the bright field diagram of the fluorescent probe; d is the superposition of the bright field image and the fluorescence image of the fluorescent probeA picture; e is the fluorescent probe + ClO−Blue channel fluorescence imaging; f is the fluorescent probe + ClO−Green channel fluorescence imaging; g is the fluorescent probe + ClO−Imaging under bright field; h is the fluorescent probe + ClO−And (5) superposing the bright field image and the fluorescence image.
Detailed Description
The present invention is described in further detail below with reference to the drawings and specific examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention. The reagents and raw materials adopted by the embodiment of the invention are purchased from conventional markets.
Example 1
The reaction route of the chromene sulfonyl hydrazone derivative fluorescent probe in the embodiment is as follows:
the preparation method of the chromene sulfonyl hydrazone derivative fluorescent probe comprises the following steps:
a mixture of 2H-benzo [ H ] chromene-3-carbaldehyde (210 mg, 1 mmol) and p-toluenesulfonylhydrazide (190 mg, 1 mmol) was added to 10 mL of ethanol, and the mixture was stirred at reflux for 12 hours. After cooling to room temperature, filtration, washing with ethanol and drying, yellow plate-like crystals were obtained with a yield of 86%. The nuclear magnetic resonance analysis of the prepared chromene sulfonyl hydrazone derivative is carried out by a nuclear magnetic resonance instrument, and the result is as follows:
1H NMR (400 MHz, d 6 -DMSO) δ (ppm): 11.5 (1H, s, NH), 8.13-8.15 (1H, s, CH=N), 7.76-7.86 (5H, m) / 7.68 (1H, s) / 7.53-7.56 (1H, s) /7.39-7.45 (3H, s) for Ar-H, 7.12-7.14 (1H, s, CH), 4.98 (2H, s, CH2), 2.39 (3H, s, CH3) The specific nmr hydrogen spectrum is shown in fig. 1;
13C NMR (400 MHz, d 6 -DMSO) δ (ppm): 153.09, 146.32, 144.00, 136.37, 131.32, 130.15, 129.50, 129.00, 127.69, 127.32, 125.43, 124.62, 122.16, 117.78, 115.14, 63.9421.50. specific NMR carbon spectra are shown in FIG. 2;
mass Spectrometry ESI-MS: M/z = 379.1079 for [ M + H ]]+. The specific mass spectrum is shown in FIG. 3.
Single crystal X-ray diffraction determines the crystal structure of the probe, see figure 4.
Example 2
Chromene sulfonyl hydrazone derivative p-ClO-Optical property measurement of
The chromene sulfonylhydrazone derivative prepared in example 1 above was used as a fluorescent probe and prepared in DMSO/PBS (2/8, v/v, 10 mM, pH =7.0) at a molar concentration of 1 × 10-5mol/L solutions, each in a molar concentration of 5X 10-4mol/L of an anion (HSO)3 -、SO4 2-、PPi、HSO4 -、PO4 3-、H2PO4 -、CN-、ClO4 -、HPO4 2-、I-、Br-、F-、S2-、Cl-、OAC-、SO3 2-) And active oxygen (ClO)-、H2O2、1O2OH, NO and O2 −) The same amount of the above-mentioned fluorescent probe solution was added to the solution of (1), and the analysis was carried out by a fluorescence spectrometer (excitation wavelength: 400 nm), and the obtained fluorescence spectrum was shown in FIG. 5. As can be seen from FIG. 5, only ClO is present-Can cause the emission peak of the probe to be enhanced and red-shifted, and other ions have no change, which indicates that the chromene sulfonyl hydrazone derivative prepared by the invention is only used as the probe for ClO-Has obvious response. Inset shows probes under 365 nm ultraviolet lamp and probes + ClO-The color of the solution changed, and it can be seen that ClO was added-The post probe solution changed from blue to green, indicating that the probe was useful for ClO-The rapid identification of (1).
ClO can be obtained by calculation from the titration spectrum of FIG. 6−Detection limit of 1.01 × 10-8mol/L, fluorescence intensity ratio F525/F475Linear detection range of 3.0 × 10-6-8.0×10-6mol/L. Thus the chromenes produced by the present inventionSulfonylhydrazone derivatives are useful in ClO-The fluorescent quantitative detection of (3).
Example 3
ClO in cell of chromene sulfonyl hydrazone derivative fluorescent probe-Detection experiment of
The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of protection is not limited thereto. The equivalents and modifications of the present invention which may occur to those skilled in the art are within the scope of the present invention as defined by the appended claims.
Claims (6)
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988000197A1 (en) * | 1986-06-26 | 1988-01-14 | Alkaloida Vegye^´Szeti Gya^´R | Benzopyran and benzothiopyran derivatives and compositions containing them |
| CN108383823A (en) * | 2018-03-23 | 2018-08-10 | 河南理工大学 | Aphthopyrans kappa hydazone derivative and its preparation method and application |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1988000197A1 (en) * | 1986-06-26 | 1988-01-14 | Alkaloida Vegye^´Szeti Gya^´R | Benzopyran and benzothiopyran derivatives and compositions containing them |
| CN108383823A (en) * | 2018-03-23 | 2018-08-10 | 河南理工大学 | Aphthopyrans kappa hydazone derivative and its preparation method and application |
Non-Patent Citations (2)
| Title |
|---|
| XIAO-CHUANG CHANG ET AL.: "A tosylhydrazone-based probe for the ratiometric fluorescent detection of hypochlorite in endoplasmic reticulum of living cells" * |
| XU TANG ET AL.: "Developed a novel quinazolinone based turn-on fluorescence probe for highly selective monitoring hypochlorite and its bioimaging applications" * |
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