CN109608474B - Compound for detecting tyrosinase and preparation method and application thereof - Google Patents
Compound for detecting tyrosinase and preparation method and application thereof Download PDFInfo
- Publication number
- CN109608474B CN109608474B CN201811523187.8A CN201811523187A CN109608474B CN 109608474 B CN109608474 B CN 109608474B CN 201811523187 A CN201811523187 A CN 201811523187A CN 109608474 B CN109608474 B CN 109608474B
- Authority
- CN
- China
- Prior art keywords
- compound
- tyrosinase
- tyr
- detecting
- fluorescent probe
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- 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
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
The invention belongs to the field of biochemical engineering, and particularly relates to a preparation method and application of a compound FL-O-T for detecting tyrosinase. The structural general formula of the compound FL-O-T is as follows:
wherein R is1、R2、R3Hydrogen, alkyl or other common substituents. The compound FL-O-T can be used as a fluorescent probe for detecting tyrosinase, and is synthesized by nucleophilic substitution reaction of fluorescein derivatives and m-hydroxybenzyl bromide. The compound FL-O-T is synthesized by a nucleophilic substitution reaction of a fluorescein derivative FT-OH and m-hydroxybenzyl bromide. The target compound has high chemoselectivity, can track and detect tyrosinase in vitro and in vivo, and successfully monitors the activity of the tyrosinase in cancer cells and zebra fish.
Description
Technical Field
The invention belongs to the field of biochemical engineering, relates to construction of a fluorescent probe for detecting intracellular tyrosinase (Tyr), and particularly relates to a fluorescent probe for detecting intracellular tyrosinase (Tyr) and a preparation method and biological application thereof.
Background
Tyrosinase (Tyr) is an important copper-containing oxidase enzyme, widely found in plants, animal tissues and fungi. Tyrosinase also plays an important role in the synthesis of melanin, which determines skin color and protects DNA in skin cells from ultraviolet radiation. In addition, tyrosinase, which is abnormally expressed in biological systems, is thought to be associated with many diseases, such as skin diseases and melanoma. In addition, tyrosinase may also induce neurodegeneration, which is responsible for parkinson's disease. Therefore, developing a sensitive and selective method to evaluate the biomarkers is of great value for understanding their role in various biological and pathological processes and provides important references for the diagnosis of tyrosinase related diseases.
To date, several analytical methods for detecting tyrosinase have been developed, such as colorimetric methods, electrochemical analysis, and nanoparticle-based methods. However, these methods have the disadvantages of low sensitivity and unsuitability for real-time imaging in living samples. Fluorescent probes are powerful tools due to their ultra-sensitivity, high selectivity and high spatial resolution. To date, several fluorescent probes for tyrosinase assays have been developed, and most of them suffer from interference of various Reactive Oxygen Species (ROS), such as HOCl, H2O2And ONOO-. Therefore, there is an urgent need to develop a novel fluorescent probe that can overcome the above disadvantages.
Disclosure of Invention
The first purpose of the invention is to provide a fluorescent probe for detecting Tyr.
The second purpose of the invention is to provide a preparation method of the fluorescent probe for detecting Tyr.
The third purpose of the invention is to provide the application of the fluorescent probe for detecting Tyr in cells.
The fourth purpose of the invention is to provide an application of the fluorescent probe for detecting Tyr in the detection of Tyr in zebra fish.
The technical scheme of the invention is as follows:
a fluorescent probe for detecting tyrosinase (Tyr) is prepared from fluorescent dye FT-OH and m-hydroxy benzyl bromide. The method is used for specifically monitoring Tyr in vitro and in vivo, and is successfully applied to real-time monitoring of trace Tyr in living cells.
The structural general formulas of the fluorescent probe and the compound FL-O-T are as follows:
wherein R is1、R2、R3Hydrogen, alkyl or other common substituents.
The compound FL-O-T can be used as a fluorescent probe for detecting tyrosinase, and is synthesized by nucleophilic substitution reaction of fluorescein derivatives and m-hydroxybenzyl bromide.
The compounds FT-OH and FL-O-T have the following structures:
wherein R is1、R2、R3Hydrogen, alkyl or other common substituents.
The compound FL-O-T can be used as a fluorescent probe for detecting tyrosinase, and is synthesized by nucleophilic substitution reaction of fluorescein derivatives and m-hydroxybenzyl bromide.
The fluorescent probe for detecting tyrosinase (Tyr) has the characteristics of high chemical selectivity, excellent noise ratio signal and the like.
The fluorescent probe for detecting tyrosinase (Tyr) is synthesized by nucleophilic substitution based on fluorescent dyes FT-OH and a Tyr recognition group (m-hydroxyphenyl).
The invention provides a preparation method of a fluorescent probe, which comprises the following steps:
(1) PBr (p-phenylene benzol) prepared from m-hydroxybenzyl alcohol3Bromination reaction to obtain m-hydroxy benzyl bromide.
(2) FT-OH reacts with m-hydroxy benzyl bromide to obtain a compound FL-O-T;
the specific structural formula of the compound is as follows:
the preparation method and the synthetic route of the fluorescent probe FL-O-T for detecting Tyr are as follows:
the invention creatively synthesizes the fluorescent probe FL-O-T by nucleophilic substitution based on the FT-OH and Tyr recognition groups (m-hydroxybenzyl bromide) of the fluorescent dye. The fluorescent probe FL-O-T shows weak fluorescence due to the PET effect, after Tyr enzyme is added into a reaction system, according to the catalytic characteristic, hydroxyphenyl between recognition groups is oxidized into an O-diphenol structure in the presence of molecular oxygen, the structure rapidly generates a 1, 6-rearrangement elimination reaction, and then leaves and releases a fluorophore FT-OH, so that the detection of the fluorescence from weak to strong is realized. The obtained fluorescent probe FL-O-T has the characteristics of good selectivity, strong anti-interference capability, high sensitivity and the like.
The invention also provides a compound for detecting tyrosinase (Tyr). The structural general formula of the compound FL-O-T is as follows:
wherein R is1、R2、R3Hydrogen, alkyl or other common substituents.
The compound FL-O-T can be used as a fluorescent probe for detecting tyrosinase, and is synthesized by nucleophilic substitution reaction of fluorescein derivatives and m-hydroxybenzyl bromide.
The invention also provides a preparation method of the compound for detecting tyrosinase (Tyr), which comprises the following steps:
(1) PBr (p-phenylene benzol) prepared from m-hydroxybenzyl alcohol3Bromination reaction to obtain m-hydroxy benzyl bromide.
(2) FT-OH reacts with m-hydroxy benzyl bromide to obtain a compound FL-O-T.
The invention further provides an application of the fluorescent molecular probe for detecting Tyr in cells.
The invention further provides an application of the fluorescent molecular probe for detecting Tyr in the body of zebra fish.
The invention further provides application of the Tyr detection compound in cell Tyr detection.
The invention further provides application of the Tyr detecting compound in detecting Tyr in zebra fish bodies.
The invention provides a detailed preparation method of a fluorescent probe and a compound for detecting Tyr, which comprises the following steps:
selecting R according to the small molecular compound FL-O-T for detecting Tyr1、R2、R3All are hydrogen, and the description is given by way of example.
The synthesis steps are as follows:
FT-OH is taken as a raw material to be subjected to nucleophilic substitution reaction with m-hydroxy benzyl bromide to obtain FL-O-T.
0.3mmol of FT-OH (R)1、R2、R3Hydrogen) in 20mL of anhydrous DMF (dimethylformamide) and then 0.9mmol of K was added2 CO 3And stirred at 60 ℃ under an argon atmosphere for 10 minutes. Thereafter, 5mL of an anhydrous DMF solution of m-hydroxybenzyl bromide with a concentration of 1.2mmol/5mL was added dropwise. Stirring was continued at 60 ℃ for 5 hours under an argon atmosphere. The progress of the reaction was monitored by TLC. After the reaction is finished, adding water, adjusting the pH value to 5-6 by using dilute hydrochloric acid, extracting by using EA (ethyl acetate) and washing by using water. The organic solution is treated with anhydrous Na2 SO 4Dried and evaporated in vacuo. The residue was purified by column chromatography using EA/PE (ethyl acetate/petroleum ether) to give the target FL-O-T.
The terms:
absorbance is the absorption value.
FL intensity is the fluorescence intensity.
HIS is histidine.
The beneficial technical effects are as follows:
the invention provides a fluorescent probe capable of tracking and monitoring tyrosinase (Tyr) in vivo and in vitro, which overcomes some defects in the related technology, such as the defects of shorter fluorescence emission wavelength, poor stability, poor selectivity and the like of the fluorescent probe. In the invention, a fluorescent probe FL-O-T is synthesized by nucleophilic substitution by utilizing FT-OH and Tyr recognition groups (m-hydroxyphenyl) of fluorescent dyes. Thereby overcoming the defect of poor selectivity of the fluorescent probe; the fluorescent probe has good selectivity on tyrosinase (Tyr), and has the characteristics of strong anti-interference capability, high sensitivity and the like. Meanwhile, the fluorescent probe can be applied to real-time tracking of Tyr in living cells.
The compound FL-O-T for detecting tyrosinase (Tyr) provided by the invention can be used for selectively detecting the Tyr in cells, and has the advantages of good selectivity of the compound FL-O-T on the Tyr, strong anti-interference capability and high sensitivity.
Drawings
FIG. 1 (A) is a graph showing UV absorption spectra of a fluorescent probe FL-O-T before and after reaction with Tyr in PBS buffer (pH =7.4), and FIG. 1 (B) is a graph showing fluorescence emission spectra of FL-O-T before and after reaction with Tyr in PBS buffer (pH = 7.4);
FIG. 2 is a graph showing the high selectivity test exhibited by fluorescent probe FL-O-T, wherein a. blank set; b. ca2+；c. Mg2+；d. Zn2+(ii) a e, Cys; f. a GSH; g. hcy; h. glucose; i. fetal bovine serum; j. human plasma; k. aprotinin; trypsin; m. cellulase; n, alpha-amylase; sulfatase; p, GGT; q. a lipase; r, LAP; s, β -Gal; t. elastase; chymotrypsin; v. ClO4 －；w. H2O2；x. ONOO－；y. TYR。
FIG. 3 is a graph showing the effect of fluorescent probe FL-O-T on the fluorescence imaging of Tyr in HepG2 cells. In the figure, A, C, E, G and I are respectively a bright field imaging graph of FL-O-T in HepG2, B, D, F, H and J are respectively fluorescence imaging graphs in a green channel of FL-O-T, a graph K is a bright field imaging graph of FL-O-T in HepG2 added with kojic acid, and a graph L is a fluorescence imaging graph of FL-O-T in a green channel of HepG2 added with kojic acid; panel M is a graph of FL-O-T effect with HepG2 and kojic acid addition at various times.
FIG. 4 is a graph showing the effect of fluorescent probe FL-O-T on the fluorescence imaging of Tyr in zebra fish. In the figure, A and E are blank composition images; b and F are imaging graphs of FL-O-T and zebra fish for 2 h: c, G is an imaging picture of FL-O-T and zebra fish incubation for 4H, and D, H is an imaging picture of kojic acid addition.
FIG. 5 NMR spectra of compound FL-O-T with deuterated reagent d6-DMSO。
FIG. 6 is a high resolution mass spectrum HRMS (m/z) of compound FL-O-T.
Detailed Description
In order to better understand the present invention, the following examples are further provided to illustrate the present invention, but the present invention is not limited to the following examples.
Example (b): a method for preparing a near-infrared fluorescent molecular probe FL-O-T.
0.3mmol of FT-OH (R)1、R2、R3Hydrogen) in 20mL of anhydrous DMF, and then 0.9mmol of K was added2 CO 3And stirred at 60 ℃ under an argon atmosphere for 10 minutes. Thereafter, 5mL of an anhydrous DMF solution of m-hydroxybenzyl bromide with a concentration of 1.2mmol/5mL was added dropwise. Stirring was continued at 60 ℃ for 5 hours under an argon atmosphere. The progress of the reaction was monitored by TLC. After the reaction is finished, adding water, adjusting the pH value to 5-6 by using dilute hydrochloric acid, extracting by using EA, and washing by using water. The organic solution is treated with anhydrous Na2 SO 4Dried and evaporated in vacuo. The residue was purified by column chromatography using EA/PE to give the target FL-O-T.
Hydrogen spectrum of compound FL-O-T (as shown in FIG. 5), deuterated reagent isd 6-DMSO。
1H NMR (400 MHz, (CD3)2SO): δ 9.54 (s, 1H), δ 9.41 (s, 1H), δ 8.22 (d, 1H), δ 7.86 (t, 1H), δ 7.79 (t, 1H), δ 7.49 (d, 1H), δ 7.20 (m, 2H), δ 6.97 (t, 1H), δ 6.90 (m, 3H), δ 6.77 (m, 3H), δ 6.67 (d, 1H), δ 6.50 (s, 1H), δ 6.38 (m, 2H), δ 6.16 (s, 1H), δ 5.19 (s, 2H), δ 4.91 (s, 2H);
Carbon spectrum of the compound FL-O-T (as shown in FIG. 5), deuterated reagent isd 6-DMSO。
13C NMR (100 MHz, (CD3)2SO): δ 184.48, δ 165.26, δ 163.32, δ 158.76, δ 157.91, δ 157.67, δ 153.89, δ 150.59, δ 137.86, δ 136.53, δ 133.69, δ 131.26, δ 130.54, δ 130.12, δ 130.03, δ 129.86, δ 118.77, δ 118.63, δ 115.51, δ 115.10, δ 114.93, δ 114.79, δ 105.02, δ 101.75, δ 70.52, δ 67.15.
High resolution Mass Spectrometry of Compound FL-O-T (see FIG. 6)
HRMS (ESI) m/z =543.1435 [M]-。
Example of effects:
referring to fig. 1: the optical response of FL-O-T to Tyr was tested under physiological conditions (PBS buffer, 10 mM, pH =7.4, 37 ℃). From fig. 1 (a): FL-O-T (5. mu.M) produced the major absorption band at 460 nm. In Tyr (500 U.mL)-1) After incubation, a new absorption peak at 470nm was observed. Meanwhile, the color of the reaction system changes from colorless to yellow. Further, from fig. 1 (B): FL-O-T showed relatively weak fluorescence at 517 nm under 480 nm light excitation (Φ = 0.031). After incubation for 360 min at Tyr (500 U.mL-1), FL-O-T released FT-OH, and an increase in fluorescence signal observed at 517 nm showed more than 24-fold, indicating that FL-O-T is a fluorescent molecular probe with excellent signal-to-noise ratio.
Referring to fig. 2: is an interference test plot of fluorescent molecular probe FL-O-T in PBS buffer (pH = 7.4). It can be seen from the figure that FL-O-T has very good selectivity to Tyr.
Referring to fig. 3: is an imaging effect graph of a fluorescent probe FL-O-T for detecting Tyr in HepG 2. It can be seen from the figure that the fluorescence signal in the green channel increases with time and that the fluorescence intensity reaches the plateau point at about 120 minutes. In addition, fluorescence becomes markedly weaker in the presence of kojic acid. These cell imaging experiments showed that the fluorescent signal was triggered by endogenous tyrosinase in HepG2 cells, which indicated that FL-O-T was suitable for monitoring tyrosinase activity in living cells.
Referring to fig. 4: is an imaging effect diagram of a fluorescent probe FL-O-T for detecting Tyr in zebra fish. Panel E shows little background fluorescence in the green channel, panel F shows weak fluorescent signal collected after 2 hours incubation of zebrafish with FL-O-T and green fluorescence is distributed almost throughout the body; panel F shows that the fluorescence signal becomes more pronounced after 4 hours of its incubation with FL-O-T; panel H shows that kojic acid significantly suppresses the fluorescence intensity in the green channel. These results demonstrate that FL-O-T is able to track endogenous tyrosinase in organisms.
The invention provides a fluorescent probe FL-O-T for detecting tyrosinase (Tyr), which can be used for detecting Tyr in cells, and overcomes the defects in the related technology, such as the problem that the fluorescent probe is easily influenced by various active oxygen substances. In the invention, a fluorescent probe FL-O-T is synthesized by nucleophilic substitution by utilizing FT-OH and Tyr recognition groups (m-hydroxyphenyl) of fluorescent dyes. The fluorescent probe FL-O-T shows weak fluorescence due to the PET effect, after Tyr enzyme is added into a system, according to the catalytic characteristic, hydroxyphenyl between recognition groups is oxidized into an O-diphenol structure in the presence of molecular oxygen, the structure rapidly generates 1, 6-rearrangement elimination reaction, and then leaves and releases a fluorescein fluorophore, thereby realizing the detection of the fluorescence from weak to strong. The probe has the characteristics of high chemical selectivity, good stability, high sensitivity and the like. Meanwhile, the fluorescent probe can be applied to real-time tracking and monitoring of Tyr in living cells.
The compound FL-O-T for detecting tyrosinase (Tyr) provided by the invention can be used for highly chemoselectively detecting the Tyr in cells, and has the advantages of good selectivity of the compound FL-O-T on the Tyr, strong anti-interference capability and high sensitivity.
The foregoing shows that the basic principles of the invention, its essential features and its essential uses are described. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are given by way of illustration of the principles of the present invention, and that various changes and modifications may be made without departing from the spirit and scope of the invention as defined by the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (5)
1. A compound for detecting tyrosinase has the following structural formula:
wherein R is1、R2、R3Is hydrogen or alkyl.
2. The preparation method of the compound FL-O-T for detecting tyrosinase, according to claim 1, comprises the following steps:
(1) PBr (p-phenylene benzol) prepared from m-hydroxybenzyl alcohol3Carrying out bromination reaction to obtain m-hydroxy benzyl bromide;
(2) reacting fluorescein FT-OH with m-hydroxy benzyl bromide to obtain a compound FL-O-T;
the specific structural formula of the compound is as follows:
wherein R is1、R2、R3Is hydrogen or alkyl.
3. The method of claim 2, wherein: fluorescein 0.3mmol FT-OH was dissolved in 20mL anhydrous DMF and 0.9mmol K was added2CO3Stirring for 10 minutes at 60 ℃ under an argon atmosphere; then, 5mL of anhydrous DMF solution with the concentration of 1.2mmol/5mL of m-hydroxy benzyl bromide is dropwise added; stirring at 60 deg.C for 5 hr under argon atmosphere; the progress of the reaction was monitored by TLC; after the reaction is finished, adding water, adjusting the pH value to 5-6 by using dilute hydrochloric acid, extracting by using EA, and washing by using water; the organic solution is treated with anhydrous Na2SO4Drying and vacuum evaporating; the residue was purified by column chromatography using EA/PE to give the target FL-O-T.
4. The compound of claim 1 as a fluorescent probe for detecting tyrosinase.
5. The compound of claim 1 is used as a fluorescent probe for tracking and monitoring tyrosinase in living cells and zebra fish bodies.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811523187.8A CN109608474B (en) | 2018-12-13 | 2018-12-13 | Compound for detecting tyrosinase and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811523187.8A CN109608474B (en) | 2018-12-13 | 2018-12-13 | Compound for detecting tyrosinase and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109608474A CN109608474A (en) | 2019-04-12 |
| CN109608474B true CN109608474B (en) | 2021-02-26 |
Family
ID=66007562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811523187.8A Active CN109608474B (en) | 2018-12-13 | 2018-12-13 | Compound for detecting tyrosinase and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109608474B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112255208B (en) * | 2020-10-09 | 2023-01-10 | 安阳工学院 | Compound for detecting tyrosinase and application thereof |
| CN112341472B (en) * | 2020-11-20 | 2021-11-09 | 济南大学 | Tyrosinase activated double-quenching diagnosis and treatment prodrug and preparation thereof |
| CN115368316A (en) * | 2021-05-19 | 2022-11-22 | 北京工商大学 | Naphthalene ring tyrosinase fluorescent probe |
| CN113461609B (en) * | 2021-07-29 | 2022-05-17 | 中国药科大学 | Sulfatase-responsive AIE nano probe and preparation method and application thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5248582A (en) * | 1988-09-07 | 1993-09-28 | Fuji Photo Film Co., Ltd. | Positive-type photoresist composition |
| JP2001288189A (en) * | 2000-03-31 | 2001-10-16 | Bunshi Biophotonics Kenkyusho:Kk | Caged fluorescein |
| WO2009027604A1 (en) * | 2007-07-13 | 2009-03-05 | Laboratoires Synth-Innove | Polycarboxylate phtaleins used as fluorescent dyes and a method for the preparation thereof |
| CN106279124A (en) * | 2016-08-12 | 2017-01-04 | 中国科学院化学研究所 | A kind of for fluorescent probe detecting tryrosinase and preparation method and application |
| CN107602498A (en) * | 2017-07-26 | 2018-01-19 | 华南理工大学 | A kind of fluorescence probe and preparation method thereof with detected in tyrosinase in application |
-
2018
- 2018-12-13 CN CN201811523187.8A patent/CN109608474B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5248582A (en) * | 1988-09-07 | 1993-09-28 | Fuji Photo Film Co., Ltd. | Positive-type photoresist composition |
| JP2001288189A (en) * | 2000-03-31 | 2001-10-16 | Bunshi Biophotonics Kenkyusho:Kk | Caged fluorescein |
| WO2009027604A1 (en) * | 2007-07-13 | 2009-03-05 | Laboratoires Synth-Innove | Polycarboxylate phtaleins used as fluorescent dyes and a method for the preparation thereof |
| CN106279124A (en) * | 2016-08-12 | 2017-01-04 | 中国科学院化学研究所 | A kind of for fluorescent probe detecting tryrosinase and preparation method and application |
| CN107602498A (en) * | 2017-07-26 | 2018-01-19 | 华南理工大学 | A kind of fluorescence probe and preparation method thereof with detected in tyrosinase in application |
Non-Patent Citations (1)
| Title |
|---|
| "Highly chemoselective fluorescent probe for the detection of tyrosinase in living cells and zebrafish model";Sisi Hu et al.;《Sensors and Actuators B: Chemical》;20181221;第283卷;第873-880页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109608474A (en) | 2019-04-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109608474B (en) | Compound for detecting tyrosinase and preparation method and application thereof | |
| CN110283583B (en) | Gamma-glutamyl transpeptidase responsive molecular probe and application thereof | |
| CN106967102B (en) | A kind of enhanced fluorescence probe of hydrogen peroxide based on Rhodamine Derivatives | |
| CN110357865B (en) | Near-infrared fluorescent probe for detecting hNQO1 enzyme, and synthetic method and application thereof | |
| CN105038762B (en) | Ratio-dependent fluorescent probe for detecting hydrogen peroxide and application of ratio-dependent fluorescent probe | |
| CN109438319B (en) | Compound for detecting leucine aminopeptidase and preparation method and application thereof | |
| CN113801105B (en) | Mitochondrion targeted peroxynitrite/bisulfite dual-response fluorescent probe | |
| Han et al. | Rational design of a lysosomal-targeted ratiometric two-photon fluorescent probe for imaging hydrogen polysulfides in live cells | |
| CN113004220B (en) | Esterase detection fluorescent probe, preparation method and application | |
| CN112778288B (en) | Near-infrared solid-state light-emitting fluorescent probe and preparation method and application thereof | |
| CN113637048B (en) | Two-photon fluorescent probe of gamma-glutamyl transpeptidase and preparation method and application thereof | |
| CN108727265A (en) | A kind of difunctional fluorescence probe and its preparation method and application of detection formaldehyde and pH | |
| CN109608495B (en) | Compound for detecting HNO and preparation method and application thereof | |
| CN109734710A (en) | A kind of fluorescence probe detecting cysteine and its synthetic method and application | |
| CN111635385B (en) | Mitochondrion-targeted two-photon excitation near-infrared emission hydrogen sulfide fluorescent probe and preparation method and application thereof | |
| CN111039866B (en) | Golgi-targeted hydrogen sulfide fluorescent probe, and preparation method and application thereof | |
| CN109265440B (en) | Preparation method of azacyclo fluorescent probe and application of azacyclo fluorescent probe in hydrogen sulfide detection | |
| CN110343099B (en) | Organic compound based on two-photon fluorophore and application | |
| CN108752371A (en) | A kind of two-photon hydrogen peroxide fluorescence probe based on quinoline | |
| CN111087362A (en) | Fluorescent probe for detecting formaldehyde with high selectivity, and synthetic method and application thereof | |
| CN110156695A (en) | It is a kind of detect cysteine fluorescence probe and its application | |
| CN113072528B (en) | Near-infrared ratio fluorescent probe for reversibly detecting bisulfite/formaldehyde, preparation method and application | |
| CN112409346B (en) | Used for intracellular H2Fluorescent probe for S detection and preparation method thereof | |
| CN117603203B (en) | Ratio fluorescent probe and preparation method and application thereof | |
| CN115894427A (en) | Near-infrared frequency up-conversion fluorescent probe, preparation method thereof and application thereof in detection of biological thiol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |