CN111100184B - Fluorescent probe for detecting superoxide anion free radicals in peroxisome and application thereof - Google Patents

Fluorescent probe for detecting superoxide anion free radicals in peroxisome and application thereof Download PDF

Info

Publication number
CN111100184B
CN111100184B CN201911320428.3A CN201911320428A CN111100184B CN 111100184 B CN111100184 B CN 111100184B CN 201911320428 A CN201911320428 A CN 201911320428A CN 111100184 B CN111100184 B CN 111100184B
Authority
CN
China
Prior art keywords
fluorescent probe
superoxide anion
peroxisome
free radicals
anion free
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
Application number
CN201911320428.3A
Other languages
Chinese (zh)
Other versions
CN111100184A (en
Inventor
唐波
丁琪
李平
王昕�
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shandong Normal University
Original Assignee
Shandong Normal University
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Shandong Normal University filed Critical Shandong Normal University
Priority to CN201911320428.3A priority Critical patent/CN111100184B/en
Publication of CN111100184A publication Critical patent/CN111100184A/en
Application granted granted Critical
Publication of CN111100184B publication Critical patent/CN111100184B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
    • 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"
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
    • 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
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2410/00—Assays, e.g. immunoassays or enzyme assays, involving peptides of less than 20 animo acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Immunology (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Urology & Nephrology (AREA)
  • Pathology (AREA)
  • Biomedical Technology (AREA)
  • General Physics & Mathematics (AREA)
  • Analytical Chemistry (AREA)
  • Hematology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • Microbiology (AREA)
  • Food Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • Cell Biology (AREA)
  • Biotechnology (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Optics & Photonics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)

Abstract

The invention provides a fluorescent probe for detecting superoxide anion free radicals in peroxisomes and application thereof, and belongs to the technical field of detection and analysis. The invention designs a method for using caffeic acid as O2 ·‑The fluorescent probe for detecting superoxide anion free radicals, which takes small peptide (QSKL) as a target group of peroxisome, has the following structural formula:
Figure DDA0002326998320000011
the fluorescent probe is particularly suitable for detecting superoxide anion free radicals at the cellular structure level, particularly the subcellular structure level (such as peroxisome), and has good practical application value.

Description

Fluorescent probe for detecting superoxide anion free radicals in peroxisome and application thereof
Technical Field
The invention belongs to the technical field of detection and analysis, and particularly relates to a fluorescent probe for detecting superoxide anion free radicals in peroxisomes and application thereof.
Background
The information disclosed in this background of the invention is only for enhancement of understanding of the general background of the invention and is not necessarily to be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person skilled in the art.
Depression is a global mental disease with high morbidity, recurrence rate, mortality and disability rate, and seriously harms human health. Unfortunately, the current understanding of the pathophysiology of depression is still very poor. In order to effectively prevent and treat the depression, the occurrence and development process of the depression must be thoroughly understood. The two-photon fluorescence imaging technology has the advantages of high spatial resolution, small light damage to biological tissues, deeper tissue penetrating capacity and the like, and becomes an important imaging method for researching occurrence and development of biological events and diseases in cells and living bodies from the molecular level.
Peroxisomes, which are important organelles in cells, can produce Reactive Oxygen Species (ROS) and scavenge ROS, and play a crucial role in maintaining the redox balance in cells. Superoxide anion radical (O)2 ·-) Is the first ROS produced in the organism, and the content of the ROS directly represents the level of oxidative stress. Thus, O in peroxisomes was explored2 ·-The role in the development of depression is crucial to understanding the pathogenesis of depression. However, it is currently used for detecting O in peroxisomes2 ·-The tool (2) has not been reported.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a fluorescent probe for detecting peroxisome superoxide anion free radicals and application thereof. The invention designs a method for using caffeic acid as O2 ·-The recognition group and the fluorophore take small peptide (QSKL) as a target group of peroxisome and are used for detecting the fluorescent probe of the superoxide anion free radical, and the fluorescent probe is particularly suitable for detecting the superoxide anion free radical at the cellular structure level, particularly the subcellular structure level (such as peroxisome), so the fluorescent probe has good practical application value.
In order to achieve the technical purpose, the technical scheme adopted by the invention is as follows:
in a first aspect of the invention, a fluorescent probe is provided, which comprises caffeic acid and a small molecule peptide coupled with the caffeic acid.
The small molecule peptide is used as a positioning group for positioning peroxisome; preferably, the amino acid sequence of the small molecule peptide is selected from the group consisting of: comprises or consists of a sequence of QSKL (Gln-Ser-Lys-Leu); more preferably, the small molecule peptide amino acid sequence is QSKL.
Further, the structural formula of the fluorescent probe is as follows:
Figure BDA0002326998300000021
in a second aspect of the invention, there is provided the use of the above-described fluorescent probe for detecting superoxide anion radicals.
The application environment includes, but is not limited to, biological organs, tissues, cells, and subcellular structures.
Wherein the subcellular structure is a peroxisome.
In a third aspect of the present invention, there is provided a method for detecting superoxide anion radicals, the method comprising: and incubating the fluorescent probe and a sample to be detected together, and carrying out fluorescence imaging.
Wherein the incubation treatment conditions are as follows: the incubation temperature is 30-40 ℃, and the incubation time is 0.1-0.5 h.
The invention has the beneficial technical effects that:
the invention reports a fluorescent probe for detecting superoxide anion free radicals in a subcellular structure in a cell for the first time. The detection process does not need to add other chemical substances, has simple operation and small cytotoxicity and is beneficial to intracellular detection. Meanwhile, the fluorescent probe is simple to synthesize, sensitive in detection, high in speed and good in selectivity, and does not need long-time incubation in the detection process. The fluorescent probe of the invention realizes the imaging analysis of the cerebral apoplexy of the tristimania mice on the living body levelO in peroxisome2 ·-Thus, the method has good practical application value.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, illustrate exemplary embodiments of the invention and together with the description serve to explain the invention and not to limit the invention.
FIG. 1 is a graph showing the optical properties of a fluorescent probe in example 1 of the present invention; wherein FIG. 1A shows the fluorescent probe in the presence of O2 ·-In the case of the sample, an absorption peak at about 370nm was observed; FIG. 1B shows fluorescent probes in the presence of O2 ·-Fluorescence intensity at 495nm under single photon 370nm excitation; FIG. 1C shows fluorescent probes in the presence of O2 ·-Fluorescence intensity at 495nm under two-photon 800nm excitation.
FIG. 2 is an image of a cell in example 1 of the present invention; wherein, FIG. 2A is an image of cells of a control group, which are incubated by adding probes into PC12 cells; FIG. 2B shows a stimulated group, in which PC12 cells were first stimulated with 2-Me to produce O2 ·-Adding a probe to incubate a cell imaging graph; FIG. 2C shows the clearance group, in which PC12 was first stimulated with 2-Me to generate O2 ·-Then adding a scavenger Tiron to remove O2 ·-Finally, adding a cell imaging graph after probe incubation; FIG. 2D is a graph showing the data output of the fluorescence intensity of FIGS. 2A, 2B, and 2C.
FIG. 3 is an image of a living body in embodiment 1 of the present invention; wherein, fig. 3A is a two-dimensional plan view of two-photon 3D imaging of normal mice after intraperitoneal injection of probes in a control group; FIG. 3B is a two-dimensional plan view of two-photon 3D imaging of depressed mice after intraperitoneal injection of a probe in an experimental group; FIG. 3C is a two-photon 3D imaging of FIG. 3A; FIG. 3D is a two-photon 3D imaging diagram of FIG. 3B; FIG. 3E is a graph of fluorescence intensity data output of FIGS. 3A and 3B.
FIG. 4 is a mass spectrum of the fluorescent probe in example 1 of the present invention.
Detailed Description
It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the disclosure. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of example embodiments according to the present application. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, and it should be understood that when the terms "comprises" and/or "comprising" are used in this specification, they specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof, unless the context clearly indicates otherwise.
The present invention will now be further described with reference to specific examples, which are provided for the purpose of illustration only and are not intended to be limiting. If the experimental conditions not specified in the examples are specified, the conditions are generally as usual or as recommended by the reagents company; reagents, consumables and the like used in the following examples are commercially available unless otherwise specified.
As previously mentioned, it is currently used for the detection of O in peroxisomes2 ·-The tool (2) has not been reported.
In view of this, the present invention provides a fluorescent probe for detecting superoxide anion radicals and applications thereof. The invention designs a method for using caffeic acid as O2 ·-The fluorescent probe for detecting superoxide anion free radicals, which takes small peptide (QSKL) as a target group of peroxisome, is particularly suitable for detecting superoxide anion free radicals at the cellular structure level, particularly the subcellular structure level (such as organelles).
In one exemplary embodiment of the present invention, a fluorescent probe is provided, which includes caffeic acid, and a small molecule peptide coupled to caffeic acid.
In yet another embodiment of the invention, the small molecule peptide is used as a targeting group for localization of peroxisomes; preferably, the amino acid sequence of the small molecule peptide is selected from the group consisting of: comprises or consists of a sequence of QSKL (Gln-Ser-Lys-Leu); more preferably, the small molecule peptide amino acid sequence is QSKL.
In another embodiment of the present invention, the structural formula of the fluorescent probe is as follows:
Figure BDA0002326998300000051
the positioning and identifying mechanism of the fluorescent probe is as follows: SKL (localization signal peptide PTS1) is a localization group of peroxisome, can specifically act with PEX protein on a peroxisome membrane, and enters the peroxisome interior through a transmembrane transport mode, thereby realizing the localization function.
When with O2 ·-During reaction, the catechol structure with caffeic acid residue as electron donor is changed into electron withdrawing catechol, and the electron distribution of the probe is changed to result in fluorescence change, so as to specifically detect O in peroxisome2 ·-The level of (c) varies.
It should be noted that, the sequence of the peroxisome localization signal peptide PTS1 is selected and obtained through research, caffeic acid is used as a fluorescence recognition group, and the caffeic acid is easily interfered by small molecular peptides of the localization group, so that the localization function of the caffeic acid on peroxisome is met when the localization group is selected, and the interference on the fluorescence recognition group is avoided, and therefore QSKL is selected as the localization group.
In another embodiment of the present invention, the fluorescent probe is used for detecting superoxide anion free radicals.
In yet another embodiment of the present invention, the application environment includes, but is not limited to, biological organs, tissues, cells and subcellular structures.
In yet another embodiment of the invention, the subcellular structure is a peroxisome.
In yet another embodiment of the present invention, there is provided a method for detecting superoxide anion radicals, the method comprising: and incubating the fluorescent probe and a sample to be detected together, and carrying out fluorescence imaging.
Wherein the incubation treatment conditions are as follows: the incubation temperature is 30-40 ℃, and the incubation time is 0.1-0.5 h.
The invention is further illustrated by the following examples, which are not to be construed as limiting the invention thereto. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. The following examples are test methods in which specific conditions are indicated, and are generally carried out under conventional conditions. It should be noted that the fluorescent probe in this example was synthesized and provided by bio-engineering (shanghai) corporation, and its mass spectrum is shown in fig. 4.
Example 1
A fluorescent probe having the structure:
Figure BDA0002326998300000071
effect verification:
optical properties of embodiments of the present invention. Adding O2 ·-Thereafter, the probe (TCP) showed an absorption peak at about 370 nm. (FIG. 1A). As shown in FIG. 1B, under the excitation of a single photon at 370nm, the fluorescence intensity of TCP at 495nm is weak, and the fluorescence intensity of TCP is equal to that of 20 mu M O2 ·-After incubation together, the fluorescence intensity of the probe at 495nm was significantly increased, which was 4 times the initial fluorescence intensity. As shown in FIG. 1C, the fluorescence intensity of TCP at 495nm was enhanced by more than 8 times under two-photon 800nm excitation.
Experiments of embodiments of the invention in cells. We first used 0.1. mu.g/mL 2-Me (to cause oxidative stress in cells to produce O)2 ·-) PC12 cells were incubated for 15min, followed by addition of TCP (20. mu.M) followed by incubation for 30min, followed by washing off the extracellular residual probe with PBS and fluorescence imaging. We observed a three-fold increase in blue fluorescence intensity in the experimental group stimulated with 2-Me compared to the control group. To verify that the change in blue fluorescence signal was indeed due to O2 ·-Caused by a change in concentration of (c), we again used specificityScavenger Tiron (scavenge O)2 ·-) The cells are treated and imaged after 30min, and the blue fluorescence intensity of the cells is obviously reduced. The above experimental results demonstrate that intracellular O can be observed by using the change in fluorescence intensity of TCP2 ·-The concentration of (c) was varied (as shown in fig. 2).
Experiments of the embodiments of the present invention in vivo. The normal mice and the depressed mice are injected with TCP (200 mu M) by intraperitoneal injection, and the brains of the mice are imaged by a two-photon microscope after 30 min. We found that the fluorescence intensity of the model group is obviously enhanced compared with that of the normal group, which indicates that the brain of the mouse with depression has O2 ·-The content was significantly increased (as shown in fig. 3). Through the experiments, the intracerebral O of the depressed mice is analyzed by fluorescence imaging for the first time2 ·-The level is obviously higher than that of normal mice. This result provides direct evidence for a positive correlation between oxidative stress and the extent of depression.
The invention is not the best known technology.
The above embodiments are merely illustrative of the technical ideas and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.

Claims (4)

1. A fluorescent probe is characterized by consisting of caffeic acid and small molecular peptides coupled with the caffeic acid;
the small molecule peptide is used for positioning peroxisome;
the amino acid sequence of the small molecule peptide is QSKL;
the structural formula of the fluorescent probe is as follows:
Figure FDA0002991993420000011
2. use of the fluorescent probe according to claim 1 for detecting superoxide anion radicals in peroxisomes, excluding diagnosis and treatment of diseases.
3. A method of detecting superoxide anion radicals in a peroxisome, said method comprising: incubating the fluorescent probe of claim 1 with a sample to be tested for fluorescence imaging; the methods do not involve diagnosis or treatment of disease.
4. The method for detecting superoxide anion radicals in peroxisomes of claim 3, wherein incubation conditions are: the incubation temperature is 30-40 ℃, and the incubation time is 0.1-0.5 h.
CN201911320428.3A 2019-12-19 2019-12-19 Fluorescent probe for detecting superoxide anion free radicals in peroxisome and application thereof Active CN111100184B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201911320428.3A CN111100184B (en) 2019-12-19 2019-12-19 Fluorescent probe for detecting superoxide anion free radicals in peroxisome and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201911320428.3A CN111100184B (en) 2019-12-19 2019-12-19 Fluorescent probe for detecting superoxide anion free radicals in peroxisome and application thereof

Publications (2)

Publication Number Publication Date
CN111100184A CN111100184A (en) 2020-05-05
CN111100184B true CN111100184B (en) 2021-08-17

Family

ID=70423685

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201911320428.3A Active CN111100184B (en) 2019-12-19 2019-12-19 Fluorescent probe for detecting superoxide anion free radicals in peroxisome and application thereof

Country Status (1)

Country Link
CN (1) CN111100184B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114456079B (en) * 2021-12-23 2023-06-23 山东师范大学 Fluorescent probe compound, preparation method and application of fluorescent probe compound as superoxide anion indicator

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101012207A (en) * 2007-01-04 2007-08-08 山东师范大学 Fluorescent probe for detecting ultra-oxygen anion free radical, synthesis method and use
CN101544749A (en) * 2009-04-28 2009-09-30 江南大学 Preparation method for biodegradable fluorescent polyester multipolymer
CN105154071A (en) * 2015-10-16 2015-12-16 山东师范大学 Fluorescent probe as well as preparation method and application thereof
CN107337681A (en) * 2017-07-28 2017-11-10 厦门大学 A kind of superoxide anion probe and its preparation method and application

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104371707A (en) * 2014-10-31 2015-02-25 山东师范大学 Fluorescent probe and preparation method thereof, and application in detecting superoxide anions
CN108239286A (en) * 2018-01-25 2018-07-03 南京医科大学 Silanization carbon quantum dot surface caffeic acid molecularly imprinted polymer, preparation method and its application

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101012207A (en) * 2007-01-04 2007-08-08 山东师范大学 Fluorescent probe for detecting ultra-oxygen anion free radical, synthesis method and use
CN101544749A (en) * 2009-04-28 2009-09-30 江南大学 Preparation method for biodegradable fluorescent polyester multipolymer
CN105154071A (en) * 2015-10-16 2015-12-16 山东师范大学 Fluorescent probe as well as preparation method and application thereof
CN107337681A (en) * 2017-07-28 2017-11-10 厦门大学 A kind of superoxide anion probe and its preparation method and application

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
Antioxidant Activities of Caffeic Acid and Its Related Hydroxycinnamic Acid Compounds;Jiang Hong Chen等;《J. Agric. Food Chem》;19970716;第2374-2378页 *
In situ visualization of peroxisomal peroxynitrite in the livers of mice with acute liver injury induced by carbon tetrachloride using a new two-photon fluorescent probe;Yongqing Zhou等;《Chem. Commun.》;20190516;第6767-6770页 *
Oxidative Damage of Tryptophan Hydroxylase‑2 Mediated by Peroxisomal Superoxide Anion Radical in Brains of Mouse with Depression;Qi Ding等;《JACS》;20201125;20201125 *
Pex5p Binding Affinities for Canonical and Noncanonical PTS1 Peptides;Ernest L. Maynard等;《PROTEINS: Structure, Function, and Bioinformatics》;20040402;第856-861页 *
Versatile Fluorescent Probes for Imaging the Superoxide Anion in Living Cells and In Vivo;Haibin Xiao等;《Kurzaufsatz》;20190629;第4244-4258页 *

Also Published As

Publication number Publication date
CN111100184A (en) 2020-05-05

Similar Documents

Publication Publication Date Title
Li et al. Two-photon fluorescent probe for revealing drug-induced hepatotoxicity via mapping fluctuation of peroxynitrite
Collins ImageJ for microscopy
Wei et al. Recent advances in the chemical imaging of human fingermarks (a review)
Ozaki Medical application of Raman spectroscopy
CN103805170A (en) Specific fluorescent probe for identifying hydrogen sulfide and application of probe
Ou et al. Methods of measuring enzyme activity ex vivo and in vivo
Bordbar et al. Binding and fluorescence study on interaction of human serum albumin (HSA) with cetylpyridinium chloride (CPC)
Bonnin et al. Novel secondary ion mass spectrometry methods for the examination of metabolic effects at the cellular and subcellular levels
CN110066655B (en) Silver-doped carbon quantum dot and preparation method and application thereof
CN112500386B (en) Near-infrared HClO fluorescent probe based on piroctone olamine, preparation and application thereof
CN111100184B (en) Fluorescent probe for detecting superoxide anion free radicals in peroxisome and application thereof
Long et al. Fluorinated near-infrared fluorescent probes for specific detection of Hg 2+ in an aqueous medium and mitochondria of living cells
CN106929006B (en) It is a kind of using naphthalimide as the identification cysteine of parent nucleus and homocysteine fluorescence probe and its preparation and application
CN110243794A (en) A kind of fluorescence probe for detecting sulfur dioxide and its application based on graphene quantum dot
CN110963995B (en) Double-color fluorescent probe and synthetic method and application thereof
Long et al. On-site discrimination of biothiols in biological fluids by a novel fluorescent probe and a portable fluorescence detection device
CN102914527B (en) Method for detecting content of free tryptophan in tryptophan and serum sample
CN105503768B (en) The preparation method of the fluorescence of alpha ketoglutaric acids/ultraviolet molecular probe and its application in biological specimen
Qu et al. Strong red fluorescent probe for detecting chymotrypsin activity in vivo and in vitro
CN109852383A (en) The fluorescence probe and its preparation method and application for rapidly and efficiently responding glutathione based on fullerene
Hou et al. Photo-crosslinked hydrogel as a sensing platform for sensitive detection of free bilirubin in urine samples
CN113416540B (en) Carbon spot applied to detection of drug-induced deafness reagent and preparation method thereof
US9809837B2 (en) Method for evaluating suitability of duodenal fluid sample as sample for detecting pancreatic fluid-derived components
CN105669661B (en) A kind of cysteine detection reagent and preparation method thereof
CN107462534B (en) A kind of system and its detection method detecting biological sulfhydryl compound

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