CN106800796B - The preparation method of amphipathic asymmetry double ion imide dye and its application for marking cell membrane - Google Patents
The preparation method of amphipathic asymmetry double ion imide dye and its application for marking cell membrane Download PDFInfo
- Publication number
- CN106800796B CN106800796B CN201710013730.9A CN201710013730A CN106800796B CN 106800796 B CN106800796 B CN 106800796B CN 201710013730 A CN201710013730 A CN 201710013730A CN 106800796 B CN106800796 B CN 106800796B
- Authority
- CN
- China
- Prior art keywords
- double ion
- imide
- amphipathic
- preparation
- tetracarboxylic dianhydride
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
-
- 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
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Materials Engineering (AREA)
- Biomedical Technology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
Application the invention discloses amphipathic asymmetric double ion imide dye for belonging to biomarker technical field technical field and preparation method thereof and in terms of active somatic cell membrane marker fluorescence imaging.The unmodified tetracarboxylic dianhydride of the tetrabasic carboxylic acid dicarboxylic anhydride or island position that the present invention is replaced using island position chlorine or bromine is fluorescent chromophore, introduces hydrophobic alkyl chain respectively in both-end and hydrophilic double ion group obtains a kind of amphipathic asymmetric double ion imide fluorescent dye.The introducing of double ion group improves the whole water solubility of structure with biocompatibility and reduces the cell toxicant of structure entirety.All dyestuffs are used equally in vitro and in vivo cell membrane mark fluorescent to be imaged.It is good due to using photochemical stability, launch wavelength near-infrared is used as fluorescent chromophore, and the electrostatic force of double ion structure and membrane structure, its significant notation time is greatly improved during biological living cell membrane imaging, the duration was up to 72 hours or more.
Description
Technical field
The invention belongs to biomarker technical fields, contaminate in particular to amphipathic asymmetric double ion acid imide
Material and preparation method thereof and the application in terms of active somatic cell membrane marker fluorescence imaging.
Background technique
In biology and medical research field, bioluminescence imaging is due to its detecting instrument mature, high sensitivity, right
Than spend the advantages that high, high resolution, imaging is intuitive, image taking speed is fast and lossless detection physiology and in terms of it is wide
General application.Bioluminescence imaging relies on the development of optical molecular probe, especially nontoxic, does not influence the function of biology, long-acting work
Luminescent dye molecule.One Zhang Zhiguan, clearly static or dynamic image can be used to analyze cell or organism is special
Determine the information such as the feature in region, the expression of state or even specific molecular, distribution.And wherein cell membrane is to prevent extracellular substances
It is freely accessible to the barrier of cell, it ensure that the relatively stable of intracellular environment, enable various biochemical reaction orderly functions.Together
When with ambient enviroment information must occur for cell, substance be exchanged with energy, specific physiological function could be completed.Therefore it develops
One kind label cell membrane, effect stability, long-acting dynamic monitoring are particularly significant to life science.
In numerous fluorescence organic compound objects and its derivative has good light, heat, chemical stability, fluorescence volume
Sub- yield is high, and fluorescence emission peak is narrow and launch wavelength can effectively avoid the background interference of cell itself, improves signal-to-noise ratio.By
In its excellent dyeability, laser dye and biological fluorescent labeling field have been widely used in it.For current business
The bad stability of the cell membrane dyestuff of change, action time short defect, therefore when developing a kind of good stabilizability, label effect
Between specific marker fluorescent dye that is longer and being capable of dynamic monitoring cell membrane be of great significance.
Summary of the invention
The purpose of the present invention is to provide a kind of light, thermal stability is good, water-soluble good, structure it is programmable it is amphipathic not
Symmetrical double ion imide dye and preparation method thereof, such dyestuff can be used for active somatic cell membrane marker, and can be realized pair
Living cells film long-time dynamic monitoring.
The technical solution of the present invention is as follows: using light, class chromophore, fatty amine, the N of good heat stability, N- dimethyl
Ethylenediamine is raw material, and one-step method is prepared the asymmetric imide derivative that can continue functionalization, then passes through tertiary amino
Double ion group is further introduced dye molecule by the open loop for causing sultones.The introducing of double ion group both increases structure
Water solubility, and provide the polar group that can be combined with film surface, and double ion group electrolyte with higher
Buffer capacity and low cytotoxicity, this all improves the action time of dyestuff in the cell.It is balanced due to reasonably designing
The hydrophobic and hydrophilic segment of imide dye structure, dye molecule can be assembled into partial size 100-200nm's in aqueous solution
Contain the vesica of negative ions in surface.This vesica can enter cell, lysosomal acid in the cell by endocytosis
After the system of solutions dresses up unimolecule under interior environment, intracellular membrane structure is incorporated, to mark intracellular membrane structure.In living insects
Under acidic environment in enteron aisle, this vesica system of solutions dresses up unimolecule, to directly mark living body enterocyte plasma membrane.
Amphipathic asymmetric double ion imide dye structural formula of the present invention are as follows:
Wherein, R1=H, R2=Cl or Br；Or R1=R2Any one in=H, Br or Cl；M=1-5.
Above-mentioned amphipathic asymmetric double ion imide dye the preparation method comprises the following steps: causing sultones by tertiary amino
Open loop asymmetric imide derivative of the double ion group introducing with tertiary amine group is obtained into amphipathic asymmetric double ion
Imide dye.
Further, the asymmetric imide derivative with tertiary amine group and 1,3-propane sultone are with molar ratio 1:1-
10 in methylene chloride, and under nitrogen protection, room temperature back flow reaction obtains amphipathic asymmetric double ion imide dye.
Further, the preparation method of the asymmetric imide derivative with tertiary amine group is by tetrabasic carboxylic acid two
Anhydride fluorescent core and octylame are dissolved in methanol, and under nitrogen protection, first time temperature rising reflux reacts, concentrated, flushing and vacuum
Dry, after obtaining dark red solid, with imidazoles, N, N- dimethyl-ethylenediamine, under nitrogen protection, second of temperature rising reflux are anti-
It answers, obtains the asymmetric imide derivative with tertiary amine group, wherein tetracarboxylic dianhydride's class fluorescent core, octylame, N, N- bis-
Methyl ethylenediamine is with molar ratio 1:1-5:1-5.
Preferably, tetracarboxylic dianhydride's class fluorescent core is 1, the 7- bis- chloro- 3 that island position replaces, 4,9,10- tetracarboxylic acids
Acid dianhydride, the bromo- 3,4,9,10- tetracarboxylic dianhydride of 1,7- bis-, the chloro- 3,4,9,10- tetracarboxylic dianhydride of 1,6,7,12- tetra-, 1,
In the bromo- 3,4,9,10- tetracarboxylic dianhydride of 6,7,12- tetra- or the unsubstituted tetracarboxylic dianhydride in island position any one or it is several
Kind.
Preferably, the first time and second temperature rising reflux range of reaction temperature are 85 DEG C to 120 DEG C, and the reaction time is
10-12h。
Alternatively, the preparation method of the asymmetric imide derivative with tertiary amine group is tetracarboxylic dianhydride
Class fluorescent core, octylame, N, N- dimethyl-ethylenediamine with molar ratio 1:1-5:1-5 in toluene, under nitrogen protection, temperature rising reflux
Reaction, obtains the asymmetric imide derivative with tertiary amine group.
Preferably, tetracarboxylic dianhydride's class fluorescent core is 1, the 7- bis- chloro- 3 that island position replaces, 4,9,10- tetracarboxylic acids
Acid dianhydride, the bromo- 3,4,9,10- tetracarboxylic dianhydride of 1,7- bis-, the chloro- 3,4,9,10- tetracarboxylic dianhydride of 1,6,7,12- tetra-, 1,
In the bromo- 3,4,9,10- tetracarboxylic dianhydride of 6,7,12- tetra- or the unsubstituted tetracarboxylic dianhydride in island position any one or it is several
Kind.
Preferably, the temperature rising reflux range of reaction temperature is 85 DEG C to 120 DEG C, reaction time 10-12h.
Above-mentioned amphipathic asymmetric double ion imide dye is used in vivo marker cell membrane fluorescence imaging.
The application that above-mentioned amphipathic asymmetric double ion imide dye is imaged in living cells inner membrance mark fluorescent.
The present invention has following advantageous effects:
1, amphipathic asymmetric double ion imide dye UV absorption and fluorescent emission provided by the invention can be with
The interference of autofluorescence background in bio-imaging is effectively avoided, signal-to-noise ratio is improved.
2, amphipathic asymmetric double ion imide dye provided by the invention has water solubility, introduces potential resistance to electrolyte contamination
The strong double ion group of buffer capacity and have lower bio-toxicity.
3, amphipathic asymmetric double ion imide dye provided by the invention, due to using light, good heat stability
Do fluorescent chromophore, thus living cells inner membrance can be marked with long-time stable, mark the duration up to 72 hours or more.
4, amphipathic asymmetric double ion imide dye design provided by the invention is simple, and synthesis is convenient, raw material warp
Ji, structure good light stability, toxicity is low, and the cell membrane of living tissue can be marked by simple mode, is a kind of new
The long-time specific marker active somatic cell film dyestuff of type.
Detailed description of the invention
The fluorescent chromophore used in Fig. 1 present invention.
The reacting flow chart of Fig. 2 synthesizing amphipathic asymmetry double ion imide dye.
The nucleus magnetic hydrogen spectrum characterization of product in Fig. 3 embodiment 1.
The nuclear-magnetism carbon stave sign of product in Fig. 4 embodiment 1.
The mass spectral characteristi of product in Fig. 5 embodiment 1.
Fig. 6 is the spectrum property of amphipathic symmetrical imide dye P1 in embodiment 1.
Fig. 7 is the confocal fluorescent imaging that P1 marks HeLa cell membrane in embodiment 1.
Fig. 8 is the confocal fluorescent imaging that P1 marks insect living body gut plasma membrane living in embodiment 1.
Fig. 9 is the cytotoxicity test of P1 in embodiment 1.
Schematic diagram of the amphipathic asymmetric double ion acid imide of Figure 10 in conjunction with cell membrane.
Specific embodiment
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..Unless otherwise specified, embodiment
In it is raw materials used be commercial goods.
Embodiment 1
1,3,4,9,10- tetracarboxylic dianhydride 527mg (1mmol), octylame 130mg (1mmol) are dissolved in 15ml methanol,
It is added in 50mL there-necked flask, then seals with rubber stopper system, under nitrogen protection, magnetic agitation 30min is warming up to 85 DEG C
Reflux.It is reacted by 12h.Reactant is rinsed with ethyl alcohol and is precipitated after concentration.After concentration vacuum drying, obtain dark red
Color solid.
By above-mentioned dark red solid, imidazoles 10g, N, N- dimethyl-ethylenediamine 106mg (1.2mmol about 132ul) is added to
In there-necked flask, system is then sealed with rubber stopper, under nitrogen protection, is warming up to 120 DEG C of back flow reactions.It is reacted by 12h.Instead
It answers object after concentration, precipitating is obtained by filtration, after a large amount of water washing, picks up second point with column chromatography silica gel post separation,
Eluent chloroform.After concentration vacuum drying, 218mg product 1 (yield 26%) is obtained.
2, above-mentioned 1 57mg of product (0.1mmol) is added in polymerization pipe, adds 10ml methylene chloride, is placed in room temperature water
It is stirred in bath, then 4uL 1,3-propane sultone 5.5mg (about 0.045mmol) is added to system, under nitrogen protection environment, 30
Back flow reaction at DEG C.After fully reacting, removing solvent precipitates in n-hexane obtains 62mg product P1 (yield 93%).
The toxotest of amphipathic asymmetry double ion imide dye: by the above-mentioned imide dye of various concentration
P1, commercialization cell membrane dyestuff DiI with Drosophila S 2 cells instrument culture 24 hours, detect cell survival rate, under high concentration respectively
The cell survival rate cultivated together with P1 is still higher than 90%.
The dynamic monitoring of the amphipathic long-acting label cell membrane of asymmetry double ion imide dye: P1 and commercialization are contaminated
Material DiI is cultivated together with HeLa cell living, the fluorescence of both observations in 0 to 48 hours.DiI only has in 2 hours higher
Fluorescence intensity, but there are also very strong fluorescence until 48 hours by P1, showed that P1 can be used for marking cell membrane for a long time, realized that dynamic is supervised
Survey cell membrane.
The long-acting labeled insect living body intestinal cell film of amphipathic asymmetry double ion imide dye: P1 is added to fruit
After being fed three days in the food of the fly young.After the removing of drosophila enteron aisle funnel, observe that P1 is clearly marked in fluorescence imaging
Intestinal cell film.
Embodiment 2
1, by the chloro- 3,4,9,10- tetracarboxylic dianhydride 530mg (1mmol) of 1,6,7,12- tetra-, octylame 130mg (1mmol)
It is dissolved in 15ml toluene, is added in 50mL there-necked flask, take N, N- dimethyl-ethylenediamine 106mg (1.2mmol with microsyringe
About 132ul) it is added to system, system is then sealed with rubber stopper, under nitrogen protection, magnetic agitation 30min is warming up to 105
DEG C reflux.It is reacted by 12h.Reactant picks up second point after concentration, with column chromatography silica gel post separation, and eluent is with two
Chloromethanes/n-hexane (v/v=1/1).After concentration vacuum drying, 278mg product 2 (yield 39%) is obtained.
2, above-mentioned 1 46mg of product (0.05mmol) is added in polymerization pipe, adds 10ml methylene chloride, is placed in room temperature
Stirred in water bath, then 4uL 1,3-propane sultone 5.5mg (about 0.045mmol) is added to system, under nitrogen protection environment,
Back flow reaction at 30 DEG C.After fully reacting, removing solvent precipitates in n-hexane obtains 40mg product P2 (yield 93%).
Amphipathic asymmetry double ion acid imide marks cell membrane fluorescence imaging: by the imide dye of above-mentioned synthesis
P2 is cultivated 24 hours together with HeLa cell living, dyestuff can specific marker go out cell membrane, and fluorescence intensity with higher.
The present invention tetrabasic carboxylic acid two unmodified using the tetrabasic carboxylic acid dicarboxylic anhydride of island position chlorine or bromine substitution or island position
Acid anhydride is fluorescent chromophore, introduces hydrophobic alkyl chain respectively in both-end and hydrophilic double ion group obtains a kind of amphipathic asymmetric pair
Ion imide fluorescent dye.The introducing of double ion group improves the whole water-soluble and biocompatibility of structure and drops
The low cell toxicant of structure entirety.All dyestuffs are used equally in vitro and in vivo cell membrane mark fluorescent to be imaged.Due to using
Photochemical stability is good, the electrostatic for being used as fluorescent chromophore and double ion structure and membrane structure of launch wavelength near-infrared
Power effect, is greatly improved its significant notation time, the duration was up to 72 hours or more during bio-imaging.
Although above the present invention is described in detail with a general description of the specific embodiments,
On the basis of the present invention, it can be made some modifications or improvements, this will be apparent to those skilled in the art.Cause
This, these modifications or improvements, fall within the scope of the claimed invention without departing from theon the basis of the spirit of the present invention.
Claims (10)
1. amphipathic asymmetry double ion imide dye, which is characterized in that structural formula are as follows:
Wherein, R1=H, R2=Cl or Br；Or R1=R2Any one in=H, Br or Cl；M=1-5.
2. the preparation method of amphipathic asymmetric double ion imide dye described in claim 1, which is characterized in that pass through
The open loop that tertiary amino causes sultones obtains asymmetric imide derivative of the double ion group introducing with tertiary amine group
The amphipathic asymmetric double ion imide dye.
3. the preparation method of amphipathic asymmetric double ion imide dye according to claim 2, which is characterized in that
Asymmetric imide derivative and 1,3-propane sultone with tertiary amine group with molar ratio 1:1-10 in methylene chloride,
Under nitrogen protection, room temperature back flow reaction obtains amphipathic asymmetric double ion imide dye.
4. the preparation method of amphipathic asymmetric double ion imide dye according to claim 2 or 3, feature exist
In the preparation method of, the asymmetric imide derivative with tertiary amine group be tetracarboxylic dianhydride's class fluorescent core, octylame,
N, N- dimethyl-ethylenediamine are with molar ratio 1:1-5:1-5 in toluene, and under nitrogen protection, temperature rising reflux reaction obtains band uncle
The asymmetric imide derivative of amine groups.
5. the preparation method of amphipathic asymmetric double ion imide dye according to claim 4, which is characterized in that
Tetracarboxylic dianhydride's class fluorescent core is the chloro- 3,4,9,10- tetracarboxylic dianhydride of 1,7- bis- of 1,6,7,12 substitutions, 1,7-
Two bromo- 3,4,9,10- tetracarboxylic dianhydrides, the chloro- 3,4,9,10- tetracarboxylic dianhydride of 1,6,7,12- tetra-, 1,6,7,12- tetra- are bromo-
Any one or a few in 3,4,9,10- tetracarboxylic dianhydride or 1,6,7,12 unsubstituted tetracarboxylic dianhydrides.
6. the preparation method of amphipathic asymmetric double ion imide dye according to claim 2 or 3, feature exist
In the preparation method of, the asymmetric imide derivative with tertiary amine group be by tetracarboxylic dianhydride's class fluorescent core and pungent
Amine is dissolved in methanol, and under nitrogen protection, first time temperature rising reflux reacts, and concentrated, flushing and vacuum drying obtain kermesinus
After solid, with imidazoles, N, N- dimethyl-ethylenediamine, under nitrogen protection, second of temperature rising reflux reaction obtains band tertiary amine group
Asymmetric imide derivative, wherein tetracarboxylic dianhydride's class fluorescent core, octylame, N, N- dimethyl-ethylenediamine with mole
Compare 1:1-5:1-5.
7. the preparation method of amphipathic asymmetric double ion imide dye according to claim 6, which is characterized in that
Tetracarboxylic dianhydride's class fluorescent core is the chloro- 3,4,9,10- tetracarboxylic dianhydride of 1,7- bis- of 1,6,7,12 substitutions, 1,7-
Two bromo- 3,4,9,10- tetracarboxylic dianhydrides, the chloro- 3,4,9,10- tetracarboxylic dianhydride of 1,6,7,12- tetra-, 1,6,7,12- tetra- are bromo-
Any one or a few in 3,4,9,10- tetracarboxylic dianhydride or 1,6,7,12 unsubstituted tetracarboxylic dianhydrides.
8. the preparation method of amphipathic asymmetric double ion imide dye according to claim 6, which is characterized in that
The first time and second of temperature rising reflux range of reaction temperature are 85 DEG C to 120 DEG C, reaction time 10-12h.
9. amphipathic asymmetric double ion imide dye described in claim 1 is glimmering as preparation in vivo marker cell membrane
The application of light preparation.
10. amphipathic asymmetric double ion imide dye according to claim 1 is preparing membrane marker in living cells
Application in fluorescence imaging agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710013730.9A CN106800796B (en) | 2017-01-09 | 2017-01-09 | The preparation method of amphipathic asymmetry double ion imide dye and its application for marking cell membrane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710013730.9A CN106800796B (en) | 2017-01-09 | 2017-01-09 | The preparation method of amphipathic asymmetry double ion imide dye and its application for marking cell membrane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106800796A CN106800796A (en) | 2017-06-06 |
| CN106800796B true CN106800796B (en) | 2019-03-29 |
Family
ID=58985647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710013730.9A Active CN106800796B (en) | 2017-01-09 | 2017-01-09 | The preparation method of amphipathic asymmetry double ion imide dye and its application for marking cell membrane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106800796B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108558967B (en) * | 2018-03-29 | 2020-12-11 | 河南大学 | Cell membrane imaging fluorescent probe and application thereof |
| CN109517186B (en) * | 2018-11-15 | 2020-06-16 | 北京化工大学 | Three-dimensional perylene metal organic framework material capable of stabilizing anion free radicals and application method thereof for photo-thermal conversion |
| CN109369648A (en) * | 2018-12-07 | 2019-02-22 | 西南科技大学 | Water-soluble, unstressed configuration, imide dye of near infrared absorption and preparation method thereof |
| CN113755022A (en) * | 2020-06-03 | 2021-12-07 | 重庆科技学院 | Water-soluble diionic perylene bisimide dye, synthesis method and application of cell fluorescent marker |
| CN113603688B (en) * | 2021-06-23 | 2022-11-18 | 南京邮电大学 | N-type organic interface material and preparation method and application thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6166210A (en) * | 1997-12-15 | 2000-12-26 | Ciba Specialty Chemicals Corporation | Perylene imide monocarboxylic acids |
| DE10308940A1 (en) * | 2003-02-28 | 2004-09-23 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Water soluble, fluorescent perylene tetracarboxylic acid bisimide |
| DE102007007796A1 (en) * | 2007-02-16 | 2008-08-21 | Langhals, Heinz, Prof. Dr. | New perylene aldehyde, acetal or aldimine compounds, are fluorescent dyes, useful e.g. for labeling aminoacids or peptides or for pigmenting paints, lacquers or plastics |
| CN103030989B (en) * | 2012-12-10 | 2014-05-14 | 北京化工大学 | Synthesis method of water-soluble squarylium indocyanine multifunctional cell fluorescent dye |
| CN105238093B (en) * | 2015-09-02 | 2017-03-22 | 北京化工大学 | Amphiphilic indole squarylium cyanine dye and application thereof in long-acting marking of lysosome |
-
2017
- 2017-01-09 CN CN201710013730.9A patent/CN106800796B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN106800796A (en) | 2017-06-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106800796B (en) | The preparation method of amphipathic asymmetry double ion imide dye and its application for marking cell membrane | |
| Zhou et al. | Efficiently mitochondrial targeting fluorescent imaging of H2S invivo based on a conjugate-lengthened cyanine NIR fluorescent probe | |
| CN110982513B (en) | Preparation method of fluorescent carbon dots and application of fluorescent carbon dots in cell imaging | |
| CN110057804B (en) | Application of N-methyl o-phenylenediamine hydrochloride-based fluorescent carbon dots in lysosome targeting | |
| CN105524612A (en) | Isophorone fluorescence probe, and preparation method and application thereof | |
| CN108822019A (en) | Polar fluorescence probe of a kind of detection fat drips and its preparation method and application | |
| CN106243170B (en) | The synthesis and application of beta galactosidase sensor with aggregation inducing Fluorescence Increasing characteristic | |
| CN106084873B (en) | A kind of efficiently near-infrared fluorescent material and its biologic applications | |
| EP3798221A1 (en) | Fluorescent probe and preparation method and use thereof | |
| CN108794475B (en) | Alcohol-sensing fluorescent carbon dot, and preparation method and application thereof | |
| CN103896928B (en) | A kind of pH fluorescence chemical sensor and synthetic method thereof and application | |
| CN108558967B (en) | Cell membrane imaging fluorescent probe and application thereof | |
| CN108659154A (en) | The synthetic method of pH response type AIE fluorescence nano polymer quantum dots and application | |
| CN110272734A (en) | A kind of high quantum production rate carbon quantum dot preparation method and applications for NO detection | |
| CN106187880A (en) | Colored cyanines fluorescent probe based on aggregation-induced emission effect and preparation method and application | |
| CN103820104B (en) | Near infrared fluorescent probe, its method for making and the application of one class taking Nile blue as parent | |
| CN108822031A (en) | A kind of red transmitting fluorescence probe of two-photon detecting mitochondria | |
| CN105154065B (en) | A kind of fluorescent probe of quick specific recognition hydroxyl radical free radical and its preparation method and application | |
| CN110885675B (en) | Nano fluorescent probe, preparation method and application thereof in detection of HNO in Golgi apparatus | |
| CN103666458B (en) | Fluorescent probe for marking and tracking cytoplasmic membranes and preparation method of fluorescent probe | |
| CN106432312A (en) | Mitochondria target fluorescence probe, as well as preparation method and application thereof | |
| CN108997772B (en) | Mitochondria positioning near-infrared fluorescent dye THX-Np and preparation method and application thereof | |
| CN106588845A (en) | Cell autophagy monitoring probe, preparation method therefor and use of cell autophagy monitoring probe | |
| CN109913206A (en) | A kind of RNA fluorescence probe and its preparation method and application | |
| CN108699091B (en) | pH-responsive fluorescent compound, composition for detecting mitophagy using same, and method for detecting mitophagy in cell |
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 |