CN106800796A - The application of the preparation method and its mark cell membrane of amphipathic asymmetric Shuan Li perylene diimide dyestuffs - Google Patents
The application of the preparation method and its mark cell membrane of amphipathic asymmetric Shuan Li perylene diimide dyestuffs Download PDFInfo
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- 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
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Abstract
Application the invention discloses amphipathic asymmetric Shuan Li perylene diimide dyestuffs for belonging to biomarker technical field technical field and preparation method thereof and in terms of active somatic cell membrane marker fluorescence imaging.The present invention replaces perylene tetracarboxylic acids dicarboxylic anhydride or the unmodified perylenetetracarboxylic dianhydrides in island position to be fluorescent chromophore using island position chlorine or bromine, introduces hydrophobic alkyl chain respectively in both-end and hydrophilic double ion group obtains the amphipathic asymmetric Shuan Li perylene diimide fluorescent dyes of a class.The introducing of double ion group improves the overall water-soluble and biocompatibility of structure and reduces the overall cell toxicant of structure.All dyestuffs are used equally to the imaging of in vitro and in vivo cell membrane mark fluorescent.It is good as a result of photochemical stability, launch wavelength near-infrared perylenes are used as fluorescent chromophore, and double ion structure and the electrostatic force of membrane structure, its significant notation time is greatly improved during biological living cell membrane imaging, the duration was up to more than 72 hours.
Description
Technical field
The invention belongs to biomarker technical field, contaminated in particular to amphipathic asymmetric Shuan Li perylene diimides
Material and preparation method thereof and the application in terms of active somatic cell membrane marker fluorescence imaging.
Background technology
In biological and medical research field, bioluminescence imaging is high, right due to its detecting instrument mature, sensitivity
The advantages of than spending high, high resolution, imaging directly perceived, fast image taking speed and lossless detection, is wide at the aspect such as physiology and pathological study
General application.Bioluminescence imaging relies on the development of optical molecular probe, especially nontoxic, and the function of biology, long-acting work are not influenceed
Luminescent dye molecule.One intuitively, clearly static or dynamic image can be used to analyze cell or organism is special
Determine feature, the state in region, in addition specific molecular the information such as expression, distribution.And wherein cell membrane is to prevent ECM
The barrier of cell is freely accessible to, it ensure that stablizing relatively for intracellular environment, enable various biochemical reaction orderly functions.Together
When cell information, material must occur with surrounding environment and be exchanged with energy, specific physiological function could be completed.Therefore develop
One class marks cell membrane, and effect stability, long-acting dynamic monitoring are particularly significant to life science.
In numerous fluorescence organic compounds, perylene and its derivative have good light, heat, chemical stability, fluorescence volume
Sub- yield is high, and fluorescence emission peak is narrow and launch wavelength can effectively avoid the ambient interferences 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 that a kind of stabilizability is good, mark is acted on
Between specific marker fluorescent dye that is longer and being capable of dynamic monitoring cell membrane it is significant.
The content of the invention
It is an object of the invention to provide a class light, heat endurance be good, water-soluble good, structure it is programmable it is amphipathic not
Symmetrical double ion perylene diimide dyestuff and preparation method thereof, such dyestuff can be used for active somatic cell membrane marker, and can realize it is right
Living cells film long-time dynamic monitoring.
The technical scheme is that：Use light, good heat stability perylene classes chromophore, fatty amine, N, N- dimethyl
Ethylenediamine is raw material, one-step method prepare it is asymmetric continue functionalization perylene diimide derivatives, then by tertiary amino
Trigger the open loop of sultones that double ion group further is introduced into dye molecule.The introducing of double ion group both increased structure
Water solubility, and there is provided the polar group that can be combined with film surface, and double ion group has electrolyte higher
Buffer capacity and low cytotoxicity, this all improves dyestuff action time in the cell.Because rational design is balanced
The hydrophobic and hydrophilic segment of perylene diimide dye structure, dye molecule can in aqueous be assembled into particle diameter 100-200nm's
Contain the vesica of negative ions in surface.This vesica can enter cell by endocytosis, lysosomal acid in the cell
After the system of solutions dresses up unimolecule under interior environment, intracellular membrane structure is incorporated, so as to mark intracellular membrane structure.In living insects
Under sour environment in enteron aisle, this vesica system of solutions dresses up unimolecule, so as to directly mark live body enterocyte plasma membrane.
Amphipathic asymmetric Shuan Li perylene diimide Dyes structural formulaes of the present invention are：
Wherein, R1=H, R2=Cl or Br；Or R1=R2Any one in=H, Br or Cl；M=1-5.
The preparation method of above-mentioned amphipathic asymmetric Shuan Li perylene diimide dyestuffs is：Sultones is triggered by tertiary amino
Open loop by double ion group introducing the Bu Dui Cheng perylene diimide derivatives with tertiary amine group obtain amphipathic asymmetric double ion
Perylene diimide dyestuff.
Further, the Bu Dui Cheng perylene diimides derivatives with tertiary amine group and PS are with mol ratio 1：1-
10 in dichloromethane, and under nitrogen protection, room temperature back flow reaction obtains amphipathic asymmetric Shuan Li perylene diimide dyestuffs.
Further, the preparation method of the Bu Dui perylene diimide derivatives with tertiary amine group is called perylene tetracarboxylic acid two
Anhydride fluorescent core and octylame are dissolved in methyl alcohol, under nitrogen protection, first time temperature rising reflux reaction, it is concentrated, rinse and vacuum
Dry, after obtaining dark red solid, with imidazoles, N, N- dimethyl-ethylenediamine, under nitrogen protection, second temperature rising reflux is anti-
Should, obtain the Bu Dui Cheng perylene diimide derivatives with tertiary amine group, wherein , perylenetetracarboxylic dianhydrides class fluorescent core, octylame, N, N- bis-
Methyl ethylenediamine is with mol ratio 1：1-5：1-5.
Preferably, it is 1, the 7- bis- chloro- 3 of island position substitution, 4,9,10- perylene tetracarboxylic acids to state perylenetetracarboxylic dianhydride's class fluorescent core
The bromo- 3,4,9,10- perylenetetracarboxylic dianhydrides of acid dianhydride, 1,7- bis-, the chloro- 3,4,9,10- perylenetetracarboxylic dianhydrides of 1,6,7,12- tetra-, 1,
In the bromo- 3,4,9,10- perylenetetracarboxylic dianhydrides of 6,7,12- tetra- or the perylenetetracarboxylic dianhydride that does not replace of 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。
Interchangeable, the preparation method of the Bu Dui perylene diimide derivatives with tertiary amine group is called perylenetetracarboxylic dianhydride
Class fluorescent core, octylame, N, N- dimethyl-ethylenediamines are with mol ratio 1：1-5：1-5 in toluene, under nitrogen protection, temperature rising reflux
Reaction, obtains the Bu Dui Cheng perylene diimide derivatives with tertiary amine group.
Preferably, it is 1, the 7- bis- chloro- 3 of island position substitution, 4,9,10- perylene tetracarboxylic acids to state perylenetetracarboxylic dianhydride's class fluorescent core
The bromo- 3,4,9,10- perylenetetracarboxylic dianhydrides of acid dianhydride, 1,7- bis-, the chloro- 3,4,9,10- perylenetetracarboxylic dianhydrides of 1,6,7,12- tetra-, 1,
In the bromo- 3,4,9,10- perylenetetracarboxylic dianhydrides of 6,7,12- tetra- or the perylenetetracarboxylic dianhydride that does not replace of 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, and the reaction time is 10-12h.
Above-mentioned amphipathic asymmetric Shuan Li perylene diimides dyestuff is used in vivo marker cell membrane fluorescence imaging.
The application that above-mentioned amphipathic asymmetric Shuan Li perylene diimides dyestuff is imaged in living cells inner membrance mark fluorescent.
The present invention has following Advantageous Effects：
1st, the present invention provide it is amphipathic asymmetric double can be with from sub- perylene diimide dye UV absorbance and fluorescent emission
The interference of AF background in bio-imaging is prevented effectively from, signal to noise ratio is improved.
2nd, the amphipathic asymmetric Shuan Li perylene diimides dyestuff that the present invention is provided has water solubility, introduces potential resistance to electrolyte contamination
The strong double ion group of buffer capacity and with relatively low bio-toxicity.
3rd, the amphipathic asymmetric Shuan Li perylene diimide dyestuffs that the present invention is provided, due to using light, good heat stability
Perylene do fluorescent chromophore, thus living cells inner membrance can be marked with long-time stable, the mark duration was up to more than 72 hours.
4th, the amphipathic asymmetric Shuan Li perylene diimides dyestuff design that the present invention is provided is simple, and synthesis is convenient, raw material warp
Ji, structure good light stability, toxicity is low, and the cell membrane of biological tissue can be marked by simple mode, is that a class is new
The long-time specific marker active somatic cell film dyestuff of type.
Brief description of the drawings
The fluorescent chromophore used in Fig. 1 present invention.
The reacting flow chart of the asymmetric Shuan Li perylene diimides dyestuff of Fig. 2 synthesizing amphipathics.
The nucleus magnetic hydrogen spectrum of product is characterized in Fig. 3 embodiments 1.
The nuclear-magnetism carbon stave of product is levied in Fig. 4 embodiments 1.
The mass spectral characteristi of product in Fig. 5 embodiments 1.
Fig. 6 is the spectrum property of amphipathic Dui Cheng perylene diimide dyestuffs P1 in embodiment 1.
Fig. 7 is the confocal fluorescent imaging of P1 mark HeLa cell membranes in embodiment 1.
Fig. 8 is the confocal fluorescent imaging of P1 marks insect live body gut plasma membrane living in embodiment 1.
Fig. 9 is the cytotoxicity test of P1 in embodiment 1.
The schematic diagram that the amphipathic asymmetric Shuan Li perylene diimides of Figure 10 are combined with cell membrane.
Specific embodiment
Following examples are used to illustrate the present invention, but are not limited to the scope of the present invention.If not specializing, embodiment
In raw materials used be commercial goods.
Embodiment 1
1st, by 3,4,9,10- perylenetetracarboxylic dianhydride 527mg (1mmol), octylame 130mg (1mmol) are dissolved in 15ml methyl alcohol,
It is added in 50mL there-necked flasks, then uses rubber stopper seal system, under nitrogen protection, magnetic agitation 30min is warmed up to 85 DEG C
Backflow.Reacted by 12h.Reactant with alcohol flushing by after concentration, being precipitated.After concentration vacuum drying, obtain dark red
Color solid.
Above-mentioned dark red solid, imidazoles 10g, N, N- dimethyl-ethylenediamine 106mg (1.2mmol about 132ul) are added to
In there-necked flask, rubber stopper seal system then is used, under nitrogen protection, be warmed up to 120 DEG C of back flow reactions.Reacted by 12h.Instead
Thing is answered by after concentration, being filtrated to get precipitation, with substantial amounts of water washing after, access second point with column chromatography silica gel post separation,
Eluent chloroform.After concentration vacuum drying, 218mg products 1 (yield 26%) are obtained.
2nd, by the 57mg of above-mentioned product 1 (0.1mmol) addition polymerization pipe, 10ml dichloromethane is added, is placed in room temperature water
Stirred in bath, then 4uL PSs 5.5mg (about 0.045mmol) is added to system, under nitrogen environmental protection, 30
Back flow reaction at DEG C.After reaction completely, removing solvent is precipitated in n-hexane and obtains 62mg products P1 (yield 93%).
The toxotest of amphipathic asymmetric Shuan Li perylene diimide dyestuffs：By the Shang Shu perylene diimide dyestuffs of various concentrations
P1, commercialization cell membrane dyestuff DiI respectively with Drosophila S 2 cells instrument culture 24 hours, cell survival rate is detected, under high concentration
The cell survival rate cultivated together with P1 remains above 90%.
The dynamic monitoring of the amphipathic long-acting mark cell membrane of asymmetric Shuan Li perylene diimide dyestuffs：P1 is contaminated with commercialization
Material DiI is cultivated together with HeLa cells living, and the fluorescence of the two was observed in 0 to 48 hours.DiI only had higher in 2 hours
Fluorescence intensity, but P1 also had very strong fluorescence until 48 hours, showed that P1 can be used to mark cell membrane for a long time, realized dynamic prison
Survey cell membrane.
The amphipathic long-acting labeled insect live body intestinal cell film of asymmetric Shuan Li perylene diimide dyestuffs：P1 is added to fruit
After being fed three days in the food of the fly young.Observe that P1 is clearly marked after fruit bat enteron aisle funnel is peeled off, in fluorescence imaging
Intestinal cell film.
Embodiment 2
1st, by the chloro- 3,4,9,10- perylenetetracarboxylic dianhydrides 530mg (1mmol) of 1,6,7,12- tetra-, octylame 130mg (1mmol)
It is dissolved in 15ml toluene, is added in 50mL there-necked flasks, N, N- dimethyl-ethylenediamine 106mg (1.2mmol is taken with microsyringe
About 132ul) system is added to, rubber stopper seal system then is used, under nitrogen protection, magnetic agitation 30min is warmed up to 105
DEG C backflow.Reacted by 12h.By after concentration, second point being accessed with column chromatography silica gel post separation, eluent uses two to reactant
Chloromethanes/n-hexane (v/v=1/1).After concentration vacuum drying, 278mg products 2 (yield 39%) are obtained.
2nd, by the 46mg of above-mentioned product 1 (0.05mmol) addition polymerization pipe, 10ml dichloromethane is added, is placed in room temperature
Stirred in water bath, then 4uL PSs 5.5mg (about 0.045mmol) is added to system, under nitrogen environmental protection,
Back flow reaction at 30 DEG C.After reaction completely, removing solvent is precipitated in n-hexane and obtains 40mg products P2 (yield 93%).
Amphipathic asymmetric Shuan Li perylene diimides mark cell membrane fluorescence imaging：By above-mentioned synthesis perylene diimide dyestuffs
P2 is cultivated 24 hours together with HeLa cells living, dyestuff can specific marker go out cell membrane, and with fluorescence intensity higher.
The present invention replaces the unmodified perylene tetracarboxylic acids two of perylene tetracarboxylic acids dicarboxylic anhydride or island position using island position chlorine or bromine
Acid anhydride is fluorescent chromophore, introduces hydrophobic alkyl chain respectively in both-end and hydrophilic double ion group obtains amphipathic asymmetric pair an of class
Li perylene diimide fluorescent dyes.The introducing of double ion group improves the overall water-soluble and biocompatibility of structure and drops
The overall cell toxicant of low structure.All dyestuffs are used equally to the imaging of in vitro and in vivo cell membrane mark fluorescent.As a result of
Photochemical stability is good, launch wavelength near-infrared perylenes as fluorescent chromophore, and double ion structure and membrane structure electrostatic
Power is acted on, and its significant notation time is greatly improved during bio-imaging, and the duration was up to more than 72 hours.
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, belong to the scope of protection of present invention without departing from theon the basis of the spirit of the present invention.
Claims (10)
1. amphipathic asymmetric Shuan Li perylene diimide dyestuffs, it is characterised in that structural formula is：
Wherein, R1=H, R2=Cl or Br；Or R1=R2Any one in=H, Br or Cl；M=1-5.
2. the preparation method of the amphipathic asymmetric Shuan Li perylene diimide dyestuffs described in claim 1, it is characterised in that pass through
Tertiary amino triggers the open loop of sultones to obtain double ion group Bu Dui Cheng perylene diimide derivative of the introducing with tertiary amine group
The amphipathic asymmetric Shuan Li perylene diimide dyestuffs.
3. the preparation method of amphipathic asymmetric Shuan Li perylene diimide dyestuffs according to claim 2, it is characterised in that
Bu Dui Cheng perylene diimides derivatives with tertiary amine group are with 1,3- propane sultones with mol ratio 1：1-10 in dichloromethane,
Under nitrogen protection, room temperature back flow reaction obtains amphipathic asymmetric Shuan Li perylene diimide dyestuffs.
4. the preparation method of the amphipathic asymmetric Shuan Li perylene diimide dyestuffs according to Claims 2 or 3, its feature exists
In the preparation method of, Bu Dui perylene diimide derivatives with tertiary amine group be called perylenetetracarboxylic dianhydride's class fluorescent core, octylame,
N, N- dimethyl-ethylenediamine are with mol ratio 1：1-5：In toluene, under nitrogen protection, temperature rising reflux reaction obtains band uncle to 1-5
The Bu Dui Cheng perylene diimide derivatives of amine groups.
5. the preparation method of amphipathic asymmetric Shuan Li perylene diimide dyestuffs according to claim 4, it is characterised in that
Stated perylenetetracarboxylic dianhydride's class fluorescent core is the chloro- 3,4,9,10- perylenetetracarboxylic dianhydrides of 1,7- bis-, the 1,7- bis- of island position substitution
Bromo- 3,4,9,10- perylenetetracarboxylic dianhydrides, the chloro- 3,4,9,10- perylenetetracarboxylic dianhydrides of 1,6,7,12- tetra-, 1,6,7,12- tetra- bromo- 3,
4,9,10- perylenetetracarboxylic dianhydrides or island position do not replace any one or a few in perylenetetracarboxylic dianhydrides.
6. the preparation method of the amphipathic asymmetric Shuan Li perylene diimide dyestuffs according to Claims 2 or 3, its feature exists
It is called perylenetetracarboxylic dianhydride's class fluorescent core and pungent in the preparation method of, Bu Dui perylene diimide derivatives with tertiary amine group
Amine is dissolved in methyl alcohol, under nitrogen protection, first time temperature rising reflux reaction, it is concentrated, rinse and be vacuum dried, obtain kermesinus
After solid, with imidazoles, N, N- dimethyl-ethylenediamine, under nitrogen protection, second temperature rising reflux reaction obtains band tertiary amine group
Bu Dui Cheng perylene diimide derivatives, wherein , perylenetetracarboxylic dianhydrides class fluorescent core, octylame, N, N- dimethyl-ethylenediamines with mole
Than 1：1-5：1-5.
7. the preparation method of amphipathic asymmetric Shuan Li perylene diimide dyestuffs according to claim 6, it is characterised in that
Stated perylenetetracarboxylic dianhydride's class fluorescent core is the chloro- 3,4,9,10- perylenetetracarboxylic dianhydrides of 1,7- bis-, the 1,7- bis- of island position substitution
Bromo- 3,4,9,10- perylenetetracarboxylic dianhydrides, the chloro- 3,4,9,10- perylenetetracarboxylic dianhydrides of 1,6,7,12- tetra-, 1,6,7,12- tetra- bromo- 3,
4,9,10- perylenetetracarboxylic dianhydrides or island position do not replace any one or a few in perylenetetracarboxylic dianhydrides.
8. the preparation method of amphipathic asymmetric Shuan Li perylene diimide dyestuffs according to claim 6, it is characterised in that
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.
9. by the amphipathic asymmetric Shuan Li perylene diimides dyestuff described in claim 1 be used in vivo marker cell membrane fluorescence into
Picture.
10. amphipathic asymmetric Shuan Li perylene diimides dyestuff according to claim 1 is in living cells inner membrance mark fluorescent
The application of imaging.
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| CN108558967A (en) * | 2018-03-29 | 2018-09-21 | 河南大学 | A kind of cell membrane imaging fluorescence probe and its application |
| 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 |
| CN109517186A (en) * | 2018-11-15 | 2019-03-26 | 北京化工大学 | A kind of three-dimensional metalloid organic framework material that can stablize radical anion and its application method for photothermal conversion |
| CN113603688A (en) * | 2021-06-23 | 2021-11-05 | 南京邮电大学 | N-type organic interface material and preparation method and application 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 |
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| 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 |
| CN113603688A (en) * | 2021-06-23 | 2021-11-05 | 南京邮电大学 | N-type organic interface material and preparation method and application thereof |
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