CN110105579B - Intracellular tracing carrier with main chain containing spiropyran as well as preparation and application thereof - Google Patents
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Abstract
The invention discloses an intracellular tracing carrier with a main chain containing spiropyran, and preparation and application thereof. The fluorescent carrier constructed by the invention can realize efficient and intelligent tracing, avoid the problems of poor photobleaching property, easy quenching and the like of fluorescent protein and organic fluorescent nanoparticles, and simultaneously solve the problem of weak fluorescence caused by poor acid-induced color change characteristics of the spiropyran on the side chain of a high polymer material.
Description
Technical Field
The invention belongs to the technical field of biology, and particularly relates to an intracellular tracing carrier with a main chain containing spiropyran, and preparation and application thereof.
Background
The Spiropyran (SP) is an organic photochromic molecule, and can be used as a molecular switch to be applied to the fields of biological imaging, photoelectric devices, chemical sensing, light-operated wettability and the like by utilizing the characteristic that the optical characteristics of the spiropyran are changed due to the change of the molecular structure before and after isomerization. Besides photochromism, spiropyrans can also reversibly switch between the two isomers of the closed ring (SP) and open ring (merocyanine, MC) under the action of different external stimuli such as pH, stress, etc. The current research on spiropyrans is almost exclusively carried out around their "photoresponse" properties. The spiropyran photoresponse is mainly generated under the excitation of ultraviolet light, and because the ultraviolet light has great damage to cells and weak penetrating power, the spiropyran photoresponse is difficult to penetrate into tissues in vivo. Therefore, this optical property of spiropyrans is not favorable for intracellular tracking. Besides photochromic characteristics, the spiropyran also shows acid-induced discoloration characteristics, namely, the spiropyran can be converted from a closed-loop structure SP to an open-loop structure MC with red fluorescence under a weak acidic condition, and the research of utilizing the acid-induced discoloration characteristics of the spiropyran for intracellular intelligent tracing mainly introduces the spiropyran into a high-molecular carrier in a branched chain form, however, the acid-induced discoloration characteristics of the spiropyran in the carrier are not sensitive, so that the intracellular tracing effect is poor.
Disclosure of Invention
The invention aims to: in order to solve the problems, the invention provides an intracellular tracing carrier with a main chain containing spiropyran, so as to solve the problem that the spiropyran shows poor acid-induced discoloration characteristics on a branched chain of a high-molecular carrier at present, and further causes poor fluorescent tracing effect.
The technical scheme adopted by the invention is as follows:
a preparation method of an intracellular tracing carrier with a main chain containing spiropyran comprises the following steps:
s1, synthesizing a spiropyran micromolecule containing a bifunctional group;
s2, synthesizing a high-molecular carrier material with a main chain containing spiropyran;
and S3, constructing a high-molecular nano-carrier with a main chain containing spiropyran and used for intracellular tracing.
The spiropyran with functional groups at two ends is introduced into the high polymer to form the amphiphilic polymer with the spiropyran structure on the main chain, and the amphiphilic polymer is applied to the research of intracellular tracing by acid-induced fluorescence generation. Compared with the spiropyran in the side chain, the acid-induced discoloration is used for intracellular tracing, and the spiropyran in the side chain is insensitive to acid, so that the spiropyran is not easy to open the ring and is changed into a fluorescent part cyanine structure.
The cross-molecular linking can more effectively transfer stress to the C-O bond, thereby initiating the mechanochromic process. Therefore, the force-induced response of the spiropyran in the polymer main chain is more obvious than that of the spiropyran in other positions, and therefore the spiropyran is introduced into the polymer main chain to obtain the nano-particle with stronger fluorescence and higher pH response sensitivity for intracellular tracing.
Further, the specific synthesis method of the step S1 is as follows: dissolving p-methoxyphenylhydrazine hydrochloride and methyl isopropyl ketone in an organic solvent, carrying out heating reflux reaction under the atmosphere of inert gas to obtain a first reaction product, dissolving the first reaction product in 20-60% aqueous hydrogen bromide, and carrying out heating reflux reaction againReacting to obtain a second reaction product, and dissolving the second reaction product in CH3In the solution I, carrying out heating reflux reaction for 6-48h under the inert gas atmosphere, adding 2, 3-dihydroxy-5-nitrobenzaldehyde and piperidine for reaction to obtain a third reaction product, dissolving the third reaction product in ethanol, and carrying out heating reflux reaction at 50-100 ℃ to obtain a spiropyran molecule containing bifunctional groups; the molar ratio of the p-methoxy phenylhydrazine hydrochloride, the methyl isopropyl ketone, the 2, 3-dihydroxy-5-nitrobenzaldehyde and the piperidine is 0.58-58:0.70-69.6: 0.66-65.53: 0.05-0.20.
Further, the organic solvent is methanol or ethanol or tetrahydrofuran, and the inert gas is nitrogen or argon.
Further, the specific synthesis method of the step S2 is as follows: and (3) mixing the bifunctional spiropyran micromolecules obtained in the step S1 with a chain extender according to the mass ratio of 15-25:1 to react to obtain poly spiropyran, and reacting with polyethylene glycol to obtain the high-molecular carrier material with the main chain containing spiropyran.
Furthermore, the chain extender is hexamethylene diisocyanate or diphenylmethane-4, 4' -diisocyanate, and the chain extender can be small molecules or macromolecules containing isocyanate and can also be small molecules or macromolecules containing carboxyl at two ends.
Further, the specific construction method of the step S3 is as follows: and (3) dissolving the high-molecular carrier material with the main chain containing the spiropyran obtained in the step S2 in an organic solvent, slowly adding the high-molecular carrier material into the medium, stirring until the organic solvent is completely volatilized, and filtering to obtain the intracellular tracing carrier with the main chain containing the spiropyran.
Further, the organic solvent is tetrahydrofuran or acetone or dichloromethane, and the medium is phosphate buffer solution or normal saline or secondary distilled water.
The intracellular tracing carrier with the main chain containing spiropyran, which is prepared by the method, is adopted.
The application of intracellular tracing carrier containing spiropyran in its main chain in intracellular tracing.
The application of the intracellular tracing carrier with the main chain containing the spiropyran is that the macromolecular nano carrier with the main chain containing the spiropyran is co-cultured with cells, and then the three-dimensional laser confocal is used for carrying out intracellular tracing on the nano particles.
In summary, due to the adoption of the technical scheme, the invention has the beneficial effects that:
1. the constructed intracellular tracing carrier with the main chain containing the spiropyran can induce the spiropyran structure to generate rapid change by utilizing the subacid environment in the cell, and further generate fluorescence for efficient tracing in the cell;
2. because the stress can be more effectively transferred to the C-O bond by a cross-molecular linking mode, the force-induced response of the spiropyran in the polymer main chain is more obvious than that of the spiropyran at other positions, and the spiropyran is introduced into the polymer main chain to obtain the nano-particles with stronger fluorescence and higher pH response sensitivity for intracellular tracing;
3. the fluorescent carrier constructed by the invention can realize efficient and intelligent tracing, avoid the problems of poor photobleaching property, easy quenching and the like of fluorescent protein and organic fluorescent nanoparticles, and simultaneously solve the problem of weak fluorescence caused by poor acid-induced color change characteristics of the spiropyran on the side chain of a high polymer material.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings needed to be used in the embodiments will be briefly described below, it should be understood that the following drawings only illustrate some embodiments of the present invention and therefore should not be considered as limiting the scope, and for those skilled in the art, other related drawings can be obtained according to the drawings without inventive efforts.
FIG. 1 is a fluorescence spectrum of an intracellular tracing carrier containing spiropyrans in its main chain at different pH values;
FIG. 2 is a laser confocal diagram of the intracellular tracer vector containing spiropyran in the main chain of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and embodiments. It should be understood that the detailed description and specific examples, while indicating the preferred embodiment of the invention, are intended for purposes of illustration only and are not intended to limit the scope of the invention. The components of embodiments of the present invention generally described and illustrated in the figures herein may be arranged and designed in a wide variety of different configurations.
Thus, the following detailed description of the embodiments of the present invention, presented in the figures, is not intended to limit the scope of the invention, as claimed, but is merely representative of selected embodiments of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments of the present invention without making any creative effort, shall fall within the protection scope of the present invention.
It is noted that relational terms such as "first" and "second," and the like, may be used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Also, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. Without further limitation, an element defined by the phrase "comprising an … …" does not exclude the presence of other identical elements in a process, method, article, or apparatus that comprises the element.
The features and properties of the present invention are described in further detail below with reference to examples.
Example 1
The preparation and application of the intracellular tracing carrier containing spiropyran in the main chain provided by the preferred embodiment of the invention comprise the following steps:
(1) dissolving 0.1g p-methoxyphenylhydrazine hydrochloride and 0.06g methyl isopropyl ketone in organic solvent methanol, heating and refluxing under nitrogen atmosphere, dissolving in 48% hydrogen bromide water solution, heating and refluxing, dissolving in 5mL CH3Heating in the solution I under nitrogen atmosphereRefluxing for 12h, adding 0.12g of 2, 3-dihydroxy-5-nitrobenzaldehyde and 5mL of piperidine, dissolving in 5mL of ethanol, and heating and refluxing at 50 ℃ to obtain a spiropyran molecule containing bifunctional groups;
(2) the method comprises the following steps of mixing dihydroxyl-containing spiropyran micromolecules with hexamethylene diisocyanate according to the mass ratio of 20: 1 reacting to obtain polyspiropyran, and reacting with polyethylene glycol (Mn being 2000g/mol) with hydroxyl at the tail end to obtain a high-molecular carrier material with a main chain containing spiropyran;
(3) dissolving a macromolecular carrier with a main chain containing spiropyran in tetrahydrofuran, slowly adding the macromolecular carrier into secondary distilled water, stirring until the solvent is completely volatilized, and filtering to obtain an intracellular tracing carrier with a main chain containing spiropyran;
(4) 1mg/mL of an intracellular tracer vector containing a spiropyran in its backbone was co-cultured with the cells.
Example 2
The preparation and application of the intracellular tracing carrier containing spiropyran in the main chain provided by the preferred embodiment of the invention comprise the following steps:
(1) dissolving 0.5g p-methoxyphenylhydrazine hydrochloride and 0.15g methyl isopropyl ketone in organic solvent methanol, heating and refluxing under nitrogen atmosphere, dissolving in 48% hydrogen bromide water solution, heating and refluxing, and dissolving in 20mL CH3Heating and refluxing the solution I for 20 hours in the nitrogen atmosphere, adding 0.8g of 2, 3-dihydroxy-5-nitrobenzaldehyde and 10mL of piperidine, dissolving in 20mL of ethanol, and heating and refluxing at 60 ℃ to obtain a spiropyran molecule containing bifunctional groups;
(2) the method comprises the following steps of mixing dihydroxyl-containing spiropyran micromolecules with hexamethylene diisocyanate according to the mass ratio of 18: 1 reacting to obtain polyspiropyran, and reacting with polyethylene glycol (Mn being 2000g/mol) with hydroxyl at the tail end to obtain a high-molecular carrier material with a main chain containing spiropyran;
(3) dissolving a macromolecular carrier with a main chain containing spiropyran in tetrahydrofuran, slowly adding the macromolecular carrier into secondary distilled water, stirring until the solvent is completely volatilized, and filtering to obtain an intracellular tracing carrier with a main chain containing spiropyran;
(4) 1.2mg/mL of an intracellular tracer vector containing a spiropyran in its backbone was co-cultured with the cells.
Example 3
The preparation and application of the intracellular tracing carrier containing spiropyran in the main chain provided by the preferred embodiment of the invention comprise the following steps:
(1) dissolving 1.5g p-methoxyphenylhydrazine hydrochloride and 0.89g methyl isopropyl ketone in organic solvent methanol, heating and refluxing under argon gas atmosphere, dissolving in 55% hydrogen bromide water solution, heating and refluxing, and dissolving in 30mL CH3Heating and refluxing the solution I for 25h under the atmosphere of argon gas, adding 1.2g of 2, 3-dihydroxy-5-nitrobenzaldehyde and 12mL of piperidine, dissolving in 30mL of ethanol, and heating and refluxing at 50 ℃ to obtain a spiropyran molecule containing bifunctional groups;
(2) the method comprises the following steps of mixing dihydroxyl-containing spiropyran micromolecules with hexamethylene diisocyanate according to the mass ratio of 23: 1 reacting to obtain polyspiropyran, and reacting with polyethylene glycol (Mn being 2000g/mol) with hydroxyl at the tail end to obtain a high-molecular carrier material with a main chain containing spiropyran;
(3) dissolving a macromolecular carrier with a main chain containing spiropyran in tetrahydrofuran, slowly adding the macromolecular carrier into secondary distilled water, stirring until the solvent is completely volatilized, and filtering to obtain an intracellular tracing carrier with a main chain containing spiropyran;
(4) 1.3mg/mL of an intracellular tracer vector containing a spiropyran in its backbone was co-cultured with the cells.
Example 4
The preparation and application of the intracellular tracing carrier containing spiropyran in the main chain provided by the preferred embodiment of the invention comprise the following steps:
(1) dissolving 5g of methoxyphenylhydrazine hydrochloride and 3.2g of methyl isopropyl ketone in an organic solvent methanol, heating and refluxing under nitrogen atmosphere, dissolving in 38% aqueous hydrogen bromide, heating and refluxing, and dissolving in 45mL of CH3Heating and refluxing the solution I for 30h in the atmosphere of nitrogen gas, adding 5.5g of 2, 3-dihydroxy-5-nitrobenzaldehyde and 12mL of piperidine, dissolving in 45mL of ethanol, and heating and refluxing at 65 ℃ to obtain a spiropyran molecule containing bifunctional groups;
(2) the method comprises the following steps of mixing dihydroxyl-containing spiropyran micromolecules with hexamethylene diisocyanate according to the mass ratio of 22: 1 reacting to obtain polyspiropyran, and reacting with polyethylene glycol (Mn being 2000g/mol) with hydroxyl at the tail end to obtain a high-molecular carrier material with a main chain containing spiropyran;
(3) dissolving a macromolecular carrier with a main chain containing spiropyran in tetrahydrofuran, slowly adding the macromolecular carrier into secondary distilled water, stirring until the solvent is completely volatilized, and filtering to obtain an intracellular tracing carrier with a main chain containing spiropyran;
(4) 1.1mg/mL of an intracellular tracer vector containing a spiropyran in its backbone was co-cultured with the cells.
Example 5
The preparation and application of the intracellular tracing carrier containing spiropyran in the main chain provided by the preferred embodiment of the invention comprise the following steps:
(1) dissolving 8g of methoxyphenylhydrazine hydrochloride and 4.3g of methyl isopropyl ketone in an organic solvent methanol, heating and refluxing under the atmosphere of nitrogen gas, dissolving in 55% aqueous hydrogen bromide, heating and refluxing, and dissolving in 80mL of CH3Heating and refluxing the solution I for 35h in the atmosphere of nitrogen gas, adding 10g of 2, 3-dihydroxy-5-nitrobenzaldehyde and 10mL of piperidine, dissolving in 80mL of ethanol, and heating and refluxing at 80 ℃ to obtain a spiropyran molecule containing bifunctional groups;
(2) the method comprises the following steps of mixing dihydroxyl-containing spiropyran micromolecules with hexamethylene diisocyanate according to a mass ratio of 19: 1 reacting to obtain polyspiropyran, and reacting with polyethylene glycol (Mn being 2000g/mol) with hydroxyl at the tail end to obtain a high-molecular carrier material with a main chain containing spiropyran;
(3) dissolving a macromolecular carrier with a main chain containing spiropyran in tetrahydrofuran, slowly adding the macromolecular carrier into secondary distilled water, stirring until the solvent is completely volatilized, and filtering to obtain an intracellular tracing carrier with a main chain containing spiropyran;
(4) 0.9mg/mL of an intracellular tracer vector containing a spiropyran in its backbone was co-cultured with the cells.
Experimental example 1
The intracellular tracing carrier with the main chain containing spiropyran obtained in examples 1-5 and cells were co-cultured for 6h, the nanoparticles were subjected to intracellular tracing by using three-dimensional laser confocal, and the fluorescence spectra of the intracellular tracing carrier with the main chain containing spiropyran at different pH values were examined, the results are shown in FIG. 1.
As can be seen from FIG. 1, as the pH is lowered, the acid-induced spiropyran structure is converted into the partial cyanine, so that an emission peak of the partial cyanine which can have red fluorescence characteristics appears at 625nm in the fluorescence spectrum, and the fact that the acid environment can induce the spiropyran structure to be converted into the partial cyanine is proved.
Experimental example 2
The intracellular tracing carrier with the main chain containing spiropyran obtained in examples 1-5 and cells were co-cultured for 6h, the nanoparticles were subjected to intracellular tracing by using three-dimensional laser confocal imaging, and the laser confocal image of the intracellular tracing carrier with the main chain containing spiropyran was examined, and the result is shown in fig. 2.
As can be seen from FIG. 2, after the nanoparticles containing spiropyran in the main chain are co-cultured with cells for a period of time, the nanoparticles enter lysosomes of the cells, and the spiropyran structure is converted into a part of cyanine due to the acidic environment in the lysosomes, so that red fluorescence is emitted for intracellular intelligent tracking.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (9)
1. A preparation method of an intracellular tracing carrier with a main chain containing spiropyran is characterized by comprising the following steps:
s1, synthesizing a spiropyran micromolecule containing a bifunctional group;
s2, synthesizing a high-molecular carrier material with a main chain containing spiropyran: mixing the bifunctional spiropyran micromolecules obtained in the step S1 with a chain extender according to the mass ratio of 15-25:1 to react to obtain poly spiropyran, and reacting with polyethylene glycol to obtain a high polymer carrier material with a main chain containing spiropyran;
s3, constructing an intracellular tracing vector with a main chain containing spiropyran.
2. The method for preparing the intracellular tracing vector containing the spiropyran in the main chain according to claim 1, wherein the specific synthetic method of the step S1 is as follows: will be p-methoxyDissolving phenylhydrazine hydrochloride and methyl isopropyl ketone in an organic solvent, carrying out heating reflux reaction under the atmosphere of inert gas to obtain a first reaction product, dissolving the first reaction product in 20-60% aqueous hydrogen bromide, carrying out heating reflux reaction again to obtain a second reaction product, and dissolving the second reaction product in CH3In the solution I, carrying out heating reflux reaction for 6-48h under the inert gas atmosphere, adding 2, 3-dihydroxy-5-nitrobenzaldehyde and piperidine for reaction to obtain a third reaction product, dissolving the third reaction product in ethanol, and carrying out heating reflux reaction at 50-100 ℃ to obtain a spiropyran molecule containing bifunctional groups; the molar ratio of the p-methoxy phenylhydrazine hydrochloride, the methyl isopropyl ketone, the 2, 3-dihydroxy-5-nitrobenzaldehyde and the piperidine is 0.58-58:0.70-69.6: 0.66-65.53: 0.05-0.20.
3. The method for preparing an intracellular tracing vector containing spiropyran in the main chain according to claim 2, characterized in that: the organic solvent is methanol or ethanol or tetrahydrofuran, and the inert gas is nitrogen or argon.
4. The method for preparing the intracellular tracer vector containing the spiropyran in the main chain according to claim 1, wherein the chain extender is hexamethylene diisocyanate or diphenylmethane-4, 4' -diisocyanate.
5. The method for preparing the intracellular tracing vector containing the spiropyran in the main chain according to claim 1, wherein the specific construction method of the step S3 is as follows: and (3) dissolving the high-molecular carrier material with the main chain containing the spiropyran obtained in the step S2 in an organic solvent, slowly adding the high-molecular carrier material into the medium, stirring until the organic solvent is completely volatilized, and filtering to obtain the intracellular tracing carrier with the main chain containing the spiropyran.
6. The method for preparing an intracellular tracing vector containing spiropyran in the main chain according to claim 5, characterized in that: the organic solvent is tetrahydrofuran or acetone or dichloromethane, and the medium is phosphate buffer solution or normal saline or secondary distilled water.
7. An intracellular tracer vector having a spiropyran-containing backbone prepared by the method of any one of claims 1 to 6.
8. Use of an intracellular tracing vector containing a spiropyran as a main chain according to claim 7 for intracellular tracing.
9. Use of an intracellular tracer vector having a spiropyran backbone according to claim 8, wherein: coculturing an intracellular tracing carrier with a main chain containing spiropyran and cells, and performing intracellular tracing on the nanoparticles by using three-dimensional laser confocal technology.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1227447B (en) * | 1962-03-30 | 1966-10-27 | Chinoin Gyogyszer Es Vegyeszet | Process for the preparation of phenylisopropylamines |
| CN107236105A (en) * | 2017-05-31 | 2017-10-10 | 浙江工业大学之江学院 | A kind of urethane composition with mechanical response characteristic and preparation method thereof |
| CN108383963A (en) * | 2018-03-22 | 2018-08-10 | 广东工业大学 | A kind of composition and preparation method thereof and the application in power mutagens color Material Field |
| CN108559053A (en) * | 2018-04-24 | 2018-09-21 | 四川大学 | The preparation method of photochromic luminous polyurethane based on long after glow luminous material and spiro-pyrans |
-
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1227447B (en) * | 1962-03-30 | 1966-10-27 | Chinoin Gyogyszer Es Vegyeszet | Process for the preparation of phenylisopropylamines |
| CN107236105A (en) * | 2017-05-31 | 2017-10-10 | 浙江工业大学之江学院 | A kind of urethane composition with mechanical response characteristic and preparation method thereof |
| CN108383963A (en) * | 2018-03-22 | 2018-08-10 | 广东工业大学 | A kind of composition and preparation method thereof and the application in power mutagens color Material Field |
| CN108559053A (en) * | 2018-04-24 | 2018-09-21 | 四川大学 | The preparation method of photochromic luminous polyurethane based on long after glow luminous material and spiro-pyrans |
Non-Patent Citations (1)
| Title |
|---|
| "含不同基团螺吡喃化合物的合成及其光谱性能研究";王希峰;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20160815(第8期);B014-156 * |
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