CN114748619A - Aggregation-induced luminescent material and preparation method and application thereof - Google Patents
Aggregation-induced luminescent material and preparation method and application thereof Download PDFInfo
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- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
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- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
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- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
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Abstract
The aggregation-induced luminescent material comprises a metabolic group and an aggregation-induced luminescent group which are connected by adopting a chemical bond, wherein the metabolic group comprises a D-alanine derivative containing a first unsaturated bond, and the aggregation-induced luminescent group comprises a 4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide derivative containing a second unsaturated bond, so that the bacteria can be rapidly marked and cleared in situ, and the aggregation-induced luminescent material has the characteristics of rapidness in detection, broad-spectrum antibiosis, reduction of drug resistance and the like, and has a wide application prospect in clinical treatment of bacteria, particularly drug-resistant bacteria.
Description
Technical Field
The application belongs to the technical field of material synthesis, and particularly relates to an aggregation-induced emission material, and a preparation method and application thereof.
Background
Before penicillin was discovered, the number of people who died from infection with pathogenic bacteria was rare. In 1928, the british scientist Fleming discovered penicillin the earliest in experimental studies, and penicillin in 1943 realized mass production, which brought eosin to the treatment of infectious diseases. With the discovery and mass production of more antibiotics such as streptomycin, vancomycin and the like, the phenomenon of antibiotic abuse is increasingly serious, and the long-term, wide and excessive clinical antibiotic abuse causes the emergence of drug-resistant bacterial strains and multiple drug-resistant bacterial strains (super bacteria). According to statistics, the nosocomial infection rate of the multi-drug-resistant strain reaches 8%. The nosocomial drug-resistant bacterial infection is mostly a group with weak resistance, and the Intensive Care Unit (ICU) multiple drug-resistant bacterial infection is the biggest death threat of patients. Once such a population is infected with drug-resistant bacteria, the prognosis of the treatment is not optimistic. The emergence of multi-drug resistant strains brings great challenges to the traditional antibiotic treatment method, and the development of a broad-spectrum antibacterial agent or preparation which is not easy to induce multi-drug resistance of bacteria is urgently needed for killing clinical pathogenic bacteria (especially multi-drug resistant bacteria) and treating bacterial infection.
Disclosure of Invention
The application aims to provide an aggregation-induced emission material, a preparation method and an application thereof, and aims to solve the problem that the material in the prior art cannot rapidly mark and sterilize bacteria.
In order to achieve the purpose of the application, the technical scheme adopted by the application is as follows:
in a first aspect, the present application provides an aggregation-inducing luminescent material comprising a metabolic group and an aggregation-inducing luminescent group, wherein the metabolic group comprises a D-alanine derivative having a first unsaturated bond, and the aggregation-inducing luminescent group comprises a 4- (2- (4-benzhydrylamine-phenylethene) -pyridinium bromide derivative having a second unsaturated bond, and the metabolic group and the aggregation-inducing luminescent group are connected by a chemical bond.
In a second aspect, the present application provides a method for preparing an aggregation-induced emission material, comprising the steps of:
providing a D-alanine derivative having a first unsaturated bond and a 4- (2- (4-benzhydrylamine phenylethene) pyridinium bromide derivative having a second unsaturated bond;
and mixing the D-alanine derivative containing the first unsaturated bond and the 4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide derivative containing the second unsaturated bond, and carrying out click chemical reaction to obtain the aggregation-induced luminescent material.
In a third aspect, the present application provides a use of aggregation-inducing luminescent material for marking and killing bacteria, wherein the bacteria comprise at least one of gram-positive and gram-negative bacteria whose cell walls contain peptidoglycan components.
In a fourth aspect, the present application provides a sterilization method using aggregation-induced emission materials, the sterilization method comprising the steps of:
providing a sample to be sterilized, and carrying out sterilization,
mixing a sample to be sterilized with an aggregation-induced emission material, and incubating to obtain a blending solution;
and carrying out laser irradiation treatment on the blended liquid to obtain a sterilized sample.
According to the aggregation-induced emission material provided by the first aspect of the application, the aggregation-induced emission material comprises a metabolic group and an aggregation-induced emission group which are connected by adopting a chemical bond, wherein the provided metabolic group comprises a D-alanine derivative containing a first unsaturated bond, and the D-alanine derivative can be specifically combined and aggregated on a large number of bacterial cell walls, so that the bacteria can be subjected to quasi-positioning and efficient marking; the aggregation-induced luminescent group comprises a 4- (2- (4-benzhydrylamine phenylethene) pyridine bromide derivative containing a second unsaturated bond, is positioned and marked by a metabolic group and then is subjected to laser irradiation treatment, so that the aggregation-induced luminescent group generates an active oxygen group through the laser irradiation treatment, the positioned bacteria are subjected to photodynamic killing, the metabolic group and the aggregation-induced luminescent group are subjected to addition reaction through the contained unsaturated bond and are connected with a chemical bond, and the metabolic group and the aggregation-induced luminescent group are tightly connected, so that the bacteria can be quickly marked and removed in situ.
The second aspect of the present application provides a method for preparing an aggregation-induced emission material, which is simple and easy to operate, and the aggregation-induced emission material can be obtained by mixing the provided D-alanine derivative containing the first unsaturated bond and the 4- (2- (4-benzhydrylamine-phenylethene) pyridine bromide salt derivative containing the second unsaturated bond and then performing a click chemical reaction.
The aggregation-induced emission material provided by the third aspect of the application is applied to marking and killing bacteria, and because the metabolic groups included in the aggregation-induced emission material can mark at least one of gram-positive bacteria and gram-negative bacteria of which the cell walls contain peptidoglycan components, the aggregation-induced emission material can realize in-situ removal of the bacteria, and has high detection speed and good application effect.
The fourth aspect of the present application provides a sterilization method using aggregation-induced emission material, the sterilization method using aggregation-induced emission material and bacteria for co-incubation, so that metabolic groups participate in the synthesis process of bacteria by synthesizing cell wall peptidoglycan to specifically label bacteria; then, the aggregation-induced emission groups are induced by laser irradiation treatment to form active oxygen groups to sterilize bacteria, so that rapid, efficient and fixed-point sterilization treatment is realized.
Drawings
In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings needed to be used in the embodiments or the prior art descriptions will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present application, and it is obvious for those skilled in the art to obtain other drawings without creative efforts.
Fig. 1 is a graph showing the AIE effect of the aggregation-induced emission material provided in the embodiment of the present application.
FIG. 2 is a graph showing the effect of aggregation-inducing luminescent materials on labeling bacteria according to the examples of the present application.
FIG. 3 is a graph showing the results of the generation efficiency of active oxygen by the aggregation-induced emission metabolism material provided in the examples of the present application.
FIG. 4 is a graph showing the effect of aggregation-induced emission metabolism materials on the photodynamic killing of bacteria, provided in examples of the present application.
Detailed Description
In order to make the technical problems, technical solutions and beneficial effects to be solved by the present application more clearly apparent, the present application is further described in detail below with reference to the embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the present application and are not intended to limit the present application.
In this application, the term "and/or" describes an association relationship of associated objects, meaning that there may be three relationships, e.g., a and/or B, which may mean: a is present alone, A and B are present simultaneously, and B is present alone. Wherein A and B can be singular or plural. The character "/" generally indicates that the former and latter associated objects are in an "or" relationship.
In the present application, "at least one" means one or more, "a plurality" means two or more. "at least one of the following" or similar expressions refer to any combination of these items, including any combination of the singular or plural items. For example, "at least one (a), b, or c", or "at least one (a), b, and c", may each represent: a, b, c, a-b (i.e. a and b), a-c, b-c, or a-b-c, wherein a, b, and c can be single or multiple respectively.
It should be understood that, in various embodiments of the present application, the sequence numbers of the above-mentioned processes do not mean the execution sequence, some or all of the steps may be executed in parallel or executed sequentially, and the execution sequence of each process should be determined by its function and inherent logic, and should not constitute any limitation to the implementation process of the embodiments of the present application.
The terminology used in the embodiments of the present application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. As used in the examples of this application and the appended claims, the singular forms "a", "an", and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.
The weight of the related components mentioned in the description of the embodiments of the present application may not only refer to the specific content of each component, but also represent the proportional relationship of the weight among the components, and therefore, the content of the related components is scaled up or down within the scope disclosed in the description of the embodiments of the present application as long as it is scaled up or down according to the description of the embodiments of the present application. Specifically, the mass in the description of the embodiments of the present application may be a mass unit known in the chemical field such as μ g, mg, g, kg, etc.
The terms "first" and "second" are used for descriptive purposes only and are used for distinguishing purposes such as substances from one another, and are not to be construed as indicating or implying relative importance or implying any number of technical features indicated. For example, a first XX may also be referred to as a second XX, and similarly, a second XX may also be referred to as a first XX, without departing from the scope of embodiments of the present application. Thus, a feature defined as "first" or "second" may explicitly or implicitly include one or more of that feature.
In a first aspect, the present embodiments provide an aggregation-induced emission material including a metabolic group and an aggregation-induced emission group, wherein the metabolic group includes a D-alanine derivative having a first unsaturated bond, and the aggregation-induced emission group includes a 4- (2- (4-benzhydrylamine-phenylethene) -pyridinium bromide derivative having a second unsaturated bond.
According to the aggregation-induced emission material provided by the first aspect of the embodiment of the application, the aggregation-induced emission material comprises a metabolic group and an aggregation-induced emission group which are connected by adopting a chemical bond, wherein the provided metabolic group comprises a D-alanine derivative containing a first unsaturated bond, and the D-alanine derivative can be specifically combined and aggregated on a large number of bacterial cell walls, so that the bacteria can be accurately positioned and efficiently marked; the aggregation-induced luminescent group comprises a 4- (2- (4-benzhydrylamine phenylethene) pyridine bromide derivative containing a second unsaturated bond, is positioned and marked by a metabolic group and then is subjected to laser irradiation treatment, so that the aggregation-induced luminescent group generates an active oxygen group through the laser irradiation treatment, the positioned bacteria are subjected to photodynamic killing, the metabolic group and the aggregation-induced luminescent group are subjected to addition reaction through the contained unsaturated bond and are connected with a chemical bond, and the metabolic group and the aggregation-induced luminescent group are tightly connected, so that the bacteria can be quickly marked and removed in situ.
In some embodiments, the metabolic group is chemically linked to the aggregation-inducing luminescent group to form the aggregation-inducing luminescent material.
In some embodiments, the metabolic group is a D-alanine derivative having a first unsaturated bond, wherein the first unsaturated bond comprises an unsaturated bond containing a nitrogen atom. In some embodiments, the D-alanine derivative having the first unsaturated bond comprises any one of azide, tetrazine, thiol, alkyne, trans-cyclooctene, or alkene-modified D-alanine. The D-alanine contained in the provided metabolic group is a synthetic raw material of bacterial cell wall peptidoglycan, can participate in the synthesis of the cell wall, realizes the rapid and accurate positioning of the bacteria by participating in the synthesis of the cell wall of the bacteria, and is beneficial to killing the bacteria subsequently. In some embodiments, the 4- (2- (4-benzhydrylamine phenylethylene) pyridinium bromide derivative containing the unsaturated bond comprises any one of alkyne, trans-cyclooctene, alkene, azide, tetrazine or sulfydryl modified 4- (2- (4-benzhydrylamine phenylethylene) pyridinium bromide, and the aggregation-inducing luminescent group provided can generate active oxygen groups to kill bacteria in a photodynamic way under the irradiation of laser light, and finally realizes the rapid marking and in-situ removal of the bacteria.
In some embodiments, the metabolic group is 3-tetrazine-D-alanine and the aggregation-inducing luminescent group is 1-trans-cyclooctene-4- (2- (4-benzhydrylamine phenylethene) pyridinium bromide.
In some embodiments, the wavelength of the excitation light of the aggregation-induced emission material is 250 to 500 nm; the characteristic fluorescence emission spectrum is 500-900 nm. In some embodiments, the excitation light wavelength of the aggregation-inducing luminescent material includes, but is not limited to, 250nm, 300nm, 350nm, 400nm, 450nm, 500 nm; characteristic fluorescence emission spectra include, but are not limited to, 500nm, 550nm, 600nm, 650nm, 700nm, 750nm, 800nm, 850nm, 900 nm.
A second aspect of the embodiments of the present application provides a method for preparing an aggregation-induced emission material, including the following steps:
s01, providing a D-alanine derivative containing a first unsaturated bond and a 4- (2- (4-benzhydrylamine phenylethene) pyridinium bromide derivative containing a second unsaturated bond;
s02, mixing the D-alanine derivative containing the first unsaturated bond and the 4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide derivative containing the second unsaturated bond, and carrying out click chemical reaction to obtain the aggregation-induced emission material.
The second aspect of the embodiment of the present application provides a method for preparing an aggregation-induced emission material, which is simple and easy to operate, and the provided D-alanine derivative having a first unsaturated bond and the 4- (2- (4-benzhydrylamine-phenylethene) pyridinium bromide derivative having a second unsaturated bond are mixed and then subjected to a click chemical reaction, so that the aggregation-induced emission material can be obtained.
In step S01, the D-alanine derivative having the first unsaturated bond and the 4- (2- (4-benzhydrylaminophenylethylene) pyridinium bromide derivative having the second unsaturated bond are provided, and the D-alanine derivative having the first unsaturated bond and the 4- (2- (4-benzhydrylaminophenylethylene) pyridinium bromide derivative having the second unsaturated bond are provided as above, and are not described herein again for the sake of brevity.
In some embodiments, the molar ratio of the D-alanine derivative having the first unsaturated bond to the 4- (2- (4-benzhydrylaminophenylethylene) pyridinium bromide derivative having the second unsaturated bond is 1 (0.1 to 10), the chemical click reaction is facilitated by controlling the molar ratio of the D-alanine derivative having the first unsaturated bond to the 4- (2- (4-benzhydrylaminophenylethylene) pyridinium bromide derivative having the second unsaturated bond, and in some embodiments, the molar ratio of the D-alanine derivative having the first unsaturated bond to the 4- (2- (4-benzhydrylaminophenylethylene) pyridinium bromide derivative having the second unsaturated bond is selected from the group consisting of 1: 0.1, 1: 0.5, 1: 1, 1: 1.5, 1: 2, 1: 2.5, 1: 3,1: 3.5,1: 4,1: 4.5,1: 5,1: 5.5,1: 6,1: 6.5,1: 7,1: 7.5,1: 8,1: 8.5,1: 9,1: 9.5,1: 10.
in step S02, the D-alanine derivative having the first unsaturated bond and the 4- (2- (4-benzhydrylamine phenylethene) pyridinium bromide derivative having the second unsaturated bond are mixed and subjected to click chemical reaction, so as to obtain the aggregation-induced emission material.
The D-alanine derivative containing the first unsaturated bond and the 4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide derivative containing the second unsaturated bond are subjected to addition reaction to realize connection.
In some embodiments, when the metabolizing group is 3-tetrazine-D-alanine and the aggregation-inducing luminescent group is 1-trans-cyclooctene-4- (2- (4-benzhydrylamine-phenyl-ethylene) pyridinium bromide, the 3-tetrazine-D-alanine is mixed with 1-trans-cyclooctene-4- (2- (4-benzhydrylamine-phenyl-ethylene) pyridinium bromide, the tetrazine group in the 3-tetrazine-D-alanine and the trans-cyclooctene group in the 1-trans-cyclooctene-4- (2- (4-benzhydrylamine-phenyl-ethylene) pyridinium bromide undergo a diels-alder cycloaddition reaction to synthesize the aggregation-inducing luminescent material.
In a third aspect of the embodiments, there is provided a bacterium having an aggregation-inducing luminescent material applied for labeling and killing, wherein the bacterium includes at least one of gram-positive bacteria and gram-negative bacteria whose cell walls contain a peptidoglycan component.
The aggregation-induced emission material provided by the third aspect of the embodiment of the application is applied to marking and killing bacteria, and because the metabolic groups included in the aggregation-induced emission material can mark at least one of gram-positive bacteria and gram-negative bacteria of which the cell walls contain peptidoglycan components, the aggregation-induced emission material can realize in-situ removal of the bacteria, and has high detection speed and good application effect.
In some embodiments, the bacteria provided include, but are not limited to, at least one of the species escherichia coli, staphylococcus aureus, pseudomonas aeruginosa.
A fourth aspect of the embodiments of the present application provides a sterilization method using an aggregation-induced emission material for sterilization, including the following steps:
G01. providing a sample to be sterilized, and carrying out sterilization,
G02. mixing a sample to be sterilized with an aggregation-induced emission material, and incubating to obtain a blending solution;
G03. and carrying out laser irradiation treatment on the blended solution to obtain a sterilized sample.
The third aspect of the embodiment of the application provides a sterilization method using aggregation-induced emission material to sterilize, the sterilization method uses the aggregation-induced emission material to co-incubate with bacteria, so that metabolic groups participate in the synthesis process of the bacteria by synthesizing cell wall peptidoglycan to specifically mark the bacteria; and then the laser irradiation treatment is utilized to initiate the aggregation induction of the luminescent groups to form active oxygen groups to sterilize bacteria, so that the rapid, efficient and fixed-point sterilization treatment is realized.
In step G01, a sample to be sterilized is provided, wherein the sample to be sterilized contains bacteria, including but not limited to gram-negative bacteria or gram-positive bacteria.
In step G02, the sample to be sterilized and the aggregation-induced emission material are mixed and incubated to obtain a blended solution.
In some embodiments, the temperature of the incubation is 36-37 ℃ and the time of the incubation is 0.5-12 hours. In some embodiments, the temperature of incubation is 37 ℃ and the time of incubation is 0.5 hours, 1 hour, 1.5 hours, 2 hours, 2.5 hours, 3 hours, 3.5 hours, 4 hours, 4.5 hours, 5 hours, 5.5 hours, 6 hours, 6.5 hours, 7 hours, 7.5 hours, 8 hours, 8.5 hours, 9 hours, 9.5 hours, 10 hours, 10.5 hours, 11 hours, 11.5 hours, 12 hours, 16 hours, 18 hours, 24 hours.
In some embodiments, aggregation-inducing luminescent material is provided for mixed co-incubation with a sample to be sterilized, wherein the concentration of aggregation-inducing luminescent material is 1-1000. mu. mol/L. In some embodiments, concentrations of aggregation-inducing luminescent materials include, but are not limited to, 5. mu. mol/L, 10. mu. mol/L, 15. mu. mol/L, 20. mu. mol/L, 25. mu. mol/L, 30. mu. mol/L, 35. mu. mol/L, 40. mu. mol/L, 45. mu. mol/L, 50. mu. mol/L, 55. mu. mol/L, 60. mu. mol/L, 65. mu. mol/L, 70. mu. mol/L, 75. mu. mol/L, 80. mu. mol/L, 85. mu. mol/L, 90. mu. mol/L, 95. mu. mol/L, 100. mu. mol/L, 110. mu. mol/L, 120. mu. mol/L, 150. mu. mol/L, 200. mu. mol/L, 300. mol/L, 400. mu. mol/L, 500. mu. mol/L, 600. mol/L, 700. mu. mol/L, or, 800. mu. mol/L, 1000. mu. mol/L.
And G03, carrying out laser irradiation treatment on the blended liquid to obtain a sterilized sample.
In some embodiments, the laser intensity of the laser irradiation treatment is 10 to 1000mW/cm2The laser wavelength is 280-500 nm; the laser irradiation treatment is carried out for 1 to 200 minutes. Through laser irradiation treatment, high-concentration active oxygen groups can be generated, sterilization treatment is realized, the provided aggregation-induced emission material has excellent marking and killing effects on gram-positive bacteria and gram-negative bacteria, broad-spectrum and efficient bacteria marking and in-situ removal can be realized, and drug resistance is not easy to generate.
Further, an active oxygen group generated after the aggregation-induced emission material is irradiated by light is detected by a microplate reader by using an active oxygen indicator, namely dihydrodichlorofluorescein (DCFH-DA).
Further, the photodynamic bactericidal effect of the aggregation-induced emission material was verified by the bacterial growth curve after the treatment.
The following description will be given with reference to specific examples.
Example A1
Aggregation-induced luminescent material and preparation method thereof
The aggregation-induced emission material is formed by connecting 3-tetrazine-D-alanine and 1-trans-cyclooctene-4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide salt through chemical bonds.
The preparation method of the aggregation-induced emission material comprises the following steps:
providing a molar ratio of 1: 0.1 of 3-tetrazine-D-alanine and 1-trans-cyclooctene-4- (2- (4-benzhydrylamine-phenylethene) pyridine bromide,
mixing 3-tetrazine-D-alanine and 1-trans-cyclooctene-4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide, stirring and mixing at room temperature, and carrying out click chemical reaction to obtain the aggregation-induced luminescent material.
Example A2
Aggregation-induced luminescent material and preparation method thereof
The aggregation-induced emission material is formed by connecting 3-tetrazine-D-alanine and 1-trans-cyclooctene-4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide salt through chemical bonds.
The preparation method of the aggregation-induced emission material comprises the following steps:
providing a molar ratio of 1: 1.5 of 3-tetrazine-D-alanine and 1-trans-cyclooctene-4- (2- (4-benzhydrylamine-phenylethene) pyridine bromide,
mixing 3-tetrazine-D-alanine and 1-trans-cyclooctene-4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide, stirring and mixing at room temperature, and carrying out click chemical reaction to obtain the aggregation-induced luminescent material.
Example A3
Aggregation-induced luminescent material and preparation method thereof
The aggregation-induced emission material is formed by connecting 3-tetrazine-D-alanine and 1-trans-cyclooctene-4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide salt through chemical bonds.
The preparation method of the aggregation-induced emission material comprises the following steps:
providing a molar ratio of 1: 3-tetrazine-D-alanine and 1-trans-cyclooctene-4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromine salt,
mixing 3-tetrazine-D-alanine and 1-trans-cyclooctene-4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide, stirring and mixing at room temperature, and carrying out click chemical reaction to obtain the aggregation-induced luminescent material.
Example A4
Aggregation-induced luminescent material and preparation method thereof
The aggregation-induced emission material is formed by connecting 3-tetrazine-D-alanine and 1-trans-cyclooctene-4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide salt through chemical bonds.
The preparation method of the aggregation-induced emission material comprises the following steps:
providing a molar ratio of 1: 8 of 3-tetrazine-D-alanine and 1-trans-cyclooctene-4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide,
mixing 3-tetrazine-D-alanine and 1-trans-cyclooctene-4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide, stirring and mixing at room temperature, and carrying out click chemical reaction to obtain the aggregation-induced luminescent material.
Example A5
Aggregation-induced emission material and preparation method thereof
The aggregation-induced emission material is formed by connecting 3-tetrazine-D-alanine and 1-trans-cyclooctene-4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide through chemical bonds.
The preparation method of the aggregation-induced emission material comprises the following steps:
providing a molar ratio of 1: 10 of 3-tetrazine-D-alanine and 1-trans-cyclooctene-4- (2- (4-benzhydrylamine phenylethene) pyridine bromide,
mixing 3-tetrazine-D-alanine and 1-trans-cyclooctene-4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide, stirring and mixing at room temperature, and carrying out click chemical reaction to obtain the aggregation-induced luminescent material.
Example B1
The aggregation-induced emission material obtained in example a1 was used for sterilization, and the sterilization method included the following steps:
providing a sample to be sterilized, and carrying out sterilization,
mixing a sample to be sterilized with an aggregation-induced emission material, and incubating to obtain a blending solution; wherein the incubation temperature is 37 ℃, the incubation time is 0.5 hour, and the concentration of the aggregation-induced emission material is 10 mu mol/L;
subjecting the blend to laser irradiation treatment, wherein the laser intensity of the laser irradiation treatment is 10mW/cm2The laser wavelength is 280 nm; the time of the laser irradiation treatment was 20 minutes, and a sterilized sample was obtained.
Example B2
The aggregation-induced emission material obtained in example a2 was used to perform a sterilization process, the sterilization process comprising the steps of:
providing a sample to be sterilized, and carrying out sterilization,
mixing a sample to be sterilized with an aggregation-induced emission material, and incubating to obtain a blending solution; wherein the incubation temperature is 37 ℃, the incubation time is 2 hours, and the concentration of the aggregation-induced emission material is 30 mu mol/L;
subjecting the blend solution to laser irradiation treatment, wherein the laser intensity of the laser irradiation treatment is 10mW/cm2The laser wavelength is 280 nm; the time of the laser irradiation treatment was 20 minutes, and a sterilized sample was obtained.
Example B3
The aggregation-induced emission material obtained in example a3 was used to perform a sterilization process, the sterilization process comprising the steps of:
providing a sample to be sterilized, and carrying out sterilization,
mixing a sample to be sterilized with an aggregation-induced emission material, and incubating to obtain a blending solution; wherein the incubation temperature is 37 ℃, the incubation time is 3 hours, and the concentration of the aggregation-induced emission material is 50 mu mol/L;
subjecting the blend to laser irradiation treatment, wherein the laser intensity of the laser irradiation treatment is 10mW/cm2The laser wavelength is 280 nm; the time for the laser irradiation treatment was 20 minutesAnd (5) obtaining a sterilized sample.
Example B4
The aggregation-induced emission material obtained in example a4 was used for sterilization, and the sterilization method included the following steps:
providing a sample to be sterilized, and carrying out sterilization,
mixing a sample to be sterilized with an aggregation-induced emission material, and incubating to obtain a blending solution; wherein the incubation temperature is 37 ℃, the incubation time is 0.5 hour, and the concentration of the aggregation-induced emission material is 80 mu mol/L;
subjecting the blend to laser irradiation treatment, wherein the laser intensity of the laser irradiation treatment is 10mW/cm2The laser wavelength is 280 nm; the time for the laser irradiation treatment was 20 minutes, and a sterilized sample was obtained.
Example B5
The aggregation-induced emission material obtained in example a5 was used for sterilization, and the sterilization method included the following steps:
providing a sample to be sterilized, and carrying out sterilization,
mixing a sample to be sterilized with an aggregation-induced emission material, and incubating to obtain a blending solution; wherein the incubation temperature is 37 ℃, the incubation time is 0.5 hour, and the concentration of the aggregation-induced emission material is 120 mu mol/L;
subjecting the blend to laser irradiation treatment, wherein the laser intensity of the laser irradiation treatment is 10mW/cm2The laser wavelength is 280 nm; the time of the laser irradiation treatment was 20 minutes, and a sterilized sample was obtained.
Property measurement
AIE characteristic verification of novel aggregation-induced emission material
1) Dissolving aggregation-induced emission material (TDA) with tetrahydrofuran to prepare mother liquor with the concentration of 2 mM;
2) sucking mother liquor, and preparing into tetrahydrofuran/diethyl ether mixed solution with diethyl ether volume ratios of 0%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80% and 90%;
3) these mixed solutions were photographed under a white light lamp and an ultraviolet lamp in this order.
(II) evaluation of labeling Effect of novel aggregation-inducing luminescent Material on bacteria
1) Taking 200 μ L of bacterial suspension with OD600 value of 0.5, and incubating with aggregation-induced emission material with final concentration of 20 μ M in shaking table at 37 deg.C for 2 hr;
3) the mixed solution was centrifuged at 7000 rpm for 15 minutes, washed 2 times,
4) resuspending in Phosphate Buffered Saline (PBS), and diluting the bacterial liquid by 10 times; standing in an eight-hole chamber, and finally placing under a laser confocal microscope (Zeiss LSM 710) for imaging;
5) the photo is observed and photographed under a laser confocal microscope, and the probe selects a fluorescence excitation wavelength region of 488nm and a fluorescence emission wavelength region of 500-700 nm.
(III) measurement of active oxygen Generation efficiency of aggregation-induced emission Material
1) The BCG suspension with OD600 of 0.5 and the aggregation-induced emission material with the final concentration of 20 MuM are subjected to shaking incubation for 2 hours in a shaking table at 37 ℃, wherein the rotating speed of the shaking table is set to be 110 r/min;
2) centrifuging the mixed solution at 7000 rpm for 15 minutes, and washing for 2 times;
3) re-suspending PBS (phosphate buffer solution), and adding a DCFH-DA active oxygen indicator;
4) quickly irradiating under a white light for 0, 4, 8, 12, 16 and 20 minutes;
5) and (3) placing the sample under a microplate reader to detect the fluorescence intensity of DCFH-DA, and selecting the fluorescence excitation wavelength of 488nm and the fluorescence emission wavelength of 525 nm.
(IV) evaluation of Fungicide Effect Properties of novel aggregation-induced emission Material
1) The BCG suspension with OD600 of 0.5 and TDA with final concentration of 20 μ M were incubated in a shaker at 37 ℃ for 2 hours with shaking;
2) centrifuging the mixed solution at 7000 rpm for 15 minutes, and washing for 2 times;
3) resuspending the 7H9 culture medium, irradiating the bacterial solution for 30 minutes by adopting a 100W white light lamp, and then placing the solution in a shaking table at 37 ℃ for shake culture;
4) after shaking for 1, 2, 4, 8 and 12 hours, the OD600 values of the bacterial solutions were measured.
Analysis of results
AIE characteristic verification of novel aggregation-induced emission material
The experimental result is shown in fig. 1, the tetrahydrofuran solution is a good solvent of TDA, the ether is a poor solvent of TDA, the TDA has no fluorescence signal in the 100% tetrahydrofuran solution, the TDA fluorescence signal is gradually enhanced with the continuous increase of the volume of the ether, and the result shows that the aggregation-induced emission metabolic material has excellent aggregation-induced emission characteristics.
(II) evaluation of labeling Effect of novel aggregation-inducing luminescent Material on bacteria
The experimental result is shown in fig. 2, and the result shows that the aggregation-induced emission metabolic fluorescent probe successfully marks bacteria (green represents a probe-marked fluorescent signal), has an extremely strong fluorescent signal, and can be used for detecting bacteria.
(III) measurement of active oxygen Generation efficiency of aggregation-induced emission Material
The experimental result is shown in fig. 3, the DCFH-DA fluorescence intensity is obviously enhanced along with the increase of the illumination time, which indicates that the aggregation-induced emission metabolic material has high active oxygen generation efficiency and can be used for photodynamic sterilization.
(IV) evaluation of Fungicide Effect of novel aggregation-induced emission Material
The experimental result is shown in fig. 4, the aggregation-induced emission material has excellent antibacterial performance under laser irradiation, and the in vitro bacteriostasis rate of the aggregation-induced emission material can reach more than 85%.
The results of the above examples show that the aggregation-induced emission material provided by the invention has aggregation-induced emission characteristics and photodynamic sterilization performance, and can be used for rapid detection and in-situ removal of bacteria.
The above description is only exemplary of the present application and should not be taken as limiting the present application, as any modification, equivalent replacement, or improvement made within the spirit and principle of the present application should be included in the protection scope of the present application.
Claims (10)
1. An aggregation-induced emission material comprising a metabolic group and an aggregation-induced emission group, wherein the metabolic group comprises a D-alanine derivative having a first unsaturated bond, and the aggregation-induced emission group comprises a 4- (2- (4-benzhydrylamine-phenylethylene) pyridinium bromide derivative having a second unsaturated bond, the metabolic group and the aggregation-induced emission group being connected by a chemical bond.
2. The aggregation-induced emission material according to claim 1, wherein the first unsaturated bond includes an unsaturated bond containing a nitrogen atom; and/or the presence of a gas in the gas,
the second unsaturated bond includes an unsaturated bond containing a carbon atom.
3. The aggregation-induced emission material according to claim 1, wherein the D-alanine derivative having the first unsaturated bond includes any one of azide, tetrazine, thiol, alkyne, trans-cyclooctene, or alkene-modified D-alanine; and/or the presence of a gas in the gas,
the 4- (2- (4-benzhydrylamine phenylethylene) pyridine bromide salt derivative containing the second unsaturated bond comprises any one of alkyne, trans-cyclooctene, alkene, azide, tetrazine or sulfydryl modified 4- (2- (4-benzhydrylamine phenylethylene) pyridine bromide salt.
4. The aggregation induced emission material according to claim 1, wherein the metabolizing group in the aggregation induced emission material is 3-tetrazine-D-alanine, and the aggregation induced emission group is 1-trans-cyclooctene-4- (2- (4-benzhydrylamine-phenylethylene) pyridinium bromide.
5. The aggregation-induced emission material according to claim 4, wherein the wavelength of the excitation light of the aggregation-induced emission material is 250 to 500 nm; the characteristic fluorescence emission spectrum is 500-900 nm.
6. A method for preparing the aggregation-induced emission material according to any one of claims 1 to 5, comprising the steps of:
providing a D-alanine derivative having a first unsaturated bond and a 4- (2- (4-benzhydrylamine phenylethene) pyridinium bromide derivative having a second unsaturated bond;
and mixing the D-alanine derivative containing the first unsaturated bond and the 4- (2- (4-benzhydrylamine phenyl ethylene) pyridine bromide derivative containing the second unsaturated bond, and carrying out click chemical reaction to obtain the aggregation-induced luminescent material.
7. The method for preparing an aggregation-induced emission material according to claim 6, wherein the molar ratio of the D-alanine derivative having the first unsaturated bond to the 4- (2- (4-benzhydrylamine-phenylethene) pyridinium bromide derivative having the second unsaturated bond is 1 (0.1-10).
8. The use of the aggregation-inducing luminescent material according to any one of claims 1 to 5 for labeling and killing bacteria, wherein the bacteria comprise at least one of gram-positive bacteria and gram-negative bacteria having a peptidoglycan component in their cell walls.
9. A sterilization method using the aggregation-induced emission material according to any one of claims 1 to 5, the sterilization method comprising the steps of:
providing a sample to be sterilized, and carrying out sterilization,
mixing the sample to be sterilized with the aggregation-induced emission material for incubation to obtain a blended solution;
and carrying out laser irradiation treatment on the blended liquid to obtain a sterilized sample.
10. The sterilization method according to claim 9, wherein the incubation temperature is 36 to 37 ℃, and the incubation time is 0.5 to 24 hours; and/or the presence of a gas in the gas,
the concentration of the aggregation-induced emission material is 1-1000 mu mol/L; and/or the presence of a gas in the gas,
the laser intensity of the laser irradiation treatment is 10-1000 mW/cm2Laser, laser beamThe wavelength is 280-500 nm; the laser irradiation treatment time is 1-200 minutes.
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| CN110981742A (en) * | 2019-09-24 | 2020-04-10 | 浙江工业大学 | Phenylalanine derivative with aggregation-induced emission property and preparation and application thereof |
| CN111334291A (en) * | 2020-03-24 | 2020-06-26 | 天津市口腔医院 | Aggregation-induced emission fluorescence turn-on probe and preparation method and application thereof |
| US20210228721A1 (en) * | 2020-01-24 | 2021-07-29 | The Hong Kong University Of Science And Technology | Aggregation induced emission-bacteriophage bioconjugates |
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| CN110981742A (en) * | 2019-09-24 | 2020-04-10 | 浙江工业大学 | Phenylalanine derivative with aggregation-induced emission property and preparation and application thereof |
| US20210228721A1 (en) * | 2020-01-24 | 2021-07-29 | The Hong Kong University Of Science And Technology | Aggregation induced emission-bacteriophage bioconjugates |
| CN111334291A (en) * | 2020-03-24 | 2020-06-26 | 天津市口腔医院 | Aggregation-induced emission fluorescence turn-on probe and preparation method and application thereof |
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