Aggregation-induced emission molecule, nano motor, preparation method and application

Abstract

The invention provides an aggregation-induced emission molecule, a nano motor and a preparation method and application of the aggregation-induced emission molecule, the aggregation-induced emission molecule is used for near-infrared emission, has photo-thermal properties, and has the characteristics of near-infrared II region luminescence, heat production and good light stability; the nano motor is prepared by taking an asymmetric double-mesoporous nano material with different pore diameters as a support material and selectively loading aggregation-induced emission molecules on one side of the support material with a larger pore diameter; under the irradiation of near-infrared light, the aggregation-induced emission molecules with the photothermal effect can form a non-uniform thermal gradient to push the self-thermophoresis movement of the nano motor; tumor sites can be diagnosed and reported under the mediation of near-infrared II region imaging; through the photo-thermal effect, the motor can destroy tumor interstitial cells and degrade tumor matrix components; and in combination with autothermophoresis, blood vessels can be penetrated, so that penetration to the deep layer of the tumor can be realized.

Description

Technical Field

[0001] The present invention relates to the field of medical imaging and tumor penetration and treatment technology, and in particular to an aggregation-induced luminescence molecule, a nanomotor, and a preparation method and application thereof. Background Art

[0002] Phototherapy nanomedicines have attracted widespread attention in the treatment of malignant tumors. Excellent near-infrared II region imaging and deep tumor penetration are the two most important properties of nanomedicines in tumor phototherapy. However, the dense tumor interstitial microenvironment barrier hinders the ability of nanomedicines to penetrate tumors. It is reported that self-thermophoretic nanomotors with autonomous movement can overcome this obstacle while increasing tumor penetration. Therefore, luminescent molecules can be assembled on such self-thermophoretic motors as imaging units. Unfortunately, on the one hand, traditional near-infrared fluorescent dyes (such as FDA-approved ICG) will experience aggregation-induced quenching in the aggregated state, which will significantly reduce their visualization imaging performance in nanoparticle applications. In addition, long-term imaging with 808nm laser excitation of ICG will cause damage to its structure, making the fluorescence and photothermal properties unable to be stable for a long time; on the other hand, due to the competitive relationship between photothermal conversion and near-infrared II region emission, the simultaneous assembly of the two functional materials may cause conflicts between functions.

[0003] Aggregation-induced emission molecules have attracted much attention in biological applications. Through molecular engineering, they can be made to have the ability to emit near-infrared light and generate heat at the same time. Based on this, using them as components of nanomotors can simultaneously achieve luminescent imaging diagnosis and heat generation drive of the motor. However, no research in this area has been reported so far.

[0004] Therefore, the related technologies in the prior art regarding aggregation-induced emission molecules that simultaneously emit near-infrared light and generate heat still need to be further improved. Summary of the invention

[0005] In view of this, the present invention proposes an aggregation-induced luminescence molecule, a nanomotor, a preparation method and an application, which solve the technical problems in the prior art that traditional near-infrared fluorescent molecules have aggregation-induced quenching and poor photostability, and that photothermally driven nanomotors cannot have the functional conflict of near-infrared luminescence.

[0006] The technical solution of the present invention is achieved in this way:

[0007] In one aspect, the present invention provides an aggregation-induced emission molecule, the chemical structure of which is:

[0008] Wherein, R is a group containing an alkyl chain.

[0009] On the basis of this technical solution, it is further preferred that the alkyl chain is a straight chain with 1-20 carbon atoms, a branched chain with 1-20 carbon atoms, a cyclic alkyl chain with 1-20 carbon atoms, an alkyl chain in which the carbon atoms are substituted by oxygen atoms, alkenyl groups, alkynyl groups, aryl groups, carbonyl groups, hydroxyl groups, amino groups, carboxyl groups, cyano groups, nitro groups or ester groups, and an alkyl chain in which the hydrogen atoms are substituted by fluorine atoms, chlorine atoms, bromine atoms or iodine atoms.

[0010] On the basis of this technical solution, it is further preferred that the aggregation-induced emission molecule uses thiophthalenetetracarboxylic acid diimide with a long alkyl chain as the electron acceptor group and fluorenyltriphenylamine as the molecular rotor and electron donor unit.

[0011] In a second aspect, the present invention further provides a nanomotor, comprising the aggregation-inducing molecule, the asymmetric dual-mesoporous nanomaterial and the tumor targeting material as described in the first aspect.

[0012] On the basis of this technical solution, more preferably, the mesopore diameter of the asymmetric dual-mesoporous nanomaterial is 2-50 nm.

[0013] On the basis of this technical solution, it is further preferred that the asymmetric dual-mesoporous nanomaterial includes one of a combination of inorganic mesoporous silicon-organic mesoporous silicon, a combination of inorganic mesoporous silicon-inorganic mesoporous silicon, a combination of mesoporous silicon-mesoporous dopamine or a combination of mesoporous silicon-mesoporous carbon.

[0014] On the basis of this technical solution, more preferably, the mesoporous silicon includes spheres, rods or tubes.

[0015] On the basis of this technical solution, more preferably, the tumor targeting material is RNA, polypeptide, or protein.

[0016] In a third aspect, the present invention further provides a method for preparing the nanomotor according to the second aspect, comprising the following steps:

[0017] preparing aggregation-induced emission molecules;

[0018] Asymmetric dual-mesoporous nanomaterials with different pore sizes were selected as the supporting materials for nanomotors;

[0019] Utilizing the different pore sizes of the asymmetric dual-mesoporous nanomaterials, the aggregation-induced emission molecule is selectively loaded in one of the pore sizes using a co-precipitation method or an adsorption method;

[0020] Modification of nanomotors with tumor-targeting materials.

[0021] In a fourth aspect, the present invention further provides the use of the aggregation-induced emission molecule described in the first aspect, the nanomotor described in the second aspect, and the nanomotor obtained by the preparation method described in the third aspect in targeted fluorescence imaging of tumors in the near-infrared II zone and achieving deep tumor penetration:

[0022] On the basis of this technical solution, it is further preferred that the aggregation-inducing molecules described in the first aspect, the nanomotors described in the second aspect, and the nanomotors obtained by the preparation method described in the third aspect are also included in the application of tumor diagnosis and deep tumor penetration.

[0023] The aggregation-induced emission molecule, nanomotor, preparation method and application provided by the present invention have the following beneficial effects compared with the prior art:

[0024] The present invention provides an aggregation-induced luminescence molecule, which is used for near-infrared emission and has photothermal properties, and has the characteristics of luminescence in the near-infrared II region, heat generation, and good photostability; at the same time, the present invention provides a nanomotor that uses an asymmetric double-mesoporous nanomaterial with different pore sizes as a supporting material, and selectively loads the above-mentioned aggregation-induced luminescence molecule on the larger pore size side of the supporting material; under the irradiation of near-infrared light, the aggregation-induced luminescence molecule with a photothermal effect can form an uneven thermal gradient around the nanomotor, thereby promoting the self-thermophoretic movement of the nanomotor;

[0025] The near-infrared luminescent self-thermophoretic mesoporous nanomotor based on aggregation-induced luminescence molecules provided by the present invention uses aggregation-induced luminescence molecules as both a driving unit and an imaging unit, and can realize the functional combination of near-infrared II region imaging and thermal driving;

[0026] The nanomotor can diagnose and report tumor sites under the mediation of near-infrared II imaging; through photothermal action, the motor can destroy tumor interstitial cells and degrade tumor matrix components; and combined with self-thermophoresis, it can penetrate blood vessels and achieve deep penetration into the tumor. This invention is expected to be widely used in smart drug delivery and nanomedicine. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings required for use in the embodiments or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0028] Figure 1 This is a nuclear magnetic resonance hydrogen spectrum of the aggregation-induced emission molecule NDA-FT of Example 1 of the present invention obtained by testing in deuterated chloroform solvent;

[0029] Figure 2 This is a carbon nuclear magnetic resonance spectrum of the aggregation-induced emission molecule NDA-FT obtained by testing in deuterated chloroform solvent according to Example 1 of the present invention;

[0030] Figure 3 This is the mass spectrum of the aggregation-induced emission molecule NDA-FT of Example 1 of the present invention;

[0031] Figure 4 The absorption and emission spectra of the aggregation-induced emission molecule NDA-FT of Example 1 of the present invention obtained by testing in tetrahydrofuran solvent;

[0032] Figure 5 This is a fluorescence spectrum obtained by testing the aggregation-induced emission molecule NDA-FT of Example 1 of the present invention in a mixed solvent of water and tetrahydrofuran;

[0033] Figure 6 This is a transmission electron microscope image of an asymmetric dual-mesoporous nanomaterial M&P with different pore sizes according to Example 2 of the present invention;

[0034] Figure 7 Schematic diagram of the preparation of the nanomotor M&P-NFT / R according to Example 2 of the present invention;

[0035] Figure 8 This is a transmission electron microscope image of the nanomotor M&P-NFT / R according to Example 2 of the present invention;

[0036] Fig. 9 The absorption and emission spectra of the nanomotor M&P-NFT / R according to Example 2 of the present invention;

[0037] Fig.10 The self-thermophoresis trajectories of the nanomotor M&P-NFT / R of Application Example 1 of the present invention at different laser powers;

[0038] Fig.11 This is a tumor targeting imaging image of the nanomotor M&P-NFT / R of Application Example 2 of the present invention;

[0039] Fig.12 This is a test of the nanomotor M&P-NFT / R in Application Example 3 of the present invention on the remodeling and penetration of the tumor interstitial environment. DETAILED DESCRIPTION

[0040] The following will be combined with the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0041] The present invention provides an aggregation-induced emission molecule, a nanomotor, a preparation method and an application thereof. The nanomotor is prepared by using an asymmetric double-mesoporous nanomaterial with different pore sizes as a supporting material, and selectively loading the aggregation-induced emission molecule on the larger pore size side of the supporting material. The aggregation-induced emission molecule is used as a driving unit and an imaging unit at the same time, thereby realizing the functional combination of near-infrared second-zone imaging and thermal driving.

[0042] Example 1

[0043] An aggregation-induced emission molecule, the chemical structure of the aggregation-induced emission molecule is:

[0044]

[0045] Wherein, R is a group containing an alkyl chain.

[0046] In this embodiment, specifically, the alkyl chain is a straight chain with 1-20 carbon atoms, a branched chain with 1-20 carbon atoms, a cyclic alkyl chain with 1-20 carbon atoms, an alkyl chain in which carbon atoms are substituted by oxygen atoms, alkenyl groups, alkynyl groups, aryl groups, carbonyl groups, hydroxyl groups, amino groups, carboxyl groups, cyano groups, nitro groups or ester groups, and an alkyl chain in which hydrogen atoms are substituted by fluorine atoms, chlorine atoms, bromine atoms or iodine atoms.

[0047] In this embodiment, specifically, the aggregation-induced emission molecule uses thiophthalene tetracarboxylic acid diimide with a long alkyl chain as an electron acceptor group, and fluorenyl triphenylamine as a molecular rotor and an electron donor unit.

[0048] Specifically, first, the present invention adopts the structural design strategy of electron donor-electron acceptor-electron donor to ensure that the dye has strong absorption in the near-infrared region (750-850nm) and can stably emit within the range of (900-1400nm). In order to overcome the luminescence quenching effect under the aggregated state, the aggregation-induced luminescence characteristic group fluorenyl triamine is introduced in the design to ensure that the dye can still maintain bright fluorescence under the aggregated state. Fluorenyl triamine not only enhances the electron donor-electron acceptor structural characteristics of the molecule, but the introduction of the planar block also improves the molar extinction coefficient, thereby enhancing the light absorption capacity of the dye. However, although the aggregation-induced luminescence characteristics improve the efficiency of the fluorescence radiation transition, it may inhibit the non-radiative transition (i.e., heat generation), which is unfavorable for the realization of the photothermal function. For this reason, a long alkyl chain is introduced on the electron acceptor group, and the π-π stacking under the aggregated state is suppressed by the spatial isolation between molecules, providing enough free space in the molecule, thereby ensuring the moderate enhancement of the non-radiative energy attenuation, which helps to exert the photothermal effect.

[0049] In addition, all chemical structural groups are designed to be stable and not easily decomposed, ensuring that the molecules have reliable and lasting luminescence and photothermal properties in the near-infrared region II. Subsequently, through pore-selective assembly, this type of molecule is loaded on the larger pore side of the asymmetric double mesoporous material and assembled into a nanomotor. This type of motor will have both photothermal (for driving) and luminescence (for imaging) properties, and can reshape the tumor interstitial microenvironment under laser irradiation to achieve deep penetration of the tumor.

[0050] In some embodiments, R is When the aggregation-induced emission molecule is prepared, the method comprises the following steps:

[0051]

[0052] Under the protection of nitrogen, NaH (210 mg, 5.24 mmol) was added to the re-evaporated dimethylformamide in a 10 mL ice bath. 2-(4-bromophenyl)acetonitrile (513 mg, 2.62 mmol) was added and stirred for 30 min, followed by CS2 (300 mg, 3.93 mmol). The temperature was raised to room temperature and the reaction was continued for another 2 h. The reaction solution changed from colorless to bright green and then gradually to brown.

[0053] Then, 4,5,9,10-tetrabromo-2,7-di(2-octyldodecyl)benzo[lmn][3,8]-phenanthroline-1,3,6,8(2H,7H)-tetraone (300 mg, 0.262 mmol) was added all at once and stirred at room temperature for 1 hour, and the solution turned dark purple. The reaction was then quenched with 20 ml of saline. The compound was extracted with ethyl acetate. The collected organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was subjected to column chromatography with dichloromethane and petroleum ether (2:1) as eluent to obtain compound 1 as a dark green solid with a yield of 56%;

[0054] Under nitrogen protection, compound 1 (100 mg, 0.07 mmol), di(9,9-dimethyl-9H-fluorene-2-yl)amine (84.2 mg, 0.21 mmol), disodium tert-butyl (26.8 mg, 0.28 mmol), 4,5-di(diphenylphosphine)-9,9-dimethylanthracene (9.6 mg, 0.1 mmol), tri(2-benzylacetone)dipalladium (4.6 mg, 0.05 mmol) were dissolved in toluene, refluxed at 120°C for 12 h, extracted with dichloromethane after cooling, and washed with brine three times. After drying over anhydrous Na2SO4, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using dichloromethane and petroleum ether (2:1) as eluent to obtain a green powder, i.e., the aggregation-induced emission molecule, with a yield of 32%.

[0055] Results: Figure 1-3 As shown, Figure 1 is the nuclear magnetic resonance hydrogen spectrum of the aggregation-induced emission molecule, Figure 2 is the carbon nuclear magnetic resonance spectrum of the aggregation-induced emission molecule, Figure 3 For the mass spectrum.

[0056] The hydrogen spectrum data is: 1 H NMR (500MHz, CDCl3), δ (ppm): 7.67 (d, J = 8.0 Hz, 4H), 7.56 (d, J = 7.9 Hz, 4H), 4. 22-4.08(m,4H),1.99(s,2H),1.27(t,J=35.6Hz,64H),0.85(d,J=5.6Hz,12H).

[0057] 1 H NMR(500MHz,CDCl3,Supplementary Fig.2) δ[ppm]:7.67(m,8H),7.56(d,J=8.5Hz,4H),7.41(d,J=7.0Hz,4H),7.26-7.24(m,18H),7.2 1(d,J=8Hz,4H),4.22-4.10(m,4H),2.01(s,2H),1.44(s,24H),1.21(m,64H),0.89-0.76(m,12H).

[0058] The carbon spectrum data is 13 C NMR(126MHz,CDCl3,Supplementary Fig.3)δ[ppm]:162.32,155.42,155.35,153.65,153.50,147.44,146.33,138.77,135.35,128.26,127.07,126.81 ,124.20,123.58,122.56,120.87,119.66,46.94,31.93,31.88,30.11,29.64,29.34,27.06,26.38,22.68,14.14.

[0059] Mass spectrometry data are MS (MALDI-TOF, Supplementary Fig. 4) [m / z]:calcdforC 132 H 142 N6O4S4,2004.0009; found,2004.006.

[0060] in addition, Figure 4 The absorption and emission spectra of the aggregation-induced emission molecule NDA-FT of Example 1 obtained by testing in tetrahydrofuran solvent; Figure 5This is the fluorescence spectrum of the aggregation-induced emission molecule NDA-FT of Example 1 of the present invention tested in a mixed solvent of water and tetrahydrofuran; Figure 4-5 As shown, it can be seen that the absorption and emission peaks of the molecule are at 745nm and 1100nm respectively. With the increase of water content, the fluorescence intensity gradually increases, showing an obvious aggregation-induced enhanced luminescence phenomenon.

[0061] Example 2

[0062] A nanomotor comprises the aggregation-induced emission molecule, an asymmetric dual-mesoporous nanomaterial and a tumor targeting material as described in one aspect.

[0063] In this embodiment, specifically, the mesopore diameter of the asymmetric dual-mesoporous nanomaterial is 2-50 nm.

[0064] In this embodiment, specifically, the asymmetric dual-mesoporous nanomaterial includes one of a combination of inorganic mesoporous silicon-organic mesoporous silicon, a combination of inorganic mesoporous silicon-inorganic mesoporous silicon, a combination of mesoporous silicon-mesoporous dopamine, or a combination of mesoporous silicon-mesoporous carbon.

[0065] In this embodiment, specifically, the mesoporous silica includes spheres, rods or tubes.

[0066] In this embodiment, specifically, the tumor targeting material is RNA, polypeptide, or protein.

[0067] In this embodiment, specifically, the method for preparing the nanomotor comprises the following steps:

[0068] preparing aggregation-induced emission molecules;

[0069] Asymmetric dual-mesoporous nanomaterials with different pore sizes were selected as the supporting materials for nanomotors;

[0070] Utilizing the different pore sizes of the asymmetric dual-mesoporous nanomaterials, the aggregation-induced emission molecule is selectively loaded in one of the pore sizes using a co-precipitation method or an adsorption method;

[0071] Modification of nanomotors with tumor-targeting materials.

[0072] In some embodiments, preferably, the method for preparing the nanomotor comprises the following steps:

[0073] The NDA-FT (1.0 mg) obtained in Example 1 and the amino-modified asymmetric dual mesoporous nanomaterial M&P (M: mesoporous silica spheres; P: mesoporous organic silica cubes) (10 mg) were uniformly mixed in THF (2.0 mL) and stirred. The above dispersion was quickly poured into 10 mL of deionized water. The mixture was magnetically stirred for 12 h and dialyzed in deionized water for 48 h to obtain a suspension of M&P-NFT particles.

[0074] M&P-NFT / R nanomotors were prepared by modifying M&P-NFT with DSPE-PEG-RGD (molecular weight: 2000Da). M&P-NFT was dispersed in 10mL of DSPE-PEG-RGD PBS solution. After stirring for 24h, the M&P-NFT / R nanomotors were obtained by centrifugation, washing and collecting.

[0075] Results: Figure 6-9 As shown, Figure 6 This is a transmission electron microscope image of the asymmetric dual-mesoporous nanomaterial M&P with different pore sizes in Example 2; Figure 7 Schematic diagram of the preparation of the nanomotor M&P-NFT / R of Example 2; Figure 8 This is a transmission electron microscope image of the nanomotor M&P-NFT / R of Example 2; Fig. 9 This is the absorption and emission spectra of the nanomotor M&P-NFT / R of Example 2 of the present invention; it can be seen that the motor has a maximum absorption peak at 808nm and has bright near-infrared II region emission.

[0076] Application Example 1

[0077] The self-thermophoresis behavior test of the M&P-NFT / R nanomotor obtained in Example 2 comprises the following steps:

[0078] Cy5.5-labeled M&P-NFT / R nanomotors were filled in borosilicate capillaries and sealed with paraffin to minimize drift effects. The capillaries filled with samples were placed on a glass slide with a thickness of 1.0 mm and their movement was observed under a fluorescence microscope with a 40x objective. The fluorescence microscope used an 808 nm laser system as an external excitation source, and a digital camera captured the movement video of the nanomotors.

[0079] result: Fig.10 This application example 1 contains the motion trajectories of the near-infrared self-thermophoretic mesoporous nanomotor M&P-NFT / R based on aggregation-induced emission molecules at different laser powers. It can be seen that with the increase of light power density, its motion behavior changes from typical Brownian motion to enhanced diffusion motion. This shows that the aggregation-induced emission molecules, as the driving unit of the nanomotor, can convert light into heat through their own photothermal conversion properties to drive the self-thermophoresis of the motor.

[0080] Application Example 2

[0081] The application of the M&P-NFT / R nanomotor obtained in Example 2 in tumor targeting imaging includes the following steps:

[0082] The near-infrared luminescent self-thermophoretic mesoporous nanomotors based on aggregation-induced emission molecules (2.0 mg / ml, 100 μL, NDA-FT equivalent of 2.8 nmol) were intravenously injected into the tail vein of nude mice, and NIR-II fluorescence images of the tumor were taken at different time points.

[0083] result: Fig.11 For example 2 of this application, the tumor-targeted imaging of the self-thermophoretic mesoporous nanomotor M&P-NFT / R based on near-infrared luminescence of aggregation-induced emission molecules is described. Fig.11 As shown, as time goes by, the fluorescence signal of the nanomotor at the tumor site gradually increases and reaches a peak at 36 hours, indicating effective accumulation and targeting of the tumor site. This shows that aggregation-induced emission molecules can be used as luminescent imaging units of nanomotors for tumor diagnosis.

[0084] Application Example 3

[0085] The application of the M&P-NFT / R nanomotor obtained in Example 2 in deep tumor penetration includes the following steps:

[0086] The near-infrared luminescent self-thermophoretic mesoporous nanomotors based on aggregation-induced emission molecules were intravenously injected into the tail vein of nude mice, and the tumor was irradiated with laser for 15 minutes 24 hours later. After the treatment, the tumor was removed, embedded in paraffin, and sectioned for relevant immunofluorescence staining.

[0087] Results: Fig.12 As shown, Fig.12 This application example 3 includes the test of the near-infrared luminescence self-thermophoretic mesoporous nanomotor M&P-NFT / R based on aggregation-induced luminescence molecules on the remodeling and penetration of the tumor interstitial microenvironment. As can be seen from the figure, under laser irradiation, the motor can destroy tumor interstitial cells and degrade tumor matrix components through photothermal action, and penetrate blood vessels and penetrate deep into the tumor under self-thermophoresis.

[0088] From the above examples, it can be seen that the aggregation-induced luminescence molecule of the present invention that emits near-infrared light and has photothermal properties has obvious aggregation-induced luminescence and stable near-infrared II region luminescence characteristics; the mesoporous nanomotor prepared therefrom has near-infrared II region luminescence, heat generation, and self-thermophoresis characteristics. Under near-infrared II region imaging, the tumor location can be reported, the tumor interstitial microenvironment can be reshaped under photothermal action, and combined with self-thermophoresis behavior, deep tumor penetration behavior can be achieved.

[0089] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the protection scope of the present invention.

Claims

1. An aggregation-induced emission molecule, characterized in that: The chemical structural formula of the aggregation-induced emission molecule is: Wherein, R is a group containing an alkyl chain.

2. The aggregation-induced emission molecule according to claim 1, characterized in that The alkyl chain is a straight chain having 1 to 20 carbon atoms, a branched chain having 1 to 20 carbon atoms, a cyclic alkyl chain having 1 to 20 carbon atoms, an alkyl chain in which carbon atoms are substituted by oxygen atoms, alkenyl groups, alkynyl groups, aryl groups, carbonyl groups, hydroxyl groups, amino groups, carboxyl groups, cyano groups, nitro groups or ester groups, and an alkyl chain in which hydrogen atoms are substituted by fluorine atoms, chlorine atoms, bromine atoms or iodine atoms.

3. The aggregation-induced emission molecule according to claim 2, characterized in that: The aggregation-induced emission molecule adopts thionaphthalene tetracarboxylic acid diimide with a long alkyl chain as an electron acceptor group and fluorenyl triphenylamine as a molecular rotor and an electron donor unit.

4. A nanomotor, characterized in that: The nanomotor comprises the aggregation-induced emission molecule, the asymmetric dual-mesoporous nanomaterial and the tumor targeting material as described in any one of claims 1 to 3.

5. The nanomotor according to claim 4, characterized in that: The asymmetric dual-mesoporous nanomaterial includes one of a combination of inorganic mesoporous silicon and organic mesoporous silicon, a combination of inorganic mesoporous silicon and inorganic mesoporous silicon, a combination of mesoporous silicon and mesoporous dopamine, or a combination of mesoporous silicon and mesoporous carbon.

6. The nanomotor according to claim 5, characterized in that: The mesoporous silicon includes spheres, rods or tubes.

7. The nanomotor according to claim 4, characterized in that: The mesopore diameter of the asymmetric double-mesoporous nanomaterial is 2-50nm.

8. The nanomotor according to claim 4, characterized in that: The tumor targeting material is RNA, polypeptide, or protein.

9. The method for preparing a nanomotor according to claim 4, characterized in that: The following steps are involved: preparing aggregation-induced emission molecules; Asymmetric dual-mesoporous nanomaterials with different pore sizes were selected as the supporting materials for nanomotors; Utilizing the different pore sizes of the asymmetric dual-mesoporous nanomaterials, the aggregation-induced emission molecule is selectively loaded in one of the pore sizes using a co-precipitation method or an adsorption method; Modification of nanomotors with tumor-targeting materials.

10. Application of the aggregation-induced emission molecule according to any one of claims 1 to 3, the nanomotor according to any one of claims 4 to 8, and the nanomotor obtained by the preparation method according to claim 9 in targeted fluorescence imaging of tumors in the near-infrared II zone and achieving deep tumor penetration.

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