CN113105441A - Compound with aggregation-induced emission property and application thereof in field of surgical navigation - Google Patents
Compound with aggregation-induced emission property and application thereof in field of surgical navigation Download PDFInfo
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- CN113105441A CN113105441A CN202110408049.0A CN202110408049A CN113105441A CN 113105441 A CN113105441 A CN 113105441A CN 202110408049 A CN202110408049 A CN 202110408049A CN 113105441 A CN113105441 A CN 113105441A
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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Abstract
The invention belongs to the technical field of synthesis of compounds with aggregation-induced emission properties, and relates to a compound with aggregation-induced emission properties and application thereof. The beneficial effects are that: 1. a new idea of surgical navigation is provided; 2. the material is easy to obtain, the cost is low, and the preparation is easy; 3. the biological toxicity is low; 4. the luminous wavelength is long, the interference by background fluorescence is small, and the tissue penetrability is strong.
Description
Technical Field
The invention belongs to the technical field of synthesis of compounds with aggregation-induced emission properties, and relates to a compound with aggregation-induced emission properties and application thereof.
Background
The barbituric acid compound can be used as a polymerization catalyst, a raw material for preparing dye, an intermediate for synthesizing common medicines such as vitamin B12 and the like, and the barbituric acid derivative is a long-acting nerve medicine which is applied clinically earlier. Because of the advantages of little biological toxic and side effect, slow action, long maintenance time and the like of barbiturates, the barbiturates are usually used for sedation, hypnosis, anticonvulsion and anti-epilepsy in clinic and can also be used for pre-anesthesia administration. At present, few examples exist for synthesizing long-wavelength emission AIE molecules by using groups with biological activity as electron donors (or acceptors), the work successfully utilizes a low-cost biological active substance barbituric acid to achieve the purpose of red shift of the luminous wavelength of the AIE molecules by conjugated connection with AIE units, and the synthesis is simple, the cost is low, and the target molecules have excellent performance and can be effectively applied to fluorescence navigation of in-vivo tumor resection operations.
The design of the patent synthesizes 2 fluorescent dyes based on 1, 3-diethyl thiobarbituric acid as an electron-withdrawing group, enriches the AIE family, provides a brand-new thought for molecular design, and simultaneously provides a new application of the fluorescent dyes in treating related diseases so as to solve the problems in the prior art.
Disclosure of Invention
One of the purposes of the invention is to design and synthesize 2 kinds of fluorescent dyes based on 1, 3-diethyl thiobarbituric acid as an electron-withdrawing group, thereby enriching the AIE family; the second object provides a new use of the compound.
The invention discloses a compound with aggregation-induced emission properties, which has a molecular structure shown in a general formula (I):
or at least one of derivatives, salts, hydrates, chelates and polymers thereof, wherein n is a natural number, and X is O or S;
the R is1The group includes the following structure:
the R is2、R3The group includes the following structure:
at least one of them.
The aim of the design is to adopt the design idea of 'D-pi-A', tetraphenylethylene with a highly distorted three-dimensional structure is used as a donor unit, and thiophene is further inserted into the molecular structure of the tetraphenylethylene to obtain stronger conjugation and redder emission, so that a series of AIE molecules with simple synthesis and gradually red-shifted absorption and emission wavelengths are synthesized. In order to obtain a fluorescent dye with a lower energy gap, the emission wavelength of the fluorescent dye is red-shifted to a far-red/near-infrared region so as to be suitable for surgical navigation. The S atom of the VIB A group is selected to replace the O atom in the 1, 3-diethyl barbituric acid, compared with the molecule taking the diethyl barbituric acid as a donor unit, the synthesized fluorescent dye taking the 1, 3-diethyl thiobarbituric acid as an electron-withdrawing group has the maximum red-shifted emission wavelength, namely, the fluorescent dye has more excellent optical penetration, less light damage and lower light scattering, and is more suitable for the research in the field of biological imaging.
Preferably, the R2 group and the R3 group are the same group.
Preferably, the value of n ranges from 6 to 12, and more preferably ranges from 8 to 10.
Preferably, the compound having aggregation-induced emission properties adopts a molecular structure as shown below:
or at least one of derivatives, salts, hydrates, chelates and polymers thereof.
The invention also discloses application of the compound with the aggregation-induced emission property as a surgical navigation marking reagent.
Preferably, the compound with aggregation-induced emission properties is used as a tumor surgery navigation marker reagent.
The invention also discloses a surgical navigation marking reagent composition which comprises the compound with the aggregation-induced emission property.
The invention has the beneficial effects that:
1. a new idea of surgical navigation is provided;
2. the material is easy to obtain, the cost is low, and the preparation is easy;
3. the biological toxicity is low;
4. the luminous wavelength is long, the interference by background fluorescence is small, and the tissue penetrability is strong.
Drawings
FIG. 1 is the H nuclear magnetic spectrum of compound B8;
FIG. 2 is the H nuclear magnetic spectrum of compound B11;
FIG. 3 is a H NMR spectrum of Compound B5;
FIG. 4 is a H NMR spectrum of Compound A1;
FIG. 5 is the H NMR spectrum of Compound A2;
FIG. 6 is a C NMR spectrum of Compound A1;
FIG. 7 is the C NMR spectrum of Compound A2;
FIG. 8 shows UV absorption spectra of Compound A1 (FIG. A) and Compound A2 (FIG. B) in different organic solvents;
FIG. 9 shows fluorescence emission spectra of Compound A1 (FIG. A) and Compound A2 (FIG. B) in different organic solvents;
FIG. 10 is a normalized fluorescence emission spectrum of Compound A1 (Panel A) in THF/water mixed solution at different volume ratios; normalized fluorescence emission spectra of compound a2 (panel B) in THF/water mixed solution at different volume ratios; graph of aggregation induced luminescence curves (panel C) for compound a1 and compound a2 (I0 is the fluorescence intensity at 10% water volume);
FIG. 11 is a graph of the distribution of the optimized structures, Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) for Compound A1 and Compound A2;
FIG. 12 is the dynamic light scattering Diameter (DLS) for Compound A1 NPs (Panel A) and Compound A2 NPs (Panel B); inset is a Transmission Electron Micrograph (TEM) of the corresponding nanoparticle;
FIG. 13 is a diagram of the cell activity assay (MTT method) for Compound A1 and Compound A2;
FIG. 14 is a Confocal Laser Scanning Microscope (CLSM) image of 4T1 breast cancer cells incubated with Compound A2 NPs for 4h, with DAPI (blue) staining of the nuclei;
FIG. 15 is a graph of bioluminescence and fluorescence visualization of the abdominal cavity of mice before tumor resection (Panel A); fluorescence image guided abdominal fluorescence image before and after resection and tumor nodule fluorescence imaging (figure B); bioluminescence images of tumor nodules excised from the unguided and compound a2 NPs-guided groups (panel C).
Detailed Description
The following examples are given to illustrate the technical examples of the present invention more clearly and should not be construed as limiting the scope of the present invention.
Example 1
The synthetic route of compound a1(TTO) is as follows:
a method for preparing compound a1 having aggregation-induced emission properties, comprising the steps of:
step one, synthesis of compound B3. Compound B1 (bromotetraphenylethylene, 820mg, 2mmol), compound B2 (pinacol diborate, 762mg, 3mmol), potassium acetate (588mg, 6mmol) and Pd (dppf)2Cl2(87mg, 0.12mmol) were dissolved in a toluene solution (10mL) under a nitrogen atmosphere, placed in a 25mL reaction flask, and reacted for 12h under reflux. After the reaction is finished, cooling to room temperature, and removing the reaction solvent by reduced pressure distillation to obtain a crude product. Separating and purifying by column chromatography (eluent ratio is petroleum ether: ethyl acetate 10: 1) to obtain product compound B3(900mg, yield 98.3%)
Step two, synthesis of compound B5. Compound B3(900mg, 2mmol), compound B4 (5-bromothiophene-2-carbaldehyde, 573mg, 3mmol), tetrabutylammonium bromide (TBAB, 65mg, 0.2mmol) and tetratriphenylphosphine palladium (Pd (PPh4)3, 47mg, 0.04mmol) were dissolved in 10mL of a toluene solvent under a nitrogen atmosphere, placed in a 50mL reaction flask, 6mL of a 2M concentration potassium carbonate solvent (1.65g K2CO3, 6mL of ddH2O) was added, and reacted for 12 hours under reflux. After the reaction, the aqueous phase was extracted with ethyl acetate (15mL × 3), and the reaction solvent was removed by distillation under reduced pressure to obtain a crude product. The eluent ratio by column chromatography is petroleum ether: ethyl acetate ═ 8: 1) isolation and purification gave the product, Compound B5(850mg, 96.15% yield).
Step three, synthesizing a compound B8. Compound B6 (malonic acid, 208mg, 2mmol) and compound B7(1, 3-diethylurea, 232mg, 2mmol) were dissolved in 2mL of glacial acetic acid and placed in a 25mL reaction flask, after heating to 60 ℃, 2mL of acetic anhydride was added and reacted for 6 h. Then, 1mL of ultrapure water was added thereto, and the reaction was heated to 70 ℃ for 0.5 hour. After the reaction was completed, the reaction was cooled to room temperature, extracted with ethyl acetate (10mL × 3) to obtain an organic phase, and the solvent was removed by distillation under reduced pressure to obtain a crude product. Separation and purification by column chromatography (eluent ratio petroleum ether: ethyl acetate: 2: 1) gave the product compound B8(360mg, 97% yield).
Step four, synthesizing a compound A1. Compound B5(226mg, 0.6mmol) and compound B8(120mg, 0.66mmol) were dissolved in 6mL of acetonitrile under a nitrogen atmosphere, 2 drops of piperidine were added dropwise, and the mixture was reacted at reflux temperature for 8 h. After the reaction was complete, the reaction was cooled to room temperature, filtered, and washed to give an orange-red solid (350mg, 96% yield).
Example 2
The synthesis route of compound A2(TTS) is as follows:
compared with example 1, the present example is different only in the third and fourth steps.
The method comprises the following specific steps:
step one, synthesis of compound B3. Compound B1 (bromotetraphenylethylene, 820mg, 2mmol), compound B2 (pinacol diborate, 762mg, 3mmol), potassium acetate (588mg, 6mmol) and Pd (dppf)2Cl2(87mg, 0.12mmol) were dissolved in a toluene solution (10mL) under a nitrogen atmosphere, placed in a 25mL reaction flask, and reacted for 12h under reflux. After the reaction is finished, cooling to room temperature, and removing the reaction solvent by reduced pressure distillation to obtain a crude product. Separating and purifying by column chromatography (eluent ratio is petroleum ether: ethyl acetate 10: 1) to obtain product compound B3(900mg, yield 98.3%)
Step two, synthesis of compound B5. Compound B3(900mg, 2mmol), compound B4 (5-bromothiophene-2-carbaldehyde, 573mg, 3mmol), tetrabutylammonium bromide (TBAB, 65mg, 0.2mmol) and tetratriphenylphosphine palladium (Pd (PPh4)3, 47mg, 0.04mmol) were dissolved in 10mL of a toluene solvent under a nitrogen atmosphere, placed in a 50mL reaction flask, 6mL of a 2M concentration potassium carbonate solvent (1.65g K2CO3, 6mL of ddH2O) was added, and reacted for 12 hours under reflux. After the reaction, the aqueous phase was extracted with ethyl acetate (15mL × 3), and the reaction solvent was removed by distillation under reduced pressure to obtain a crude product. The eluent ratio by column chromatography is petroleum ether: ethyl acetate ═ 8: 1) isolation and purification gave the product, Compound B5(850mg, 96.15% yield).
Step three, synthesizing a compound B11. Dissolving compound B10 (diethyl malonate, 264mg, 2mmol) and compound B9(1, 3 diethyl thiourea, 264mg, 2mmol) in 2mL of glacial acetic acid, placing in a 25mL reaction flask, heating to 70 ℃, adding 1mL of acetic anhydride, and reacting for 13 h. After 13h, the temperature was raised to reflux temperature and the reaction was continued for 1 h. After the reaction is finished, the reaction solvent is removed by reduced pressure distillation to obtain a crude product. Separation and purification by column chromatography (eluent ratio petroleum ether: ethyl acetate: 2: 1) gave compound B11(360mg, 96% yield).
Step four, synthesizing a compound A2. Compound B5(200mg, 0.46mmol) and compound B11(100mg, 0.5mmol) were dissolved in 6mL of acetonitrile under a nitrogen atmosphere, 2 drops of piperidine were added dropwise, and the mixture was reacted at reflux temperature for 8 h. After the reaction was completed, the reaction was cooled to room temperature, filtered, and washed to obtain a red solid (285mg, yield 95%).
To demonstrate the success of the synthetic route described in example 1-2, compound (A1) and compound (A2) were tested as follows:
as shown in FIG. 1, the nuclear magnetic absorption peaks of compound B8 are as follows:1H NMR(400MHz,Chloroform-d)δ3.95(q,J＝7.1Hz,4H),3.65(s,2H),1.22(t,J＝7.1Hz,1H).
as shown in FIG. 2, the nuclear magnetic absorption peaks of compound B11 are as follows:1H NMR(400MHz,Chloroform-d)δ4.55(dq,J＝12.0,7.0Hz,1H),2.74(s,0H),1.30(dt,J＝10.4,7.0Hz,1H).
as shown in FIG. 3, the nuclear magnetic absorption peaks of Compound B5 are as follows:1H NMR(400MHz,Chloroform-d)δ9.87(s,1H),7.71(d,J＝4.0Hz,1H),7.43(d,J＝8.4Hz,2H),7.35(d,J＝4.0Hz,1H),7.16–7.10(m,10H),7.09–7.00(m,7H).
as shown in FIG. 4, the H nuclear magnetic absorption peaks of Compound A1 are as follows:1H NMR(400MHz,Chloroform-d)δ8.64(s,1H),7.82(d,J＝4.2Hz,1H),7.54(d,J＝8.4Hz,2H),7.44(d,J＝4.2Hz,1H),7.16–7.10(m,10H),7.08–7.03(m,7H),4.11–4.03(m,4H),1.32–1.24(m,6H).
as shown in FIG. 5, the H nuclear magnetic absorption peaks of Compound A2 are as follows:1H NMR(400MHz,Chloroform-d)δ8.30(d,J＝15.2Hz,1H),8.11(d,J＝15.2Hz,1H),7.41–7.36(m,3H),7.27(s,1H),7.14–7.09(m,9H),7.08–7.00(m,7H),4.60–4.51(m,4H),1.31(tt,J＝8.0,4.0Hz,6H).
as shown in FIG. 6, the C nuclear magnetic absorption peaks of Compound A1 are as follows:13C NMR(101MHz,CDCl3)δ162.45,161.63,160.22,150.61,148.46,146.76,145.81,143.43,143.25,142.21,140.02,136.13,132.20,131.43,131.34,131.10,127.96,127.89,127.74,126.93,126.78,126.73,126.06,124.36,109.76,37.49,36.73,13.50,13.41.
as shown in FIG. 7, the C nuclear magnetic absorption peaks of Compound A2 are as follows:13C NMR(101MHz,CDCl3)δ182.95,176.13,166.81,157.99,149.82,143.79,142.45,142.29,140.91,139.04,138.74,138.61,134.09,131.08,130.37,130.29,126.87,126.79,126.66,125.77,125.66,125.60,124.29,123.45,117.76,42.45,42.09,13.09.
application example 1
Example 2 was selected as the synthetic compound a2 as a surgical navigation agent.
In order to further illustrate the beneficial effects of the present invention, the following tests were specifically set up:
optical property testing
As shown in fig. 8, it can be seen that compound a1 and compound a2 both have significant uv absorption peaks in different organic solvents.
As shown in FIG. 9, it can be seen that both Compound A1 and Compound A2 are capable of emitting fluorescence in different organic solvents.
As shown in the attached FIG. 10, the attached FIGS. 10(A) and 10(B) show that the compound A1 and the compound A2 can emit fluorescence under THF/water mixed solution with different volume ratios, and prove that the composition comprising the compound A1 and/or the compound A2 can also be used as a surgical navigation indicator reagent;
the aggregation-induced emission curve in FIG. 10(C) shows: firstly, both the compound A1 and the compound A2 have aggregation-induced emission properties; secondly, the performance of compound A2 is superior to that of compound A1, and this change is due to the substitution of S for O.
As shown in FIG. 13, it was demonstrated that Compound A1 and Compound A2 possess cellular activity.
As shown in fig. 14, compound a2 was able to stain on a cellular scale.
As shown in fig. 15, compound a2 was able to stain on a macroscopic tissue scale, enabling surgical navigation.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (8)
1. A compound having an aggregation-induced emission property, characterized by having a molecular structure represented by the general formula (I):
or at least one of derivatives, salts, hydrates, chelates and polymers thereof,
wherein n is a natural number, and X adopts O or S;
the R is1The group includes the following structure:
the R is2、R3The group includes the following structure:
at least one of them.
2. The compound having aggregation-induced emission properties of claim 1, wherein R is2Group and said R3The same groups are used for the groups.
3. The compound having aggregation-induced emission properties according to claim 1, wherein n is in the range of 6 to 12.
4. The compound having aggregation-induced emission properties according to claim 1, wherein n is in the range of 8 to 10.
5. The compound having aggregation-induced emission properties according to claim 1, having a molecular structure as shown below:
or at least one of derivatives, salts, hydrates, chelates and polymers thereof.
6. Use of a compound having aggregation-induced emission properties according to any one of claims 1 to 5 as a surgical navigational marking agent.
7. The compound having an aggregation-induced emission property according to any one of claims 1 to 5 for use in a tumor surgery navigation marker reagent.
8. A surgical navigational marking reagent composition comprising a compound having aggregation-induced emission properties according to any of claims 1 to 5.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104877666A (en) * | 2013-12-19 | 2015-09-02 | 香港科技大学深圳研究院 | Luminescent material having aggregation-induced emission, method of making and application thereof |
| CN110818646A (en) * | 2019-11-18 | 2020-02-21 | 温州医科大学 | Aggregation-induced emission-based small-molecule fluorescent probe and preparation method and application thereof |
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2021
- 2021-04-15 CN CN202110408049.0A patent/CN113105441A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104877666A (en) * | 2013-12-19 | 2015-09-02 | 香港科技大学深圳研究院 | Luminescent material having aggregation-induced emission, method of making and application thereof |
| CN110818646A (en) * | 2019-11-18 | 2020-02-21 | 温州医科大学 | Aggregation-induced emission-based small-molecule fluorescent probe and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| HEQI GAO ET AL.: "Far-Red/Near-Infrared Emissive (1,3-Dimethyl)barbituric Acid-Based AIEgens for High-Contrast Detection of Metastatic Tumors in the Lung", 《CHEM. ASIAN J》 * |
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