CN113527257B - Indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye and preparation method and application thereof - Google Patents
Indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses an indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye and a preparation method and application thereof, wherein the chemical structure of the compound is shown as (I), 2-formyl-8-benzyloxy quinoline (II) is used as a starting material to perform Knoevenagel condensation reaction with iodinated 2,3, 3-trimethyl-1-propyl-3H-indole salt (III) to obtain an indolyl 8-hydroxyquinoline derivative (IV), and then the indolyl 8-hydroxyquinoline derivative shown as the formula (I) is obtained through boron tribromide debenzylation reaction. The compound has the advantages of simple preparation method, mild reaction conditions and simple and convenient operation, the maximum fluorescence emission wavelength of the compound in different solvents is more than 650nm, and the compound has large Stokes shift (more than 200 nm). In addition, the fluorescent probe has excellent cell permeability and biocompatibility, and can be used for near-infrared bioluminescence probes and bioluminescence imaging.
Description
Technical Field
The invention belongs to the technical field of organic small molecule synthesis and the field of near-infrared fluorescent dyes, and relates to a preparation method and application of an indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye.
Background
The benzindole derivatives are important nitrogen-containing organic heterocyclic compounds, have a large pi conjugated system, and have important applications in the aspects of biomedicine, biological detection, fluorescent dye and the like. 2,3, 3-trimethyl-1H-benzo [ e ] indole is an important intermediate for synthesizing a biological detection reagent indocyanine green. The indole cyanine dye has the characteristics of high photo-thermal stability, good solubility, larger molar extinction coefficient, large tunable range of maximum absorption wavelength and the like, and is widely applied to the fields of photographic sensitization, optical disc recording media, tumor detection, near-infrared fluorescent dye, photodynamic therapy, optical nonlinear materials, biomacromolecule fluorescent labeling and the like. However, the currently available indole near-infrared fluorescent dyes are still very limited, and many of the dyes fail to reach the near-infrared region and have the problems of poor light stability and the like.
8-hydroxyquinoline and its derivatives are a very important class of aromatic heterocyclic compounds, they are widely used in the field of fluorescent probes, the pi conjugated system makes it easy to generate electronic transition to generate fluorescence, the nitrogen atom on the heterocycle and the oxygen atom on the hydroxyl can also participate in the coordination reaction, and it is these characteristics that the quinoline derivatives can both recognize different ions and generate fluorescence. In addition, 8-hydroxyquinoline is widely used in pharmaceutical preparations such as neuroprotective agents, anticancer agents, enzyme inhibitors, metal protein chelators, anti-HIV drugs, antifungal drugs, etc., as an important class in pharmaceutical chemistry. Besides, the application of the compound in photoelectric functional molecular materials is also receiving more and more attention.
The invention designs and synthesizes the indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye from indole salt and 8-hydroxyquinoline compound. The 8-hydroxyquinoline group is used for carrying out functional modification on the iodinated indole group so as to increase the recognition group and increase the Stokes shift. The physical and chemical properties of the compound are improved, the increase of molecular mass is reduced as much as possible, and the advantages that small molecular compounds have small interference on biological tissues and cells and do not easily generate precipitates are reserved. The invention designs and develops the low molecular weight near-infrared fluorescent dye which is simple and novel and can be further modified, has better biocompatibility and cell membrane permeability, and has important significance in synthesis and application research.
Disclosure of Invention
The purpose of the invention is as follows: the invention aims to provide a preparation method and application of indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye.
The technical scheme is as follows: in order to achieve the purpose of the invention, the invention adopts the technical scheme that:
the invention relates to an indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye which has the following structure:
the invention relates to a synthetic route of an indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye, which comprises the following steps:
the invention relates to a preparation process of an indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye, which comprises the following steps:
step 1: dissolving 2-formyl-8-benzyloxy quinoline (II) and 2,3, 3-trimethyl-1-propyl-3H-indole iodide (III) in absolute ethyl alcohol, dropwise adding piperidine into the solution, and carrying out reflux reaction for 12H at the temperature of 80 ℃ under the argon atmosphere. Cooling to room temperature after the reaction is finished, filtering to remove filtrate to obtain dark red solid, and separating and purifying by silica gel column chromatography to obtain the indolyl 8-hydroxyquinoline derivative (IV);
and 2, step: dissolving the indolyl 8-hydroxyquinoline derivative (IV) in dry dichloromethane, slowly and dropwise adding boron tribromide under the condition of ice bath cooling under the protection of argon, stirring for 15min, removing the ice bath, slowly heating to room temperature, and stirring for reaction for 6 h. After the reaction is finished, the reaction solution is placed in an ice bath to be cooled and quenched by water, dichloromethane is used for extraction, organic phases are combined and washed by saturated saline solution, then the organic phases are dried and filtered by anhydrous sodium sulfate, and after the solvent is dried by spinning, the crude product is separated by silica gel column chromatography to obtain the indolyl 8-hydroxyquinoline near infrared fluorescent dye (I).
In the above reaction step 1, the mass ratio of the 2-formyl-8-benzyloxyquinoline (II) and the 2,3, 3-trimethyl-1-propyl-3H-indole iodide salt (III) was 1: 1;
in the reaction step 1, the dosage of the catalyst piperidine is 5-10% of the amount of the reactant raw material substances;
in the above reaction step 2, the mass ratio of the indole 8-quinolinol derivative (IV) to the boron tribromide is 1: 10.
The invention has the beneficial effects that:
compared with the prior art, the indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye and the preparation method thereof have the advantages that: (1) the indolyl conjugated 8-hydroxyquinoline near infrared fluorescent dye has obvious solvent effect, the maximum fluorescence emission wavelength is over 650nm, and the Stokes shift is large; (2) the probe can be used for HeLa cell fluorescence imaging research, has better cell permeability and biocompatibility, and can be used as a near-infrared biological fluorescence probe and biological fluorescence imaging; (3) the method has the advantages of simple synthetic route, mild reaction conditions, good reaction selectivity, simple separation method and universality, and can be popularized and applied to the synthesis of similar near-infrared fluorescent dyes.
Drawings
FIG. 1 shows UV-VIS absorption spectra of indolyl conjugated 8-hydroxyquinoline near-IR fluorescent dye (I) in different solvents;
FIG. 2 is a fluorescence emission spectrum of an indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye (I) in different solvents;
FIG. 3 is a laser confocal fluorescence imaging diagram of the indole-conjugated 8-hydroxyquinoline near-infrared fluorescent dye (I) of the present invention incubated with HeLa cells.
Detailed Description
The present invention is further explained below with reference to specific examples, which are not intended to limit the present invention in any way.
Ultraviolet-visible and fluorescence spectra were used to characterize the structure of the compounds and to study the photophysical properties of the compounds. The detection instrument is as follows: shimadzu UV-3100 UV-visible spectrophotometer (scanning range 300-900 nm, light path slit 2nm) and fluorescence spectra were measured with an American Amico Bowman Series 2 Luminescence Spectrometer.
Example 1
2-formyl-8-benzyloxyquinoline (II) (265mg, 1mmol) and 2,3, 3-trimethyl-1-propyl-3H-indole iodide (III) (330mg, 1mmol) were dissolved in 15mL of anhydrous ethanol, 50. mu.L of piperidine was added dropwise to the solution, and the reaction was refluxed under an argon atmosphere for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the filtrate was removed by filtration to give a dark red solid, which was isolated and purified by silica gel column chromatography using methylene chloride-methanol (v: v ═ 20: 1) as an eluent to give indole 8-quinolinol derivative (IV) in 74% yield. 1 H-NMR(600MHz，CDCl 3 ，ppm)：δ＝8.94(d，J＝8.4Hz，1H)，8.67(d，J＝16.2Hz，1H)，8.43(d，J＝16.2Hz，1H)，8.37(d，J＝8.4Hz，1H)，7.71-7.70(m，1H)，7.64-7.61(m，3H)，7.58(d，J＝7.8Hz，2H)，7.53(t，J＝7.8Hz，1H)，7.48-7.43(m，3H)，7.39(t，J＝7.2Hz，1H)，7.16(d，J＝7.2Hz，1H)，5.40(s，2H)，5.00(t，J＝7.2Hz，2H)，2.04(q，J＝7.2Hz，2H)，1.97(s，6H)，1.03(t，J＝7.8Hz，3H).
Example 2
Dissolving indolyl 8-hydroxyquinoline derivative (IV) (114.8mg, 0.2mmol) in 30mL dry dichloromethane, slowly adding boron tribromide (0.19mL, 2mmol) dropwise under the condition of ice bath under the protection of argon, stirring for 15min, removing the ice bath, slowly raising the temperature to room temperature, and stirring for reaction for 6 h. After the reaction is finished, the reaction solution is placed in an ice bath to be cooled and quenched by water, dichloromethane is used for extraction, saturated saline solution is used for washing, an organic phase is dried and filtered by anhydrous sodium sulfate, the solvent is dried, and separation and purification are carried out by silica gel column chromatography by using dichloromethane-methanol (v: v ═ 40: 1) as an eluent, so that the indolyl 8-hydroxyquinoline near infrared fluorescent dye (I) is obtained, and the yield is 76%. 1 H-NMR(600MHz，CDCl 3 ，ppm)：δ＝9.08(s，1H)，8.79(d，J＝15.6Hz，1H)，8.572-8.514(m，2H)，8.14(d，J＝7.8Hz，1H)，7.68(s，1H)，7.59-7.56(m，3H)，7.39(t，J＝7.8Hz，1H)，7.20(d，J＝7.2Hz，1H)，7.02(d，J＝7.2Hz，1H)，3.41(s，1H)，2.03(d，J＝6.6Hz，2H)，1.91(s，6H)，1.05(t，J＝7.2Hz，3H).
Example 3 UV-VISIBLE ABSORPTION SPECTRUM OF INDOLE-CONJUGATED 8-HYDROXYQUINOLINE NIR FLUORESCENT DYE (I) IN VARIOUS SOLVENTS
Dissolving indolyl conjugated 8-hydroxyquinoline near infrared fluorescent dye (I) in dichloromethane, ethyl acetate and methanol respectively to obtain solution with concentration of 1 × 10 -5 The UV-VIS absorption spectrum of the solution is measured in mol/L. FIG. 1 shows the UV-VIS absorption spectra of fluorescent dye (I) prepared in example 2 of the present invention in different solvents.
EXAMPLE 4 fluorescence of indolyl conjugated 8-hydroxyquinoline near Infrared fluorescent dye (I) in different solvents
Dissolving indolyl conjugated 8-hydroxyquinoline near infrared fluorescent dye (I) in dichloromethane, ethyl acetate and methanol respectively to obtain solution with concentration of 1 × 10 -5 And measuring the fluorescence emission spectrum of the solution in mol/L. FIG. 2 shows fluorescence spectra of fluorescent dye (I) prepared in example 2 of the present invention in different solvents.
EXAMPLE 5 indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye (I) for tumor cell fluorescence imaging
Incubating the indolyl conjugated 8-hydroxyquinoline near infrared fluorescent dye (I) and HeLa cells together, and observing an imaging photo of the HeLa cells under a confocal fluorescent microscope. FIG. 3 is a confocal fluorescence imaging photograph of laser after incubation of HeLa cells and fluorescent dye (I). The excitation wavelength of Hoechst 33342 is 352 nm; the excitation wavelength of mHoney Dew is 487 nm; merged is the superposition state. After adding the fluorescent dye (I) into the HeLa cells for incubation together, the fluorescent dye enters the HeLa cells for clear imaging. The indolyl conjugated 8-hydroxyquinoline near infrared fluorescent dye (I) can be used for biological cell imaging.
Claims (4)
1. A preparation method of indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye is characterized in that the chemical structure of the indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye is shown as (I):
the preparation method of the indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye comprises the following steps: taking 2-formyl-8-benzyloxy quinoline (II) as a starting material to perform Knoevenagel condensation reaction with 2,3, 3-trimethyl-1-propyl-3H-indole iodide (III) to obtain an indolyl 8-hydroxyquinoline derivative (IV), and then performing boron tribromide debenzylation reaction to obtain the indolyl 8-hydroxyquinoline near-infrared fluorescent dye shown in the formula (I);
2. the method of claim 1, comprising the steps of:
step 1: dissolving 2-formyl-8-benzyloxy quinoline (II) and 2,3, 3-trimethyl-1-propyl-3H-indole iodide (III) in absolute ethyl alcohol, dropwise adding piperidine into the solution, and carrying out reflux reaction for 12H at the temperature of 80 ℃ under the argon atmosphere; cooling to room temperature after the reaction is finished, filtering to remove filtrate to obtain dark red solid, and separating and purifying by silica gel column chromatography to obtain the indolyl 8-hydroxyquinoline derivative (IV);
step 2: dissolving indolyl 8-hydroxyquinoline derivative (IV) in dry dichloromethane, slowly dripping boron tribromide under the condition of ice bath under the protection of argon, stirring for 15min, removing the ice bath, slowly heating to room temperature, and stirring for reaction for 6 h; and after the reaction is finished, cooling the reaction solution in an ice bath, quenching the reaction solution by using water, extracting the reaction solution by using dichloromethane, washing combined organic phases by using saturated saline solution, drying and filtering the organic phases by using anhydrous sodium sulfate, removing the solvent, and separating and purifying the organic phases by using silica gel column chromatography to obtain the indolyl conjugated 8-hydroxyquinoline near-infrared fluorescent dye (I).
3. The process according to claim 2, wherein in the step 1, the ratio of the amounts of the 2-formyl-8-benzyloxyquinoline (II) and the 2,3, 3-trimethyl-1-propyl-3H-indole iodide (III) is 1:1, the dosage of the catalyst piperidine is 5-10% of the amount of the reactant raw material substances.
4. The production method according to claim 2, characterized in that in the step 2, the mass ratio of the indole 8-quinolinol derivative (IV) to the boron tribromide (V) is 1: 10.
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