CN115215839A - Indolyl benzimidazole near-infrared fluorescent dye and preparation method and application thereof - Google Patents
Indolyl benzimidazole near-infrared fluorescent dye and preparation method and application thereof Download PDFInfo
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- CN115215839A CN115215839A CN202211002474.0A CN202211002474A CN115215839A CN 115215839 A CN115215839 A CN 115215839A CN 202211002474 A CN202211002474 A CN 202211002474A CN 115215839 A CN115215839 A CN 115215839A
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/645—Specially adapted constructive features of fluorimeters
- G01N21/6456—Spatial resolved fluorescence measurements; Imaging
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- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
Abstract
The invention discloses an indolyl benzimidazole near-infrared fluorescent dye and a preparation method and application thereof, wherein the indolyl benzimidazole derivative shown in the formula (I) is obtained by carrying out Knoevenagel condensation reaction on a 4-benzimidazole-vinyl benzaldehyde derivative (II) and an iodinated 2,3,3-trimethyl-1-propyl-3H-indole salt (III). The indole benzimidazole near-infrared fluorescent dye has the advantages of simple preparation method, mild reaction conditions and high yield, has a remarkable solvent effect, has the maximum emission wavelength of about 680nm in a dimethyl sulfoxide solvent, and has large Stokes shift (more than 200 nm). In addition, the indolyl benzimidazole near infrared fluorescent dye has excellent cell permeability and biocompatibility, and has good application prospect in numerous fields of biological tissue dyeing, biological probes, fluorescence imaging and the like.
Description
Technical Field
The invention belongs to the field of fine organic synthesis and near-infrared fluorescent dyes, and relates to a preparation method and application of an indolyl benzimidazole near-infrared fluorescent dye.
Background
Benzoxazole compounds are a common class of benzoheterocyclesA compound is provided. Due to the special structure, the compound has excellent biological activity and reactivity, and therefore, the compound is widely applied to a plurality of fields. The benzimidazole compound has an electron-rich conjugated system and good luminescence property, and meanwhile, the nitrogen-containing heterocyclic compound causes the benzimidazole compound to have good biological activity; the fluorescent probe can be used as a chromophore of a fluorescent probe and is often applied to the aspects of optics, medicines, biological research and the like. Benzimidazole can also be used as an electron pair donor to coordinate with metal to form a complex and applied to CO 2 The chemical fixation, ion detection, biological imaging, fluorescent probe and other fields. In addition, 1,2-disubstituted benzimidazoles are often chosen as electron transport units for use in OLED materials. Benzimidazole compounds containing various substituents have been demonstrated to have significant antiviral, antitumor, antihypertensive, antidiabetic, anti-HIV and excellent antifungal and antibacterial effects. However, most of the benzimidazole fluorescent dyes applied to the market are located in an ultraviolet-visible light region, the most suitable excitation wavelength of the benzimidazole fluorescent dyes is mostly located below 600nm, and if the excitation wavelength can be increased to above 600nm, the problem of self background interference of biological tissues can be eliminated to a certain extent, the sensitivity of a biological detection technology can be improved better, and the application of fluorescent dye molecules in the biological field is further promoted.
Indoles, also known as azaindenes or benzopyrroles, are fused together from benzene and pyrrole sharing two carbon atoms. The C-2 and C-3 electron clouds have high density and show strong nucleophilic ability, and as a structural skeleton of a typical small molecular chemical drug, the indole compound occupies a place in the drugs in a plurality of treatment fields such as anti-tumor, anti-hypertension, anti-proliferation, anti-virus, analgesic, anti-inflammatory and antibacterial fields by virtue of wide biological activity, and more than one hundred drug molecules on the market at present. At present, the derivatization of indole compounds is to carry out functional group modification and dearomatization reaction around an indole skeleton under the condition of not changing a parent nucleus, and to manufacture a new molecule by bond breaking and recombination change of the indole skeleton structure. 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 photo-thermal stability and the like.
The invention designs and synthesizes an indolyl benzimidazole near-infrared fluorescent dye by taking indole salt and 4-benzimidazole vinylbenzaldehyde derivatives as raw materials. The benzimidazole and the indole group form conjugation, and the molecular conjugation system is increased, so that the delocalization of the electron cloud of the molecular system is promoted, the HOMO-LUMO energy level of the molecule is reduced, and the overall optical performance of the molecule is improved. The fluorescent dye has excellent biocompatibility, good cell membrane permeability, good stability in organisms, good fluorescence performance and good application prospect in a plurality of fields such as biological tissue staining, biological probes, fluorescence imaging and the like.
Disclosure of Invention
The purpose of the invention is as follows: the invention aims to provide a preparation method and application of an indolyl benzimidazole near-infrared fluorescent dye.
The technical scheme is as follows: in order to achieve the purpose of the invention, the technical scheme adopted by the invention is as follows:
the structure of the indolyl benzimidazole near infrared fluorescent dye related by the invention is as follows:
the invention relates to a synthetic route of an indolyl benzimidazole near-infrared fluorescent dye, which comprises the following steps:
the invention relates to a preparation process of an indolyl benzimidazole near-infrared fluorescent dye, which comprises the following steps:
4-benzimidazole vinyl benzaldehyde derivative (II) and 2,3,3-trimethyl-1-propyl-3H-indole salt (III) iodide are dissolved in absolute ethyl alcohol, piperidine is added into the solution dropwise, and reflux reaction is carried out for 12 hours at 80 ℃ under the protection of argon. And (3) cooling to room temperature after the reaction is finished, filtering to remove the filtrate to obtain a dark red solid, and separating and purifying by silica gel column chromatography to obtain the indolyl benzimidazole near-infrared fluorescent dye (I).
In the above reaction step, the mass ratio of the 4-benzimidazolethylbenzaldehyde derivative (II) to the 2,3,3-trimethyl-1-propyl-3H-indolyl iodide (III) was 1: 1.
The invention has the beneficial effects that:
compared with the prior art, the indolyl benzimidazole near-infrared fluorescent dye and the preparation method thereof have the advantages that: (1) The indolyl benzimidazole near infrared fluorescent dye has obvious solvent effect, the maximum fluorescence emission wavelength in dimethyl sulfoxide solvent is about 680nm, and the indolyl benzimidazole near infrared fluorescent dye has large Stokes shift (more than 200 nm); (2) The cell permeability and biocompatibility are good, and the fluorescent imaging method can be used for HeLa cell fluorescent imaging; (3) The synthesis method is simple, the reaction condition is mild, the reaction selectivity is good, the separation method is simple and easy, the universality is realized, and the method can be popularized and applied to the synthesis of similar near-infrared fluorescent dyes.
Drawings
FIG. 1 is a diagram of the UV-VIS absorption spectra of an indolylbenzimidazole near-IR fluorescent dye (I) in different solvents;
FIG. 2 is a fluorescence emission spectrum of the near infrared fluorescent dye (I) of the indolylbenzimidazole in different solvents;
FIG. 3 is a laser confocal fluorescence imaging diagram of the indolylbenzimidazole near-infrared fluorescent dye (I) 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.
The structure of the compound is characterized by a high-resolution mass spectrometer, an ultraviolet-visible spectrum and a fluorescence spectrum, and the photophysical properties of the compound are researched. The detection instrument is as follows: the U.S. Thermo electro fluorescence CORPORATION high resolution mass spectrometry workstation, shimadzu UV-3100 model UV-visible spectrophotometer (scan range 300-900 nm, optical path slit 2 nm), fluorescence spectra were tested using the U.S. Amico Bowman Series 2 Luminescence Spectrometer. The fluorescence co-aggregation microscope for cell imaging was Olympus FV3000, japan.
Example 1
4-Benzimidazovinylbenzaldehyde derivative (II) (248mg, 1mmol) and 2,3,3-trimethyl-1-propyl-3H-indole iodide salt (III) (330mg, 1mmol) were dissolved in 15mL of anhydrous ethanol, and one drop of piperidine was added thereto, heated to 80 ℃ under argon atmosphere, and stirred under reflux for 12 hours. After the reaction was stopped, the solvent was dried under reduced pressure, separated by silica gel column chromatography using dichloromethane-methanol (v: v = 20: 1) as an eluent, and then recrystallized from n-hexane/dichloromethane to obtain the indolylbenzimidazole near-infrared fluorescent dye (I) in a yield of 70%. 1 H-NMR(600MHz，DMSO-d 6 ，ppm)：δ＝8.51(d，J＝16.2Hz，1H)，8.32(d，J＝8.4Hz，2H)，8.00-7.99(m，1H)，7.94-7.91(m，3H)，7.79(d，J＝4.8Hz，1H)，7.76(d，J＝5.4Hz，1H)，7.67-7.64(m，2H)，7.59(s，2H)，7.50(d，J＝16.2Hz，1H)，1.22(q，J＝3.0Hz，2H)，4.73(t，J＝7.8Hz，2H)，1.95-1.89(m，2H)，1.85(s，6H)，1.03(t，J＝7.2Hz，3H)；Esi-MS：calculated for C 30 H 30 N 3 + ：432.2434，found：432.2421[M-I - ] + 。
Example 2 UV-VIS absorption spectra of Indolylbenzimidazole NIR fluorescent dyes (I) in different solvents
Dissolving indolyl benzimidazole near infrared fluorescent dye (I) in dichloromethane, methanol, tetrahydrofuran, and dimethyl sulfoxide respectively to obtain a solution with a concentration of 1 × 10 -5 measuring the ultraviolet-visible absorption spectrum of the solution of mol/L; fig. 1 shows uv-vis absorption spectra of fluorescent dye (I) prepared in example 1 of the present invention in different solvents, showing significant solvent effect.
Example 3 fluorescence emission spectra of Indolylbenzimidazole NIR fluorescent dyes (I) in different solvents
Dissolving indolyl benzimidazole near infrared fluorescent dye (I) in dichloromethane, methanol, tetrahydrofuran, and dimethyl sulfoxide respectively to obtain a solution with a concentration of 1 × 10 -5 Determination of the fluorescence of the solution in mol/LLight emission spectrum. FIG. 2 is a fluorescence spectrum of a solution of the fluorescent dye (I) prepared in example 1 of the present invention in different solvents.
EXAMPLE 4 Indolylbenzimidazole near-infrared fluorescent dye (I) for imaging tumor cell fluorescence
Incubating the indolyl benzimidazole near infrared fluorescent dye (I) and the HeLa cell together, and observing an imaging photo of the HeLa cell 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 dye is 347nm; the mHoney Dew excitation wavelength is 509nm; merged is the superposition state. After the fluorescent dye (I) is added into the HeLa cell for incubation, the fluorescent dye enters the HeLa cell for clear imaging, the biocompatibility and the cell permeability are better, and the indolyl benzimidazole near-infrared fluorescent dye (I) can be used for biological cell imaging.
Claims (5)
1. An indolyl benzimidazole near-infrared fluorescent dye is characterized in that the chemical structure of the indolyl benzimidazole near-infrared fluorescent dye is shown as (I):
2. a preparation method of the indolyl benzimidazole near-infrared fluorescent dye shown in the formula (I) according to claim 1, which is characterized by comprising the following steps: carrying out Knoevenagel condensation reaction on a 4-benzimidazole-vinyl benzaldehyde derivative (II) serving as a raw material and 2,3,3-trimethyl-1-propyl-3H-indole iodide (III) to obtain an indolyl benzimidazole near-infrared fluorescent dye shown in a formula (I);
3. the method of claim 2, comprising the steps of:
dissolving 4-benzimidazole vinyl benzaldehyde derivative (II) and 2,3,3-trimethyl-1-propyl-3H-indole salt (III) iodide in absolute ethyl alcohol, dropwise adding a certain amount of piperidine into the solution, and carrying out reflux reaction for 12 hours at 80 ℃ under an argon atmosphere. And (3) cooling to room temperature after the reaction is finished, filtering to remove the filtrate to obtain a dark red solid, and separating the obtained indolylbenzimidazole near-infrared fluorescent dye (I) by silica gel column chromatography.
4. The method according to claim 3, wherein in the step 2, the mass ratio of 4-benzimidazolethylbenzaldehyde (II) to 2,3,3-trimethyl-1-propyl-3H-indolium salt (III) iodide is 1: 1.
5. Use of the indolylbenzimidazole near-infrared fluorescent dye according to claim 1 in near-infrared fluorescence imaging.
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| CN116003390A (en) * | 2023-02-06 | 2023-04-25 | 焦作师范高等专科学校 | Indole-benzimidazole derivative fluorescent probe and preparation method and application thereof |
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| US6761952B1 (en) * | 2003-05-14 | 2004-07-13 | Industrial Technology Research Institute | Bis-styryl dye and method for manufacturing the same and its use for a high density optical recording medium |
| US20190375941A1 (en) * | 2018-06-11 | 2019-12-12 | Institute For Stem Cell Biology And Regenerative Medicine (Instem) | Compounds as fluorescent probes, synthesis and applications thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116003390A (en) * | 2023-02-06 | 2023-04-25 | 焦作师范高等专科学校 | Indole-benzimidazole derivative fluorescent probe and preparation method and application thereof |
| CN116003390B (en) * | 2023-02-06 | 2024-03-08 | 焦作师范高等专科学校 | Indole-benzimidazole derivative fluorescent probe and preparation method and application thereof |
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