CN118146198B - Squarylium cyanine fluorescent probe based on methimazole and its preparation method and application - Google Patents
Squarylium cyanine fluorescent probe based on methimazole and its preparation method and applicationInfo
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Abstract
本发明属于化学分析测试领域，具体涉及一种基于甲巯咪唑的方酸菁类荧光探针及其制备方法和应用。将甲巯咪唑和2‑溴乙胺氢溴酸盐溶于甲苯溶液中，反应液在四丁基溴化铵作为转相剂，40％氢氧化钠溶液作为碱条件下，在60℃加热8小时，所得粗品通过甲醇重结晶，得到中间体1。随后将中间体1和不对称方酸菁染料SQ01与1H‑苯并三唑‑1‑基氧三吡咯烷基六氟磷酸盐和N,N‑二异丙基乙胺在常温下反应，所得粗品通过薄层色谱法分离，得到最终产物SQM‑1。本发明得到的方酸菁类荧光探针SQM‑1在十六烷基三甲基溴化铵表面活性剂水溶液中可快速识别脱氧三磷酸胸苷(dTTP)。
The present invention belongs to the field of chemical analysis and testing, and in particular to a kind of methimazole-based squaryl cyanide fluorescent probe and its preparation method and application.Methimazole and 2 bromoethylamine hydrobromide are dissolved in a toluene solution, and the reaction solution is heated at 60 DEG C for 8 hours under tetrabutylammonium bromide as a phase inversion agent and 40% sodium hydroxide solution as an alkali condition, and the obtained crude product is recrystallized by methanol to obtain intermediate 1.Then intermediate 1 and asymmetric squaryl cyanide dye SQ01 are reacted with 1H-benzotriazole-1-yloxytripyrrolidino hexafluorophosphate and N, N-diisopropylethylamine at room temperature, and the obtained crude product is separated by thin layer chromatography to obtain final product SQM-1.The squaryl cyanide fluorescent probe SQM-1 obtained by the present invention can quickly identify deoxythymidine triphosphate (dTTP) in a hexadecyltrimethylammonium bromide surfactant aqueous solution.
Description
Technical Field
The invention belongs to the field of chemical analysis and test, and particularly relates to a squaraine fluorescent probe based on methimazole, and a preparation method and application thereof.
Background
Deoxythymidine triphosphate (dTTP) is one of four deoxynucleotides responsible for carrying thymine bases and can pair with adenine to form a double helix structure of DNA. Inhibition of dTTP consumption by thymidine synthase results in accumulation of deoxyuridine triphosphate (dUTP) and an increase in the ratio of dUTP to dTTP, whereas DNA polymerase cannot distinguish dUTP from dTTP, which results in large scale misbinding of uracil and extensive DNA damage reactions, resulting in "thymic free death". Therefore, deoxythymidine triphosphate plays a very important role in biology, which is the basis for maintaining genetic information transfer, maintaining cellular structure and function.
The current nucleotide detection method mainly comprises a high performance liquid phase method, a gel electrophoresis method, a polymerase chain reaction method, a nuclear magnetic resonance method and the like, wherein the methods generally need pretreatment of a sample and have long detection period, and the fluorescence analysis method is a sensitive and rapid detection method. Therefore, developing a simple and rapid detection technique for intracellular deoxythymidine triphosphate levels is of great importance for human life health.
Disclosure of Invention
The invention provides a squarylium fluorescence probe SQM-1 based on methimazole, which has the structural formula:
the invention also provides a preparation method of the fluorescent probe based on the methimazole structure, and the chemical reaction formula for preparing the fluorescent probe is as follows:
The preparation method comprises the steps of dissolving methimazole and 2-bromoethylamine hydrobromide in toluene (Toluene) solution according to the molar equivalent of 1:1.2-1.5, then adding 0.1 molar equivalent of tetrabutylammonium bromide (TBAB) and 1.5 molar equivalent of 40% sodium hydroxide solution, heating at 60 ℃ for 8 hours, removing the solvent after the reaction is finished, extracting the crude product by deionized water and ethyl acetate, washing the solid obtained after water phase freeze-drying by methanol, and removing the methanol under reduced pressure to obtain white solid intermediate 1.
The aqueous phase was lyophilized under conditions such that the aqueous phase was frozen at-78 ℃ and lyophilized under vacuum to afford intermediate 1.
Intermediate 1 and asymmetric squaraine dye SQ01 are then dissolved in a 1:1 molar equivalent of Dichloromethane (DCM) solution, then 1 molar equivalent of 1H-benzotriazole-1-yl oxy tripyrrolidinyl hexafluorophosphate (PyBOP) and 2.5 molar equivalents of N, N-Diisopropylethylamine (DIPEA) are added and reacted at normal temperature for 3-6 hours, and the crude product is separated by thin layer chromatography in a mixed solvent of dichloromethane and methanol in a volume ratio of 10:1 to obtain a final blue solid pure product.
The invention also provides an application of the fluorescent probe, wherein the prepared squaraine fluorescent probe SQM-1 based on methimazole can rapidly identify dTTP in a CTAB surfactant aqueous solution.
The concentration of the aqueous CTAB surfactant solution is 0.4-1.0mM.
The method comprises adding 2 μl of 1×10 -2 mol/L nucleotide and analog solution (guanosine triphosphate (GTP) and adenosine triphosphate in each well respectively) into 96-well plates
(ATP), cyclic adenosine monophosphate (cAMP), guanosine Monophosphate (GMP), guanine (G), O-6 benzyl guanine (O6-BG), deoxyguanosine (dG), adenine (A), cytosine (C), thymine acetate (TAA), guanosine (Guanosine), beta-Nicotinamide Mononucleotide (NMN), monododecyl phosphate sodium Salt (SMP), cytidine Triphosphate (CTP), deoxythymidine triphosphate (dTTP), oxidized coenzyme I (NAD), sodium alembide phosphate (AST), blank (Blank)), 196. Mu.L of a 0.5mM cetyltrimethylammonium bromide (CTAB surfactant) solution and 2. Mu.L of squarylium cyanine fluorescent probe (concentration of 0.5X10. 10 -3 mol/L) were used as a comparison. And uniformly mixing the solutions in each hole, and detecting the fluorescence intensity of the solutions in each hole by an enzyme-labeled instrument.
The result shows that the fluorescence intensity of the mixed solution containing deoxythymidine triphosphate at 655nm is 50 times that of the nucleotide-free solution, and the fluorescence intensity of the fluorescent probe has no particularly obvious change for other nucleotides and the like, so that the selective recognition effect of the fluorescent probe on dTTP in a cetyltrimethylammonium bromide (CTAB surfactant) solution is shown.
Squaraine used in the fluorescent probe is a near infrared dye with good optical property and light stability, and can generate strong fluorescence when excited by specific wavelength. And when methimazole and squaraine dye SQ01 are connected through an amide bond, obtaining the final squaraine fluorescent probe. When it recognizes dTTP, the fluorescence intensity is obviously enhanced, but the same effect is not achieved on other nucleotide analogues, so that the aim of detecting dTTP is fulfilled.
In the structure of the probe prepared by the invention, methimazole and squaraine dye and dTTP form a complex through various hydrogen bond interactions and/or electrostatic attraction, so that fluorescence enhancement phenomenon is caused, and the effect of identifying dTTP is achieved.
Advantageous effects
The invention has the advantages of easily obtained raw materials, simpler synthesis method, easily controlled reaction conditions and capability of obtaining a pure product through simple post-treatment. From the fluorescence phenomenon, when different nucleotides are added, the fluorescence intensity of the orifice plate probe SQM-1 added with dTTP at 655nm is remarkably enhanced, so that the recognition effect of the probe SQM-1 on dTTP in the system is shown.
Drawings
FIG. 1 is a graph showing fluorescence spectra of the probe prepared in example 1 after reacting with different nucleotides and the like in a 0.5mM CTAB aqueous solution at a concentration of 0.5X10 -3 mol/L.
FIG. 2 is a graph showing fluorescence spectra of the probe prepared in example 1 after reaction with dTTP at different concentrations in 0.5mM CTAB aqueous solution at a concentration of 0.5X10 -3 mol/L.
FIG. 3 is a graph showing the fluorescence intensity at 655nm of the fluorescent probe prepared in example 1 after the addition of five times interfering nucleotides and the like by dTTP in a 0.5mM aqueous CTAB surfactant solution at a concentration of 0.5X10 -3 mol/L.
FIG. 4 is a hydrogen spectrum of the probe prepared in example 1.
FIG. 5 is a graph showing the recognition ability of dTTP in aqueous solutions of CTAB surfactants at various concentrations for the probe prepared in example 1.
Detailed Description
The invention is further described in detail below in connection with specific embodiments:
example 1
(1) Methimazole (100 mg,0.88 mmol) and 2-bromoethylamine hydrobromide (216 mg,1.05 mmol) were dissolved in a round bottom flask with 4mL toluene as solvent followed by tetrabutylammonium bromide (28 mg,0.088 mmol) and 132. Mu.L 40% sodium hydroxide solution and heated at 60℃for 8 hours. After the reaction, the solvent was removed, the crude product was extracted with deionized water and ethyl acetate, and the aqueous phase was lyophilized to give a solid which was washed with methanol and removed under reduced pressure to give 248mg of intermediate 1 as a white solid.
(2) Intermediate 1 (10 mg,0.064 mmol) obtained in step (1) was dissolved with an asymmetric squaraine dye SQ01 (30 mg,0.053 mmol) in 3mL of dichloromethane, followed by addition of 1H-benzotriazole-1-yloxytripyrrolidinyl hexafluorophosphate (30 mg,0.058 mmol) and N, N-diisopropylethylamine (220 μl,0.135 mmol), reacted at room temperature for 3 hours, the solvent was removed under reduced pressure to give a blue solid, and the final product was obtained after separation and purification by thin layer chromatography (volume ratio of developing solvent: dichloromethane: methanol=10:1) as 20mg, yield 54%.
FIG. 1 shows the preparation of methimazole-based squaraine fluorescent probe of example 1 with different nucleotides and analogues (guanosine triphosphate (GTP), adenosine triphosphate in 0.5mM CTAB surfactant aqueous solution
Fluorescent spectra after Action of (ATP), cyclic adenosine monophosphate (cAMP), guanosine Monophosphate (GMP), guanine (G), O-6 benzyl guanine (O6-BG), deoxyguanosine (dG), adenine (A), cytosine (C), thymine acetate (TAA), guanosine (Guanosine), beta-Nicotinamide Mononucleotide (NMN), sodium salt of phosphoric acid monododecyl ester (SMP), cytidine Triphosphate (CTP), deoxythymidine triphosphate (dTTP), oxidized coenzyme I (NAD), sodium alembidium phosphate (AST), blank (Blank)). The figure shows that the fluorescence intensity of the probe SQM-1 is changed after various nucleotide and analogue solutions with the concentration of 10mM are added dropwise, and the fluorescence intensity of the probe is obviously enhanced after dTTP is added, and other nucleotides are not obviously changed, so that the selective recognition effect of the probe on dTTP in the system is shown.
FIG. 2 is a graph showing fluorescence spectra of the fluorescent probe prepared in example 1 after the fluorescent probe was reacted with dTTP at different concentrations in CTAB aqueous solution at a concentration of 0.5X10 -3 mol/L. The figure shows that the fluorescence intensity of the probe solution gradually increases with increasing dTTP concentration. When the minimum concentration is 10 mu M, the fluorescence peak at 655nm can still be distinguished from the background fluorescence curve without adding nucleotide, so that the detection limit of the probe on dTTP is low and the sensitivity is high.
FIG. 3 is a graph showing the fluorescence intensity at 655nm of the fluorescent probe prepared in example 1 after the addition of five times interfering nucleotides and the like by dTTP in CTAB aqueous solution at a concentration of 0.5X10 -3 mol/L. The figure shows that when only dTTP solution is added, the fluorescence intensity of the probe solution is remarkably increased relative to a Blank, and the probe has no particularly obvious fluorescence change to other nucleotides (guanosine triphosphate (GTP), adenosine Triphosphate (ATP), cyclic adenosine monophosphate (cAMP), guanosine Monophosphate (GMP), guanine (G), O-6 benzyl guanine (O6-BG), deoxyguanosine (dG), adenine (A), cytosine (C), thymine Acetic Acid (TAA), guanosine (Guanosine), beta-Nicotinamide Mononucleotide (NMN), sodium dodecyl phosphate (SMP), cytidine Triphosphate (CTP), deoxythymidine triphosphate (dTTP), oxidized coenzyme I (NAD), sodium alembic phosphate (AST) and Blank (Blank)), and then the fluorescence intensity change of the probe at 655nm after 5 times of other nucleotides and analogue solutions are added in a detection system, the addition of other proteins and redox substances does not cause the decrease of the probe to the dTTP detection result, so that the fluorescence resistance is strong in the detection process.
FIG. 4 is a hydrogen spectrum of methimazole-based squaraine fluorescent probe prepared in example 1 .1H NMR(400MHz,Methanol)δ7.88(s,1H),7.49(d,J＝7.3Hz,1H),7.39(t,J＝7.5Hz,1H),7.30(m,J＝22.0Hz,2H),7.25(d,J＝4.0Hz,1H),7.22(s,1H),7.19(d,J＝1.4Hz,1H),7.04(d,J＝1.4Hz,1H),6.05(s,1H),5.95(s,1H),4.23(q,J＝6.8Hz,2H),4.08(s,2H),3.71(s,3H),3.58(m,J＝44.4Hz,4H),1.75(s,12H),1.41(td,J＝7.2,2.5Hz,6H),1.29(m,J＝25.4Hz,9H),0.87(t,J＝6.9Hz,3H).
Example 2
(1) Methimazole (200 mg,1.76 mmol) and 2-bromoethylamine hydrobromide (493 mg,2.64 mmol) were dissolved in a round bottom flask with 8mL toluene as solvent followed by tetrabutylammonium bromide (55 mg,0.176 mmol) and 250. Mu.L 40% sodium hydroxide solution and heated at 60℃for 8 hours. After the reaction, the solvent was removed, the crude product was extracted with deionized water and ethyl acetate, and the aqueous phase was lyophilized to give a solid which was washed with methanol and removed under reduced pressure to give 506mg of intermediate 1 as a white solid.
(2) Intermediate 1 (20 mg,0.064 mmol) obtained in step (1) was dissolved with an asymmetric squaraine dye SQ01 (60 mg,0.106 mmol) in 5mL of dichloromethane, followed by addition of 1H-benzotriazole-1-yloxytripyrrolidinyl hexafluorophosphate (30 mg,0.058 mmol) and N, N-diisopropylethylamine (220 μl,0.135 mmol), reacted at 0 ℃ for 6 hours, and removal of the solvent under reduced pressure to give a blue solid, which was isolated and purified by thin layer chromatography (developer volume ratio: dichloromethane: methanol=10:1) to give the final product 44mg in 59% yield.
Example 3
To 96-well plates, 2. Mu.L of deoxythymidine triphosphate solution at a concentration of 1X 10 -2 mol/L was added, and 13 groups were placed in parallel, and 13 groups of cetyltrimethylammonium bromide solutions (0 mM, 0.1mM, 0.2mM, 0.3mM, 0.4mM, 0.5mM, 0.6mM, 0.7mM, 0.8mM, 0.9mM, 1.0mM, 2.0mM, 3.0 mM) at different concentrations and 2. Mu.L of squarylium fluorescent probe (at a concentration of 0.5X10 -3 mol/L) were added, respectively, and the fluorescent intensity of the solution in each well was detected by a microplate reader. The result shows that the fluorescent probe can effectively recognize dTTP under the condition of a CTAB aqueous solution system of 0.4-1.0 mM.
The specific recognition capacity of the probe for dTTP was studied in aqueous solutions of CTAB surfactants of different concentrations. Specific data are shown in FIG. 5, in which the concentration of the CTAB surfactant aqueous solution is shown on the abscissa and the difference in fluorescence intensity of the probe before and after dTTP addition is shown on the ordinate, and is represented by I-I 0. The graph shows that the probe has obvious recognition capability on dTTP at CTAB concentration of 0.4 mM-1.0 mM.
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| CN107417670A (en) * | 2017-07-08 | 2017-12-01 | 常州大学 | A kind of near-infrared squarylium cyanine dyes probe based on thymidine and its preparation method and application |
| CN108191738A (en) * | 2018-01-14 | 2018-06-22 | 常州大学 | Sour cyanines probe in a kind of side based on silver ion identification and its preparation method and application |
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| EP3039082B1 (en) * | 2013-08-30 | 2017-10-04 | Council of Scientific and Industrial Research | A squaraine based fluorescent probe and a process for the preparation thereof |
| CN112812767B (en) * | 2021-01-22 | 2022-08-23 | 常州大学 | Squarylium cyanine probe based on N, N-di (2-picolyl) amine (DPA) and preparation method and application thereof |
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| CN107417670A (en) * | 2017-07-08 | 2017-12-01 | 常州大学 | A kind of near-infrared squarylium cyanine dyes probe based on thymidine and its preparation method and application |
| CN108191738A (en) * | 2018-01-14 | 2018-06-22 | 常州大学 | Sour cyanines probe in a kind of side based on silver ion identification and its preparation method and application |
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