CN106645058A - Switch type glutathione fluorescence detection method based on porphyrin compound - Google Patents

Switch type glutathione fluorescence detection method based on porphyrin compound Download PDF

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CN106645058A
CN106645058A CN201611016744.8A CN201611016744A CN106645058A CN 106645058 A CN106645058 A CN 106645058A CN 201611016744 A CN201611016744 A CN 201611016744A CN 106645058 A CN106645058 A CN 106645058A
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solution
fluorescence
glutathione
porphyrin
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CN106645058B (en
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陈晶
马琴
冉宝成
虎晓燕
高云静
严小雨
卢小泉
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Northwest Normal University
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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • 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
    • G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

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Abstract

The invention relates to a switch type glutathione fluorescence detection method based on a porphyrin compound. According to the method, tetraphenylporphyrin is prepared from propionic acid, benzoic acid and porphyrin; the tetraphenylporphyrin is dissolved by chloroform; a sulfuric acid solution is added; constant-temperature backflow is performed to obtain a clear solution; after cooling, a NaHCO3 solution is dripped; after ice-water bath cooling, filtering is performed; a filtered liquid is dried by distillation; solid products are dissolved by methanol; filtering is performed; filtering liquid is collected; the operations are repeated for 2 to 3 times; filtering liquid is merged; recrystallization, filtering and vacuum drying are performed to obtain the porphyrin compound; a porphyrin solution is prepared; a PBS buffer solution and a Hg<2+> solution are added; still standing is performed to obtain a fluorescent probe; a glutathione stock solution is added; the fluorescence intensity change of the fluorescent probe is detected; then, the glutathione stock solution is added again, and the fluorescence intensity change of the fluorescent probe is detected; the process is repeated until the fluorescence intensity of the fluorescent probe is not changed; the fluorescence emission spectrum is detected through a fluorescence spectrophotometer. The detecting method has the advantages that the detection limit is very low; the naked eye detection effect can be achieved.

Description

Method based on porphyrin compound switching mode fluoroscopic examination glutathione
Technical field
The invention belongs to food and living things system detection technique field, are related to paddy Guang in a kind of detection food and living things system A kind of method of sweet peptide, and in particular to method based on porphyrin compound switching mode fluoroscopic examination glutathione.
Background technology
With society and economic fast development, the life of the mankind becomes rich and varied, the delicious food on various the tip of the tongue Food arises at the historic moment, and to our life unlimited enjoyment is brought.But everything has dual character, with sending out for mankind's science and technology Exhibition, various problems are occurred in that, such as food quality, energy crisis and environmental degradation and the most concerned health problem of the mankind A series of problems, such as have turned into the problem of global common concern.
Glutathione is made up of glutamic acid, cysteine and glycine, is main in most of mammalian tissues Nonprotein low-molecular-weight sulfhydryl compound, in many life processes such as signal transduction, anti-oxidant and cell propagation Play important role.As bioactive sulfhydryl material important in body, glutathione（GSH）For maintenance organism Interior suitable redox environment plays vital effect.Clinically, GSH can rapidly improve immunity of organisms；In food Product manufacture field, GSH has strengthens the function such as food value and condensed food local flavor.According to medical science, relevant departments report for work, GSH Content it is closely bound up with human diseases, such as cancer, hepar damnification, AIDS, aging and diabetes etc..Therefore one kind is found Convenient, efficient GSH detection methods are significant for our life.Therefore, seek efficient, environmentally friendly, inexpensive The method of analysis detection GSH has been known as the target that researcher is pursued.Recent study person reports various in succession The method of quantitative determination glutathione, such as spectrofluorimetry, high performance liquid chromatography, electrochemical test method and ultraviolet point Light photometry etc..Compared with other methods, with it is simple to operate, with low cost, without destructive and sensitivity the features such as higher XRF is favored.
Porphyrin is a kind of natural macromolecular compound, the conjugate planes structure with 16 electronics of atom 18, therefore it has There are the physicochemical properties such as superior light, electricity.Its middle position and β positions can be replaced by different substituents and form different porphyrin chemical combination Thing, thus it not only photoelectric material, molecular recognition, self assembly, fluorescence analysis, pharmaceutical synthesis, natural products simulation, electrochemistry The field such as catalysis and medical science developer is widely used, and is present in animal and plant body, oxygen is played in biological oxidation process Transmission, storage, activation and electric transmission effect.
At present, the method for many analysis detection glutathione is prepared, analyzes testing cost, device requirement and inspection in material Have the shortcomings that in terms of surveying sensitivity different degrees of.
The content of the invention
It is an object of the invention to provide a kind of with low cost based on porphyrin compound switching mode fluoroscopic examination glutathione Method, reduce detection difficulty.
For achieving the above object, the technical solution adopted in the present invention is：One kind is based on porphyrin compound switching mode fluorescence The method of detection glutathione, is specifically carried out according to the following steps：
1）After 250mL propionic acid oil bath heating to micro-boiling, 10mL benzaldehydes are added, obtain material liquid；
After by 7mL pyrroles's vacuum distillation, in being dissolved in 30mL propionic acid, dropping liquid is obtained；
2）Dropping liquid is slowly dropped into material liquid, is flowed back when being added dropwise, after completion of dropping, continue to stop heating after backflow 1h, it is cold But to room temperature, stand；Suction filtration, with respectively washing 2～3 times of absolute ethyl alcohol and secondary water, drying obtains violet solid；Sample is mixed, post layer is used Analysis method is purified, and eluant, eluent is the mixture of dichloromethane and petroleum ether；Rotate, dry to obtain tetraphenylporphyrin；
3）200mg tetraphenylporphyrins are dissolved with 3～5mL chloroforms, the H of 10mL mass fraction >=70% is slowly added into2SO4Solution, magnetic 95 DEG C are heated under power stirring, the 4h of constant temperature backflow afterwards obtains clarified solution, is cooled to room temperature, and the clarified solution is instilled into 200mL mole Volumetric concentration is the NaHCO of 1mol/L3In solution, it is stirred while dropwise addition, obtains solution, ice-water bath cooled and filtered, Filtered solution is evaporated, is dissolved with 150mL methyl alcohol, filter and collect filtrate；Repeat aforesaid operations 2～3 times, merging filtrate is added 100mL isopropanols are recrystallized, and are filtered, and are vacuum dried to obtain porphyrin compound；
4）0.0001g porphyrin compounds are dissolved in 25mL ultra-pure waters, substance withdrawl syndrome is configured to for 1 × 10-4Mol/L's Porphyrin solution；
5）The porphyrin solution prepared in 500uL steps 4 is pipetted in 2mL, the PBS of 1mL molal volume concentration 0.5mol/L is added Cushioning liquid, adds 38uL concentration for the Hg of 2.24mM2+Solution, stands 5min, and TPPS is obtained4-Hg2+Fluorescence probe；
6）Take the TPPS obtained in 1mL steps 54-Hg2+Fluorescence probe, is initially charged the glutathione storing solution of 0.5uL, detects glimmering The change of light probe fluorescence intensity, then adds 0.5uL glutathione storing solutions, detects the change of fluorescence probe fluorescence intensity Change, repeat this process till the fluorescence intensity of fluorescence probe no longer changes, fluorescence emission is detected by XRF Spectrum.
Detection method adopts the preferable porphyrin compound of fluorescence property, not only fairly simple in preparation method, Cost greatly reduces to a certain extent the difficulty of detection than less expensive, and porphyrin compound is in itself a kind of natural Organic pigment molecule, the color change that moment can occur when it runs into target detection thing glutathione, test limit, can than relatively low With reach naked eyes detection effect, this be existing many fluoroscopic examination glutathione analysis method institute it is not indispensable the characteristics of. This detection method also add the means of theoretical calculation, and Binding experiment phenomenon makes rational explanation.Manage with reference to Density functional By（DFT）The method of calculating, from the root of the change of the interpretation photoluminescent property of the change of molecular structure.
Description of the drawings
Fig. 1 is the infrared spectrogram of the final compound prepared in detection method.
Fig. 2 is the ultraviolet-visible absorption spectroscopy figure and fluorescent emission of the porphyrin compound prepared in detection method Spectrogram.
Fig. 3 is the TPPS prepared in detection method4-Hg2+The fluorescent emission of the fluorescence closing process of fluorescence probe Spectrogram.
Fig. 4 is with the TPPS prepared in detection method4-Hg2+Fluorescence probe detects the process schematic of GSH.
Fig. 5 is that density functional theory is based in detection method（DFT）The porphyrin chemical combination that experiment with computing is adopted The optimum structure of thing（That is the minimum molecular configuration of energy）Figure.
Fig. 6 is that density functional theory is based in detection method（DFT）The porphyrin compound that experiment with computing is adopted Frontier molecular orbitals cloud density distribution map.
Specific embodiment
Below example facilitates a better understanding of the present invention, but does not limit the present invention.Experiment in following embodiments Method, if no special instructions, is conventional method.
The invention provides a kind of method of detection food and living things system GSH-PX activity, specifically enters according to the following steps OK：
1）250mL propionic acid, oil bath heating is added to be subsequently adding 10mL benzaldehydes to micro-boiling, obtain in 500mL three neck round bottom Material liquid；
By 7mL pyrroles's vacuum distillation at a temperature of 90 DEG C（Standing time length has polymer generation）, it is then dissolved in 30mL third In acid, dropping liquid is obtained；
2）Dropping liquid is slowly dropped into material liquid, is flowed back when being added dropwise, after completion of dropping, continue to stop heating after backflow 1h, Room temperature is cooled to, is placed in the environment that temperature is 4 DEG C and is stood 12h；Suction filtration, is respectively washed 2～3 times with absolute ethyl alcohol and secondary water, Drying, obtains violet solid；Sample is mixed, is purified with column chromatography, eluant, eluent is dichloromethane and the mixture of petroleum ether, eluant, eluent body Accumulating ratio is：Er Lv Jia Wan ︰ petroleum ether=3 ︰ 1；Rotate, dry to obtain tetraphenylporphyrin（TPP）4g, yield is 58%（The quality of product With the mass ratio of the reactant for adding）；
3）In 100mL round-bottomed flasks, 200mg tetraphenylporphyrins are added, dissolved with 3～5mL chloroforms, be slowly added into 10mL mass The H of fraction >=70%2SO495 DEG C are heated under solution, magnetic agitation, the 4h of constant temperature backflow afterwards obtains green settled solution, is cooled to After room temperature, the clarified solution is instilled into NaHCO of the 200mL molal volume concentration as 1mol/L with the drop speed of 10 drop/min3In solution, Mixing is stirred while dropwise addition, purple solution is obtained, ice-water bath cooled and filtered removes Na2SO4Crystal, is evaporated filtration Liquid, obtains solid product, and with 150mL methyl alcohol the solid product is dissolved, and filters and collect filtrate；Repeat aforesaid operations 2～3 times, close And filtrate, add 100mL isopropanols to be recrystallized, violet solid is filtered to obtain, 60 DEG C are vacuum dried to obtain final compound 80mg, Yield about 40%；
Above-mentioned steps 3）The infrared spectrogram of the final compound obtained after middle vacuum drying, is shown in Fig. 1, as can be seen from Figure 1 966 cm-1The absworption peak that place occurs is the N-H flexural vibrations absworption peaks of porphyrin ring, is all middle strong absorption band, and this is the feature of porphyrin ring Vibration.1483cm-1For phenyl ring and porphyrin ring skeleton C=C double bond vibration absorption peak, 1517cm-1For phenyl ring stretching vibration absworption peak, 1607cm-1The N-C stretching vibrations of porphyrin ring absorb, 1729cm-1C=C stretching vibration absworption peaks, 2580cm-1-2940cm-1C- H stretching vibration absworption peaks, 1190 cm-1Occur sulfonic characteristic absorption peak at left and right, illustrate that the final compound is porphyrin Compound（TPPS4）.Fig. 2 is the ultraviolet-visible absorption spectroscopy figure of the porphyrin compound（Curved portion in Fig. 2）And fluorescent emission Spectrogram（Right-hand component in Fig. 2）, can be seen that obtained porphyrin compound has one in wavelength 410nm or so from abosrption spectrogram Individual very strong characteristic absorption peak, there is four weaker Q absworption peaks between 500～650nm of wavelength；Can from fluorescence emission spectrogram of compound With it is evident that, when under the excitation wavelength of 515nm, TPPS4There is very strong sending out at wavelength 650nm and wavelength 705nm Peak is penetrated, it can be seen from Fig. 2, TPPS4With good optical property.
4）0.0001g porphyrin compounds are dissolved in 25mL ultra-pure waters, substance withdrawl syndrome is configured to for 1 × 10-4mol/L Porphyrin solution（Color is purple）；
5）The preparation of fluorescence probe：The porphyrin solution prepared in 500uL steps 4 is accurately pipetted in 2mL sample cells, is added 1mL（Molal volume concentration 0.5mol/L）PBS cushioning liquid（pH=7）, add 38uL（2.24mM）Hg2+Solution, stands 5min, is obtained TPPS4-Hg2+Fluorescence probe；
Obtained TPPS4-Hg2+The fluorescence emission spectrogram of compound of the fluorescence closing process of fluorescence probe, is shown in Fig. 3, as can be seen from Figure With Hg2+The increase of concentration, TPPS4The fluorescence intensity of solution is constantly reduced, and illustrates TPPS4And Hg2+Between have an effect, and Make TPPS4The fluorescence intensity of solution is reduced.
6）Fluoroscopic examination glutathione：Pipette the TPPS obtained in 1mL steps 54-Hg2+Fluorescence probe is placed in quartz cuvette In ware, the glutathione storing solution of 0.5uL is initially charged, detects the change of fluorescence probe fluorescence intensity, then add 0.5uL paddy The sweet peptide storing solution of Guang, detects the change of fluorescence probe fluorescence intensity, so repeats this process until the fluorescence intensity of fluorescence probe Till no longer changing, fluorescence emission spectrum is detected by XRF, excitation wavelength is 515nm, slit width be 5nm × 5nm；
The fluorescence probe obtained with step 5 detects fluorescence emission spectrogram of compound during glutathione, as shown in figure 4, can from figure Go out as the concentration of glutathione is continuously increased, TPPS4-Hg2+The fluorescence intensity of fluorescence probe gradually strengthens.Illustrate that GSH can be with And Hg2+React, and make TPPS4Fluorescence recover.
7）TPPS is calculated using TD-DFT/B3LYP/6-31G (d) and LANL2DZ bases group4With Hg2+Occurring should be raw afterwards Into the properties of the excitation state of product, using DFT theoretical calculations us can be helped to explain the phenomenon seen in experiment, i.e., When to TPPS4Middle addition Hg2+During solution, why TPPS4Fluorescence intensity can reduce；It is soft using Gaussian09 during calculating Part bag（Gaussian 09, Revision A.02, Gaussian, Inc）.
Based on Density functional（DFT）Why theoretical research is fundamentally explained Hg2+Solution is added to TPPS4Solution It is central, TPPS4Fluorescence can reduce.
Obtained TPPS in detection method4Hg is added in solution2+Apparent color change can occur, and The state that the reduction of fluorescence intensity, i.e. fluorescence molecule are closed in fluorescence can be seen in fluorescence emission spectrum.However, work as having In the presence of GSH, fluorescence probe TPPS4-Hg2+In Hg2+Can be specifically bound by glutathione, and then make TPPS4Solution Fluorescence intensity increases, i.e., the process that fluorescence recovers occurs.Based on this process, the present invention establishes a kind of switching mode fluorescent optical sensor （It is firstly added containing Hg2+Solution make TPPS4Fluorescent quenching, i.e. closing process；Being subsequently adding GSH can make TPPS again4Fluorescence Recover, i.e. opening procedure；Therefore the referred to as fluorescent optical sensor of switching mode）For the detection of GSH.
Fig. 5 is density functional theory（DFT）Calculated TPPS4And TPPS4-Hg（TPPS4With Hg2+The product of interaction Thing）Optimum structure（Find the minimum structure of energy）Fig. 6 is density functional theory（DFT）Calculated TPPS4And TPPS4- Hg（TPPS4With Hg2+The product of interaction）Frontier molecular orbitals cloud density distribution map（HOMO refers to that highest electronics occupies Track, LUMO refers to lowest unoccupied molecular orbital）.Knowable to figure, TPPS4Frontier molecular orbital energy levels difference be 2.778eV, and TPPS4-Hg Frontier molecular orbitals energy extreme difference be 2.701eV.Illustrate TPPS4Electronics in-Hg in HOMO tracks is easier transition.I.e. its The energy that electron transition absorbs is less, and then the energy that electronics is discharged from ground state transition to excitation state is just few, fluorescence intensity Reduce.
Finally it should be noted that：The preferred embodiments of the present invention are the foregoing is only, this is not limited to Bright, although being described in detail to the present invention with reference to the foregoing embodiments, for a person skilled in the art, it is still Technical scheme described in foregoing embodiments can be modified, or equivalent is carried out to which part technical characteristic and replaced Change.All any modification, equivalent substitution and improvements within the spirit and principles in the present invention, made etc., should be included in the present invention Protection domain within.

Claims (3)

1. a kind of method based on porphyrin compound switching mode fluoroscopic examination glutathione, it is characterised in that detection method tool Body is carried out according to the following steps：
1）After 250mL propionic acid oil bath heating to micro-boiling, 10mL benzaldehydes are added, obtain material liquid；
After by 7mL pyrroles's vacuum distillation, in being dissolved in 30mL propionic acid, dropping liquid is obtained；
2）Dropping liquid is slowly dropped into material liquid, is flowed back when being added dropwise, after completion of dropping, continue to stop heating after backflow 1h, it is cold But to room temperature, stand；Suction filtration, with respectively washing 2～3 times of absolute ethyl alcohol and secondary water, drying obtains violet solid；Sample is mixed, post layer is used Analysis method is purified, and eluant, eluent is the mixture of dichloromethane and petroleum ether；Rotate, dry to obtain tetraphenylporphyrin；
3）200mg tetraphenylporphyrins are dissolved with 3～5mL chloroforms, the H of 10mL mass fraction >=70% is slowly added into2SO4Solution, magnetic 95 DEG C are heated under power stirring, the 4h of constant temperature backflow afterwards obtains clarified solution, is cooled to room temperature, and the clarified solution is instilled into 200mL mole Volumetric concentration is the NaHCO of 1mol/L3In solution, it is stirred while dropwise addition, obtains solution, ice-water bath cooled and filtered, Filtered solution is evaporated, is dissolved with 150mL methyl alcohol, filter and collect filtrate；Repeat aforesaid operations 2～3 times, merging filtrate is added 100mL isopropanols are recrystallized, and are filtered, and are vacuum dried to obtain porphyrin compound；
4）0.0001g porphyrin compounds are dissolved in 25mL ultra-pure waters, substance withdrawl syndrome is configured to for 1 × 10-4The porphin of mol/L Quinoline solution；
5）The porphyrin solution prepared in 500uL steps 4 is pipetted in 2mL, the PBS of 1mL molal volume concentration 0.5mol/L is added Cushioning liquid, adds 38uL concentration for the Hg of 2.24mM2+Solution, stands 5min, and TPPS is obtained4-Hg2+Fluorescence probe；
6）Take the TPPS obtained in 1mL steps 54-Hg2+Fluorescence probe, is initially charged the glutathione storing solution of 0.5uL, detects glimmering The change of light probe fluorescence intensity, then adds 0.5uL glutathione storing solutions, detects the change of fluorescence probe fluorescence intensity Change, repeat this process till the fluorescence intensity of fluorescence probe no longer changes, fluorescence emission is detected by XRF Spectrum.
2. the method based on porphyrin compound switching mode fluoroscopic examination glutathione according to claim 1, its feature exists In using XRF detection fluorescence emission spectrum, excitation wavelength 515nm during detection, slit width in the step 6 5nm×5nm。
3. the method based on porphyrin compound switching mode fluoroscopic examination glutathione according to claim 1, its feature exists In after completing the detection of glutathione, using TD-DFT/B3LYP/6-31G (d) and LANL2DZ bases group calculating TPPS4With Hg2+ There is a property of the excitation state that should afterwards generate product；Gaussian09 software kits are adopted during calculating.
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CN112028899A (en) * 2020-08-31 2020-12-04 青海民族大学 Preparation of TSPP and application thereof in detecting content of sulfur ions

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CN112028899A (en) * 2020-08-31 2020-12-04 青海民族大学 Preparation of TSPP and application thereof in detecting content of sulfur ions
CN112028899B (en) * 2020-08-31 2023-03-17 青海民族大学 Preparation of TSPP and application thereof in detecting sulfur ion content

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