CN106565729B - Pyrazine rhodamine 6G fluorescent probe compounds and the preparation method and application thereof - Google Patents
Pyrazine rhodamine 6G fluorescent probe compounds and the preparation method and application thereof Download PDFInfo
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- CN106565729B CN106565729B CN201610996921.7A CN201610996921A CN106565729B CN 106565729 B CN106565729 B CN 106565729B CN 201610996921 A CN201610996921 A CN 201610996921A CN 106565729 B CN106565729 B CN 106565729B
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two 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
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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
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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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- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
The invention discloses pyrazine rhodamine 6G fluorescent probe compounds and the preparation method and application thereof.It is that in organic solvent, rhodamine 6G hydrazides and acetyl group pyrazine are mixed, and to sufficiently dissolve, second acid as catalyst is added; mixed system is heated to reflux to fully reacting again, crude product is obtained after post-treated, is dried in vacuum overnight; gained crude product, through pillar layer separation, eluant, eluent v:V is ethyl acetate:Petroleum ether=6:1, obtain target compound；Wherein rhodamine 6G hydrazides：Acetyl group pyrazine：The molar ratio of catalyst is 1-1.2：1：0.1-0.05.The present invention further discloses compound I to metal cobalt ions with the purposes in terms of highly selective naked eye colour developing identification and fluorescence identifying probe.
Description
The present invention is in Tianjin State Scientific and Technological Commission fund（Fund number：14JCYBJC23900）, Tianjin Normal University's fund（Fund number：
53H14040）Subsidy under carry out.
Technical field
The present invention relates to environmental science, chemical sensitisation technology and bioanalysis application fields, and it is glimmering to be related to pyrazine rhodamine 6G
Light probe compound is identified as receptor to the naked eye colour developing specific to metal cobalt ions, highly selective and the use of fluorescence identifying
On the way.
Background technique
Determination of multiple metal elements plays an important role in the fields such as biology, medicine, environmental science.Some transition metal from
Son is that life process is indispensable at low concentrations（Participate in biological transport, coenzyme of biocatalytic reaction enzyme etc.）, still, when
When excessive concentration toxic action will be caused to biological cell or tissue.Therefore, it is highly selective measurement, identify certain metal from
Son to water quality and soil quality monitoring, is extremely important to guarantee life security.
There are many currently used detection metal ion methods, such as colorimetric method, indicator method, electrode method and optical sensor
Deng.But sensitivity is lower when colorimetric method for determining, cannot be measured to the metal ion in active somatic cell.Indicate agent method spirit
Sensitivity and selectivity are low.Electrical interference or damage cell can be generated when determination of electrode, therefore are not suitable for cell microscopy.
In contrast, the photochemical method based on fluorescence probe is without these defects.Fluorescence probe analysis method has selectivity good, clever
The features such as sensitivity is high, sample size is small, simple and efficient.
Summary of the invention
The compound I that this patent is invented is a kind of Co based on pyrazine rhodamine 6G2+Fluorescent molecular probe has Luo Dan
The characteristics of bright 6G lactams loop coil " closure-colourless ", " coloured be stimulated of open loop-generates fluorescence ", there is schiff bases imines C=N
Double bond structure can carry out highly selective fluorescence identifying to cobalt ions by coordination.Experiment show compound I have pair
The purposes of hydrogen ion highly selective naked eye colour developing identification and fluorescence identifying probe, and not by metal ion disturbance.
The compound with I structure feature as described above of the present inventor's design is the noval chemical compound having not been reported.
The first purpose of the invention is to provide the compounds with structural formula I.
A second object of the present invention is to provide develop the color to know for the naked eye highly selective to cobalt ions comprising compound I
Other and fluorescence identifying probe purposes.
The invention discloses following technology contents to achieve the above object：
Compound with structural formula IN'-(2- pyrazinyl)-ethylidene rhodamine 6G hydrazides：
The present invention further discloses compoundsN'-(2- pyrazinyl)-ethylidene rhodamine 6G hydrazides preparation method, change
The preparation for closing object I carries out as follows：
The synthesis of compound：
Rhodamine 6G hydrazides and acetyl group pyrazine are put into round-bottomed flask, be added methanol, to sufficiently dissolve add it is several
Drop glacial acetic acid makees catalyst, and mixed system is heated to reflux to fully reacting, reaction system is cooled to room temperature, will be in flask
Mixed system is transferred in the beaker for filling mixture of ice and water, adjusts solution ph to having solid analysis when showing slightly alkalinity with organic base
Out, it is filtered by vacuum, is washed with distilled water precipitating, obtains crude product, be dried in vacuum overnight.Gained crude product is through pillar layer separation
(ethyl acetate:Petroleum ether=6:1, v:V), target compound is obtained.
The present invention further discloses compound I to be used as to cobalt ions highly selective naked eye colour developing identification and fluorescence identifying
Application in terms of probe.
Compound designed by the present inventionMolecular characterization be in the structure of I, the lactams spiral shell of rhodamine 6G
Ring is closed state, solution be it is colourless, when cobalt ions and compoundWhen effect, loop coil opening becomes quinoid structure, at this time solution
Become orange red and with fluorescent emission from colourless.Therefore, compoundFluorescence identifying can be carried out to cobalt ions.Experiment shows
Compound I has the purposes of naked eye the colour developing identification and fluorescence identifying probe highly selective to cobalt ions.
Possessed good effect is compound I disclosed in this invention compared with prior art：
（1）Safe preparation process, synthesis are simple；There is high sensitivity, highly selective and fast reactivity etc. to cobalt ions
Advantage.
（2）The fluorescence probe is when detecting cobalt ions not by Mg2+、Ca2+、Mn2+、Fe3+、Ni2+、Cu2+、Zn2+、Sr2+、Cd2 +、Ba2+、Hg2+、Pb2+、Bi3+The interference of plasma；
（3）The pH range that the fluorescence probe adapts to is wide in range, suitable for the cobalt ions biological cell is measured and is known
Not.
Detailed description of the invention：
Fig. 1 is the structural formula of compound I；
Fig. 2 is compound I (10μM THF/)tris-HCl (4:6, v/ v, pH=7.5) blank solution and 5
The ultra-violet absorption spectrum of times 14 metal ion species solution of equivalent；
Fig. 3 is compound I (10μM THF/)tris-HCl (4:6, v/ v, pH=7.5) blank solution and 5
The fluorescence emission spectrum of times 14 metal ion species solution of equivalent；
Fig. 4 is compound I blank under white light (right side in figure) and the imaging contrast to cobalt ions identification；
Fig. 5 is compound I blank under fluorescence (right side in figure) and the imaging contrast to cobalt ions identification；
Fig. 6 is compoundMass spectrogram；
Fig. 7 be compound I to cobalt ions ion identification when 13 metal ion species interference elimination ultra-violet absorption spectrum；
Fig. 8 be compound I to cobalt ions ion identification when 13 metal ion species interference elimination fluorescence emission spectrum；
Fig. 9 is that compound I titrates ultraviolet spectra to cobalt ions；
Figure 10 is compound I to cobalt ions titration fluorescence spectrum；
Figure 11 is that compound I identifies pH fluorescence titration curve to cobalt ions；
Figure 12 detects for compound I to the cobalt ions in living cells and its fluorescence imaging；Scale in picture is 20 μm.
Specific embodiment：
In order to more fully explain implementation of the invention, following preparation method embodiments are provided.These embodiments are only
It is only to explain, be not intended to limit the scope of the invention.In order to simple and clear, well known technical method is retouched in following discussion
It states, the process for preparation of solution repeats no more.Wherein raw material rhodamine 6G hydrazides acetyl group pyrazine is commercially available.
Embodiment 1.
CompoundSynthesis：
1.0 g rhodamine 6G hydrazides and 0.28 g 2- acetyl group pyrazine are added in 100 mL flasks, 10 mL methanol are added
It stirring at normal temperature 10 minutes, to sufficiently dissolve, then adds 0.1 mL glacial acetic acid and makees catalyst, mixed system is heated to reflux 3
Hour to fully reacting, reaction system is cooled to room temperature, the mixed system in flask is transferred to and fills mixture of ice and water
In beaker, adjust solution with triethylamine has solid precipitation in beaker to alkalinity, pH value 7-7.5 is shown slightly immediately, is filtered by vacuum,
It is washed with distilled water precipitating 2-3 times, obtains crude product, be dried in vacuum overnight.Gained crude product is through pillar layer separation (acetic acid second
Ester:Petroleum ether=6:1, v:V), 0.8 g of target compound, yield 66%, mp are obtained> 300 ℃.
1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.67 (s, 1H), 8.64 (s, 2H), 7.90
(d, J = 6.8 Hz, 1H), 7.60 (p, J = 7.1 Hz, 2H), 7.13 (d, J = 7.0 Hz, 1H), 6.27
(s, 4H), 5.04 (t, J = 5.1 Hz, 2H), 3.17–3.06 (m, 4H), 2.25 (s, 3H), 1.88 (s,
6H), 1.19 (t, J = 7.1 Hz, 6H)。
13C NMR (100 MHz, DMSO-d6) δ(ppm): 166.95, 151.78, 149.96, 148.04,
145.90, 144.16, 142.73, 133.67, 130.23, 129.19, 127.79, 124.42, 123.48,
118.48, 105.86, 96.04, 67.19, 39.99, 37.94, 17.51, 14.62。
MS (ESI-MS)：m/z, 533.4 [M+H]+
The synthetic route of the above reaction process is as follows：
Embodiment 2.
CompoundSynthesis：
2.5 g rhodamine 6G hydrazides and 0.8 g acetylpyrazine are added in 100 mL flasks, and 15 mL methanol are added will
Solid dissolution, then 0.2 mL glacial acetic acid is added dropwise and makees catalyst, mixed system is heated to reflux to complete reaction, reaction system is cold
But it is transferred in the beaker for filling mixture of ice and water to mixed system after room temperature, adjusts solution to showing slightly alkaline ph values with triethylamine
For 7-7.5, there is solid precipitation immediately in beaker, be filtered by vacuum, be washed with distilled water precipitating 2-3 time, obtain crude product, vacuum is done
It is dry overnight.Gained crude product is through pillar layer separation (ethyl acetate:Petroleum ether=6:1, v:V), target chemical combination is obtained
1.9 g of object, yield 61%, mp> 300 ℃.
Embodiment 3
CompoundSynthesis：
5.0 g rhodamine 6G hydrazides and 2.0 g acetylpyrazines are added in 100 mL flasks, and 20 mL methanol are added will
Solid dissolution, then 0.5 mL glacial acetic acid is added dropwise and makees catalyst, mixed system is heated to reflux to complete reaction, reaction system is cold
But it is transferred in the beaker for filling mixture of ice and water to mixed system after room temperature, adjusts solution to showing slightly alkaline ph values with triethylamine
For 7-7.5, there is solid precipitation immediately in beaker, be filtered by vacuum, be washed with distilled water precipitating 2-3 time, obtain crude product, vacuum is done
It is dry overnight.Gained crude product is through pillar layer separation (ethyl acetate:Petroleum ether=6:1, v:V), target chemical combination is obtained
3.4 g of object, yield 55%, mp> 300 ℃.
Embodiment 4.
Compound I to Co2+Ion recognition character：
Compound I is accurately weighed, uses tetrahydrofuran in 10 mL brown volumetric flasks:tris-HCl = 4: 6 (v :
V, pH=7.5）Buffer solution constant volume, be configured to 1.0 × 10-3 The stock solution of M.
Prepare Mg2+、Ca2+、Mn2+、Fe3+、Co2+、Ni2+、Cu2+、Zn2+、Sr2+、Cd2+、Ba2+、Hg2+、Pb2+、Bi3+14 kinds
The tetrahydrofuran of tested metal ion:tris-HCl = 4: 6 (v:V), the 1.0 × 10 of pH=7.5-3 The deposit of M
Liquid.
Prepare THF:Water=4: 6 (v:V), pH is respectively 1,2,3,4,5,6,7,8,9,10,11,
12,13 solution, error are ± 0.5.
Determine that compound I being capable of highly selective Co by ultraviolet spectra, fluorescence spectrum2+Ion.
Concrete operations are：
The 1.0 × 10 of 0.1 mL compound I are accurately measured with liquid-transfering gun-3 The stock solution of M moves into 15 10 mL browns and holds
In measuring bottle, first bottle contains only compound I, remaining is separately added into 0.5 mL metal ion stock solution, uses tetrahydrofuran:tris-
HCl = 4: 6 (v:V, pH=7.5）Solution constant volume.Compound is measured respectively, compound I and Mg2+、Ca2+、Mn2+、Fe3 +、Co2+、Ni2+、Cu2+、Zn2+、Sr2+、Cd2+、Ba2+、Hg2+、Pb2+、Bi3+Ultraviolet spectra, the fluorescence of the metal ion solution coexisted
Spectrum.
The ultraviolet spectra of compound I and Action of Metal Ions, fluorescence spectrum are shown in Fig. 2, Fig. 3.
Test shows compound I (10μM THF/)tris-HCl (4:6, v/ v, pH=7.5) blank is molten
5 times of equivalent Mg are added in compound I for liquid2+、Ca2+、Mn2+、Fe3+、Co2+、Ni2+、Cu2+、Zn2+、Sr2+、Cd2+、Ba2+、Hg2+、
Pb2+、Bi3+THF：H2O = 4: 6 (v:V, pH=7.5) in solution, remove Co2+Outside system, the ultraviolet suction of remaining solution
It is very weak to receive spectrum, the intensity of fluorescence emission spectrum.It joined Co2+THF：H2O= 4: 6 (v:V, pH=7.5) solution exists
Occur ultraviolet absorption peak at 520 nm and fluorescence signal significantly increases at 550 nm.This is because compound I and Co2+It generates
Open loop occurs for selective coordination effect, the spirocyclic lactams structure of compound I, and rhodamine parent oxa- anthracene nucleus generates quinoid knot
Structure, system have restored bigπKey conjugation, leads to have color change in visible region.Fig. 4, Fig. 5 are we can observe that contain Co2+'s
Compound I solution becomes orange red from colourless under white light and 254nm fluorescence respectively.
Embodiment 5.
Compound I is to Co2+When ion identification, Mg2+、Ca2+、Mn2+、Fe3+、Ni2+、Cu2+、Zn2+、Sr2+、Cd2+、Ba2+、Hg2 +、Pb2+、Bi3+ The interference elimination of 13 metal ion species：
Compound I, above-mentioned tested metal ion solution are prepared according to 4 method of embodiment.In compound I (10μM)
THF/ tris-HCl (4:6, v:V, pH=7.5) Co is added in solution2+ (50 μM) and be separately added into other metals from
Son (100μM).According to Fig. 7, Fig. 8 we can observe that, in the presence of having other metal ions, compound I still with Co2+
Significant change and intensity is presented hardly by other metal ion disturbances in generation effect, UV absorption and fluorescence emission spectrum.Card
Bright compound I is to Co2+ Show high selectivity.
Embodiment 6.
Compound I is to Co2+When ion identification, Co2+Concentration is to ultraviolet and fluorescence spectrum influence：
Compound I, tested Co are prepared according to 4 method of embodiment2+Solution.
Compound I original state is without ultraviolet, fluorescence signal.With Co2+The increase of solubility, ultraviolet and fluorescence signal increase therewith
By force, this illustrates Co2+Rhodamine lactams loop coil in inducing compounds I is opened.As the Co that 5 times of equivalents are added2+When it is ultraviolet and glimmering
There is maximum value in luminous intensity.Work as Co2+Solubility when continuing growing, ultraviolet and fluorescence intensity shows compound I almost without enhancing
With the Co of 5 times of equivalents2+Have reached saturation.Co2+Concentration is shown in Fig. 9, Figure 10 to ultraviolet and fluorescence influence.
Embodiment 7.
Compound I is to Co2+Ion identification pH fluorescence titration experiment：
We conducted soda acid fluorescence titrations to determine compound I to Co2+The optimum pH range of identification.It configures first dense
Degree is 1.0 × 10-3 mol·L-1Stock solution, use HCl and NaOH to configure the buffer solutions of different pH value as the molten of constant volume
Liquid.In Figure 11 fluorescence titration curve it is observed that compound I fluorescence signal occurs within the scope of pH 2-5, as addition Co2+Afterwards
The range of fluorescence enhancement is expanded to 2-8.This shows that compound I may be used as detecting Co within the scope of biological pH2+Fluorescent molecule visit
Needle.
Embodiment 8.
Compound I is applied to detect cobalt ions and its fluorescence imaging experiments in living cells：
By 1.5 × 10-5 mol·L-1(be derived from concentration is 1.0 × 10 to compound I-3mol·L-1Stock solution) be added to
It in cultured Hela Tissue Culture Dish, is cultivated 3.5 hours at 37 DEG C, solution in culture dish is sucked out, pure water washes three times, and every time 2
mL.Into the Tissue Culture Dish of the above-mentioned I containing compound, it is separately added into Co2+Concentration is 2.0 mL 1.5 × 10-5 mol·L-1 、
5.0 mL Co2+ 1.5×10-5 mol·L-1 (being derived from concentration is 1.0 × 10-3 mol·L-1Stock solution), enter incubator mistake
Night.As shown in figure 12, rhodamine characteristic fluorescence is presented in cell.It finds simultaneously, when concentration of metal ions increases, cell fluorescence intensity
It is consequently increased.
Compound can be used for the detection of cobalt ions and the cobalt ions fluorescence imaging in living biological cell in biosystem.
In conclusion compound I according to the present invention is a kind of cobalt ions fluorescence probe, it is sensitive with preferably detecting
Degree, the fluorescence emission wavelengths of compound I are between long wavelength region, wide in range suitable for pH range, therefore, can be used for living biological cell
Cobalt ions fluorescence imaging in middle cobalt ions detection and living biological cell.
Claims (4)
1. having structural formulaCompoundN'-(2- pyrazinyl)-ethylidene rhodamine 6G hydrazides
。
2. compound described in claim 1N'-(2- pyrazinyl)-ethylidene rhodamine 6G hydrazides preparation method, feature exists
It is carried out in by following step：
In organic solvent, rhodamine 6G hydrazides and acetyl group pyrazine are mixed, to sufficiently dissolve, second acid as catalyst are added,
Mixed system is heated to reflux to fully reacting, is cooled to room temperature to reaction system, mixed system is transferred to and fills ice water and mixes
In the beaker for closing object, adjusting solution ph with organic base is 7-7.5, and vacuum filtration is washed with distilled water precipitating, is slightly produced
Product are dried in vacuum overnight, and gained crude product is through pillar layer separation, eluant, eluent v:V is ethyl acetate:Petroleum ether=6:
1, obtain target compound；Wherein rhodamine 6G hydrazides：Acetyl group pyrazine：The molar ratio of catalyst is 1-1.2：1：0.1-
0.05；The organic solvent is methanol；The organic base is triethylamine.
3. compound N described in claim 1 '-(2- pyrazinyl)-ethylidene rhodamine 6G hydrazides is in preparation as to cobalt ions height
Application in terms of selective naked eye colour developing identification and fluorescence identifying probe.
It is detected 4. the preparation of compound N described in claim 1 '-(2- pyrazinyl)-ethylidene rhodamine 6G hydrazides is used as in living cells
Application in terms of cobalt ions and its fluorescence imaging probe.
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