CN104419401A - Fluorescent probe for detecting hydrogen sulfide by virtue of fluorescence enhancement as well as synthetic method and application of fluorescent probe - Google Patents
Fluorescent probe for detecting hydrogen sulfide by virtue of fluorescence enhancement as well as synthetic method and application of fluorescent probe Download PDFInfo
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- CN104419401A CN104419401A CN201310381224.7A CN201310381224A CN104419401A CN 104419401 A CN104419401 A CN 104419401A CN 201310381224 A CN201310381224 A CN 201310381224A CN 104419401 A CN104419401 A CN 104419401A
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- hydrogen sulfide
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- VNFZWFKLIHBEBP-MARXPDLDSA-N CC(C)/C(/C)=C/C(C1=CCCC[C@]1(C)O)=O Chemical compound CC(C)/C(/C)=C/C(C1=CCCC[C@]1(C)O)=O VNFZWFKLIHBEBP-MARXPDLDSA-N 0.000 description 1
Abstract
The invention relates to a fluorescence enhancement type hydrogen sulfide fluorescent probe and particularly relates to a fluorescence enhancement type hydrogen sulfide fluorescent probe based on flavone derivatives. Flavone derivatives are directly reacted with 2,4-dinitrofluorobenzene, and a reaction product is subjected to column chromatography to generate a pure probe product. According to the fluorescence enhancement type hydrogen sulfide fluorescent probe, probe molecules have the maximum absorption wavelengths of 460nm, relatively good solubility in a 1.5mM CTAB water solution and stable optical performance; by adding the probe molecules together with hydrogen sulfide, the absorption wavelengths are blueshifted from 460nm to 450nm, and the intensity of a fluorescence spectrum is continuously enhanced at 612nm and is maximally enhanced by 96 times. According to the fluorescence enhancement type hydrogen sulfide fluorescent probe, the deficiencies that an existing fluorescent probe is slow in response to hydrogen sulfide and high in detection line, and detection wavelengths are in a visible light region are overcome; the probe molecules are high in sensitivity, stable in optical performance, relatively high in synthetic yield, strong in capability of identifying hydrogen sulfide, high in response speed, wide in detection range and low in detection lower limit, the response range is 0-50 mu M, and the detection limit is 0.09 mu M; therefore, the fluorescent probe has practical application values in the fields of biological chemistry, environmental science and the like.
Description
Technical field
What the present invention relates to is chemical analysis detection technique field, is specifically related to preparation method and the application of this fluorescent probe in detection hydrogen sulfide that a kind of Fluorescence Increasing detects hydrogen sulfide fluorescent probe.
Background technology
Hydrogen sulfide, the rotten egg smell unpleasant because of it and well-known, is regarded as a kind of toxic gas traditionally.Nearest research shows, hydrogen sulfide is a kind of endogenous gas signal compound, and its biological importance is equal to other known endogenous gas signaling molecule carbon monoxide and nitrogen protoxides.Hydrogen sulfide has been identified and has played regulating effect in many bioprocess.Research shows; as the switch of K-ATP passage; hydrogen sulfide can affect cardiovascular systems; in treatment ischemic heart failure, by and response of anti-apoptotic signal anti-oxidant in conjunction with it, hydrogen sulfide plays active protection effect; simultaneously; hydrogen sulfide is to central nervous system, and respiratory system, gastrointestinal system and endocrine system all have regulating power.Hydrogen sulfide has similar nitric oxide production plurality of advantages and does not produce poisonous active oxygen species, the more important thing is, it can also as the scavenging agent of antioxidant or active oxygen species.Research display, mongolism and alzheimer disease are all the diseases relevant to hydrogen sulfide levels.Therefore, interest is put in the physiological and pathological function understanding hydrogen sulfide by increasing in recent years researcher.（Beauchamp R O, Bus J B, Popp J A, Boreiko C J, Andjelkovich D A, Leber P. A Critical Review of the Literature on Hydrogen Sulfite Toxicity. [J] Critical Reviews in Toxicology 1984; 13(1): 25-97. Kimura H, Nagai Y, Umemura K, Kimura Y. Physiological Roles of Hydrogen Sulfide: Synaptic Modulation, Neuroprotection, and Smooth Muscle Relaxation. [J] Antioxidants & Redox Signaling 2005; 7(5-6): 795-803. Kabil O, Banerjee R. Redox Biochemistry of Hydrogen Sulfide. [J] The Journal of Biological Chemistry 2010; 285(29): 21903-21907.）。
Up to now, for the research of hydrogen sulfide, colorimetry, electrochemical analysis, chromatography is in the news all, but hydrogen sulfide decomposes rapidly, causes the continued jitters of concentration, be difficult to realize accurate detection, and these methods is not suitable for the detection in coenocorrelation.By contrast, fluorescent probe is due to sensitive, and fast, method is convenient, may be used for active somatic cell and detects, be widely used in the detection of many materials.Therefore, set up fast, accurately, the method that real-time fluorescence detects hydrogen sulfide has become the focus that people attract attention.（Choi M G, Cha S, Lee H, Jeon H, Chang S K.Sulfide-selective chemosignaling by a Cu2+ complex of dipicolylamine appended fluorescein. [J] Chemical Communication 2009; 47: 7390-7392. Searcy D G, Peterson M A. Hydrogen sulfide consumption measured at low steady state concentrations using a sulfidostat. [J] Analytical Biochemistry 2004; 324(2): 269-275. Radford-Knoery J, Cutter G A. Determination of carbonyl sulfide and hydrogen sulfide species in natural waters using specialized collection procedures and gas chromatography with flame photometric detection. [J] Analytical Chemistry 1993; 65(8): 976-982.）。
The fluorescent probe that great majority have been reported is only embodied in visible region to hydrogen sulfide containing response, and background interference is larger, and simultaneously comparatively slow to the response speed of hydrogen sulfide, detectability is higher.Therefore, design is a kind of fast, sensitive, and the fluorescent probe relatively grown of determined wavelength is of great significance for the detection tool of hydrogen sulfide.
Summary of the invention
For above-mentioned situation, an object of the present invention provides a kind of and synthesizes simple, gentle, the lower-cost fluorescent probe synthetic method of reaction conditions; It is good that two of object is to provide a kind of selectivity, highly sensitive, can detect hydrogen sulfide containing fluorescent probe by Fluorescence Increasing.
The present invention uses Fluorescence Increasing to detect hydrogen sulfide fluorescent probe, adopt flavone derivative and DNF to synthesize in the presence of base, and 2,4-dinitrobenzene ether moiety is as recognition group.
The present invention's technical scheme taked of dealing with problems is, a kind of Fluorescence Increasing detects hydrogen sulfide fluorescent probe, has following structural:
The building-up reactions equation of this fluorescent probe is as follows:
Concrete preparation method comprises the following steps:
1) by 4-dimethylaminocinnamaldehyde, o-hydroxyacetophenone and sodium hydroxide are dissolved in methyl alcohol, reflux 5 hours, after having reacted, are poured into by reaction solution in frozen water, acidifying, separate out solid, filter, and collect solid, ethyl alcohol recrystallization.Obtain product and be compound 3.
2) under ice bath, the sodium hydroxide solution of compound 3 and 20% is dissolved in methyl alcohol, after returning to room temperature, in reaction solution, drips hydrogen peroxide, heat up and stir.After having reacted, be down to room temperature, be poured into water, separate out solid, filter, collect solid.Obtain product and be compound 2.
3) by compound 2, DNF and salt of wormwood two are dissolved in acetonitrile, backflow.After having reacted, be down to room temperature, be poured into water, dichloromethane extraction, anhydrous sodium sulfate drying, column chromatography for separation obtains product and is probe compound.Synthesis and the detection method of this probe is illustrate in greater detail in the embodiment of this specification sheets.
Fluorescent molecular probe using method of the present invention is not particularly limited.Usually probe molecule can be dissolved in hexadecyl brometo de amonio (CTAB) and the aqueous solution, test under room temperature.When adding hydrogen sulfide; because hydrogen sulfide can by 2; the hydroxyl of 4-dinitrofluorobenzene protection sloughs protection (see following formula); and then interrupted the cancellation effect of nitro to probe compound; Photo-induced electron transfer effect (PET) is suppressed; thus make the Fluorescence Increasing of probe, on fluorescence spectrum, produce significantly change simultaneously.
The specific features that Fluorescence Increasing of the present invention detects hydrogen sulfide fluorescent probe is as follows:
Probe molecule maximum absorption wavelength, at 460 nm, does not almost observe fluorescence in fluorescence spectrum; Probe solvability in the 1.5 mM CTAB aqueous solution is better, and along with adding of hydrogen sulfide, probe molecule declines gradually in the maximum absorption at 460nm place, the absorption peak that 450 nm place appearance one is simultaneously new, and absorption spectrum blue shift is about 10 nm; In fluorescence spectrum, there is maximum emission peak in 600 nm places, and along with the increase of concentration of hydrogen sulfide, its fluorescence intensity also increases thereupon, maximumly can strengthen 96 times.Under the irradiation of ultraviolet lamp, probe presents stronger red fluorescence.
Probe molecule sensitivity of the present invention is higher, stable optical performance, raw material is easy to get, and synthetic yield is higher, strong to hydrogen sulfide recognition capability, fast response time, responding range is 0-50 μM, detects and is limited to 0.09 μM, sensing range is wide, Monitoring lower-cut is low, makes the type probe in biological chemistry, and the fields such as environmental science have actual using value.
Accompanying drawing explanation
Fig. 1 is that fluorescent probe of the present invention is in 7.0 PBS systems, ultra-violet absorption spectrum changing conditions before and after fluorescent probe and NaHS react, line of dots represents the ultra-violet absorption spectrum of fluorescent probe, asterisk line represents fluorescent probe and the reacted ultra-violet absorption spectrum of NaHS, X-coordinate is wavelength, and ordinate zou is absorbancy.
Fig. 2 be fluorescent probe of the present invention in 7.0 PBS systems, fluorescent probe and the reacted fluorescence emission spectrum changing conditions of different concns NaHS, X-coordinate is wavelength, and ordinate zou is fluorescence intensity.
Fig. 3 be fluorescent probe of the present invention in 7.0 PBS systems, fluorescent probe and the reacted fluorescence emission spectrum changing conditions of different concns NaHS, X-coordinate is the concentration of NaHS, and ordinate zou is fluorescence intensity.Insert pictures is the reacted fluorescence intensity change situation of fluorescent probe and small concentration NaHS, and X-coordinate is the concentration of NaHS, and ordinate zou is fluorescence intensity.
Fig. 4 be fluorescent probe of the present invention in 7.0 PBS systems, fluorescent probe tester (F different from isoconcentration
-, Cl
-, Br
-, I
-, H
2pO
4 -, NO
3 -, NO
2 -, OAc
-, HCO
3 -, N
3 -, SO
4 2-, SO
3 2-, S
2o
3 2-, S
2o
4 2-, ClO
-, SCN
-, CN
-, citrate, H
2o
2, Cys, GSH, NAC, Ca
2+, Cu
2+, Fe
3+, Mg
2+, Zn
2+, NaHS) reacted fluorescence intensity change situation, X-coordinate is ion, and ordinate zou is fluorescence intensity.
Fig. 5 be fluorescent probe of the present invention in 7.0 PBS systems, interfering substance exist under after, fluorescent probe and the reacted fluorescence intensity change situation of NaHS, X-coordinate is the material added, and ordinate zou is fluorescence intensity ratio (I
1+NaHS+-SH/ I
1+NaHS).
Fig. 6 be fluorescent probe of the present invention in 7.0 PBS systems, after fluorescent probe reacts from the NaHS of different equivalent, fluorescence intensity is situation over time, and X-coordinate is the time, and ordinate zou is fluorescence intensity.
Fig. 7 be fluorescent probe of the present invention in 7.0 PBS systems, before and after fluorescent probe and NaHS react, fluorescence intensity is with the changing conditions of different pH, and X-coordinate is pH, and ordinate zou is fluorescence intensity.
Fig. 8 is the proton nmr spectra of the compound 3 that the present invention synthesizes.
Fig. 9 is the proton nmr spectra of the compound 2 that the present invention synthesizes.
Figure 10 is the proton nmr spectra of the fluorescent probe that the present invention synthesizes.
Embodiment
embodiment 1: the preparation of compound 3
In the mono-neck flask of 100 mL, add 4-dimethylaminocinnamaldehyde (0.35 g, 2 mmol), o-hydroxyacetophenone (0.27 g. 2 mmol) and sodium hydroxide (0.2 g, 5 mmol) are dissolved in 20 ml methyl alcohol, temperature rising reflux 5 hours.After having reacted, be cooled to room temperature, reaction solution poured in frozen water, about salt acid for adjusting pH value to 2, separate out a large amount of solid.Suction filtration, collects solid, dry, ethyl alcohol recrystallization.Obtain solid product 0.38 g(yield: 65 %) be compound 2.
δ
H(400 MHz, CDCl
3): δ 7.83 (dd,
J= 8.1, 1.3 Hz, 1H), 7.74 (dd,
J= 14.5, 11.2 Hz, 1H), 7.48 – 7.39 (m, 3H), 7.11 (d,
J= 14.5 Hz, 1H), 7.04 – 6.97 (m, 2H), 6.94 – 6.83 (m, 2H), 6.70 (d,
J= 7.7 Hz, 2H), 3.03 (s, 6H)。
embodiment 2: the preparation of compound 2
Under ice bath, the sodium hydroxide solution of compound 3 (293 mg, 1 mmol) and 2 mL 20% is dissolved in 20 mL methanol solutions, in reaction solution, drips the hydrogen peroxide of 1 mL 30 %.After dropwising, be warming up to back flow reaction 3 hours.After having reacted, be down to room temperature, separate out precipitation.Collecting precipitation, it is compound 2 that drying both obtains product.175 mg(yields: 57 %)
1H NMR (400 MHz, DMSO-
d 6) δ 7.95 (d,
J= 8.4 Hz, 1H), 7.43 (dd,
J= 17.0, 9.1 Hz, 3H), 7.34 (d,
J= 8.8 Hz, 2H), 7.17 (ddd,
J= 7.9, 5.0, 2.9 Hz, 1H), 6.97 (d,
J= 16.2 Hz, 1H), 6.66 (d,
J= 8.8 Hz, 2H), 2.88 (s, 6H)。
embodiment 3: the preparation of fluorescent probe
By compound 2 (31 mg, 0.1 mmol), DNF (22 mg, 0.12 mmol) and salt of wormwood (17 mg, 0.12 mmol) are dissolved in 10 ml acetonitriles, reflux 8 hours.Cooling, be poured into water, dichloromethane extraction, anhydrous sodium sulfate drying, column chromatography for separation (methylene dichloride) obtains product 36 mg(yield: 76 %) be probe compound.
1H NMR (400 MHz, DMSO-
d 6) δ 9.33 (d,
J= 2.7 Hz, 1H), 8.76 (dd,
J= 9.3, 2.8 Hz, 1H), 8.45 (d,
J= 7.9 Hz, 1H), 8.35 – 8.16 (m, 3H), 8.01 (d,
J= 8.8 Hz, 2H), 7.93 (t,
J= 8.8 Hz, 2H), 7.41 (d,
J= 15.9 Hz, 1H), 7.16 (d,
J= 8.8 Hz, 2H), 2.92 (s, 6H)。
embodiment 4: Fluorescence Increasing detects the application of hydrogen sulfide fluorescent probe
This probe is dissolved in the PBS containing 1.5 mM CTAB, is mixed with 10 × 10
-6the solution of M, adds the hydrogen sulfide solution of 50 μMs, ultra-violet absorption spectrum before and after test reaction; By in water-soluble for this probe molecule solution, concentration is 10 μMs, adds the different tester (F of 1 mM of isoconcentration respectively
-, Cl
-, Br
-, I
-, H
2pO
4 -, NO
3 -, NO
2 -, OAc
-, HCO
3 -, N
3 -, SO
4 2-, SO
3 2-, S
2o
3 2-, S
2o
4 2-, ClO
-, SCN
-, CN
-, citrate, H
2o
2, Cys, GSH, NAC, Ca
2+, Cu
2+, Fe
3+, Mg
2+, Zn
2+) solution, test the change of its fluorescence emission spectrum.Further, by water-soluble for this probe molecule solution, concentration is 1 μM, add the solution of 50 μMs of concentration of hydrogen sulfide, add the interfering substance (Cys, GSH and NAC) of 20 equivalents simultaneously, test the change of its fluorescence emission spectrum.Fig. 1-Fig. 7 shows, in UV spectrum and fluorescence spectrum, fluorescent probe molecule has very high selectivity to hydrogen sulfide, along with adding of hydrogen sulfide, the ultra-violet absorption spectrum of reaction system is blue shifted to 450 nm by 460 nm, the fluorescence spectrum display of system simultaneously, fluorescence peak at 612 nm places significantly strengthens with the increase intensity of concentration of hydrogen sulfide, and fluorescence intensity strengthens as original 96 times.And this fluorescent probe molecule is to other related anion (F
-, Cl
-, Br
-, I
-, H
2pO
4 -, NO
3 -, NO
2 -, OAc
-, HCO
3 -, N
3 -, CN
-, SO
4 2-), metal ion (Ca
2+, Cu
2+, Fe
3+, Mg
2+, Zn
2+), redox reagent (SO
3 2-, S
2o
3 2-, S
2o
4 2-, OCl
-, SCN
-, citrate, H
2o
2) all without obviously response.Even if relevant to biology containing under sulfydryl small molecules (Cys, GSH, NAC) existent condition at some, this fluorescent probe also can not be subject to significant interference to the detection of hydrogen sulfide.
Claims (3)
1. the present invention relates to preparation method and the application of this fluorescent molecular probe in detection hydrogen sulfide that a kind of Fluorescence Increasing detects hydrogen sulfide fluorescent molecular probe, it is characterized in that there is the chemical structural formula in formula I:
Formula I
The fluorescent probe of described detection hydrogen sulfide take flavone derivative as fluorophore, and 2,4-dinitrodiphenyl ether is the compound of hydrogen sulfide recognition group.
2. the Fluorescence Increasing based on flavone derivative according to claim 1 detects the fluorescent molecular probe of hydrogen sulfide, it is characterized in that this synthetic method is carried out as follows:
1) by 4-dimethylaminocinnamaldehyde, o-hydroxyacetophenone and sodium hydroxide are dissolved in methyl alcohol, reflux 5 hours, after having reacted, reaction solution is poured in frozen water, acidifying, separate out solid, filter, collect solid, ethyl alcohol recrystallization, obtains the compound 3 with chemical molecular structure in formula II;
Formula II
2) under ice bath, the sodium hydroxide solution of compound 3 and 20% is dissolved in methyl alcohol, after returning to room temperature, in reaction solution, drips hydrogen peroxide, heat up and stir; After having reacted, be down to room temperature, be poured into water, separate out solid, filter, collect solid, obtain the compound 2 with chemical molecular structure in formula III;
Formula III
3) by compound 2, DNF and salt of wormwood two are dissolved in acetonitrile, backflow; After having reacted, be down to room temperature, be poured into water, dichloromethane extraction, anhydrous sodium sulfate drying, column chromatography for separation obtains product and is probe compound.
3. bore hole identification according to claim 1 and Fluorescence Increasing detect the application of hydrogen sulfide fluorescent molecular probe, and it is characterized in that the mensuration for hydrogen sulfide content, concrete grammar is as follows:
Configure the aqueous solution of molecular probe of the present invention, concentration is 10 μMs, make a series of (1,2,3,4,5,6,7,8,9,10,15,20,30,40, the 50 μM) standardized solution with different concentration of hydrogen sulfide, place after 20 minutes, under 450 nm excitation wavelengths, measure the fluorescence intensity of this serial solution, draw fluorogram, record the fluorescent emission intensity at each comfortable 612 nm places, make typical curve, the funtcional relationship of matching determination fluorescence intensity and concentration of hydrogen sulfide.
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| CN104860840A (en) * | 2015-04-27 | 2015-08-26 | 苏州罗兰生物科技有限公司 | Preparation and application of fluorescence enhancement type hydrogen sulfide fluorescent probe |
| CN105038763A (en) * | 2015-06-04 | 2015-11-11 | 济南大学 | Fluorescent probe for identifying hydrogen sulfide in lysosome and application thereof |
| CN106700038A (en) * | 2016-12-21 | 2017-05-24 | 北京化工大学 | Method for detecting gas signal molecule H2S through fluorescent probe |
| CN107290323A (en) * | 2017-08-10 | 2017-10-24 | 台州学院 | A kind of near infrared fluorescent probe and preparation method and application technology |
| CN107383037A (en) * | 2017-07-18 | 2017-11-24 | 渤海大学 | A kind of long wave elongated H2S fluorescence probes and its synthetic method and application |
| CN109320460A (en) * | 2018-10-12 | 2019-02-12 | 江苏大学 | A kind of detection H2Fluorescence probe of S and its preparation method and application |
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| CN113024504A (en) * | 2021-03-12 | 2021-06-25 | 湘潭大学 | Preparation and application of hydrogen sulfide fluorescent probe based on isophorone-xanthene |
| CN114805262A (en) * | 2022-05-05 | 2022-07-29 | 曲阜师范大学 | Viscosity and polarity response type platform fluorescent probe, hydrogen sulfide detection fluorescent probe, synthesis process and application thereof |
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| CN117024395A (en) * | 2023-06-19 | 2023-11-10 | 西北大学 | Be used for detecting H 2 S flavonol derivative fluorescent probe and preparation method and application thereof |
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| CN104860840A (en) * | 2015-04-27 | 2015-08-26 | 苏州罗兰生物科技有限公司 | Preparation and application of fluorescence enhancement type hydrogen sulfide fluorescent probe |
| CN105038763A (en) * | 2015-06-04 | 2015-11-11 | 济南大学 | Fluorescent probe for identifying hydrogen sulfide in lysosome and application thereof |
| CN106700038A (en) * | 2016-12-21 | 2017-05-24 | 北京化工大学 | Method for detecting gas signal molecule H2S through fluorescent probe |
| CN107383037A (en) * | 2017-07-18 | 2017-11-24 | 渤海大学 | A kind of long wave elongated H2S fluorescence probes and its synthetic method and application |
| CN107383037B (en) * | 2017-07-18 | 2019-09-20 | 渤海大学 | A kind of long wave elongated H2S fluorescence probe and its synthetic method and application |
| CN107290323A (en) * | 2017-08-10 | 2017-10-24 | 台州学院 | A kind of near infrared fluorescent probe and preparation method and application technology |
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| CN109796962B (en) * | 2019-01-16 | 2021-05-25 | 中南大学 | Specific type fluorescent probe with large Stokes displacement for detecting hypochlorous acid |
| CN109796962A (en) * | 2019-01-16 | 2019-05-24 | 中南大学 | There is one kind big stoke shift to detect hypochlorous ratio type fluorescence probe |
| CN113024504A (en) * | 2021-03-12 | 2021-06-25 | 湘潭大学 | Preparation and application of hydrogen sulfide fluorescent probe based on isophorone-xanthene |
| CN113024504B (en) * | 2021-03-12 | 2022-04-05 | 湘潭大学 | Preparation and application of hydrogen sulfide fluorescent probe based on isophorone-xanthene |
| CN114805262A (en) * | 2022-05-05 | 2022-07-29 | 曲阜师范大学 | Viscosity and polarity response type platform fluorescent probe, hydrogen sulfide detection fluorescent probe, synthesis process and application thereof |
| CN114805262B (en) * | 2022-05-05 | 2024-03-26 | 曲阜师范大学 | Viscosity and polarity response type platform fluorescent probe, hydrogen sulfide detection fluorescent probe, and synthesis process and application thereof |
| CN117024395A (en) * | 2023-06-19 | 2023-11-10 | 西北大学 | Be used for detecting H 2 S flavonol derivative fluorescent probe and preparation method and application thereof |
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Application publication date: 20150318 |