CN106566531A - Preparation and analytical application of Rosamine fluorescence probe for detecting H2S - Google Patents
Preparation and analytical application of Rosamine fluorescence probe for detecting H2S Download PDFInfo
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Abstract
The invention discloses an azidated Rosamine (Ros-N3) fluorescence inductor. A synthetic method for the Ros-N3 fluorescence inductor is simple and comprises the following steps: with N-alkyl-m-aminophenol and p-nitrobenzaldehyde as raw materials, successively carrying out nitro reduction and amino azidation so as to obtain Ros-N3. Ros-N3 can selectively recognize H2S in a mixed aqueous solution (wherein a volume ratio of DMF to PB is 6: 4); after addition of HS<->, an ultraviolet spectrum undergoes a blue shift of 8 nm, fluorescence undergoes photoinduced electron transfer (PET), and fluorescence quenching occurs; after addition of other ions and biological mercaptan molecules (Cys, GSH and Hcy), the ultraviolet spectrum and fluorescence are free of obvious changes; and a detection limit is 3.5 ppm. High-resolution mass spectrometry proves that a reaction mechanism is reduction of azide into an amino group by H2S. Moreover, Ros-N3 is successfully applied to an experiment for identification of H2S in MGC-803 cells, so real-time detection of endogenous H2S in in-vivo cells with the probe is made possible, and Ros-N3 has potential application value.
Description
Technical field
The present invention relates to a kind of detection H2S Azide Luo Saming fluorescent probes（Ros-N3）Preparation and analysis application, belong to
Organic molecule fluorescent probe field.
Background technology
Hydrogen sulfide (H2S it is) a kind of gas with special odor, deep grinding has been obtained to the toxic pollutant of environment
Study carefully.Meanwhile, H2S is the endogenouss gas that the third can play physiological action in life body after carbon monoxide and nitric oxide
Body signaling molecule.Human endogenous' property H2S is mainly produced by the zymolysis of L-Cysteine.H2The scope of S physiological relevant concentrations
From nanomole level to a mM level level.Under physiological concentration level, H2S participates in a series of physiological regulating control process, example
Such as adjust antiotasises, myocardial contraction, nerve conduction and insulin secretion.If cell can not maintain its normal H2S is dense
Degree, will cause the disease such as tremulous pulse and pulmonary hypertension, Alzheimer's disease, gastric mucosa injury and liver cirrhosis.H2S can be with
Scavenger of ROS and active nitrogen species.Some common diseases such as A Er grows sea silent disease, Down's syndrome, diabetes and liver cirrhosis etc.
With endogenouss H2The regulation of S is disorderly related.Therefore, Selective recognition and the biological internal H of highly sensitive detection2S has particularly significant
Biomedical meaning.
At present, with colorimetry, electro chemical analysis, chromatography and metal sulfide precipitation etc. detection H2S technological means phases
Have that selectivity is good, sensitivity is high than, fluorescence probe method, and achievable real-time in-situ detection little to biological sample damage etc. solely
Special advantage.Intracellular H is detected using fluorescence probe method2The change of S concentration is one of Recent study focus.At present, H2S is glimmering
Light probe is developed by leaps and bounds at aspects such as design, mechanism of action and biologic applications.Using H2The strong reproducibility of S, energy will be glimmering
Azido or nitro in light probe structure is reduced into amino, causes its structural change, fluorescence properties also to change.Report
Many utilization H2The fluorescence probe of the reproducibility design of S.These probes some can realize H2The vitro detection of S, has
Intracellular H can be realized a bit2S detects that some can even realize the trace detection in subcellular organelle.But develop response
Faster, the molecular probe that phenomenon becomes apparent from, practicality is higher is still particularly significant.
The invention belongs to Luo Saming fluorescent probes, belongs to Rhodamine Derivatives Rh serial.Conventional synthesis rhodamine point
Preparative hplc is utilized mostly from isomer, the method high cost and can only obtain the product of milligram level.Replace anhydride using aldehyde
The pure rhodamine fluorescent dyes of synthesising different structure（That is Luo Saming dyestuffs）It is a kind of easy, inexpensive, the higher method of yield.The invention
Modified on the Luo Saming dyestuffs for obtaining, introduced Die nitrogen groups so as to which structural change, fluorescence properties can change.When
Front report with regard to Luo Saming dye fluorescent probes seldom, research and development are with good sieve of high sensitivity, high selectivity and application effect
Sa Ming fluorescent probes are significant.
The content of the invention
It is an object of the invention to deeply probe into and prepare with regard to Luo Saming fluorescent dyes and apply, a kind of detection H is proposed2S
Luo Saming fluorescent probes, can in cell Selective recognition H2S。
The general structure such as formula of the Luo Saming fluorescent dyes that the present invention is utilized（2）Shown, the amino reaction of 4 ' positions generates Die
Nitrilo, obtains target fluorescent probe, and the method is simple, and low raw-material cost；The alternative identification H of the probe2S, in DMF and
In the mixed solution of phosphate buffer, after adding NaHS, solution is clear purple by fluorescent material complexion changed, ultraviolet-visible spectrum
Blue shift 8nm；Lowest detection is limited to 0.34 μM, can be used for the intracellular H of MGC-8032The identification of S.
The preparation method of Azide Luo Saming fluorescent probe proposed by the present invention, the method synthesis is simple, low cost.Specifically
Step is as follows：Weigh amino Luo Saming compounds and be dissolved in methanol, add hydrochloric acid, be cooled to 0 DEG C, add NaNO2, mixture stirs
Mix 0.5 hour, be slowly added into NaN3, it is stirred at room temperature 5 hours.Suspension is extracted with dichloromethane, merges organic faciess, and vacuum is dense
Contracting.Cross pillar purification（Methanol：Dichloromethane=1:15, v/v）, gained Azide Luo Saming is darkviolet solid.
The invention provides the synthetic route of Die nitridation Luo Saming fluorescent probes is as follows：
The Ros-N that the present invention is provided3To H2The identification system of S is DMF/PB=6:4.
The present invention is to Ros-N3Fluorescence selectivity probed into, add H2After S, fluorescence is quenched.
The present invention is to Ros-N3Ultraviolet selectivity probed into, independent part ROSN3There is absorption maximum in 564nm, when
Add 10 equivalent HS-When, there is absorption maximum in 556nm.
The invention provides Ros-N3Response range to pH of test limit and probe.
The invention provides other ions（Cl-, F–,ClO-, AcO-, CO3 2-, HCO3 -,NO3 -, SO4 2-,HSO3 -,
SCN-, S2O3 2-, PO4 3-）With containing thiol derivative（Hcy, Cys, GSH）To Ros-N3H2The interference performance of S identifications.
The invention provides Ros-N3It is intracellular to H in MGC-8032The identification function of S.
It is an advantage of the invention that：The present invention is the H of Rhodamine Derivatives class2S fluorescent probes, it is serial to belong to Luo Saming, tool
Have the advantages that synthesis technique is simple, with low cost, easy to operate, selectivity is good, application prospect is extensive, at present relevant Luo Saming classes
Fluorescent probe document report is little.The invention has certain meaning to the photism Quality Research and understanding of Luo Saming dyestuffs.
The fluorescent probe can be in wider pH range to H2S is identified, and it is to the anti-of other small molecules in identification system or ion
Interference performance is strong, is a kind of efficient fluorescent quenching type H2S fluorescent probes, and it is successfully applied to H in living cells2The identification of S, be
Property H in Inner sources in real-time detection cell2S is provided may.
Description of the drawings
Come that the invention will be further described below in conjunction with the accompanying drawings：
Fig. 1 is compound R os-N in the embodiment of the present invention 33(10 μM) are with 10 equivalent aniones in DMF/ PB (6: 4 v/
UV absorption figure in the solution of v, 10 mM, pH=7.4).
Fig. 2 is compound R os-N in the embodiment of the present invention 33With 10 equivalent aniones in DMF/ PB (6: 4 v/v,10
MM, pH=7.4) fluorescent emission figure in solution.
Fig. 3 is compound R os-N in the embodiment of the present invention 33To H2The test limit figure of S.
Fig. 4 be in the embodiment of the present invention 3 other aniones to Ros-N3Identification H2The interference figure of S.
Fig. 5 be in the embodiment of the present invention 3 pH to Ros-N3Identification H2The impact figure of S.
Fig. 6 is Ros-N in the embodiment of the present invention 43The cell application drawing of fluorescent probe.
Specific embodiment
Such scheme is described further below in conjunction with specific embodiment, it will be appreciated that citing described herein is only
For explaining the present invention, it is not intended to limit the present invention.
Embodiment 1：Prepare Die nitridation rhodamine Ros-N3
Weigh 2-3g 3-（Diethylamine）Phenol and 1-2g paranitrobenzaldehydes are dissolved in 30-50 propanoic acid, add 0.1-0.2g to first
Base benzenesulfonic acid, flows back 16 hours under stirring at 65 DEG C.After reaction, mixed liquor is cooled to into room temperature, is added to the vinegar of 3mol/L
In acid sodium solution, float is extracted with dichloromethane solution, merges organic faciess, and removes propanoic acid with water back extraction.Use anhydrous slufuric acid
Sodium is dried, concentration.Gained solid is dissolved in the mixed liquor of methanol and dichloromethane（1:1）.1-1.5g chloranils are added, soon
Speed stirring 2 hours, it is concentrated in vacuo.Gradient crosses pillar purification（Dichloromethane：Methanol=50:1-9:1, v/v）.Obtain purple nitro
Luo Saming compounds, the % of yield 13.
Weigh 0.4-0.6g nitro Luo Saming compounds to be dissolved in 20-40mL methanol, add 0.6-0.8g SnCl2With
1mL hydrochloric acid, the lower backflow of stirring 15 hours.Mixed liquor is cooled to room temperature, concentrated in vacuo.Products therefrom is purified through column chromatography（Two
Chloromethanes：Methanol=10:1, v/v）, obtain mulberry amino Luo Saming, yield 58%.
Weigh 0.2-0.3g amino Luo Saming compounds and be dissolved in 10-20mL methanol, add 3mL hydrochloric acid, be cooled to 0 DEG C, plus
Enter 0.05-0.1g NaNO2, mixture stir 0.5 hour, be slowly added into 0.05-0.1g NaN3, it is stirred at room temperature 5 hours.Suspend
Liquid is extracted with dichloromethane, merges organic faciess, concentrated in vacuo.Cross pillar purification（Methanol：Dichloromethane=1:15, v/v）, gained
For darkviolet solid Azide Luo Saming, yield 68.4%.As a result it is as follows：
1H NMR (400MHz, CDCl3, ppm):1.31 (t, 12H, J=6.8Hz), 3.65 (q, 8H, J=
6.4Hz), 6.77 (s, 2H), 6.96 (d, 2H, J=8.8), 7.25 (d, 2H, J=8.0), 7.31 (d, 2H,J=10.4), 7.38 (t, 2H, J=7.8)
13C NMR (100MHz, CDCl3) δ (ppm):12.66 , 46.20 , 96.47 , 113.18 , 144.42 ,
119.61 , 128.09 , 131.21 , 131.82 , 142.54 , 155.49 , 156.20 , 157.90.
HR-MS:440.2448
Embodiment 2：Solution is prepared
The preparation of solution：The reagent used in experiment is analyzes pure, does not further process, and directly uses；The water used is two
Secondary high purity water, by Milli-Q water purification machine purification.
The preparation of 1mM part standard solution：Degree of accuracy for a ten thousandth gram analytical balance, accurate Weigh Compound Ros-
N3Solid in the volumetric flask of 10 mL, methanol constant volume is configured to the base soln of 1mM.
The preparation of 10mM anion standard solution：It is similar to configuration part standard solution, accurately weigh one with analytical balance
The sodium salt of quantitative various aniones in the volumetric flask of 10 mL, high purity water constant volume, it is the molten of 10 mmol/L to be configured to concentration
Liquid.
In identification system, ligand concentration is 10 μM, and interfering ion and NaHS concentration are 100 μM.
Embodiment 3：Spectrum Analysis
Independent part Ros-N3There is absorption maximum in 564nm, as 10 equivalent HS of addition-When, there is absorption maximum in 556nm.But work as
Add other ions of 10 equivalents（Br-, Cl-, F–,ClO-, AcO-, CO3 2-, HCO3 -,NO3 -, SO4 2-,HSO3 -, SCN-,
S2O3 2-, PO4 3-）With containing thiol derivative（Hcy, Cys, GSH）When, not particularly apparent uv absorption change.By with
Knowable to upper result, ROSN3In DMF/ PB (6:To HS in the system of 4 v/v, 10 mM, pH=7.4)-Have good ultraviolet
Absorption selectivity, is as a result shown in Fig. 1.
Probe Ros-N3There is notable fluorescence at 589nm, when adding 10 equiv.HS-When, fluorescent quenching.But work as and add it
When its ion and biological micromolecule, not particularly apparent change in fluorescence.From above-mentioned experimental result, ROSN3In DMF/
PB(6 :To HS in the system of 4 v/v, 10 mM, pH=7.4)-The fluorescence selectivity having had, is as a result shown in Fig. 2.
Solid ligand concentration is that (10 μM) are constant in buffer solution DMF/ PB, with HS-Ion concentration increases, fitting
Linear equation Y=168.04-57.35X, R2=0.9954, it is computed detection and is limited to 0.34 μM, see Fig. 3.
The HS of 10 equivalents of each addition in part (10 μM) and the various solions of 10 equivalents-, then survey its fluorescence and send out
Penetrate spectrum.As shown in Figure 3, other ion-pair compounds Ros-N3Identification HS-Without substantially interfering with, Fig. 4 is seen.
The buffer solution of pH=4-8 is prepared, after adding part, fluorescence is unchanged；Add timing body and 10 equiv.HS-
When, fluorescent quenching.Show the probe in the range of pH=4-8, to H2The identification of S does not produce impact, as a result sees Fig. 5.
Embodiment 4：Cell experiment
To probe Ros-N3HS is detected in MGC-803 cells-Cell imaging experiment is carried out.Cell experiment step is as follows：
10 μM of Ros-N is initially charged in MGC-803 cells3Probe solution, is incubated 30 min, respectively in natural light under the conditions of 37 DEG C
It is imaged with HONGGUANG.Such as b in Fig. 6, can be observed have intense red fluorescence.Then wash twice, then 10 μM of the addition toward system
HS-It is incubated under solution, the same terms after 30 min and is imaged.Such as Fig. 6 d, it can be seen that intracellular almost unstressed configuration.A and c are
Ros-N3、Ros-N3+HS-Cell imaging under natural light, cellular morphology is good, illustrates probe and the HS for adding-Ion is not
Irreversible injury is formed to cell.Ros-N3Can apply to intracellular detection HS-, illustrate that the probe has potential using value.
Above-described embodiment technology design only to illustrate the invention and feature, its object is to allow person skilled in the art
Understand present disclosure and implement according to this, can not be limited the scope of the invention with this.It is all real according to spirit of the invention
Equivalent transformation or modification that matter is done, all should be included within the scope of the present invention.
Claims (4)
1. a kind of Azide Luo Saming fluorescent probe Ros-N3, its structural formula such as formula（1）It is shown：
Azide Luo Saming fluorescent probe Ros-N described in claim 13Preparation method, including：
Amino Luo Saming compounds are dissolved in into methanol, hydrochloric acid is added, 0 DEG C is cooled to, NaNO is added2, it is little that mixture stirs 0.5
When, it is slowly added into NaN3, it is stirred at room temperature 5 hours, obtain darkviolet solid Azide Luo Saming.
2. the preparation method according to right 1, it is characterised in that：
Preparing Ros-N3Also include isolating and purifying Ros-N after the step of compound3The step of compound：By the Ros- of gained
N3Compound crude product is isolated and purified, and Ros-N is obtained3Pure compounds.
3. Ros-N described in claim 13Application in as fluorescent probe.
4. the application described in claim 4, it is characterised in that：By Ros-N3Compound is used for H as fluorescent probe2The detection of S.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107418556A (en) * | 2017-05-31 | 2017-12-01 | 济南大学 | A kind of fluorescence probe for detecting hydrogen sulfide and its preparation method and application |
| CN109575914A (en) * | 2018-11-02 | 2019-04-05 | 大连医科大学 | A kind of application detecting 2 fluorescence probe of N-acetyl-transferase |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104804725A (en) * | 2014-01-28 | 2015-07-29 | 中国科学院大连化学物理研究所 | Fluorescent probe for detecting H2S in lysosome and its synthesis method and use |
| CN105131941A (en) * | 2015-09-23 | 2015-12-09 | 山东理工大学 | Endogenous H2S detecting fluorescence probe and preparation method thereof |
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2016
- 2016-07-07 CN CN201610527103.2A patent/CN106566531A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104804725A (en) * | 2014-01-28 | 2015-07-29 | 中国科学院大连化学物理研究所 | Fluorescent probe for detecting H2S in lysosome and its synthesis method and use |
| CN105131941A (en) * | 2015-09-23 | 2015-12-09 | 山东理工大学 | Endogenous H2S detecting fluorescence probe and preparation method thereof |
Non-Patent Citations (1)
| Title |
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| J. CHENG ET AL.，: ""A new rosamine-based fluorescent chemodosimeter for hydrogen sulfide and its bioimaging in live cells"", 《NEW J. CHEM.》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107418556A (en) * | 2017-05-31 | 2017-12-01 | 济南大学 | A kind of fluorescence probe for detecting hydrogen sulfide and its preparation method and application |
| CN107418556B (en) * | 2017-05-31 | 2019-10-25 | 济南大学 | A kind of fluorescence probe and its preparation method and application detecting hydrogen sulfide |
| CN109575914A (en) * | 2018-11-02 | 2019-04-05 | 大连医科大学 | A kind of application detecting 2 fluorescence probe of N-acetyl-transferase |
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