CN106518855B - It is a kind of using half river cyanines and flavonols as the Sulfur Dioxide-derivatives scale fluorescence probe of fluorogen and its application - Google Patents
It is a kind of using half river cyanines and flavonols as the Sulfur Dioxide-derivatives scale fluorescence probe of fluorogen and its application Download PDFInfo
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- CN106518855B CN106518855B CN201610976291.7A CN201610976291A CN106518855B CN 106518855 B CN106518855 B CN 106518855B CN 201610976291 A CN201610976291 A CN 201610976291A CN 106518855 B CN106518855 B CN 106518855B
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- 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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- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
The invention discloses a kind of using half river cyanines and flavonols as the Sulfur Dioxide-derivatives scale fluorescence probe of fluorogen, the fluorescence probe is formed by connecting with half river cyanines fluorogen by non-conjugated by flavonols fluorogen, it is named as L-HF1, shown in chemical structural formula such as formula (I).The invention also discloses the applications of Sulfur Dioxide-derivatives of the fluorescence probe in detection liquid or cell.Experiment confirms acting on Sulfur Dioxide-derivatives for the probe property of can choose of the invention, test system is set to be become colorless by red, so that detection naked eyes are distinguishable, and fluorescence becomes green from red, these phenomenons can be analyzed by UV absorption instrument and sepectrophotofluorometer.Meanwhile the fluorescence probe disclosed by the invention can realize the high sensitivity detection to trace sulfur dioxide derivative, have important application value.
Description
Technical field
The present invention relates to the Sulfur Dioxide-derivatives scale fluorescence probes that a kind of half river cyanines and flavonols are fluorogen, especially
It is related to a kind of fluorescence probe that can detect liver cancer cells endogenous sulfur dioxide derivative and its application；It is glimmering to belong to small organic molecule
Light probe technical field.
Background technique
Flavonols is with ESIPT (excited state intramolecular proton transfer) phenomenon, fluorescence quantum yield with higher
Fluorescence structure, be critically important Green fluorescent dye, by modification after for luminescent material, chemical sensor and label life
Object molecule.It is studied and is continued to develop using the Sulfur Dioxide-derivatives in change in fluorescence detection active somatic cell in recent years.
Cell generates Sulfur Dioxide-derivatives under the action of can use the substrates such as cysteine and desmoenzyme --- and it is sub-
Sulfate and bisulfites may participate in intracellular various physiological processes, for example change heart rate, reduce blood pressure and participate in inflammation and is anti-
It should wait.But Sulfur Dioxide-derivatives too high levels can cause a series of adverse reactions in vivo, cause damages to human health.Together
When, sulfur dioxide is very harmful air pollutants.So the accurate detection and control to it have great importance.
Summary of the invention
The problem to be solved in the present invention is to provide a kind of using half river cyanines and flavonols as the Sulfur Dioxide-derivatives of fluorogen
Scale fluorescence probe, and the probe is with highly selective and highly sensitive to have practical application value.
It is of the present invention using half river cyanines and flavonols as the Sulfur Dioxide-derivatives scale fluorescence probe of fluorogen, it is special
Sign is: the fluorescence probe is referred to as L-HF1, shown in chemical structural formula such as formula (I):
Above-mentioned fluorescent probe compounds L-HF1 is comprised the following steps:
O-hydroxyacetophenone reacts cyclization through two steps with p -carboxybenzaldehyde and obtains flavonols fluorogen, then passes through amide
The building of key introduces fragrant aldehyde radical, and then is condensed to yield compound L-HF1 with indoles salt.
Experiment confirms: Sulfur Dioxide-derivatives scale fluorescence probe L-HF1 of the present invention can be with half river cyanines fluorescence
Michael addition reaction occurs for the ethylene linkage in group, so that the conjugation of half river cyanines fluorogen is blocked, so that its red fluorescence weakens directly
To disappearance, and the feature green fluorescence of flavonols fluorogen due to fluorescence resonance energy transfer blocking and reappeared, simultaneously
The feature ultraviolet absorption peak of half river cyanines disappears, to achieve the effect that detection, sees Fig. 1.
It is of the present invention to be detected using half river cyanines and flavonols as the Sulfur Dioxide-derivatives scale fluorescence probe of fluorogen
The application of Sulfur Dioxide-derivatives in liquid or cell.
Wherein: it is thin that the liquid or cell are preferably PBS/DMF buffer system, L-02 cell, HepG2 cell or Hela
Born of the same parents.
Specifically, solution of the L-HF1 in PBS/DMF buffer system (pH=7.4, DMF volume fraction 25%) is prepared, point
It is not quantitatively adding the anion (F of micro updating-,Cl-,Br-,I-,HCO3 -,NO3 -,NO2 -,N3 -,AcO-,H2PO4 -,ClO-,ClO3 -,
SO4 2-,HSO4 -,HS-,SCN-,S2O3 2-,HSO3 -And SO3 2-) and various amino acid moleculars (glutamate, histidine,
Lysine, tryptophan, valine, arginine, sarcosine, aspartic acid, cysteine,
Homocysteine, glutathione) aqueous solution.It is tested by fluorescence spectrophotometry common to different aminoacids, human body
The selectivity and responding ability of anion, are as a result shown in Fig. 2, Fig. 3.
Probe L-HF1 is added into HeLa cell living or L-02 cell, then cultivates cell with sodium hydrogensulfite, control adds
Intracellular Fluorescence micro-imaging changes before and after entering sodium hydrogensulfite, as a result sees Fig. 4, Fig. 5.
It is of the present invention to be detected using half river cyanines and flavonols as the Sulfur Dioxide-derivatives scale fluorescence probe of fluorogen
Application in liver cancer cells endogenous sulfur dioxide derivative.
Probe L-HF1 is added into HepG2 cell living, sodium thiosulfate and GSH is added then to stimulate such cell to produce
The bisulfites of Sheng Neisheng, acquisition stimulation front and back intracellular Fluorescence micro-imaging variation, is as a result shown in Fig. 6.
The present invention designs the L-HF1 of synthesis, nucleophilic addition can occur with Sulfur Dioxide-derivatives, to make solution
Fluorescence becomes green from red, and naked eyes are distinguishable, and has good selectivity and specificity, while having high sensitive
Degree realizes the micro highly sensitive detection to Sulfur Dioxide-derivatives, has important application value.
Detailed description of the invention
Fig. 1: to be added not in the PBS/DMF buffer system (pH=7.4, DMF volume fraction 25%, 5 μM) of probe L-HF1
Fluorescence pattern and ultraviolet absorpting spectrum with the sodium hydrogensulfite of 10 equivalents change with time.Wherein: a is fluorescence pattern, and b is
Ultraviolet absorpting spectrum.
Fig. 2: to be added not in the PBS/DMF buffer system (pH=7.4, DMF volume fraction 25%, 5 μM) of probe L-HF1
The fluorescent emission map of congener anion.Wherein: a is fluorescence curve map, and b is corresponding scale fluorescence column map.
Fig. 3: to be added not in the PBS/DMF buffer system (pH=7.4, DMF volume fraction 25%, 5 μM) of probe L-HF1
The fluorescent emission map of congener amino acid.Wherein: wherein: a is fluorescence curve map, and b is corresponding scale fluorescence column
Map.
Fig. 4: being probe L-HF1 in HeLa intracellular Fluorescence micro-imaging figure living.HeLa cell be under the conditions of 37 DEG C, in
It is added in the cell culture fluid of 5 μM of probe L-HF1 and cultivates 1 hour, then use the sodium hydrogensulfite cell culture of various concentration
Liquid is cultivated 0.5 hour.Wherein: a is cell imaging effect picture, and b is corresponding scale fluorescence signal statistics data histograms.
Fig. 5: being probe L-HF1 in L-02 intracellular Fluorescence micro-imaging figure living.L-02 cell be under the conditions of 37 DEG C, in
It is added in the cell culture fluid of 5 μM of probe L-HF1 and cultivates 1 hour, then use the sodium hydrogensulfite cell culture of various concentration
Liquid is cultivated 0.5 hour, or is cultivated 0.5 hour with sodium thiosulfate and GSH.Wherein: a is cell imaging effect picture, and b is corresponding
Scale fluorescence signal statistics data histograms.
Fig. 6: being probe L-HF1 in HepG2 intracellular Fluorescence micro-imaging figure living.HepG2 cell be under the conditions of 37 DEG C,
It cultivates in the cell culture fluid for the probe L-HF1 for being added 5 μM 1 hour, is then cultivated 0.5 hour with sodium thiosulfate and GSH.
HepG2 cell is cultivated 1 hour in the cell culture fluid for the probe L-HF1 for being added 5 μM, is then used under the conditions of 37 DEG C
TNBS (2,4,6-trinitrobenzenesulphonate) is cultivated cell 0.5 hour, then is cultivated with sodium thiosulfate and GSH
Cell 0.5 hour.Wherein: a is cell imaging effect picture, and b is corresponding scale fluorescence signal statistics data histograms.
Specific embodiment
Embodiment 1 is of the present invention using half river cyanines and flavonols as the Sulfur Dioxide-derivatives scale fluorescence probe of fluorogen
Preparation
O-hydroxyacetophenone reacts cyclization through two steps with p -carboxybenzaldehyde and obtains flavonols fluorogen, then passes through amide
The building of key introduces fragrant aldehyde radical, and then is condensed to yield compound L-HF1 with indoles salt.
Above-mentioned reaction process reaction equation is as follows:
By compound 1 (1mmol), compound 2 (1mmol), DMAP (0.1mmol) and EDC (1mmol) are added to 30mL bis-
In chloromethanes, after room temperature reaction 8 hours, with brine organic phase, anhydrous sodium sulfate is dry, filters, and liquid phase is spin-dried for, silicagel column
Column chromatographs (methylene chloride: ethyl acetate=1:1), obtains compound 3, yield 82%, fusing point: 238-239 DEG C.
Infrared analysis (KBr, cm-1):3270,3000,2918,2850,2809,2724,1731,1664,1633,1603,
1568,1483,1421,1288,1227,1159,1006,753。
Nuclear magnetic resonance hydrogen spectruming determining:1H NMR(300MHz,CDCl3): δ 9.83 (s, 1H), 8.36 (d, J=8.7Hz, 2H),
8.27 (dd, J=8.1,1.5Hz, 1H), 7.80 (d, J=8.7Hz, 2H), 7.75-7.72 (m, 1H), 7.64-7.61 (m, 3H),
7.45 (t, J=7.8Hz, 1H), 7.12 (s, 1H), 6.97 (d, J=8.7Hz, 2H), 3.97-3.49 (m, 8H).
Carbon-13 nmr spectra measurement:13C NMR(75MHz,CDCl3):δ190.4,173.5,169.7,155.4,154.5,
143.5,138.9,136.4,134.0,132.7,131.8,128.0,127.9,127.4,125.5,124.7,120.6,
118.3,114.1。
High resolution mass spectrum: m/z calculated for C27H23N2O5 +455.1607,found 455.1602。
Compound 3 (0.5mmol) and 4 (0.6mmol) are dissolved in 20mL dehydrated alcohol, are heated to flowing back.TLC tracking is anti-
It should disappear to compound 3.Rotate away ethyl alcohol, silica gel column chromatography (CH2Cl2: MeOH=30:1 to 15:1) obtain red solid, i.e.,
Fluorescence probe L-HF1 of the invention, yield: 79%.
Infrared analysis (KBr, cm-1):3014,2919,2850,1729,1611,1571,1522,1466,1384,1297,
1237,1190,1115,1004。
Nuclear magnetic resonance hydrogen spectruming determining:1H NMR (400MHz, CDCl3) 8.37 (d, J=8.4Hz, 2H), 8.27 (d, (d, J=
7.6Hz, 1H), 8.24 (d, J=7.2Hz, 2H), 8.09 (d, J=15.6Hz, 1H), 7.75-7.63 (m, 5H), 7.53-7.45
(m, 5H), 7.14 (s, 1H), 6.99 (d, J=6.8Hz, 2H).
Carbon-13 nmr spectra measurement:13C NMR(CDCl3,100MHz)δ180.3,173.5,169.7,155.3,154.7,
154.5,143.6,142.2,141.6,138.9,136.2,134.9,134.0,132.7,129.3,128.5,127.9,
127.5,125.3,124.7,124.1,122.4,120.5,118.4,114.1,113.5,107.2,51.45,46.84,
35.79,27.43。
High resolution mass spectrum: m/z calculated for C39H36N3O4 +610.2706,found 610.2702。
Embodiment 2
With PBS/DMF buffer (pH=7.4, the DMF volume fraction for the probe L-HF1 that micro syringe is prepared to 10mL
It is 25%, 5 μM) in, it is quantitatively adding the various anion (F that ultimate density is 50 μM respectively-,Cl-,Br-,I-,HCO3 -,NO3 -,
NO2 -,N3 -,AcO-,H2PO4 -,ClO-,ClO3 -,SO4 2-,HSO4 -,HS-,SCN-,S2O3 2-,HSO3 -And SO3 2-) and ultimate density be
1mM various amino acid moleculars (glutamate, histidine, lysine, tryptophan, valine, arginine,
Sarcosine, aspartic acid, cysteine, homocysteine, glutathione), effect carries out glimmering after five minutes
The test of light spectrophotometry, display probe have good selectivity to sodium sulfite and sodium hydrogensulfite, be added sodium sulfite with
Sodium hydrogensulfite cross-reference, which is shown, has the variation of apparent fluorescent emission.See Fig. 1,2,3.
Embodiment 3
Intracellular Fluorescence imaging test:
HeLa cell: under the conditions of 37 DEG C, the culture 1 in the cell culture fluid that 5 μM of L-HF1 is added of HeLa cell is small
When；It is cultivated 0.5 hour in the cell culture fluid of sodium hydrogensulfite that various concentration is added again.Fluorescence imaging shows probe L-
HF1 may penetrate into cell, and be gradually increased with the increase green fluorescence of concentration of sodium bisulphite and the intensity ratio of red fluorescence.
See Fig. 4.
L-02 cell: under the conditions of 37 DEG C, the culture 1 in the cell culture fluid that 5 μM of L-HF1 is added of L-02 cell is small
When, then cultivated 0.5 hour in the cell culture fluid of sodium hydrogensulfite that various concentration is added.Fluorescence imaging shows probe L-
HF1 may penetrate into cell, and be gradually increased with the increase green fluorescence of concentration of sodium bisulphite and the intensity ratio of red fluorescence.
5 μM of probe L-HF1 is added into L-02 cell living, then cultivates cell with sodium thiosulfate and GSH, fluorescence imaging, which is shown, to be added
Intracellular Fluorescence micro-imaging changes before and after entering sodium thiosulfate and GSH, sees Fig. 5.
HepG2 cell: under the conditions of 37 DEG C, the culture 1 in the cell culture fluid that 5 μM of L-HF1 is added of HepG2 cell is small
When, cell then is cultivated with sodium thiosulfate and GSH, sodium thiosulfate is added in fluorescence imaging display and the front and back GSH is intracellular glimmering
Light micro-imaging changes.Under the conditions of 37 DEG C, HepG2 cell cultivates 1 in the cell culture fluid that 5 μM of L-HF1 is added
Hour, it is then cultivated cell 0.5 hour with TNBS (2,4,6-trinitrobenzenesulphonate), then use thiosulfuric acid
Sodium and GSH cultivate cell, and fluorescence imaging shows that fluorescent microscopic imaging has no significant change under this situation, sees Fig. 6.
Claims (2)
1. a kind of using half river cyanines and flavonols as the Sulfur Dioxide-derivatives scale fluorescence probe of fluorogen, it is characterised in that: institute
Stating fluorescence probe is formed by connecting with half river cyanines fluorogen by non-conjugated by flavonols fluorogen, is named as L-HF1, chemistry
Shown in structural formula such as formula (I):
2. being detected described in claim 1 using half river cyanines and flavonols as the Sulfur Dioxide-derivatives scale fluorescence probe of fluorogen
The application of Sulfur Dioxide-derivatives in liquid.
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| CN109705115A (en) * | 2017-10-25 | 2019-05-03 | 泰山医学院 | A kind of novel thiazole partly flower cyanines class inferior sulfate radical ratio fluorescent probe and its application |
| CN108129459B (en) * | 2018-01-10 | 2021-02-02 | 济南大学 | Novel fluorescent probe for detecting sulfur dioxide and application thereof |
| CN109575000A (en) * | 2019-01-02 | 2019-04-05 | 济南大学 | A kind of turn-on type sulfur dioxide fluorescence probe and its preparation method and application |
| CN116102485B (en) * | 2022-12-05 | 2024-02-27 | 齐鲁工业大学 | Half cyanine analog ratio type fluorescent probe for detecting sulfur dioxide derivative and preparation method and application thereof |
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| CN105295899A (en) * | 2015-09-21 | 2016-02-03 | 山东大学 | Ratiometric fluorescent probe for detecting hydrogen sulfide and application of ratiometric fluorescent probe |
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| Title |
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| A TP-FRET-based two-photon fluorescent probe for ratiometric visualization of endogenous sulfur dioxide derivatives in mitochondria of living cells and tissues;Xiaoguang Yang，等;《Chem. Comm.》;20160713;第52卷;第10289-10292页 |
| A two-photon fluorescent turn-on probe for imaging of SO2 derivatives in living cells and tissues;Xiaoyan Zhu，等;《Analytica Chimica Acta》;20160725;第937卷;第136-142页 |
| The effects of thermal quenching on the excited-state intramolecular proton transfer reaction in 3-hydroxyflavones;Sule Oncul，等;《Spectrochimica Acta Part A》;20060930;第65卷(第1期);第179–183页 |
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