CN107365326A - It is a kind of to be used to detect fluorescence probe of fluorine ion and preparation method thereof in living cells - Google Patents

It is a kind of to be used to detect fluorescence probe of fluorine ion and preparation method thereof in living cells Download PDF

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CN107365326A
CN107365326A CN201710606941.3A CN201710606941A CN107365326A CN 107365326 A CN107365326 A CN 107365326A CN 201710606941 A CN201710606941 A CN 201710606941A CN 107365326 A CN107365326 A CN 107365326A
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fluorine ion
fluorescence
fluorescence probe
living cells
probe
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CN107365326B (en
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毛伍祥
徐小为
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Hubei University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

It is used to detect fluorescence probe of fluorine ion and preparation method thereof in living cells the invention discloses a kind of.The fluorescence probe has the structure shown in Formulas I; the probe itself is almost without any fluorescence; but under fluorine ion induction; Si O keys are broken, and take off TBDPS blocking groups, generate phenolic hydroxyl group; discharge HPQ; excited state intramolecular proton transfer effect thus occurs, produces the phenomenon that fluorescence greatly strengthens, so as to realize that " turn on " detect the strategy of fluorine ion to fluorescence.When fluorine ion is in low concentration 20uM, under ultra violet lamp, the phenomenon of fluorescence probe enhancing can be observed visually；The probe has good bio-compatibility, energy permeation cell film, with reference to laser confocal microscope, it may be observed that it produces response to the horizontal fluorine ion of micromole's level in living cells.In addition, synthetic method of the present invention is simple, post processing is easy, without being purified through column chromatography, the final product with regard to higher yields can be obtained.

Description

It is a kind of to be used to detect fluorescence probe of fluorine ion and preparation method thereof in living cells
Technical field
It is used to detect fluorescence probe of fluorine ion and preparation method thereof in living cells the present invention relates to a kind of, belongs to fluorescence spy Pin field.
Background technology
All played an important role in the various physiology courses of anion in vivo.Especially fluorine ion, it is even more Indispensable a kind of micro ion in human life activity.Effect of the fluorine ion to human body is a double-edged sword：When appropriate It is a kind of required micro ion, but it is excessive when it has toxic action again.Such as：Appropriate fluoride is dredged available for sclerotin The treatment of loose disease and the health care of tooth；However, excessive fluorine ion is then easily caused, den tal fluorosis, fluorosis of bone, IQ reduce, enzyme loses It is living, or even cause kidney, stomach and intestine and immune system equivalent damage.In addition, fluoride can also cause collagen and mucopolysaccharide to be metabolized Change etc..Although the chemical constitution for fluorine ion is it has become clear that many on fluorine ion in organism The problem of dynamic equilibrium and physiological action, does not understand still.At present, in organism the trace detection of fluorine ion and correlation physiology, New method is developed in pathological study all an urgent demands, to monitor the dynamic change of fluorine ion in organism.Meanwhile to intracellular fluorine Ion is monitored in real time, is also beneficial to study accumulation, metabolism and the conversion of fluorine ion in vivo.Fluorescence probe in recent years Related research work is just being carried out like a raging fire, and it provides a kind of quick, easy and intuitively analysis method to people.Such as If " visualization " of fluorine ion can be realized in living cells, there will be very extensive application prospect.Therefore, exploitation is a kind of high Selectivity, in high-sensitivity detection living cells the fluorescence probe of fluorine ion become there is an urgent need to.
In the fluorescence probe for several detection fluorine ions being reported, a part is using in pyrroles or urea group N-H and fluorine ion form the mechanism of hydrogen bond action to realize the identification to fluorine ion, but in this case, formed The power of hydrogen bond and its influence that solvent effect is highly prone to the selectively acting of fluorine ion；For another part probe, The strong affinity between fluoro- boron, fluoro- silicon is based primarily upon to realize the identification to fluorine ion.Such as：Tae-Hyun Kim etc. are reported A series of probe of coumarin derivatives alternatively property identification fluorine ion；They, which design, has synthesized a series of semi-conductive polymerics Thing, using the amplification of semi-conducting polymer with reach improve detection sensitivity purpose.It is well known that polymer Cell membrane penetration is poor, significantly limit the fluorescence imaging of fluorine ion in living cells.Untill the present, organism can be suitably used for The Small-molecule probe of interior fluorine ion detection and imaging is also rarely reported always.
(the 3H)-quinazolinones (HPQ) of 2- (2 '-hydroxy phenyl) -4 are a kind of probes with a variety of outstanding photoluminescent properties. Such as：With larger stoke displacements, the Accurate Analysis available for determinand；It is prone to excited state intramolecular proton transfer Effect, fluorescence " turn-on " strategy is realized, background signal is low, can reduce and repeatedly be washed in spectrofluorimetry and cell imaging The step of washing probe, it enormously simplify detecting step；With the effect for focusing on induced luminescence, more conducively determinand in cell imaging Precise positioning；Simultaneously also there is two-photon fluorescence property, presented in cell imaging and living imaging penetration power it is extremely strong, damage Hinder small advantage.In consideration of it, how to utilize the advantage of HPQ fluorescent parent rings, the fluorescence imaging of fluorine ion in living cells is realized, into The problem of thinking deeply for us.
The content of the invention
The primary and foremost purpose of the present invention is to provide a kind of fluorescence probe for being used to detect fluorine ion in living cells.
The secondary objective of the present invention is the preparation method for providing above-mentioned fluorescence probe.
The secondary objective of the present invention is to provide application of the above-mentioned fluorescence probe in fluorine ion detection field.
Technical scheme provided by the invention is specific as follows：
A kind of fluorescence probe for being used to detect fluorine ion in living cells, has the structure shown in Formulas I：
(abbreviation HPQF).
A kind of method for preparing above-mentioned fluorescence probe, comprises the following steps：By compound a and 2- aminobenzamides together It is dissolved in methanol, is stirred 10 minutes prior to 0 DEG C, reheat backflow 30 minutes；Then para toluene sulfonamide is added, continues backflow 1 Hour；After question response liquid is cooled to room temperature, DDQ is added, is stirred overnight, filtered, gained filter residue is above-mentioned glimmering Light probe；Described compound a is
Preferably, the mole dosage of compound a, 2- aminobenzamides, para toluene sulfonamide and DDQ For 1:1:0.1:1.
Application of the above-mentioned fluorescence probe in fluorine ion detection field.
The purposes of fluorine ion in above-mentioned fluorescence probe detection living cells.
The present invention principle be：The present invention, with reference to the structure of HPQ parent rings, synthesizes target by the method for organic synthesis Compound HPQF；Now, HPQF is broken Si-O keys, takes off TBDPS almost without any fluorescence, but under fluorine ion induction Blocking group, phenolic hydroxyl group is generated, discharge HPQ, therefore excited state intramolecular proton transfer effect occurs, produced fluorescence and greatly increase Strong phenomenon, so as to realize the strategy of fluorescence " turn-on " detection fluorine ion.
The present invention has advantages below and beneficial effect：
1. the present invention has synthesized the fluorescence probe HPQF for detecting fluorine ion in living cells first, synthetic method is simple, Post processing is easy, without being purified through column chromatography, the final product with regard to higher yields can be obtained.
2. present invention firstly discovers that the mechanism that HPQF responds to fluorine ion, is broken by Si-O keys, TBDPS guarantors are sloughed Shield, generate the compound HPQ of Fluorescence Increasing.
3. the present invention realizes the Visual retrieval of fluorine ion.When fluorine ion is in low concentration 20uM (0.38mg/L), Under ultra violet lamp, the phenomenon of Fluorescence Increasing can be observed visually (see Fig. 2).According to National Industrial wastewater discharge standard, fluorine Ion concentration should be less than 10mg/L；For drinking water, fluorinion concentration requirement is in below 1mg/L.Therefore, the detection of the compound Lower limit can fully meet industrial wastewater and the exceeded testing conditions of fluoride ion in drinking water.
4. the present invention realizes the fluorescence imaging (see Fig. 3) of fluorine ion in living cells, with reference to HPQ itself two-photon Matter, by for cell or in vivo the fluorescence monitoring of fluorine ion provides new thinking.
Brief description of the drawings
Fig. 1 is the principle of luminosity schematic diagram that compound HPQF detects fluorine ion.
Fig. 2 is the fluorescent spectrum curve that compound HPQF responds to fluorine ion；Wherein ,-F-Represent fluoride-free solution ,+F- Represent solution of the fluorinion concentration as 20uM.
Fig. 3 is the cell imaging figure that compound HPQF detects fluorine ion in living cells；Wherein, Fig. 3 (A) represents blank control Group, Fig. 3 (B) represent experimental group.
Embodiment
Technical scheme is further described with instantiation below.
Embodiment 1：Compound HPQF synthesis
Compound a (550.6mg) and 2- aminobenzamides (177.3mg) are together dissolved in 40mL methanol, prior to 0 DEG C Lower stirring 10 minutes, then flow back 30 minutes；Then para toluene sulfonamide (20mg) is added, continues backflow 1 hour；Question response liquid is cold But to after room temperature, DDQ (270.8mg) being added, is stirred overnight, filtered, gained filter residue is compound HPQF, Yield 70%.
1H NMR(300MHz,CDCl3)δ(ppm):10.96 (s, 1H), 8.53 (d, J=6.99Hz, 1H), 8.29 (d, J= 7.86Hz, 1H), 7.77~7.70 (m, 6H), 7.48~7.35 (m, 8H), 7.20~7.13 (m, 3H), 7.07 (d, J= 8.31Hz, 1H), 6.81 (d, J=8.37Hz, 2H), 5.19 (s, 2H), 1.11 (s, 9H)13C NMR(75MHz,CDCl3)δ (ppm):161.69,157.05,156.05,150.88,149.43,135.60,134.45,133.08,132.73,131.58, 130.03,128.92,127.90,127.65,126.48,126.47,122.14,121.36,120.54,120.34,113.91, 71.55,26.57.ESI-HRMSC37H34N2O3Si[M+Na]+Theoretical values：605.22309, actual numerical value：605.22552 Both are consistent substantially.
Embodiment 2：Compound HPQF vitro detection fluorine ions
Compound HPQF is dissolved in DMSO, solution (20-200uM) 1uL of various concentrations is configured to, then adds by four The fluoride solution (0-2000uM) for the various concentrations that butyl ammonium fluoride (TABF) is formulated, after waiting 0-10 minutes, set Excitation wavelength 405nm, collect the fluorescence signal intensity at wavelength 470-530nm.When fluorinion concentration is in 20uM, can just observe To obvious fluorescence " turn-on " effect.
Embodiment 3：Fluorine ion in compound HPQF detection living cells
First by HepG2 passage culture 2-10 hours, if experimental group adds fluoride solution and co-cultures 1-6 hours, if Blank control group and the contrast solution co-cultivation 1-6 hours for being not added with fluorine ion；Then washed repeatedly with a large amount of PBS solutions HepG2 cells are multiple, fully wash away extracellular free fluorine ion；Add compound HPQF (20-200uM) and be incubated 0.5- altogether 3 hours, pass through the fluorescence intensity of two groups of cells of confocal laser scanning microscope.Experimental result is as shown in figure 3, and blank control Group is compared, and experimental group visual field fluorescence intensity is remarkably reinforced, and is shown that compound HPQF has good cell membrane penetration, can be applied In the dynamic monitoring of fluorinion concentration in living cells.

Claims (5)

1. a kind of fluorescence probe for being used to detect fluorine ion in living cells, it is characterised in that there is the structure shown in Formulas I：
A kind of 2. method for preparing the fluorescence probe described in claim 1, it is characterised in that comprise the following steps：By compound a Together it is dissolved in 2- aminobenzamides in methanol, is stirred 10 minutes prior to 0 DEG C, reheat backflow 30 minutes；Then addition pair Toluenesulfonamide, continue backflow 1 hour；After question response liquid is cooled to room temperature, DDQ is added, is stirred overnight, takes out Filter, gained filter residue is the fluorescence probe described in claim 1；Described compound a is
3. according to the method for claim 2, it is characterised in that：Compound a, 2- aminobenzamides, para toluene sulfonamide Mole dosage with DDQ is 1:1:0.1:1.
4. fluorescence probe described in claim 1 is in the application of fluorine ion detection field.
5. the purposes of fluorine ion in the fluorescence probe detection living cells described in claim 1.
CN201710606941.3A 2017-07-24 2017-07-24 It is a kind of for detecting the fluorescence probe and preparation method thereof of fluorine ion in living cells Expired - Fee Related CN107365326B (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108623624A (en) * 2018-06-12 2018-10-09 兰州大学 A method of differentiating toothpaste with fluoride with probe S-F bore holes
CN110373181A (en) * 2019-07-09 2019-10-25 济南大学 A kind of fluorescence probe detecting fluorine ion

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103130827A (en) * 2013-03-19 2013-06-05 武汉大学 Compound for detecting fluoride ion and preparation method and application thereof
CN104449677A (en) * 2014-12-29 2015-03-25 大连理工常熟研究院有限公司 Specific fluorescent probe for recognizing fluorine ions and application of specific fluorescent probe
CN105131935A (en) * 2015-08-27 2015-12-09 晋江尚京富本环保科技有限公司 Rapid high-selectivity fluorine ion colorimetric probe and preparation method therefor

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
CN103130827A (en) * 2013-03-19 2013-06-05 武汉大学 Compound for detecting fluoride ion and preparation method and application thereof
CN104449677A (en) * 2014-12-29 2015-03-25 大连理工常熟研究院有限公司 Specific fluorescent probe for recognizing fluorine ions and application of specific fluorescent probe
CN105131935A (en) * 2015-08-27 2015-12-09 晋江尚京富本环保科技有限公司 Rapid high-selectivity fluorine ion colorimetric probe and preparation method therefor

Non-Patent Citations (3)

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Title
JIUN-AN GU等: "Design and synthesis of ultrasensitive off–on fluoride detecting fluorescence probe via autoinductive signal amplification", 《ANALYST》 *
SABIR H. MASHRAQUI等: "A new indole incorporated chemosensor exhibiting selective colorimetric and fluorescence ratiometric signaling of fluoride", 《TETRAHEDRON LETTERS》 *
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108623624A (en) * 2018-06-12 2018-10-09 兰州大学 A method of differentiating toothpaste with fluoride with probe S-F bore holes
CN110373181A (en) * 2019-07-09 2019-10-25 济南大学 A kind of fluorescence probe detecting fluorine ion
CN110373181B (en) * 2019-07-09 2021-05-04 济南大学 Fluorescent probe for detecting fluorine ions

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