CN101302196A - Polyhalogenated acridone compound fluorescent probe and use thereof - Google Patents
Polyhalogenated acridone compound fluorescent probe and use thereof Download PDFInfo
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- CN101302196A CN101302196A CNA2008100586313A CN200810058631A CN101302196A CN 101302196 A CN101302196 A CN 101302196A CN A2008100586313 A CNA2008100586313 A CN A2008100586313A CN 200810058631 A CN200810058631 A CN 200810058631A CN 101302196 A CN101302196 A CN 101302196A
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Abstract
The invention discloses an application of polyhalogenated acridone compound in a buffer solution as a pH fluorescent probe for high selective identification of hydrogen ions. The compound has water solubility with an excitation wavelength of between 260 and 280 nm and an emission wavelength more than or equal to 400 nm, which contributes to a wide application range. The compound has characteristics of high quantum yield (pH value is equal to 1, Phi is more than or equal to 0.7) and fluorescent stability, etc. With the change of pH value, the specific value of fluorescence intensity and the pH change are in linear correlation in a certain range of acidity and alkalescence. As a result, the measurement of pH change in acid range and alkaline range by a ratio method is realized. The compound produces high sensitive and high selective fluorescent responses to the pH value at two extremities ( strong acid and strong alkali ), and is a fluorescent probe suitable for measuring extreme pH values.
Description
Technical field
The present invention relates to polyhaloacridones compound as the application to the identification of hydrogen ion highly selective in buffered soln of pH fluorescent probe.
Background technology
The carrying out of chemical reaction or finish, many important physiological processs of cell and organoid etc. all with pH value closely related (Fuh, M.R.S.; Burgess, L.W.; Hirschfeld, T.; Et al.Analyst, 1987,112,1159; Khramtsov, V.V.; Grigor ' Ev, I.A.; Foster, M.A.; Lurie, D.J.; Et al.Cell Mol.Biol.2000,46,1361), the accurate measurement of pH value is very important to chemicobiology research.And fluorescence spectrometry pH is not only highly sensitive, and can detect the DYNAMIC DISTRIBUTION and the regional change of internal pH in real time, has caused people's attention (Srivastava, A.Krishnamoorthy, G.Anal.Biochem.1997,249,140).
Dihydroketoacridine compounds structure contains big π key conjugated structure, and the molecule two ends are connected with electron-withdrawing group (C=0) and electron donating group (N-R simultaneously
2), thereby intramolecular transfer transport takes place easily, make molecule have stronger fluorescent emission function.The dihydroketoacridine compounds has high light stability (Bahr.N.; Tierney, E., Reymond., J.L.Tetrahedron Lett, 1997,38:1489-1492; Rothman, J.H., Still, W.C.Bioorg Med ChemLett, 1999,9:509-512.), chemical stability, the fluorescent emission wavelength is moderate, fluorescence quantum yield is high, superperformance such as big stokes (Stokes) displacement is arranged, and begins to be used to the synthetic of multiple fluorescent molecular probe in recent years.But the fluorescence compounds of report comprises that the dihydroketoacridine compounds uses the narrower pH scope that only is confined to as fluorescent probe at present, development is suitable for measuring the fluorescent probe of extreme pH (as pH＜5 or pH＞9), will promote biological study (Su, the M. of relevant special living things system; Liu, Y.; Ma, H.; Et aJ.Chem.Commun.2001,960; Lin, H.; Herman, P.; Kang, J.S.; Et al.Anal.Biochem.2001,294,118).
Up to the present, the synthetic of how halogenated acridone derivatives only has my seminar to apply for Chinese invention patent (application number: 200810058228.0) on the phenyl ring.This compounds excitation wavelength is at 260～280nm, emission wavelength 〉=400nm, thus and have water-soluble its scope of application that enlarges.This compounds has characteristics such as quantum yield extra-high-speed (pH=1, Φ 〉=0.7), fluorescence are stable, and along with the variation of pH, this compounds has the different forms of dissociating, and wherein has only cationic form and neutral molecule that stronger fluorescent emission is arranged.Be linear dependence at the ratio of acid and alkaline its fluorescence intensity of certain pH scope and the variation of pH, in view of the above, can realize that the pH that ratio method is measured in acidity or the alkaline range changes.Thereby it is significant as the applied research of pH fluorescent probe to many halos dihydroketoacridine photoluminescent property.The purpose of this patent is with the application of many halos dihydroketoacridine compound simple in structure as PH fluorescent probe aspect.This compounds can produce the fluorescence response of highly sensitive, highly selective to the pH (strong acid and highly basic) of two extreme scopes.This fluorescent probe that is suitable for measuring extreme pH has great importance to the biological study that promotes relevant special living things system.
Application content
A series of polyhaloacridones compounds, structure is applied to the pH fluorescent probe suc as formula (I).
In the formula (I), X
1, X
2, Y=fluorine, chlorine; R=alkyl, aryl; R '=alkyl, aryl;
In formula (I), R and R ' all are preferably pyridyl, indyl, imidazolyl, naphthyl, benzimidazolyl-, benzothiazolyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenmethyl, styroyl or the hydrocinnamyl of methyl, ethyl, propyl group, sec.-propyl, normal-butyl, isobutyl-, the tertiary butyl, methylamino, dimethylin, diethylin, ethylamino-, Propylamino, isopropylamine base, n-butylamine-based, isobutyl amine, TERTIARY BUTYL AMINE base, methylthio group, ethylmercapto group, rosickyite base, butylthio, replacement.
This patent is applied to the pH fluorescent probe with polyhaloacridones compound (I)
Its representation compound is as follows:
(I-A) work as X
1Be Cl, X
2During for Cl, Y is Cl, and R is H, and R ' is H;
(I-B) work as X
1Be Cl, X
2During for Cl, Y is Cl, and R is H, and R ' is Cl;
(I-C) work as X
1Be Cl, X
2During for Cl, Y is Cl, and R is H, and R ' is CH
3
(I-D) work as X
1Be F, X
2During for F, Y is Cl, and R is H, and R ' is H;
(I-E) work as X
1Be F, X
2During for F, Y is Cl, and R is H, and R ' is Cl;
(I-F) work as X
1Be F, X
2During for F, Y is Cl, and R is H, and R ' is CH
3
(I-G) work as X
1Be F, X
2During for F, Y is F, and R is H, and R ' is H;
(I-H) work as X
1Be F, X
2During for F, Y is F, and R is H, and R ' is Cl;
(I-I) work as X
1Be F, X
2During for F, Y is F, and R is H, and R ' is CH
3
(I-J) work as X
1Be Cl, X
2During for Cl, Y is Cl, and R is Me, and R ' is H;
(I-K) work as X
1Be Cl, X
2During for Cl, Y is Cl, and R is Et, and R ' is H;
(I-L) work as X
1Be Cl, X
2During for Cl, Y is Cl, and R is Me, and R ' is Cl;
(I-M) work as X
1Be Cl, X
2During for Cl, Y is Cl, and R is Et, and R ' is Cl;
(I-N) work as X
1Be F, X
2During for F, Y is Cl, and R is Me, and R ' is H;
(I-O) work as X
1Be F, X
2During for F, Y is Cl, and R is Et, and R ' is H;
(I-P) work as X
1Be F, X
2During for F, Y is Cl, and R is Me, and R ' is Cl;
(I-Q) work as X
1Be F, X
2During for F, Y is Cl, and R is Et, and R ' is Cl;
(I-R) work as X
1Be F, X
2During for F, Y is F, and R is Me, and R ' is H;
(I-S) work as X
1Be F, X
2During for F, Y is F, and R is n-Bu, and R ' is Cl.
This patent is applied to PH fluorescent probe aspect to many halos of formula simple in structure (I) dihydroketoacridine compound photoluminescent property.
Description of drawings
Fig. 1 is the fluorescence emission spectrogram of Compound I G in different solvents;
Fig. 2 is fluorescence emission spectrogram and the pH of Compound I A---maximum fluorescence emission peak changing trend diagram;
Fig. 3 is fluorescence emission spectrogram and the pH of Compound I D---maximum fluorescence emission peak changing trend diagram;
Fig. 4 is fluorescence emission spectrogram and the pH of Compound I G---maximum fluorescence emission peak changing trend diagram;
Fig. 5 is fluorescence emission spectrogram and the pH of Compound I E---maximum fluorescence emission peak changing trend diagram;
Fig. 6 is fluorescence emission spectrogram and the pH of Compound I H---maximum fluorescence emission peak changing trend diagram.
Fig. 7 is the mensuration of the quantum yield of Compound I D.
Embodiment
The fluorescence spectrum of Compound I G in different solvents: the fluorescence spectrum of IG in different solvents DMF, DCM, DMSO, ethanol and acetonitrile, found that, along with the increase of solvent polarity, fluorescence spectrum generation red shift shows that the emission attitude of IG has intramolecular charge transfer characteristic (seeing accompanying drawing 1).
Compound I A is at EtOH/H
2In 4.6＜pH＜7.0, fluorescence intensity presents quick downtrending to the pH value to its influence: Compound I A in O=1/1 (v/v) system.And after pH＞7.0, fluorescence intensity increases with alkalescence and does not significantly change, and this shows suit good indicative function between 4.6＜pH＜7.0 of this compound, and ten minutes is suitable for pH fluorescence sense probe (seeing accompanying drawing 2); In 0.7＜pH＜5.6 scopes, increase along with the pH value of solution value, fluorescence intensity reduces gradually, but the peak position does not change with the variation of pH value of solution value, show that luminous species do not change in the solution (still being two kinds of forms: neutral molecule and acid salt), but the fluorescence intensity at 456nm place is weakening gradually, and the fluorescence intensity at 481nm place is strengthening, and illustrates that Compound I A exists following ionization equilibrium:
Embodiment 3
Compound I D is at EtOH/H
2In 2.9＜PH＜8.0, fluorescence intensity presents quick downtrending to the pH value to its influence: Compound I D in O=1/1 (v/v) system.And after pH＞8.0, fluorescence intensity increases with alkalescence and does not significantly change, and this shows suit good indicative function between 2.9＜pH＜8.0 of this compound, is suitable for pH fluorescence sense probe (seeing accompanying drawing 3); In 0.3＜pH＜5.8 scopes, increase along with the pH value of solution value, fluorescence intensity reduces gradually, but the peak position does not change with the variation of pH value of solution value, show that luminous species do not change in the solution (still being two kinds of forms: neutral molecule and acid salt), but the fluorescence intensity at 441nm place is weakening fast, and the fluorescence intensity at 463nm place weakens and slowly promptly occurred by high right low bimodal low right high conversion the in a left side Compound I D and IDH being described left
+Exist ionization equilibrium.When pH=5.8, left peak disappears substantially, illustrates that compound exists with single type body ID.When the pH value increases to pH＞6.8, a new fluorescence emission peak appears at the 493nm place, and at this moment, still be that a left side is high right low bimodal, along with the increase of pH value, occurred ID and ID being described left by the high right low bimodal low right side height conversion in a left side
-Exist the ionization weighing apparatus.When pH＞11.8, the completely dissolve of left peak illustrates that this moment is with ID
-Exist.Ionization equilibrium is expressed as follows.When 10.5＜pH＜14.1, fluorescence intensity presents quick downtrending, and this shows this compound good indicative function between 10.5＜pH＜14.1 (seeing accompanying drawing 3) equally, is suitable for pH fluorescence sense probe under the highly basic condition.
During pH=5.8, mainly there are pH＞11.8 o'clock, mainly with ID with ID
-Exist
Compound I E is at EtOH/H
2In 0.9＜PH＜8.2, fluorescence intensity presents quick downtrending to the pH value to its influence: Compound I E in O=1/1 (v/v) system.And after pH＞8.2, fluorescence intensity increases with alkalescence and does not significantly change, and this shows suit good indicative function between 0.9＜pH＜8.2 of this compound, is suitable for pH fluorescence sense probe (seeing accompanying drawing 4); In 0.9＜pH＜4.4 scopes, increase along with the pH value of solution value, fluorescence intensity is the imposing manner that descends, but the peak position does not change with the variation of pH value of solution value, show that luminous species do not change in the solution (still being two kinds of forms: neutral molecule and acid salt), but the fluorescence intensity at 449nm place is weakening fast, and the fluorescence intensity at 471nm place weakens and slowly promptly occurred by high right low bimodal low right high conversion the in a left side Compound I E and IEH being described left
+Exist ionization equilibrium.When pH=4.4, left peak disappears substantially, illustrates that compound exists with single type body IE.When the pH value increases to pH＞5.9, one new fluorescence emission peak appears at the 497nm place, and at this moment, two peak heights are suitable, and along with the increase of pH value, the low right side, bimodal appearance left side height illustrates IE and IE
-Exist the ionization weighing apparatus.When pH＞11.9, the completely dissolve of left peak illustrates that this moment is with IE
-Exist.Ionization equilibrium is expressed as follows.When 11.9＜pH＜15.0, fluorescence intensity presents quick downtrending, and this shows this compound good indicative function between 11.9＜pH＜15.0 (seeing accompanying drawing 4) equally, is suitable for pH fluorescence sense probe under the highly basic condition.
4.4 there are pH＞11.9 o'clock in＜pH＜4.7 o'clock with IE, with IE
-Exist
0.9＜pH＜4.4 o'clock, IE and IEH
+There are 5.9＜pH＜11.9 o'clock, IE and IE simultaneously
-Exist simultaneously
Compound I G is at EtOH/H
2In 5.2＜pH＜7.3, fluorescence intensity presents quick downtrending to the pH value to its influence: Compound I G in O=1/1 (v/v) system.And when 7.3＜pH＜11.7, fluorescence intensity increases with alkalescence and does not significantly change, and this shows suit good indicative function between 5.2＜pH＜7.3 of this compound, is suitable for pH fluorescence sense probe (seeing accompanying drawing 5); In 0.2＜pH＜5.2 scopes, increase along with the pH value of solution value, fluorescence intensity is the imposing manner that descends, but the peak position does not change with the variation of pH value of solution value, show that luminous species do not change in the solution (still being two kinds of forms: neutral molecule and acid salt), but the fluorescence intensity at 441nm place is weakening fast, and the fluorescence intensity at 463nm place weakens slowly, and Compound I G and IGH are described
+Exist ionization equilibrium.When pH=5.7, left peak disappears substantially, illustrates that compound exists with single type body IG.When the pH value increases to pH＞6.6, one new fluorescence emission peak appears at the 487nm place, and at this moment, two peak heights are suitable, and along with the increase of pH value, the low right side, bimodal appearance left side height illustrates IG and IG
-Exist the ionization weighing apparatus.When pH＞13.0, left peak disappears substantially, illustrates that this moment is with IG
-Exist.Ionization equilibrium is expressed as follows.When 11.8＜pH＜14.6, fluorescence intensity presents quick downtrending, and this shows this compound good indicative function between 11.7＜pH＜14.6 (seeing accompanying drawing 5) equally, is suitable for pH fluorescence sense probe under the highly basic condition.
5.7 there are pH＞13.0 o'clock in＜pH＜6.6 o'clock with IG, with IG
-Exist
0.2＜pH＜5.2 o'clock, IG and IGH
+There are 6.6＜pH＜13.0 o'clock, IG and IG simultaneously
-Exist simultaneously
Compound I H is at EtOH/H
2In 2.8＜pH＜4.4, fluorescence intensity presents quick downtrending to the pH value to its influence: Compound I H in O=1/1 (v/v) system.And when 4.4＜pH＜11.3, fluorescence intensity increases with alkalescence and does not significantly change, and this shows suit good indicative function between 2.8＜pH＜4.4 of this compound, is suitable for pH fluorescence sense probe (seeing accompanying drawing 6); In 2.8＜pH＜4.4 scopes, increase along with the pH value of solution value, fluorescence intensity is the imposing manner that descends, but the peak position does not change with the variation of pH value of solution value, show that luminous species do not change in the solution (still being two kinds of forms: neutral molecule and acid salt), but the fluorescence intensity at 448nm place is weakening fast, and the fluorescence intensity at 471nm place weakens slowly, and Compound I H and IHH are described
+Exist ionization equilibrium.When pH=4.4, left peak disappears substantially, illustrates that compound exists with single type body IH.When the pH value increases to pH＞5.5, one new fluorescence emission peak appears at the 492nm place, and at this moment, two peak heights are suitable, and along with the increase of pH value, the low right side, bimodal appearance left side height illustrates IH and IH
-Exist the ionization weighing apparatus.When pH＞13.6, left peak disappears substantially, illustrates that this moment is with IH
-Exist.Ionization equilibrium is expressed as follows.When 11.7＜pH＜14.6, fluorescence intensity presents quick downtrending, and this shows this compound good indicative function between 11.7＜pH＜14.6 (seeing accompanying drawing 6) equally, is suitable for pH fluorescence sense probe under the highly basic condition.
4.4 there are pH＞13.6 o'clock in＜pH＜5.5 o'clock with IH, with IH
-Exist
0.8＜pH＜4.4 o'clock, IH and IHH
+There are 5.5＜pH＜13.6 o'clock, IH and IH simultaneously
-Exist simultaneously
Embodiment 7
The mensuration of Compound I A quantum yield: the 0.1mol/L H that selects 1 μ g/mL Quinine Sulphate Di HC for use
2SO
4Solution is as standard substance (Φ
Fstd=0.55), adopt the fluorescence quantum yield simplified measurement method that kind Yun Xiang etc. proposes [Ci Yunxiang, Jia Xin. analytical chemistry, 1986,14:616-617.].Solution to be measured is also selected 0.1mol/L H for use
2S
O4As solvent, utilize formula (1) to calculate acridone derivatives at 0.1mol/L H
2SO
4Fluorescence quantum yield (Φ in the solution
f):
Φ in the following formula
FstdΦ for the standard substance Quinine Sulphate Di HC
f, n
StdAnd n
x(standard substance, solution to be measured are all used 0.1mol/L H to be respectively the refractive index of Quinine Sulphate Di HC solution and solution to be measured
2SO
4As solvent, so n
Std=n
x); F
StdAnd F
xBe respectively the fluorescence peak height of standardized solution and solution to be measured, experiment records the quantum yield Φ of Compound I A
FIA=0.70.
The mensuration of Compound I D quantum yield: replacing Compound I A with Compound I D is Φ by the quantum yield that the method for embodiment 6 records Compound I D
FID=0.98 (seeing accompanying drawing 7).
Embodiment 9
The mensuration of Compound I E quantum yield: replacing Compound I A with Compound I E is Φ by the quantum yield that the method for embodiment 6 records Compound I D
FIE=0.81.
The mensuration of Compound I G quantum yield: replacing Compound I A with Compound I G is Φ by the quantum yield that the method for embodiment 6 records Compound I D
FIG=0.70.
Embodiment 11
The mensuration of Compound I H quantum yield: replacing Compound I A with Compound I H is Φ by the quantum yield that the method for embodiment 6 records Compound I D
FIH=0.92.
Claims (5)
1, a series of polyhaloacridones compounds, structure is applied to the pH fluorescent probe suc as formula (I).
In the formula (I), X
1, X
2, Y=fluorine, chlorine; R=alkyl, aryl; R '=alkyl, aryl.
2, the polyhaloacridones compound that is applied to the pH fluorescent probe is characterized in that general structure is:
Its representation compound is as follows:
(I-A) work as X
1Be Cl, X
2During for Cl, Y is Cl, and R is H, and R ' is H;
(I-B) work as X
1Be Cl, X
2During for Cl, Y is Cl, and R is H, and R ' is Cl;
(I-C) work as X
1Be Cl, X
2During for Cl, Y is Cl, and R is H, and R ' is CH
3
(I-D) work as X
1Be F, X
2During for F, Y is Cl, and R is H, and R ' is H;
(I-E) work as X
1Be F, X
2During for F, Y is Cl, and R is H, and R ' is Cl;
(I-F) work as X
1Be F, X
2During for F, Y is Cl, and R is H, and R ' is CH
3
(I-G) work as X
1Be F, X
2During for F, Y is F, and R is H, and R ' is H;
(I-H) work as X
1Be F, X
2During for F, Y is F, and R is H, and R ' is Cl;
(I-I) work as X
1Be F, X
2During for F, Y is F, and R is H, and R ' is CH
3
(I-J) work as X
1Be Cl, X
2During for Cl, Y is Cl, and R is Me, and R ' is H;
(I-K) work as X
1Be Cl, X
2During for Cl, Y is Cl, and R is Et, and R ' is H;
(I-L) work as X
1Be Cl, X
2During for Cl, Y is Cl, and R is Me, and R ' is Cl;
(I-M) work as X
1Be Cl, X
2During for Cl, Y is Cl, and R is Et, and R ' is Cl;
(I-N) work as X
1Be F, X
2During for F, Y is Cl, and R is Me, and R ' is H;
(I-O) work as X
1Be F, X
2During for F, Y is Cl, and R is Et, and R ' is H;
(I-P) work as X
1Be F, X
2During for F, Y is Cl, and R is Me, and R ' is Cl;
(I-Q) work as X
1Be F, X
2During for F, Y is Cl, and R is Et, and R ' is Cl;
(I-R) work as X
1Be F, X
2During for F, Y is F, and R is Me, and R ' is H;
(I-S) work as X
1Be F, X
2During for F, Y is F, and R is n-Bu, and R ' is Cl.
3, the described formula of claim 1 (I) compound is applied to the pH fluorescent probe, it is characterized in that polyhaloacridones compound with formula (I) structure carries out hydrogen ion selective identification and promptly carries out hydrogen ion concentration and survey in different buffered soln.
4, the described application method of root a tree name claim 3 is characterized in that (I) formula compound is carried out fluoroscopic examination between 0.1＜pH＜15, and carries out the relevant pH-fluorescence intensity figure that obtains according to the change of fluorescence intensity with the relation of hydrogen ion concentration.
5, the described formula of root a tree name claim 1 (I) compound carries out the mensuration of quantum yield.
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ID=40112314
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104838254A (en) * | 2012-11-30 | 2015-08-12 | 锡克拜控股有限公司 | Marking of material, marked material and process of authentication or dilution determination |
| CN107311927A (en) * | 2017-08-04 | 2017-11-03 | 福建医科大学 | A kind of amino acridones of 10 methyl of two-photon fluorescence probe 2 and its preparation method and application |
| CN108218863A (en) * | 2018-03-05 | 2018-06-29 | 泰山医学院 | A kind of pyrazolo [1,5-a] picolinic acid class pH fluorescence probes and its application |
| CN108503635A (en) * | 2018-05-02 | 2018-09-07 | 泰山医学院 | A kind of substituted imidazole simultaneously [1,2-a] pyridines pH fluorescence probes and its application |
| CN108640915A (en) * | 2018-05-02 | 2018-10-12 | 泰山医学院 | A kind of substituted imidazole simultaneously [1,5-a] pyridines pH fluorescence probes and its application |
-
2008
- 2008-07-03 CN CNA2008100586313A patent/CN101302196A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104838254A (en) * | 2012-11-30 | 2015-08-12 | 锡克拜控股有限公司 | Marking of material, marked material and process of authentication or dilution determination |
| CN107311927A (en) * | 2017-08-04 | 2017-11-03 | 福建医科大学 | A kind of amino acridones of 10 methyl of two-photon fluorescence probe 2 and its preparation method and application |
| CN108218863A (en) * | 2018-03-05 | 2018-06-29 | 泰山医学院 | A kind of pyrazolo [1,5-a] picolinic acid class pH fluorescence probes and its application |
| CN108503635A (en) * | 2018-05-02 | 2018-09-07 | 泰山医学院 | A kind of substituted imidazole simultaneously [1,2-a] pyridines pH fluorescence probes and its application |
| CN108640915A (en) * | 2018-05-02 | 2018-10-12 | 泰山医学院 | A kind of substituted imidazole simultaneously [1,5-a] pyridines pH fluorescence probes and its application |
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