CN109694706A - A kind of half flower cyanines class SO of cyanofuran32-Ratiometric fluorescent probe and its application - Google Patents

A kind of half flower cyanines class SO of cyanofuran32-Ratiometric fluorescent probe and its application Download PDF

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CN109694706A
CN109694706A CN201710984482.2A CN201710984482A CN109694706A CN 109694706 A CN109694706 A CN 109694706A CN 201710984482 A CN201710984482 A CN 201710984482A CN 109694706 A CN109694706 A CN 109694706A
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formula
ratio
fluorescent probe
benzimidazole
cyanofuran
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葛燕青
刘爱坤
吉瑞雪
曹晓群
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Taishan Medical University
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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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
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    • 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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Abstract

The invention discloses the half flower cyanines class Ratio-type inferior sulfate radical fluorescence probe of cyanofuran that a kind of pyrido [1,2-a] benzimidazole replaces, chemical structural formula is as the formula (1).Fluorescence probe of the invention is shown in n,N-Dimethylformamide/water (volume ratio 3:7) solution to SO3 2‑There are the abilities such as higher sensitivity and specific recognition, sensitive rapidly can distinguish sulfite ion from a variety of anion, have broad application prospects.

Description

A kind of half flower cyanines class SO of cyanofuran32-Ratiometric fluorescent probe and its application
Technical field
The present invention relates to small organic molecule fluorescence probe field more particularly to a kind of pyrido [1,2-a] benzimidazole piperazines Piperazine cyanofuran class SO3 2-Ratio fluorescent probe and its application.
Background technique
SO2It is a kind of main atmosphere pollution, the main composition person of acid rain, the close phase of health with human and animal It closes.SO2Mainly exist in the form of inferior sulfate radical and bisulfite in vivo.Sulphite or a kind of made extensively Food preservative, and can also be generated by the amino acid metabolism of sulfur-bearing in human body.Although having, researches show that sulfurous acid Salt can stimulate the excitability of nervous system, but when its concentration causes respiratory disease compared with Gao Shihui.In recent years, sub- in organism Important indicator of the content of sulfate as body whether normal operation, oneself is more and more paid close attention to by people.Therefore, fastly The concentration of sulphite has a very important significance in speed, easy quantitative detection organism.
Current analysis method mainly includes atomic absorption spectrum, electrochemical method, inductive coupling, Plasma-Atomic hair The methods of spectroscopic methodology and mass spectrum are penetrated, in numerous detection technique means, fluorescence probe detection method is highly selective with its, highly sensitive Degree, simple operation and other advantages, are widely applied to the fields such as bioanalysis, environmental monitoring, life science and clinical analysis.
Fluorescent probe technique is since selectivity is good, the advantages that high sensitivity, test process is efficient and convenient, in food and medicine analysis Great application prospect is shown, a new research hotspot is become.Due to fluorescence probe to determinand have it is fabulous Specificity, can be to avoid the interference of other lewis' acids, while may be implemented by sepectrophotofluorometer to determinand Quantitative detection.Therefore, novel fluorescence dyestuff is developed, the fluorescence probe for sulfite ion detection is one very significant Work.
Summary of the invention
In view of the deficiencies of the prior art, the present invention provides a kind of two signals response variation, selective good SO3 2- Ratio fluorescent probe and its application.
The technical scheme is that the half flower cyanines class of cyanofuran that a kind of pyrido [1,2-a] benzimidazole replaces SO3 2-Ratio fluorescent probe, chemical structural formula are as the formula (1):
(1)
The invention also includes SO3 2-The application of ratio fluorescent probe, formula (1) compound is in neutral aqueous solution to SO3 2-There is uniqueness Fluorescence selectivity.
The invention also includes SO3 2-The synthetic method of ratio fluorescent probe, in dichloromethane solution, by 4- phenyl-pyridin And [1,2-a] benzimidazole -3- formic acid, 2-(4-(4-(piperazinyl) styryl) -5,5- dimethyl furan base) malononitrile, DMAP, EDC feed intake according to molar ratio 1:1.1:1.5:1.5, and normal-temperature reaction 24 hours, obtain pyrido [1,2-a] benzimidazole Half flower cyanines class SO of substituted cyanofuran3 2-Ratio fluorescent probe.
Prepare the SO3 2-The n,N-Dimethylformamide of ratio fluorescent probe/water (volume ratio 3:7) solution, is separately added into Quantitative Na2SO3, NaAcO, NaBr, NaH2PO4, NaCl, Na2CO3, NaHCO3, NaF, Na2HPO4, NaHS, NaI, NaNO2, NaNO3, Na2S2O3, Na2SO4, FeCl3, CaCl2, CuCl2, KCl, NaCl, ZnCl2, GSH, Hcy, the aqueous solution of Cys, by glimmering Light spectrum test studies the probe to the selectivity of different ions and amino acid, and fluorescence emission spectrum Strength Changes show: Half flower cyanines class SO of the cyanofuran that pyrido [1,2-a] benzimidazole replaces3 2-Ratio fluorescent probe, i.e. formula (1) compound pair SO3 2-There is unique fluorescence selectivity, as shown in Figure 1, being gradually added into SO3 2-To 10 equivalents, the fluorescence at 640nm of compound 1 Intensity is substantially reduced, meanwhile, fluorescence intensity is remarkably reinforced at 465nm.Therefore, pyridine [1,2-a] and benzimidazole replace Half cyanine compound of cyanofuran, that is, formula (1) compound is as SO3 2-Ratio fluorescent probe has huge application.
The present invention provides the half flower cyanines class SO of cyanofuran that a kind of pyrido [1,2-a] benzimidazole replaces3 2-Ratio is glimmering Light probe, i.e. formula (1) compound, experiments have shown that formula of the present invention (1) compound can be with SO3 2-In aqueous solution in terms of chemistry Amount is reacted than 1:10, during the reaction, due to sulfurous ion damaged 2-(4-(4-(piperazinyl) styryl) -5,5- bis- Methylfuran base) conjugated double bond in malononitrile in phenyl ring and cyanofuran between phenyl ring and cyanofuran, so that double bond is disconnected, Making donor 4- phenyl-pyridin, simultaneously [1,2-a] benzimidazole cannot be conjugated with receptor cyanofuran, and compound 1 is caused to exist Fluorescence intensity is substantially reduced at 640nm, meanwhile, fluorescence intensity is remarkably reinforced at 465nm.Thus susceptible of proof formula of the present invention (1) compound is in aqueous solution to SO3 2-There are unique fluorescence selectivity, higher sensitivity and stronger resists other ions dry Ability is disturbed, there is huge application prospect.
Detailed description of the invention
Fig. 1: formula (1) compound (5 × 10-6M be added in neutral aqueous solution) different anions of equivalent, cation, The variation histogram of fluorescence intensity ratio after amino acid, the light intensity and the light intensity at 640nm that ordinate is the place 465nm in Fig. 1 The ratio between.
Fig. 2: formula (1) compound (5 × 10-6M SO is carried out in neutral aqueous solution)3 2-Fluorescence titration figure.FL in figure Intensity is fluorescence intensity, and Wavelength is wavelength, and equiv is multiple.
Fig. 3: formula (1) compound (5 × 10-6) and the SO of equivalent M3 2-Its that equivalent is added in neutral aqueous solution coexists The variation histogram of fluorescence intensity ratio after its metal ion, the light intensity and the light at 640nm that ordinate is the place 465nm in Fig. 3 It is the ratio between strong.
Fig. 4: formula (1) compound synthesis method reaction equation figure.
Fig. 5: formula (1) compound (5 × 10-6M different anions, the cation, amino of equivalent are added in neutral aqueous solution) The variation histogram of fluorescence intensity ratio after acid, the ratio between ordinate is the place 465nm in Fig. 5 light intensity and light intensity at 640nm.
Specific embodiment
Embodiment 1: the synthetic schemes of formula (1) compound is shown below:
Specific synthesis step is as follows:
0.29g(1.0 mmol is sequentially added in 25mL round-bottomed flask) by 4- phenyl-pyridin simultaneously [1,2-a] benzimidazole -3- Formic acid, 0.41g(1.1 mmol) 2-(4-(4-(piperazinyl) styryl) -5,5- dimethyl furan base) malononitrile, 0.18g (1.5mmol) DMAP, 0.29g(1.5mmol) EDC, 20ml methylene chloride, normal-temperature reaction 24 hours, TLC detection reaction was completed Afterwards, about 1g silica gel is added, is concentrated and dried on vacuum rotary evaporator, dry method loading, column chromatography for separation, is concentrated, obtains 0.60g aubergine Solid, yield 94.3%.
Nuclear magnetic resonance hydrogen spectruming determining:1H NMR(400 MHz, CDCl3): δ 8.56 (d, 1H), 7.98 (m, 2H), 7.87 (d,2H), 7.54 (m,6H),7.44 (m,2H), 6.95 (d,1H), 6.79 (d,1H), 6.74 (d,2H),5.30 (s, 1H), 3.93 (d, 1H), 3.54 (m, 2H), 3.25 (t, 1H), 3.18 (t, 2H), 2.98 (t, 1H), 1.75 (s,8H)。
Embodiment 2:
To formula (1) compound (5 × 10-5M the SO of 10 equivalents is separately added into neutral solution)3 2-, AcO-, Br-, H2PO4 -, Cl-, CO3 2-, HCO3 -, F-, HPO42-, HS-, I-, NO2 -, NO3 -, S2O3 2-, SO4 2-, Fe3+, Ca2+, Cu2+, K+, Na+, Zn2+, GSH, After Hcy and Cys, survey it in 465nm and 640nm fluorescent emission intensity ratio and change discovery: formula (1) compound is to SO3 2-Have The SO of 10 equivalents is added in unique fluorescence selectivity3 2-Afterwards, the fluorescence intensity at 640nm of compound 1 is substantially reduced, meanwhile, Fluorescence intensity is remarkably reinforced at 465nm, I465/I640 =7.19, as shown in Figure 1.
Embodiment 3:
In formula (1) compound (5 × 10-5M the SO of 10 equivalents is separately added into neutral aqueous solution)3 2-, AcO-, Br-, H2PO4 -, Cl-, CO3 2-, HCO3 -, F-, HPO42-, HS-, I-, NO2 -, NO3 -, S2O3 2-, SO4 2-, Fe3+, Ca2+, Cu2+, K+, Na+, Zn2 +, after GSH, Hcy and Cys, survey it and change in 640nm and 465nm fluorescence emission curves and find: formula (1) compound is to other Ion has stronger anti-interference ability, as shown in Figure 3.

Claims (2)

1. the present invention relates to the half flower cyanines class Ratio-type inferior sulfate radicals of cyanofuran that a kind of pyrido [1,2-a] benzimidazole replaces Fluorescence probe, chemical structural formula are as the formula (1):
(1)
Formula (1) compound is in neutral aqueous solution to SO3 2-There is unique fluorescence selectivity.
2. SO described in claim 13 2-The synthetic method of ratio fluorescent probe, it is characterised in that:, will in dichloromethane solution 4- phenyl-pyridin simultaneously [1,2-a] benzimidazole -3- formic acid, 2-(4-(4-(piperazinyl) styryl) -5,5- dimethyl furan Base) malononitrile, DMAP, EDC feed intake according to molar ratio 1:1.1:1.5:1.5, and normal-temperature reaction 24 hours, obtain pyrido [1,2- A] the half flower cyanines class SO of cyanofuran that replaces of benzimidazole3 2-Ratio fluorescent probe.
CN201710984482.2A 2017-10-20 2017-10-20 A kind of half flower cyanines class SO of cyanofuran32-Ratiometric fluorescent probe and its application Pending CN109694706A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111057009A (en) * 2019-12-02 2020-04-24 西北大学 Cyanovinylene derivative fluorescent dye and preparation method and application thereof
CN111362929A (en) * 2020-04-20 2020-07-03 山东大学 Ratiometric fluorescent probe for detecting sulfur dioxide derivative and application thereof
CN114295569A (en) * 2022-01-21 2022-04-08 中国药科大学 Application of hemicyanine molecular optical probe in detecting bisulfite

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105906623A (en) * 2016-05-24 2016-08-31 泰山医学院 Pyridino[1, 2-a]benzimidazole carboxylic acid pH fluorescence probe and application thereof
CN106543166A (en) * 2016-11-07 2017-03-29 湖南师范大学 A kind of colorimetric and Ratio-type detection SO2And its synthesis and application of derivatives fluorescent probe

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105906623A (en) * 2016-05-24 2016-08-31 泰山医学院 Pyridino[1, 2-a]benzimidazole carboxylic acid pH fluorescence probe and application thereof
CN106543166A (en) * 2016-11-07 2017-03-29 湖南师范大学 A kind of colorimetric and Ratio-type detection SO2And its synthesis and application of derivatives fluorescent probe

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111057009A (en) * 2019-12-02 2020-04-24 西北大学 Cyanovinylene derivative fluorescent dye and preparation method and application thereof
CN111057009B (en) * 2019-12-02 2022-03-25 西北大学 Cyanovinylene derivative fluorescent dye and preparation method and application thereof
CN111362929A (en) * 2020-04-20 2020-07-03 山东大学 Ratiometric fluorescent probe for detecting sulfur dioxide derivative and application thereof
CN111362929B (en) * 2020-04-20 2021-08-03 山东大学 Ratiometric fluorescent probe for detecting sulfur dioxide derivative and application thereof
CN114295569A (en) * 2022-01-21 2022-04-08 中国药科大学 Application of hemicyanine molecular optical probe in detecting bisulfite

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