CN108892681A - A kind of imidazo [1,2-a] pyridines mercury ion Ratiometric fluorescent probe and its application - Google Patents

A kind of imidazo [1,2-a] pyridines mercury ion Ratiometric fluorescent probe and its application Download PDF

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CN108892681A
CN108892681A CN201811059516.8A CN201811059516A CN108892681A CN 108892681 A CN108892681 A CN 108892681A CN 201811059516 A CN201811059516 A CN 201811059516A CN 108892681 A CN108892681 A CN 108892681A
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imidazo
methoxyphenyl
hydrazide derivatives
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pyridine
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段桂运
夏成才
李彦忠
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Taishan Medical University
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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    • 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
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
    • G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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Abstract

The invention discloses a kind of 2-（4- methoxyphenyl）Imidazo [1,2-a] pyridine rhodamine hydrazide derivatives Hg2+Ratiometric fluorescent probe, the probe are the 2- replaced by phenyl isothiocyanate（4- methoxyphenyl）Imidazo [1,2-a] pyridine rhodamine hydrazide derivatives, chemical structural formula such as formula（1）It is shown.Fluorescence probe of the invention is in PBS/EtOH (9/1, v/v, pH=7.50) buffer solution to Hg2+Have preferable fluorescence selectivity, higher sensitivity and it is stronger resist other ion interference abilities, application prospect is extensive.

Description

A kind of imidazo [1,2-a] pyridines mercury ion 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 Hg2+Ratiometric fluorescent probe 2-（4- first Phenyl）The synthesis and its application of imidazo [1,2-a] pyridine rhodamine hydrazide derivatives.
Background technique
Mercury is highly toxic heavy metal, grievous injury human health.Hg simple substance and Hg in environment2+It can be by micro- life Object is converted into methyl mercury, is further absorbed by the body by food chain, to cause to human body brain, kidney and endocrine system huge Big damage.Therefore, mercury ion is identified and detects in life science and environmental monitoring to be of great significance.
Imidazo [1,2-a] pyridine compounds and their is some important drugs using very extensive in field of medicinal chemistry Chief component, such as zolimidine, saripidem, Zolpidem and soraprazan.In addition, such derivative Object also has the bioactivity such as antitumor, antiviral, anti-inflammatory, tranquilizing soporific and antiulcer.But in fluorescence probe field Application be but rarely reported.
Summary of the invention
In view of the deficiencies of the prior art, problems solved by the invention is to provide a kind of Hg of two signals response variation2+Than Rate type fluorescence probe 2-（4- methoxyphenyl）The synthesis and its application of imidazo [1,2-a] pyridine rhodamine hydrazide derivatives.
The technical scheme is that：A kind of 2- replaced by phenyl isothiocyanate（4- methoxyphenyl）Imidazo [1, 2-a] pyridine rhodamine hydrazide derivatives Hg2+Ratiometric fluorescent probe, chemical structural formula such as formula（1）It is shown：
The invention also includes 2-（4- methoxyphenyl）The Hg of imidazo [1,2-a] pyridine rhodamine hydrazide derivatives2+Ratio-type The application of fluorescence probe, formula（1）Compound is in PBS/EtOH (9/1, v/v, pH=7.50) buffer solution to Hg2+Have compared with Good fluorescence selectivity.
The invention also includes the 2- replaced by phenyl isothiocyanate（4- methoxyphenyl）Imidazo [1,2-a] pyridine Luo Dan Bright hydrazide derivatives class Hg2+The synthetic method of Ratiometric fluorescent probe, in n,N-Dimethylformamide solution, by 2-（4- first Phenyl）Imidazo [1,2-a] pyridine rhodamine hydrazide derivatives and phenyl isothiocyanate are according to molar ratio 1:8 feed intake, often Temperature lower reaction 12 hours, obtain the 2- of isothiocyanates substitution（4- methoxyphenyl）Imidazo [1,2-a] pyridine rhodamine acyl Hydrazine derivate.
Prepare 2-（4- methoxyphenyl）The dimethyl sulfoxide solution of imidazo [1,2-a] pyridine rhodamine hydrazide derivatives, It is separately added into quantitative MgCl2, CaCl2, AlCl3, SnCl2·2H2O, PbSO4, CrCl3·6H2O, MnCl2·4H2O, FeCl3·6H2O, FeCl2·4H2O, NaCl, KCl, CuCl2·2H2O, CoCl2·6H2O, NiCl2·6H2O, PdCl2, ZnCl2, HgCl2·2H2O, CdCl2·2½H2O, AgNO3, Na2SO3, NaAc, NaBr, NaH2PO4, NaCl, Na2CO3, NaHCO3, NaF, Na2HPO4, NaHS, NaI, NaNO2, NaNO3, Na2S2O3, Na2SO4Water Solution studies the selectivity to different metal ions by fluorescence spectrum test, surveys its fluorescence emission spectrum Strength Changes hair It is existing：The 2- that phenyl isothiocyanate of the present invention replaces（4- methoxyphenyl）Imidazo [1,2-a] pyridine rhodamine hydrazides spreads out Biology is formula（1）Compound is to Hg2+There is preferable fluorescence selectivity, as shown in Figure 1.It is gradually added into Hg2+To 7 equivalents, chemical combination The fluorescence intensity at 436nm of object 1 is substantially reduced, meanwhile, fluorescence intensity is remarkably reinforced at 590nm, as shown in Figure 2.Therefore, different The 2- that thiocyanic acid phenyl ester replaces（4- methoxyphenyl）Imidazo [1,2-a] pyridine rhodamine hydrazide derivatives are as Hg2+Ratio Fluorescence probe has huge application.
Detailed description of the invention
Fig. 1：Formula（1）Compound（10-6M）PBS/EtOH (9/1, v/v, pH=7.50) buffer solution in be added and 7 work as Fluorescence intensity change ratio bar graphs after the different metal ions of amount, ordinate is the light intensity and 436nm at 590nm in Fig. 1 The ratio between the light intensity at place.
Fig. 2：Formula（1）Compound（10-6M）PBS/EtOH (9/1, v/v, pH=7.50) buffer solution in carry out Hg2 +Fluorescence titration figure.FL Intensity is light intensity in figure, and Wavelength is wavelength, and equiv is multiple.
Fig. 3：Formula（1）Compound（10-6M）Coexisted with other metal ions of 7 equivalents PBS/EtOH (9/1, v/v, PH=7.50) 7 equivalent Hg are added in buffer solution2+Rear fluorescence intensity ratio variation histogram.
Fig. 4 is formula（1）Compound synthesis method reaction equation figure.
Specific embodiment
Embodiment 1：Formula（1）The synthetic schemes of compound is shown below：
Specific synthesis step is as follows：
0.216g is sequentially added in 50 mL round-bottomed flasks（0.30 mmol）2-（4- methoxyphenyl）Imidazo [1,2-a] pyrrole Pyridine rhodamine hydrazide derivatives, 0.32g（2.4 mmol）Phenyl isothiocyanate, 20 mL n,N-Dimethylformamide, under room temperature Reaction 12 hours.TLC is detected after the reaction was completed, and 100 mL methylene chloride are added, and 30 mL are washed three times, dichloromethane layer nothing Aqueous sodium persulfate is dry, and concentration, column chromatographs to obtain 0.13g aubergine solid, yield 67%.
Fusing point test：mp:201-203℃
Nuclear magnetic resonance spectroscopy test1H NMR (400 MHz, DMSO) :δ 11.32 (s, 1H) 8.57 (d, J = 6.8 Hz, 1H), 8.39 (s, 1H), 7.92 (d, J = 8.6 Hz, 2H), 7.82 – 7.75 (m, 1H),7.70 (d, J = 8.5 Hz, 2H) 7.65 (s, 1H), 7.55 – 7.44 (m, 2H),7.43 (d, J = 8.4Hz, 2H), 7.09 (s,1H) 7.02 (d, J = 8.7 Hz, 2H), 7.00 – 6.97 (m, 1H), 6.94 (d, J = 5.9 Hz, 1H), 6.73 (s, 1H), 6.66 (d, J = 9.0 Hz, 1H), 6.43 (d, J = 8.7 Hz, 1H), 6.37 (s, 1H), 6.37 (s, 1H), 6.36 (s, 1H), 4.36 (s, 2H), 3.80 (s, 3H), 3.34 (d, J = 9.3 Hz, 4H), 3.33 – 3.17 (m, 8H), 1.08 (t, J = 6.9 Hz, 6H).
Embodiment 2：
To formula（1）Compound（10-6M）PBS/EtOH (9/1, v/v, pH=7.50) buffer solution in be separately added into 7 and work as The Mg of amount2+, Ca2+, Al3+, Sn2+, Pb2+, Cr3+, Mn2+, Fe3+, Fe2+, Na+, K+, Cu2+, Co2+, Ni2+, Zn2+, Cd2+, Ag+, HCO3 -, Ac-, NO2 -, F-, NO3 -, Br-, I-Afterwards, it is surveyed to send out in 436nm and 590nm fluorescence Penetrate intensity rate variation discovery：Formula（1）Compound is to Hg2+There is preferable fluorescence selectivity, the Hg of 7 equivalents is added2+Afterwards, chemical combination The fluorescence intensity at 436nm of object 1 is substantially reduced, meanwhile, fluorescence intensity is remarkably reinforced at 590nm, I590/I436 =8.6, such as Shown in Fig. 1, Fig. 2.
Embodiment 3：
Respectively at formula（1）Compound（10-6M）With the Mg of 7 equivalents2+, Ca2+, Al3+, Sn2+, Pb2+, Cr3+, Mn2+, Fe3 +, Fe2+, Na+, K+, Cu2+, Co2+, Ni2+, Zn2+, Cd2+, Ag+, HCO3 -, Ac-, NO2 -, F-, NO3 -, Br-, I-In different zwitterion solution, the Hg of 7 equivalents is added2+Afterwards, it is surveyed to become in 436nm and 590nm fluorescent emission intensity ratio Change discovery：Formula（1）Compound has stronger anti-interference ability to other ions, as shown in Figure 3.

Claims (2)

1. a kind of 2-（4- methoxyphenyl）Imidazo [1,2-a] pyridine rhodamine hydrazide derivatives Hg2+Ratiometric fluorescent probe, It is characterized in that：It is the 2- that phenyl isothiocyanate replaces（4- methoxyphenyl）Imidazo [1,2-a] pyridine rhodamine hydrazides Derivative, chemical structural formula such as formula（1）It is shown：
（1）
Formula（1）Compound is in PBS/EtOH (9/1, v/v, pH=7.50) buffer solution to Hg2+There is preferable fluorescence to select Property.
2. 2- described in claim 1（4- methoxyphenyl）Imidazo [1,2-a] pyridine rhodamine hydrazide derivatives class Hg2+Ratio The synthetic method of type fluorescence probe, it is characterised in that：In n,N-Dimethylformamide solution, by 2-（4- methoxyphenyl）Miaow Azoles simultaneously [1,2-a] pyridine rhodamine hydrazide derivativesWith phenyl isothiocyanate according to molar ratio 1:8 feed intake, and react 12 hours under room temperature, obtain the 2- of isothiocyanates substitution（4- methoxyphenyl）Imidazo [1,2-a] pyrrole Pyridine rhodamine hydrazide derivatives.
CN201811059516.8A 2018-09-12 2018-09-12 A kind of imidazo [1,2-a] pyridines mercury ion Ratiometric fluorescent probe and its application Pending CN108892681A (en)

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Citations (6)

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CN108219773A (en) * 2016-12-23 2018-06-29 泰山医学院 Pyridine [1,2-a] and benzimidizole derivatives class Hg2+Ratio fluorescent probe and its application
CN108219772A (en) * 2016-12-23 2018-06-29 泰山医学院 Imidazoles [1,5-a] and pyridine derived species Hg2+Ratio fluorescent probe and its application
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Application publication date: 20181127