CN110669503A - Preparation and application of carbon monoxide near-infrared fluorescent probe - Google Patents

Preparation and application of carbon monoxide near-infrared fluorescent probe Download PDF

Info

Publication number
CN110669503A
CN110669503A CN201911084617.5A CN201911084617A CN110669503A CN 110669503 A CN110669503 A CN 110669503A CN 201911084617 A CN201911084617 A CN 201911084617A CN 110669503 A CN110669503 A CN 110669503A
Authority
CN
China
Prior art keywords
fluorescent probe
carbon monoxide
probe
fluorescent
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201911084617.5A
Other languages
Chinese (zh)
Other versions
CN110669503B (en
Inventor
李春艳
王文新
刘扬
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Xiangtan University
Original Assignee
Xiangtan University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Xiangtan University filed Critical Xiangtan University
Priority to CN201911084617.5A priority Critical patent/CN110669503B/en
Publication of CN110669503A publication Critical patent/CN110669503A/en
Application granted granted Critical
Publication of CN110669503B publication Critical patent/CN110669503B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • 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"
    • 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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • 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
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/20—Air quality improvement or preservation, e.g. vehicle emission control or emission reduction by using catalytic converters

Abstract

The invention relates to preparation and application of a carbon monoxide (CO) near-infrared fluorescent probe, wherein the structural formula of the probe is as follows:
Figure DDA0002263886940000011
the invention provides a preparation method for synthesizing the fluorescent probe by taking benzopyran nitrile-xanthene dye, triethylamine, allyl chloroformate and the like as raw materials; the fluorescent probe is a carbon monoxide fluorescent probe with near infrared emission and large Stokes displacement; firstly, the fluorescent probe shows high sensitivity to CO, and the fluorescence intensity is enhanced by 21 times; secondly, the fluorescent probe shows high selectivity to CO and is free from other active oxygen and active oxygenInterference with sex nitrogen, various ions, and biological thiols and amino acids; moreover, the fluorescent probe has rapid action with CO, and the response time is within 10 min; in addition, the fluorescent probe is applied to the detection of the content of carbon monoxide in living cells.

Description

Preparation and application of carbon monoxide near-infrared fluorescent probe
Technical Field
The invention belongs to the technical field of fluorescent probes, and particularly relates to preparation and application of a carbon monoxide fluorescent probe based on benzopyran nitrile-xanthene dye.
Background
Carbon monoxide (CO) is a colorless, odorless gas that may be used in vivoTo compete with oxygen for binding to hemoglobin, thereby hindering normal transport of oxygen (l.k.weaver, n.engl.j.med.2009,360, 1217-1225). Carbon monoxide has long been recognized as a toxic and harmful substance if excessive ingestion of exogenous carbon monoxide can lead to carbon monoxide poisoning in living organisms. However, there is a great deal of scientific evidence that carbon monoxide is like Nitric Oxide (NO) and hydrogen sulfide (H)2S), as well, play an important role in the body as gas transport agents and in various physiological and pathological processes (f.watel, r.farry, s.lancel, r.neviere, d.mathieu, fill.acad.natl.med.2006, 190, 1961-1975; L.Y.Wu, R.Wang, Pharmacol.Rev.2005,57, 585-. Furthermore, abnormal endogenous CO concentrations are closely associated with the development of various diseases, such as: alzheimer's disease, hypertension, inflammation and heart failure, etc. (D.R.Premkumar, M.A.Smith, P.L.Richey, R.B.petersen, R.Castellani, R.K.Kutty, J.Neurochem.1995,65, 1399-Buck 1402; R.A.Schroeder, C.A.Ewing, J.V.Sitzmann, P.C.Kuo, dig.Dis.Sci.2000,45, 2405-Buck 2410; I.T.Lee, S.F.Luo, C.W.Lee, S.W.Wang, C.C.Lin, C.C.Chang, am.J.Pathol.2009,175, 519-532; V.S.Raju, N.aig, C.S.Liang, J.Modil.31.1589, 1999). Therefore, it is very important to develop a convenient and reliable method for real-time detection of CO in biological systems.
Conventional methods for detecting CO include electrochemical methods, gas chromatography, and colorimetric methods, which are not suitable for real-time, dynamic CO observation in living cells and living bodies. The fluorescence method is of great interest because of its many advantages, such as easy operation, good selectivity, high sensitivity, good membrane permeability, etc. (h.kobayashi, m.ogawa, r.alford, p.l.choyke, y.urano, chem.rev.2010,110, 2620-2640; x.li, x.gao, w.shi, h.ma, chem.rev.2014,114, 590-659.). To date, several fluorescent probes for detecting CO have been developed for monitoring changes in CO in cells or in vivo in real time (W.Feng, D.Liu, Q.ZHai, G.Feng, Sens.activators B.2017,240, 625-630; W.Feng, D.Liu, S.Feng, G.Feng, anal.chem.2016,88, 10648-10653; S.Feng, D.Liu, W.Feng, Ang.chem.2017, 89, 3754-3760; W.Feng, J.hong, G.Feng, Sens.activators B.2017,251, 389-395.). However, these carbon monoxide fluorescent probes still have some disadvantages: the emission wavelength of the fluorescent probe is short, and the Stokes shift is small. This makes the probe susceptible to interference from self-background fluorescence, which is not conducive to deep tissue and in vivo imaging detection. Therefore, it is crucial to design a near infrared fluorescent probe having a large stokes shift.
The benzopyranone-xanthene has the advantages of large Stokes shift, high fluorescence quantum yield and the like as a novel fluorescent dye. In particular, the dye has near infrared emission, so that the dye has a deeper tissue penetration depth, is not easily interfered by biological autofluorescence, and is more beneficial to biological imaging. It has been found that fluorescent probes using benzopyran nitrile-xanthene dyes have been successfully used to detect some targets, such as: cys, HNO, etc. (Y.Qi, Y.Huang, B.Li, F.Zeng, S.Z.Wu, anal.chem.2018,90, 1014-. However, CO has not been detected so far based on this dye as a fluorescent probe. Therefore, it is very necessary to design and synthesize a fluorescent probe based on benzopyran nitrile-xanthene dye to detect CO.
Disclosure of Invention
In light of the proposed requirements, the present inventors have conducted intensive studies to provide a carbon monoxide near infrared fluorescent probe based on a benzopyran nitrile-xanthene dye after a great deal of creative work.
The invention adopts the technical scheme that a carbon monoxide near-infrared fluorescent probe has the following structural formula:
Figure BDA0002263886920000021
a method for preparing a carbon monoxide near-infrared fluorescent probe. The method comprises the following steps:
in N2Under protection, 0.5 equivalent of DCX-OH, 2.0 to 3.0 equivalents of allyl chloroformate and 2.0 to 3.0 equivalents of triethylamine are dissolved in 8 to 12mL of THF in a 25mL round-bottom flask, then the reaction is stirred at room temperature overnight, and after the reaction is finished, water is added to dilute the solutionUsing CH together2Cl2Extraction, washing the organic layer with brine, and then with anhydrous Na2SO4Drying, filtering and concentrating the crude product with CH2Cl2And purifying by silica gel column chromatography as eluent to obtain a dark green solid product DCX-CO, namely the fluorescent probe.
The invention has the beneficial effects that the carbon monoxide near infrared fluorescent probe based on the benzopyran nitrile-xanthene dye has good spectral response performance. First, the fluorescence spectrum properties of the probe were investigated. The probe itself or added Pd2+Thereafter, there was no significant near-infrared emission peak at 762 nm; when Pd is added to the probe2+And CO, a distinct near-infrared emission peak at 762nm was observed. And the near infrared fluorescence intensity of the probe is continuously enhanced along with the increase of the CO concentration. Next, the ultraviolet absorption spectrum of the probe was investigated. The probe has an absorption band at 549nm, and Pd is added2+After that, the absorption peak was not significantly changed. Adding Pd simultaneously2+And after CO, the ultraviolet absorption peak at 549nm gradually decreases, and a new strong absorption peak appears at 598 nm. Then, the selectivity of the probe was investigated to examine the probe and various metal ions (Na)+,K+,Mg2+,Ca2+) And biological thiols (Cys, Hcy, GSH), amino acids (Lys, Glu, Ala), active oxygen (ONOO)-,H2O2,·OH,ClO-,O2 -) Active nitrogen (NO, NO)2 -,NO3 -) And the fluorescence response of the detector (CO). As a result, it was found that only CO caused the change in the fluorescence spectrum, and that the other analytes had no significant effect on the fluorescence spectrum of the probe. Finally, the effect of pH on the CO measurement by the fluorescent probe was investigated, and the CO measurement by the fluorescent probe was not affected when the pH was between 7.0 and 9.0. In addition, the fluorescent probe has a relatively quick response, and the response time is within 10 minutes.
An application of a carbon monoxide near-infrared fluorescent probe. After the cells are cultured in normal environment, the fluorescent probe and Pd are added2+After that, almost no fluorescence generation was observed. Then, exogenous CO cell imaging is carried out, and CORM-3 (carbon monoxide releasing agent) incubation, then adding fluorescent probe and Pd2+Confocal fluorescence imaging was then performed and significant fluorescence generation was observed. Then, the cells were treated with heme (which stimulates CO production) for cellular imaging of endogenous CO, and the addition of fluorescent probes and PdCl was found2After that, the near infrared fluorescence enhancement was clearly observed. These results indicate that the fluorescent probe can detect the intracellular CO production, which provides a reliable means for monitoring CO changes in associated pathological processes in vivo.
Drawings
FIG. 1 shows a synthetic route of a fluorescent probe.
FIG. 2 is a fluorescence spectrum of a fluorescent probe after the probe is reacted with CO at different concentrations.
The abscissa is wavelength and the ordinate is fluorescence intensity. Fluorescent probe and Pd2+The concentrations of (A) and (B) were all 10. mu.M, and the concentrations of CO were respectively: 0,1,5,10,20,30,40,50,60,70,80,90, 100. mu.M. The emission wavelength was 762nm, corresponding to an excitation wavelength of 598 nm.
FIG. 3 is a graph showing the linear response of fluorescent probe to different CO concentrations.
FIG. 4 shows a fluorescent probe and Pd2+And ultraviolet-visible absorption spectrogram after CO action.
The abscissa is wavelength and the ordinate is absorbance. Fluorescent probe and Pd2+The concentrations of (A) and (B) were 10. mu.M, and the CO concentration was 100. mu.M.
FIG. 5 is a graph showing selectivity of fluorescent probes.
Fluorescent probe and Pd2+Concentrations of (A) were all 10. mu.M, CO concentrations were 100. mu.M, and other analyte concentrations were all 200. mu.M.
FIG. 6 is a graph showing the effect of pH on fluorescent probes.
FIG. 7 is a graph showing the relationship between the fluorescence intensity of the fluorescent probe and the change with time after the CO reaction.
FIG. 8 is a graph showing cytotoxicity test. The abscissa is the concentration of the fluorescent probe and the ordinate is the survival rate of the cells.
FIG. 9 is an image of a cell image of the interaction of fluorescent probe with CO. (a) Cells were stained with probe for 0.5 h. (b) Simultaneous application of probe and Pd to cells2+And dyeing for 0.5 h. (c) After cells were incubated with CORM-3, probes and Pd2+And dyeing for 0.5 h. (d) Cells were treated with Heme for 4h, then with both probe and Pd2+And dyeing for 0.5 h.
Detailed Description
The present invention will be described in detail below with reference to the accompanying drawings and specific embodiments, but is not limited thereto.
Example 1:
synthesis of fluorescent probes
The synthetic route is shown in figure 1. In N2DCX-OH (209mg,0.5mmol), allyl chloroformate (240mg,2.0mmol), triethylamine (200mg,2.0mmol) were dissolved in 10mL of THF in a 25mL round-bottomed flask with protection, and the reaction was stirred at room temperature overnight, after completion, diluted with water and CH2Cl2Extraction, washing the organic layer with brine, and then with anhydrous Na2SO4Drying, filtering and concentrating, purifying the crude product by silica gel column Chromatography (CH)2Cl2) And obtaining a dark solid product DCX-CO (150mg, the yield is 60%), namely the fluorescent probe.1H NMR(400MHz,CDCl3)δ8.91(d,J＝9.3Hz,1H),8.07(d,J＝15.6Hz,1H),7.73(t,J＝7.8Hz,1H),7.61(d,J＝7.6Hz,1H),7.43(t,J＝7.6Hz,1H),7.10(d,J＝8.3Hz,1H),7.02(s,1H),6.88(dd,J＝8.3,2.2Hz,1H),6.77(s,1H),6.49(s,1H),6.14(d,J＝15.5Hz,1H),6.08-6.00(m,1H),5.48(d,J＝17.1Hz,1H),5.39(d,J＝10.5Hz,1H),4.79(d,J＝5.9Hz,2H),2.62-2.55(m,2H),2.49(t,J＝5.9Hz,2H),1.85(dt,J＝11.8,6.1Hz,2H).13C NMR(100MHz,CDCl3)δ159.1,153.2,153.1,152.6,151.8,151.5,134.1,133.5,130.9,126.7,125.7,123.3,122.3,120.1,119.9,118.6,117.6,116.2,114.7,111.6,108.5,108.2,105.9,69.5,60.1,29.8,24.5,20.6.MS(TOF):502.2.
Example 2:
fluorescent probe and CO solution preparation
Preparation of probe solution: weighing a certain amount of probe, dissolving in dimethyl sulfoxide to prepare 1 × 10-4M probe solution. Simultaneously weighing a certain amount of PdCl2Dissolving in secondary distilled water to obtain 1 × 10 solution-4Stock solutions of M. CO 2Preparing a solution: dissolving a certain amount of CORM-3 in redistilled water, transferring to a 100mL volumetric flask, adding water to the scale mark to obtain a concentration of 1.0 × 10-3mol·L-1CORM-3 of (1). Mixing 1.0X 10-3mol·L-1The solution of CORM-3 was gradually diluted to give 1.0X 10-3-1.0×10-5mol·L-1An aqueous solution of CORM-3. 1.0mL of a stock solution of the probe, 1.0mL of PdCl2Adding the solution and 1.0mL CORM-3 aqueous solution into 10mL volumetric flask, and diluting to constant volume with buffer solution to obtain a concentration of 1.0 × 10- 5mol·L-1Fluorescent probe and PdCl of2，1.0×10-4-1.0×10-6mol·L-1CO (ii) is mixed with the solution to be tested.
Example 3:
determination of fluorescence Spectroscopy of the interaction of fluorescent probes with CO
FIG. 2 shows fluorescence spectra of the interaction of fluorescent probe with CO, fluorescent probe and Pd2+The concentration of (A) is 10 μ M, and the concentration of CO is 0,1,5,10,20,30,40,50,60,70,80,90 and 100 μ M in sequence. The excitation wavelength used in the experiment is 598nm, and the emission wavelength range is 650-900 nm. The slit width was 10.0nm/10.0nm, and the fluorescence measuring instrument used was a Hitachi F4600 fluorescence spectrophotometer. As can be seen from FIG. 2, before the addition of CO, the fluorescent probe added Pd due to the quenching effect of allyl formate2+Thereafter, there was no significant near infrared emission peak at near infrared (762 nm); adding Pd simultaneously2+And CO, a distinct near-infrared emission peak at 762 nm. This is because of Pd2+First reduced to Pd by CO0Subsequently, the Tsuji-Trost reaction is mediated, resulting in cleavage of the allyl formate, releasing the benzopyranonitrile-xanthene fluorophore, which produces near infrared fluorescence. And the near infrared fluorescence intensity of the probe molecules is continuously enhanced along with the increase of the CO concentration. FIG. 3 is a graph of the linear response of the probe to different CO concentrations. The fluorescence intensity is in linear relation with the concentration of CO, and the linear range is 1.0 multiplied by 10-6～1.0×10-4M, the detection limit is 0.33. mu.M. This indicates that the probe can detect CO with high sensitivity.
Example 4:
determination of ultraviolet-visible absorption spectrum of action of fluorescent probe and CO
FIG. 4 is an ultraviolet-visible absorption spectrum of the fluorescent probe after the reaction with CO, wherein the concentration of the fluorescent probe is 10 μ M and the addition amount of CO is 100 μ M. The instrument for measuring the ultraviolet visible absorption spectrum is an Agilent Cary60 ultraviolet visible spectrophotometer. As can be seen from FIG. 4, the probe itself has an absorption band at 549 nm; adding Pd2+After that, the absorption peak was not significantly changed; adding Pd simultaneously2+And CO, the absorption peak at 549nm gradually decreased, and a new strong absorption peak near 598nm appeared.
Example 5:
selectivity of fluorescent probes for CO determination
FIG. 5 is a graph of selectivity of fluorescent probes for CO determination. Examination of fluorescent Probe and Pd at a concentration of 10. mu.M2+Adding CO (100 μ M) and its various metal ions (Na) into the solution+,K+,Mg2+,Ca2+) And biological thiols (Cys, Hcy, GSH), amino acids (Lys, Glu, Ala), active oxygen (ONOO)-,H2O2,·OH,ClO-,O2 -) Active nitrogen (NO, NO)2 -,NO3 -) The fluorescent response of (c). As can be seen in FIG. 5, only CO caused a significant enhancement in the fluorescence spectrum, and the other analytes had no significant effect on the fluorescence spectrum of the probe. These results indicate that the fluorescent probe is better selective for CO.
Example 6:
influence of solution pH value on fluorescence property of fluorescent probe for determining CO
The effect of pH on the fluorescence spectrum of CO measured with the fluorescent probe was examined, and the results are shown in FIG. 6. The pH range of our study is 2.0-10.0, fluorescent probe and Pd2+The concentrations of (A) and (B) were all 10. mu.M, and the concentration of CO was 100. mu.M. As can be seen from the figure, the fluorescence intensity of the fluorescent probe is basically unchanged along with the change of pH, which shows that the pH has no great influence on the probe. However, after the addition of CO, the fluorescence intensity ratio is remarkably enhanced in the pH range of 7.0-9.0. In summary, the pH value of 7.0 to 9.0 does not affect the fluorescent probe pair CThe determination of O is a relatively proper pH value range, which is very beneficial to the probe for determining CO in actual samples.
Example 7:
determination of response time of fluorescent probe to CO action
We investigated the response time of fluorescent probes to CO, the results of which are shown in FIG. 7. As can be seen from the figure, the response time of the probe to CO is 10min, which can meet the requirement of real-time monitoring in actual samples. From FIG. 7, it can also be seen that the fluorescence intensity does not change any more after reaching the maximum value and in the following time, which indicates that the fluorescence probe has better light stability.
Example 8:
application of fluorescent probe in living cell
First, we performed cytotoxicity assays as shown in fig. 8. When 0-30. mu.M CO probe was added, the survival rate of both cells (HepG2 cells, HCT116cells) was above 90%. This can indicate that the fluorescent probe is less toxic and can be used to detect CO in living cells. Then, we investigated the application of fluorescent probe in living cells, and selected liver cancer cell HepG2 and colon cancer cell HCT116 for confocal microscopy imaging, and the results are shown in fig. 9. Only the fluorescent probe was added to the cells and little fluorescence was observed (fig. 9 a); adding fluorescent probe and Pd simultaneously into cells2+There was still no significant change in fluorescence (FIG. 9b), indicating a lower CO content in the cells. Subsequently, a carbon monoxide releasing agent (CORM-3) was added to the cells, followed by the addition of the probe and Pd2+After 0.5h incubation, a significant fluorescence increase was observed (fig. 9 c). Heme (Heme) is reported in the literature to stimulate the production of CO in cells. The cells were pretreated with Heme (Heme) for 4h to stimulate the production of intracellular CO, followed by the addition of Pd2+At the same time, the probe was used for 0.5h, and a strong fluorescent signal was detected in the cells (FIG. 9 d). These results indicate that the fluorescent probe can monitor the change of the content of CO in the cells, which provides a reliable means for monitoring the lesion related to carbon monoxide in the human body.

Claims (3)

1. A carbon monoxide near-infrared fluorescent probe, namely DCX-CO, has the following structure:
2. the method for preparing the carbon monoxide near-infrared fluorescent probe according to claim 1, which is characterized by comprising the following reaction steps:
in N2Under protection, 0.5 equivalent of DCX-OH, 2.0 to 3.0 equivalents of allyl chloroformate and 2.0 to 3.0 equivalents of triethylamine are dissolved in 8 to 12mL of THF in a 25mL round-bottom flask, then the reaction is stirred at room temperature overnight, and after the reaction is finished, water is added for dilution, CH is used for diluting2Cl2Extraction, washing the organic layer with brine, and then with anhydrous Na2SO4Drying, filtering and concentrating the crude product with CH2Cl2And purifying by silica gel column chromatography as eluent to obtain a dark green solid product DCX-CO, namely the fluorescent probe.
3. The use of the carbon monoxide near-infrared fluorescent probe as claimed in claim 1, wherein the fluorescent probe is used for detecting the content of carbon monoxide in living cells.
CN201911084617.5A 2019-11-07 2019-11-07 Preparation and application of carbon monoxide near-infrared fluorescent probe Active CN110669503B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201911084617.5A CN110669503B (en) 2019-11-07 2019-11-07 Preparation and application of carbon monoxide near-infrared fluorescent probe

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201911084617.5A CN110669503B (en) 2019-11-07 2019-11-07 Preparation and application of carbon monoxide near-infrared fluorescent probe

Publications (2)

Publication Number Publication Date
CN110669503A true CN110669503A (en) 2020-01-10
CN110669503B CN110669503B (en) 2022-10-28

Family

ID=69086469

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201911084617.5A Active CN110669503B (en) 2019-11-07 2019-11-07 Preparation and application of carbon monoxide near-infrared fluorescent probe

Country Status (1)

Country Link
CN (1) CN110669503B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111518083A (en) * 2020-05-26 2020-08-11 湘潭大学 Preparation and application of open type fluorescent probe for detecting carbon monoxide
CN113024504A (en) * 2021-03-12 2021-06-25 湘潭大学 Preparation and application of hydrogen sulfide fluorescent probe based on isophorone-xanthene

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108219510A (en) * 2018-03-21 2018-06-29 湘潭大学 The preparation and application of peroxynitrite fluorescence probe based on hemicyanine dye
CN110128435A (en) * 2019-06-03 2019-08-16 湘潭大学 A kind of preparation and application of peroxynitrite Ratiometric fluorescent probe

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108219510A (en) * 2018-03-21 2018-06-29 湘潭大学 The preparation and application of peroxynitrite fluorescence probe based on hemicyanine dye
CN110128435A (en) * 2019-06-03 2019-08-16 湘潭大学 A kind of preparation and application of peroxynitrite Ratiometric fluorescent probe

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
W. FENG ET AL.，: "A readily available colorimetric and near-infrared fluorescent turn-on probe for detection of carbon monoxide in living cells and animals", 《SENSORS AND ACTUATORS B: CHEMICAL》 *
YU QI ET AL.，: "Real-Time Monitoring of Endogenous Cysteine Levels In Vivo bynear-Infrared Turn-on Fluorescent Probe with Large Stokes Shift", 《ANAL. CHEM》 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111518083A (en) * 2020-05-26 2020-08-11 湘潭大学 Preparation and application of open type fluorescent probe for detecting carbon monoxide
CN111518083B (en) * 2020-05-26 2022-06-28 湘潭大学 Preparation and application of open type fluorescent probe for detecting carbon monoxide
CN113024504A (en) * 2021-03-12 2021-06-25 湘潭大学 Preparation and application of hydrogen sulfide fluorescent probe based on isophorone-xanthene
CN113024504B (en) * 2021-03-12 2022-04-05 湘潭大学 Preparation and application of hydrogen sulfide fluorescent probe based on isophorone-xanthene

Also Published As

Publication number Publication date
CN110669503B (en) 2022-10-28

Similar Documents

Publication Publication Date Title
CN110540837B (en) Preparation and application of hydrogen peroxide near-infrared fluorescent probe
Feng et al. A readily available colorimetric and near-infrared fluorescent turn-on probe for detection of carbon monoxide in living cells and animals
Zhang et al. Two-photon AIE based fluorescent probe with large stokes shift for selective and sensitive detection and visualization of hypochlorite
Lu et al. A two-photon fluorescent probe for endogenous superoxide anion radical detection and imaging in living cells and tissues
Feng et al. A dual-channel probe with green and near-infrared fluorescence changes for in vitro and in vivo detection of peroxynitrite
Zhao et al. A near-infrared and two-photon ratiometric fluorescent probe with a large Stokes shift for sulfur dioxide derivatives detection and its applications in vitro and in vivo
CN108003869B (en) Fluorescent probe for detecting hypochlorite with high sensitivity and synthesis method and application thereof
Yang et al. Phenothiazine–aminothiourea–Hg (II) ensemble-based fluorescence turn-on toward iodide in aqueous media and imaging application in live cells
CN105017196A (en) Hydrazine near infrared ratio detecting fluorescent probe and application
CN110669503B (en) Preparation and application of carbon monoxide near-infrared fluorescent probe
He et al. A turn-on near-infrared fluorescent probe for detection of cysteine over glutathione and homocysteine in vivo
Zhang et al. A novel colorimetric and far-red emission ratiometric fluorescent probe for the highly selective and ultrafast detection of hypochlorite in water and its application in bioimaging
Zhou et al. A highly sensitive fluorescent probe for selective detection of cysteine/homocysteine from glutathione and its application in living cells and tissues
Zhu et al. Near-infrared cyanine-based sensor for Fe 3+ with high sensitivity: its intracellular imaging application in colorectal cancer cells
CN111518083A (en) Preparation and application of open type fluorescent probe for detecting carbon monoxide
CN111518071A (en) Preparation and application of cysteine near-infrared fluorescent probe
Liu et al. Oxidized-morpholine dressing ratiometric fluorescent probe for specifically visualizing the intracellular glutathione
Rong et al. Double-channel based fluorescent probe for differentiating GSH and H2Sn (n> 1) via a single-wavelength excitation with long-wavelength emission
Guo et al. Novel dual-site fluorescent probe for monitoring cysteine and sulfite in living cells
Yang et al. Development of a mitochondria-targeted fluorescent probe for the ratiometric visualization of sulfur dioxide in living cells and zebrafish
Gao et al. A mitochondria-targeted and deep-red emission ratiometric fluorescent probe for real-time visualization of SO 2 in living cells, zebrafish and living mice
Zhu et al. A Mitochondrial-targeted curcumin-based fluorescent probe for real-time tracking endogenous hydrogen peroxide in living cells
CN111825718B (en) Preparation and application of alkaline phosphatase fluorescent probe based on quinoline-xanthene
Chen et al. A highly selective colorimetric and fluorescent probe Eu (tdl) 2abp for H2S sensing: Application in live cell imaging and natural water
Tang et al. A Cys-regulated two-photon lysosomal targetable fluorescent probe and its application for the diagnosis of kidney diseases

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant