CN108003145A - A kind of water-soluble carbon glycosides coumarin fluorescent probe, synthetic method and application - Google Patents
A kind of water-soluble carbon glycosides coumarin fluorescent probe, synthetic method and application Download PDFInfo
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- CN108003145A CN108003145A CN201610943926.3A CN201610943926A CN108003145A CN 108003145 A CN108003145 A CN 108003145A CN 201610943926 A CN201610943926 A CN 201610943926A CN 108003145 A CN108003145 A CN 108003145A
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- 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
- C07D407/14—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 three or more hetero rings
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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
- 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
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Abstract
The invention discloses a kind of water-soluble carbon glycosides coumarin fluorescent probe, synthetic method and application.The fluorescence probe is obtained by two-step reaction, has the features such as reaction raw materials are cheap and easy to get, and reactions steps are few, and yield is high.Present invention is disclosed the multiple use of the carbon glycosides coumarin fluorescent probe, including：1. the detection of bovine serum albumin, fluorescence probe unstressed configuration in PBS solution, and after bovine serum albumin is added, fluorescence intensity increase；2. acid-base value is analyzed, pH is in the range of 3 12 for analysis, detects the fluorescence spectrum of bovine serum albumin, selectes suitable experiment condition and is tested；3. dynamic light scattering granularmetric analysis, the particle diameter before and after the dynamic light scattering spectrum analysis probe combination bovine serum albumin is utilized.
Description
Technical field
The present invention relates to a kind of water-soluble carbon glycosides coumarin fluorescent probe and its preparation method and application, specifically, relate to
And a kind of sugar charcoal glycoside fluorescent probe compounds containing tonka bean camphor structure, synthetic method and its in terms of bovine serum albumin is detected
Application.
Background technology
Recently, the interaction before large biological molecule and small molecule has attracted the attention of more and more people.In these lifes
In thing macromolecular, haemocyanin is protein most abundant in animal circulating system.Low haemocyanin can cause liver and kidney
Dirty damage, low albumen intake also results in people's malnutrition in diet.Therefore, by detecting blood or other life
The content of middle haemocyanin can obtain the health and fitness information of patient, be important method.Bovine serum albumin is the master of plasma protein
Want one of content, and be easy to get, inexpensively, stablize and the structural homology with human albumin, thus receive widely studied.
Determine that the content of bovine serum albumin is an important problem by appropriate method.In all detection methods, fluorescence
Probe is shown one's talent due to its high sensitivity and high selectivity.Therefore, new fluorescence probe is developed to get over for detecting various albumen
More to receive significant attention.
Carbohydrate is the biomolecule of a kind of aqueous solution having had and biocompatibility, and many document reports are from sugar
Design of setting out synthesis ion probe, protein-interacting body and biological radiography etc..Wherein carbon glycosides is one analogy of carbohydrate
Relatively stable carbohydrate molecule.Coumarin kind compound is more sensitive to the polarity of environment, and polarity probes molecule is due to hydrophobic effect
It is general to there are obvious fluorescence optical signals to respond.2014Qian Junhong(Dyes Pigments,2014,103:1-8) report
Probe molecule based on cumarin, have studied the influence of conjugated system, substituent and solvent polarity to probe spectral quality, and
Detection result of the compound to bovine serum albumin(BSA) is investigated.Wherein by the way that contraposition substituted benzene conjugation is connected to polar sensitive
On fluorogen cumarin, there is higher selectivity and detection sensitivity to BSA, its linear detection range to BSA is 0-
2.0mg/mL, detection are limited to 0.6 μ g/mL.But the quasi-molecule has the shortcomings of poorly water-soluble, poor biocompatibility.
In order to overcome the shortcomings of above water solubility and biocompatibility etc., our seminars have developed a variety of water
Dissolubility carbohydrate Small-molecule probe, by rhodamine and sugar by schiff bases (Spectroscopy Letters, 2015,48:578-
Or thiocarbamide (Spectrochimica Acta Part A 585):Molecular and Biomolecular
Spectroscopy 2017,173:495-501) it is connected, available for mercury ion in the detection water of selectivity, is combined with mercury ion
After Fluorescence Increasing and UV absorption can be caused to strengthen.In addition we are also reported using glucose as substrate, and two-step reaction constructs
New Type of Carbon glycosides fluorescence molecule (RSC Adv, 2016,6：18357-18363), realize the detection to bovine serum albumin, increase carbohydrate
Structure, further increases the water solubility and biocompatibility of probe.
The content of the invention
The object of the present invention is to provide a kind of water-soluble carbon glycosides coumarin fluorescent probe and preparation method thereof.
It is another object of the present invention to a kind of this fluorescence probe is applied to the detection of bovine serum albumin.
Realizing the technical solution of the present invention is：A kind of water-soluble carbon glycosides coumarin fluorescent probe, the fluorescence probe
With such as lower structure：
A kind of synthetic method of water-soluble carbon glycosides coumarin fluorescent probe, includes the following steps
By in 2 molten dichloromethane of compound, pyrrolidines and 7- (lignocaine) cumarin -3- formaldehyde, room temperature are sequentially added
18-24h is stirred, TLC is tracked to after the reaction was complete, and solvent is removed in decompression rotation, adds ethyl acetate and water extraction, and organic phase is with anhydrous
Sodium sulphate is dried, and rear filtering and concentrating, crude product is purified by column chromatography for separation, obtains the knot of target compound, wherein compound 2
Structure formula is：
Further, in column layer Xin, eluent uses volume ratio as EtOAc:PE10: 1~5: 1 mixture.
Further, compound 2 and the molar ratio of 7- (lignocaine) cumarin -3- formaldehyde are 1: 1.2, the use of pyrrolidines
Measure as the 5mol% of compound 2.
Application of the water-soluble carbon glycosides coumarin fluorescent probe of above-mentioned synthesis in bovine serum albumin detection.
The present invention has following obvious advantage：(1) fluorescent chemicals has good water solubility.(2) the fluorescence chemical combination
Thing has bovine serum albumin obvious selective, high sensitivity, and the reaction time is short.(4) pH of the fluorescent chemicals is applicable in model
Enclose wider, be 3-9.
Brief description of the drawings
Ultraviolet spectrogram of Fig. 1 water-soluble carbon glycosides coumarin fluorescents probe compound 3 to different solvents.
Fluorescence spectra of Fig. 2 water-soluble carbon glycosides coumarin fluorescents probe compound 3 to different solvents.
The bovine serum albumin detection of Fig. 3 water-soluble carbon glycosides coumarin fluorescents probe compound 3.
Fig. 4 water-soluble carbon glycosides coumarin fluorescents probe compound 3 detects the linear graph of bovine serum albumin.
Fig. 5 pH detect water-soluble carbon glycosides coumarin fluorescent probe compound 3 influence of bovine serum albumin.
The grain-size graph of Fig. 6 water-soluble carbon glycosides coumarin fluorescents probe compound 3.
Fig. 7 water-soluble carbon glycosides coumarin fluorescents probe compound 3 adds the grain-size graph after bovine serum albumin.
Embodiment
A kind of synthesis of water-soluble carbon glycosides coumarin fluorescent probe of the present invention presented below and its bovine serum albumin detect
The application test of aspect.
The synthetic route of the compounds of this invention is as follows, first with D-Glucose (1) for raw material, synthesizes corresponding furan type carbon
Glycosides (2), then react synthesis target-probe molecule 3 with 7- (lignocaine) cumarin -3- formaldehyde.
Embodiment 1
The preparation of compound 2
D-Glucose and acetylacetone,2,4-pentanedione are dissolved in 50mL water, add CoCl2, it is heated to 90 DEG C of reaction 8-10h.TLC is shown
After showing reaction completely, ethyl acetate extraction is added, organic phase decompression is spin-dried for, and obtained crude product is by recrystallizing to obtain compound 2.
1H NMR(300MHz,CDCl3) δ 6.57 (s, 1H), 4.61 (d, J=6.2Hz, 1H), 4.32 (t, J=4.6Hz,
2H), 4.19 (dd, J=10.0,4.3Hz, 1H), 3.85 (dd, J=13.0,3.7Hz, 2H), 3.76 (s, 1H), 2.52 (s,
3H),2.34(s,3H).
13C NMR(125MHz,CDCl3):δ193.9,158.2,149.2,121.1,108.4,75.9,73.7,72.1,
70.0,28.1,13.6ppm.
Anal.Calcd for C11H14O5:C,58.15；H,6.43.Found:C,58.22；H,6.35.
Embodiment 2
The preparation of compound 3
By in 2 molten dichloromethane of compound, pyrrolidines and 7- (lignocaine) cumarin -3- formaldehyde, room temperature are sequentially added
18-24h is stirred, TLC is tracked to after the reaction was complete, and solvent is removed in decompression rotation, adds ethyl acetate and water extraction, and organic phase is with anhydrous
Sodium sulphate is dried, and rear filtering and concentrating, crude product is purified by column chromatography for separation, obtains target compound 3..
1H NMR(500MHz,CDCl3) δ 7.84 (d, J=15.1Hz, 1H), 7.76 (s, 1H), 7.52 (d, J=15.2Hz,
1H), 7.33 (d, J=8.7Hz, 1H), 6.83 (s, 1H), 6.61 (s, 1H), 6.50 (s, 1H), 5.35 (s, 1H), 4.78-4.61
(m, 1H), 4.43 (s, 2H), 4.27 (s, 2H), 3.91 (s, 1H), 3.45 (d, J=6.8Hz, 4H), 2.58-2.55 (m, 4H),
2.36-2.33 (m, 2H), 2.23 (d, J=8.4Hz, 1H), 2.01 (s, 1H)
13C NMR(125MHz,CDCl3)δ185.3,158.9,155.6,150.9,148.8,145.2,137.4,129.0,
124.1,121.9,108.6,108.4,108.0,96,73.8,72.3,70.1,44.1,28.7,28.4,28.1,13.7,
11.5ppm.
Anal.Calcd for C25H27NO7:C,66.21；H,6.00；N,3.09.Found:C,66.15；H,5.89；N,
3.05.
Embodiment 3
Ultraviolet and fluorescence spectrum of the fluorescence probe in different solvents.
Solvent polarity is investigated to optical physics by detecting ultraviolet and emission spectrum of the probe molecule in different solvents
The influence of property, as shown in Figure 1, as solvent polarity increases, the ultraviolet and emission spectrum of probe has obvious Red Shift Phenomena.
As can be seen that Stokes displacement of the probe 3 in different solvents increases with the increase of solvent polarity.As in EA
Stokes displacements are 59nm, and the Stokes displacements in PBS buffer increase 112nm.At the same time as shown in Fig. 2, the spy
In PBS buffer solutions, fluorescence almost disappears pin, and quantum yield reaches minimum, and in nonpolar solvent, fluorescence is stronger, this
Kind phenomenon is probably the sedimentation due to probe in different solvents.
Analyzed from structure, probe (produces the conjugation aromatic ring of fluorescence by hydrophilic segment (saccharide ring part) and lipophilic portion
Part) composition.In proton solvent, hydrophilic segment can mutually be assembled, and lipophilic portion can be hidden in inside, in fluorescence spectra
Show as fluorescent quenching.And on the contrary, in aprotic solvent, lipophilic portion can mutually be assembled, and hydrophilic segment can be combined with each other
And inside is hidden in, Fluorescence Increasing is shown as in fluorescence spectrum.The probe detects egg to the hypersensitivity of polarity for design
White fluorescence probe is beneficial, has potential application prospect.
Embodiment 4
Fluorescent probe compounds 3 detect the ultraviolet spectrogram of bovine serum albumin
In order to inquire into the possibility that probe accurately tests bovine serum albumin content in physiological conditions, cow's serum egg has been carried out
White titration experiments.As shown in figure 3, under test conditions, the almost unstressed configuration at 530nm of probe 3, when bovine serum albumin adds
Afterwards, fluorescence is significantly increased.Gradually step up 3 solution of probe (20mmol L-1, pH=7.4) in bovine serum albumin addition
Amount, fluorescence intensity gradually increase.
As shown in figure 4, when bovine serum albumin concentration is in the range of 0-2mg/mL, the fluorescence intensity ratio of probe 3 and ox
Serum protein concentrations are in good linear relationship (R2=0.99492, y=2.8727x+1.0267), show probe 3 in the scope
It is interior to can be used for quantitatively detecting bovine serum albumin.
Embodiment 5
PH detects fluorescent probe compounds 3 influence of bovine serum albumin.
Since pH can influence the electrostatic potential of protein molecule, and then influence the combination of albumen and probe.For Optimal Experimental
Condition, have studied solution acid alkalinity (pH excursion 3-12) and front and rear fluorescence intensity is combined with bovine serum albumin to probe 3.Such as
Shown in Fig. 5, in pH=3-9, faint change is presented in probe 3 itself, and fluorescence intensity after being combined with bovine serum albumin
Trend, but work as pH>When 10, fluorescence intensity reduces rapidly.In order to simulate biosystem environment, the sensitivity of maximum, this chapter are obtained
All test jobs carry out in the PBS buffer solutions of the pH=7.4 close to physiological condition.
Embodiment 6
The fluorescent probe compounds 3 of carbon glycosides add the grain size analysis before and after bovine serum albumin
Solution middle probe 3 and the particle size of bovine serum albumin compound can be detected by DLS dynamic light scatterings.
We configure the mixed aqueous solution of bovine serum albumin and probe 3, bovine serum albumin aqueous solution, wherein 3 aqueous solution of probe, cow's serum
Protein concentration is 1.6mg/mL, and the concentration of probe 3 is 5 μM.As can be known from Fig. 6, the average grain diameter of 5 μM of probes 3 in aqueous
For 22.7nm, the average grain diameter of 3 compound of bovine serum albumin and probe is 11.2nm (Fig. 7), and bovine serum albumin is in aqueous
The spontaneous accumulation of meeting, forms particulate, when adding bovine serum albumin into probe 3, can destroy the sedimentation, form cow's serum egg
The white compound with 3, reduces the particle diameter of 3 particulate of probe.
Claims (5)
1. water-soluble carbon glycosides coumarin fluorescent probe, its structure such as general formula (I)：
2. the synthetic method of the water-soluble carbon glycosides coumarin fluorescent probe of general formula (I), it is characterised in that by the chemical combination of general formula (II)
In the molten dichloromethane of thing, sequentially add pyrrolidines and 7- (lignocaine) cumarin -3- formaldehyde, be stirred at room temperature 18-24h, TLC with
For track to after the reaction was complete, solvent is removed in decompression rotation, adds ethyl acetate and water extraction, organic phase is dried with anhydrous sodium sulfate, rear mistake
Filter concentration, crude product obtain the target compound after being purified by column chromatography for separation.
3. synthetic method as claimed in claim 2, it is characterised in that in column chromatography, eluent uses volume ratio as EtOAc：
PE 10:1~5:1 mixture.
4. synthetic method as claimed in claim 2, it is characterised in that the compound and 7- (lignocaine) tonka-bean of general formula (II)
The molar ratio of element -3- formaldehyde is 1:1.2, the dosage of pyrrolidines is the 5mol% of the compound of general formula (II).
5. application of the fluorescence probe as claimed in claim 1 in bovine serum albumin detection.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004003550A2 (en) * | 2002-06-28 | 2004-01-08 | Xanthus Life Sciences, Inc. | Individualization of therapy with anticoagulants |
| US20130059321A1 (en) * | 2011-08-31 | 2013-03-07 | University Of Southern California | Labeling of Proteins with the Fluorophore 7-amino-4-methylcoumarin (AMC) Generated Novel Proteolytic Substrates |
| CN105419783A (en) * | 2015-11-24 | 2016-03-23 | 齐鲁工业大学 | Thiophenol fluorescent probe based on 7-lignocaine-3-hydroxycoumarin structure and preparation method thereof |
| CN105602547A (en) * | 2014-10-30 | 2016-05-25 | 南京理工大学 | Water-soluble fluorescent probe based on glucoside, synthesis and application |
| CN105693673A (en) * | 2015-07-22 | 2016-06-22 | 华东理工大学 | 2,4-dinitrobenzenesulfonyl-containing coumarin compound and preparation method and application thereof |
-
2016
- 2016-11-02 CN CN201610943926.3A patent/CN108003145A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004003550A2 (en) * | 2002-06-28 | 2004-01-08 | Xanthus Life Sciences, Inc. | Individualization of therapy with anticoagulants |
| US20130059321A1 (en) * | 2011-08-31 | 2013-03-07 | University Of Southern California | Labeling of Proteins with the Fluorophore 7-amino-4-methylcoumarin (AMC) Generated Novel Proteolytic Substrates |
| CN105602547A (en) * | 2014-10-30 | 2016-05-25 | 南京理工大学 | Water-soluble fluorescent probe based on glucoside, synthesis and application |
| CN105693673A (en) * | 2015-07-22 | 2016-06-22 | 华东理工大学 | 2,4-dinitrobenzenesulfonyl-containing coumarin compound and preparation method and application thereof |
| CN105419783A (en) * | 2015-11-24 | 2016-03-23 | 齐鲁工业大学 | Thiophenol fluorescent probe based on 7-lignocaine-3-hydroxycoumarin structure and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| BAI, HY ET AL.: "Fluorescent polarity probes for identifying bovine serum albumin: Amplification effect of para-substituted benzene", 《DYES AND PIGMENTS》 * |
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Application publication date: 20180508 |