CN109020988A - A kind of application of the Rhodamine fluorescent probe of novel triazole compound in Hela cell imaging - Google Patents
A kind of application of the Rhodamine fluorescent probe of novel triazole compound in Hela cell imaging Download PDFInfo
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Abstract
The present invention relates to a kind of application of the Rhodamine fluorescent probe of novel triazole compound in Hela cell imaging.The fluorescence probe has structure shown in Formulas I:
Description
Technical field
The invention belongs to organic synthesis and cell imaging fields, and in particular to a kind of Luo Dan of novel triazole compound
Application of the bright fluorescence probe in Hela cell imaging.
Background technique
With the rapid development of industry, while bringing economic benefits, brought pollution also constitutes greatly environment
Threat.And heavy metal ion Hg2+Pollution be even more can not be ignored.Mercury is arranged as one of the heavy metal ion most poisoned
It is put into soil or water body, life entity is enriched with by food chain and is threatened, therefore and the various diseases such as alzheimer ' of initiation
Silent disease, minamata disease, acrodynia, uremia, have seriously affected people's lives.Based on 1,2,3- triazole-rhodamine
Fluorescence probe it has been reported that still there has been no the plurality of probes be applied to cell imaging report.The present invention provide it is a kind of by
The Hg of rhodamine hydrazides and triazole carboxylate one-step method preparation high sensitivity2+Ion identification probe, and by the probe application in
Cell imaging.
Summary of the invention
The present invention provides a kind of triazole-rhodamine probe of Formulas I structure, it is characterised in that Formulas I structure is as follows:
Another embodiment of the present invention provides the preparation method of above-mentioned compound of formula I, it is characterised in that including walking as follows
It is rapid:
Compound 1 and compound 2 are dissolved in CH2Cl2In, at Fe (acac)3And Et3Compound of formula I is obtained under the action of N；
Wherein the molar ratio of compound 1 and compound 2 is 1:0.8-1.0, Fe (acac)3Mole dosage be compound 1
0.08-0.1 times, every mM of compound 1 uses CH2Cl2Volume be 12-15mL, use Et3The volume of N is 0.5-
0.6mL.Reaction temperature preferably carries out at room temperature, and the reaction time is 20-24 hours preferred.
Another embodiment of the present invention provides compound of formula I in detection Hg2+In application.
Another embodiment of the present invention provides application of the compound of formula I in HeLa cell imaging.
Compared with the prior art, the advantages of the present invention are as follows: the present invention utilizes ferric acetyl acetonade (Fe (acac)3) be used as and urge
Agent successfully realizes triazole-rhodamine probe of one-step synthesis method Formulas I structure, and the said derivative that the present invention synthesizes
To Hg2+Detection sensitivity it is high, and HeLa cell imaging can be used successfully to.
Detailed description of the invention
Fig. 1 is compound of formula I1H NMR figure；
Fig. 2 is compound of formula I13C NMR figure；
Fig. 3 is the HRMS figure of compound of formula I；
Fig. 4 is the fluorescence selectivity figure of compound of formula I, excitation wavelength 563nm；Fluorescence titration figure, illustration are at 584nm
The fluorescence intensity change of system；
Fig. 5 is the HeLa cell live cell fluorescent image of the embodiment of the present invention 5.
Specific embodiment
For the ease of a further understanding of the present invention, examples provided below has done more detailed description to it.But
It is that these embodiments are only not supposed to be a limitation to the present invention or implementation principle for better understanding invention, reality of the invention
The mode of applying is not limited to the following contents.
Embodiment 1
Compound 1 (1.0mmol) and compound 2 (0.8mmol) is dissolved in CH2Cl2In (12mL), Fe is added at room temperature
(acac)3(0.08mmol) and Et3N (0.5mL) is stirred to react 24 hours, and TLC detection raw material completely disappears, reaction solution concentration
Afterwards, silica gel column chromatography (200-300 mesh silica gel) is carried out, is eluant, eluent with petrol ether/ethyl acetate (V:V=3:1~4:1), obtains
Compound of formula I 695mg, yield 94.7%.As shown in Figure 1:1H NMR(400MHz,CDCl3)δ8.08(s,1H),8.00(d,J
=7.0Hz, 1H), 7.91 (d, J=9.0Hz, 2H), 7.85 (d, J=3.7Hz, 2H), 7.57-7.50 (m, 2H), 7.32 (d, J
=5.5Hz, 3H), 7.19 (d, J=7.2Hz, 1H), 6.94 (s, 1H), 6.92 (s, 1H), 6.76 (d, J=9.4Hz, 2H),
6.36 (m, 4H), 3.82 (s, 3H), 3.32 (dd, J=13.3,6.4Hz, 8H), 1.14 (t, J=6.9Hz, 12H)；13C NMR
(101MHz,CDCl3)δ164.99,159.55,158.43,153.85,151.27,149.17,148.97,136.88,
133.13,132.76,129.51,129.39,129.01,128.97,128.33,128.02,124.15,123.54,120.73,
114.29,108.05,104.57,97.66,77.32,77.00,76.69,66.33,55.53,44.34,29.65,
12.57.HRMS(ESI)(m/z):[M+H]+calcd for C44H44N7O4,734.3455；found,734.3454.
Embodiment 2
Compound 1 (1.0mmol) and compound 2 (1.0mmol) is dissolved in CH2Cl2In (15mL), Fe is added at room temperature
(acac)3(0.1mmol) and Et3N (0.6mL) is stirred to react 20 hours, and TLC detection raw material completely disappears, after reaction solution concentration,
It carries out silica gel column chromatography (200-300 mesh silica gel), is eluant, eluent with petrol ether/ethyl acetate (V:V=3:1~4:1), obtains Formulas I
Compound 682mg, yield 92.9%.
Embodiment 3
Compound 1 (1.0mmol) and compound 2 (1.0mmol) is dissolved in CH2Cl2In (15mL), Et is added at room temperature3N
(0.6mL), after being stirred to react 20 hours, TLC is shown in addition to compound 1 and 2, does not generate new point (i.e. there is no reactions).
Embodiment 4
Detection is illustrated in figure 4 in DMF- water (v/v=1:1, Tris-HCl, pH=7.4) solution, each ion (4.67
×10-5Mol/L) there are compounds of Formula I (1 × 10-5Mol/L fluorescence selectivity figure) and to Hg2+Fluorescence titration spectrum
(inset) at 584nm system fluorescence intensity change.In fluorescence selectivity figure under the irradiation of 563nm exciting light, in addition to Hg2+,
The addition of his ion is without obvious characteristic emission peak and color change.Hg is added2+Afterwards, fluorescence intensity obviously increases at 584nm
By force and with pink color change.Figure of fluorescence intensity changes compound of formula I (1 × 10-5Mol/L Hg) is gradually added dropwise2+When fluorescence light
Spectrogram.With Hg2+Concentration increase, the fluorescence intensity of system is gradually increased, and works as Hg2+Concentration reaches 4.67 × 10-5When mol/L,
System fluorescence intensity reaches maximum, at this time Hg2+Concentration is 4.67 times of Formulas I concentration and probe concentration.And work as Hg2+Concentration is more than the concentration
When, with Hg2+Concentration increases, and system fluorescence intensity reduces, 2.67 × 10-5~4.33 × 10-5It is glimmering in mol/L concentration range
Luminous intensity and Hg2+Concentration is linearly related, R2=0.94815.
5 cell imaging application of embodiment
In 37 DEG C of CO2It cultivates HeLa cell 24 hours and is tested in cell incubator.As shown in figure 5, A. is in DMEM
The bright-field imagery of HeLa cell under culture solution；B. under DMEM culture solution HeLa cell fluorescence imaging；C. compound of formula I exists
The bright-field imagery of HeLa cell；D. fluorescence imaging of the compound of formula I in HeLa cell；E. compound of formula I is in HeLa cell to Hg2+
Bright-field imagery；F. compound of formula I is in HeLa cell to Hg2+Fluorescence imaging effect.The concentration of compound of formula I be 1.0 ×
10-5Hg is added in mol/L2+Concentration be 2.67 × 10-5mol/L.It is above-mentioned the experimental results showed that compound of formula I of the invention is available
In cell imaging.
Claims (5)
1. a kind of triazole of Formulas I structure-rhodamine probe, it is characterised in that Formulas I structure is as follows:
2. the preparation method of compound of formula I described in claim 1, it is characterised in that include the following steps:
Compound 1 and compound 2 are dissolved in CH2Cl2In, at Fe (acac)3And Et3Compound of formula I is obtained under the action of N.
3. preparation method as claimed in claim 2, it is characterised in that the molar ratio of compound 1 and compound 2 is 1:0.8-1.0,
Fe(acac)3Mole dosage be 0.08-0.1 times of compound 1, every mM of compound 1 uses CH2Cl2Volume be 12-
15mL uses Et3The volume of N is 0.5-0.6mL.
4. the described in any item preparation methods of claim 2-3, it is characterised in that reaction temperature preferably carries out at room temperature, reaction
Time is 20-24 hours preferred.
5. application of the compound of formula I described in claim 1 in HeLa cell imaging.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113637027A (en) * | 2021-07-22 | 2021-11-12 | 海南师范大学 | Phenyl triazole dicarboxylic acid-rhodamine B derivative fluorescent probe and preparation method and application thereof |
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| CN102746313A (en) * | 2012-06-20 | 2012-10-24 | 山东大学 | Rhodamine-B hydrazide derivative containing 1,2,4-triazole structural unit, preparation method and application thereof |
| CN106977503A (en) * | 2017-04-07 | 2017-07-25 | 常州大学 | The method that iron catalyzes and synthesizes penta azacyclo |
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2018
- 2018-09-12 CN CN201811071091.2A patent/CN109020988B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102746313A (en) * | 2012-06-20 | 2012-10-24 | 山东大学 | Rhodamine-B hydrazide derivative containing 1,2,4-triazole structural unit, preparation method and application thereof |
| CN106977503A (en) * | 2017-04-07 | 2017-07-25 | 常州大学 | The method that iron catalyzes and synthesizes penta azacyclo |
Non-Patent Citations (4)
| Title |
|---|
| JIANLING LI等: "The structural properties of 5-methyl-2-phenyl-2H-1,2,3-triazole-4-carboxylic acid and chromogenic mechanism on its rhodamine B derivatives to Hg2+ ions", 《SPECTROCHIMICA ACTA PART A: MOLECULAR AND BIOMOLECULAR SPECTROSCOPY》 * |
| SHIUE-SHIEN WENG等: "Transesterification catalyzed by iron(III) b-diketonate species", 《TETRAHEDRON》 * |
| 丁国华: "系列1,2,3-三氮唑化合物与罗丹明B的合成、显色反应及其与球状蛋白的相互作用", 《海南师范大学硕士学位论文》 * |
| 丁国华等: "一种含有1" 2" 3-三氮唑基团的罗丹明B衍生物的合成及其金属离子响应", 《海南师范大学学报(自然科学版)》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113637027A (en) * | 2021-07-22 | 2021-11-12 | 海南师范大学 | Phenyl triazole dicarboxylic acid-rhodamine B derivative fluorescent probe and preparation method and application thereof |
| CN113637027B (en) * | 2021-07-22 | 2022-04-05 | 海南师范大学 | Phenyl triazole dicarboxylic acid-rhodamine B derivative fluorescent probe and preparation method and application thereof |
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