CN106833625B - A kind of two-photon lysosomal pH fluorescence probe and its preparation method and application - Google Patents
A kind of two-photon lysosomal pH fluorescence probe and its preparation method and application Download PDFInfo
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Abstract
The present invention provides a kind of two-photon lysosomal pH fluorescence probes and its preparation method and application.The probe is to construct the pH fluorescence probe based on Intramolecular electron transfer effect using benzimidazole bridging carbazole derivates.Preparation method: being dissolved in a small amount of n,N-Dimethylformamide for benzimidazole and carbazole derivates, and trim,ethylchlorosilane catalysis is added, and in envelope inner reaction tube, saturation Na is then added2CO3Solution adjusts pH to alkalescent, is concentrated under reduced pressure, silica gel post separation obtains sterling.The probe has the pK balanced close to lysosomal pHaValue.To H+With high sensitivity, good selectivity and big Stocks displacement.The probe is combining H+Front and back color change is obvious, can naked eye identification.The probe confirms that the probe and commercially available green lysosome probe have good common location using carbazole derivates as two-photon fluorescence group, using two-photon fluorescence imaging technology, can be applied to the detection that pH changes in HeLa cytase body.
Description
Technical field
The present invention relates to lysosomal pH fluorescence probe, the two-photon lysosomal pH fluorescence of specifically a kind of benzimidazole is visited
Needle and preparation method thereof and the probe are detecting the application in intracellular lysosomal pH.
Background technique
Internal pH value and many important physiology courses of cell and crganelle are closely related.Different cell and crganelles
There is different pH equilibrium valves.Lysosome is a kind of typical acidic organelles, pH value range 4.5-5.5, abnormal lyase
The variation of body pH value is related with a kind of referred to as gene genetic disease of lysosomal storage disease.It is therefore desirable to acid pH in lysosome
The variation of value carries out sensitive, accurate real-time monitoring, this has physiology and pathologic process that cell is studied from molecular level
There is important meaning.
So far, most of lysosomal pH fluorescence probe reported in the literature is single photon fluorescence probe, is typically limited to
Shortwave excites (400-560nm), and light injury and photobleaching are larger；Light injury and self-lighting, nothing equally can be also caused to cell
Method is applied to Real-time High Resolution and detects living tissue pH.Lysosome is subcellular organelle, and the pH value for detecting subcellular organelle is easy by thin
Born of the same parents' internal environment influences, and the accurate pH variation detected in subcellular organelle just needs high spatial resolution.And what last decade occurred
Two-photon technology makes its excitation wavelength be located near infrared region (700-900nm), is realizing due to that can absorb two photons simultaneously
While deep layer transmits, ultraviolet light is avoided to the damage of biological tissue and the interference of background fluorescence, can meet subcellular organelle (such as
Lysosome) high resolution detection this requirement.However the report of the lysosomal pH fluorescence probe with two-photon absorption performance is mostly
Non- Ratio-type two-photon lysosomal pH fluorescence probe.This single signal output based on fluorescence intensity change is easy by cell
The factors interference such as internal environment, probe load unevenness, stability of instrument cannot achieve quantitative detection；Opposite Ratiometric fluorescent probe
By the ratio variation of two fluorescence peaks, combining ratio fluorescence imaging can effectively eliminate these disturbing factors, realize quantitative inspection
The target of survey.Therefore, it there is an urgent need to develop effective Ratio-type two-photon lysosomal pH fluorescence probe, realizes to lysosomal pH wave
Dynamic Sensitive Detection.
Summary of the invention
An object of the present invention is to provide two-photon lysosomal pH fluorescence probe and its preparation of a kind of benzimidazole
Ratio fluorescent emission characteristics should be presented in method, the lysosomal pH fluorescence probe, be able to achieve accurate quantitative analysis detection；The second purpose is to mention
For the purposes of the probe, i.e., the application in intracellular lysosomal pH variation is being detected using two photon imaging technology.
A kind of two-photon lysosomal pH fluorescence probe of benzimidazole provided by the invention, structural formula are as follows:
A kind of preparation method of the two-photon lysosomal pH fluorescence probe of benzimidazole provided by the invention, including it is as follows
Step:
(1) in tube sealing, by 2- tolimidazole, 9- (2- (2- methoxy ethoxy) ethyl) -9H- carbazole -3- first
1~1.5:1:10~15 are dissolved in n,N-Dimethylformamide in molar ratio for aldehyde and trim,ethylchlorosilane, and 100~140 DEG C of heating are anti-
It answers 20~28 hours；
(2) saturation Na is added into reaction solution2CO3Solution adjusts solution ph to alkalescent, stirs at least 0.5 hour, uses
CH2Cl2Extraction 3 times merges organic phase, anhydrous Na2SO4After drying, vacuum distillation obtains crude product；
(3) crude product obtains sterling through silica gel post separation.
Its synthetic route is as follows:
2- tolimidazole in the step (1), 9- (2- (2- methoxy ethoxy) ethyl) -9H- carbazole -3- formaldehyde
It is 1.2:1:12 with the molar ratio of trim,ethylchlorosilane, reaction temperature 100, the reaction time 24 hours.
Mixing time is 1 hour in the step (2).
Probe of the invention has good permeability of cell membrane, can target and be positioned at lysosome, and can apply to cell
The detection of interior lysosomal pH.
Compared with existing pH fluorescence probe, the probe that the present invention synthesizes has the advantage that (1) using tube sealing as anti-
It answers container to reduce solvent usage amount, is conducive to environmental protection；(2) big Stokes displacement is conducive to reduce in angiographic procedure
The interference of exciting light；(4) there is suitable pKaValue is suitable for detecting pH variation in lysosome；(5) good selectivity, this spy
For H+Response not by the interference of common metal ion and amino acid；(6) this probe is based on Intramolecular electron transfer (ICT)
Ratio fluorescent emission characteristics is presented during protonation and deprotonation in principle design, realizes accurate quantitative analysis detection；(7)
Solution colour variation is obvious under natural light and ultraviolet lamp, can observe by the naked eye；(8) probe has good two-photon
Absorbent properties can not only be targeted label lysosome with single, double photon, while can utilize two-photon technology high resolution detection lyase
The variation of internal pH.(9) this probe synthesis step is simple, low in cost, has biggish practical value.
Detailed description of the invention
The uv absorption spectra of 1 middle probe of Fig. 1 embodiment of the present invention under different ph values.
1 middle probe of Fig. 2 embodiment of the present invention identifies H under natural light+Front and back color change.
The fluorescence spectra of 1 middle probe of Fig. 3 embodiment of the present invention under different ph values.
1 middle probe of Fig. 4 embodiment of the present invention identifies H in the UV lamp+Front and back color change.
Fluorescence intensity ratio (the F of 1 middle probe of Fig. 5 embodiment of the present invention454nm/F514nm) with the change curve of pH value.
1 middle probe of Fig. 6 embodiment of the present invention is in the presence of common metal ion and amino acid to H+Selectivity.
The pH Response Mechanism of 1 middle probe of Fig. 7 embodiment of the present invention.
1 middle probe of Fig. 8 embodiment of the present invention and commercially available green lysosome probe (Lyso Tracker Green DND-
26) single photon and two photon imaging figure of 30min are incubated for jointly under conditions of pH value 7.4.
1 middle probe of Fig. 9 embodiment of the present invention is from HeLa cell in different pH value (pH 6.0,5.5,5.0,4.5,4.0)
Under the conditions of be incubated for the two photon imaging figure of 30min jointly.
Specific embodiment
Embodiment 1
The synthesis step of probe of the present invention is as follows:
(1) in tube sealing, by 2- tolimidazole 0.446g, 9- (2- (2- methoxy ethoxy) ethyl) -9H- click
Azoles -3- formaldehyde 0.237g and trim,ethylchlorosilane are dissolved in n,N-Dimethylformamide, 100 DEG C of heating reactions 24 by a mole 2.28ml
Hour.
(2) saturation Na is added into reaction solution2CO3It after solution adjusts solution ph to alkalescent, stirs 1 hour, uses
CH2Cl2Extraction 3 times merges organic phase, anhydrous Na2SO4After drying, vacuum distillation obtains crude product.
(3) crude product obtains sterling through silica gel post separation.1H-NMR(DMSO-d6, 400MHz) and δ 12.59 (m, 1H), 8.47
(d, J=1.2Hz, 1H), 8.24 (d, J=7.6Hz, 1H), 7.83 (d, J=16.4Hz, 1H), 7.77-7.79 (dd, J=
1.2Hz, 1H), 7.64-7.69 (dd, J=8.2Hz, 2H), 7.59 (d, J=7.2Hz, 1H), 7.45-7.49 (m, 2H), 7.22-
7.26 (m, 2H), 7.13-7.20 (m, 2H), 4.59 (t, J=5.4Hz, 2H), 3.81 (t, J=5.4Hz, 2H), 3.46 (t, J=
4.8Hz, 2H), 3.31 (t, J=4.6Hz, 2H), 3.12 (s, 3H) ppm.MS (MALDI-TOF) m/z 412.2022 [M+H]+
Embodiment 2
The stock solution for being 1mM with DMSO compound concentration by the probe in embodiment 1.Water/DMSO (V/V=4/ is used in experiment
1) probe dilution is made 30 μM of its final concentration by system.The pH value of the system is adjusted with the HCl of 1mol/L, records condition of different pH
Under uv absorption spectra (Fig. 1).It is gradually reduced as pH value is reduced to by 6.8 the absorption peak at 2.5,359nm, 396nm
The absorption peak at place successively enhances, while there are an apparent isoelectric points at 380nm.Fig. 2 shows solution colour by no discoloration
For yellow, left figure is the colourless solution for not being loaded product, and right figure is the yellow solution for adding HCl in sample.
Embodiment 3
It is same that probe dilution is subjected to fluorescence spectroscopic titration, fixed excitation to 10 μM with water/DMSO (V/V=4/1) system
Wavelength is 360nm, records the fluorescence emission spectrum under condition of different pH.As shown in figure 3, under the neutrallty condition of pH 6.8, it should
The maximum fluorescence emission of probe is located at 454nm, and with the reduction of pH, the fluorescent emission at 454nm is gradually decreased, in 514nm
There is a new fluorescent emission and significantly increases in place, and significant ratio fluorescent emission characteristics (F is presented454nm/F514nm).Simultaneously
Occurs a clearly isoelectric point at 500nm.Under ultraviolet light irradiation, the color of solution becomes right from the blue of left side sample
The green (Fig. 4) of face sample.According to fluorescence intensity ratio (F454nm/F514nm) from the matched curves of different pH value calculate pKaValue is
4.46 (Fig. 5).
Embodiment 4
The probe (10 μM) in embodiment 1 is investigated in the presence of common metal ion and amino acid, to H+Selectivity.Such as
Shown in Fig. 6, respectively different pH (pH 7.0,4.5 and 2.0) under the conditions of, to common metal ion and amino acid almost without sound
It answers, it was demonstrated that the probe is to H+With very high selectivity.The sequence and concentration of each substance be successively in Fig. 6 are as follows: (1) blank；(2)K+
(150mM)；(3)Na+(150mM)；(4)Mn2+(0.2mM)；(5)Zn2+(0.2mM)；(6)Ca2+(10mM)；(7)Cd2+
(0.2mM)；(8)Co2+(0.2mM)；(9)Pb2+(0.2mM)；(10)Ni2+(0.2mM)；(11)Mg2+(2mM)；(12)Hg2+
(0.2mM)；(13)Fe2+(0.2mM)；(14)Fe3+(0.2mM)；(15)Al3+(0.2mM)；(16) histidine (0.2mM)；(17)；
Leucine (0.2mM)；(18) glycine (0.2mM)；(19) arginine (0.2mM)；(20) lysine (0.2mM)；(21) figured silk fabrics ammonia
Sour (0.2mM)；(22) serine (0.2mM)；(23) vitamin C (2mM)
Embodiment 5
By probe, commercially available green lysosome probe and the HeLa cell in embodiment 1 in 7.4 condition of pH value in 37 DEG C, 5%
CO2Incubator in be incubated for 30min jointly, observe fluorescence imaging under single photon microscope and Two Photon Fluorescence respectively.Gu
Determining excitation wavelength is respectively 760nm and 488nm, and emission band collects blue channel (420-460nm) and green channel respectively
(500-550nm).As shown in figure 8, comparing this probe with commercially available probe can be applied to lysosomal pH imaging；First behavior two-photon
Image, the second behavior single photon image figure, two photon imaging figure fluorescence intensity are significantly stronger than single photon image figure, illustrate this spy
Needle penetration capacity strong under Two Photon Fluorescence.
Embodiment 7
By the probe in embodiment 1 from HeLa cell respectively in the condition of different pH (6.0,5.5,5.0,4.5,4.0)
Under in 37 DEG C, 5%CO2Incubator in be incubated for 30min jointly, then with the PBS buffer solution of corresponding pH value wash three times,
It is observed under Two Photon Fluorescence, fixed excitation wavelength is 760nm, collects blue channel (420-460nm) and green channel respectively
(500-550nm) fluorescence.The experimental results showed that cell issues bright blue light and green light when pH 6.0, and as pH value reduces
The quenching of cell blue-fluorescence, green fluorescence are remarkably reinforced, and present ratio fluorescent emission characteristics (Fig. 9).
Claims (4)
1. a kind of two-photon lysosomal pH fluorescence probe of benzimidazole is detecting the application in intracellular lysosomal pH, described
Using being that non-medical diagnosis on disease and non-disease are treated, the structural formula of the two-photon lysosomal pH fluorescence probe of the benzimidazole
Are as follows:
2. a kind of two-photon lysosomal pH fluorescence probe of benzimidazole as described in claim 1 is detecting intracellular lyase
Application in body pH, which is characterized in that the fluorescence probe preparation step:
(1) in tube sealing, by 2- tolimidazole, 9- (2- (2- methoxy ethoxy) ethyl) -9H- carbazole -3- formaldehyde and
1~1.5:1:10~15 are dissolved in n,N-Dimethylformamide, 100~140 DEG C of heating reactions 20 to trim,ethylchlorosilane in molar ratio
~28 hours；
(2) saturation Na is added into reaction solution2CO3Solution adjusts solution ph to alkalescent, stirs at least 0.5 hour, uses
CH2Cl2Extraction 3 times merges organic phase, anhydrous Na2SO4After drying, vacuum distillation obtains crude product；
(3) crude product obtains sterling through silica gel post separation.
3. a kind of two-photon lysosomal pH fluorescence probe of benzimidazole as claimed in claim 2 is detecting intracellular lyase
Application in body pH, which is characterized in that 2- tolimidazole in the step (1), 9- (2- (2- methoxy ethoxy) second
Base) molar ratio of -9H- carbazole -3- formaldehyde and trim,ethylchlorosilane is 1.2:1:12,100 DEG C of reaction temperature, the reaction time 24 is small
When.
4. a kind of two-photon lysosomal pH fluorescence probe of benzimidazole as claimed in claim 2 is detecting intracellular lyase
Application in body pH, which is characterized in that mixing time is 1 hour in the step (2).
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| CN108329301B (en) * | 2018-03-27 | 2020-10-02 | 安徽大学 | Two-photon pH ratio measurement fluorescent probe for monitoring autophagy of cells and preparation method and application thereof |
| CN109928949B (en) * | 2018-09-12 | 2023-05-26 | 兰州大学 | Preparation of fluorescent probe and application of long-term stable imaging lysosome thereof |
| CN109574910B (en) * | 2018-12-19 | 2021-07-02 | 山西大学 | Carbazole derivative MCAB as well as preparation method and application thereof |
| CN111171004B (en) * | 2020-02-26 | 2021-08-24 | 陕西科技大学 | (E) Preparation method of 2- (2- (9-alkyl) carbazole-3-) vinyl-benzimidazole |
| CN111303127B (en) * | 2020-02-26 | 2021-10-19 | 陕西科技大学 | (E)2- (2- (9-alkyl) carbazole-3-) vinyl-benzimidazole and preparation method thereof |
| CN113429335B (en) * | 2021-06-25 | 2023-05-16 | 安徽大学 | Lysosome-targeted dual-response two-photon fluorescent probe and preparation method and application thereof |
| CN113831291A (en) * | 2021-09-29 | 2021-12-24 | 山西大学 | Benzimidazole-based multifunctional lysosome pH probe and preparation method and application thereof |
| KR102699053B1 (en) * | 2022-02-28 | 2024-08-27 | 고려대학교 산학협력단 | Two-photon fluorescent probes for simultaneously detecting cytosolic calcium ions and lysosomal protons |
| CN115093381B (en) * | 2022-07-20 | 2023-07-25 | 安徽师范大学 | Polarity response small molecule fluorescent probe based on benzothiadiazole and preparation method and application thereof |
| CN117263915B (en) * | 2023-11-23 | 2024-04-05 | 山东海化集团有限公司 | Sulfonate terpyridine derivative and preparation method and application thereof |
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