CN111253934B - Two-photon fluorescent probe and preparation and application thereof - Google Patents
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Abstract
The invention relates to a two-photon fluorescent probe with obviously enhanced fluorescence intensity in the presence of glutathione-S-transferase. The structure of the fluorescent probe is that
Wherein R is 1 、R 2 Is H, alkyl, aryl or a heteroatom-containing substituent. The invention provides a fluorescent probe for detecting glutathione S-transferase by two-photon excitation. According to the invention, an optimized nitrobenzene structure is introduced on a fluorescent parent body with a larger two-photon absorption section as an active center for recognition and reaction with glutathione-S-transferase, and the difference of the fluorescence intensity of a reactant and a product is utilized to realize the two-photon excitation fluorescence detection of the glutathione-S-transferase.
Description
Technical field:
the invention relates to the field of fluorescent probes, in particular to a synthetic method of a two-photon fluorescent probe and application of the two-photon fluorescent probe in detection of glutathione-S-transferase.
The background technology is as follows:
glutathione s-transferase (GST) is an important detoxification enzyme that catalyzes the nucleophilic addition reaction of Glutathione (GSH) to exogenous substances and endogenous electrophiles, and the resulting adduct is then expelled from the body, thereby achieving a detoxification effect. The expression level of GST in cancer cells is an important indicator for determining its sensitivity to chemotherapy. Three important isoenzymes in the cytoplasm (subtype A, M, P) are often overexpressed in drug resistant tumors or tumor cancer cells, so in order to detect anticancer drug resistance, it is necessary to develop a highly sensitive probe capable of monitoring the GST isoenzyme content in mammalian tumor cells.
Currently, only a few methods for detecting GST activity have been developed, such as 1-chloro-2, 4-dinitrobenzene (CDNB) is a widely used detection reagent, but its application is limited by the disadvantages of low sensitivity (common light absorption photometry), high background noise and poor selectivity.
The fluorescent probe technique is one of means for effectively detecting GST because the technique is relatively low in technical requirements, easy to put into practical use, and high in detection sensitivity. A fluorescent probe with application prospect has the advantages of obvious fluorescence change before and after action, quick response to target molecules, good selectivity, simple synthesis and the like. Tetsuo Nagano et al discloses a fluorescent probe DNAT-Me (structure see FIG. 1,Tetsuo Nagano et al, J.am.chem.Soc.,2008,130,14533) for detecting GST, which increases fluorescence due to inhibition of the photoelectron transfer effect (PeT) after addition of GST to GSH, thereby detecting the presence of GST, but the fluorescence properties involved in the detection mechanism of the probe are severely dependent on the pH of the environment, thereby limiting its use to some extent. Then, subsequently Yuuta Fujikawa et al continued to develop a pH insensitive fluorescent probe 3,4-DNADCF (structure see FIG. 1,Yuuta Fujikawa et al, chem. Commun.,2015,51,11459) against this problem. However, both of the above probes specifically respond to only P-type GST, and in practical applications, a fluorescent probe having a broad-spectrum response to various isozymes is sometimes required. Ralf Mongenson et al thus disclose a fluorescent probe DNs-CV (structure: see FIG. 1,Ralf Morgenstern et al, J.Am. Chem. Soc.,2011,133,14109) for detection of various GST isozymes, yet the probe is still capable of non-enzymatic reaction with GSH to some extent without GST catalysis to produce a large background noise. Therefore, it is of great importance to develop fluorescent probes with higher sensitivity and signal-to-noise ratio for detection of various GST isozymes in vitro water environments and biological samples such as human cancer cells.
The invention comprises the following steps:
the invention aims at the problems, and provides a preparation method and application of a fluorescent probe which can be used for detecting various GST isozymes in an in-vitro water environment of a living body and a biological sample such as human cancer cells by two-photon excitation fluorescence.
The invention adopts the following technical scheme: and introducing an optimized nitrobenzene structure on a fluorescent parent body with a larger two-photon absorption section as an active center for recognition and reaction with glutathione-S-transferase, and utilizing the difference of the fluorescence intensity of a reactant and a product to realize the two-photon excitation fluorescence detection GST. The general formula of the fluorescent probe is as follows:
in the general formula I, R 1 、R 2 Is H, alkyl, aryl or a heteroatom-containing substituent. R is R 1 、R 2 When the alkyl is aryl, the C is 1 ～C 20 Alkyl, aryl, preferably C 1 ～C 10 Alkyl, aryl; r is R 1 、R 2 When the substituent containing a hetero atom is a sulfonic acid group, a carboxyl group, a hydroxyl group, a halogen, a halomethyl group, an amino group, an alkoxy group, a cyano group or a nitro group.
The compound shown in the general formula I is subjected to two-photon excitation by adopting infrared laser (740-850 nm) which is completely separated from an emission light wave band (500-600 nm) and is easier to penetrate through a biological sample, so that the compound shown in the general formula I is used for detecting the external water environment of the organism and glutathione-S-transferase in the biological sample such as human cancer cells, and the compound with the structure shown in the general formula II is generated after the enzyme action, so that fluorescence is obviously enhanced, and the compound shown in the general formula I and the compound shown in the general formula II both have two-photon absorption performance, so that the two-photon excitation fluorescence detection of the glutathione-S-transferase can be realized in the process.
In the general formula II, R 1 Is H, alkyl, aryl or a heteroatom-containing substituent, R 2 is-OH or-O - 。R 1 In the case of alkyl or aryl groups, this is generally C 1 ～C 20 Most preferably C 1 ～C 10 ；R 1 When the substituent containing a hetero atom is a substituent containing a sulfonic acid group, a carboxyl group, a hydroxyl group, a halogen, an amino group, an alkoxy group, a cyano group or a nitro group.
The object of the invention is also achieved by:
a synthesis method of a fluorescent probe with GST detection function comprises the following steps:
(1) Synthesizing a nitrobenzene compound III containing sulfonic groups by taking a nitrofluorobenzene compound and sodium sulfite as raw materials;
(2) Synthesizing a nitrobenzene compound IV containing chlorosulfonyl by taking a compound III and thionyl chloride as raw materials;
(3) The fluorescent probe shown in the general formula I is synthesized by taking the compounds II and IV as raw materials.
In the above synthesis method of the fluorescent probe with GST detection function, the substituent of the nitrofluorobenzene compound in the step (1) is alkyl, aryl or heteroatom-containing substituent; when the substituent is alkyl or aryl, C is 1 ～C 20 Alkyl, aryl, preferably C 1 ～C 10 Alkyl, aryl; when the substituent is a heteroatom-containing substituent, the substituent is a sulfonic acid group, a carboxyl group, a hydroxyl group, a halogen, a halomethyl group, an amino group, an alkoxy group, a cyano group or a nitro group.
According to the synthesis method of the fluorescent probe with the GST detection function, the reaction condition in the step (1) is that a nitrofluorobenzene compound, sodium sulfite, water, methanol and ethanol are added into a three-neck flask, the molar ratio of the nitrofluorobenzene compound to the sodium sulfite is 1:1-1:5, and the volume ratio of the water to the alcohol is 1:2-1:10; starting a heating stirrer, controlling the temperature at 30-80 ℃, heating and refluxing for 5-24 hours, cooling the reaction to room temperature, and spin-drying to obtain the compound III.
In the synthesis method of the fluorescent probe with the GST detection function, the reaction condition in the step (2) is that a compound III and thionyl chloride are added into a three-neck flask under the protection of inert gas such as nitrogen, and the molar ratio of the compound III to the thionyl chloride is 1:2.5-1:10; starting a heating stirrer, heating and refluxing for 1-5 h at the temperature of 40-80 ℃, cooling to room temperature, and spin-drying to obtain the compound IV.
The reaction condition in the step (3) is that a compound II and methylene dichloride are added into a three-neck flask, a stirrer is started, reactants are cooled to-10-0 ℃, a compound IV dissolved in the methylene dichloride is dropwise added under the condition of stirring and nitrogen protection, the mol ratio of the compound II to the compound IV is 1:1-1:5, a few drops of triethylamine are added after the dropwise addition, the temperature is gradually raised to room temperature, stirring is carried out for 0.5-5 h, and the fluorescent probe shown in the general formula I is obtained by recrystallisation of methylene dichloride and methanol after spin drying.
A fluorescent probe prepared according to the above synthesis method.
The fluorescent probe prepared according to the synthesis method is applied to detection of various GST isozymes in an in vitro water environment and biological samples such as human cancer cells.
The invention has the beneficial effects that:
the invention uses aromatic nucleophilic substitution (S) of nitro fluorobenzene compound and sodium sulfite in water-alcohol mixed solvent N Ar) to prepare an optimized recognition group skeleton, then connecting the recognition group skeleton with a naphthalimide fluorescent parent with two-photon absorption performance to prepare a required fluorescent probe, wherein the fluorescent probe has obviously enhanced fluorescence intensity in the presence of various GST isozymes, and can be excited by two photons by infrared laser, so that the emitted light and the excitation light are completely separated to eliminate the influence of the excitation light on detection, the biological sample is easier to penetrate, the influence of background fluorescence on the detection result is reduced, and the external water environment of the organism and various GST isozymes in biological samples such as human cancer cells can be detected with high sensitivity, thereby having important significance for further researching the physiological and pathological roles of GST in the organism. Compared with the existing detection technologies, the fluorescent probe has the advantages of less cost investment, simple synthetic route and convenient post-treatment.
Description of the drawings:
the disclosed fluorescent probes for detecting GST as exemplified in the background of FIG. 1;
FIG. 2 is a flow chart of the synthesis of fluorescent probe NIL in examples 1 to 4;
FIG. 3 fluorescence spectral response of fluorescent probe NIF to GST extracted from liver in example 5;
FIG. 4 is an enzymatic response curve of probe NIH to various GST isozymes in example 6;
FIG. 5 detection of GST in human cancer cells by probe NIH in example 7
The specific embodiment is as follows:
examples are provided to further illustrate the invention, but the invention is not limited to the examples.
Example 1 synthesis of nitrofluorobenzene compound corresponding to the probe NIL recognition group:
into a 1000mL three-necked flask, 12.5g (60 mmol) of 1, 5-difluoro-2, 4-dinitrobenzene, 6.66g (66 mmol) of triethylamine and 200mL of tetrahydrofuran were charged, and 6.76g (66 mmol) of dimethylamine in 100mL of tetrahydrofuran was added dropwise over 1 hour. Starting a stirrer, stirring for 2 hours, spin-drying, adding water, standing, filtering, and drying to obtain the nitrofluorobenzene compound corresponding to the NIL recognition group.
Example 2 synthesis of nitro compound with sulfonic acid group corresponding to the probe NIL recognition group:
30mmol of a nitrofluorobenzene compound corresponding to an NIL recognition group, 40mL of ethanol and 20mL of methanol are added into a 500mL three-necked flask, a transparent solution is obtained by heating, sodium sulfite is dissolved in 40mL of water, 20mL of ethanol is added into the solution to obtain a suspension, the suspension is added into the solution, stirring and refluxing are carried out at 60 ℃ for 20h, and 8.7g of yellow solid is obtained by spin-drying after the reaction is cooled to room temperature.
Example 3 synthesis of probe NIL recognition group:
5mmol of nitro compound with sulfonic group corresponding to NIL recognition group and 50mmol of thionyl chloride are added into a 100mL three-neck flask, stirred for 4h at 80 ℃, and dried by spinning to obtain the recognition group of the probe NIL.
Example 4 synthesis of probe NIL:
into a 100mL three-necked flask, 0.269g (1 mmol) of 4-hydroxy-N-butyl-1, 8 naphthalimide was added, 15mL of methylene chloride was added under nitrogen protection, cooled to 0℃and NIL recognition group dissolved in 30mL of methylene chloride was added dropwise, 0.11g (1.1 mmol) of triethylamine was added, gradually warmed to room temperature, stirred for 2 hours, dried by spinning, and recrystallized with methylene chloride and methanol to obtain 0.518g of brown solid, namely probe NIL (structure of the compound was determined by nuclear magnetism and ultraviolet detection).
Example 5 fluorescence spectral response of probe NIF to GST extracted from liver:
as shown in FIG. 3, the final concentration of 20. Mu.M of NIF, 1mM of GSH and 0.0125mg/mL of GST extracted from liver were contained in the microplate wells having a final volume of 200. Mu.L, and the buffer was HEPES at pH 7.4, and the change in fluorescence spectrum within 1h was detected by the microplate reader, so that the fluorescence intensity was remarkably enhanced with the lapse of time, and thus the fluorescence detection of GST by the probe NIF was enabled.
Example 6 enzymatic response curves of probe NIH for various GST isozymes:
FIG. 4 shows the same procedure as in example 5 except that the Michaelis equation curve of NIH versus GST of A, M, P subtype can be measured by varying the concentration of NIH, whereby it is known that NIH has a fluorescent response to various GST isozymes.
Example 7 detection of GST in human cancer cells by probe NIH
As shown in FIG. 5, the GST-enriched liver cancer cells HepG2, lung cancer cells A549, cervical cancer cells HeLa and negative control cells MHCC97L were incubated with 20. Mu.M NIH for 30min, and observed with a two-photon fluorescence confocal microscope (two-photon infrared excitation wavelength: 810 nm), the fluorescence collecting channels were 500-600nm, and it was confirmed that the GST-containing positive cells all produced strong fluorescence, while the negative control cells were weak in fluorescence, thereby proving that the NIH could detect GST in human cancer cells.
Conclusion: as can be seen from the figures and the examples, the optimized nitrobenzene structure is introduced on the fluorescent parent body with a larger two-photon absorption section as an active center for recognition and reaction with glutathione-S-transferase, and the difference of the fluorescence intensity of the reactant and the product is utilized to realize the two-photon excitation fluorescence detection of the glutathione-S-transferase.
Claims (5)
1. The application of the two-photon fluorescent probe in the process of detecting glutathione-S-transferase in water environment or biological sample is characterized in that: the structure of the fluorescent probe is shown as a general formula I:
in the general formula I, R 1 H, C of a shape of H, C 1 ～C 10 Alkyl of (a); r is R 2 H, C of a shape of H, C 1 ～C 10 One or two of alkyl, halogenated methyl, amino and cyano.
2. The application of the two-photon fluorescent probe in the process of detecting glutathione-S-transferase in water environment or biological sample is characterized in that: the fluorescent probe is one or more than two of compounds NIA, NIB, NIC, NIE, NIF, NIG, NIH, NIL, NIN with the following structures;
3. the use according to claim 1, wherein the compound of formula I is subjected to two-photon excitation with an infrared laser which is completely separated from the emission light band and is transparent to the biological sample for detecting glutathione s-transferase in an aqueous environment outside the organism or in the biological sample, and the compound of formula II is generated after enzymatic action, thereby resulting in a significant increase in fluorescence, which process enables two-photon excitation fluorescence detection of glutathione s-transferase;
general formula II
In the general formula II, R 1 H, C of a shape of H, C 1 ～C 10 Alkyl of R 2 is-OH or-O - 。
4. The use according to claim 2, wherein one or more than two of the compounds NIA, NIB, NIC, NIE, NIF, NIG, NIH, NIL, NIN having the structure are useful for the detection of glutathione s-transferase in a HEPES buffer solution at pH 7.4, which mimics a physiological environment, to produce 4-hydroxy-N-butyl-1, 8 naphthalimide, at pH 7.4, with a portion of the hydroxy groups of the 4-hydroxy-N-butyl-1, 8 naphthalimide being deprotonated;
5. the use according to claim 3, wherein the compound represented by the general formula I and the compound represented by the general formula II have two-photon absorption properties for two-photon excitation fluorescence detection of glutathione-transferase, whereby the glutathione-transferase can be detected under two-photon excitation;
the measurement of glutathione-S-transferase comprises the following steps:
(a) Reacting a compound having the structure of formula I with glutathione s transferase;
(b) The change in fluorescence intensity caused by the reaction in the above step was measured.
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| CN108997326A (en) * | 2018-09-04 | 2018-12-14 | 济南大学 | A kind of mercaptan fluorescence probe and its preparation method and application |
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| An ortho-aldehyde modified probe to image thiols in living cells with enhanced selectivity;Panfei Xing等;《Talanta》;20171121;第179卷;第326-330页 * |
| Naphthalimide-based fluorescent off/on probes for the detection of thiols;Wei Sun等;《Tetrahedron》;20120507;第68卷;第5363-5367页 * |
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