CN103351335A - Synthesis of fluorescence enhanced fluorescent molecular probe for detecting mercapto-containing amino acids, and application of probe - Google Patents
Synthesis of fluorescence enhanced fluorescent molecular probe for detecting mercapto-containing amino acids, and application of probe Download PDFInfo
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Abstract
The invention relates to a preparation method of a fluorescence enhanced fluorescent molecular probe for detecting mercapto-containing amino acids, and an application of the probe, and concretely relates to a preparation method of a 7-hydroxyquinoline derivative and an application of the 7-hydroxyquinoline derivative in the mercaptoamino acid detection. The fluorescent probe is a pure probe synthesized through directly reacting the 7-hydroxyquinoline derivative with dimethyl sulfate. The largest absorption wavelength of the molecule of the probe is 315nm; and the absorption wavelength of the probe molecule redshifts to 406nm from 315nm with the addition of the mercapto-containing amino acids, the intensity of a fluorescent spectrum at 505nm is continuously enhanced, and very strong green fluorescence is emitted. The probe molecule has the advantages of high detection sensitivity, strong identification capability on the mercapto-containing amino acids, and fast response speed, and has detection limits of Cys, GSH and Hcy mercaptoamino acids being 23nM, 52nM and 5.3nM respectively, and like probes have important application values in the biochemical field and the like.
Description
Technical field
What the present invention relates to is chemical analysis detection technique field, be specifically related to a kind of fluorescence strengthen the preparation method that detects the fluorescent molecular probe that contains mercaptoamino-acid with and contain application aspect the mercaptoamino-acid in detection.
Background technology
The halfcystine (Cys) that contains sulfydryl, homocysteine (Hcy) and reductive glutathione (GSH) are being played the part of important role in many physiological processs.For example, halfcystine (Cys) is considered to be closely related with some diseases, such as senile dementia and Parkinson's disease, and atherosclerotic vascular disease, coronary artery heart disease and renal failure.Reductive glutathione (GSH) is main endogenous antioxidant, is regarded as the indicator of oxidative stress ability, and sulfhydryl content also may be subject to the impact of some response to oxidative stress in the organism.Simultaneously, the activity that the mercaptan that utilizes sulfydryl probe identification organism to discharge can be used for indirect detection associated biomolecule enzyme and estimate corresponding inhibitor.Therefore, seek method quick, sensitive, selectivity detection of biological sulfydryl and more and more be subject to people's attention (Giles NM., Watts AB, Giles GI, Fry FH, Littlechild JA, Jacob C.Metal and redox modulation of cysteine protein function.[J] Chemistry﹠amp; Biology2003; 10 (8): 677-693.Wang W, Rusin O, Xu X, Kim KK, Escobedo JO, Fakayode SO, Fletcher KA, Lowry M, Schowalter CM, Lawrence CM, Fronczek FR, Warner IM, Strongin RM.Detection of homocysteine and cysteine.[J] Journal of the American Chemical Society2005; 127 (45): 15949-15958.Seshadri S, Beiser A, Selhub J, Jacques PF, Rosenberg IH, D ' Agostino RB, Wilson PW, Wolf PA.Plasma homocysteine as a risk factor for dementia and Alzheimer ' s disease.[J] New England Journal of Medicine2002; 346 (7): 476-483.).
At present, reported that some analytical procedures detect, mainly comprise high performance liquid chromatography (HPLC), electrochemical method, capillary electrophoresis, light analysis and mass-spectrometric technique are to seek to halfcystine (Cys) the efficient and rapid detection of homocysteine (Hcy) and reductive glutathione (GSH).But these methods all are to limit the use of in the in vitro experiment, are difficult to be applied to detect halfcystine (Cys) in active somatic cell, homocysteine (Hcy) and reductive glutathione (GSH).Permeates cell membranes can single-mindedly imaging in active somatic cell effectively thereby fluorescent probe is as the small molecule material, has preferably susceptibility.Therefore, some fluorescent probes based on chemical reaction type are in the news, thereby these probes mainly are to utilize annulation that Michael addition reaction and aldehyde radical effect cause and scission reaction etc. to finish chemical conversion to realize fluorescent probe to halfcystine (Cys), the detection of homocysteine (Hcy) and reductive glutathione (GSH).(Zhu?J，Dhimitruka?I，Pei?D.5-(2-Aminoethyl)dithio-2-nitrobenzoate?as?a?more?base-stable?alternative?to?Ellman′s?reagent.[J]?Organic?Letters2004；6(21)：3809-3812.Hu?M，Fan?J，Li?H，Song?K，Wang?S，Cheng?G，Peng?X.Fluorescent?chemodosimeter?for?Cys/Hcy?with?a?large?absorption?shift?and?imaging?in?living?cells.[J]Organic?Biomolecular?Chemistry2011；9(4)：980-983.Long?L，Lin?W，Chen?B，Gao?W，Yuan?L.Construction?of?a?FRET-based?ratiometric?fluorescent?thiol?probe.[J]Chemical?Communications2011；47(3)：893-895.)。
The fluorescent probe great majority of report are to halfcystine (Cys) at present, and the response of homocysteine (Hcy) and reductive glutathione (GSH) is based on the change of fluorescence intensity, and most of fluorescent probe just has good performance in the extracellular.Therefore, develop a kind of fluorescent probe that has colour-change and fluorescence enhancing concurrently to inquiring into halfcystine (Cys), the biological action of homocysteine (Hcy) and reductive glutathione (GSH) has very important significance.
Summary of the invention
One of purpose of the present invention provide a kind of synthetic easy, reaction conditions is gentle, lower-cost fluorescent probe synthetic method; It is good that two of purpose provides a kind of selectivity, highly sensitive, strengthens to detect halfcystine (Cys) based on fluorescence, the fluorescent probe of homocysteine (Hcy) and reductive glutathione (GSH).
The fluorescence that the present invention uses strengthens detection halfcystine (Cys), the fluorescent molecular probe of homocysteine (Hcy) and reductive glutathione (GSH), adopt under 7-hydroxyquinoline ester and the condition of methyl-sulfate take methylene dichloride as solvent synthetic, 2,4-dinitrobenzene sulfonic acid ester is as recognition group.
The present invention's technical scheme of taking of dealing with problems is, a kind of fluorescence strengthens and detects halfcystine (Cys), and homocysteine (Hcy) and reductive glutathione (GSH) fluorescent molecular probe have following structural:
The composition principle of the representational compound of the present invention, its synthetic route is shown below: (1) is dissolved in 7-hydroxyquinoline and 2,4-dinitrophenyl chloride in the anhydrous methylene chloride, does alkali with triethylamine.Stirred 12 hours under the room temperature condition, get straight product 2 take methylene dichloride as eluent through column chromatography again, 4-dinitrobenzene sulfonic acid-7-hydroxyquinoline ester.(2) 2,4-dinitrobenzene sulfonic acid-7-hydroxyquinoline ester and methyl-sulfate are dissolved in the anhydrous methylene chloride reaction after five days, (volume ratio is l: 1) recrystallization gets the probe sterling with the mixed solvent of methylene dichloride and methyl alcohol behind the suction filtration.
In the embodiment of this specification sheets, understand in more detail the synthetic and detection method of this probe.Fluorescent molecular probe using method of the present invention does not have particular restriction.Usually probe molecule can be dissolved in the dimethyl sulfoxide (DMSO), then at room temperature test.When adding contains mercaptoamino-acid and polypeptide, because mercapto groups can be with 2, phenyl ring generation nucleophilic substitution reaction (seeing following formula) in the 4-dinitrobenzene sulfonic acid, interrupted the fluorescent quenching effect of nitro to probe compound, so that Photoinduced Electron transferance (PET) is suppressed, thereby so that the fluorescence of probe strengthens, solution colour changes simultaneously, and ultraviolet and fluorescence spectrum produce significantly and change.
The specific features of the amino acid fluorescent molecular probe of open hole detection of the present invention and fluorescence enhancing detection sulfydryl is as follows:
The maximum absorption wavelength of this fluorescence probe in dimethyl sulphoxide solution is 315nm, almost do not observe fluorescent signal; Probe solvability in the mixed solvent of dimethyl sulfoxide (DMSO)/PBS (pH=7.4) is better, and along with the adding that contains mercaptoamino-acid and polypeptide, probe molecule descends gradually in the maximum absorption at 315nm place, and solution sends green fluorescence; In fluorescence spectrum, maximum emission peak appears in the 505nm place, and along with the increase that contains mercaptoamino-acid and polypeptide, its fluorescence intensity also increases thereupon, and maximum can strengthen 130 times.Under the irradiation of ultraviolet lamp, probe presents stronger green fluorescence.
Probe molecule sensitivity of the present invention is higher, optical property is stable, and raw material is easy to get, and synthetic yield is higher, to containing mercaptoamino-acid and the polypeptide recognition capability is strong, fast response time, detectability is respectively 23nM, 52nM and 5.3nM (Cys, GSH and Hcy), sensing range is wide, detects lower limit low, so the type probe has actual using value in fields such as biological chemistry, environmental sciences.
Description of drawings
Fig. 1 is ultra-violet absorption spectrum changing conditions before and after the adding Cys of fluorescent probe of the present invention in 20mM PBS (pH=7.4) water solution system, and X-coordinate is wavelength, and ordinate zou is absorbancy.
Fig. 2 be fluorescent probe of the present invention in 20mM PBS (pH=7.4) water solution system, the changing conditions that fluorescence emission spectrum increases with Cys concentration, X-coordinate is wavelength, ordinate zou is fluorescence intensity, excitation wavelength is 405nm.
Fig. 3 be fluorescent probe of the present invention in 20mM PBS (pH=7.4) water solution system, the changing conditions that fluorescence intensity increases with Hcy, X-coordinate is the concentration of Hcy, ordinate zou is fluorescence intensity, excitation wavelength is 405nm.
Fig. 4 be fluorescent probe of the present invention in 20mM PBS (pH=7.4) water solution system, the changing conditions that fluorescence intensity increases with GSH concentration, X-coordinate is the concentration of GSH, ordinate zou is fluorescence intensity, excitation wavelength is 405nm.
Fig. 5 is that fluorescent probe of the present invention is in 20mM PBS (pH=7.4) water solution system, fluorescence intensity is with adding the different testers of isoconcentration: halfcystine (Cys), aspartic acid (Asp), L-Ala (Ala), α-amino-isovaleric acid (Val), phenylalanine (Phe), Histidine (His), Isoleucine (Ile), Methionin (Lys), arginine (Arg), proline(Pro) (Pro), glycine (Gly), methionine(Met) (Met),, aspartic acid (Asn), L-glutamic acid (Glu), Threonine (Thr), X-coordinate is the amino acid title, and ordinate zou is fluorescence intensity, and excitation wavelength is 405nm.
Fig. 6 be fluorescent probe of the present invention in 20mM PBS (pH=7.4) water solution system, fluorescent probe adds before and after the Cys, fluorescence emission spectrum is with the changing conditions of different pH, X-coordinate is pH, ordinate zou is fluorescence intensity, excitation wavelength is 405nm.
Fig. 7 is the proton nmr spectra of the fluorescence probe that synthesizes of the present invention.
Embodiment
Embodiment 1:2, the preparation of 4-dinitrobenzene sulfonic acid-7-hydroxyquinoline ester
Get 7-hydroxyquinoline (145mg, 1mmol) and 2,4-dinitrophenyl chloride (267mg, 1mmol) be dissolved in the anhydrous methylene chloride, drip again triethylamine (150mg, 1.5mmol), stirred 12 hours under the room temperature, after reaction finished, methylene dichloride was removed in distillation, take methylene dichloride as eluent, get 2 through column chromatography, 4-dinitrobenzene sulfonic acid 7-hydroxyquinoline ester, 273mg, productive rate are 73%.
Embodiment 2: the preparation of fluorescence probe
Get 2,4-dinitrobenzene sulfonic acid 7-hydroxyquinoline ester (75mg, 0.2mmol) and be dissolved in the 15mL anhydrous methylene chloride with methyl-sulfate (252mg, 2mmol), stirring at room 5 days produces a large amount of white precipitates.Suction filtration gets white solid, uses methylene dichloride: get white solid fluorescent probe 30mg behind the mixed solvent recrystallization of methyl alcohol=1: 1 (volume ratio), productive rate is 30%.1HNMR(301MHz，DMSO)：δ
ppm＝9.57(d，J＝5.8Hz，1H)，9.33(d，J＝8.3Hz，1H)，9.17(d，J＝2.3Hz，1H)，8.65(dd，J＝8.7，2.3Hz，1H)，8.60(d，J＝9.1Hz，1H)，8.45(d，J＝2.1Hz，1H)，8.40(d，J＝8.7Hz，1H)，8.24(dd，J＝8.4，5.8Hz，1H)，7.90(dd，J＝9.0，2.2Hz，1H)，4.55(s，3H)，3.36(s，3H)，2.50(dt，J＝3.6，1.8Hz，3H).
Embodiment 3: bore hole and fluorescence strengthen the application that detection contains the mercaptoamino-acid fluorescent probe
This probe is dissolved in DMSO/PBS (pH=7.4) buffered soln, tests its ultra-violet absorption spectrum and fluorescence spectrum and change.Fig. 1～Fig. 5 shows, has very high selectivity in UV spectrum and fluorescence spectrum middle probe to containing mercaptoamino-acid, its UV spectrum of increase and the fluorescence spectrum that contain the sulfhydryl amino acid concentration along with adding obviously change, and significant colour-change occurs solution colour, is applicable to open hole detection; Simultaneously, after adding mercaptoamino-acid, fluorescence intensity strengthens 130 times, and probe is not subjected to some other amino acid whose impact, for example: halfcystine (Cys), aspartic acid (Asp), L-Ala (Ala), α-amino-isovaleric acid (Val), phenylalanine (Phe), Histidine (His), Isoleucine (Ile), Methionin (Lys), arginine (Arg), proline(Pro) (Pro), glycine (Gly), methionine(Met) (Met), aspartic acid (Asn), L-glutamic acid (Glu), Threonine (Thr); Even under the condition that interfering ion exists, probe also has good response to containing mercaptoamino-acid.
Claims (6)
1. the present invention relates to a kind of fluorescence strengthen detect the preparation method that contains the mercaptoamino-acid fluorescent molecular probe with and contain application aspect the mercaptoamino-acid in detection, it is characterized in that having following chemical molecular structural formula:
Described detection contains the fluorescent probe of mercaptoamino-acid take the 7-quinolinol derivative as fluorophore, and 2,4-dinitrobenzene sulfonic acid ester is the compound of sulfydryl recognition group.
2. the synthetic method of fluorescent molecular probe claimed in claim 1, its preparation method is:
1) 7-hydroxyquinoline and 2,4-dinitrophenyl chloride are dissolved in the anhydrous methylene chloride, triethylamine at room temperature stirred 12 hours as alkali, then got straight product 2 take methylene dichloride as eluent through column chromatography, 4-dinitrobenzene sulfonic acid 7-hydroxyquinoline ester.
2) 2,4-dinitrobenzene sulfonic acid 7-hydroxyquinoline ester and methyl-sulfate are dissolved in the anhydrous methylene chloride, stirring at room is after 5 days, and solid methylene dichloride behind the suction filtration: the mixed solvent recrystallization of methyl alcohol=1: 1 (volume ratio) gets white solid.
3. the fluorescence based on the 7-quinolinol derivative according to claim 2 strengthens the fluorescent molecular probe synthetic method that detection contains mercaptoamino-acid, and it is characterized in that: the solvent that adopts described reactions steps 1) comprises methylene dichloride, trichloromethane etc.
4. the fluorescence based on the 7-quinolinol derivative according to claim 2 strengthens and detects the fluorescent molecular probe synthetic method that contains mercaptoamino-acid, it is characterized in that described reactions steps 1) in the organic bases that adopts be a kind of in triethylamine, pyridine, the piperidines etc.
5. the fluorescence based on the 7-quinolinol derivative according to claim 2 strengthens and detects the fluorescent molecular probe synthetic method that contains mercaptoamino-acid, it is characterized in that described reactions steps 2) in adopt solvent can be the organic solvents such as methylene dichloride, trichloromethane, tetrahydrofuran (THF).
6. the application of fluorescent molecular probe claimed in claim 1 is used for fluorescence and strengthens the detection mercaptoamino-acid.
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