CN104447421A - Preparation and application of novel cysteine and homocysteine fluorescence probe - Google Patents
Preparation and application of novel cysteine and homocysteine fluorescence probe Download PDFInfo
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- CN104447421A CN104447421A CN201410586419.XA CN201410586419A CN104447421A CN 104447421 A CN104447421 A CN 104447421A CN 201410586419 A CN201410586419 A CN 201410586419A CN 104447421 A CN104447421 A CN 104447421A
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- homocysteine
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Abstract
The invention discloses a novel compound capable of being applied to fluorescent recognition of cysteine and homocysteine, particularly relates to a preparation method and an application of a novel fluorescence probe, and belongs to the technical field of chemical analysis detection. The molecular structural formula of the novel fluorescence probe is as shown in the description. The fluorescence probe can be applied to fluorescent sensing analysis of cysteine and homocysteine in an environment or a biological sample, and has good selectivity on the cysteine and the homocysteine, high anti-jamming capability, and a good application prospect; and the cysteine and the homocysteine can be sensitively and rapidly distinguished out from a plurality of amino acids.
Description
Technical field
What the present invention relates to is chemical analysis detection technique field, and the preparation method and this fluorescent probe that are specifically related to a kind of novel cysteine and homocysteine fluorescent probe are detecting the application in sulfite ion.
Background technology
Amino acid is the base substance forming protein, and has close contacting with the vital movement of biology.Halfcystine (Cysteine, and homocysteine (Homocysteine Cys), Hcy) be containing sulfydryl (-SH) and very little two seed amino acids of structure difference, important effect is had in physiological process, medical research shows that they are relevant with a lot of disease, such as renal failure, senile dementia, Parkinson disease, cardiovascular disorder, coronary heart disease, content can as the foundation of these medicals diagnosis on disease in vivo for they.Therefore, people bet very large energy to study rapid sensitive and selectively to detect the technology of halfcystine and homocysteine, the technology applied at present comprises high performance liquid chromatography, capillary electrophoresis, Electrochemical Detection, optical analysis and Mass Spectrometric Identification, these methods can monitor halfcystine and homocysteine in vitro, can not monitoring in viable cell.Fluorescent molecular probe not only highly sensitive selectivity is good, and can in viable cell detect analytes, this technology of fluorescent molecular probe is applied to external or intracellular halfcystine and homocysteine is monitored or cell fluorescence imaging so investigators start to pay close attention to.Report multiple such probe based on chemical reaction, such as Michael addition, aldehyde cyclization and scission reaction at present.In these methods, in fluorescence molecule, fluorescence quenching 2,4-dinitrobenzenes-benzene sulfonate or 2 are introduced, 4-dinitrobenzene sulfuryl amine group, causes quenching of fluorescence, the cracking occurred under halfcystine or homocysteine induction, fluorescence is recovered, and this is a kind of special effective means.Most of water-soluble in this kind of fluorescent probe is poor, can only monitor halfcystine and homocysteine in the mixed solvent of organic solvent or organic solvent and water, its application in biological sample or live body is restricted, and therefore research and development or can need such probe of seldom amount organic solvent be highly significant at the aqueous solution.
Summary of the invention
One of the object of the invention is to provide one and synthesizes simple, gentle, the lower-cost fluorescent probe synthetic method of reaction conditions; Two of object be to provide a kind of highly sensitive, selectivity good, immunity from interference is strong, can to external or intracellular halfcystine and homocysteine is monitored or the fluorescent probe of cell fluorescence imaging.
The present invention's technical scheme taked of dealing with problems is, a kind of catalytic fluorescence method detects the fluorescent probe of halfcystine and homocysteine, and its molecular structural formula is as follows:
synthetic route is as follows:
concrete synthetic method is as follows: (1) is by 2-methoxyl group-6-ethanoyl naphthalene (1.5170g; 7.58mmol) be dissolved in 6mL methylene dichloride; add mass fraction 36% concentrated hydrochloric acid (100mL) again, be heated to 85 DEG C of backflow 4h, stop heating being cooled to room temperature; regulate pH to neutral with 50% sodium hydroxide solution; separate out solid, filtration, filter cake are product, distilled water wash 3 times; vacuum-drying 24h, obtains white solid.Output: 1.3552g.Output: 96%.(2) upper step products therefrom 2-hydroxyl-6-ethanoyl naphthalene (0.0930g, 0.5mmol) is dissolved in 7mL anhydrous methylene chloride, then adds triethylamine (0.1011g; 1mmol); 2,4-dinitrophenyl chloride (0.1333g, 0.5mmol) is dissolved in 3mL anhydrous methylene chloride; slowly be added drop-wise in reaction solution under ice-water bath; continue to stir 1h, stopped reaction, revolves steaming solvent; through column chromatography (eluent, V
methylene dichloride/ V
sherwood oil=1/1) obtain product, vacuum-drying 24h, obtains light yellow solid.Output: 0.0882g.Productive rate: 42.3%.
Fluorescent probe using method of the present invention is as follows, and being dissolved in by probe molecule containing 10% acetonitrile, pH is in the HEPES buffered soln of 7.4, tests under room temperature.And can carry out detection by quantitative to the halfcystine of lower concentration or homocysteine, specific implementation method is introduced in detail in embodiment.
The mechanism of action of fluorescent probe of the present invention is as follows, after probe molecule and halfcystine and homocysteine effect, 2,4-dinitrobenzene benzoyl part is left away from probe molecule, probe molecule becomes very hyperfluorescenceZeng Yongminggaoyingguang from very weak fluorescence, thus achieves the process that catalytic fluorescence method detects halfcystine and homocysteine.The response process of probe molecule:
Fluorescent probe fluorescence emission peak of the present invention is at 495nm place, same with the fluorescence emission peak after halfcystine or homocysteine effect at 495nm place, Fluorescence Increasing 16 times.
Probe molecule synthesis of the present invention is simple, cost is lower, good to the selectivity of halfcystine or homocysteine, immunity from interference strong, fast response time makes this ratio fluorescent probe in biological chemistry, the fields such as environmental science have actual using value.
Accompanying drawing explanation
Fig. 1 is the selectivity of fluorescent probe of the present invention, fluorescent probe (1.0 × 10
-5mol/L) at HEPES buffered soln (20mM, V
acetonitrile/ V
hEPES=1/9, pH=7.4) in, with the fluorescence spectrum after the effect of different sorts amino acid, X-coordinate is wavelength, and ordinate zou is fluorescence intensity.
Fig. 2 is the immunity from interference of half fluorescent probe of the present invention, when halfcystine (Cys) and other amino acid coexist, with fluorescent probe (1.0 × 10
-5mol/L) at buffered soln (20mM, V
acetonitrile/ V
hEPES=1/9, pH=7.4) in effect after fluorescence intensity ratio (I/I
0) histogram.
Fig. 3 is fluorescent probe (1.0 × 10 of the present invention
-5mol/L) at HEPES buffered soln (20mM, V
acetonitrile/ V
hEPES=1/9, pH=7.4) in, change with the fluorescence spectrum after different concns halfcystine (Cys) acts on, X-coordinate is wavelength, and ordinate zou is fluorescence intensity.
Fig. 4 is fluorescent probe (1.0 × 10 of the present invention
-5mol/L) at HEPES buffered soln (20mM, V
acetonitrile/ V
hEPES=1/9, pH=7.4) in, with the linear relationship of halfcystine (Cys) concentration, X-coordinate is wavelength, and ordinate zou is fluorescence intensity.
Fig. 5 is fluorescent probe (1.0 × 10 of the present invention
-5mol/L) at HEPES buffered soln (20mM, V
acetonitrile/ V
hEPES=1/9, pH=7.4) in, change with the fluorescence spectrum after different concns homocysteine (Hcy) acts on, X-coordinate is wavelength, and ordinate zou is fluorescence intensity.
Fig. 6 is fluorescent probe (1.0 × 10 of the present invention
-5mol/L) at HEPES buffered soln (20mM, V
acetonitrile/ V
hEPES=1/9, pH=7.4) in, with the linear relationship of homocysteine (Hcy) concentration, X-coordinate is wavelength, and ordinate zou is fluorescence intensity.
Fig. 7 is fluorescent probe (1.0 × 10 of the present invention
-5mol/L) at buffered soln (V
acetonitrile/ V
hEPES=3/7, pH=7.4) in, over time, X-coordinate is the time with fluorescence intensity in halfcystine (Cys) and homocysteine (Hcy) mechanism, and ordinate zou is fluorescence intensity.
Fig. 8 is fluorescent probe (1.0 × 10 of the present invention
-5mol/L) in different pH value buffered soln, the fluorescence intensity before and after acting on halfcystine (Cys) and homocysteine (Hcy), X-coordinate is pH, and ordinate zou is fluorescence intensity.
Concrete embodiment
The synthesis of embodiment 1:2-compound 2-hydroxyl-6-ethanoyl naphthalene
By 2-methoxyl group-6-ethanoyl naphthalene (1.5170g; 7.58mmol) be dissolved in 6mL methylene dichloride; add mass fraction 36% concentrated hydrochloric acid (100mL) again, be heated to 85 DEG C of backflow 4h, stop heating being cooled to room temperature; regulate pH to neutral with 50% sodium hydroxide solution; separate out solid, filtration, filter cake are product, distilled water wash 3 times; vacuum-drying 24h, obtains white solid.Output: 1.3552g.Output: 96%
Embodiment 2: the synthesis of probe molecule
2-hydroxyl-6-ethanoyl naphthalene (0.0930g, 0.5mmol) is dissolved in 7mL anhydrous methylene chloride, then adds triethylamine (0.1011g; 1mmol); 2,4-dinitrophenyl chloride (0.1333g, 0.5mmol) is dissolved in 3mL anhydrous methylene chloride; slowly be added drop-wise in reaction solution under ice-water bath; continue to stir 1h, stopped reaction, revolves steaming solvent; through column chromatography (eluent, V
methylene dichloride/ V
sherwood oil=1/1) obtain product, vacuum-drying 24h, obtains light yellow solid.Output: 0.0882g.Productive rate: 42.3%.The structural characterization of probe molecule is as follows:
1h NMR (400MHz, DMSO) δ 9.15 (d, J=2.3Hz, 1H), 8.74 (s, 1H), 8.59 (dd, J=8.7,2.3Hz, 1H), 8.26 (dd, J=14.2,8.9Hz, 2H), 8.10-8.00 (m, 2H), 7.90 (d, J=2.4Hz, 1H), 7.43 (dd, J=9.0,2.5Hz, 1H), 2.71 (s, 3H).
13c NMR (126MHz, DMSO) δ 198.17,152.05,148.63,148.27,135.79,135.47,134.12,133.04,131.70,131.22,130.59,129.01,127.99,125.39,121.83,121.63,120.21,27.27.
Embodiment 3: the present invention: the application of fluorescent probe
Probe is dissolved in buffered soln (V
acetonitrile/ V
hEPES=1/9, pH=7.4) in be mixed with 1.0 × 10
-5the solution of mol/L, adds amino acid (Asn, Ala, Val in solution, Phe, His, Leu, Ser, Ile, Trp, Lys, Arg, Pro, Gly, Met, Tyr, Glu, Thr) do not cause the change of fluorescence, add human amino acid (Cys, Hcy) and cause change in fluorescence, this fluorescent probe reveals the identification of highly sensitive, highly selective to halfcystine and homocysteine root table.As halfcystine and homocysteine and interfering substance (Asn, Ala, Val, Phe, His, Leu, Ser, Ile, Trp, Lys, Arg, Pro, Gly, Met, Tyr, Glu, Thr) when coexisting, the impact of the interference-free factor of probe, shows good immunity from interference.This probe molecule and inferior sulfate radical fast response time, namely can be observed the change of fluorescence in 30 seconds.Probe molecule is to inferior sulfate radical Selective recognition, can show wider range of application in the scope of 3 to 10 at pH.
Claims (3)
1. novel cysteine and a homocysteine fluorescent probe, its structure is:
2. the preparation method of halfcystine as claimed in claim 1 and homocysteine fluorescent probe, is characterized in that being prepared according to the following steps:
A 2-methoxyl group-6-ethanoyl naphthalene is dissolved in methylene dichloride by (), add concentrated hydrochloric acid again, be heated to 85 DEG C of backflow 4h, stop heating being cooled to room temperature, regulate pH to neutral with 50% sodium hydroxide solution, separate out solid, filtration, filter cake are product, distilled water wash 3 times, vacuum-drying 24h, obtains intermediate product;
B upper step products therefrom 2-hydroxyl-6-ethanoyl naphthalene is dissolved in anhydrous methylene chloride by (); add triethylamine again, 2,4-dinitrophenyl chloride is dissolved in anhydrous methylene chloride; slowly be added drop-wise in reaction solution under ice-water bath; continue to stir 1h, stopped reaction, revolve and steam except desolventizing; product is obtained through column chromatography for separation; vacuum-drying 24h, obtains light yellow solid, i.e. probe molecule.
3. the purposes of halfcystine according to claim 1 and homocysteine fluorescent probe, is characterized in that this sour fluorescent probe is for the fluoroscopic examination of halfcystine and homocysteine in environment or biological sample and analysis.
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| CN104804729A (en) * | 2015-04-27 | 2015-07-29 | 苏州罗兰生物科技有限公司 | Preparation and application of fluorescence-enhanced sulfite fluorescence probe |
| CN104893710A (en) * | 2015-04-08 | 2015-09-09 | 辽宁大学 | Fluorescence probe, preparation method and application thereof |
| CN105086995A (en) * | 2015-05-21 | 2015-11-25 | 湖南城市学院 | Preparation and application of probe for hydrogen sulfide (H2S) based on protection-deprotection mechanism |
| CN105223171A (en) * | 2015-08-31 | 2016-01-06 | 赣南师范学院 | A kind of synthesis of near infrared phosphorescent iridium complex and fluoroscopic examination imaging applications thereof |
| CN105418662A (en) * | 2015-10-14 | 2016-03-23 | 济南大学 | Preparation and application of cysteine fluorescent probe compound based on BODIPY |
| CN105601658A (en) * | 2016-01-15 | 2016-05-25 | 中南大学 | Application and preparation method of novel fluorescent probe capable of distinguishing biological mercaptans |
| CN105693600A (en) * | 2016-03-24 | 2016-06-22 | 济南大学 | Small-molecule fluorescent probe for identifying cysteine, and preparation method and application for small-molecule fluorescent probe |
| CN105837609A (en) * | 2016-04-01 | 2016-08-10 | 济南大学 | Preparation and application of fluorescent probe capable of rapidly detecting cysteine |
| CN106905199A (en) * | 2017-03-15 | 2017-06-30 | 赣南师范大学 | A kind of synthesis and application of the fluorometric reagent for being used for selective enumeration method cysteine based on aggregation-induced emission principle |
| CN106928133A (en) * | 2017-03-23 | 2017-07-07 | 贺州学院 | A kind of switching mode bivalent cupric ion fluorescence probe and its preparation and application |
| CN106977450A (en) * | 2017-04-28 | 2017-07-25 | 山西大学 | A kind of naphthyl two-photon fluorescence probe and its preparation method and application |
| CN107840838A (en) * | 2017-11-02 | 2018-03-27 | 中南大学 | A kind of fluorescence probe of specific recognition biological thiol |
| CN108794447A (en) * | 2018-06-13 | 2018-11-13 | 天津市环湖医院(天津市神经外科研究所 天津市脑系科中心医院) | One kind is for detecting homocysteine structure fluorescence probe meta-compound and its application |
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| CN109422667A (en) * | 2017-08-23 | 2019-03-05 | 北京工商大学 | A kind of naphthonitrile class hydrogen sulfide fluorescence probe |
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| CN109422669B (en) * | 2017-08-24 | 2021-01-26 | 北京工商大学 | Naphthol hydrogen sulfide fluorescent probe |
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