CN104119263A - Cyanin-based organic compound and application thereof - Google Patents

Cyanin-based organic compound and application thereof Download PDF

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CN104119263A
CN104119263A CN201410294697.8A CN201410294697A CN104119263A CN 104119263 A CN104119263 A CN 104119263A CN 201410294697 A CN201410294697 A CN 201410294697A CN 104119263 A CN104119263 A CN 104119263A
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cysteine
compound
halfcystine
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probe
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CN104119263B (en
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陈令新
殷堃
于法标
张卫卫
陈浩
刘萍
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Yantai Institute of Coastal Zone Research of CAS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/107—The polymethine chain containing an even number of >CH- groups four >CH- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

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  • Organic Chemistry (AREA)
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  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
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Abstract

The invention relates to a fluorescence probe, and particularly relates to a cyanin-based organic compound and an application thereof. A structural formula of the cyanin-based organic compound is as shown in the formula I in the specification. According to the compound serving as a cysteine fluorescent probe, the corresponding fluorescence intensity obviously changes under the existence of cysteine, the compound can be applied to cysteine detection, the interference of an external detection condition can be greatly reduced, and the detection accuracy is improved. According to the compound serving as the cysteine fluorescent probe, ultraviolet absorption obviously changes under the existence of cysteine, and the compound serving as the cysteine fluorescent probe can be simultaneously used for detection by using an ultraviolet spectrophotometer and naked eyes. The compound can be applied to detection of cysteine levels inside and outside a cell as the fluorescent probe, and the compound has important biomedical significance on intensive study of dynamics mechanism of the processes of cysteine generation, transportation and accumulation inside a living body, particularly study of physiological action of cysteine in mitochondria.

Description

A kind of organic compound and application thereof based on cyanine
Technical field
The present invention relates to fluorescent probe, specifically a kind of organic compound and application thereof based on cyanine.
Background technology
Halfcystine is a kind of amino acid containing sulfydryl, is one of important physiologically active substance.It can increase the growing amount of gsh as the substrate of reductive glutathione, thereby the stability of Cell protection film alleviates the damage of myocardial cell in ischemic reperfusion.Cys participates in the reduction of cell and the phospholipid metabolism process in liver, has the effect of protection liver cell, promotion liver function.In addition, Cys stimulates in addition pre-T lymphocyte to be divided into ripe lymphocytic effect and increases the resistibility of human body to some toxin.In organism, content and the Metabolic disorder of halfcystine all can cause the generation of some diseases, by measuring the content of halfcystine in organism, can realize the diagnosis to some metabolic trouble.Therefore, realizing quick, sensitive detection halfcystine tool is of great significance.
At present, picture colorimetry, electrochemical analysis, the methods such as stratographic analysis all can be used to measure the semicystinol concentration in blood plasma and homogenate tissue, but these methods often need sample pretreatment, fluorescent probe detection method because of its have highly sensitive and can direct-detection in viable cell or tissue etc. advantage become one of important detection means of analyzing halfcystine in life entity.A fluorescent probe with application prospect should have that change in fluorescence obviously before and after effect, fast to target molecule response, selectivity is good, can be used for the advantages such as real-time reversible detection.Meng Zhang etc. discloses a class in order to detect the fluorescent probe (structure is shown in Fig. 1, M.Zhang et.al, J.Am.Chem.Soc., 2007,129,10322) of halfcystine, thus with halfcystine effect after fluorescence strengthen to detect the existence of halfcystine.But this class fluorescent probe, to halfcystine low-response, detects limit for height, can not be for detecting rapidly halfcystine.And the excitation-emission wavelength of this probe is positioned at ultraviolet region, can not effectively avoid the interference of biological autofluorescence, UV-light is very large to organism photobleaching simultaneously, is easy to damage biological sample.For reaching, be fully penetrated into organization internal and avoid cell autofluorescence to disturb object, greatly reduce the interference of outside atmosphere, realize detection by quantitative, still need exploitation to there is the operability fluorescent probe of longer excitation-emission wavelength.Therefore, exploitation has good selectivity, and the fluorescent probe that can carry out in near-infrared region halfcystine in detection of biological system is significant.
Summary of the invention
The object of the present invention is to provide a kind of organic compound and application thereof based on cyanine.
For achieving the above object, the technical solution used in the present invention is:
An organic compound based on cyanine, the organic compound based on cyanine, structural formula is suc as formula shown in I,
An application for organic compound based on cyanine, the organic compound based on cyanine shown in described formula I is as the fluorescent probe that detects halfcystine.
The organic compound based on cyanine shown in described formula I as probe for the halfcystine under the detection physiological environment of qualitative/quantitative, inside and outside cell or organism.
Beneficial effect of the present invention:
The present invention is for the compound as halfcystine fluorescent probe, its corresponding fluorescence intensity and emission wavelength under halfcystine exists changes, while uv-absorbing also correspondence changes, and then the detection that can be used for aqueous systems, simulates physiological environment and intracellular cysteine level, and can greatly reduce the interference of external detection condition, improve accuracy of detection.The compounds of this invention is as fluorescent probe, can be used for the detection of intracellular cysteine, but also can position intracellular plastosome, this kinetics mechanism to the further investigation halfcystine processes such as generation, conveying and accumulation in vivo, further understand the physiological action of halfcystine, especially study halfcystine and there is important biomedical meaning at plastosome antagonism oxidative stress environment role.
The present invention is for the compound as halfcystine fluorescent probe, and corresponding fluorescence intensity generation considerable change under halfcystine exists, can be used for the detection of halfcystine, and can greatly reduce the interference of external detection condition, improves accuracy of detection.This compounds of this invention halfcystine fluorescent probe, also there is considerable change in uv-absorbing when halfcystine exists, and can with ultraviolet scene luminosity, take into account naked eyes simultaneously and detect.This compounds can be used for the detection of cysteine levels inside and outside cell as fluorescent probe, this kinetics mechanism to the further investigation halfcystine processes such as generation, conveying and accumulation in vivo, especially studies halfcystine and has important biomedical meaning in plastosome physiological action.
Accompanying drawing explanation
The fluorescence intensity change curve of the fluorescent probe adopting under the different pH that Fig. 1 provides for the embodiment of the present invention.
After the fluorescent probe adopting under the different pH that Fig. 2 provides for the embodiment of the present invention and halfcystine effect at 560nm and 720nm place fluorescence intensity ratio value change curve.
The selectivity schematic diagram of the fluorescent probe adopting that Fig. 3 provides for the embodiment of the present invention to halfcystine; Wherein, X-coordinate is followed successively by blank, halfcystine, homocysteine, gsh, tryptophane, glycine, Threonine, proline(Pro), arginine, Serine, methionine(Met), α-amino-isovaleric acid from left to right.
The linear fit curve that the fluorescent probe 560nm adopting that Fig. 4 provides for the embodiment of the present invention and 720nm place fluorescence intensity ratio value and semicystinol concentration change.
The employing fluorescent probe halfcystine that Fig. 5 provides for the embodiment of the present invention is for detection of the Laser Scanning Confocal Microscope imaging of hydrogen sulfide in cell.
Embodiment
Embodiment is used for further illustrating the present invention, but the invention is not restricted to embodiment.
Embodiment 1
Organic compound structure formula based on cyanine is:
Halfcystine during formula I compound is inside and outside with water body to be determined, simulation physiological environment or organism is combined, thereby the compound that obtains structural formula II structure causes the fluorescence intensity of formula I compound and the change of wavelength, and the change of uv-absorbing, and then utilize formula I compound to carry out qualitative, quantitative detection to halfcystine.
The preparation of the formula I organic compound based on cyanine:
(1) preparation of compound one
Graduated cylinder measures 20-50mL DMF and is dissolved in 20-40mL methylene dichloride, pours into (putting magneton stirs) in 250mL there-necked flask, cooling in ice-water bath.Measure 20-40mL phosphorus oxychloride and dissolve in 20-40mL methylene dichloride, pour in constant pressure funnel and be added dropwise in above-mentioned cooling rear solution, and with magnetic, stir instrument and constantly stir.
Dropwise, take 5-10g pimelinketone and pour above-mentioned constant pressure funnel dropping into.Now solution colour gradually becomes yellow by colourless.Then remove ice-water bath, reflux 3 hours.After reaction finishes, reaction solution is poured into and filled in trash ice.Be placed in stink cupboard standing over night.In tank, upper strata is that yellow liquid bottom is yellow flocks and has a little red oil.Use Büchner funnel decompress filter, mother liquor washing, obtains yellow solid compound one.Solid transfer is in small beaker, dry in vacuum drying oven.Fusing point: 130～131 ℃, results of elemental analyses (theoretical value): C, 55.4 (55.7); H5.4 (5.3); Cl, 20.4 (20.5).LC-MS(API-ES):m/z?C 8H 9ClO 2Calcd172,found[M +]173.
(2) preparation of compound two
By 100-150mL iodoethane, 20-30mL2,3,3-tri-methyl indole quinoline, 10-20mL toluene three adds in 250mL round-bottomed flask, reflux 10-15h reaction.After complete, on Rotary Evaporators, solvent is spin-dried for, after being spin-dried for, obtains amaranth solid.Toward adding methyl alcohol heating in flask, make after dissolution of solid, transfer to and in beaker, drip ether solid precipitation is gone out.Suction filtration, uses ether washing precipitation, obtains baby pink pulverulent solids compound two.Stand-by by transferring to after solid drying in wide-necked bottle.Results of elemental analyses (theoretical value): C, 82.9 (82.8); H9.7 (9.8); N, 7.4 (7.5).LC-MS(API-ES):m/z?C 13H 18N +Calcd188,found[M +]189.
(3) preparation of compound three
0.5-1g compound one and 0.2-0.5g compound two are dissolved in the mixed solvent of 100-150mL propyl carbinol and benzene (7:3v/v), fill a water separator on reactor, separate the water that reaction generates, and reaction can be carried out to positive reaction direction.Mixture reflux, and constantly stir.After reaction 2-4h, cool to room temperature, underpressure distillation is except desolventizing.Precipitation is washed with ether, obtains amaranth solid crude product, column chromatography separating purification, and eluent is methyl alcohol-ethyl acetate (7:12V/V), obtains green product compound three.Results of elemental analyses (theoretical value): C, 79.7 (79.8); H, 7.9 (8.0); Cl, 6.9 (6.8); N, 5.5 (5.6).LC-MS(API-ES):m/z?C 34H 40ClN 2 +Calcd511,found[M +]512.
(4) preparation of compound four
Under nitrogen protection, 0.3-0.5g compound three and 0.1-0.3g sodium-acetate react 5-8 hour in the anhydrous DMF of 10-20ml at 80-90 ℃.After cooling, with quartz sand termination reaction filtration.Silica gel column chromatogram separating purification, eluent is methyl alcohol-ethyl acetate (7:12V/V), receives red component, obtains red product, is compound four.
Results of elemental analyses (theoretical value): C, 88.9 (88.8); H, 8.2 (8.3); N, 5.7 (5.8); O, 3.2 (3.3).LC-MS(API-ES):m/z?C 34H 40N 2O?Calcd492,found[M +]493.
(5) preparation of formula one
By 0.2-0.5g compound four, 0.1-0.3g paranitrobenzoyl chloride and the anhydrous quadrol of 150-200 μ L react 0.5-2h in the anhydrous DMF of 20-30ml under condition of ice bath.Silica gel column chromatogram separating purification, eluent is methyl alcohol-ethyl acetate (1:3V/V), receives green color component, obtains green product formula one compound.Results of elemental analyses (theoretical value): C, 76.6 (76.7); H, 6.9 (6.8); N, 6.5 (6.6); O, 9.9 (10.0).LC-MS(API-ES):m/z?C 41H 44N 3O 4 +Calcd642,found[M +]643.
Embodiment 2
Using preparing gained formula one compound, as probe application in aqueous systems, in simulation physiological environment and cell, carry out the detection to halfcystine, simulation physiological condition, (HEPES buffered soln is all carried out in the following experiment under pH7-8 condition, concentration is 1-30mM), concentration and probe concentration adopts 0.5-10 μ M.
The above-mentioned pH effect of gained probe to the response of semicanal propylhomoserin of preparing:
PH gradient adopts HEPES buffered soln to control.In 1.5ml colorimetric cylinder, add the 1-10mM HEPES of the different pH gradients of 0.8-1mL, then add 1-10 μ L100 μ M probe, shake up solution, after balance 10-30min, above-mentioned mixed working fluid is added in fluorescence ware and measures fluorescence spectrum at 25-40 ℃.Fluorescence intensity with the variation of pH as shown in Figure 1.In the scope of pH4.0～8.0, fluorescence intensity does not have considerable change as shown in Figure 1, and, in the system of pH6.0～8.0, probe is all stable, may be used to detect halfcystine.In 1.5ml colorimetric cylinder, add 0.8-1mL1-10mM HEPES, add again 1-10 μ L 100 μ M probes, then add 50-100 μ L 200 μ M halfcystines, shake up solution, at 25-40 ℃, after balance 10-30min, above-mentioned working fluid is added in fluorescence ware and measures fluorescence spectrum.Ratio fluorescent with the variation of pH as shown in Figure 2.Can find the system in pH6.0～8.0, probe halfcystine has corresponding, and with the rising of pH, corresponding reinforcement, because probe is under alkaline condition, relatively unstable, so, at pH, be 7.40 o'clock, probe is both stable, can, to the sensitive response of semicanal propylhomoserin, can be used for realizing the detection in organism again.
Embodiment 3
The selectivity of probe to halfcystine
PH adopts HEPES buffered soln to control.Get a plurality of 1.5ml colorimetric cylinders, in colorimetric cylinder, add 0.9-1mL1-10mM HEPES, pH7-8, add 1-10 μ L 100 μ M probes again, then add respectively determinand as shown in Figure 2, determinand working fluid is followed successively by: blank (without amino acid), halfcystine, homocysteine, gsh, tryptophane, glycine, Threonine, proline(Pro), arginine, Serine, methionine(Met), α-amino-isovaleric acid, wherein the final concentration of halfcystine and homocysteine is 20 μ M, and other final concentrations are 2mM.Shake up solution, after balance 10-30min, working fluid in each colorimetric cylinder is poured into respectively in fluorescence ware and measures fluorescence spectrum at 25-40 ℃.Probe to the selectivity of halfcystine as shown in Figure 2.And probe has good selectivity to halfcystine as seen from the figure, after halfcystine effect, the fluorescence that 720nM place excites obviously weakens, and the fluorescence that 560nM place excites obviously strengthens.Homocysteine under condition determination, gsh, tryptophane, glycine, Threonine, proline(Pro), arginine, Serine, methionine(Met), α-amino-isovaleric acids etc. can not make fluorescence probe change.
Embodiment 4
The detection by quantitative of probe to halfcystine
Get a plurality of 1.5ml colorimetric cylinders, in each colorimetric cylinder, add 0.9-1mL1-10mMHEPES, pH7-8, add again 1-10 μ L100 μ M probe, then add respectively the halfcystine of different final concentrations, final concentration is respectively 2, 4, 6, 8, 10, 12 μ M, shake up solution, at 25-40 ℃ after balance 10-30min, pour respectively the working fluid in each colorimetric cylinder into fluorescence ware and measure fluorescence spectrum, get each 560nm and 720nm place fluorescence intensity ratio value, Input Software OriginPro8.0, obtain linear work curve as shown in Figure 4, wherein the linear regression constant of linear fit curve is 0.996, the concentration that shows the mensuration halfcystine that probe can be quantitative.
By Fig. 3, represented, with the variation of the variation system fluorescence intensity of semicystinol concentration, to show the increase with semicystinol concentration, system 560nm absorption intensity is in obvious enhancing, and 720nm absorption intensity is obviously weakening.
Embodiment 5
The detection by quantitative of probe to halfcystine in artificial cerebrospinal fluid
Get a plurality of 1.5ml colorimetric cylinders, in each colorimetric cylinder, add 0.9-1mL1-10mM artificial cerebrospinal fluid, pH7-8, add again 1-10 μ L100 μ M probe, then adding respectively final concentration is 2, 4, 6, 8, 10 μ M halfcystines, shake up solution, at 25-40 ℃ after balance 10-30min, pour respectively the working fluid in each colorimetric cylinder into fluorescence ware and measure fluorescence spectrum, obtain each 560nm and 720nm place fluorescence intensity ratio value, and institute's value is compared with numerical value in resulting linear work curve in embodiment 7, find repeatability better (referring to table 1), the concentration that shows the mensuration halfcystine that probe can be quantitative in cerebrospinal fluid.
Table 1 is with fluorescent probe, to detect the result of halfcystine in cerebrospinal fluid
Embodiment 6
Probe is for the detection of hydrogen sulfide in cell
It is 50% left and right that murine hepatocarcinoma cell HepG2 is cultured to cell density according to American type Tissue Culture Collection regulation.Then by HepG2 cell in 1-10 μ M probe 25-40 ℃ hatch 10-30 minute, with DMEM-1640 substratum washing 3 times, be placed under confocal fluorescent microscope, under 560nM exciting light, take pictures (referring to Fig. 5).As shown in Figure 5, under 560nM exciting light, fluorescence intensity obviously strengthens; This probe mainly dyes to cell mitochondrial.
Above content is in conjunction with concrete preferred implementation further description made for the present invention, can not assert that specific embodiment of the invention is confined to these explanations.For general technical staff of the technical field of the invention, without departing from the inventive concept of the premise, can also make some simple deduction or replace, all should be considered as belonging to protection scope of the present invention.It as fluorescence dye, is a kind of purposes of new compound of the present invention; can not assert that compound of the present invention is only for fluorescence dye; for general technical staff of the technical field of the invention; under the consideration as the same function mechanism of fluorescence dye based on the compounds of this invention; can also make some simple inferences; draw other application purpose of compound of the present invention, all should be considered as belonging to protection scope of the present invention.

Claims (3)

1. the organic compound based on cyanine, is characterized in that: the organic compound based on cyanine, and structural formula is suc as formula shown in I,
2. an application for the organic compound based on cyanine claimed in claim 1, is characterized in that: the organic compound based on cyanine shown in described formula I is as the fluorescent probe that detects halfcystine.
3. by the application of the organic compound based on cyanine claimed in claim 2, it is characterized in that: the organic compound based on cyanine shown in described formula I as probe for the halfcystine under the detection physiological environment of qualitative/quantitative, inside and outside cell or organism.
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CN112062708A (en) * 2020-09-27 2020-12-11 中国科学院烟台海岸带研究所 Fluorescent probe compound for detecting cysteine and application thereof
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