CN105001856A - Fluorescent probe for monitoring lipid peroxidation processes in different subcellular organelles - Google Patents
Fluorescent probe for monitoring lipid peroxidation processes in different subcellular organelles Download PDFInfo
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- CN105001856A CN105001856A CN201510411234.XA CN201510411234A CN105001856A CN 105001856 A CN105001856 A CN 105001856A CN 201510411234 A CN201510411234 A CN 201510411234A CN 105001856 A CN105001856 A CN 105001856A
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- fluorescent probe
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- lipid peroxidation
- fluorine boron
- pyrrole derivative
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Abstract
The invention discloses a fluorescent probe for monitoring lipid peroxidation processes in different subcellular organelles, and belongs to the field of fine chemical engineering. The fluorescent probe is prepared through the steps of: enabling fluorine boron pyrrole derivatives to react with cinnamic aldehyde, wherein piperidine is used as a catalyst, and a 4 angstrom molecular sieve is used as a dehydrating agent; and performing quaternization on the obtained reactant so as to obtain molecules of the fluorescent probe. The probe contains active groups such as triphenylphosphine cations, morpholine and quaternary ammonium salt cations, the probe has a single-minded subcellular organelle targeting property because of the different active groups, and the probe can be optionally positioned on subcellular organelles such as mitochondria, lysosomes and cell membranes. The probe has zero toxin and zero side effects and is suitable for monitoring the lipid peroxidation processes in the subcellular organelles in different physiological processes through a fluorescent microscope or flow type cell analyzing technology. The probe is stable in solid condition nature and easy to store for a long time, an intuitional succinct detecting reagent with low cost is provided for inquiring processes relevant to the lipid peroxidation in cells, and microcosmic structural information is provided for detection by a subcellular organelle targeting property function.
Description
Technical field
The present invention relates to a class for monitoring the fluorescent probe of lipid peroxidation process in different subcellular organelle, it belongs to technical field of fine.
Background technology
Lipid peroxidation (Lipid peroxidation, LPO) is the main pathogenesis of numerous disease by clear and definite report, as cancer, and atherosclerosis, nervous system disorders, etc.The essence of LPO is the chain reaction of the type free base based on unsaturated fatty acids, it is normally by active oxygen radical (reactive oxygen species, ROS) cause, and it often exceeds the Oxidative demage of ROS to intercellular membrane structure to the pathogenic damage of body.LPO to the pernicious result that body brings come from chain reaction continue carry out, chain reaction can continuous release of active agent, and as mda, this type of material can cause multiple destructive reaction, and damage body is active.Therefore, the LPO process in postgraduate's object for the prevention of specified disease or previous tretament significant.
Fluorescence microscopy is suitable for the dynamic monitoring that can't harm viable cell as a kind of intuitively real-time monitoring means.Although existing part report utilizes fluorescence imaging means to monitor the generation of LPO, but the LPO probe with subcellular organelle targeting reported is little, mainly based on commercialization LPO probe C11-BODIPY
581/591, and its synthesis and preparation process is more loaded down with trivial details, causes its cost higher, expensive, is unfavorable for widely using, and only has a routine target mitochondrial LPO probe MitoPerOx to be also based on C11-BODIPY
581/591the structure of carrying out derives, and synthesis is complicated.LPO probe for other subcellular organelle targetings more there is no report.According to the demand of research associated conditions, we are devoted to design the LPO probe with different subcellular organelle targeting, and the Clinics and Practices for LPO relative disease provides information and the research tool of more microcosmic.
Summary of the invention
In order to solve the problems of the technologies described above, the invention provides and a series ofly can detect fluorescent probe of wherein lipid peroxidation process and preparation method thereof for the different subcellular organelle of target, line fluorescent probe preparation cost is low, specificity target different subcellular organelle, to lipid peroxidation PROCESS SENSITIVE and by the monitoring lipid peroxidation process of ratio fluorescent imaging relative quantification.
The technical solution used in the present invention is: the fluorescent probe that also can detect wherein lipid peroxidation process for the different subcellular organelle of target, with fluorine boron pyrroles for parent, has following general structure:
R in general formula
1, R
2=H, C
1-C
10straight or branched alkyl; R
3=H or
, wherein: R
4=
，X
- = Cl
-、Br
-、I
-、SO
4 2-、ClO
4 -、BrO
4 -、IO
4 - 。
One class for monitoring the preparation method of the fluorescent probe of lipid peroxidation process in different subcellular organelle, described R
3the fluorescent probe preparation method of=H is:
With the phenylacrolein of fluorine boron two pyrrole derivative of 1 mole and 1 mole for raw material; take piperidines as catalyzer; 4 molecular sieves are dewatering agent; the mol ratio of described fluorine boron two pyrrole derivative and catalyzer is 1:0.01; in toluene 130 DEG C; stir under the protection of argon gas or nitrogen gas, reaction 8-24h, the active methylene group of phenylacrolein and fluorine boron two pyrroles dewaters the fluorescent probe generating and contain conjugated double bond.
One class for monitoring the preparation method of the fluorescent probe of lipid peroxidation process in different subcellular organelle, described R
3=
fluorescent probe preparation method comprise the following steps:
(1) preparation of fluorine boron two pyrrole derivative M
With the phenylacrolein containing fluorine boron two pyrrole derivative of 3-chloropropyl and 1 mole of 1 mole for raw material, take piperidines as catalyzer, 4 molecular sieves are dewatering agent, the mol ratio of described fluorine boron two pyrrole derivative and catalyzer is 1:0.01, in toluene 130 DEG C, stir under the protection of argon gas or nitrogen gas, reaction 8-24h, the active methylene group of phenylacrolein and fluorine boron two pyrroles dewaters the fluorine boron two pyrrole derivative M generating and contain conjugated double bond;
(2) probe molecule is obtained by following two kinds of routes:
Route one
Fluorine boron two pyrrole derivative M and corresponding swollen amine are dissolved in acetone, chloroform or DMSO equal solvent, adding with intermediate M mol ratio is that the salt of wormwood of 1:1 and potassiumiodide react 3-10h at 30-130 DEG C, obtains fluorescent probe molecule; Described secondary amine is selected from dimethylamine, morpholine, methylpiperazine or benzyl diethylenediamine;
Route two
Fluorine boron two pyrrole derivative M and corresponding tertiary amine or triphenylphosphine derivates are dissolved in acetone, chloroform or DMSO equal solvent, the potassiumiodide that to add with intermediate M mol ratio be 1:1 reacts 3-24h at 30-130 DEG C, obtain probe molecule, described fluorescent probe stirs 24h with the sodium salt containing different anions or sylvite in methyl alcohol, make to carry out ion-exchange, obtain the fluorescent probe containing different gegenion; Described tertiary amine is selected from Trimethylamine 99, dimethyl benzyl amine or dimethylamino propionic aldehyde, and described triphenylphosphine derivates is selected from triphenylphosphine or aldehyde radical triphenylphosphine.
Described fluorescent probe respectively target is positioned the lipid peroxidation process indicating subcellular organelle in different subcellular organelles and by the change of fluorescence spectrum.Described fluorescent probe is used for the target location of different subcellular organelle in viable cell and the detection of internal lipids peroxidation process thereof.The viable cell that can be labeled is Hella cell strain, MCF-7 cell strain, RAW264.7 cell strain, 7702 cell strains etc.
The invention has the beneficial effects as follows: a series of for the different subcellular organelle of target and the fluorescent probe that can detect wherein lipid peroxidation process with fluorine boron pyrroles for substrate and phenylacrolein react under nitrogen or argon, take piperidines as catalyzer, 4 molecular sieves be dewatering agent; Gained reactant is obtained by reacting fluorescent probe molecule with swollen amine, tertiary amine or triphenylphosphine again.Plurality of probes molecule is at the long-wavelength region emitting fluorescence of 590nm, responsive to active oxygen radical, namely after participating in the lipid peroxidation process in viable cell, conjugated double bond is destroyed, its emission wavelength becomes the short wavelength of about 520nm, changed by short wavelength (about 520nm) and the ratio of the fluorescent emission intensity at long wavelength (about 590nm) two place, the level of lipid peroxidation in viable cell can be detected.Meanwhile, different probe is due to containing different activities group (i.e. R
4), it has different subcellular organelle targetings, and namely plurality of probes can detect the lipid peroxidation process in different subcellular organelle in viable cell (plastosome, lysosome or cytolemma) respectively.This probe nature is stablized, be easy to long-term preservation, there is sensitive response to lipid peroxidation process, and indicate the degree of lipid peroxidation by ratio fluorescent imaging, for the lipid peroxidation correlated process of probing in viable cell in microtexture provides detection reagent intuitively.
Accompanying drawing explanation
Fig. 1 is that fluorescent probe A is at CH
2cl
2the spectrum change after lipid peroxidation process is participated in solution.
Fig. 2 is that fluorescent probe A drips the fluorescence imaging after dyeing to the fat in MCF-7 cell.
Fig. 3 is that fluorescent probe A drips interior lipid peroxidation process to fat in MCF-7 cell and carries out fluorescence imaging detection.
Fig. 4 is the spectrum change after fluorescent probe B-1 participates in lipid peroxidation process in the solution.
Fig. 5 is that fluorescent probe B-1 is to the fluorescence imaging after lysosome dyeing in RAW264.7 cell.
Fig. 6 is that fluorescent probe B-1 detects the fluorescence imaging that lysosome inner lipid peroxidation process in RAW264.7 cell is carried out.
Fig. 7 is that fluorescent probe C-1 is to the fluorescence imaging after the dyeing of MCF-7 cell Mitochondria.
Fig. 8 is that fluorescent probe C-1 detects the fluorescence imaging that MCF-7 cell Mitochondria inner lipid peroxidation process is carried out.
Fig. 9 is that fluorescent probe C-2 is to the fluorescence imaging after cytolemma dyeing in Hella cell.
Figure 10 is that fluorescent probe C-2 detects the fluorescence imaging that lipid peroxidation process on cytolemma in Hella cell is carried out.
Embodiment
embodiment 1
Tetramethyl-fluorine boron pyrroles 500mg, phenylacrolein 129mL is added in two mouthfuls of reaction flasks, the piperidines adding 500mL is again catalyzer, 4 molecular sieves are dewatering agent, 120 DEG C of stirring reaction 8h in toluene, reactant decompression is spin-dried for, after removing toluene, silicagel column is separated (elutriant is methylene dichloride: normal hexane=1:4) and obtains violet solid 155mg, productive rate 23%.
embodiment 2
Tetramethyl-fluorine boron pyrroles 500mg, phenylacrolein 94mL is added in two mouthfuls of reaction flasks, the piperidines adding 500mL is again catalyzer, 4 molecular sieves are dewatering agent, 120 DEG C of stirring reaction 8h in toluene, reactant decompression is spin-dried for, after removing toluene, silicagel column is separated (elutriant is methylene dichloride: normal hexane=1:4) and obtains violet solid 194mg, productive rate 31%.
Being dissolved in DMSO by obtaining product 100mg in upper step, adding excessive morpholine 100mL, 24mg K
2cO
3with 30mg KI, 60 DEG C reaction 12h, reactant washing and by CH
2cl
2extraction, retain organic phase, after anhydrous magnesium sulfate drying, decompression is spin-dried for, and silicagel column is separated (elutriant is methylene dichloride: methyl alcohol=20:1) and obtains violet solid 81mg, productive rate 75%.
embodiment 3
Tetramethyl-fluorine boron pyrroles 500mg, phenylacrolein 88mL is added in two mouthfuls of reaction flasks, the piperidines adding 500mL is again catalyzer, 4 molecular sieves are dewatering agent, 120 DEG C of stirring reaction 8h in toluene, reactant decompression is spin-dried for, after removing toluene, silicagel column is separated (elutriant is methylene dichloride: normal hexane=1:4) and obtains violet solid 217mg, productive rate 35%.
Being dissolved in acetone by obtaining product 100mg in upper step, adding excess tertiary amine 50mg, KI 30mg, 60 DEG C of reaction 12h, concentration of reaction solution, and add ether, have intense violet color solid to separate out, be target product.Fluorescent probe is dissolved in methyl alcohol, add the potassium periodate of 1000mg, after 50 DEG C of stirring 24h, reaction solution decompression is spin-dried for, be dissolved in a small amount of methylene dichloride, cross and filter inorganic salt, retain filtrate, decompression is spin-dried for again, obtain 141mg intense violet color solid, be the fluorescent probe that gegenion is periodate, two step overall yields 88%.
embodiment 4
Tetramethyl-fluorine boron pyrroles 500mg, phenylacrolein 83mL is added in two mouthfuls of reaction flasks, the piperidines adding 500mL is again catalyzer, 4 molecular sieves are dewatering agent, 120 DEG C of stirring reaction 8h in toluene, reactant decompression is spin-dried for, after removing toluene, silicagel column is separated (elutriant is methylene dichloride: normal hexane=1:4) and obtains violet solid 196mg, productive rate 32%.
Being dissolved in acetone by obtaining product 100mg in upper step, adding excessive triphenylphosphine formaldehyde 200mg, KI 30mg, 60 DEG C of reaction 12h, concentration of reaction solution, and add ether, have intense violet color solid to separate out, be target product.Fluorescent probe is dissolved in methyl alcohol, add the KBr of 500mg, after 50 DEG C of stirring 24h, reaction solution decompression is spin-dried for, be dissolved in a small amount of methylene dichloride, cross and filter inorganic salt, retain filtrate, decompression is spin-dried for again, obtain 140mg intense violet color solid, be the fluorescent probe that gegenion is bromide anion, two step overall yields 91%.
embodiment 5
Fluorescent probe A is used for fat in viable cell and drips the detection of middle lipid peroxidation process.Fat in the cells such as Hella cell strain, MCF-7 cell strain, RAW264.7 cell strain drips and all by probe mark, and can detect level of lipid peroxidation wherein.
Fig. 1 is at solution (CH
2cl
2) in by pharmaceutical chemicals simulation lipid peroxidation process time probe spectrum change, along with the prolongation of lipid peroxidation time, probe strengthens gradually in the fluorescence intensity at 520nm place, weakens gradually at the fluorescence at 590nm place.Wherein illustration be two place's peak intensity ratios over time, with the intensification of level of lipid peroxidation, the strong and strong ratio in peak, long wave place in peak, shortwave place also strengthens, and namely rate value can reflect the degree of lipid peroxidation.
Fig. 2 uses the fluorescent probe A of 1mM to MCF-7 cell dyeing 30 min and uses PBS to wash the fluorescence imaging after twice.Excitation wavelength 488 nm, acquisition range 560-630 nm, cell imaging fat drips clear-cut, disturbs without bias light.
Fig. 3 is that the cytolipin after dyeing drips interior generation lipid peroxidation process, same use 488nm laser excitation, gather short wavelength emissions light (a) in 500-560nm interval simultaneously and gather longwave transmissions (b) with 560-630nm interval, wherein short wavelength emissions shows that probe take part in fat and drips interior lipid peroxidation process; Intuitively can reflect that in cell, fat drips interior level of lipid peroxidation (c) by the ratio chart picture of shortwave passage and long wave passage.
embodiment 6
Fluorescent probe B-1 is used for the detection of lipid peroxidation process in lysosome in viable cell.Lysosome in the cells such as Hella cell strain, MCF-7 cell strain, RAW264.7 cell strain all by probe mark, and can detect level of lipid peroxidation wherein.
Fig. 4 is the spectrum change by probe during pharmaceutical chemicals simulation lipid peroxidation process in solution (water/methyl alcohol=2/1), along with the prolongation of lipid peroxidation time, probe strengthens gradually in the fluorescence intensity at 520nm place, weakens gradually at the fluorescence at 590nm place.Wherein illustration be two place's peak intensity ratios over time, with the intensification of level of lipid peroxidation, the strong and strong ratio in peak, long wave place in peak, shortwave place also strengthens, and namely rate value can reflect the degree of lipid peroxidation.
Fig. 5 uses the fluorescent probe B-1 of 1mM to RAW264.7 cell dyeing 5 min and uses PBS to wash the fluorescence imaging after twice.Excitation wavelength 488 nm, acquisition range 560-630 nm, cell imaging lysosome clear-cut, disturbs without bias light.
Lipid peroxidation process is there is in Fig. 6 in Cytolysosome after dyeing, same use 488nm laser excitation, gather short wavelength emissions light (a) in 500-560nm interval simultaneously and gather longwave transmissions (b) with 560-630nm interval, wherein short wavelength emissions shows that probe take part in the lipid peroxidation process in lysosome; The level of lipid peroxidation (c) in cell in lysosome intuitively can be reflected by the ratio chart picture of shortwave passage and long wave passage.
embodiment 7
Fluorescent probe C-1 is used for the detection of lipid peroxidation process in viable cell Mitochondria.Plastosome in the cells such as Hella cell strain, MCF-7 cell strain, RAW264.7 cell strain all by probe mark, and can detect level of lipid peroxidation wherein.
Fig. 7 uses the fluorescent probe C-1 of 1mM to MCF-7 cell dyeing 5 min and uses PBS to wash the fluorescence imaging after twice.Excitation wavelength 488 nm, acquisition range 560-630 nm, cell imaging plastosome clear-cut, disturbs without bias light.
Lipid peroxidation process is there is in Fig. 8 in cell mitochondrial after dyeing, same use 488nm laser excitation, gather short wavelength emissions light (a) in 500-560nm interval simultaneously and gather longwave transmissions (b) with 560-630nm interval, wherein short wavelength emissions shows that probe take part in Intramitochondrial lipid peroxidation process; The level of lipid peroxidation (c) in cell Mitochondria intuitively can be reflected by the ratio chart picture of shortwave passage and long wave passage.
embodiment 8
Fluorescent probe C-2 is the detection of lipid peroxidation process on cytolemma in viable cell.Cytolemma in the cells such as Hella cell strain, MCF-7 cell strain, RAW264.7 cell strain all by probe mark, and can detect level of lipid peroxidation wherein.
Fig. 9 uses the fluorescent probe C-2 of 1mM to Hella cell dyeing 5 min and uses PBS to wash the fluorescence imaging after twice.Excitation wavelength 488 nm, acquisition range 560-630 nm, cell imaging cytolemma clear-cut, disturbs without bias light.
Figure 10 there is lipid peroxidation process in the cell film after dyeing, same use 488nm laser excitation, gather short wavelength emissions light (a) in 500-560nm interval simultaneously and gather longwave transmissions (b) with 560-630nm interval, wherein short wavelength emissions shows that probe take part in the lipid peroxidation process on cytolemma; The level of lipid peroxidation (c) on cell in cytolemma intuitively can be reflected by the ratio chart picture of shortwave passage and long wave passage.
Claims (4)
1. a class is for monitoring the fluorescent probe of lipid peroxidation process in different subcellular organelle, with fluorine boron pyrroles for parent, it is characterized in that, this probe has following general structure:
R in general formula
1, R
2=H, C
1-C
10straight or branched alkyl; R
3=H or
, wherein: R
4=
or
, X
-=Cl
-, Br
-, I
-, SO
4 2-, ClO
4 -, BrO
4 -or IO
4 -.
2. a class according to claim 1 is for monitoring the preparation method of the fluorescent probe of lipid peroxidation process in different subcellular organelle, it is characterized in that, described R
3the fluorescent probe preparation method of=H is:
With the phenylacrolein of fluorine boron two pyrrole derivative of 1 mole and 1 mole for raw material; take piperidines as catalyzer; 4 molecular sieves are dewatering agent; the mol ratio of described fluorine boron two pyrrole derivative and catalyzer is 1:0.01; in toluene 130 DEG C; stir under the protection of argon gas or nitrogen gas, reaction 8-24h, the active methylene group of phenylacrolein and fluorine boron two pyrrole derivative dewaters the fluorescent probe generating and contain conjugated double bond.
3. a class according to claim 1 is for monitoring the preparation method of the fluorescent probe of lipid peroxidation process in different subcellular organelle, it is characterized in that, described R
3=fluorescent probe preparation method comprise the following steps:
(1) preparation of fluorine boron two pyrrole derivative M
With the phenylacrolein containing fluorine boron two pyrrole derivative of 3-chloropropyl and 1 mole of 1 mole for raw material, take piperidines as catalyzer, 4 molecular sieves are dewatering agent, the mol ratio of described fluorine boron two pyrrole derivative and catalyzer is 1:0.01, in toluene 130 DEG C, stir under the protection of argon gas or nitrogen gas, reaction 8-24h, the active methylene group of phenylacrolein and fluorine boron two pyrroles dewaters the fluorine boron two pyrrole derivative M generating and contain conjugated double bond;
(2) probe molecule is obtained by following route one or route two synthesis:
Route one:
Fluorine boron two pyrrole derivative M and swollen amine are dissolved in acetone, chloroform or DMSO solvent, adding respectively with fluorine boron two pyrrole derivative M mol ratio is that the salt of wormwood of 1:1 and potassiumiodide react 3-10h at 30-130 DEG C, obtains fluorescent probe; Described secondary amine is selected from dimethylamine, morpholine, methylpiperazine or benzyl diethylenediamine;
Route two:
Fluorine boron two pyrrole derivative M and tertiary amine or triphenylphosphine derivates are dissolved in acetone, chloroform or DMSO solvent, the potassiumiodide that to add with fluorine boron two pyrrole derivative M mol ratio be 1:1 reacts 3-24h at 30-130 DEG C, obtain fluorescent probe, described fluorescent probe stirs 24h with the sodium salt containing different anions or sylvite in methyl alcohol, make to carry out ion-exchange, obtain the fluorescent probe containing different gegenion; Described tertiary amine is selected from Trimethylamine 99, dimethyl benzyl amine or dimethylamino propionic aldehyde, and described triphenylphosphine derivates is selected from triphenylphosphine or aldehyde radical triphenylphosphine.
4. a class according to claim 1 is for monitoring the application of the fluorescent probe of lipid peroxidation process in different subcellular organelle, it is characterized in that: described fluorescent probe respectively target is positioned the lipid peroxidation process indicating subcellular organelle in different subcellular organelles and by the change of fluorescence spectrum.
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