CN107619390A - One kind is used to detect nitric oxide production two-photon fluorescence probe near cell membrane - Google Patents
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Abstract
One kind is used to detect nitric oxide production two-photon fluorescence probe near cell membrane, belongs to field of fine chemical.The plurality of probes is obtained using naphthalimide as chromophore by introducing hydrophilic quaternary ammonium salt cation and hydrophobic fat carbochain.Amphipathic class phospholipid molecule structure causes probe molecule to have cytoplasma membrane targeting, quickly, stably can rest on cell membrane, and passes through the presence for strengthening nitric oxide molecule near indicator cells film of fluorescence signal.Plurality of probes molecule can not only excite carry out fluorescence imaging by single-photon laser, can more realize that 690nm-950nm two-photon laser carries out fluorescence imaging, be adapted to carry out fluoroscopic examination inside cell and profound biological tissue.Probe molecule solid state property is stable, is easy to preserve, can be as the detection reagent for probing into nitric oxide Relevant Physiological Courses.
Description
Technical field
The present invention relates to nitric oxide production two-photon fluorescence probe near one kind detection cell membrane, it belongs to fine chemistry industry skill
Art field.
Background technology
Nitric oxide is nitrogen oxide, and its chemical property is active, and latter stage in 20th century is proved to that there is important physiology to adjust
Function is saved, such as the diastole of blood vessel is reconciled in cardiovascular system, nervous system, is had in immune system and is sterilized, be antitumor
Deng effect；And its metabolic disorder in cell or tissue, the diseases such as gaucher's disease, cavity cancer can be caused.Therefore, highly sensitive,
Nitric oxide in the detection machine body of high selectivity has important medical significance.
Fluorescence microscopy is suitable for the real-time detection of living cells or tissue as a kind of monitoring means in real time directly perceived.
And as the door of cell, cell membrane is the first stop for receiving the effect of outer signals molecules mediate both；For individual cell lines cell
Film is also the main positions of nitric oxide generation, as the initiate point of nitric oxide conciliation effect.But it there is no can be used at present
Detect nitric oxide production fluorescence probe near cell membrane.Therefore, we devise it is a series of with cell membrane target function one
Nitrogen oxide fluorescent probe molecule, more directly perceived and succinct research tool is provided for the research of nitric oxide relevant disease.
The content of the invention
In order to solve the above-mentioned technical problem, it is used for target cell membrane and to detect cell membrane attached the invention provides a series of
Fluorescence probe of nearly nitric oxide molecule and preparation method thereof, plurality of probes can fast and stable be positioned at cell membrane, and can pass through
Single photon and two-photon laser excite carry out fluorescence imaging.
The technical solution adopted by the present invention is：Target cell membrane simultaneously can detect nitric oxide production fluorescence spy near cell membrane
Pin, using naphthalimide as parent, there is following general structure：
N=0,1,2,3 or 4 in formula；Wherein：R2=
CH3、X-=Cl-、Br-、I-、SO4 2-、ClO4 -、BrO4 -
Or IO4 -；R1=C8-C18Straight or branched alkyl.
One kind is used for the preparation method for detecting the fluorescence probe of nitric oxide molecule near cell membrane, the fluorescence probe system
Preparation Method is：
With 1 mole DMF, acetonitrile, third are dissolved in containing 2-chloroethyl amine (or the more chloro primary amine of carbon number) with corresponding secondary amine
Ketone or DMSO equal solvents, it is 1 to add with 2-chloroethyl amine mol ratio:5 potassium carbonate and KI reacts 3- at 30-130 DEG C
24h, obtain intermediate A 1；Intermediate A 1 and compound A2 is using mol ratio as 5:1-1:1 in anhydrous sodium acetate (is 0.1- with A2
10.0 molar equivalents) catalysis under be heated to 100-130 degree reaction 5-9h, by alumina column separating-purifying, obtain intermediate
A3；Intermediate A 3 is dissolved in excessive 5mol/L sulfuric acid, back flow reaction 2h-5h, is stopped reaction, is poured into trash ice, make while hot
PH is adjusted to alkalescent with NaOH, is had yellow solid to be separated out from solution, is filtrated to get intermediate A 4, is directly used in without purification
React in next step；Intermediate A 4 is added in 20mL glacial acetic acid with bromo- 1, the 8- naphthalic anhydrides of 4-, is heated to reflux 6h, is stopped anti-
Should, reaction solution is poured into trash ice, is adjusted to alkalescence using sodium hydroxide, is extracted using dichloromethane, utilizes neutral alumina column
Separating-purifying, obtain intermediate A 5；Intermediate A 5 and excessive alkylamine are added in 8mL DMSO, 100-150 DEG C of stirring 3h, are made
Extracted with dichloromethane and water, organic phase uses silicagel column separating-purifying, obtains intermediate A 6；A6 is dissolved in a small amount of dichloromethane
In, it is stirred at room temperature, adds season aminating agent, continues to stir 1-24h, intermediate A 7 is separated out from solvent, is filtrated to get in solid
Mesosome A7；A7 is catalyzed in tetrahydrofuran using palladium carbon, and hydrogenating reduction 48h, filtrate decompression is spin-dried for, using dichloromethane and just oneself
Alkane recrystallization purification, obtains yellow powder, i.e. target-probe；The fluorescence probe and sodium salt or potassium containing different anions
Salt stirs 24h in methyl alcohol, is allowed to carry out ion exchange, obtains the fluorescence probe containing different counter ions.
The fluorescence probe quickly, can be rested on stably on cell membrane, and is indicated carefully by the enhancing of fluorescence signal
The presence of nitric oxide molecule near after birth；Plurality of probes molecule can not only be excited by single-photon laser carry out fluorescence into
Picture, it can more realize that 690nm-950nm two-photon laser carries out fluorescence imaging, be adapted to inside cell and profound biological tissue
Carry out fluoroscopic examination.
The beneficial effects of the invention are as follows：The probe introduces different hydrophilic o-phenylenediamine and derived using naphthalimide as parent
Thing and hydrophobicity long alkyl chain obtain target-probe molecule.The plurality of probes molecule to amphipathic class structure of phospholipid,
Cell membrane can be positioned at fast and stable；Its o-phenylenediamine structure is sensitive to nitric oxide molecule, with reference to rear tissue probe point
PET effects in son so that probe molecule recovers fluorescent emission, and then indicates the presence of nitric oxide molecule；With nitric oxide
Probe molecule after response launches hyperfluorescence in 540nm or so, neuronal cell cell fluorescence is imaged and to mouse brain slice
Histofluorescence is imaged, it is shown that the plurality of probes can not only excite carry out fluorescence imaging by single-photon laser, can more realize
690nm-950nm two-photon laser carries out fluorescence imaging, is adapted to carry out fluorescence inspection inside cell and profound biological tissue
Survey.Probe molecule solid state property is stable, is easy to preserve, and can be tried as the detection for probing into nitric oxide Relevant Physiological Courses
Agent.
Brief description of the drawings
Fig. 1 be probe P-1 in the solution fluorescence spectrum with nitric oxide concentration change.
Fig. 2 is inspections of the probe P-1 in the solution to nitric oxide selectivity.
Fig. 3 is probe P-1 to the nitric oxide production fluorescence imaging of exogenous after neuronal cell cell dyeing.
Fig. 4 is probe P-1 to the nitric oxide production fluorescence imaging of exogenous after mouse brain slice tissue staining.
Embodiment
Embodiment 1
2-chloroethyl amine hydrochloride 1g and dimethylamine hydrochloride 3.5g is dissolved in 30mL DMF, adds potassium carbonate 6g and KI
1.4g, 8h is reacted at 30 DEG C, after reaction terminates, 200mL ether is added in phase reaction liquid, washed 3 times with water extraction, retain ether
Phase, after anhydrous magnesium sulfate is dried, it is evaporated under reduced pressure and removes ether, obtain intermediate A 1-1；By compound A2-1 4g, acetic anhydride
Sodium 2.5g and A3 4.09g are mixed, and are heated to 100 DEG C of reaction 5h, and solution is changed into black from red, and it is mixed to stop reaction cooling reaction
Compound is to room temperature, and using dichloromethane dissolving mixt, washing three times, dries organic phase, filtering, removal of solvent under reduced pressure, post layer
Separating-purifying is analysed, obtains intermediate A 3-1；Compound A-13 1.2g is dissolved in the sulfuric acid that 20ml concentration is 5mol/L, backflow is anti-
2h is answered, stops reaction, while hot pours into reaction solution in trash ice, adding sodium hydroxide makes solution be changed into alkalescent, and solution is by dark red
Discoloration is yellow green turbid solution, separates out yellow mercury oxide, and intermediate A 4-1 is arrived in filtering, is directly used in without purification anti-in next step
Should；Intermediate A 4-1 0.5g and bromo- 1, the 8- naphthalic anhydrides 0.65g of 4- are added in 20mL glacial acetic acid, are heated to reflux 6h, are stopped
Only react, reaction solution is poured into trash ice, is adjusted to alkalescence using sodium hydroxide, is extracted using dichloromethane, utilizes neutral alumina
Aluminium post separation purifies, and obtains intermediate A 5-1；Intermediate A 5-1 0.2g and excessive octadecylamine are added in 8mL DMSO,
100 DEG C of stirring 3h, are extracted using dichloromethane and water, and organic phase is dried through anhydrous magnesium sulfate, is evaporated under reduced pressure and is removed solvent, is used
Silicagel column separating-purifying, obtain intermediate A 6-1；A6-1 0.13g are dissolved in 5mL dichloromethane, are stirred at room temperature, add iodine first
Alkane, continue to stir 24h, intermediate A 7-1 separates out from solvent, is filtrated to get solid intermediate A7-1；A7-1 0.1g are dissolved in
In 30mL tetrahydrofurans, add the palladium carbons of 0.1g 10%, hydrogenating reduction 48h, filtrate decompression is spin-dried for, using dichloromethane and just oneself
Alkane recrystallization purification, obtains yellow powder, and above-mentioned yellow powder stirs 24h with excessive sodium bromide, is allowed to carry out in methyl alcohol
Ion exchange, obtain fluorescence probe P-1.
Embodiment 2
3- chloro propyl amine hydrochloric acid salts 1g and morpholine 3.8g is dissolved in 50mL acetonitriles, potassium carbonate 5g and KI 1.2g is added, at 30 DEG C
Lower reaction 8h, after reaction terminates, 200mL ether is added in phase reaction liquid, washed 3 times with water extraction, retain ether phase, anhydrous magnesium sulfate
After drying, it is evaporated under reduced pressure and removes ether, obtain intermediate A 1-2；By compound A2-2 4g, anhydrous sodium acetate 2.5g and A3
4.09g is mixed, and is heated to 100 DEG C of reaction 5h, and solution is changed into black from red, stops reaction cooling reactant mixture to room temperature,
Using dichloromethane dissolving mixt, washing three times, is dried organic phase, filtered, removal of solvent under reduced pressure, column chromatography for separation purification,
Obtain intermediate A 3-2；The 1.2g of compound A-13-2 is dissolved in the sulfuric acid that 20ml concentration is 5mol/L, back flow reaction 2h, stopped
Reaction, while hot pours into reaction solution in trash ice, and adding sodium hydroxide makes solution be changed into alkalescent, and solution is changed into yellowish green from kermesinus
Color turbid solution, yellow mercury oxide is separated out, intermediate A 4-2 is arrived in filtering, is directly used in without purification and is reacted in next step；Intermediate A 4-
2 0.5g and bromo- 1, the 8- naphthalic anhydrides 0.55g of 4- are added in 20mL glacial acetic acid, are heated to reflux 6h, stop reaction, reaction solution
Pour into trash ice, adjusted to alkalescence using sodium hydroxide, extracted using dichloromethane, using neutral alumina column separating-purifying,
Obtain intermediate A 5-2；Intermediate A 5-2 0.2g and excessive alkylamine are added in 8mL DMSO, 100 DEG C of stirring 3h, use two
Chloromethanes is extracted with water, and organic phase is dried through anhydrous magnesium sulfate, is evaporated under reduced pressure and is removed solvent, using silicagel column separating-purifying, obtains
To intermediate A 6-2；A6-2 0.13g are dissolved in 5mL dichloromethane, are stirred at room temperature, add excessive propane sultone, continue to stir
24h is mixed, intermediate A 7-2 separates out from solvent, is filtrated to get solid intermediate A7-2；A7-2 0.1g are dissolved in 30mL tetrahydrofurans
In, the palladium carbons of 0.1g 10%, hydrogenating reduction 48h are added, filtrate decompression is spin-dried for, purified using recrystallize with dichloromethane, obtains yellow
Powder, above-mentioned yellow powder stir 24h with excessive sodium perchlorate, are allowed to carry out ion exchange in methyl alcohol, obtain fluorescence spy
Pin P-2.
Embodiment 3
4- neoprene amine 5g and pyrroles 4g is dissolved in 30mL acetonitriles, is added potassium carbonate 5g and KI 1.2g, is reacted at 30 DEG C
12h, after reaction terminates, 200mL ether is added in phase reaction liquid, washed 3 times with water extraction, retain ether phase, anhydrous magnesium sulfate is dried
Afterwards, it is evaporated under reduced pressure and removes ether, obtains intermediate A 1-3；Compound A2-3 4g, anhydrous sodium acetate 2g and A3 3.5g are mixed,
100 DEG C of reaction 5h are heated to, solution is changed into black from red, stops reaction cooling reactant mixture to room temperature, uses dichloromethane
Alkane dissolving mixt, washing three times, dry organic phase, filtering, removal of solvent under reduced pressure, column chromatography for separation purification, obtain intermediate
A3-3；The 2g of compound A-13-3 is dissolved in the sulfuric acid that 20ml concentration is 5mol/L, back flow reaction 2h, stops reaction, while hot will be anti-
Liquid is answered to pour into trash ice, adding sodium hydroxide makes solution be changed into alkalescent, and solution is changed into yellow green turbid solution from kermesinus, separates out
Intermediate A 4-3 is arrived in yellow mercury oxide, filtering, is directly used in without purification and is reacted in next step；Intermediate A 4-3 0.5g and 4- is bromo-
1,8- naphthalic anhydride 0.6g is added in 20mL glacial acetic acid, is heated to reflux 6h, stops reaction, and reaction solution is poured into trash ice, made
Adjusted to alkalescence with sodium hydroxide, extracted using dichloromethane, using neutral alumina column separating-purifying, obtain intermediate A 5-
3；Intermediate A 5-3 0.2g and excessive hexadecylamine are added in 8mL DMSO, 120 DEG C stirring 3h, using dichloromethane with
Water is extracted, and organic phase is dried through anhydrous magnesium sulfate, is evaporated under reduced pressure and is removed solvent, using silicagel column separating-purifying, obtains intermediate
A6-3；A6-3 0.1g are dissolved in 5mL dichloromethane, are stirred at room temperature, adds excessively to the benzyl chloride of benzene two, continues to stir 24h, it is middle
Body A7-3 separates out from solvent, is filtrated to get solid intermediate A7-3；A7-3 0.1g are dissolved in 30mL tetrahydrofurans, are added
The palladium carbons of 0.1g 10%, hydrogenating reduction 48h, filtrate decompression are spin-dried for, and using dichloromethane and n-hexane recrystallization purification, obtain Huang
Color powder, above-mentioned yellow powder stir 24h with excessive sodium iodide, are allowed to carry out ion exchange in methyl alcohol, obtain fluorescence spy
Pin P-3.
Embodiment 4
5- chlorine amylamine 5g and cyclopentamine 4g is dissolved in 30mL acetonitriles, is added potassium carbonate 5g and KI 1.2g, is reacted at 30 DEG C
12h, after reaction terminates, 200mL ether is added in phase reaction liquid, washed 3 times with water extraction, retain ether phase, anhydrous magnesium sulfate is dried
Afterwards, it is evaporated under reduced pressure and removes ether, obtains intermediate A 1-4；Compound A2-4 4g, anhydrous sodium acetate 2g and A3 3.5g are mixed,
100 DEG C of reaction 5h are heated to, solution is changed into black from red, stops reaction cooling reactant mixture to room temperature, uses dichloromethane
Alkane dissolving mixt, washing three times, dry organic phase, filtering, removal of solvent under reduced pressure, column chromatography for separation purification, obtain intermediate
A3-4；The 2g of compound A-13-4 is dissolved in the sulfuric acid that 20ml concentration is 5mol/L, back flow reaction 2h, stops reaction, while hot will be anti-
Liquid is answered to pour into trash ice, adding sodium hydroxide makes solution be changed into alkalescent, and solution is changed into yellow green turbid solution from kermesinus, separates out
Intermediate A 4-4 is arrived in yellow mercury oxide, filtering, is directly used in without purification and is reacted in next step；Intermediate A 4-4 0.5g and 4- is bromo-
1,8- naphthalic anhydride 0.6g is added in 20mL glacial acetic acid, is heated to reflux 6h, stops reaction, and reaction solution is poured into trash ice, made
Adjusted to alkalescence with sodium hydroxide, extracted using dichloromethane, using neutral alumina column separating-purifying, obtain intermediate A 5-
4；Intermediate A 5-4 0.2g and excessive side chain octadecylamine are added in 8mL DMSO, 120 DEG C of stirring 3h, use dichloromethane
Alkane and water are extracted, and organic phase is dried through anhydrous magnesium sulfate, are evaporated under reduced pressure and are removed solvent, using silicagel column separating-purifying, in obtaining
Mesosome A6；A6-4 0.1g are dissolved in 5mL dichloromethane, are stirred at room temperature, add excessive propene aldehyde, continue to stir 24h, intermediate
A7-4 separates out from solvent, is filtrated to get solid intermediate A7-4；A7-4 0.1g are dissolved in 30mL tetrahydrofurans, add 0.1g
10% palladium carbon, hydrogenating reduction 48h, filtrate decompression are spin-dried for, and using dichloromethane and n-hexane recrystallization purification, obtain yellow powder
End, above-mentioned yellow powder stir 24h with excessive sodium metaperiodate, are allowed to carry out ion exchange, obtain fluorescence probe in methyl alcohol
P-4。
Embodiment 5
Fluorescence probe P-1 is used in living cells on cell membrane and nitric oxide production detection in brain tissue, can not only pass through monochromatic light
Sub- laser excitation carries out fluorescence imaging, can more realize that 690nm-950nm two-photon laser carries out fluorescence imaging, be adapted to cell
And fluoroscopic examination is carried out inside profound biological tissue.
In the probe P-1 aqueous solution during additional nitric oxide fluorescence probe intensity with nitric oxide addition change, by
Fig. 1, it is apparent that with it is nitric oxide production addition probe fluorescence intensity linear enhancing is presented first, consequently reach maximum
Value.
The change of fluorescence intensity, only exists as seen from Figure 2 when different activities oxygen species are added in the probe P-1 aqueous solution
When adding the nitric oxide aqueous solution, probe has significant Fluorescence Increasing, and probe can't be made by adding other reactive oxygen species
Fluorescence Increasing, illustrate that probe has good selectivity.
Fig. 3 is fluorescence imaging of the probe to neuronal cell, and cell is dyed 30min through 1 μM of probe P-1 and washed using PBS
Imaging experiment, fluorescent collecting scope 500-700nm are carried out after twice.It is glimmering when not adding the nitric oxide aqueous solution wherein to scheme a
Photoimaging, excitation wavelength 405nm, it can be seen that fluorescence intensity is very weak；Scheme b be add the nitric oxide aqueous solution after fluorescence into
Picture, excitation wavelength 405nm, it can be seen that fluorescence intensity is very high, and cell outline is clear, illustrates that probe can be real on cell membrane
Now to the detection of nitric oxide molecule；Figure c is fluorescence imaging when being excited using 900nm two-photon lasers, it can be seen that is had
The imaging effect same with figure b, illustrates that probe can be very good to realize the fluorescence imaging under two-photon excitation.
Fig. 4 is fluorescence imaging of the probe to mouse brain section, and mouse brain section uses PBS after 1 μM of probe P-1 dyes 30min
Imaging experiment, fluorescent collecting scope 500-700nm are carried out after washing twice.Scheme the light field image that d is mouse brain section；E is schemed not add
In the brain tissue fluorescence imaging of 100 μm of depth, excitation wavelength 900nm, it can be seen that fluorescence is strong when entering the nitric oxide aqueous solution
Degree is very weak；F is schemed for the brain tissue fluorescence imaging after the addition nitric oxide aqueous solution in 100 μm of depth, excitation wavelength 900nm,
It can be seen that there is significant Fluorescence Increasing, illustrate probe to can be very good to realize under two-photon excitation and carry out fluorescence in tissue depth
Imaging.
Claims (3)
1. one kind is used for the fluorescence probe for detecting nitric oxide molecule near cell membrane, using naphthalimide as parent, its feature exists
In the probe molecule has following general structure：
N=0,1,2,3 or 4 in formula；
Wherein：R2=CH3、X-=Cl-、Br-、I-、
SO4 2-、ClO4 -、BrO4 -Or IO4 -；R1=C8-C18Straight or branched alkyl.
2. a kind of preparation side for being used to detect the fluorescence probe of nitric oxide molecule near cell membrane according to claim 1
Method, it is characterised in that the fluorescence probe preparation method is：
N=0,1,2,3 or 4；R1=C8-C18
Straight or branched alkyl；Wherein： X-=Cl-、Br-、I-、SO4 2-、ClO4 -、
BrO4 -Or IO4 -；
(1) with 1 mole of chloro primary amine and secondary amine R3H is dissolved in solvent, adds 1-1:5 moles of potassium carbonate and KI is in 30-130
3-24h is reacted at DEG C, obtains intermediate A 1；Solvent is DMF, acetonitrile, acetone or DMSO；
(2) intermediate A 1 and compound A2 is using mol ratio as 5:1-1:1 is heated to 100-130 degree under the catalysis of anhydrous sodium acetate
5-9h is reacted, by alumina column separating-purifying, obtains intermediate A 3；The mol ratio of the compound A2 and anhydrous sodium acetate is
0.1-10.0；
(3) intermediate A 3 is dissolved in excessive 5mol/L sulfuric acid, back flow reaction 2h-5h, is stopped reaction, is poured into trash ice while hot
In, using NaOH regulation pH to alkalescent, there is yellow solid to be separated out from solution, be filtrated to get intermediate A 4,；
(4) intermediate A 4 is added in 20mL glacial acetic acid with bromo- 1, the 8- naphthalic anhydrides of 4-, is heated to reflux 6h, stops reaction, instead
Answer liquid to pour into trash ice, adjusted to alkalescence using sodium hydroxide, extracted using dichloromethane, carried using neutral alumina post separation
It is pure, obtain intermediate A 5；
(5) intermediate A 5 and alkylamine are added in DMSO, 100-150 DEG C of stirring 3h, are extracted using dichloromethane and water, organic
Silicagel column separating-purifying mutually is used, obtains intermediate A 6；
(6) A6 is dissolved in dichloromethane, be stirred at room temperature, add season aminating agent, continue to stir 1-24h, intermediate A 7 is from molten
Separated out in agent, be filtrated to get solid intermediate A7；
(7) A7 is catalyzed in tetrahydrofuran using palladium carbon, and hydrogenating reduction 48h, filtrate decompression is spin-dried for, using dichloromethane and just oneself
Alkane recrystallization purification, obtains yellow powder, i.e. target-probe；
The fluorescence probe stirs 24h in methyl alcohol with the sodium salt containing different anions or sylvite, is allowed to carry out ion friendship
Change, obtain the fluorescence probe containing different counter ions.
3. the application of the fluorescence probe of nitric oxide molecule near a kind of detection cell membrane according to claim 1, it is special
Sign is：The probe excites the two-photon laser for carrying out fluorescence imaging or 690nm-950nm to carry out fluorescence by single-photon laser
Imaging, for detecting the nitric oxide molecule near cell membrane.
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| CN113292543A (en) * | 2020-12-16 | 2021-08-24 | 大连理工大学 | Near-infrared fluorescent compound with targeting function and application thereof |
| CN113336701A (en) * | 2021-04-16 | 2021-09-03 | 温州医科大学 | Nitric oxide two-photon lipid droplet locking fluorescent probe, preparation method thereof and application thereof in detecting neuroinflammation |
| WO2022045316A1 (en) * | 2020-08-27 | 2022-03-03 | 株式会社同仁化学研究所 | Novel fluorescent compound, and lipid bilayer dyeing method and endocytosis detection method using said compound |
| CN115479928A (en) * | 2022-09-07 | 2022-12-16 | 山东大学 | LAbview-based synchronous detection control system and control method for low-intensity light signals |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108640913A (en) * | 2018-06-29 | 2018-10-12 | 成都丽璟科技有限公司 | A kind of preparation method of Ipratropium Bromide |
| WO2022045316A1 (en) * | 2020-08-27 | 2022-03-03 | 株式会社同仁化学研究所 | Novel fluorescent compound, and lipid bilayer dyeing method and endocytosis detection method using said compound |
| CN113292543A (en) * | 2020-12-16 | 2021-08-24 | 大连理工大学 | Near-infrared fluorescent compound with targeting function and application thereof |
| CN113292543B (en) * | 2020-12-16 | 2022-09-20 | 大连理工大学 | Near-infrared fluorescent compound with targeting function and application thereof |
| CN113336701A (en) * | 2021-04-16 | 2021-09-03 | 温州医科大学 | Nitric oxide two-photon lipid droplet locking fluorescent probe, preparation method thereof and application thereof in detecting neuroinflammation |
| CN115479928A (en) * | 2022-09-07 | 2022-12-16 | 山东大学 | LAbview-based synchronous detection control system and control method for low-intensity light signals |
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