CN106146342B - Fluorenyl salicylide buzane analog derivative and its preparation method and application - Google Patents
Fluorenyl salicylide buzane analog derivative and its preparation method and application Download PDFInfo
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- CN106146342B CN106146342B CN201510185918.2A CN201510185918A CN106146342B CN 106146342 B CN106146342 B CN 106146342B CN 201510185918 A CN201510185918 A CN 201510185918A CN 106146342 B CN106146342 B CN 106146342B
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- ZERJNAGZUCPHNB-UHFFFAOYSA-N tetrazane Chemical class NNNN ZERJNAGZUCPHNB-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 239000000523 sample Substances 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 238000004043 dyeing Methods 0.000 claims description 9
- 239000007787 solid Substances 0.000 abstract description 7
- 230000036541 health Effects 0.000 abstract description 6
- 238000001514 detection method Methods 0.000 abstract description 3
- 238000000338 in vitro Methods 0.000 abstract description 3
- 230000007246 mechanism Effects 0.000 abstract description 3
- 230000035479 physiological effects, processes and functions Effects 0.000 abstract description 3
- 230000009471 action Effects 0.000 abstract description 2
- 230000005281 excited state Effects 0.000 abstract description 2
- 238000012544 monitoring process Methods 0.000 abstract description 2
- 238000012546 transfer Methods 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- 239000003925 fat Substances 0.000 description 37
- 210000004027 cell Anatomy 0.000 description 26
- 235000019441 ethanol Nutrition 0.000 description 25
- -1 nitro, cyano, amino, sulfydryl Chemical group 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 14
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 6
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- 125000003118 aryl group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000002541 furyl group Chemical group 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000003214 pyranose derivatives Chemical class 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 125000005493 quinolyl group Chemical group 0.000 description 6
- 238000011160 research Methods 0.000 description 6
- 125000001544 thienyl group Chemical group 0.000 description 6
- 125000003944 tolyl group Chemical group 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
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- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 5
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
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- 238000001953 recrystallisation Methods 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- PJRGDKFLFAYRBV-UHFFFAOYSA-N 2-phenylthiophene Chemical class C1=CSC(C=2C=CC=CC=2)=C1 PJRGDKFLFAYRBV-UHFFFAOYSA-N 0.000 description 1
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- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
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- LGZXYFMMLRYXLK-UHFFFAOYSA-N mercury(2+);sulfide Chemical compound [S-2].[Hg+2] LGZXYFMMLRYXLK-UHFFFAOYSA-N 0.000 description 1
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- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The present invention relates to technical field of biological chemistry detection, and in particular to a kind of fluorenyl salicylide buzane analog derivative and its preparation method and application.Such compound can be freed in and out and is enriched at the fat drips in the cell of cell and specificity, intense fluorescence is become from original unstressed configuration, simultaneously in the molecule under the action of Excited state proton trans fer mechanism (ESIPT), present biggish Stokes shift, show as yellow, orange red or red fluorescence, compared with the solid state fluorescence of in vitro, substantially it is not displaced, it can accurately judge probe localized sites, to realize to cell fat drips structure, the monitoring of behavior and physiology course, in biology, medical treatment, health and energy field, with extremely wide application prospect.
Description
Technical field
The present invention relates to technical field of biological chemistry detection, and in particular to a kind of fluorenyl salicylide buzane analog derivative and its
Preparation method and application.
Background technique
With the fast development of national economy and the continuous improvement of living standards of the people, the real-time prison of personal health
It surveys, the prevention and treatment of disease are increasingly becoming the livelihood issues that people focus more on.It is examined relative to traditional iii vitro chemical
The harmfulness of retardance and radioactive ray on-line checking, the online imaging technique of fluorescence with its efficiently, green, strong real-time advantage gradually
The visual field for gradually entering into people is widely used in cellular immunology, microbiology, molecular biology, science of heredity, nerve biology
The fields such as the scientific research of, pathology, oncology, Clinical laboratory medicine, medicine, botany etc. and the people's livelihood.
The key technology of fluorescent imaging technology is exactly selection of the fluorescent material as label probe (or coloring agent).Preferably
Probe molecule is by physically or chemically acting on, and specific adsorption is in specific cell and tissue, under low energy Optical irradation
Two dimension or three-dimensional imaging are realized, by the health condition for judging cell or tissue with fluorescence color, intensity and distribution situation.
Compared with common chemical staining, the sensitivity of fluorescent staining will be higher by 100-1000 times, and pass through functionalized modification appropriate
The on-line analysis to living body can be realized.
Fat drips are the major storage places of intracellular neutral fats, are widely present in bacterium, yeast, plant, insect and move
In object cell.The difference in size of fat drips is very big, and diameter is differed from 40nm to 100um.Medical treatment, health field, fat drips always by
It is considered a kind of particle similar to glycogen, is used only to storing energy, when cell needs energy, for supplying energy, is
The cell inclusion of one 'inertia', thus fat drips are not valued by people within a very long time.But it is newest
Studies have shown that fat drips are not an intracellular simple energy reservoir, but a complexity, activity are vigorous, dynamic change
Multi-functional organelle.Fat drips can along cytoskeletal motor, and with other organelles interact, may lipid metabolism with
It plays an important role during storage, film transhipment, protein degradation and signal transduction.In addition, research is it is also shown that a variety of generations
Thanking property disease, such as obesity, fatty liver, cardiovascular disease and diabetes, the depot disease of neutral fats and Niemann Pick C disease
Disease, often all along with the exception of lipid storage.The attention of people is increasingly subject to accordingly, with respect to the biological study of fat drips.
Other than the application in health field, the screening of high fat drips content rudimentary plant is solving energy crisis field, by
Step attracts attention.In most of marine organisms, also contain a large amount of fat drips structure in the alginites of hundreds of millions meter in full, structure with
It will easily, rapidly be realized the inorganic of nature using " petroleum " is similar to if its carry out scale is dissolved breeding
Energy conversion is organic product, this is extremely important on solving increasingly neighbouring energy crisis.How to filter out
The problem of higher algae of fat drips content is cultivated and presently relevant researcher focuses more on.
Fluorescence probe is also gradually used in thin as the effective tool of the more mature research microcosmos of the mankind
The structure and physiology course research of born of the same parents' cell fat drips.Using under dark field, identification of the probe molecule to the specificity of ultrastructure
Ability and photoluminescent property intuitively observe various physiological activities and the in the process processes such as fat drips pattern, movement and decomposition.
It is analyzed from structure, fat drips are made of the hydrophobic core that Lipid monolayer and neutral fats are constituted, and surface point
It is furnished with many albumen.Relative to intracellular major part for hydrophilic environment, fat drips are comparatively hydrophobic oiliness region, institute
With many fat-soluble fluorescence probes can be marked and study to cell fat drips.But such probe must satisfy three
A primary condition could become compared with the fat drips research of current maturation.First, whether such fluorescence probe can freely go out
Enter cell: although the coating technology of Nano grade reduces the selectivity to probe structure, the cost under large-scale application
Increasing is also the problem of meriting attention, so, the probe structure for the cell that itself can be passed in and out seems more advantage；Second,
The selectivity of fluorescence probe: not all fat-soluble probe can identify fat drips, this may with outside fat drips core
There are one layer of single layer phospholipid molecule and various protein structures related；The on-off ratio of third, fluorescence probe is adjusted: most of to have excellent performance
Fluorescence probe all fat drips object is marked using " lighting ", and the organic probes enrichment at fat drips usually will cause
The decaying of fluorescence intensity, to be difficult to realize high-resolution imaging.Wherein, thirdly become and perplex the main of such probe development
Problem.
2001,1- methyl-1 of Tang this loyalty academician based on its discovery, 2,3,4,5- five phenyl thiophenes coughed up (MPPS) in acetonitrile
It does not shine in solution, and generates " abnormality " phenomenon of strong fluorescence after aggregation, propose " aggregation-induced emission (AIE) "
New idea, the working mechanism by " Internal Rotations of Molecules is limited (RIR) " are to explain this phenomenon well to generate, Er Qieyi
Obtain the support of many experimental results and theoretical calculation, developed one post " China card ", it is with independent intellectual property rights
Material and theoretical system.AIE class material solve traditional aromatic rings fluorescence chromophore assemble in water-soluble solvent quenching it is glimmering
Optical issue, not sending out in the fluorescence imaging and tracer, with background that can be realized high brightness in physiological buffered solution or aqueous medium
Light or weak light unimolecule realize high-resolution differentiation, are located in target biomacromolecule well.This AIE fluorescence probe
" lighting (light-up) " mode provide possibility for highly sensitive, contrast biological study, in the neck such as biology, medicine
Domain has epoch-making meaning.Based on the design concept of this kind of molecule, a large amount of " fat drips type " fluorescent molecular probe be produced and
The certain commercial potential quality for growing up, and showing.But these probes have a significant deficiency, exactly in fat drips
Fluorescence behaviour (fluorescence main peak position or luminescent color) and probe in the solid state the case where there are notable difference, fluorescence displacement is very big.
Because being difficult to estimate the amplitude of variation of luminescent color, it will lead to this class formation and be difficult to carry out fluorescence to complicated system and process
Dyeing and label, are unable to satisfy higher requirement in biosystem.
Summary of the invention
The object of the present invention is to provide a kind of fluorenyl salicylide buzane analog derivatives and its preparation method and application, solve existing
With the presence of in technology in fat drips Fluorescence behaviour (fluorescence main peak position or luminescent color) and probe in the solid state the case where obviously
Difference, fluorescence are displaced very big problem.
The technical proposal for solving the technical problem of the invention is: a kind of fluorenyl salicylide buzane analog derivative, knot
Structure general formula is as follows:
Wherein Ar indicates aromatic group or its derivative structure, substituent R1~R8It is respectively selected from hydrogen, alkyl, hydroxyl, alcoxyl
Base, nitro, cyano, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthalene, furyl, thienyl, pyrrole radicals, pyridyl group,
One of pyranose, quinolyl, indyl, carboxylic acid or carboxylic acid derivates, carbazyl or anilino-, the carbon of alkyl and alkoxy
Atomicity is respectively 1~12.
In fluorenyl salicylide buzane analog derivative of the invention, the substituent R1~R8It is respectively hydrogen, Ar structure is
Phenyl ring or phenyl ring derivative, preferred compound structural formula are as follows:
Wherein, A1~A4It is respectively selected from hydrogen, alkyl, hydroxyl, alkoxy, nitro, cyano, amino, sulfydryl, halogen atom, benzene
Base, tolyl, naphthalene, furyl, thienyl, pyrrole radicals, pyridyl group, pyranose, quinolyl, indyl, carboxylic acid or carboxylic acid spread out
One of biology, carbazyl or anilino-, the carbon atom number of alkyl and alkoxy is respectively 1~12.
In fluorenyl salicylide buzane analog derivative of the invention, the substituent R1~R8It is respectively hydrogen, Ar structure is
Naphthalene nucleus, anthracene nucleus, phenanthrene ring or naphthalene nucleus, anthracene nucleus, phenanthrene ring derivative, preferred compound structural formula are as follows:
Wherein, B1~B8It is respectively selected from hydrogen, alkyl, hydroxyl, alkoxy, nitro, cyano, amino, sulfydryl, halogen atom, benzene
Base, tolyl, naphthalene, furyl, thienyl, pyrrole radicals, pyridyl group, pyranose, quinolyl, indyl, carboxylic acid or carboxylic acid spread out
One of biology, carbazyl or anilino-, the carbon atom number of alkyl and alkoxy is respectively 1~12.
In fluorenyl salicylide buzane analog derivative of the invention, the substituent R1~R8It is respectively hydrogen, Ar structure is
Furans, thiophene, pyrroles, pyridine, pyrans, quinoline, indoles, carbazole, anilino- or pyrimidine radicals or Ar structure be furans, thiophene,
Pyrroles, pyridine, pyrans, quinoline, indoles, carbazole, anilino- or pyrimidine radicals derivative, preferred compound structure are as follows:
In fluorenyl salicylide buzane analog derivative of the invention, the substituent R1~R8It is respectively hydrogen, Ar structure is
The derivative of phenylethylene structure or phenylethylene structure, preferred compound structure are as follows:
In fluorenyl salicylide buzane analog derivative of the invention, Ar structure be benzene ring structure or phenyl ring derivative, it is described
Substituent R1~R8In an at least substituent group be selected from alkyl, hydroxyl, alkoxy, nitro, cyano, amino, sulfydryl, halogen atom, benzene
Base, tolyl, naphthalene, furyl, thienyl, pyrrole radicals, pyridyl group, pyranose, quinolyl, indyl, carboxylic acid or carboxylic acid spread out
One of biology, carbazyl or anilino-, the carbon atom number of alkyl and alkoxy is respectively 1~12；
Its preferred compound structure are as follows:
In fluorenyl salicylide buzane analog derivative of the invention, Ar structure is phenylethylene structure or phenylethylene structure
Derivative, the substituent R1~R8In an at least substituent group be selected from alkyl, hydroxyl, alkoxy, nitro, cyano, amino, mercapto
Base, halogen atom, phenyl, tolyl, naphthalene, furyl, thienyl, pyrrole radicals, pyridyl group, pyranose, quinolyl, indoles
One of base, carboxylic acid or carboxylic acid derivates, carbazyl or anilino-, the carbon atom number of alkyl and alkoxy is respectively 1~12；
In above compound structural formula, wherein R1~R8、A1~A8、B1~B8And the preferred structure of R can be in the following figure
One of shown 29 kinds or hydrogen atom:
-CH3、
The present invention also provides a kind of preparation methods of fluorenyl salicylide buzane analog derivative, include the following steps:
A, Fluorenone or fluorenone derivatives and hydrazine hydrate are heated to 20 DEG C~150 DEG C in the first reaction dissolvent, reaction 1 is small
When~24 hours, it then cools to room temperature, is precipitated crystal or powder after removing solvent, intermediate connection is obtained after being recrystallized
Hydrazine；45 DEG C~90 DEG C are wherein preferably heated to, is reacted 6 hours~12 hours, the preferred tetrahydrofuran of recrystallization solvent for use, second
Alcohol, toluene, DMF etc., most preferably ethyl alcohol；
B, intermediate buzane is heated to 20 DEG C with corresponding aryl salicylide structural compounds in the second reaction dissolvent
It~150 DEG C, reacts 1 hour~24 hours, then cools to room temperature, precipitate crystal or powder after removing solvent, chromatographed by column
Or it is recrystallized to give fluorenyl salicylide buzane analog derivative；30 DEG C~90 DEG C are wherein preferably heated to, reaction 6 hours~12 is small
When, the preferred tetrahydrofuran of recrystallization solvent for use, ethyl alcohol, toluene, DMF etc., most preferably ethyl alcohol.
In the preparation process in accordance with the present invention, the second reaction dissolvent choosing in the first reaction dissolvent and step B in step
From methanol, ethyl alcohol, acetic acid, tetrahydrofuran, toluene, benzene, chloroform, methylene chloride, n,N-Dimethylformamide (DMF), N, N- bis-
The mixing of methylacetamide (DMAC) and any one solvent or any several formation in N-Methyl pyrrolidone (NMP) is molten
Agent；First reaction dissolvent and the second reaction dissolvent are respectively preferably the mixed solvent that ethyl alcohol or ethyl alcohol and other solvents are formed.
Fluorenyl salicylide buzane analog derivative of the invention can be used as the fluorescence for preparing the dyeing of cell internal specific fat drips
The application of probe, the fluorescence probe are mainly used in vivo, in vitro and in ocean in terms of unicellular lower eukaryote determination of fat
And studied for pathology and curative effect of medication etc..
Implement fluorenyl salicylide buzane analog derivative and its preparation method and application of the invention, has below beneficial to effect
Fruit: such compound can be freed in and out and is enriched at the fat drips in the cell of cell and specificity, be become from original unstressed configuration
Intense fluorescence, while biggish Stokes position is presented under the action of Excited state proton trans fer mechanism (ESIPT) in the molecule
It moves, shows as yellow, orange red or red fluorescence is not displaced substantially compared with the solid state fluorescence of in vitro, it can be accurate
Probe localized sites are judged, so that the monitoring to cell fat drips structure, behavior and physiology course is realized, in biology, medical treatment, health
And energy field, there is extremely wide application prospect.
Specifically:
(1) it selects buzane structure as conjugated bridge symbasis member, on the one hand keeps probe point using single alternate form of double bond
The lone pair electrons of the conjugated degree of son, another aspect N atom have lesser steric hindrance, can to a certain extent certainly
By rotating from spatial volume is adjusted, guarantees that it can be easy to be directed through cell membrane, intracellular substructure is selected；
(2) five-membered ring structure that fluorenyl is introduced in peripheral conjugated structure, increases its electron-withdrawing ability, expand spectrum to
The longer direction of wavelength is mobile, to be applied to In vivo detection；
(3) phenolic hydroxyl structure is introduced at buzane both ends, forms ESIPT state (intramolecular under excitation state with the lone pair electrons of N
Proton translocation), effectively increase Stokes shift, prevent the self-absorption phenomenon of molecule, and assigns molecule significant AIE
Energy；The water solubility of phenolic hydroxyl group also can significantly adjust the lipid of molecule, so that increasing probe is directed through cell
Probability；
(4) since the unique rigid structure of molecule causes fluorescence of the fluorescence probe in fat drips similar to solid, just
It is pointed out and quantitative analysis in being realized in complex system.
Detailed description of the invention
Figure 1A is solvation effect and aggregation-induced emission effect of the fluorenyl salicylide buzane (FAS) in different solvents；
Figure 1B is solvation effect and aggregation-induced emission effect of the FAS in the tetrahydrofuran solution of different moisture content；
Fig. 2A is the photograph via bright field of FAS cell dyeing；
Fig. 2 B is the fluorescence photo of FAS cell dyeing；
Fig. 3 is FAS concentration optimization experiment photo in fluorescent staining in Hela cell；
Fig. 4 is time-optimized experiment photo of the FAS in Hela cell in fluorescent staining under prescribed concentration.
Specific embodiment
With reference to the accompanying drawings and examples, to fluorenyl salicylide buzane analog derivative of the invention and preparation method thereof and answering
With being described further:
The present invention provides a kind of fluorenyl salicylide buzane analog derivative, and general structure is as follows:
Wherein Ar indicates aromatic group or its derivative structure, substituent R1~R8It is respectively selected from hydrogen, alkyl, hydroxyl, alcoxyl
Base, nitro, cyano, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthalene, furyl, thienyl, pyrrole radicals, pyridyl group,
One of pyranose, quinolyl, indyl, carboxylic acid or carboxylic acid derivates, carbazyl or anilino-, the carbon of alkyl and alkoxy
Atomicity is respectively 1~12.
Specific synthesis process:
(1)
The fluorenone derivatives with substituent structure are prepared in Fluorenone structure.
(2)
Fluorenone or the product fluorenone derivatives of step (1) are prepared important intermediate using solvent appropriate and temperature to produce
Object fluorenyl buzane.
Concrete operations: suitable Fluorenone or fluorenone derivatives and hydrazine hydrate are heated to appropriate temperature in the first reaction dissolvent
Degree is cooled to room temperature after reacting a period of time, precipitates crystal after getting rid of most of solvent or powder, obtains after recrystallization
Mesosome buzane, yield > 90%, purity > 95%.Wherein, the first reaction dissolvent is preferably selected from methanol, ethyl alcohol, acetic acid, tetrahydro furan
It mutters, toluene, benzene, chloroform, methylene chloride, n,N-Dimethylformamide (DMF), n,N-dimethylacetamide (DMAC) and N- methyl
The mixed solvent that one or more of pyrrolidones (NMP) is formed, most preferred ethanol and its mixed system with other solvents；
Preferably 20 DEG C to 150 DEG C of the proper temperature being heated to, wherein most preferably 45 DEG C to 90 DEG C；Reaction time preferably 1 hour to 24
Hour, wherein most preferably 6 hours to 12 hours；The preferred tetrahydrofuran of solvent for use, ethyl alcohol, toluene, DMF etc. are recrystallized, it is optimal
Select ethyl alcohol.
(3)
By intermediate buzane obtained in step (2), i.e. fluorenyl hydrazine hydrate, with corresponding aryl salicylide structural response system
Standby target compound.
Concrete operations: suitable intermediate buzane is heated in the second reaction dissolvent with corresponding aryl bigcatkin willow aldehyde structure
To proper temperature, be cooled to room temperature, precipitated crystal after disposing most of solvent or powder after reacting a period of time, column chromatography or
Target product is obtained after recrystallization.Wherein, the second reaction dissolvent be preferably selected from methanol, ethyl alcohol, acetic acid, tetrahydrofuran, toluene,
Benzene, chloroform, methylene chloride, n,N-Dimethylformamide (DMF), n,N-dimethylacetamide (DMAC) and N-Methyl pyrrolidone
One or more of (NMP) mixed solvent formed, most preferred ethanol and its mixed system with other solvents；It is heated to
Preferably 20 DEG C to 150 DEG C of proper temperature, wherein most preferably 30 DEG C to 90 DEG C；Reaction time preferably 1 hour to 24 hours, wherein
Most preferably 6 hours to 12 hours；Recrystallize the preferred tetrahydrofuran of solvent for use, ethyl alcohol, toluene, DMF etc., most preferred ethanol.
Embodiment 1: the synthesis (FAS) of fluorenyl salicylide buzane
10g Fluorenone and 20ml hydrazine hydrate (85%) are flowed back 4h at 100ml, there are a large amount of needle-like solids to be precipitated after cooling,
It is used ethyl alcohol recrystallization 2 times after filtering, obtains faint yellow needle dress crystal, purity 99%, yield 95%；Take 2g hydrazine hydrate crystal with
2ml salicylide flows back 4h in 20ml ethyl alcohol, faint yellow needle dress crystal is obtained after cooling, after filtering, with 75% ethanol solution
Cleaning, obtains FAS structure, yield 99%.MALDI-TOF(m/z):[M+]calcd.C20H14N2O,298.34；found,
299.34.Anal Calc.for C20H14N2O:C,80.52；H,4.73；N,9.39；O,5.36.Found:C,80.62；H,
4.71；N,9.19；O,5.36.
The synthesis (1) of embodiment 2:FAS derivative
Take 500mg hydrazine hydrate crystal and it is equimolar between hydroxyl salicylide (or bromo salicylide) derivative in 10ml second
60 DEG C of reaction 4h in alcohol obtain light yellow crystal after cooling, after filtering, are cleaned with 75% ethanol solution, obtain product chromatography
Obtain corresponding FAS derivative structure, yield > 90%.
M-FAS-OH:MALDI-TOF (m/z): [M+] calcd.C20H14N2O2,314.34；found,315.24.Anal
Calc.for C20H14N2O2:C,76.42；H,4.49；N,8.91；O,10.18.Found:C,75.32；H,4.48；N,8.35；
O,10.09。
P-FAS-Br:MALDI-TOF (m/z): [M+] calcd.C20H13BrN2O,377.23；found,299.34.Anal
Calc.for C20H13BrN2O:C,63.68；H,3.47；Br,21.18；N,7.43；O,4.24.Found:C,63.58；H,
3.40；N,7.42；O,4.19.
The synthesis (2) of embodiment 3:FAS derivative
Take 500mg hydrazine hydrate crystal and equimolar N, the 60 DEG C of reactions in 10ml ethyl alcohol of N- diethylamino salicylide
4h obtains red oil after cooling, after filtering, is cleaned with 75% ethanol solution, obtain product and chromatograph to obtain corresponding FAS
Derivative structure, yield 85%.
P-FAS-N22:MALDI-TOF (m/z): [M+] calcd.C24H23N3O:369.18；found,370.66；Anal
Calc.for C24H23N3O:C,78.02；H,6.27；N,11.37；O,4.33.found,C,77.93；H,6.10；N,11.25；
O,4.45。
Embodiment 4: fluorenyl-tetraphenyl ethylene class salicylide buzane preparation (TPE-FAS)
It is coupled after obtaining tetraphenyl ethylene base salicylaldehyde derivatives structure using Sizuki, takes 500mg hydrazine hydrate crystal therewith
60 DEG C of reaction 4h in 10ml ethyl alcohol obtain pale yellow powder after cooling, after filtering, are cleaned, obtained with 75% ethanol solution
Product chromatographs to obtain corresponding FAS derivative structure, yield 85%.
m-TPE-FAS:MALDI-TOF(m/z):[M+]calcd.C40H28N2O:552.22；found,553.28；Anal
Calc.for C40H28N2O:C,86.93；H,5.11；N,5.07；O,2.89；found,C,86.87；H,5.01；N,5.08；O,
2.79。
Embodiment 5: the optical property of fluorenyl salicylide buzane FAS and its in the application in terms of fat drips dye
(a) the basic optical property of FAS: being as shown in Figure 1A fluorescence spectrum of the FAS under opposed polarity, with polar
Significant change occurs for the ratio of variation, the alcohol of formula transmitting (near 450nm) of FAS and keto-acid transmitting (near 600nm), is typical
ESIPT transmitting.And for ESIPT molecule, state of aggregation is mostly keto-acid transmitting, is shone now so we have detected the aggregation at this
As.As shown in Figure 1B, into the tetrahydrofuran solvent of FAS, (dissolution single molecule level) is continuously added a certain proportion of water, FAS due to
Solubility is slowly gathered into nano particle, and fluorescence intensity is remarkably reinforced (near 600nm), is called AIE property.FAS tool
There is apparent ESIPT and AIE property, the potential quality with fluorescence probe.
(b) cell dyeing is tested: by FAS to be instilled in cell culture fluid after certain concentration solution DMSO solution, selection
Hela cell is observed its polarity using fluorescence microscope after cultivating a period of time, discovery FAS can be smooth as research object
Penetrate cell wall, and orient at cell fat drips be enriched with, to show Chinese red fluorescence (near 600nm).
Fig. 2A is photo of the Hela cell in light field, wherein crusty pancake bag-like is the fat drips structure of cell；Fig. 2 B is after dyeing
Fluorescence photo of the cell under the dark field of 330nm-385nm exciting light, the two comparison display, FAS be capable of specificity to thin
Born of the same parents' fat drips dye, and its Fluorescent peal and solid state fluorescence spectrum no significant difference.Illustrate that FAS can be without any modification
It is directly entered cell and realizes targeting fluorescent staining, do not show apparent fluorescence shift, AIE and ESIPT phenomenon has obtained very
Good utilization.
(c) optimization of fat drips Coloration experiment condition: as shown in Figure 3 and Figure 4, we have carried out dyeing concentration and time excellent
Change, discovery FAS concentration is at 7.5 μM, and when dyeing time is 30min, the effect of cell fluorescence fat drips imaging is best.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention
It should be understood that for those of ordinary skills, it can be modified or changed according to the above description,
All improvement or transformation belong within the protection scope of appended claims of the present invention.
Claims (1)
1. a kind of fluorenyl salicylide buzane analog derivative is in the application for the fluorescence probe for preparing the dyeing of cell internal specific fat drips, institute
State the compound that fluorenyl salicylide buzane analog derivative is following any structure formula:
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2691642A (en) * | 1951-05-15 | 1954-10-12 | Distillers Co Yeast Ltd | Stabilized polyvinylidene chloride compositions containing fluorenone azines |
| US4415640A (en) * | 1981-02-19 | 1983-11-15 | Konishiroku Photo Industry Co., Ltd. | Electrophotographic element with fluorenylidene hydrazone compounds |
| WO1999040062A1 (en) * | 1998-02-05 | 1999-08-12 | Novo Nordisk A/S | Hydrazone derivatives |
| CN1577115A (en) * | 2003-06-30 | 2005-02-09 | 三星电子株式会社 | Azine-based dimeric charge transport materials |
-
2015
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2691642A (en) * | 1951-05-15 | 1954-10-12 | Distillers Co Yeast Ltd | Stabilized polyvinylidene chloride compositions containing fluorenone azines |
| US4415640A (en) * | 1981-02-19 | 1983-11-15 | Konishiroku Photo Industry Co., Ltd. | Electrophotographic element with fluorenylidene hydrazone compounds |
| WO1999040062A1 (en) * | 1998-02-05 | 1999-08-12 | Novo Nordisk A/S | Hydrazone derivatives |
| CN1577115A (en) * | 2003-06-30 | 2005-02-09 | 三星电子株式会社 | Azine-based dimeric charge transport materials |
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