CN105670608B - High-selectivity fluorescent probe capable of detecting nickel ions in mitochondria of living cells and preparation method thereof - Google Patents
High-selectivity fluorescent probe capable of detecting nickel ions in mitochondria of living cells and preparation method thereof Download PDFInfo
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- CN105670608B CN105670608B CN201610100192.2A CN201610100192A CN105670608B CN 105670608 B CN105670608 B CN 105670608B CN 201610100192 A CN201610100192 A CN 201610100192A CN 105670608 B CN105670608 B CN 105670608B
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- 238000002360 preparation method Methods 0.000 title claims abstract description 38
- 210000003470 mitochondria Anatomy 0.000 title claims abstract description 21
- 229910001453 nickel ion Inorganic materials 0.000 title claims abstract description 21
- 210000004027 cell Anatomy 0.000 title abstract description 34
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 title abstract description 5
- 239000007850 fluorescent dye Substances 0.000 title abstract 2
- 239000000523 sample Substances 0.000 claims abstract description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 13
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims abstract description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract 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 claims abstract description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 6
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 29
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 18
- 238000000967 suction filtration Methods 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 235000019441 ethanol Nutrition 0.000 claims description 11
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 claims description 11
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical class BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 5
- 229910019213 POCl3 Inorganic materials 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000008267 milk Substances 0.000 claims description 4
- 210000004080 milk Anatomy 0.000 claims description 4
- 235000013336 milk Nutrition 0.000 claims description 4
- 239000004570 mortar (masonry) Substances 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical class O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims description 3
- 241000555268 Dendroides Species 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 28
- 238000003384 imaging method Methods 0.000 abstract description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract description 4
- 230000009471 action Effects 0.000 abstract description 3
- 239000011368 organic material Substances 0.000 abstract description 3
- 238000006482 condensation reaction Methods 0.000 abstract description 2
- 238000013461 design Methods 0.000 abstract description 2
- 239000000975 dye Substances 0.000 abstract description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000011160 research Methods 0.000 abstract description 2
- 239000002262 Schiff base Substances 0.000 abstract 2
- 150000004753 Schiff bases Chemical class 0.000 abstract 2
- 210000000805 cytoplasm Anatomy 0.000 abstract 1
- 150000003003 phosphines Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 239000006059 cover glass Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000002438 mitochondrial effect Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- -1 Triphenylamine nitro-derivative Chemical class 0.000 description 2
- 239000006143 cell culture medium Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- SGBQQAKHPHSBJJ-UHFFFAOYSA-N CC1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[N+](=O)([O-])C1=CC=CC=C1 Chemical compound CC1=C(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[N+](=O)([O-])C1=CC=CC=C1 SGBQQAKHPHSBJJ-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- CVRXLMUYFMERMJ-UHFFFAOYSA-N N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine Chemical compound C=1C=CC=NC=1CN(CC=1N=CC=CC=1)CCN(CC=1N=CC=CC=1)CC1=CC=CC=N1 CVRXLMUYFMERMJ-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005415 bioluminescence Methods 0.000 description 1
- 230000029918 bioluminescence Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000013500 data storage Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
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- 239000001963 growth medium Substances 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000008611 intercellular interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 210000001082 somatic cell Anatomy 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
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- 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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
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- 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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- 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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- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
A high-selectivity fluorescent probe capable of detecting nickel ions in mitochondria of living cells and a preparation method thereof are disclosed, wherein the probe is a pyridyltrisinylamine derivative, triphenylamine is used as an initial raw material, phosphine salt of intermediate I4- (N, N-diphenylamino) benzaldehyde and intermediate II p-nitrotoluene is prepared, then 4-p-nitrovinyl triphenylamine intermediate is prepared from the intermediates 1 and II, 4-p-aminostyryl triphenylamine is obtained by reduction under the action of Pd/C and hydrazine hydrate, Schiff base is obtained by condensation reaction with 2-pyridine benzaldehyde, and the Schiff base is reduced under the action of sodium borohydride to obtain a target product. The probe has good single photon fluorescence property at about 425 nm. After the HepG2 cells were stained with the target product, it could be clearly observed that the organic material had high imaging ability for mitochondria in the cytoplasm of HepG2 cells and could reversibly detect nickel ions in mitochondria. The probe has great significance for the design, preparation and life science research of organic dyes.
Description
First, technical field
It is specifically a kind of that there is hypotoxicity, energy the present invention relates to a kind of one-photon optical material and preparation method thereof
There is pyridine radicals triphen amine fluorescence probe of recognition capability and preparation method thereof to the nickel ion in living cells mitochondria.
2nd, background technology
The functional study of cell and gene is carried out using living cells imaging workstation, be biomedical research it is newest become
Gesture.Fixed cell observation is only capable of providing the static information of fixed moment cell, it is impossible to reflect cell in normal physiological biochemical condition
Under the observation of state living cells, whole scanning and record are carried out to the cell under normal physiological condition, it is obtained continuous, complete
Face, dynamic process.Due to the dynamic active procedure of normal cell of its display, it is easy to find and determine cell-cell interaction
With the interaction between the process of signal transduction, and biomolecule in living cells level, can not only solve for a long time with
The problem of not solved to hang, it is more following the problem of researching and proposing new, it is indicated that new direction.
Chemical Luminescent Probes show preferable selectivity in the identification process to object, thus, in environmental monitoring, divide
The exhibition of the field such as muonic catalysis and bioluminescence imaging has potential application value, receives significant attention.With traditional detection method
(such as atomic absorption spectrum and plasma emission spectrum, electrochemical process, colorimetric method, biology and nano-sensor) is compared, chemistry
Fluorescence probe is mainly using the fluorescence signal change (enhancing, decrease or launch wavelength displacement etc.) occurred in test process to object
Detected there is that low with low cost, simple to operate, test limit, sensitivity and selectivity are high.Living cells imaging technique
These fluorescence probes are exactly utilized, such as small molecule organic dyestuff or quantum dot carry out specific mark molecule interested.
Triphenylamine is the compound with hub-and-spoke configuration centered on nitrogen-atoms.Because it has unique free mafic
Matter, larger steric hindrance, hyperconjugation electronic effect and higher hole mobility, thus in photoelectric material and hole transport
The fields such as material have a wide range of applications.In addition, the phenyl ring of the lone pair electrons and surrounding on N atoms forms big conjugated system,
So that the launch wavelength of molecule is located at blue green light region, good optical characteristics is shown, three-dimensional optical is widely used in
The fields such as data storage, fluorescence probe and cell imaging.
3rd, the content of the invention
The present invention is intended to provide it is a kind of have in detectable living cells mitochondria the high selectivity fluorescence probe of nickel ion and
Its preparation method, synthesized probe is the amine derivant of triphenylamine base containing pyridine radicals, and the probe possesses hypotoxicity and good
Optical property, can be in cell mitochondrial image areas, and has reversible detectivity to nickel ion.
A kind of claimed high selectivity fluorescence probe with nickel ion in detectable living cells mitochondria of the present invention,
Its structural formula is as follows：
The preparation method of above-mentioned high selectivity fluorescence probe is claimed in the present invention simultaneously, and the preparation method step is such as
Under：
A, intermediate I preparation
DMF, POCl3 and triphenylamine are sequentially added under ice bath into container, 40-70 DEG C is then heated to, 14- is reacted
18h, the reaction solution separating, washing and dry faint yellow intermediate I；
B, intermediate II preparation
Nitrotoleune and N- bromo-succinimides (NBS) are dissolved in benzene, in catalyst benzoyl peroxide (BPO)
Under effect, 7-10h is reacted at 60-100 DEG C, reaction is cooled to room temperature after terminating, filters and retain filtered fluid, then to filtering
Triphenylphosphine is added in liquid, 2-5h is reacted at 40-80 DEG C, reaction naturally cools to room temperature, filtering, washing and vacuum after terminating
Yellow intermediate II is obtained after drying；
C, intermediate III preparation
T-BuOK, intermediate I and intermediate II are ground in mortar, after reaction completely, CH is used2Cl2Reactant is molten
Solution, is filtered, concentration, obtains the red intermediate III of dendroid；
D, intermediate IV preparation
By in the molten ethanol solution of intermediate III, hydrazine hydrate is then added, in the presence of catalyst Pd/C, at 50-80 DEG C
Lower back flow reaction 1-3h, after reaction completely, suction filtration, obtains milk yellow intermediate IV while hot.
E, intermediate V preparation
The intermediate IV being dissolved in methanol solution is warming up to 50-80 DEG C, then adds glacial acetic acid, adds 2- pyridines
Formaldehyde, back flow reaction 4-6h, after reaction terminates, suction filtration obtains yellow powder intermediate V.
F, target product L preparation
Added into reaction vessel at sodium borohydride, the intermediate V of dissolving in ethanol, 10-40 DEG C and react 0.5-2h
Afterwards, suction filtration, ethyl alcohol recrystallization obtains brown target product L solids.
Preferably, in the step A, DMF, POCl3 and triphenylamine mole dosage ratio are 1:1:1.
Preferably, in the step B, para-nitrotoluene, N- bromo-succinimides (NBS), triphenylphosphine mole with
Amount is than being 1：12：12.
Preferably, in the step C, t-BuOK, intermediate I and intermediate II mole dosage ratio are 5.4：1.8：
2.2。
Preferably, in the step D, intermediate III, the mole dosage ratio of hydrazine hydrate are 1：10.
Preferably, in the step E, intermediate IV, 2- pyridine carboxaldehydes mole dosage ratio are 7.2：9.4.
Preferably, in the step F, sodium borohydride, the mole dosage ratio of intermediate V are 2：1.
Compared with the prior art, beneficial effects of the present invention are embodied in：
1st, the present invention is succinct high using the trianilino group with compared with high reaction activity and good biocompatibility as main body
Triphenylamine nitro-derivative is prepared for effect, by reduction reaction, condensation reaction, pyridine radicals triphen amine fluorescence probe is obtained,
Found through experiment, pyridine radicals triphen amine fluorescence probe prepared by the present invention has good single photon fluorescence in 425nm or so
Property (Fig. 2).After HepG2 cells are dyed by target product, organic material can be clearly observed in HepG2 cell matter
Mitochondria there is high imaging capability, and the reversibly nickel ion in detection mitochondria.Probe of the present invention is for there is engine dyeing
Design, preparation and the life science of material are significant.
2nd, the pyridine radicals triphen amine fluorescence probe that the present invention is synthesized is that a class has cytoplasm Mitochondria imaging function
One-photon optical material.To cell not damaged, available for active somatic cell detection, with obvious application value；
3rd, preparation method raw material of the present invention is easy to get, and cost is low, and synthesis step is simple, it is easy to operate.
4th, illustrate
Fig. 1 is preparation method route map of the invention.
Fig. 2 be the present invention pyridine radicals triphen amine fluorescence probe in acetonitrile under excitation wavelength 368nm to different metal
The fluorescence response figure of ion.
Fig. 3 a-3c be pyridine radicals triphen amine fluorescence probe to HepG2 cell fluorescence confocal microscopic image figures,
Wherein Fig. 3 a are the fluorescence co-focusing microphotos of the HepG2 cells of pyridine radicals triphen amine fluorescence probe coloring；
Fig. 3 b are light field action diagrams；Fig. 3 c are the photos of overlapping.
Fig. 4 a are that pyridine radicals triphen amine fluorescence probe and mitochondrial commodity coloring agent Mito-Tracker are thin to HepG2
Born of the same parents' fluorescence co-focusing micro-imaging figure.The picture left above is probe to HepG2 cell fluorescence confocal microscopic images in Fig. 4 a；Top right plot
It is commodity coloring agent Mito-Tracker to HepG2 cell fluorescence confocal microscopic images；Lower-left figure is to HepG2 cell fluorescences
The light field figure of confocal microscopic image；Bottom-right graph is pyridine radicals triphen amine fluorescence probe and mitochondrial commodity coloring agent
Details in a play not acted out on stage, but told through dialogues stacking charts of the Mito-Tracker to HepG2 cell fluorescence confocal microscopic images.
Fig. 4 b are the Pierres between pyridine radicals triphen amine fluorescence probe and mitochondrial commodity coloring agent Mito-Tracker
Gloomy coefficient correlation.
5th, embodiment
Explanation is further explained to technical solution of the present invention by specific embodiment below in conjunction with accompanying drawing.
1st, the preparation of intermediate I
Add in 7.4mL (0.1mol) DMF, ice-water bath and stir in 250mL flasks, 9.2mL is then added dropwise
(0.1mol) POCl3, continues to stir, liquid becomes sticky in bottle after 15min, finally obtains white reddish solid and freezes
Salt.The 100ml chloroformic solutions for containing 24.5g (0.1mol) triphenylamine are added in above-mentioned flask, temperature are risen to 50 DEG C of about 30min
To freezing, salt is entirely molten, and back flow reaction 16h at 65 DEG C, thin-layered chromatography has rotated chloroform after judging reaction completely, and residue is poured into
In 1000mL cold water, solution ph is adjusted to alkalescent with potassium carbonate, there are a large amount of greenish yellow solids to separate out, suction filtration is spin-dried for solvent,
Residue is through chromatographic column separating-purifying, and eluant, eluent is pure petroleum ether, obtains 7.81g products, yield 71.5%.1H NMR:
(DMSO-d6,400Hz),δ(ppm):6.89 (d, J=8.80Hz, 2H), 7.23 (q, 6H), 7.42 (t, J=7.80Hz, 4H),
7.72 (d, J=8.80Hz, 2H), 9.771 (s, 1H).
2nd, the preparation of intermediate II
In 500mL round-bottomed flask, 13.7g (0.1mol) para-nitrotoluene, 21.4g (0.12mol) N- are separately added into
Bromo-succinimide (NBS) is dissolved in 150mL benzene, is eventually adding 0.5g benzoyl peroxides (BPO) catalyst, is warming up to
Back flow reaction 8h at 80 DEG C, thin-layered chromatography is judged after reaction completely, is cooled to room temperature, there is white solid (succinimide) analysis
Go out, suction filtration, filter off and back flow reaction 3 hours at 31.5g (0.12mol) triphenylphosphine, 50 DEG C are added in white solid, filtrate；It is cold
But substantial amounts of solid separates out to room temperature, suction filtration, solid is washed three times with benzene (5mL), obtains 39.0g yellow solids.Yield is
81.6%.1H NMR:((CD3)2CO,400Hz),δ(ppm):5.98 (d, J=8.00,2H), 7.47 (d, J=8.40Hz, 2H),
7.57-7.62 (m, 6H), 7.75 (t, J=7.60Hz, 3H), 7.82 (q, 8H).
3rd, the preparation of intermediate III
0.6g (5.4mmol) t-BuOK (potassium tert-butoxide) is pulverized in mortar, 1.0g (2.2mmol) is then added
After bromination (4- nitrobenzene methyl) triphenylphosphine (intermediate II), grinding 5min, 0.5g (1.8mmol) 4- (N, N- bis- is separately added
Phenyl amino) benzaldehyde (intermediate I) add mortar in, grinding, thin-layered chromatography judge reaction completely after.Use CH2Cl2By its
Dissolving, filtering, filtrate washing, anhydrous MgsO4G is dried, and concentration, absolute ethyl alcohol recrystallizes to obtain 0.33g dendroid red solids.Production
Rate is：46.5%.1H NMR:((CD3)2CO,400Hz),δ(ppm):7.03 (d, J=8.00Hz, 2H), 7.13 (d, J=
7.20Hz, 6H), 7.38 (d, J=16.40,1H), 7.35 (d, J=7.80Hz, 4H), 7.51 (d, J=16.40Hz, 1H),
7.60 (d, J=8.00Hz, 2H), 7.85 (d, J=8.40Hz, 2H), 8.23 (d, J=8.00Hz, 2H).
4th, the preparation of intermediate IV
3.0g (10mmol) intermediate III and 150mL alcohol solvent are added in 250mL two neck round-bottom flasks, is warming up to
At 80 DEG C, 0.3g Pd/C catalyst is added, and the ethanol solution that 10mL contains 4.9mL 85% (v/v) hydrazine hydrate, drop are added dropwise dropwise
Add after finishing, continue back flow reaction 2 hours, thin-layered chromatography is judged after reaction completely.Have substantial amounts of solid in suction filtration while hot, filtrate
Body is separated out, and suction filtration obtains milk yellow solid, then screws out ethanol in filtrate, and cooling has a large amount of solids to separate out, again suction filtration, twice
The product of suction filtration merges, vacuum drying, and 2.56g milk yellow solids are obtained.Yield is 70.7%.1H NMR:((CD3)2CO,
400Hz),δ(ppm):4.782 (s, 2H), 6.68 (d, J=8.40Hz, 2H), 6.93 (d, J=16.40Hz, 1H), 7.09-
7.00 (m, 10H), 7.33-7.29 (m, 6H), 7.45 (d, J=8.80Hz, 2H) .MS (EI), m/z (%):362.18([M]+,
100)。
5th, the preparation of intermediate V
Intermediate IV (2.6g, 7.2mmol) is dissolved in 120mL methanol in 250mL round-bottomed flasks, 70 DEG C are warming up to, returned
Flow down addition 3 drip glacial acetic acids (catalyst), then be added dropwise at 2- pyridine carboxaldehydes (1.0g, 9.4mmol), 70 DEG C react 5 hours,
No longer separated out to solid, suction filtration, be dried in vacuo, obtain 3.1g yellow powders (yield 88.4%).
m.p.189℃.1H NMR:(DMSO-d6,400Hz),δ(ppm):6.97 (d, J=8.0Hz, 3H), 7.03-7.07
(m, 6H), 7.19 (d, J=12.0Hz, 2H), 7.28-7.35 (m, 6H), 7.51-7.53 (m, 5H), 7.63 (d, J=8.0Hz,
2H), 7.95 (t, J=8.0Hz, 2H), 8.68 (s, 1H)；13C NMR(100MHz,DMSO-d6,TMS,ppm):δ160.02,
151.13,147.89,147.78,136.67,136.14,131.89,131.78,129.67,129.22,128.14,127.70,
127.50,126.72,124.93,123.78,123.45,121.81；MALDI-TOF m/z:Calculated value, 450.210；Experiment
Value, 449.890.
6th, target product L preparation
Sodium borohydride (0.005g, 0.14mmol) (is averagely added, gently in four times in batches in 100mL round-bottomed flasks
Reaction speed) it is added in ethanol solutions of the 25mL containing 0.15g (0.07mmol) intermediate V.Stirring reaction 1 hour, has at room temperature
Brown solid is gradually separated out, and after TLC point plates spike reaction completely, suction filtration, obtained solid ethyl alcohol recrystallization obtains 0.10 gram
Brown solid (yield 77.1%).1H NMR(400MHz,DMSO-d6),δ(ppm):8.54 (J=4, s, 1H), 7.70 (J=8,
T, 1H), 7.40 (J=8, d, 2H), 7.35 (J=8, d, 1H), 7.24-7.32 (m, 7H), 7.00-7.06 (m, 6H), 6.94 (J
=8, t, 3H), 6.80 (J=20, d, 1H), 4.30 (J=4, d, 2H)13C NMR(100MHz,DMSO-d6),δ(ppm):
159.28,148.89,148.76,147.88,146.94,145.29,136.40,130.28,127.62,127.38,126.82,
125.34,123.72,123.63,122.88,122.64,121.98,121.08,112.37,48.74.MS(APCI):Theoretical value
453.22；Experiment value, 454.2283.
7th, identifications of the target product L to nickel ion
It is one of most important feature of fluorescence probe that selective row, which is,.As shown in Fig. 2 when being excited with 368nm, fluorescence
Intensity is strong.When adding extensive environment and physiologically important metal ion with target product L equal quantities, such as：Cu2+,
Hg2+,Zn2+,Ni2+,Mg2+,Pb2+,Ca2+,Cd2+,Ag+,Fe3+,Al3+,Mn2+,Co2+,Cr3+,Li+,K+,Na+,La+,Ba2+When,
At room temperature, fluorescence intensities of the target product L in acetonitrile for adding nickel ion declines 14 times, other metal ions without obvious
Fluorescence intensity change.Interference test shows that jamming target product L is not recognized other each metal ion species to nickel ion.We
Target product L is have detected in acetonitrile with (2- pyridylmethyls) ethylenediamine of nickel ion chelating agent N, N, N', N'- tetra- (TPEN)
Recognize Ni2+Invertibity, as a result display target product L there is the recognition capability of good circulation.
8th, the test of target product L single photons cell developing effect
The cover glass for cleaning up and sterilizing is put into 6 hole tissue culturing plates, liver cancer tissue cell (HepG2 cells) 5
×105The density in individual/hole is seeded in diameter 35mm 6 orifice plate culture dishes, and carries out cell as cell culture medium with DMEM
Contain hyclone (10%), penicillin (100 μ g/mL) and streptomysin (100ug/mL) in culture, cell culture medium.Cell is trained
Foster ware is placed in containing 5%CO2And 95%O2Incubator in maintain 37 DEG C of temperature progress cell culture 24h, with PBS (phosphoric acid buffers
Liquid, pH=7.4, the production of Gibco Reagent Companies) wash HepG2 cells three times, wash away culture medium.It is then respectively adding 4 μ L targets
Compound A or B DMSO solution (1mM), cultivate 0.5h, and cover glass is rinsed 6~7 times with PBS cushioning liquid (pH=7.4), drop
4% paraformaldehydes of 1mL/PBS solution fixes cell 10min, distilled water flushing cover glass 6~7 times.Cover glass is stuck in cleaning
On slide, observation cellular morphology and fluorescence intake feelings under laser confocal microscope (LSM-710, Zeiss, Germany) are placed in
Condition, is as a result shown in Fig. 3 a-3c, 4a, 4b.
From Fig. 3 a-3c, 4a, 4b it will be clear that target product L passes through the cell membrane of HepG2 cells, into thin
It is very high to the uptake ratio of target product in mitochondria in kytoplasm, and to the coloring of its substantially uniformity, illustrate target product pair
HepG2 mitochondria has very high recognition capability.The preparation of this organic material for the selecting of cell developing material, make
It is standby, for suffering from important meaning in terms of life science, material science.
Claims (8)
1. the high selectivity fluorescence probe of nickel ion in a kind of detectable living cells mitochondria, it is characterised in that：The high selection
The structural formula of property fluorescence probe is：
2. the preparation of the high selectivity fluorescence probe of nickel ion in a kind of detectable living cells mitochondria as claimed in claim 1
Method, it is characterised in that operate according to the following steps：
A, intermediate I preparation
DMF, POCl3 and triphenylamine are sequentially added under ice bath into container, 40-70 DEG C is then heated to, 14-18h is reacted,
The reaction solution separating, washing and dry faint yellow intermediate I, the intermediate I chemical formula is：
B, intermediate II preparation
Para-nitrotoluene and N- bromo-succinimides (NBS) are dissolved in benzene, in catalyst benzoyl peroxide (BPO) work
Under, 7-10h is reacted at 60-100 DEG C, reaction is cooled to room temperature after terminating, filters and retain filtered fluid, then to filtered fluid
Middle addition triphenylphosphine, reacts 2-5h at 40-80 DEG C, and reaction naturally cools to room temperature after terminating, filtering, washing and vacuum are done
Yellow intermediate II is obtained after dry, the intermediate II chemical formula is：
C, intermediate III preparation
T-BuOK, intermediate I and intermediate II are ground in mortar, after reaction completely, CH is used2Cl2Reactant is dissolved, mistake
Filter, concentration obtains the red intermediate III of dendroid, and the chemical formula of intermediate III is：
D, intermediate IV preparation
By in the molten ethanol solution of intermediate III, hydrazine hydrate is then added, in the presence of catalyst Pd/C, at 50-80 DEG C next time
Stream reaction 1-3h, after reaction completely, suction filtration, obtains milk yellow intermediate IV while hot；The chemical formula of intermediate IV is：
E, intermediate V preparation
The intermediate IV being dissolved in methanol solution is warming up to 50-80 DEG C, then adds glacial acetic acid, adds 2- pyridine first
Aldehyde, back flow reaction 4-6h, after reaction terminates, suction filtration obtains yellow powder intermediate V；The chemical formula of intermediate V is：
F, target product L preparation
Add and reacted at sodium borohydride, the intermediate V of dissolving in ethanol, 10-40 DEG C after 0.5-2h into reaction vessel, taken out
Filter, ethyl alcohol recrystallization obtains brown target product L solids；The target product L Solid-state Chemistry formulas are：
That is fluorescence probe.
3. the system of the high selectivity fluorescence probe of nickel ion in a kind of detectable living cells mitochondria according to claim 2
Preparation Method, it is characterised in that in the step A, DMF, POCl3 and triphenylamine mole dosage ratio are 1:1:1.
4. the system of the high selectivity fluorescence probe of nickel ion in a kind of detectable living cells mitochondria according to claim 2
Preparation Method, it is characterised in that in the step B, para-nitrotoluene, N- bromo-succinimides (NBS), triphenylphosphine mole with
Amount is than being 1：12：12.
5. the system of the high selectivity fluorescence probe of nickel ion in a kind of detectable living cells mitochondria according to claim 2
Preparation Method, it is characterised in that in the step C, t-BuOK, intermediate I and intermediate II mole dosage ratio are 5.4：1.8：
2.2。
6. the system of the high selectivity fluorescence probe of nickel ion in a kind of detectable living cells mitochondria according to claim 2
Preparation Method, it is characterised in that in the step D, intermediate III, the mole dosage ratio of hydrazine hydrate are 1：10.
7. the system of the high selectivity fluorescence probe of nickel ion in a kind of detectable living cells mitochondria according to claim 2
Preparation Method, it is characterised in that in the step E, intermediate IV, 2- pyridine carboxaldehydes mole dosage ratio are 7.2：9.4.
8. the system of the high selectivity fluorescence probe of nickel ion in a kind of detectable living cells mitochondria according to claim 2
Preparation Method, it is characterised in that in the step F, sodium borohydride, the mole dosage ratio of intermediate V are 2：1.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103360782A (en) * | 2013-07-30 | 2013-10-23 | 重庆大学 | Stilbene visible photosensitizer containing amino group and hydroxyl group segments on 4-site, and synthesis |
-
2016
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN103360782A (en) * | 2013-07-30 | 2013-10-23 | 重庆大学 | Stilbene visible photosensitizer containing amino group and hydroxyl group segments on 4-site, and synthesis |
Non-Patent Citations (3)
| Title |
|---|
| Assembly, Two-Photon Absorption, and Bioimaging of Living Cells of A Cuprous Cluster;Xuchun Wang et al.;《Chem. Mater.》;20111213;第24卷;954-961 * |
| Self-assembly of metal ion induced highly emissive fluorophore-triphenylamine nanostructures: enhanced two-photon action cross-section for bioimaging applications;Lin Kong et al.;《J. Mater. Chem. C》;20141105;第3卷;570-581 * |
| Zinc(II) complex with teirpyridine derivative ligand as "on–off" type fluorescent probe for cobalt(II) and nickel(II) ions;Peng Wang et al.;《Inorganic Chemistry Communications》;20120201;第18卷;87-91 * |
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