CN107722058A - 一种有机化合物及其应用 - Google Patents
一种有机化合物及其应用 Download PDFInfo
- Publication number
- CN107722058A CN107722058A CN201711089014.5A CN201711089014A CN107722058A CN 107722058 A CN107722058 A CN 107722058A CN 201711089014 A CN201711089014 A CN 201711089014A CN 107722058 A CN107722058 A CN 107722058A
- Authority
- CN
- China
- Prior art keywords
- mao
- compound
- fluorescence
- fluorescence probe
- organic compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 20
- 102000010909 Monoamine Oxidase Human genes 0.000 claims abstract description 84
- 108010062431 Monoamine oxidase Proteins 0.000 claims abstract description 84
- 239000000523 sample Substances 0.000 claims abstract description 34
- 238000001514 detection method Methods 0.000 claims abstract description 18
- 238000012360 testing method Methods 0.000 claims abstract description 11
- 230000002438 mitochondrial effect Effects 0.000 claims abstract description 9
- 239000012528 membrane Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 35
- 230000008859 change Effects 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 7
- 238000010521 absorption reaction Methods 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 4
- 238000009825 accumulation Methods 0.000 abstract description 3
- 238000006073 displacement reaction Methods 0.000 abstract description 3
- 238000001727 in vivo Methods 0.000 abstract description 3
- 238000011835 investigation Methods 0.000 abstract description 3
- 230000007246 mechanism Effects 0.000 abstract description 3
- 230000009471 action Effects 0.000 abstract description 2
- 230000036541 health Effects 0.000 abstract description 2
- 238000011160 research Methods 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
- 210000004027 cell Anatomy 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 7
- 239000007995 HEPES buffer Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 210000003470 mitochondria Anatomy 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 239000007850 fluorescent dye Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- -1 tyrasamine Chemical compound 0.000 description 3
- 229910021642 ultra pure water Inorganic materials 0.000 description 3
- 239000012498 ultrapure water Substances 0.000 description 3
- 239000012224 working solution Substances 0.000 description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
- 102100026802 72 kDa type IV collagenase Human genes 0.000 description 2
- 101710151806 72 kDa type IV collagenase Proteins 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 108010024636 Glutathione Proteins 0.000 description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
- 102100030412 Matrix metalloproteinase-9 Human genes 0.000 description 2
- 108010015302 Matrix metalloproteinase-9 Proteins 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 2
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229960003180 glutathione Drugs 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
- 229960001763 zinc sulfate Drugs 0.000 description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 description 2
- UGDCGMGDLWXMSA-UHFFFAOYSA-N 3-methyl-6-phenyl-2,4-dihydro-1h-pyrimidine Chemical class C1N(C)CNC(C=2C=CC=CC=2)=C1 UGDCGMGDLWXMSA-UHFFFAOYSA-N 0.000 description 1
- 241001614291 Anoplistes Species 0.000 description 1
- UGAKJPMSFVMKEF-UHFFFAOYSA-N C=1C=CC=CC=1[P](C=1C=CC=CC=1)(Br)C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1[P](C=1C=CC=CC=1)(Br)C1=CC=CC=C1 UGAKJPMSFVMKEF-UHFFFAOYSA-N 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 102100027998 Macrophage metalloelastase Human genes 0.000 description 1
- 101710187853 Macrophage metalloelastase Proteins 0.000 description 1
- 102000000380 Matrix Metalloproteinase 1 Human genes 0.000 description 1
- 108010016113 Matrix Metalloproteinase 1 Proteins 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 101710138657 Neurotoxin Proteins 0.000 description 1
- 108700022034 Opsonin Proteins Proteins 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical group CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052927 chalcanthite Inorganic materials 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000013399 early diagnosis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002795 fluorescence method Methods 0.000 description 1
- 238000010362 genome editing Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002581 neurotoxin Substances 0.000 description 1
- 231100000618 neurotoxin Toxicity 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007833 oxidative deamination reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- TUFFYSFVSYUHPA-UHFFFAOYSA-M rhodamine 123 Chemical compound [Cl-].COC(=O)C1=CC=CC=C1C1=C(C=CC(N)=C2)C2=[O+]C2=C1C=CC(N)=C2 TUFFYSFVSYUHPA-UHFFFAOYSA-M 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 108010050939 thrombocytin Proteins 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
-
- 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
-
- 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
- G01N21/6402—Atomic fluorescence; Laser induced fluorescence
-
- 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"
-
- 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
- G01N21/6486—Measuring fluorescence of biological material, e.g. DNA, RNA, cells
-
- 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
-
- 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
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- 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
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Optics & Photonics (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
本发明涉及比率检测单胺氧化酶(MAO)的荧光探针,具体地说,一种有机化合物及其应用。化合物如结构式Ⅰ所示,以所述化合物作为比率的检测线粒体外膜上单胺氧化酶(MAO)的荧光探针。本发明用于比率检测MAO,在MAO存在下对应的荧光波长发生明显位移,可用于MAO的检测,并可大大降低外部检测条件的干扰,提高检测精度。此发明比率检测MAO荧光探针的这类化合物,在MAO存在时,紫外吸收亦发生明显变化,可同时用紫外分光光度计及肉眼进行检测。这类化合物作为荧光探针可用于细胞内外MAO水平的检测,这对深入研究MAO在生物体内催化单胺类物质的方式以及催化产物的产生、聚积等过程的动力学机理,尤其是在研究MAO在生物体中的生理作用以及催化产物对生物生命健康的影响有重要的生物医学意义。
Description
技术领域
本发明涉及比率检测单胺氧化酶(MAO)的荧光探针,具体地说一种有机化合物及其应用。
背景技术
单胺氧化酶(monoamine oxidase,MAO,EC1.4.3.4)是一种位于线粒体外膜上的氧化还原酶,在FAD辅酶的协同作用下催化氧化生物体内产生的胺,包括神经传递素多巴胺、去肾上腺素(NE)、血清素(5-HT)、酪胺、苯乙胺(PEA)以及神经毒素1-甲基-4-苯基-1,2,3,6-四氢嘧啶(MPTP)等,来维持生物体内的胺平衡。由于被不同的基因编辑,MAO分为两种亚型:MAO-A和MAO-B,其对底物或抑制剂选择性、细胞分布、免疫特异性等不同。该酶主要分布在脊椎动物的脑和肝中。当脑内MAO含量异常时,可致神经系统疾病,从而严重地影响人的生活品质和质量;当血清中MAO含量增高时,是一种肝纤维化的信号。因此,通过测定生物体内MAO的含量,从而对其使用相应的抑制剂药物,可实现对某些疾病的早期诊断和治疗。实现实时地、特异性地检测单胺氧化酶具有十分重要的意义。
目前,用于检测MAO的方法包括:分光光度法、放射性法、酶联免疫法、荧光分析法等。在上述方法中,荧光法相比较而言更加具有吸引力,不仅简单易行,价格实惠,便于操作,具有高灵敏度、高选择性的特点,而且可以实现活细胞内MAO“原位可视化”检测,从而对其在生命体内进行“实时在线”观测。Chang C J.等公开了一类用于检测MAO的荧光探针(Chang C J.Chemical Communications,2007(44):4647-4649.),与MAO作用后荧光产生从而检测MAO的存在。但该探针反应前只能在紫外光区检测MAO-A,不能有效避免生物自体荧光的干扰,同时紫外光对生物体光漂白作用很大,易于损伤生物样品。不仅如此,该探针没有定位基团,不能很好的定位到线粒体,因此,开发具有良好选择性,可在近红外区进行联动检测生物体系中MAO的荧光探针具有重要意义。
发明内容
本发明目的在于提供一种基于花菁的有机化合物的合成及其应用。
为实现上述目的,本发明采用技术方案:
一种有机化合物,结构式如式Ⅰ所示,
一种有机化合物的应用,所述式Ⅰ所示的有机化合物在定性的检测细胞或生物体内、外的MAO中的应用。
所述式Ⅰ所示的有机化合物在比率检测线粒体外膜上单胺氧化酶(MAO)的应用。
一种荧光探针,探针为结构式如式Ⅰ所示的有机化合物。
一种荧光探针的应用,所述探针在定性的检测细胞或生物体内、外的MAO中的应用。
所述探针在比率检测线粒体外膜上单胺氧化酶(MAO)的应用。
本发明的有益效果:
本发明化合物用于作为比率检测细胞或生物体内的MAO的荧光探针化合物,其在MAO存在下发生氧化脱氨基作用,使探针有明显的荧光变化,紫外吸收亦发生明显的变化,进而可以用于生物体内MAO的检测。本发明化合物用作荧光探针,可用于细胞内MAO进行检测,还可对细胞内的线粒体进行定位,这对深入研究MAO在生物体内催化单胺类物质、催化方式以及催化产物的产生、聚积等过程的动力学机理,尤其是在研究MAO在生物体中的生理作用以及酶含量地失常引起各种生理病理现象有重要的生物医学意义。
附图说明
图1为本发明实施例提供的采用的荧光探针对MAO检测前后紫外吸收变化图。
图2为本发明实施例提供的采用的荧光探针对MAO检测前后荧光变化图。
图3为本发明实施例提供的所采用的荧光探针对MAO的选择性示意图;其中,横坐标从左至右依次为:空白对照、氯化镁、氯化铁、硫酸锌、葡萄糖、精氨酸、丝氨酸、谷胱甘肽、尿素、基质金属蛋白酶-2、基质金属蛋白酶-9、基质金属蛋白酶-14、磷酸水解酶、单胺氧化酶。
图4为本发明实施例提供的采用荧光探针用于检测细胞线粒体内MAO的共聚焦显微镜成像,其中a代表荧光探针在λem=770–810nm(λex=730nm)的成像;b代表荧光探针在λem=700–740nm(λex=650nm)的成像;c代表商业化线粒体染料在细胞中的成像图;d代表商业化细胞核染料在细胞中的成像图;e代表b,c,d的叠加图。
具体实施方式
下面实施例用于进一步说明本发明,但本发明不限于实施例。
本发明比率检测MAO,在MAO存在下对应的荧光波长发生明显位移,可用于MAO的检测,并可大大降低外部检测条件的干扰,提高检测精度。此发明比率检测MAO荧光探针的这类化合物,在MAO存在时,紫外吸收亦发生明显变化,可同时用紫外分光光度计及肉眼进行检测。这类化合物作为荧光探针可用于细胞内外MAO水平的检测,这对深入研究MAO在生物体内催化单胺类物质的方式以及催化产物的产生、聚积等过程的动力学机理,尤其是在研究MAO在生物体中的生理作用以及催化产物对生物生命健康的影响有重要的生物医学意义。
在MAO存在下对应的荧光波长发生明显位移,用于MAO的检测过程:
基于花菁的有机化合物结构式为:
式Ⅰ化合物与待测定生物体内外中的MAO结合,通过MAO催化式Ⅰ化合物的二甲氨基使其氧化成醛(通过亚胺中间体)丙醛部分通过β消除和一个CO2的自发释放,荧光团被释放,得到结构式II的化合物。从而导致式Ⅰ化合物的荧光,紫外吸收均发生改变,进而可以用来进行MAO的定性检测。
实施例1
基于花青的式Ⅰ有机化合物的制备:
(1)化合物一的制备
在氩气保护下,(4-溴丁基)三苯基溴化磷(14.35g,30mmol)和叠氮钠(3.9g,60mmol)溶于50mL DMF中。90℃条件下,搅拌,过夜。溶液的颜色由无色到浅黄色到红色。将反应瓶冷却到室温,加入50mL二氯甲烷,直到产生大量的沉淀。过滤,收集滤液。收集滤液经乙酸乙酯与水1:1(v/v)萃取,收集有机相,旋蒸。旋蒸后的产物置入圆底烧瓶中,安装回流装置,搅拌,加入约7.5毫升的二氯甲烷使其完全溶解,加热至溶液温度约40℃,回流。回流。溶液微沸时,加入乙酸乙酯,使溶液有白色晶体析出又消失,直至浑浊出现时,再加入二氯甲烷,如此重复3次,冷却,析出晶体,得到化合物一。
1H NMR(400MHz,CDCl3)δ(ppm):7.89-7.85(q,6H),7.82-7.79(t,3H),7.73-7.71(m,6H),3.98-3.92(m,2H),3.46-3.44(t,2H),2.06-2.01(m,2H),1.76-1.74(m,2H).13C NMR(100MHz,CDCl3,ppm)δ134.98,133.72,133.64,130.52,130.42,118.54,117.86,50.59,29.19,29.06,22.34,21.93,19.84,19.80.GC-MS(API-ES):m/z C22H23N3P+[M]+Calcd:360.1624,found:360.4022.
(2)化合物二的制备
在氩气保护下,将抗坏血酸钠(0.01M,1mL)和CuSO4·5H2O(0.01M,1mL)的水溶液混合,得到含有铜(I)催化物质溶液。将商业花菁染料(63.6mg,0.1mmol),化合物一(39.6mg,0.11mmol)和DIPEA(1.5mg,0.01mmol)加入到6.0mL四氢呋喃中,通过恒压滴液漏斗滴加到上述溶液。将混合物在氮气保护下,在25℃下进一步搅拌24小时。真空除去溶剂,所得蓝色固体残余物用梯度洗脱剂CH2Cl2和CH3OH(100:0-85:15,v/v)的硅胶色谱纯化(200-300目),收集洗脱组分即为化合物二。
1H NMR(400MHz,CD3OD)δ(ppm):8.07(s,2H),7.90-7.88(m,6H),7.38-7.37(d,3H),7.32-7.29(m,6H),7.10-7.08(t,3H),7.04-7.00(t,5H),5.75-5.72(d,2H),5.25(s,5H),5.12(s,3H),4.55-4.52(t,3H),4.14-4.08(m,1H),3.43-3.37(m,1H),3.10-3.08(m,2H),2.97-2.93(m,3H),2.69-2.64(m,3H).2.20-2.18(m,3H),2.03(s,1H),1.85-1.81(m,1H),1.76-1.75(d,2H),1.50-1.46(m,1H),1.29-1.21(m,12H),1.05-1.00(m,2H),0.94-0.92(m,2H).13C NMR(100MHz,CD3OD)δ(ppm):169.97,166.81,159.96,157.15,143.82,140.03,137.84,134.94,133.49,133.41,130.26,130.16,128.00,127.91,124.09,122.39,121.69,118.63,117.94,114.55,108.27,93.21,93.08,62.27,61.06,52.30,49.95,38.33,36.31,33.07,30.30,30.17,29.24,29.11,27.70,27.56,21.08,20.93,20.66,20.52,19.49,19.46,19.09,10.27,7.87,6.34.GC-MS(API-ES):m/z C66H73N6OP2+[M]+Calcd:996.557,found:498.6522.
(3)化合物三的制备
在氩气保护下,冷阱控制反应温度在0℃以下,将化合物二(0.10g,0.1mmol)和三光气(12.0mg,0.04mmol)溶于干燥的二氯甲烷(5.0mL)所得溶液搅拌3min,待用;
三乙胺(12.1mg,0.12mmol)溶于二氯甲烷(2.0mL)通过恒压滴液漏斗逐滴滴入混合溶液中,溶液全部由蓝色变为绿色,用饱和NaHCO3水溶液淬灭反应,减压浓缩,所得产物和3-二甲氨基-1-丙醇(31.2mg,0.3mmol)溶于干燥的二氯甲烷(5.0mL)所得溶液搅拌3min,待用;
三乙胺(30.3mg,0.3mmol)溶于二氯甲烷(2.0mL)通过恒压滴液漏斗逐滴滴入混合溶液中,开始反应温度为0℃以下,滴加完毕,升至室温,反应过夜。真空除去溶剂,所得绿色固体残余物用梯度洗脱剂CH2Cl2和CH3OH(100:0-85:15,v/v)的硅胶色谱纯化(200-300目),收集洗脱组分即为式Ⅰ所示有机化合物三。
1H NMR(400MHz,CD3OD)δ(ppm):7.61(s,1H),7.39-7.35(m,18H),7.05-7.02(m,5H),6.98-6.89(m,6H),6.56(t,1H),6.32(s,1H),6.23(m,1H),5.85(s,1H),5.64(s,1H),4.48(t,2H),4.13(q,4H),3.81(s,3H),3.39(q,2H),2.98(m,3H),2.36(m,6H),2.15(s,6H),1.84(m,2H),1.79(s,6H)1.41-1.37(m,14H).13C NMR(100MHz,CD3OD)δ(ppm):173.5,156.2,152.8,146,147.6,144.5,144.0,143.2,136.2,129.1,129,128.7,127.7,121.5,114,111.2,109.6,53.0,51.1,46.3,34.2,14.6.GC-MS(API-ES):m/z C72H84N7O3P2+[M]+Calcd:1125.64,found:562.82.
实施例2
将制备所得式Ⅰ化合物作为探针应用于细胞、组织和器官进行对MAO的检测,模拟生理条件,以下各项实验均在pH=7.4条件下进行(HEPES缓冲溶液,浓度为40mM),探针的浓度采用10μM。
上述制备所得式Ⅰ化合物对MAO的紫外响应:
pH采用HEPES缓冲溶液控制。于10mL比色管中加入式Ⅰ化合物,保证其最终的浓度为10μM,再加入40mM HEPES,然后加入MAO,加入超纯水10mL定容后,使MAO的浓度分别为0μgmL-1,1μg mL-1,2μg mL-1,3μg mL-1,4μg mL-1,5μg mL-1,6μg mL-1,7μg mL-1,8μg mL-1,9μgmL-1,10μg mL-1。摇匀溶液,平衡100min后,将上述工作液加入比色皿中测定紫外吸收光谱。紫外吸收光谱在检测MAO前后的变化如图1所示。式Ⅰ化合物可用于实现生物体内的MAO的检测。同时,本发明实施例所提供的探针与MAO反应后的产物结构如下:
实施例3
式Ⅰ化合物对MAO的荧光响应:
pH采用HEPES缓冲溶液控制。于10mL比色管中加入式Ⅰ化合物,保证其最终的浓度为10μM,再加入40mM HEPES,然后加入MAO,加入超纯水10mL定容后,使MAO的浓度分别为0μgmL-1,1μg mL-1,2μg mL-1,3μg mL-1,4μg mL-1,5μg mL-1,6μg mL-1,7μg mL-1,8μg mL-1,9μgmL-1,10μg mL-1。摇匀溶液,平衡100min后,将上述工作液加入荧光皿中测定荧光光谱光谱。荧光光谱在检测MAO前后的变化如图2所示。式Ⅰ化合物可用于实现生物体内的MAO的检测。
由图2表示随MAO浓度的变化体系荧光强度的变化,表明随MAO浓度的增加,体系760-840nm波段的荧光强度明显减弱,675-820nm波段的荧光强度明显增强。
实施例4
式Ⅰ化合物对MAO的特异性选择
pH采用HEPES缓冲溶液控制。取多个10ml比色管,并在每个10ml比色管中加入10μM式Ⅰ化合物,再加入40mM pH为7.4的HEPES缓冲液,然后分别加入如图3所示,待测物依次为:空白对照、氯化钾、氯化镁、氯化铁、硫酸锌、葡萄糖、VC、精氨酸、丝氨酸、谷胱甘肽、尿素、MMP-2、MMP-9、MMP-12、磷酸水解酶、MAO。最后用超纯水定容到10ml。摇匀溶液,25℃下平衡100min后,将各个比色管中工作液分别倒入到荧光皿中测定荧光光谱。式Ⅰ化合物对MAO的选择性如图3所示。并由图3可知式Ⅰ化合物对MAO具有很好的特异性选择。
实施例5
式Ⅰ化合物用于细胞线粒体内MAO的检测
小鼠肝癌细胞HepG2细胞按照American type Tissue Culture Collection规定进行培养。10.0uM化合物式一孵育HepG2细胞100分钟,用培养基洗涤3次,置于共聚焦荧光显微镜下拍照,结果如图4a,4b所示,其中4a使用的激发波波长为730nm,收集波长范围为770-810nm,4b使用的激发波波长为650nm,收集波长范围为700-740nm;然后加入1uMrhodamine 123(商品化线粒体染色染料)孵育HepG2细胞10分钟,用培养基洗涤3次,置于共聚焦荧光显微镜下拍照,结果如图4c所示;然后加入1uM Hoechest(商品化细胞核染色染料)孵育HepG2细胞10分钟,用培养基洗涤3次,置于共聚焦荧光显微镜下拍照,结果如图4d所示;图4e是叠加图,表明探针主要对线粒体染色。
以上内容是结合具体的优选实施方式对本发明所作的进一步详细说明,不能认定本发明的具体实施只局限于这些说明。对于本发明所属技术领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干简单推演或替换,都应当视为属于本发明的保护范围。作为荧光染料是本发明新化合物的一种用途,不能认定本发明的化合物仅用于荧光染料,对于本发明所属技术领域的普通技术人员来说,在基于本发明化合物用作荧光染料的相同作用机理的考虑下,还可以做出若干简单推理,得出本发明的化合物的其他应用用途,都应当视为属于本发明的保护范围。
Claims (6)
1.一种有机化合物,其特征在于:有机化合物结构式如式Ⅰ所示,
2.一种权利要求1所述的有机化合物的应用,其特征在于:所述式Ⅰ所示的有机化合物在定性的检测细胞或生物体内、外的MAO中的应用。
3.按权利要求2所述的有机化合物的应用,其特征在于:所述式Ⅰ所示的有机化合物在比率检测线粒体外膜上单胺氧化酶(MAO)的应用。
4.一种荧光探针,其特征在于:探针为结构式如式Ⅰ所示的有机化合物。
5.一种权利要求4所述的荧光探针的应用,其特征在于:所述探针在定性的检测细胞或生物体内、外的MAO中的应用。
6.按权利要求5所述的荧光探针的应用,其特征在于:所述探针在比率检测线粒体外膜上单胺氧化酶(MAO)的应用。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201711089014.5A CN107722058B (zh) | 2017-11-08 | 2017-11-08 | 一种有机化合物及其应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201711089014.5A CN107722058B (zh) | 2017-11-08 | 2017-11-08 | 一种有机化合物及其应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN107722058A true CN107722058A (zh) | 2018-02-23 |
CN107722058B CN107722058B (zh) | 2019-07-05 |
Family
ID=61221786
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201711089014.5A Active CN107722058B (zh) | 2017-11-08 | 2017-11-08 | 一种有机化合物及其应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN107722058B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109879821A (zh) * | 2019-03-18 | 2019-06-14 | 济南大学 | 一种检测单胺氧化酶b的基于激发态分子内质子转移的荧光探针的制备 |
CN110746410A (zh) * | 2019-09-26 | 2020-02-04 | 湖南大学 | 一种亮氨酸氨肽酶和单胺氧化酶激活的近红外荧光探针、合成方法及生物应用 |
CN115894294A (zh) * | 2022-11-24 | 2023-04-04 | 山西大学 | 2-(环己-2-烯-1-亚基)丙二腈衍生物及其合成方法和应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104098500A (zh) * | 2014-07-08 | 2014-10-15 | 中国科学院烟台海岸带研究所 | 基于花青的有机化合物及其应用 |
CN104119263A (zh) * | 2014-06-25 | 2014-10-29 | 中国科学院烟台海岸带研究所 | 一种基于花青的有机化合物及其应用 |
CN104119856A (zh) * | 2013-04-26 | 2014-10-29 | 中国科学院大连化学物理研究所 | 一类比率检测次氯酸的荧光探针及其在生物体系内的应用 |
CN104910060A (zh) * | 2015-05-28 | 2015-09-16 | 中国科学院烟台海岸带研究所 | 一种荧光团衍生物及其应用 |
-
2017
- 2017-11-08 CN CN201711089014.5A patent/CN107722058B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104119856A (zh) * | 2013-04-26 | 2014-10-29 | 中国科学院大连化学物理研究所 | 一类比率检测次氯酸的荧光探针及其在生物体系内的应用 |
CN104119263A (zh) * | 2014-06-25 | 2014-10-29 | 中国科学院烟台海岸带研究所 | 一种基于花青的有机化合物及其应用 |
CN104098500A (zh) * | 2014-07-08 | 2014-10-15 | 中国科学院烟台海岸带研究所 | 基于花青的有机化合物及其应用 |
CN104910060A (zh) * | 2015-05-28 | 2015-09-16 | 中国科学院烟台海岸带研究所 | 一种荧光团衍生物及其应用 |
Non-Patent Citations (3)
Title |
---|
AARON E.ALBERS等: "Activity-based fluorescent reporters for monoamine oxidases in living cells", 《CHEMICAL COMMUNICATION》 * |
LIN LI等: "A sensitive two-photon probe to selectively detect monoamine oxidase B activity in Parkinson"s disease models", 《NATURE COMMUNICATIONS》 * |
MIN GAO等: "Fluorescent chemical probes for accurate tumor diagnosis and targeting therapy", 《CHEM. SOC. REV.》 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109879821A (zh) * | 2019-03-18 | 2019-06-14 | 济南大学 | 一种检测单胺氧化酶b的基于激发态分子内质子转移的荧光探针的制备 |
CN110746410A (zh) * | 2019-09-26 | 2020-02-04 | 湖南大学 | 一种亮氨酸氨肽酶和单胺氧化酶激活的近红外荧光探针、合成方法及生物应用 |
CN115894294A (zh) * | 2022-11-24 | 2023-04-04 | 山西大学 | 2-(环己-2-烯-1-亚基)丙二腈衍生物及其合成方法和应用 |
CN115894294B (zh) * | 2022-11-24 | 2024-03-12 | 山西大学 | 2-(环己-2-烯-1-亚基)丙二腈衍生物及其合成方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
CN107722058B (zh) | 2019-07-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Li et al. | A two-photon NIR-to-NIR fluorescent probe for imaging hydrogen peroxide in living cells | |
Liu et al. | A new fluorescent probe with a large turn-on signal for imaging nitroreductase in tumor cells and tissues by two-photon microscopy | |
Xu et al. | Visualization of endoplasmic reticulum aminopeptidase 1 under different redox conditions with a two-photon fluorescent probe | |
Sun et al. | Iridium (III) anthraquinone complexes as two‐photon phosphorescence probes for mitochondria imaging and tracking under hypoxia | |
CN107722057B (zh) | 基于花菁的有机化合物及其应用 | |
Wang et al. | A high performance Schiff-base fluorescent probe for monitoring Au3+ in zebrafish based on BODIPY | |
CN104220438B (zh) | 用于检测过氧亚硝酸盐的二芳基胺‑基荧光探针 | |
Yan et al. | A ratiometric fluorescence probe based on a novel recognition mechanism for monitoring endogenous hypochlorite in living cells | |
CN102344795A (zh) | 一种荧光探针及其在可逆检测次氯酸根上的应用 | |
CN110003060A (zh) | 一种丙二腈衍生物类近红外硫化氢荧光探针及其制备方法与应用 | |
Sha et al. | A mitochondria/lysosome-targeting fluorescence probe based on azonia-cyanine dye and its application in nitroreductase detection | |
CN106518762A (zh) | 一种检测细胞内质网中甲醛的荧光探针 | |
CN107722058B (zh) | 一种有机化合物及其应用 | |
Zhang et al. | An efficient fluorescence sensor for nitroreductase selective imaging based on intramolecular photoinduced electron transfer | |
Jiao et al. | One step synthesis of red-emitting fluorescence turn-on probe for nitroreductase and its application to bacterial detection and oral cancer cell imaging | |
CN106946773A (zh) | 一种比率型双光子甲醛荧光探针及其制备方法和用途 | |
CN108844931A (zh) | Lzq荧光探针在同时检测so2和hsa中的应用 | |
CN109970751A (zh) | 一种双位点、高灵敏pH荧光探针及其合成与应用 | |
Zeng et al. | A near-infrared fluorescent sensor with large Stokes shift for rapid and highly selective detection of thiophenols in water samples and living cells | |
Dai et al. | Construction of a red emission fluorescent protein chromophore-based probe for detection of carboxylesterase 1 and carbamate pesticide in culture cells | |
Huang et al. | Molecular fluorescent probes for imaging and evaluation of peroxynitrite fluctuations in living cells and in vivo under hypoxic stress | |
CN107325062A (zh) | 一种检测过氧化氢活性的荧光探针及制备和应用 | |
CN105985769B (zh) | 一种苯硫酚荧光探针的制备及应用 | |
CN105906619B (zh) | 一种双光子荧光探针及其制备方法和用途 | |
Zhu et al. | Real-time detection of attenuated blood polarity in mouse models of circulating tumor based on a fluorescent probe |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |