CN113999203B - Near infrared fluorescent dye and method for detecting SO (SO) 32- /HSO 3- The above application - Google Patents
Near infrared fluorescent dye and method for detecting SO (SO) 32- /HSO 3- The above application Download PDFInfo
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- CN113999203B CN113999203B CN202111188751.7A CN202111188751A CN113999203B CN 113999203 B CN113999203 B CN 113999203B CN 202111188751 A CN202111188751 A CN 202111188751A CN 113999203 B CN113999203 B CN 113999203B
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- near infrared
- fluorescent dye
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- sodium
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- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 54
- 238000000034 method Methods 0.000 title abstract description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 72
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000001514 detection method Methods 0.000 claims description 9
- BWOVACANEIVHST-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)acetonitrile Chemical compound C1=CC=C2NC(CC#N)=NC2=C1 BWOVACANEIVHST-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 150000003248 quinolines Chemical class 0.000 claims description 7
- ZMZSYUSDGRJZNT-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)acetonitrile Chemical compound C1=CC=C2SC(CC#N)=NC2=C1 ZMZSYUSDGRJZNT-UHFFFAOYSA-N 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- IMXRZJSHQIESSW-UHFFFAOYSA-N 6-(diethylamino)quinoline-2-carbaldehyde Chemical compound C(C)N(C=1C=C2C=CC(=NC2=CC=1)C=O)CC IMXRZJSHQIESSW-UHFFFAOYSA-N 0.000 claims description 5
- AYIIFDAAXPMDAG-UHFFFAOYSA-N 6-methoxyquinoline-2-carbaldehyde Chemical compound N1=C(C=O)C=CC2=CC(OC)=CC=C21 AYIIFDAAXPMDAG-UHFFFAOYSA-N 0.000 claims description 5
- WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- VFEFBBNVGPMCMK-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)acetonitrile;2-(1,3-benzothiazol-2-yl)acetonitrile Chemical compound C1=CC=C2NC(CC#N)=NC2=C1.C1=CC=C2SC(CC#N)=NC2=C1 VFEFBBNVGPMCMK-UHFFFAOYSA-N 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 239000000523 sample Substances 0.000 abstract description 32
- 239000011259 mixed solution Substances 0.000 abstract description 5
- 239000000243 solution Substances 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 3
- 230000004044 response Effects 0.000 abstract description 3
- 230000007774 longterm Effects 0.000 abstract 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 24
- 239000000975 dye Substances 0.000 description 21
- 239000010413 mother solution Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 12
- 238000002189 fluorescence spectrum Methods 0.000 description 12
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 12
- 235000010265 sodium sulphite Nutrition 0.000 description 12
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 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 8
- 239000012452 mother liquor Substances 0.000 description 8
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 8
- -1 biology Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000005284 excitation Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 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 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- 108010024636 Glutathione Proteins 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 239000005708 Sodium hypochlorite Substances 0.000 description 4
- 235000010323 ascorbic acid Nutrition 0.000 description 4
- 229960005070 ascorbic acid Drugs 0.000 description 4
- 239000011668 ascorbic acid Substances 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 4
- 235000018417 cysteine Nutrition 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 239000011790 ferrous sulphate Substances 0.000 description 4
- 235000003891 ferrous sulphate Nutrition 0.000 description 4
- 229960003180 glutathione Drugs 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 4
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 4
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 4
- 235000019799 monosodium phosphate Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 4
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 4
- 239000004317 sodium nitrate Substances 0.000 description 4
- 235000010344 sodium nitrate Nutrition 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
- 235000019345 sodium thiosulphate Nutrition 0.000 description 4
- PVGBHEUCHKGFQP-UHFFFAOYSA-N sodium;n-[5-amino-2-(4-aminophenyl)sulfonylphenyl]sulfonylacetamide Chemical compound [Na+].CC(=O)NS(=O)(=O)C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 PVGBHEUCHKGFQP-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000012491 analyte Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 238000001917 fluorescence detection Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 230000004043 responsiveness Effects 0.000 description 2
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 2
- 239000002904 solvent Substances 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 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000003891 environmental analysis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000009585 enzyme analysis Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 238000012632 fluorescent imaging Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000003333 near-infrared imaging Methods 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 125000006853 reporter group Chemical group 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
- C09B23/005—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof
- C09B23/0058—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof the substituent being CN
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
- C09B23/102—The polymethine chain containing an even number of >CH- groups two heterocyclic rings linked carbon-to-carbon
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
- C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
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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
-
- 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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- 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
- G01N21/645—Specially adapted constructive features of fluorimeters
- G01N21/6456—Spatial resolved fluorescence measurements; Imaging
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- 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
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- Materials Engineering (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses a series of near infrared fluorescent dyes and a method for detecting SO 3 2‑ / HSO 3 ‑ The above application. The probe provided by the invention presents near infrared fluorescence in the mixed solution of DMSO and PBS, and the wavelength of the probe can be further red shifted along with the improvement of the proportion of the PBS solution, and can be matched with SO 2 Specific reaction is generated to generate obvious fluorescence blue shift change, thereby realizing SO 2 Is a specific response of (a). The probe has good stability, simple preparation, long-term storage and use, and can be used for SO 2 And also has good selectivity.
Description
Technical Field
The patent technology belongs to the field of fluorescent dyes, and particularly relates to preparation and application of near infrared fluorescent dyes.
Background
Fluorescent dyes are an important branch of dye chemistry. In recent decades, fluorescent dyes and derivatives thereof have made a lot of breakthrough progress in materials, biology, medicine and the like, and gradually become a key research direction in dye chemistry.
With rapid development of analytical chemistry, bioscience, life science, medicine and other subjects, organic fluorescent dyes have been widely applied to various aspects such as biomolecular labeling, enzyme analysis, environmental analysis, cell staining, clinical examination and diagnosis, and are indispensable fluorescent signal reporter groups in chemical, biological, environmental science and medical research. Therefore, development of functional organic fluorescent dyes having practical value has been an object of current study. In particular, with the development of life science, people hope to obtain visual information of molecular or ionic biological functions, so various imaging technologies are rapidly developed, and near infrared imaging is always a focus of attention, and compared with the traditional analysis technology, near infrared fluorescence imaging has the advantages of non-destructiveness, high sensitivity, good selectivity and the like. The development of fluorescent imaging is limited by the properties of fluorescent dyes, so that the development of fluorescent dyes with excellent performance, particularly near infrared fluorescent dyes (emission wavelength is more than or equal to 650 nm), is an important research direction of chemical biology, and near infrared fluorescent dyes are functional dyes, and because the near infrared fluorescent dyes have good absorption in a near infrared light region, the near infrared technology has wide application in cell imaging, tumor treatment, biological molecular marking, medical diagnosis and the like. The common near infrared organic dye is a cyanine dye, and has poor light stability; the phthalocyanine dye has high synthesis requirement, low yield, large molecular volume and poor solubility; the metal complex dye has poor solubility and low absorption strength.
Aiming at the problems of poor stability, short emission wavelength, poor solubility and the like of the traditional fluorescent dye, the invention constructs a series of novel fluorescent dyes by a hybridization strategy aiming at improving the photophysical and photochemical properties of the fluorescent dye, in particular to obtain two near infrared fluorescent dyes (SZ-1 emission wavelength is 699nm and MZ-1 emission wavelength is 656nm in a mixed solvent (VDMSO: VPBS=3:7)), which have the excellent characteristics of good light and heat stability, good solubility, emission wavelength and the like, and the dyes are primarily applied to the design and development of probes.
Disclosure of Invention
The invention aims at synthesizing a series of simple and efficient fluorescent dyes, in particular to near infrared fluorescent dyes and researching spectral properties.
The aim of the invention is achieved by the following technical scheme:
a series of quinoline derivatives, compounds with quinoline imidazole (thiazole) ring structures, which have the following structural formulas:
the substituent R comprises any one of methoxy, hydrogen and diethylamino.
The preparation method of the fluorescent dye compound comprises the following steps: dissolving 2-cyanomethyl benzimidazole (2-cyanomethyl benzothiazole) and quinoline derivatives in ethanol, adding proper amount of acetic acid, stirring at normal temperature for reaction for 3.5 hours, placing reactants into a refrigerator after the reaction is finished, precipitating, filtering, washing and drying to obtain a target compound product
The method comprises the following synthetic paths:
the substituent R comprises any one of methoxy, hydrogen and diethylamino.
The molar ratio of the quinoline derivative to the 2-cyanomethyl benzimidazole (benzothiazole-2-acetonitrile) to the acetic acid is 1: (1-1.5): (1-1.5).
The synthetic route of the fluorescent dye of the invention is as follows:
the other technical scheme of the invention is to use the fluorescent dye compound as a fluorescent dye.
The fluorescent dye compound is used as fluorescent dye in detecting dimethyl sulfoxide solution.
The near infrared fluorescent dye is used for detecting SO 2 And the use of derivatives thereof for detecting SO 2 The derivative comprises SO 3 2- Or HSO 3 - 。
Quinoline is a typical class of organic molecular luminophores with a large pi conjugated structure. Quinoline derivatives are heterocyclic compounds with relatively common biological activity and pharmacological activity, and have important application in the fields of medicine, molecular biology, dye industry and the like. Quinoline is structurally a condensed body of pyridine and benzene, but is similar in chemical nature to pyridine and benzene. Nucleophilic substitution occurs in the pyridine ring, and electrophilic substitution occurs almost exclusively in the benzene ring. The invention can greatly change the fluorescence quantum yield of the product and the wavelength of the compound by changing the type of the benzene ring substituent.
The series of fluorescent dye compounds of the invention obtain two near infrared fluorescent dyes, and the two near infrared fluorescent dyes have strong light and heat stability, are simple to prepare, can effectively avoid the fluorescence interference of cells, have stronger and more obvious penetration of red signals in organisms, can be directly used for cell imaging, and can also be used for detecting SO at the same time 2 Fluorescent probes of the derivatives. In addition, by changing the substituents on the benzene rings, four other dyes are obtained, but the electron donating ability is weak, compared with two near infrared dyes, the wavelength is shorter, and the effect is inferior to that of the two near infrared dyes.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of a fluorescent dye of MZ-1.
FIG. 2 is a nuclear magnetic resonance spectrum of a fluorescent dye of MZ-2.
FIG. 3 is a nuclear magnetic resonance spectrum of a fluorescent dye of MZ-3.
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of the fluorescent dye of SZ-1.
FIG. 5 is a nuclear magnetic resonance hydrogen spectrum of the fluorescent dye of SZ-2.
FIG. 6 is a nuclear magnetic resonance hydrogen spectrum of SZ-3 fluorescent dye.
FIG. 7 is a fluorescence spectrum of MZ-1, MZ-2, MZ-3 in DMSO.
FIG. 8 is a fluorescence spectrum of SZ-1, SZ-2, SZ-3 in DMSO.
FIG. 9 shows the fluorescent dye of example 1 as a reagent for detecting SO 2 Fluorescence spectrum of fluorescent probe.
FIG. 10 shows the fluorescent dye of example 1 as a reagent for detecting SO 2 The fluorescence spectrum of the fluorescence probe selectivity is as follows from 1 to 18: 1. blank 2, sodium azide 3, sodium chloride 4, sodium sulfate 5, sodium carbonate 6, sodium nitrate 7, sodium dihydrogen phosphate 8, ascorbic acid 9, glutathione 10, cysteine 11, calcium chloride 12, ferrous sulfate 13, sodium hypochlorite 14, hydrogen peroxide 15, sodium thiosulfate 16, hydrazine hydrate 17, sodium bisulfite 18, sodium sulfite.
FIG. 11 shows the use of fluorescent dye of example 4 as a detector for SO 2 Fluorescence spectrum of fluorescent probe.
FIG. 12 shows the use of fluorescent dye of example 4 as a detector for SO 2 The fluorescence spectrum of the fluorescence probe selectivity is as follows from 1 to 18: 1. blank 2, sodium azide 3, sodium chloride 4, sodium sulfate 5, sodium carbonate 6, sodium nitrate 7, sodium dihydrogen phosphate 8, ascorbic acid 9, glutathione 10, cysteine 11, calcium chloride 12, ferrous sulfate 13, sodium hypochlorite 14, hydrogen peroxide 15, sodium thiosulfate 16, hydrazine hydrate 17, sodium bisulfite 18, sodium sulfite.
The specific implementation method comprises the following steps:
example 1: synthesis of Compound MZ-1
50mg (0.22 mol) of 6- (diethylamino) quinoline-2-carbaldehyde and 34.4mg (0.22 mol) of 2-cyanomethyl benzimidazole were weighed into a 25ml reaction flask, 13.2mg (0.22 mol) of acetic acid was added, and dissolved in 2ml of absolute ethanol, and stirred at room temperature for 3.5 hours, and the reaction was monitored by TLC (thin layer chromatography) plates until the starting material was completely reacted, and filtered under reduced pressure, washed to give 55mg of a red solid in 68% yield.
Example 2: synthesis of Compound MZ-2
50mg (0.32 mol) of quinoline-2-carbaldehyde and 50.24mg (0.32 mol) of 2-cyanomethyl benzimidazole were weighed into a 25ml reaction flask, 19.2mg (0.32 mol) of acetic acid was added, and then 2ml of absolute ethanol was added for dissolution, and stirred at room temperature for 3.5 hours, and the TLC plate was used for monitoring the reaction until the starting material was completely reacted. Washing under reduced pressure gave 73mg of a black solid in 77% yield.
Example 3: synthesis of Compound MZ-3
50mg (0.267 mol) of 6-methoxyquinoline-2-carbaldehyde and 42mg (0.267 mol) of 2-cyanomethyl benzimidazole were weighed into a 25ml reaction flask, 16mg (0.32 mol) of acetic acid was added, 2ml of absolute ethanol was then added for dissolution, and the mixture was stirred at room temperature for 3.5 hours, and the reaction was monitored by a TLC (thin layer chromatography) plate until the starting material was completely reacted. Washing under reduced pressure gave 76mg of green solid in 87% yield.
Example 4: synthesis of Compound SZ-1
50mg (0.22 mol) of 6- (diethylamino) quinoline-2-carbaldehyde and 38.3mg (0.22 mol) of 2-cyanomethylbenzothiazole were weighed into a 25ml reaction flask, 13.2mg (0.22 mol) of acetic acid was added, and then 2ml of absolute ethanol was added for dissolution, and stirred at room temperature for 3.5 hours, and the reaction was monitored by a TLC plate until the starting material was completely reacted. Washing under reduced pressure gave 58.3mg of a dark red solid in 69% yield.
Example 5: synthesis of Compound SZ-2
50mg (0.318 mol) of quinoline-2-carbaldehyde and 55mg (0.318 mol) of 2-cyanomethylbenzothiazole were weighed into a 25ml reaction flask, 19mg (0.318 mol) of acetic acid was added, and then 2ml of absolute ethanol was added for dissolution, and stirred at room temperature for 3.5 hours, and the reaction was monitored by a TLC plate until the starting material was completely reacted. Washing under reduced pressure gave 67mg of green solid in 67% yield.
Example 6: synthesis of Compound SZ-3
50mg (0.267 mol) of 6-methoxyquinoline-2-carbaldehyde and 46.5mg (0.267 mol) of 2-cyanomethylbenzothiazole were weighed into a 25ml reaction flask, 16mg (0.267 mol) of acetic acid was added, 2ml of absolute ethyl alcohol was further added, stirring was carried out at room temperature for 3.5 hours, and the reaction was monitored by a TLC plate until the starting material was completely reacted. The mixture was washed by filtration under reduced pressure to give 56.4mg of a green solid in 61% yield
A, D and F are 6- (diethylamino) quinoline-2-formaldehyde, 2-cyanomethyl benzimidazole and acetic acid
B, D and F are quinoline-2-formaldehyde, 2-cyanomethyl benzimidazole and acetic acid
C, D and F are 6-methoxyquinoline-2-formaldehyde, 2-cyanomethyl benzimidazole and acetic acid
A, E and F are 6- (diethylamino) quinoline-2-carbaldehyde, 2-cyanomethylbenzothiazole and acetic acid
B, E and F are quinoline-2-formaldehyde, 2-benzothiazole-2-acetonitrile and acetic acid
C, E and F are 6-methoxyquinoline-2-formaldehyde, 2-cyanomethyl benzothiazole and acetic acid
Example 7: effect of fluorochromes in DMSO
The MZ-1, MZ-2, MZ-3, SZ-1, SZ-2, SZ-3 compounds prepared in examples 1 to 6 were dissolved in DMSO solutions, respectively, to prepare 1mM mother solutions. In the test tube, adding DMSO, each test tube 3mL, taking 6 μL (2 μM) from mother liquor, adding into each test tube, adopting 480nm excitation wavelength, adopting fluorescence spectrometer to test the emission spectrum of each compound in DMSO solvent, and adopting fluorescence spectrometer to test the test results, wherein the test results are shown in FIG. 7 and FIG. 8, the emission wavelengths of different compounds in the same solvent are different, the emission wavelength of MZ-1 in DMSO is 627nm, the emission wavelength of MZ-2 in DMSO is 527nm, the emission wavelength of MZ-3 in DMSO is 466nm, the emission wavelength of SZ-1 in DMSO is 668nm, the emission wavelength of SZ-2 in DMSO is 523nm, and the emission wavelength of SZ-3 in DMSO is 484nm, because the substituents on quinoline groups are different in power supply capability, the diethylamino groups are the strongest, the methoxy times and the hydrogen is the weakest, the intramolecular electron transfer degree is different, and the intramolecular electron transfer degree is larger, and the wavelength is longer.
Example 8:MZ-1 probe pair SO 2 Concentration fluorescence detection of (2)
The MZ-1 compound prepared in example 1 was dissolved in DMSO solution to prepare a 1mM mother solution. NaHSO is carried out 3 Dissolved in deionized water to prepare a mother solution of 5 mM. The mixed solution (PBS: dmso=7:3) was added to each tube, 3mL of each tube, 6 μl (2 μΜ) was removed from MZ-1 mother liquor and added to each tube, followed by different volumes of NaHSO 3 The mother liquor was reacted in a test tube for 25 minutes. NaHSO of the probe was measured with a fluorescence spectrometer at various concentrations (0. Mu.L, 3. Mu.L, 6. Mu.L, 9. Mu.L, 12. Mu.L, 15. Mu.L, 18. Mu.L, 21. Mu.L, 24. Mu.L, 27. Mu.L, 30. Mu.L, 36. Mu.L, 42. Mu.L, 48. Mu.L, 54. Mu.L, 60. Mu.L, 72. Mu.L, 84. Mu.L, 96. Mu.L, 108. Mu.L, 120. Mu.L) using an excitation wavelength of 400nm 3 Is a change in fluorescence spectrum of (a). The change in fluorescence spectrum is shown in FIG. 9. The results showed that with the addition of different concentrations of NaHSO 3 After that, the fluorescence emission was enhanced at 478nm and decreased at 656 nm. Due to NaHSO 3 The continuous addition of the dye destroys the conjugated system of the dye, SO that the excitation wavelength is shortened, the fluorescence color is changed from red to blue, and the detection of SO can be achieved 2 Is a target of (a). .
The dyes MZ-2, MZ-3 also have a similar structure and are therefore also capable of reacting with NaHSO 3 Reaction takes place, thereby realizing the reaction to SO 2 However, since the emission wavelengths of the dyes MZ-2 and MZ-3 are short, the detection of the dye is not effective as a probe because the dye is interfered by background fluorescence and MZ-1 is not used as a probe.
Example 9: MZ-1 probe pair SO 2 Selective detection of (2)
The probe compound MZ-1 prepared in example 1 was dissolved in DMSO to prepare a probe mother solution of 1mM, and NaHSO was used 3 Dissolved in deionized water to prepare a mother solution of 5 mM. 17 mother solutions (1, sodium azide 2, sodium chloride 3, sodium sulfate 4, sodium carbonate 5, sodium nitrate 6, sodium dihydrogen phosphate 7, ascorbic acid 8, glutathione 9, cysteine 10, calcium chloride 11, ferrous sulfate 12, sodium hypochlorite 13, hydrogen peroxide 14, sodium thiosulfate 15, hydrazine hydrate 16, sodium hydrogen sulfite 17, sodium sulfite) were prepared. Add (PBS: dmso=7:3) mixed solution to the tube, every timeRoot tube 3mL. 6. Mu.L (2. Mu.M) of the mother liquor of MZ-1 was taken out from the mother liquor of MZ-1 and added to each test tube, 100. Mu.L (200. Mu.M) of the mother liquor of different choice with the same concentration was taken in the test tube containing 3mL of the probe, after the reaction was carried out for 25 minutes, the change of the fluorescence spectrum of the probe reacted with the different choice and probe with the same concentration was tested by a fluorescence spectrometer using an excitation wavelength of 400 nm. FIG. 10 shows that sodium bisulfite and sodium sulfite alone produced a strong fluorescence change effect on the probe, resulting in sodium bisulfite and sodium sulfite alone having a higher response to the probe.
Since the dyes MZ-2 and MZ-3 also have similar structures, the reaction of MZ-1 and the analyte can be concluded that the reaction of MZ-1 and the analyte is the same, and sodium bisulphite and sodium sulfite have fluorescence change effects on the probe, so that sodium bisulphite and sodium sulfite have higher responsiveness to the probe.
Example 10: SZ-1 probe pair SO 2 Concentration fluorescence detection of (2)
The SZ-1 compound prepared in example 4 was dissolved in DMSO solution to prepare a 1mM mother solution. NaHSO is carried out 3 Dissolved in deionized water to prepare a mother solution of 5 mM. The mixed solution (PBS: dmso=7:3) was added to each tube, 3mL of each tube, 6 μl (2 μΜ) was removed from MZ-1 mother liquor and added to each tube, followed by different volumes of NaHSO 3 The mother liquor was reacted in a test tube for 15 minutes. Fluorescence spectra of the probes at different concentrations (0. Mu.L, 3. Mu.L, 6. Mu.L, 9. Mu.L, 12. Mu.L, 15. Mu.L, 18. Mu.L, 21. Mu.L, 24. Mu.L, 27. Mu.L, 30. Mu.L, 36. Mu.L, 42. Mu.L, 48. Mu.L, 54. Mu.L, 60. Mu.L) were measured with a fluorescence spectrometer using an excitation wavelength of 400 nm. The change in fluorescence spectrum is shown in FIG. 11. The results showed that with the addition of different concentrations of NaHSO 3 After that, the fluorescence emission is enhanced at 478nm and reduced at 699nm, due to NaHSO 3 The continuous addition of the dye destroys the conjugated system of the dye, SO that the excitation wavelength is shortened, the fluorescence color is changed from red to blue, and the detection of SO can be achieved 2 Is a target of (a). .
The dyes SZ-2, SZ-3 also have a similar structure and are therefore also capable of reacting with NaHSO 3 Reaction takes place, thereby realizing the reaction to SO 2 Is detected.
Example 10: SZ-1 probe pair SO 2 Selective detection of (2)
The probe compound SZ-1 prepared in example 4 was dissolved in DMSO to prepare a probe mother solution of 1mM, and NaHSO was used 3 Dissolved in deionized water to prepare a mother solution of 5 mM. 17 mother solutions (1, sodium azide 2, sodium chloride 3, sodium sulfate 4, sodium carbonate 5, sodium nitrate 6, sodium dihydrogen phosphate 7, ascorbic acid 8, glutathione 9, cysteine 10, calcium chloride 11, ferrous sulfate 12, sodium hypochlorite 13, hydrogen peroxide 14, sodium thiosulfate 15, hydrazine hydrate 16, sodium hydrogen sulfite 17, sodium sulfite) were prepared. Mixed solution (PBS: dmso=7:3) was added to the tubes, 3mL per tube. 6 mu L (2 mu M) of the SZ-1 mother solution is taken out and added into each test tube, 100 mu L (200 mu M) of the mother solution of different choices with the same concentration is taken in the test tube containing 3mL of the probe, after 15 minutes of reaction, the fluorescence spectrum change condition of the probe, which reacts with the different choices with the same concentration and the probe, is tested by a fluorescence spectrometer by adopting the excitation wavelength of 400 nm. FIG. 12 shows that sodium bisulfite and sodium sulfite alone produced a strong fluorescence change effect on the probe, resulting in sodium bisulfite and sodium sulfite alone having a higher response to the probe.
Since the dyes SZ-2 and SZ-3 also have similar structures, the reaction with the analytes can conclude that SZ-1 reacts with the analytes, and only sodium bisulphite and sodium sulfite have fluorescence change effects on the probes, so that only sodium bisulphite and sodium sulfite have higher responsiveness to the probes.
Claims (5)
1. Detection of SO in DMSO solution with near infrared fluorescent dye 2 The application of the fluorescent probe of the derivative thereof is characterized in that the structural formula of the near infrared fluorescent dye is selected from any one of the following formulas:
2. according to the weightsDetection of SO in DMSO solution using near infrared fluorescent dye according to claim 1 2 Use of a fluorescent probe of a derivative thereof, characterized in that it comprises the steps of: dissolving 2-cyanomethyl benzimidazole or 2-cyanomethyl benzothiazole and quinoline derivatives in ethanol, adding a proper amount of acetic acid, stirring at normal temperature for reaction, precipitating after the reaction is finished, filtering, washing and drying to obtain a target compound product, wherein the reaction formula is as follows:
the substituent R is selected from any one of methoxy, hydrogen and diethylamino.
3. Detection of SO in DMSO solution using near infrared fluorescent dye according to claim 2 2 The application of the derivative thereof on fluorescent probes is characterized in that the quinoline derivative is selected from any one of 6- (diethylamino) quinoline-2-formaldehyde, quinoline-2-formaldehyde or 6-methoxyquinoline-2-formaldehyde.
4. Detection of SO in DMSO solution using near infrared fluorescent dye according to claim 2 2 The application of the fluorescent probe of the derivative thereof is characterized in that the mol ratio of the quinoline derivative to the 2-cyanomethyl benzimidazole (2-cyanomethyl benzothiazole) to the acetic acid is 1: (1-1.5): (1-1.5).
5. Detection of SO in DMSO solution using near infrared fluorescent dye according to claim 2 2 The application of the fluorescent probe of the derivative thereof is characterized in that the reaction condition is stirring reaction for 3-3.5 hours at normal temperature.
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