CN103864685B - 一种荧光探针及其在检测二价铁离子中的应用 - Google Patents
一种荧光探针及其在检测二价铁离子中的应用 Download PDFInfo
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- CN103864685B CN103864685B CN201210551877.0A CN201210551877A CN103864685B CN 103864685 B CN103864685 B CN 103864685B CN 201210551877 A CN201210551877 A CN 201210551877A CN 103864685 B CN103864685 B CN 103864685B
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- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 229910001448 ferrous ion Inorganic materials 0.000 title claims abstract description 24
- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 24
- 238000001514 detection method Methods 0.000 title abstract description 10
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- PWZJNFCGAWSKHV-UHFFFAOYSA-N 2-butyl-6-hydroxybenzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(N(CCCC)C2=O)=O)=C3C2=CC=CC3=C1O PWZJNFCGAWSKHV-UHFFFAOYSA-N 0.000 claims 2
- 238000004088 simulation Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 4
- 229910052714 tellurium Inorganic materials 0.000 abstract description 4
- 239000000376 reactant Substances 0.000 abstract description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 40
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
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- 229910052742 iron Inorganic materials 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
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- 238000010586 diagram Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 230000004962 physiological condition Effects 0.000 description 2
- 230000035790 physiological processes and functions Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010065973 Iron Overload Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
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- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 208000030172 endocrine system disease Diseases 0.000 description 1
- 230000037149 energy metabolism Effects 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
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- 238000001727 in vivo Methods 0.000 description 1
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- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000001457 metallic cations Chemical class 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
-
- 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
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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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
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CN201210551877.0A CN103864685B (zh) | 2012-12-17 | 2012-12-17 | 一种荧光探针及其在检测二价铁离子中的应用 |
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CN201210551877.0A CN103864685B (zh) | 2012-12-17 | 2012-12-17 | 一种荧光探针及其在检测二价铁离子中的应用 |
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CN103864685A CN103864685A (zh) | 2014-06-18 |
CN103864685B true CN103864685B (zh) | 2015-10-21 |
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Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN107033078B (zh) * | 2017-05-25 | 2019-10-18 | 西北师范大学 | 含有羟基萘甲醛结构的铁离子传感器分子及其合成和应用 |
CN110981857B (zh) * | 2019-11-21 | 2022-09-09 | 山东省科学院生物研究所 | 一种超灵敏亚铁离子荧光探针、制备方法与应用 |
CN112209877A (zh) * | 2020-04-15 | 2021-01-12 | 广东省微生物研究所(广东省微生物分析检测中心) | 一种二价铁荧光探针及其应用 |
CN114262304A (zh) * | 2021-12-13 | 2022-04-01 | 武汉大学中南医院 | 响应Fe(Ⅱ)离子的生物发光荧光素的合成方法及其应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101786985A (zh) * | 2010-02-05 | 2010-07-28 | 苏州大学 | 萘酰亚胺衍生物及其作为荧光探针应用 |
WO2010099214A1 (en) * | 2009-02-27 | 2010-09-02 | Nitto Denko Corporation | Lyotropic chromophoric compounds, liquid crystal systems and optically anisotropic films |
CN102391150A (zh) * | 2011-09-08 | 2012-03-28 | 山东轻工业学院 | 一种铁离子荧光探针化合物及其制备方法 |
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JP2982621B2 (ja) * | 1994-07-22 | 1999-11-29 | 味の素株式会社 | 光増感機能をもつ新規アミノ酸 |
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- 2012-12-17 CN CN201210551877.0A patent/CN103864685B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010099214A1 (en) * | 2009-02-27 | 2010-09-02 | Nitto Denko Corporation | Lyotropic chromophoric compounds, liquid crystal systems and optically anisotropic films |
CN101786985A (zh) * | 2010-02-05 | 2010-07-28 | 苏州大学 | 萘酰亚胺衍生物及其作为荧光探针应用 |
CN102391150A (zh) * | 2011-09-08 | 2012-03-28 | 山东轻工业学院 | 一种铁离子荧光探针化合物及其制备方法 |
Non-Patent Citations (1)
Title |
---|
高选择性铁离子荧光探针的合成及性质研究;黎俊波,等;《武汉工程大学学报》;20100531;第32卷(第5期);第11-14页 * |
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Effective date of registration: 20180119 Address after: 215600 A 207 room A building center of Zhangjiagang Free Trade Zone, Suzhou Free Trade Zone, Jiangsu Patentee after: ZHANGJIAGANG INDUSTRY TECHNOLOGY RESEARCH INSTITUTE CO.,LTD. DALIAN INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES Address before: 116023 Zhongshan Road, Liaoning, No. 457, Patentee before: Dalian Institute of Chemical Physics, Chinese Academy of Sciences |
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Effective date of registration: 20240121 Address after: 116023 No. 457, Zhongshan Road, Liaoning, Dalian Patentee after: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCES Country or region after: China Address before: Room 207, Building A, Emerging Industry Development Center, Zhangjiagang Free Trade Zone, Suzhou City, Jiangsu Province Patentee before: ZHANGJIAGANG INDUSTRY TECHNOLOGY RESEARCH INSTITUTE CO.,LTD. DALIAN INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES Country or region before: China |