Rational Perturbation of the Fluorescence Quantum Yield in Emission-Tunable and Predictable Fluorophores (Seoul-Fluors) by a Facile Synthetic Method Involving CH Activation
Fluorescence imaging enables the uniquely sensitive observation of functional‐ and molecular‐recognition events in living cells. However, only a limited range of biological processes have been subjected to imaging because of the lack of a design strategy and difficulties in the synthesis of biosenso...
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| Published in | Angewandte Chemie International Edition Vol. 53; no. 5; pp. 1346 - 1350 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
27.01.2014
WILEY‐VCH Verlag Wiley |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1433-7851 1521-3773 1521-3773 |
| DOI | 10.1002/anie.201308826 |
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| Abstract | Fluorescence imaging enables the uniquely sensitive observation of functional‐ and molecular‐recognition events in living cells. However, only a limited range of biological processes have been subjected to imaging because of the lack of a design strategy and difficulties in the synthesis of biosensors. Herein, we report a facile synthesis of emission‐tunable and predictable Seoul‐Fluors, 9‐aryl‐1,2‐dihydrolopyrrolo[3,4‐b]indolizin‐3‐ones, with various R1 and R2 substituents by coinage‐metal‐catalyzed intramolecular 1,3‐dipolar cycloaddition and subsequent palladium‐mediated CH activation. We also showed that the quantum yields of Seoul‐Fluors are controlled by the electronic nature of the substituents, which influences the extent of photoinduced electron transfer. On the basis of this understanding, we demonstrated our design strategy by the development of a Seoul‐Fluor‐based chemosensor 20 for reactive oxygen species that was not accessible by a previous synthetic route.
It's all in the design: Seoul‐Fluors with predictable photophysical properties, including a fluorescent reactive‐oxygen‐species sensor that was not previously accessible, were synthesized efficiently by coinage‐metal‐catalyzed intramolecular 1,3‐dipolar cycloaddition and subsequent palladium‐mediated CH activation (see scheme). The quantum yield of the products could be controlled systematically by altering the electronic nature of the substituents. |
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| AbstractList | Fluorescence imaging enables the uniquely sensitive observation of functional- and molecular-recognition events in living cells. However, only a limited range of biological processes have been subjected to imaging because of the lack of a design strategy and difficulties in the synthesis of biosensors. Herein, we report a facile synthesis of emission-tunable and predictable Seoul-Fluors, 9-aryl-1,2-dihydrolopyrrolo[3,4-b]indolizin-3-ones, with various R(1) and R(2) substituents by coinage-metal-catalyzed intramolecular 1,3-dipolar cycloaddition and subsequent palladium-mediated CH activation. We also showed that the quantum yields of Seoul-Fluors are controlled by the electronic nature of the substituents, which influences the extent of photoinduced electron transfer. On the basis of this understanding, we demonstrated our design strategy by the development of a Seoul-Fluor-based chemosensor 20 for reactive oxygen species that was not accessible by a previous synthetic route. Fluorescence imaging enables the uniquely sensitive observation of functional‐ and molecular‐recognition events in living cells. However, only a limited range of biological processes have been subjected to imaging because of the lack of a design strategy and difficulties in the synthesis of biosensors. Herein, we report a facile synthesis of emission‐tunable and predictable Seoul‐Fluors, 9‐aryl‐1,2‐dihydrolopyrrolo[3,4‐ b ]indolizin‐3‐ones, with various R 1 and R 2 substituents by coinage‐metal‐catalyzed intramolecular 1,3‐dipolar cycloaddition and subsequent palladium‐mediated CH activation. We also showed that the quantum yields of Seoul‐Fluors are controlled by the electronic nature of the substituents, which influences the extent of photoinduced electron transfer. On the basis of this understanding, we demonstrated our design strategy by the development of a Seoul‐Fluor‐based chemosensor 20 for reactive oxygen species that was not accessible by a previous synthetic route. Fluorescence imaging enables the uniquely sensitive observation of functional-and molecular-recognition events in living cells. However, only a limited range of biological processes have been subjected to imaging because of the lack of a design strategy and difficulties in the synthesis of biosensors. Herein, we report a facile synthesis of emission-tunable and predictable Seoul-Fluors, 9-aryl-1,2-dihydrolopyrrolo[3,4-b]indolizin-3-ones, with various R-1 and R-2 substituents by coinage-metal-catalyzed intramolecular 1,3-dipolar cycloaddition and subsequent palladium-mediated C-H activation. We also showed that the quantum yields of Seoul-Fluors are controlled by the electronic nature of the substituents, which influences the extent of photoinduced electron transfer. On the basis of this understanding, we demonstrated our design strategy by the development of a Seoul-Fluor-based chemosensor 20 for reactive oxygen species that was not accessible by a previous synthetic route. Fluorescence imaging enables the uniquely sensitive observation of functional‐ and molecular‐recognition events in living cells. However, only a limited range of biological processes have been subjected to imaging because of the lack of a design strategy and difficulties in the synthesis of biosensors. Herein, we report a facile synthesis of emission‐tunable and predictable Seoul‐Fluors, 9‐aryl‐1,2‐dihydrolopyrrolo[3,4‐ b ]indolizin‐3‐ones, with various R 1 and R 2 substituents by coinage‐metal‐catalyzed intramolecular 1,3‐dipolar cycloaddition and subsequent palladium‐mediated C—H activation. We also showed that the quantum yields of Seoul‐Fluors are controlled by the electronic nature of the substituents, which influences the extent of photoinduced electron transfer. On the basis of this understanding, we demonstrated our design strategy by the development of a Seoul‐Fluor‐based chemosensor 20 for reactive oxygen species that was not accessible by a previous synthetic route. Fluorescence imaging enables the uniquely sensitive observation of functional- and molecular-recognition events in living cells. However, only a limited range of biological processes have been subjected to imaging because of the lack of a design strategy and difficulties in the synthesis of biosensors. Herein, we report a facile synthesis of emission-tunable and predictable Seoul-Fluors, 9-aryl-1,2-dihydrolopyrrolo[3,4-b]indolizin-3-ones , with various R super(1) and R super(2) substituents by coinage-metal-catalyzed intramolecular 1,3-dipolar cycloaddition and subsequent palladium-mediated C--H activation. We also showed that the quantum yields of Seoul-Fluors are controlled by the electronic nature of the substituents, which influences the extent of photoinduced electron transfer. On the basis of this understanding, we demonstrated our design strategy by the development of a Seoul-Fluor-based chemosensor 20 for reactive oxygen species that was not accessible by a previous synthetic route. It's all in the design: Seoul-Fluors with predictable photophysical properties, including a fluorescent reactive-oxygen-species sensor that was not previously accessible, were synthesized efficiently by coinage-metal-catalyzed intramolecular 1,3-dipolar cycloaddition and subsequent palladium-mediated C--H activation (see scheme). The quantum yield of the products could be controlled systematically by altering the electronic nature of the substituents. Fluorescence imaging enables the uniquely sensitive observation of functional‐ and molecular‐recognition events in living cells. However, only a limited range of biological processes have been subjected to imaging because of the lack of a design strategy and difficulties in the synthesis of biosensors. Herein, we report a facile synthesis of emission‐tunable and predictable Seoul‐Fluors, 9‐aryl‐1,2‐dihydrolopyrrolo[3,4‐b]indolizin‐3‐ones, with various R1 and R2 substituents by coinage‐metal‐catalyzed intramolecular 1,3‐dipolar cycloaddition and subsequent palladium‐mediated CH activation. We also showed that the quantum yields of Seoul‐Fluors are controlled by the electronic nature of the substituents, which influences the extent of photoinduced electron transfer. On the basis of this understanding, we demonstrated our design strategy by the development of a Seoul‐Fluor‐based chemosensor 20 for reactive oxygen species that was not accessible by a previous synthetic route. It's all in the design: Seoul‐Fluors with predictable photophysical properties, including a fluorescent reactive‐oxygen‐species sensor that was not previously accessible, were synthesized efficiently by coinage‐metal‐catalyzed intramolecular 1,3‐dipolar cycloaddition and subsequent palladium‐mediated CH activation (see scheme). The quantum yield of the products could be controlled systematically by altering the electronic nature of the substituents. Fluorescence imaging enables the uniquely sensitive observation of functional- and molecular-recognition events in living cells. However, only a limited range of biological processes have been subjected to imaging because of the lack of a design strategy and difficulties in the synthesis of biosensors. Herein, we report a facile synthesis of emission-tunable and predictable Seoul-Fluors, 9-aryl-1,2-dihydrolopyrrolo[3,4-b]indolizin-3-ones, with various R(1) and R(2) substituents by coinage-metal-catalyzed intramolecular 1,3-dipolar cycloaddition and subsequent palladium-mediated CH activation. We also showed that the quantum yields of Seoul-Fluors are controlled by the electronic nature of the substituents, which influences the extent of photoinduced electron transfer. On the basis of this understanding, we demonstrated our design strategy by the development of a Seoul-Fluor-based chemosensor 20 for reactive oxygen species that was not accessible by a previous synthetic route.Fluorescence imaging enables the uniquely sensitive observation of functional- and molecular-recognition events in living cells. However, only a limited range of biological processes have been subjected to imaging because of the lack of a design strategy and difficulties in the synthesis of biosensors. Herein, we report a facile synthesis of emission-tunable and predictable Seoul-Fluors, 9-aryl-1,2-dihydrolopyrrolo[3,4-b]indolizin-3-ones, with various R(1) and R(2) substituents by coinage-metal-catalyzed intramolecular 1,3-dipolar cycloaddition and subsequent palladium-mediated CH activation. We also showed that the quantum yields of Seoul-Fluors are controlled by the electronic nature of the substituents, which influences the extent of photoinduced electron transfer. On the basis of this understanding, we demonstrated our design strategy by the development of a Seoul-Fluor-based chemosensor 20 for reactive oxygen species that was not accessible by a previous synthetic route. |
| Author | Park, Seung Bum Kim, Eunha Lee, Youngjun Choi, Eun Joung Jo, Ala |
| AuthorAffiliation | 2 Department of Biophysics and Chemical Biology, Seoul National University, Seoul 151‐747 (Korea) 1 Department of Chemistry/Bio‐MAX Institute, Seoul National University, Seoul 151‐747 (Korea) 3 Current address: The Center for Systems Biology, Massachusetts General Hospital/Harvard Medical School, 185 Cambridge Street, CPZN 5206, Boston, MA (USA) |
| AuthorAffiliation_xml | – name: 1 Department of Chemistry/Bio‐MAX Institute, Seoul National University, Seoul 151‐747 (Korea) – name: 2 Department of Biophysics and Chemical Biology, Seoul National University, Seoul 151‐747 (Korea) – name: 3 Current address: The Center for Systems Biology, Massachusetts General Hospital/Harvard Medical School, 185 Cambridge Street, CPZN 5206, Boston, MA (USA) |
| Author_xml | – sequence: 1 givenname: Eun Joung surname: Choi fullname: Choi, Eun Joung organization: Department of Chemistry/Bio-MAX Institute, Seoul National University, Seoul 151-747 (Korea) – sequence: 2 givenname: Eunha surname: Kim fullname: Kim, Eunha organization: Department of Chemistry/Bio-MAX Institute, Seoul National University, Seoul 151-747 (Korea) – sequence: 3 givenname: Youngjun surname: Lee fullname: Lee, Youngjun organization: Department of Chemistry/Bio-MAX Institute, Seoul National University, Seoul 151-747 (Korea) – sequence: 4 givenname: Ala surname: Jo fullname: Jo, Ala organization: Department of Chemistry/Bio-MAX Institute, Seoul National University, Seoul 151-747 (Korea) – sequence: 5 givenname: Seung Bum surname: Park fullname: Park, Seung Bum email: sbpark@snu.ac.kr organization: Department of Chemistry/Bio-MAX Institute, Seoul National University, Seoul 151-747 (Korea) |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/24446281$$D View this record in MEDLINE/PubMed |
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| Copyright | 2014 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of Creative Commons the Attribution Non‐Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of Creative Commons the Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made. 2014 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. |
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| Notes | Funded Access This research was supported by the Bio & Medical Technology Development Program (2012M3A9C4048780), the Basic Research Laboratory (2010-0019766), and a Global Frontier Project Grant (2013M3A6A4044245) funded by the National Research Foundation of Korea. E.J.C., Y.L., and A.J. are grateful for their predoctoral fellowships awarded by the BK21 Program. National Research Foundation of Korea istex:61492DE412808682BD8973B4866F1F7FE5A8224F ark:/67375/WNG-KPQLBXXT-M ArticleID:ANIE201308826 This research was supported by the Bio & Medical Technology Development Program (2012M3A9C4048780), the Basic Research Laboratory (2010‐0019766), and a Global Frontier Project Grant (2013M3A6A4044245) funded by the National Research Foundation of Korea. E.J.C., Y.L., and A.J. are grateful for their predoctoral fellowships awarded by the BK21 Program. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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| PublicationTitle | Angewandte Chemie International Edition |
| PublicationTitleAbbrev | ANGEW CHEM INT EDIT |
| PublicationTitleAlternate | Angew. Chem. Int. Ed |
| PublicationYear | 2014 |
| Publisher | WILEY-VCH Verlag WILEY‐VCH Verlag Wiley |
| Publisher_xml | – name: WILEY-VCH Verlag – name: WILEY‐VCH Verlag – name: Wiley |
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| Snippet | Fluorescence imaging enables the uniquely sensitive observation of functional‐ and molecular‐recognition events in living cells. However, only a limited range... Fluorescence imaging enables the uniquely sensitive observation of functional-and molecular-recognition events in living cells. However, only a limited range... Fluorescence imaging enables the uniquely sensitive observation of functional- and molecular-recognition events in living cells. However, only a limited range... |
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| SubjectTerms | Accessibility Activation Carbon - chemistry Catalysis Chemistry Chemistry, Multidisciplinary Communication Communications Cycloaddition Reaction CH activation Design engineering Electron Transport Electronics Fluorescence Fluorescent Dyes - chemical synthesis Fluorescent Dyes - chemistry fluorophore design Heterocyclic Compounds, 4 or More Rings - chemical synthesis Heterocyclic Compounds, 4 or More Rings - chemistry Hydrogen - chemistry Imaging Palladium - chemistry Physical Sciences Pyrroles - chemical synthesis Pyrroles - chemistry Quantum Theory quantum yield Reactive Oxygen Species - chemistry Science & Technology Strategy switchable sensors Synthesis |
| Title | Rational Perturbation of the Fluorescence Quantum Yield in Emission-Tunable and Predictable Fluorophores (Seoul-Fluors) by a Facile Synthetic Method Involving CH Activation |
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