• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

支化对具有偶极子与八极子电荷分布的阳离子三芳基硼发色团的单光子和双光子吸收、细胞活力和细胞定位的影响,用于细胞成像。

The Effect of Branching on the One- and Two-Photon Absorption, Cell Viability, and Localization of Cationic Triarylborane Chromophores with Dipolar versus Octupolar Charge Distributions for Cellular Imaging.

机构信息

Institut für Anorganische Chemie, and Institute for Sustainable Chemistry, & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, 97074, Würzburg, Germany.

Institut für Organische Chemie, Julius-Maximilians-Universität Würzburg, 97074, Würzburg, Germany.

出版信息

Chemistry. 2019 Oct 11;25(57):13164-13175. doi: 10.1002/chem.201902461. Epub 2019 Sep 17.

DOI:10.1002/chem.201902461
PMID:31322301
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6857003/
Abstract

Two different chromophores, namely a dipolar and an octupolar system, were prepared and their linear and nonlinear optical properties as well as their bioimaging capabilities were compared. Both contain triphenylamine as the donor and a triarylborane as the acceptor, the latter modified with cationic trimethylammonio groups to provide solubility in aqueous media. The octupolar system exhibits a much higher two-photon brightness, and also better cell viability and enhanced selectivity for lysosomes compared with the dipolar chromophore. Furthermore, both dyes were applied in two-photon excited fluorescence (TPEF) live-cell imaging.

摘要

两种不同的生色团,即偶极子和八极子体系,被制备出来,并对它们的线性和非线性光学性质以及它们的生物成像能力进行了比较。两者都以三苯胺为供体,以三芳基硼烷为受体,后者用阳离子三甲铵基团修饰以提供在水介质中的溶解性。与偶极生色团相比,八极生色团表现出更高的双光子亮度,以及更好的细胞活力和增强的溶酶体选择性。此外,两种染料都被应用于双光子激发荧光(TPEF)活细胞成像。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/5c2a2d48bed3/CHEM-25-13164-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/9862205d011d/CHEM-25-13164-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/94cc07f59c13/CHEM-25-13164-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/a641d373f5a7/CHEM-25-13164-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/2580aec2cead/CHEM-25-13164-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/9eab28e3510a/CHEM-25-13164-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/4ff8b1dd56cc/CHEM-25-13164-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/8bca608c129a/CHEM-25-13164-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/2b3810f1bff9/CHEM-25-13164-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/c34acf3b0989/CHEM-25-13164-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/43ca0d573dbe/CHEM-25-13164-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/5e929254c060/CHEM-25-13164-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/5c2a2d48bed3/CHEM-25-13164-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/9862205d011d/CHEM-25-13164-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/94cc07f59c13/CHEM-25-13164-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/a641d373f5a7/CHEM-25-13164-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/2580aec2cead/CHEM-25-13164-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/9eab28e3510a/CHEM-25-13164-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/4ff8b1dd56cc/CHEM-25-13164-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/8bca608c129a/CHEM-25-13164-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/2b3810f1bff9/CHEM-25-13164-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/c34acf3b0989/CHEM-25-13164-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/43ca0d573dbe/CHEM-25-13164-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/5e929254c060/CHEM-25-13164-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b942/6857003/5c2a2d48bed3/CHEM-25-13164-g010.jpg

相似文献

1
The Effect of Branching on the One- and Two-Photon Absorption, Cell Viability, and Localization of Cationic Triarylborane Chromophores with Dipolar versus Octupolar Charge Distributions for Cellular Imaging.支化对具有偶极子与八极子电荷分布的阳离子三芳基硼发色团的单光子和双光子吸收、细胞活力和细胞定位的影响,用于细胞成像。
Chemistry. 2019 Oct 11;25(57):13164-13175. doi: 10.1002/chem.201902461. Epub 2019 Sep 17.
2
Dipolar versus octupolar triphenylamine-based fluorescent organic nanoparticles as brilliant one- and two-photon emitters for (bio)imaging.基于偶极子和八极子三苯胺的荧光有机纳米粒子作为明亮的单光子和双光子发射器在(生物)成像中的应用。
Small. 2011 Nov 18;7(22):3219-29. doi: 10.1002/smll.201100726. Epub 2011 Oct 4.
3
Benzothiazoles with tunable electron-withdrawing strength and reverse polarity: a route to triphenylamine-based chromophores with enhanced two-photon absorption.具有可调电子受体强度和反转极性的苯并噻唑:一种基于三苯胺的生色团的增强型双光子吸收的途径。
J Org Chem. 2011 Nov 4;76(21):8726-36. doi: 10.1021/jo201411t. Epub 2011 Oct 3.
4
The effectiveness of essential-state models in the description of optical properties of branched push-pull chromophores.支化推-拉发色团光学性质描述中本征态模型的有效性。
Phys Chem Chem Phys. 2010 Oct 7;12(37):11715-27. doi: 10.1039/c003563g. Epub 2010 Aug 10.
5
Water-Soluble Triarylborane Chromophores for One- and Two-Photon Excited Fluorescence Imaging of Mitochondria in Cells.用于细胞中线粒体单光子和双光子激发荧光成像的水溶性三芳基硼烷发色团
Chemistry. 2016 Oct 4;22(41):14701-6. doi: 10.1002/chem.201602639. Epub 2016 Sep 15.
6
Two-photon polarity probes built from octupolar fluorophores: synthesis, structure-properties relationships, and use in cellular imaging.基于八极荧光团的双光子极性探针:合成、结构-性质关系及在细胞成像中的应用。
Chem Asian J. 2013 Dec;8(12):2984-3001. doi: 10.1002/asia.201300735. Epub 2013 Sep 9.
7
Optimization of Aqueous Stability versus π-Conjugation in Tetracationic Bis(triarylborane) Chromophores: Applications in Live-Cell Fluorescence Imaging.四阳离子双(三芳基硼)生色团中水溶液稳定性与π 共轭的优化:在活细胞荧光成像中的应用。
Chemistry. 2019 Jun 7;25(32):7679-7688. doi: 10.1002/chem.201900723. Epub 2019 Apr 30.
8
Octupolar merocyanine dyes: a new class of nonlinear optical chromophores.八极型菁染料:一类新型的非线性光学发色团。
Chemistry. 2012 Jul 23;18(30):9258-66. doi: 10.1002/chem.201200718. Epub 2012 Jun 21.
9
Mitochondria-targeted cationic porphyrin-triphenylamine hybrids for enhanced two-photon photodynamic therapy.用于增强双光子光动力疗法的线粒体靶向阳离子卟啉-三苯胺杂化物
Bioorg Med Chem. 2018 Jan 1;26(1):107-118. doi: 10.1016/j.bmc.2017.11.024. Epub 2017 Nov 15.
10
A self-assembled nanohybrid composed of fluorophore-phenylamine nanorods and Ag nanocrystals: energy transfer, wavelength shift of fluorescence and TPEF applications for live-cell imaging.由荧光团-苯胺纳米棒和 Ag 纳米晶体组成的自组装纳米杂化体:能量转移、荧光波长移动以及用于活细胞成像的 TPEF 应用。
Chemistry. 2013 Dec 2;19(49):16625-33. doi: 10.1002/chem.201302874. Epub 2013 Nov 6.

引用本文的文献

1
Breaking Bonds by Light: The Absorbance-Fragmentation Paradox.光致断键:吸光度-碎片化悖论
Chemistry. 2025 Aug 18;31(46):e01839. doi: 10.1002/chem.202501839. Epub 2025 Jul 22.
2
Intramolecular arylsulfide-coordinated diboraanthracenes: effect of B-S coordination on ground-state and excited-state behavior.分子内芳基硫醚配位的二硼蒽:B-S配位对基态和激发态行为的影响
Chem Sci. 2025 Apr 14;16(20):8764-8771. doi: 10.1039/d5sc01726b. eCollection 2025 May 21.
3
Regioisomers containing triarylboron-based motifs as multi-functional photoluminescent materials: from dual-mode delayed emission to pH-switchable room-temperature phosphorescence.

本文引用的文献

1
Tuning the π-bridge of quadrupolar triarylborane chromophores for one- and two-photon excited fluorescence imaging of lysosomes in live cells.调控四极三芳基硼烷发色团的π桥用于活细胞中溶酶体的单光子和双光子激发荧光成像
Chem Sci. 2019 Apr 23;10(20):5405-5422. doi: 10.1039/c9sc00793h. eCollection 2019 May 28.
2
Application of Triarylboron Substituted with Cyclic Arginine-Glycine-Aspartic Acid Motifs as a Multivalent Two-Photon Fluorescent Probe for Tumor Imaging in Vivo.环状精氨酸-甘氨酸-天冬氨酸基取代三芳基硼作为一种新型多价双光子荧光探针用于活体肿瘤成像。
Anal Chem. 2019 May 7;91(9):6340-6344. doi: 10.1021/acs.analchem.9b01324. Epub 2019 Apr 22.
3
含有三芳基硼基 motif 的区域异构体作为多功能光致发光材料:从双模延迟发射到 pH 可切换室温磷光
Chem Sci. 2024 Oct 7;15(44):18364-78. doi: 10.1039/d4sc05656f.
4
The Fabrication and Mechanism of a Crystalline Organic Fluorescent Probe Based on Photoinduced Electron Transfer.基于光致电子转移的晶体有机荧光探针的制备及其机理
Molecules. 2023 Sep 23;28(19):6774. doi: 10.3390/molecules28196774.
5
The Nature of the (Oligo/Hetero)Arene Linker Connecting Two Triarylborane Cations Controls Fluorimetric and Circular Dichroism Sensing of Various ds-DNAs and ds-RNAs.(寡聚/杂)芳基连接子将两个三芳基硼阳离子连接起来的性质控制着对各种 ds-DNA 和 ds-RNA 的荧光和圆二色性检测。
Molecules. 2023 May 25;28(11):4348. doi: 10.3390/molecules28114348.
6
Electron-Rich EDOT Linkers in Tetracationic bis-Triarylborane Chromophores: Influence on Water Stability, Biomacromolecule Sensing, and Photoinduced Cytotoxicity.富电子 EDOT 连接体在四阳离子双三芳基硼发色团中的应用:对水稳定性、生物大分子传感和光诱导细胞毒性的影响。
Chemistry. 2022 Aug 26;28(48):e202201130. doi: 10.1002/chem.202201130. Epub 2022 Jul 4.
7
Methyl Viologens of Bis-(4'-Pyridylethynyl)Arenes - Structures, Photophysical and Electrochemical Studies, and their Potential Application in Biology.双-(4'-吡啶基乙炔基)芳烃的甲紫精 - 结构、光物理和电化学研究及其在生物学中的潜在应用。
Chemistry. 2022 Jul 15;28(40):e202200753. doi: 10.1002/chem.202200753. Epub 2022 May 30.
8
Fully fused boron-doped polycyclic aromatic hydrocarbons: their synthesis, structure-property relationships, and self-assembly behavior in aqueous media.完全融合的硼掺杂多环芳烃:其合成、结构-性能关系及在水性介质中的自组装行为
Chem Sci. 2022 Jan 6;13(5):1484-1491. doi: 10.1039/d1sc06710a. eCollection 2022 Feb 2.
9
Triarylborane Dyes as a Novel Non-Covalent and Non-Inhibitive Fluorimetric Markers for DPP III Enzyme.三芳基硼烷染料作为一种新型的非共价且非抑制性的二肽基肽酶III荧光标记物
Molecules. 2021 Aug 9;26(16):4816. doi: 10.3390/molecules26164816.
10
Bithiophene-Cored, mono-, bis-, and tris-(Trimethylammonium)-Substituted, bis-Triarylborane Chromophores: Effect of the Number and Position of Charges on Cell Imaging and DNA/RNA Sensing.并噻吩核心的单取代、双取代和三取代、双三芳基硼烷生色团:电荷数和位置对细胞成像和 DNA/RNA 传感的影响。
Chemistry. 2021 Oct 7;27(56):14057-14072. doi: 10.1002/chem.202102308. Epub 2021 Aug 31.
Optimization of Aqueous Stability versus π-Conjugation in Tetracationic Bis(triarylborane) Chromophores: Applications in Live-Cell Fluorescence Imaging.
四阳离子双(三芳基硼)生色团中水溶液稳定性与π 共轭的优化:在活细胞荧光成像中的应用。
Chemistry. 2019 Jun 7;25(32):7679-7688. doi: 10.1002/chem.201900723. Epub 2019 Apr 30.
4
Donor-π-Acceptor Type Unsymmetrical Triarylborane-Based Fluorophores: Synthesis, Fluorescence Properties, and Photostability.供体-π-受体型不对称三芳基硼烷类荧光团:合成、荧光性质及光稳定性
J Org Chem. 2018 Aug 3;83(15):8449-8456. doi: 10.1021/acs.joc.8b01015. Epub 2018 Jun 12.
5
A water-soluble two-photon ratiometric triarylboron probe with nucleolar targeting by preferential RNA binding.一种通过优先结合RNA实现核仁靶向的水溶性双光子比率型三芳基硼探针。
Chem Commun (Camb). 2017 Oct 17;53(83):11476-11479. doi: 10.1039/c7cc06045a.
6
Optical and electronic properties of air-stable organoboron compounds with strongly electron-accepting bis(fluoromesityl)boryl groups.具有强吸电子双(氟代均三甲苯基)硼基的空气稳定有机硼化合物的光学和电子性质
Chem Sci. 2015 Jan 1;6(1):308-321. doi: 10.1039/c4sc02410a. Epub 2014 Oct 1.
7
Recent developments in and perspectives on three-coordinate boron materials: a bright future.三配位硼材料的最新进展与展望:光明的未来
Chem Sci. 2017 Feb 1;8(2):846-863. doi: 10.1039/c6sc04245g. Epub 2016 Nov 9.
8
Charge-Transfer Emitting Triarylborane π-Electron Systems.电荷转移发光三芳基硼烷π电子体系
Inorg Chem. 2017 Aug 7;56(15):8705-8717. doi: 10.1021/acs.inorgchem.6b02847. Epub 2017 Feb 6.
9
Water-Soluble Triarylborane Chromophores for One- and Two-Photon Excited Fluorescence Imaging of Mitochondria in Cells.用于细胞中线粒体单光子和双光子激发荧光成像的水溶性三芳基硼烷发色团
Chemistry. 2016 Oct 4;22(41):14701-6. doi: 10.1002/chem.201602639. Epub 2016 Sep 15.
10
Merging thiophene with boron: new building blocks for conjugated materials.噻吩与硼的融合:共轭材料的新型构建单元
Dalton Trans. 2016 Sep 28;45(36):13996-4007. doi: 10.1039/c6dt02756c. Epub 2016 Aug 5.