Modular Synthetic Approach to Silicon-Rhodamine Homologues and Analogues via Bis-aryllanthanum Reagents

被引:14
作者
Butkevich, Alexey N. [1 ]
机构
[1] Max Planck Inst Med Res, Dept Opt Nanoscopy, D-69120 Heidelberg, Germany
关键词
FLUORESCENT-PROBES; CELL; FLUOROPHORE; MICROSCOPY;
D O I
10.1021/acs.orglett.1c00512
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A modular synthetic approach toward diverse analogues of the far-red fluorophore silicon-rhodamine (SiR), based on a regioselective double nucleophilic addition of aryllanthanum reagents to esters, anhydrides, and lactones, is proposed. The reaction has improved functional group tolerance and represents a unified strategy toward cell-permeant, spontaneously blinking, and photoactivatable SiR fluorescent labels. In tandem with Pd-catalyzed hydroxy- or aminocarbonylation, it serves a streamlined synthetic pathway to a series of validated live-cell-compatible fluorescent dyes.
引用
收藏
页码:2604 / 2609
页数:6
相关论文
共 41 条
[1]  
[Anonymous], 1988, SPECTROCHIM ACTA A, V44, P1053
[2]   Nanometer resolution imaging and tracking of fluorescent molecules with minimal photon fluxes [J].
Balzarotti, Francisco ;
Eilers, Yvan ;
Gwosch, Klaus C. ;
Gynna, Arvid H. ;
Westphal, Volker ;
Stefani, Fernando D. ;
Elf, Johan ;
Hell, Stefan W. .
SCIENCE, 2017, 355 (6325) :606-612
[3]   Enhancing the biocompatibility of rhodamine fluorescent probes by a neighbouring group effect [J].
Bucevicius, Jonas ;
Kostiuk, Georgij ;
Gerasimaite, Ruta ;
Gilat, Tanja ;
Lukinavicius, Grazvydas .
CHEMICAL SCIENCE, 2020, 11 (28) :7313-7323
[4]   Rhodamine-Hoechst positional isomers for highly efficient staining of heterochromatin [J].
Bucevicius, Jonas ;
Keller-Findeisen, Jan ;
Gilat, Tanja ;
Hell, Stefan W. ;
Lukinavicius, Grazvydas .
CHEMICAL SCIENCE, 2019, 10 (07) :1962-1970
[5]   Hydroxylated Fluorescent Dyes for Live-Cell Labeling: Synthesis, Spectra and Super-Resolution STED Microscopy [J].
Butkevich, Alexey N. ;
Belov, Vladimir N. ;
Kolmakov, Kirill ;
Sokolov, Viktor V. ;
Shojaei, Heydar ;
Sidenstein, Sven C. ;
Kamin, Dirk ;
Matthias, Jessica ;
Vlijm, Rifka ;
Engelhardt, Johann ;
Hell, Stefan W. .
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (50) :12114-12119
[6]   Fluorescent Rhodamines and Fluorogenic Carbopyronines for Super-Resolution STED Microscopy in Living Cells [J].
Butkevich, Alexey N. ;
Mitronova, Gyuzel Yu ;
Sidenstein, Sven C. ;
Klocke, Jessica L. ;
Kamin, Dirk ;
Meineke, Dirk N. H. ;
D'Este, Elisa ;
Kraemer, Philip-Tobias ;
Danzl, Johann G. ;
Belov, Vladimir N. ;
Hell, Stefan W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (10) :3290-3294
[7]   Localization microscopy at doubled precision with patterned illumination [J].
Cnossen, Jelmer ;
Hinsdale, Taylor ;
Thorsen, Rasmus O. ;
Siemons, Marijn ;
Schueder, Florian ;
Jungmann, Ralf ;
Smith, Carlas S. ;
Rieger, Bernd ;
Stallinga, Sjoerd .
NATURE METHODS, 2020, 17 (01) :59-+
[8]   Fluorescent probes for super-resolution imaging in living cells [J].
Fernandez-Suarez, Marta ;
Ting, Alice Y. .
NATURE REVIEWS MOLECULAR CELL BIOLOGY, 2008, 9 (12) :929-943
[9]   Direct Transformation of Esters into Heterocyclic Fluorophores [J].
Fischer, Christian ;
Sparr, Christof .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (09) :2436-2440
[10]   Photoactivation of silicon rhodamines via a light-induced protonation [J].
Frei, Michelle S. ;
Hoess, Philipp ;
Lampe, Marko ;
Nijmeijer, Bianca ;
Kueblbeck, Moritz ;
Ellenberg, Jan ;
Wadepohl, Hubert ;
Ries, Jonas ;
Pitsch, Stefan ;
Reymond, Luc ;
Johnsson, Kai .
NATURE COMMUNICATIONS, 2019, 10 (1)