title: Water-Soluble NIR-Absorbing Rylene Chromophores for Selective Staining of Cellular Organelles.
abstract: Biocompatible organic dyes emitting in the near-infrared are highly desirable in fluorescence imaging techniques. Herein we report a synthetic approach for building novel small peri-guanidine-fused naphthalene monoimide and perylene monoimide chromophores. The presented structures possess near-infrared absorption and emission, high photostability, and good water solubility. After a fast cellular uptake, they selectively stain mitochondria with a low background in live and fixed cells. They can be additionally modified in a one-step reaction with functional groups for covalent labeling of proteins. The low cytotoxicity allows a long time exposure of live cells to the dyes without the necessity of washing. Successful application in localization super-resolution microscopy was demonstrated in phosphate-buffered saline without any reducing or oxidizing additives.
authors.affiliation: Max Planck Institute for Polymer Research , Ackermannweg 10, 55128 Mainz, Germany.
authors.forename: Stefka
authors.initials: S
authors.lastname: Kaloyanova
authors.affiliation: Faculty of Chemistry and Pharmacy, Sofia University 'St. Kliment Ohridski' , 1 James Bourchier Ave., Sofia 1164, Bulgaria.
authors.forename: Yulian
authors.initials: Y
authors.lastname: Zagranyarski
authors.affiliation: Microscopy Core Facility, Institute of Molecular Biology , Ackermannweg 4, 55128 Mainz, Germany.
authors.forename: Sandra
authors.initials: S
authors.lastname: Ritz
authors.affiliation: Microscopy Core Facility, Institute of Molecular Biology , Ackermannweg 4, 55128 Mainz, Germany.
authors.forename: Mária
authors.initials: M
authors.lastname: Hanulová
authors.affiliation: Max Planck Institute for Polymer Research , Ackermannweg 10, 55128 Mainz, Germany.
authors.forename: Kaloian
authors.initials: K
authors.lastname: Koynov
authors.affiliation: Microscopy Core Facility, Institute of Molecular Biology , Ackermannweg 4, 55128 Mainz, Germany.
authors.forename: Andreas
authors.initials: A
authors.lastname: Vonderheit
authors.affiliation: Max Planck Institute for Polymer Research , Ackermannweg 10, 55128 Mainz, Germany.
authors.forename: Klaus
authors.initials: K
authors.lastname: Müllen
authors.affiliation: Max Planck Institute for Polymer Research , Ackermannweg 10, 55128 Mainz, Germany.|Laboratory of Organic and Macromolecular Chemistry, Jena Center of Soft Matter, Friedrich Schiller University Jena , Lessingstrasse 8, 07743 Jena, Germany.
authors.forename: Kalina
authors.initials: K
authors.lastname: Peneva
mesh_terms: D000818:Animals; D002522:Chlorocebus aethiops; D004396:Coloring Agents / Q000138:chemical synthesis / Q000737:chemistry*; D019791:Guanidine / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D007094:Imides / Q000737:chemistry; D061986:MCF-7 Cells; D008928:Mitochondria / Q000737:chemistry*; D009281:Naphthalenes / Q000737:chemistry; D010569:Perylene / Q000737:chemistry*; D019265:Spectroscopy, Near-Infrared / Q000379:methods*; D013194:Staining and Labeling / Q000379:methods*; D014709:Vero Cells
chemical_list: D004396:Coloring Agents; D007094:Imides; D009281:Naphthalenes; C031721:naphthalene; D010569:Perylene; D019791:Guanidine