title: A simple and versatile design concept for fluorophore derivatives with intramolecular photostabilization.
abstract: Intramolecular photostabilization via triple-state quenching was recently revived as a tool to impart synthetic organic fluorophores with 'self-healing' properties. To date, utilization of such fluorophore derivatives is rare due to their elaborate multi-step synthesis. Here we present a general strategy to covalently link a synthetic organic fluorophore simultaneously to a photostabilizer and biomolecular target via unnatural amino acids. The modular approach uses commercially available starting materials and simple chemical transformations. The resulting photostabilizer-dye conjugates are based on rhodamines, carbopyronines and cyanines with excellent photophysical properties, that is, high photostability and minimal signal fluctuations. Their versatile use is demonstrated by single-step labelling of DNA, antibodies and proteins, as well as applications in single-molecule and super-resolution fluorescence microscopy. We are convinced that the presented scaffolding strategy and the improved characteristics of the conjugates in applications will trigger the broader use of intramolecular photostabilization and help to emerge this approach as a new gold standard.
authors.affiliation: Molecular Microscopy Research Group, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
authors.forename: Jasper H M
authors.initials: JH
authors.lastname: van der Velde
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
authors.forename: Jens
authors.initials: J
authors.lastname: Oelerich
authors.affiliation: Department of Polymer Chemistry, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
authors.forename: Jingyi
authors.initials: J
authors.lastname: Huang
authors.affiliation: Molecular Microscopy Research Group, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
authors.forename: Jochem H
authors.initials: JH
authors.lastname: Smit
authors.affiliation: Molecular Microscopy Research Group, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
authors.forename: Atieh
authors.initials: A
authors.lastname: Aminian Jazi
authors.affiliation: MRC Human Immunology Unit, Weatherall Institute of Molecular Medicine, University of Oxford, Headley Way, Oxford OX3 9DS, UK.
authors.forename: Silvia
authors.initials: S
authors.lastname: Galiani
authors.affiliation: Department NanoBiophotonics, Max-Planck-Institute of Molecular Medicine, Am Fassberg 1, 37077 Goettingen, Germany.
authors.forename: Kirill
authors.initials: K
authors.lastname: Kolmakov
authors.affiliation: Molecular Microscopy Research Group, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
authors.forename: Giorgos
authors.initials: G
authors.lastname: Guoridis
authors.affiliation: MRC Human Immunology Unit, Weatherall Institute of Molecular Medicine, University of Oxford, Headley Way, Oxford OX3 9DS, UK.
authors.forename: Christian
authors.initials: C
authors.lastname: Eggeling
authors.affiliation: Department of Polymer Chemistry, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
authors.forename: Andreas
authors.initials: A
authors.lastname: Herrmann
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
authors.forename: Gerard
authors.initials: G
authors.lastname: Roelfes
authors.affiliation: Molecular Microscopy Research Group, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
authors.forename: Thorben
authors.initials: T
authors.lastname: Cordes
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D002232:Carbocyanines / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D002839:Chromans / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D002853:Chromatography, Liquid; D004277:DNA, Single-Stranded / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D005998:Glycine / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008856:Microscopy, Fluorescence; D009841:Oligonucleotides / Q000737:chemistry*; D010649:Phenylalanine / Q000737:chemistry; D012235:Rhodamines / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D002232:Carbocyanines; D002839:Chromans; D004277:DNA, Single-Stranded; D005456:Fluorescent Dyes; D009841:Oligonucleotides; D012235:Rhodamines; C085321:cyanine dye 5; D010649:Phenylalanine; C029773:rhodamine B; C010643:6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid; D005998:Glycine