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Red-Emitting Rhodamines with Hydroxylated, Sulfonated, and Phosphorylated Dye Residues and Their Use in Fluorescence Nanoscopy

MPS-Authors
http://pubman.mpdl.mpg.de/cone/persons/resource/persons45939

Kolmakov,  Kirill
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons16058

Wurm,  C.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;
Georg-August University of Göttingen, Medical School, Department of Neurology, Göttingen;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons86321

Hennig,  Rene
Bioprocess Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons86442

Rapp,  Erdmann
Bioprocess Engineering, Max Planck Institute for Dynamics of Complex Technical Systems, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons15269

Jakobs,  S.
Research Group of Mitochondrial Structure and Dynamics, MPI for biophysical chemistry, Max Planck Society;
Georg-August University of Göttingen, Medical School, Department of Neurology, Göttingen;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons14832

Belov,  V. N.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons15210

Hell,  S. W.
Department of NanoBiophotonics, MPI for biophysical chemistry, Max Planck Society;

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Citation

Kolmakov, K., Wurm, C., Hennig, R., Rapp, E., Jakobs, S., Belov, V. N., et al. (2012). Red-Emitting Rhodamines with Hydroxylated, Sulfonated, and Phosphorylated Dye Residues and Their Use in Fluorescence Nanoscopy. Chemistry - A European Journal, 18(41), 12986-12998. doi:10.1002/chem.201201168.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0013-8AA4-5
Abstract
Fluorescent dyes emitting red light are frequently used in conventional and super-resolution microscopy of biological samples, although the variety of the useful dyes is limited. We describe the synthesis of rhodamine-based fluorescent dyes with absorption and emission maxima in the range of 621637 and 644660 nm, respectively and demonstrate their high performance in confocal and stimulated emission depletion (STED) microscopy. New dyes were prepared by means of reliable chemical transformations applied to a rhodamine scaffold with three variable positions. They feature polarity, water solubility, variable net charges, improved stabilities of N-hydroxysuccinimidyl (NHS) esters, as well as large fluorescence quantum yields in dye solutions and antibody conjugates. The photophysical and imaging properties of dyes containing three different polar groups, namely primary phosphate, sulfonic acid (in two different positions), and hydroxyl were compared. A dye with two primary phosphate groups was explored as a valuable alternative to dyes with classical sulfonic acid groups. Due to the increased net charge of the phosphorylated dye (q=-4 at pH 8), it demonstrated a far better electrophoretic mobility compared with analogues with two sulfonic acid groups (q=-2). As an example, one fluorescent dye was designed to be especially convenient for practical use. It is characterized by sufficiently high chemical stability of the NHS ester, its simple isolation, handling, and solubility in aqueous buffers, as well as in organic solvents. All these features, accompanied by a zero net charge in conjugates, were accomplished by the introduction of hydrophilic groups of two types: two hydroxyl groups and one sulfonic acid residue. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim [accessed 2013 November 18th]