Kolmakov, Kirill

[["dc.bibliographiccitation.firstpage","337"],["dc.bibliographiccitation.issue","2"],["dc.bibliographiccitation.journal","European Journal of Organic Chemistry"],["dc.bibliographiccitation.lastpage","349"],["dc.bibliographiccitation.volume","2015"],["dc.contributor.author","Mitronova, Gyuzel Yu"],["dc.contributor.author","Polyakova, Svetlana"],["dc.contributor.author","Wurm, Christian Andreas"],["dc.contributor.author","Kolmakov, Kirill"],["dc.contributor.author","Wolfram, Thomas"],["dc.contributor.author","Meineke, Dirk N. H."],["dc.contributor.author","Belov, Vladimir N."],["dc.contributor.author","John, Michael"],["dc.contributor.author","Hell, Stefan"],["dc.date.accessioned","2017-09-07T11:44:46Z"],["dc.date.available","2017-09-07T11:44:46Z"],["dc.date.issued","2015"],["dc.description.abstract","Aromatic nucleophilic substitution (SNAr) of fluorine in 9-(3'-carboxy-4',5',6',7'-tetrafluorophenyl) groups of xanthene dyes constitutes a powerful tool in dye design. Thiols and amines regioselectively replace F-6'. This approach enables additional hydrophilic residues or functional groups required for bioconjugation to be introduced. By using this methodology, a \"bright\" and photostable dye for two-color superresolution microscopy was synthesized (with absorption and emission maxima at 604 and 627 nm, respectively). In the case of red-emitting rhodamine dyes with 3'-carboxy-4',5',7'-trifluorophenyl residues, two-dimensional NMR techniques and a chemical transformation were used to prove the precise position of the additional substituent - a carboxylic acid group linked through the S-atom at C-6'. Furthermore, simple H-1 NMR spectra reliably permit the position of the additional carboxy substituent in the 3'-carboxyphenyl ring (at C-5' or C-6') to be established. Information on the exact position of this substituent is significant for the design of molecular probes and for the prediction of the properties of their bioconjugates."],["dc.identifier.doi","10.1002/ejoc.201403269"],["dc.identifier.gro","3141988"],["dc.identifier.isi","000347722900011"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/3301"],["dc.language.iso","en"],["dc.notes.intern","WoS Import 2017-03-10"],["dc.notes.status","final"],["dc.notes.submitter","PUB_WoS_Import"],["dc.relation.eissn","1099-0690"],["dc.relation.issn","1434-193X"],["dc.title","Functionalization of the meso-Phenyl Ring of Rhodamine Dyes Through SNAr with Sulfur Nucleophiles: Synthesis, Biophysical Characterizations, and Comprehensive NMR Analysis"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.subtype","original"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","522"],["dc.bibliographiccitation.issue","3"],["dc.bibliographiccitation.journal","Photochemical & Photobiological Sciences"],["dc.bibliographiccitation.lastpage","532"],["dc.bibliographiccitation.volume","11"],["dc.contributor.author","Kolmakov, Kirill"],["dc.contributor.author","Wurm, Christian Andreas"],["dc.contributor.author","Sednev, Maksim V."],["dc.contributor.author","Bossi, Mariano L."],["dc.contributor.author","Belov, Vladimir N."],["dc.contributor.author","Hell, Stefan"],["dc.date.accessioned","2017-09-07T11:43:09Z"],["dc.date.available","2017-09-07T11:43:09Z"],["dc.date.issued","2012"],["dc.description.abstract","Caged near-IR emitting fluorescent dyes are in high demand in optical microscopy but up to now were unavailable. We discovered that the combination of a carbopyronine dye core and a photosensitive 2-diazo-1-indanone residue leads to masked near-IR emitting fluorescent dyes. Illumination of these caged dyes with either UV or visible light (lambda < 420 nm) efficiently generates fluorescent compounds with absorption and emission at 635 nm and 660 nm, respectively. A high-yielding synthetic route with attractive possibilities for further dye design is described in detail. Good photostability, high contrast, and a large fluorescence quantum yield after uncaging are the most important features of the new compounds for non-invasive imaging in high-resolution optical microscopy. For use in immunolabelling the caged dyes were decorated with a (hydrophilic) linker and an (activated) carboxyl group."],["dc.identifier.doi","10.1039/c1pp05321c"],["dc.identifier.gro","3142604"],["dc.identifier.isi","000300991600012"],["dc.identifier.pmid","22218703"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/27"],["dc.language.iso","en"],["dc.notes.intern","WoS Import 2017-03-10 / Funder: Bundesministerium fur Bildung und Forschung (BMBF) [513, FKZ 13N11066]"],["dc.notes.status","final"],["dc.notes.submitter","PUB_WoS_Import"],["dc.relation.eissn","1474-9092"],["dc.relation.issn","1474-905X"],["dc.title","Masked red-emitting carbopyronine dyes with photosensitive 2-diazo-1-indanone caging group"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.subtype","original"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","158"],["dc.bibliographiccitation.issue","1"],["dc.bibliographiccitation.journal","Chemistry - A European Journal"],["dc.bibliographiccitation.lastpage","166"],["dc.bibliographiccitation.volume","16"],["dc.contributor.author","Kolmakov, Kirill"],["dc.contributor.author","Belov, Vladimir N."],["dc.contributor.author","Bierwagen, Jakob"],["dc.contributor.author","Ringemann, Christian"],["dc.contributor.author","Müller, Veronika"],["dc.contributor.author","Eggeling, Christian"],["dc.contributor.author","Hell, Stefan"],["dc.date.accessioned","2017-09-07T11:46:10Z"],["dc.date.available","2017-09-07T11:46:10Z"],["dc.date.issued","2010"],["dc.description.abstract","Fluorescent markers emitting in the red are extremely valuable in biological microscopy since they minimize cellular autofluorescence and increase flexibility in multicolor experiments. Novel rhodamine dyes excitable with 630 nm laser light and emitting at around 660 nm have been developed. The new rhodamines are very photostable and have high fluorescence quantum yields of up to 80%. long excited state lifetimes of 3.4 ns, and comparatively low intersystem-crossing rates. They perform very well both in conventional and in subdiffraction-resolution microscopy such as STED (stimulated emission depletion) and GSDIM (ground-state depletion with individual molecular return), as well as in single-molecule-based experiments such as fluorescence correlation spectroscopy (FCS). Syntheses of lipophilic and hydrophilic derivatives starting from the same chromophore-containing scaffold are described. Introduction of two sulfo groups provides high solubility in water and a considerable rise in fluorescence quantum yield. The attachment of amino or thiol reactive groups allows the dyes to be used as fluorescent markers in biology. Dyes deuterated at certain positions have narrow and symmetrical molecular mass distribution patterns, and are proposed as new tags in MS or LC-MS for identification and quantification of various substance classes (e.g., amines and thiols) in complex mixtures. High-resolution GSDIM images and live-cell STED-FCS experiments on labeled microtubules and lipids prove the versatility of the novel probes for modern fluorescence microscopy and nanoscopy."],["dc.identifier.doi","10.1002/chem.200902309"],["dc.identifier.gro","3142991"],["dc.identifier.isi","000274007900019"],["dc.identifier.pmid","19950338"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/455"],["dc.language.iso","en"],["dc.notes.intern","WoS Import 2017-03-10"],["dc.notes.status","final"],["dc.notes.submitter","PUB_WoS_Import"],["dc.relation.issn","0947-6539"],["dc.title","Red-Emitting Rhodamine Dyes for Fluorescence Microscopy and Nanoscopy"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.subtype","original"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","3593"],["dc.bibliographiccitation.issue","19"],["dc.bibliographiccitation.journal","European Journal of Organic Chemistry"],["dc.bibliographiccitation.lastpage","3610"],["dc.bibliographiccitation.volume","2010"],["dc.contributor.author","Kolmakov, Kirill"],["dc.contributor.author","Belov, Vladimir N."],["dc.contributor.author","Wurm, Christian Andreas"],["dc.contributor.author","Harke, Benjamin"],["dc.contributor.author","Leutenegger, Marcel"],["dc.contributor.author","Eggeling, Christian"],["dc.contributor.author","Hell, Stefan"],["dc.date.accessioned","2017-09-07T11:45:57Z"],["dc.date.available","2017-09-07T11:45:57Z"],["dc.date.issued","2010"],["dc.description.abstract","Biological microscopy favors photostable fluorescent markers with large fluorescence quantum yields, low dark triplet state population, good biocompatibility and absorption and emission maxima in the near-infrared, where cellular autofluorescence is minimized. In the present study, carbopyronines absorbing around 640 nm and emitting at around 660 nm, with a low intersystem crossing rate (k(isc) approximate to 0.5 X 10(6) s(-1)) and excellent properties for cellular imaging were synthesized. A general synthetic route to carbopyronines with functional groups variable in the final steps of the synthesis or in the resulting fluorescent dye is presented. Possessing two 2-methoxyethyl groups, the parent dye is soluble in water and most organic solvents. Demethylation of the dye or its precursors is straightforward, clean, and furnishes compounds with one or two 2-hydroxyethyl groups, which can be used for further transformations. Modifications in the linker-containing carboxy group are also possible. A multistep synthesis of the dye starting from a simple precursor and utilizing a single temporary protective group is described. The presented approach may be further applied to the design of caged carbopyronines."],["dc.identifier.doi","10.1002/ejoc.201000343"],["dc.identifier.gro","3142895"],["dc.identifier.isi","000280220800007"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/350"],["dc.language.iso","en"],["dc.notes.intern","WoS Import 2017-03-10 / Funder: Deutsche Forschungsgemeinschaft (DFG); Max-Planck-Gesellschaft"],["dc.notes.status","final"],["dc.notes.submitter","PUB_WoS_Import"],["dc.relation.issn","1434-193X"],["dc.title","A Versatile Route to Red-Emitting Carbopyronine Dyes for Optical Microscopy and Nanoscopy"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.subtype","original"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.artnumber","7"],["dc.bibliographiccitation.firstpage","1"],["dc.bibliographiccitation.issue","1"],["dc.bibliographiccitation.journal","Optical Nanoscopy"],["dc.bibliographiccitation.lastpage","7"],["dc.bibliographiccitation.volume","1"],["dc.contributor.author","Wurm, Christian Andreas"],["dc.contributor.author","Kolmakov, Kirill"],["dc.contributor.author","Göttfert, Fabian"],["dc.contributor.author","Ta, Haisen"],["dc.contributor.author","Bossi, Mariano"],["dc.contributor.author","Schill, Heiko"],["dc.contributor.author","Berning, Sebastian"],["dc.contributor.author","Jakobs, Stefan"],["dc.contributor.author","Donnert, Gerald"],["dc.contributor.author","Belov, Vladimir N."],["dc.contributor.author","Hell, Stefan W."],["dc.date.accessioned","2017-09-07T11:53:03Z"],["dc.date.available","2017-09-07T11:53:03Z"],["dc.date.issued","2012"],["dc.description.abstract","In optical microscopy, most red-emitting dyes provide only moderate performance due to unspecific binding, poor labeling efficiency, and insufficient brightness. Here we report on four novel red fluororescent dyes, including the first phosphorylated dye, created by combining a rigidized rhodamine backbone with various polar groups. They exhibit large fluorescence quantum yields and improved NHS ester stability. While these fluorophores are highly suitable for fluorescence microscopy in general, they excel in stimulated emission depletion (STED) microscopy, providing < 25 nm spatial resolution in raw images of cells."],["dc.identifier.doi","10.1186/2192-2853-1-7"],["dc.identifier.fs","593636"],["dc.identifier.gro","3145019"],["dc.identifier.purl","https://resolver.sub.uni-goettingen.de/purl?gs-1/8898"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/2709"],["dc.language.iso","en"],["dc.notes.intern","Crossref Import"],["dc.notes.intern","Merged from goescholar"],["dc.notes.status","final"],["dc.relation.issn","2192-2853"],["dc.relation.orgunit","Fakultät für Physik"],["dc.rights","Goescholar"],["dc.rights.uri","https://goedoc.uni-goettingen.de/licenses"],["dc.title","Novel red fluorophores with superior performance in STED microscopy"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","no"],["dc.type.version","published_version"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","13162"],["dc.bibliographiccitation.issue","41"],["dc.bibliographiccitation.journal","Chemistry - A European Journal"],["dc.bibliographiccitation.lastpage","13173"],["dc.bibliographiccitation.volume","20"],["dc.contributor.author","Belov, Vladimir N."],["dc.contributor.author","Mitronova, Gyuzel Yu"],["dc.contributor.author","Bossi, Mariano L."],["dc.contributor.author","Boyarskiy, Vadim P."],["dc.contributor.author","Hebisch, Elke"],["dc.contributor.author","Geisler, Claudia"],["dc.contributor.author","Kolmakov, Kirill"],["dc.contributor.author","Wurm, Christian Andreas"],["dc.contributor.author","Willig, Katrin I."],["dc.contributor.author","Hell, Stefan"],["dc.date.accessioned","2017-09-07T11:45:27Z"],["dc.date.available","2017-09-07T11:45:27Z"],["dc.date.issued","2014"],["dc.description.abstract","Caged rhodamine dyes (Rhodamines NN) of five basic colors were synthesized and used as \"hidden\" markers in subdiffractional and conventional light microscopy. These masked fluorophores with a 2-diazo-1-indanone group can be irreversibly photoactivated, either by irradiation with UV- or violet light (one-photon process), or by exposure to intense red light (lambda-750 nm; two-photon mode). All dyes possess a very small 2-diazoketone caging group incorporated into the 2-diazo-1-indanone residue with a quaternary carbon atom (C-3) and a spiro-9H-xanthene fragment. Initially they are non-colored (pale yellow), non-fluorescent, and absorb at lambda=330-350 nm (molar extinction coefficient (epsilon) approximate to 10(4)M(-1)cm(-1)) with a band edge that extends to about lambda = 440 nm. The absorption and emission bands of the uncaged derivatives are tunable over a wide range (lambda=511-633 and 525-653 nm, respectively). The unmasked dyes are highly colored and fluorescent (epsilon = 3-8 x 10(4)M(-1)cm(-1) and fluorescence quantum yields (phi) = 40-85% in the unbound state and in methanol). By stepwise and orthogonal protection of carboxylic and sulfonic acid groups a highly water-soluble caged red-emitting dye with two sulfonic acid residues was prepared. Rhodamines NN were decorated with amino-reactive N-hydroxysuccinimidyl ester groups, applied in aqueous buffers, easily conjugated with proteins, and readily photoactivated (uncaged) with lambda = 375-420 nm light or intense red light (lambda = 775 nm). Protein conjugates with optimal degrees of labeling (3-6) were prepared and uncaged with lambda= 405 nm light in aqueous buffer solutions (phi = 20-38%). The photochemical cleavage of the masking group generates only molecular nitrogen. Some 10-40% of the non-fluorescent (dark) byproducts are also formed. However, they have low absorbance and do not quench the fluorescence of the uncaged dyes. Photoactivation of the individual molecules of Rhodamines NN (e.g., due to reversible or irreversible transition to a \"dark\" non-emitting state or photobleaching) provides multicolor images with subdiffractional optical resolution. The applicability of these novel caged fluorophores in super-resolution optical microscopy is exemplified."],["dc.identifier.doi","10.1002/chem.201403316"],["dc.identifier.gro","3142036"],["dc.identifier.isi","000342770900020"],["dc.identifier.pmid","25196166"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/3834"],["dc.language.iso","en"],["dc.notes.intern","WoS Import 2017-03-10"],["dc.notes.status","final"],["dc.notes.submitter","PUB_WoS_Import"],["dc.relation.eissn","1521-3765"],["dc.relation.issn","0947-6539"],["dc.title","Masked Rhodamine Dyes of Five Principal Colors Revealed by Photolysis of a 2-Diazo-1-Indanone Caging Group: Synthesis, Photophysics, and Light Microscopy Applications"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.subtype","original"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.issue","1"],["dc.bibliographiccitation.journal","Nature Communications"],["dc.bibliographiccitation.volume","7"],["dc.contributor.author","van der Velde, Jasper H. M."],["dc.contributor.author","Oelerich, Jens"],["dc.contributor.author","Huang, Jingyi"],["dc.contributor.author","Smit, Jochem H."],["dc.contributor.author","Aminian Jazi, Atieh"],["dc.contributor.author","Galiani, Silvia"],["dc.contributor.author","Kolmakov, Kirill"],["dc.contributor.author","Gouridis, Giorgos"],["dc.contributor.author","Eggeling, Christian"],["dc.contributor.author","Cordes, Thorben"],["dc.date.accessioned","2021-06-01T10:50:34Z"],["dc.date.available","2021-06-01T10:50:34Z"],["dc.date.issued","2016"],["dc.description.abstract","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."],["dc.identifier.doi","10.1038/ncomms10144"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/86709"],["dc.language.iso","en"],["dc.notes.intern","DOI-Import GROB-425"],["dc.relation.eissn","2041-1723"],["dc.title","A simple and versatile design concept for fluorophore derivatives with intramolecular photostabilization"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","146"],["dc.bibliographiccitation.issue","1"],["dc.bibliographiccitation.journal","Chemistry - A European Journal"],["dc.bibliographiccitation.lastpage","157"],["dc.bibliographiccitation.volume","20"],["dc.contributor.author","Kolmakov, Kirill"],["dc.contributor.author","Wurm, Christian Andreas"],["dc.contributor.author","Meineke, Dirk N. H."],["dc.contributor.author","Göttfert, Fabian"],["dc.contributor.author","Boyarskiy, Vadim P."],["dc.contributor.author","Belov, Vladimir N."],["dc.contributor.author","Hell, Stefan"],["dc.date.accessioned","2017-09-07T11:46:54Z"],["dc.date.available","2017-09-07T11:46:54Z"],["dc.date.issued","2014"],["dc.description.abstract","The synthesis, reactivity, and photophysical properties of new rhodamines with intense red fluorescence, two polar residues (hydroxyls, primary phosphates, or sulfonic acid groups), and improved hydrolytic stability of the amino-reactive sites (NHS esters or mixed N-succinimidyl carbonates) are reported. All fluorophores contain an N-alkyl-1,2-dihydro-2,2,4-trimethylquinoline fragment, and most of them bear a fully substituted tetrafluoro phenyl ring with a secondary carboxamide group. The absorption and emission maxima in water are in the range of 635-639 and 655-659nm, respectively. A vastly simplified approach to red-emitting rhodamines with two phosphate groups that are compatible with diverse functional linkers was developed. As an example, a phosphorylated dye with an azide residue was prepared and was used in a click reaction with a strained alkyne bearing an N-hydroxysuccinimid (NHS) ester group. This method bypasses the undesired activation of phosphate groups, and gives an amphiphilic amino-reactive dye, the solubility and distribution of which between aqueous and organic phases can be controlled by varying the pH. The presence of two hydroxyl groups and a phenyl ring with two carboxyl residues in the dyes with another substitution pattern is sufficient for providing the hydrophilic properties. Selective formation of a mono-N-hydroxysuccinimidyl ester from 5-carboxy isomer of this rhodamine is reported. The fluorescence quantum yields varied from 58 to 92% for free fluorophores, and amounted to 18-64% for antibody conjugates in aqueous buffers. The brightness and photostability of these fluorophores facilitated two-color stimulated emission depletion (STED) fluorescence nanoscopy of biological samples with high contrast and minimal background. Selecting a pair of fluorophores with absorption/emission bands at 579/609 and 635/655nm enabled two-color channels with low cross-talk and negligible background at approximately 40nm resolution."],["dc.identifier.doi","10.1002/chem.201303433"],["dc.identifier.gro","3142200"],["dc.identifier.isi","000328714700019"],["dc.identifier.pmid","24338798"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/5643"],["dc.language.iso","en"],["dc.notes.intern","WoS Import 2017-03-10 / Funder: Bundesministerium fur Bildung und Forschung [BMBF 513, FKZ 13N11066]"],["dc.notes.status","final"],["dc.notes.submitter","PUB_WoS_Import"],["dc.relation.eissn","1521-3765"],["dc.relation.issn","0947-6539"],["dc.title","Polar Red-Emitting Rhodamine Dyes with Reactive Groups: Synthesis, Photophysical Properties, and Two-Color STED Nanoscopy Applications"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.subtype","original"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","12986"],["dc.bibliographiccitation.issue","41"],["dc.bibliographiccitation.journal","Chemistry - A European Journal"],["dc.bibliographiccitation.lastpage","12998"],["dc.bibliographiccitation.volume","18"],["dc.contributor.author","Kolmakov, Kirill"],["dc.contributor.author","Wurm, Christian Andreas"],["dc.contributor.author","Hennig, René"],["dc.contributor.author","Rapp, Erdmann"],["dc.contributor.author","Jakobs, Stefan"],["dc.contributor.author","Belov, Vladimir N."],["dc.contributor.author","Hell, Stefan W."],["dc.date.accessioned","2017-09-07T11:48:24Z"],["dc.date.available","2017-09-07T11:48:24Z"],["dc.date.issued","2012"],["dc.description.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."],["dc.identifier.doi","10.1002/chem.201201168"],["dc.identifier.gro","3142458"],["dc.identifier.isi","000309239300013"],["dc.identifier.pmid","22968960"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/8507"],["dc.language.iso","en"],["dc.notes.intern","WoS Import 2017-03-10"],["dc.notes.status","final"],["dc.notes.submitter","PUB_WoS_Import"],["dc.relation.issn","0947-6539"],["dc.title","Red-Emitting Rhodamines with Hydroxylated, Sulfonated, and Phosphorylated Dye Residues and Their Use in Fluorescence Nanoscopy"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.subtype","original"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","13344"],["dc.bibliographiccitation.issue","38"],["dc.bibliographiccitation.journal","Chemistry - A European Journal"],["dc.bibliographiccitation.lastpage","13356"],["dc.bibliographiccitation.volume","21"],["dc.contributor.author","Kolmakov, Kirill"],["dc.contributor.author","Hebisch, Elke"],["dc.contributor.author","Wolfram, Thomas"],["dc.contributor.author","Nordwig, Lars A."],["dc.contributor.author","Wurm, Christian Andreas"],["dc.contributor.author","Ta, Haisen"],["dc.contributor.author","Westphal, Volker"],["dc.contributor.author","Belov, Vladimir N."],["dc.contributor.author","Hell, Stefan"],["dc.date.accessioned","2017-09-07T11:43:32Z"],["dc.date.available","2017-09-07T11:43:32Z"],["dc.date.issued","2015"],["dc.description.abstract","Far-red emitting fluorescent dyes for optical microscopy, stimulated emission depletion (STED), and ground-state depletion (GSDIM) super-resolution microscopy are presented. Fluorinated silicon-rhodamines (SiRF dyes) and phosphorylated oxazines have absorption and emission maxima at about approximate to 660 and 680nm, respectively, possess high photostability, and large fluorescence quantum yields in water. A high-yielding synthetic path to introduce three aromatic fluorine atoms and unconventional conjugation/solubilization spacers into the scaffold of a silicon-rhodamine is described. The bathochromic shift in SiRF dyes is achieved without additional fused rings or double bonds. As a result, the molecular size and molecular mass stay quite small (<600Da). The use of the =800nm STED beam instead of the commonly used one at =750-775nm provides excellent imaging performance and suppresses re-excitation of SiRF and the oxazine dyes. The photophysical properties and immunofluorescence imaging performance of these new far-red emitting dyes (photobleaching, optical resolution, and switch-off behavior) are discussed in detail and compared with those of some well-established fluorophores with similar spectral properties."],["dc.identifier.doi","10.1002/chem.201501394"],["dc.identifier.gro","3141827"],["dc.identifier.isi","000360829600028"],["dc.identifier.pmid","26272226"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/1512"],["dc.language.iso","en"],["dc.notes.intern","WoS Import 2017-03-10"],["dc.notes.status","final"],["dc.notes.submitter","PUB_WoS_Import"],["dc.relation.eissn","1521-3765"],["dc.relation.issn","0947-6539"],["dc.title","Far-Red Emitting Fluorescent Dyes for Optical Nanoscopy: Fluorinated Silicon-Rhodamines (SiRF Dyes) and Phosphorylated Oxazines"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.subtype","original"],["dspace.entity.type","Publication"]]