Abstract
AbstractHydroxylated rhodamines, carbopyronines, silico‐ and germanorhodamines with absorption maxima in the range of 530–640 nm were prepared and applied in specific labeling of living cells. The direct and high‐yielding entry to germa‐ and silaxanthones tolerates the presence of protected heteroatoms and may be considered for the syntheses of various sila‐ and germafluoresceins, as well as ‐rhodols. Application in stimulated emission depletion (STED) fluorescence microscopy revealed a resolution of 50–75 nm in one‐ and two‐color imaging of vimentin‐HaloTag fused protein and native tubulin. The established structure–property relationships allow for prediction of the spectral properties and the positions of spirolactone/zwitterion equilibria for the new analogues of rhodamines, carbo‐, silico‐, and germanorhodamines using simple additive schemes.
🔬 Techniques
🧬 Organisms
✨ Fluorophores
🔬 Cell Lines
🏛️ Research Organizations (ROR)
Affiliated research institutions:
📊 Figures
Figure 1
Membraneu2010permeant and fluorescent rhodamines ( R ), carbopyronines ( CP ), silicou2010 ( SiR ) or germanorhodamines ( GeR ) designed for STED microscopy of living cells (in free dyes, R=OH; in dye...
Scheme 1
a)u2005Synthesis of the bisu2010hydroxylated rhodamine dye 530RH (an analog of Rh Q u2010CO 2 H). b)u2005Synthesis of hydroxylated ROX dyes (6u2010COOHu2010Xu2010Rhodamines) 575RH ( 13u2009a ) and 13u...
Scheme 2
Synthesis of GeR and SiR dyes. a) n BuLi, u221278u2009u00b0C, then Me 2 GeCl 2 or Me 2 SiCl 2 ; b)u2005NBS; c) n BuLi or t BuLi, u221278u2009u00b0C, then Me 2 NCOCl; d) 20 , t BuLi (2u2005equiv), u221...
Figure 2
Normalized extinction u03f5 / u03f5 max at u03bb max of the dyes from Table 1 versus dielectric constant D of dioxaneu2013water mixtures ( 575RH and 6u2010ROX are unresponsive and are not included). T...
Figure 3
Twou2010color STED image (raw data) of vimentinu2010HaloTag fusion protein (green; labeled with 1u2005u03bc m 575RH u2010Halo) and endogeneous tubulin (magenta; labeled with 5u2005u03bc m GeR u2010tub...
Figure 4
An example of normal cell division (2u2005min between images) in the presence of 640SiRH bound to CIDu2010SNAP and 580R bound to CAL1u2010Halo after incubation with 0.4u2005u03bc m 580R u2010Halo 1a (...
Scheme 3
Three reference dyes (A, M, N) are chosen in such a way that M and N differ from the unknown dye X in one structural element. Dyeu2005A has one common structural element with dyeu2005M, and another co...
Figure images are served from the NIH/NLM PubMed Central Open Access Subset or Europe PMC; copyright remains with the publishers and authors.
💬 Discussion
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