Near-infrared probes based on fluorinated Si-rhodamine for live cell imaging

Shen, Suxia; Yu, Jingru; Lu, Yaomin; Zhang, Shuchen; Yi, Xuegang; Gao, Baoxiang

doi:10.1039/c6ra28455h

Cited by 9 publications

(8 citation statements)

References 47 publications

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“…Another typical approach to avoid the ICT state formation is the introduction of cyclic substituents at the nitrogen atom . This approach was achieved in the design of a wide range of the fluorescent dyes , . Probably, the introduction of such small cycles impedes the changes of the angle between the C–N–C atoms in the amino group, which affects the formation of the ICT state .…”

Section: Resultsmentioning

confidence: 99%

The Role of N‐Substituents in Radiationless Deactivation of Aminated Derivatives of a Locked GFP Chromophore

et al. 2017

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We report the creation of a novel group of the ABDI‐BF2 fluorescent dyes based on the conformationally locked GFP chromophore. We studied the intramolecular mechanism of radiationless deactivation of the ABDI‐BF2 fluorophore by introducing the various substituents at the nitrogen atom. The results of this study and our previous work allowed us to claim that in case of ABDI‐BF2 this deactivation is determined by the formation of the nonfluorescent internal charge transfer exited state with a planar quinoidal structure. The electronic effects have a greater impact on the radiationless deactivation than the conformation. Thus, the introduction of an electron‐donating group is more effective than the creation of rigid derivatives. The presented dyes are characterized by high fluorescence quantum yields and pH‐independence in the physiological pH range, making them promising candidates for a wide spectrum of fluorescence labeling applications.

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Section: Resultsmentioning

confidence: 99%

The Role of N‐Substituents in Radiationless Deactivation of Aminated Derivatives of a Locked GFP Chromophore

et al. 2017

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“…A fluorinated Si-rhodamine is observed to have redshifted absorption spectra over the nonfluorinated compounds [ 46 ]. In Scheme 7 , the Si-rhodamine is synthesized with a phenyl ring containing a trifluoromethyl substituent compared to a similar dye with a methyl substituent.…”

Section: Fluorinated Rhodamine Based Dyesmentioning

confidence: 99%

“…Table 2 highlights the bathochromic shifts presented by the different fluorinated rhodamine dyes. Some of the most popular modifications made to the rhodamine structure are the addition of alkyl groups to the nitrogen of rhodamine, most commonly adding an azetidine ring or fluorine-containing alkyl groups as seen in compounds 38 – 40 [ 42 , 43 , 46 ]. Fluorine atoms are also typically incorporated into the rhodamine structure on the carbon adjacent to the amino group like in compound 29 , or on the phenyl ring added by the phthalic anhydride precursor as shown in compound 48 or 50 .…”

Section: Fluorinated Rhodamine Based Dyesmentioning

confidence: 99%

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Synthesis and Applications of Selected Fluorine-Containing Fluorophores

Casa

Henary

2021

Molecules

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The synthesis of fluorine-containing small molecules has had numerous benefits of improving the quality and efficiency of many applications of these compounds. For example, fluorine adds promising functionalities in various areas of imaging (MRI, PET, and NIR); gives cell-targeting properties; and has demonstrated improvements in cell permeability, solubility, and other pharmacologic properties. For these and other numerous reasons, fluorination of molecules has grown in popularity in various fields of chemistry. Many reports show the effects observed from increasing the number of fluorine atoms on a fluorophore scaffold. This report will cover the most significant applications and improvements that fluorine has contributed to in various dye scaffolds such as BODIPY, rhodamine, phthalocyanine, and cyanine in the recent decade.

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“…Recently, after replacing the 10th oxygen atom of the xanthene moiety with a SiMe 2 group, a new class of NIR fluorophores (silicon-rhodamine, SiR) was developed. − These highly permeable and biocompatible SiR probes are especially useful for bioimaging applications. − However, these fluorescent rhodamines are cationic conjugated compounds, in which the nucleophilic attack on the ninth carbon atom of the xanthene occurs easily and induces drastic changes to the optical properties. , The replacement of the N,N-dimethyl amino groups of the classic rhodamine with four-membered azetidines or tert-alkylamino groups yields a new generation of rhodamine probe with a significant increase in brightness and photostability. , Stefan W. Hell and co-workers reported that the fluorinated silicon-rhodamines possess high photostability and high fluorescence quantum yields in water . Our previous work demonstrated that the Si-rhodamine dyes with a trifluoromethyl at the 2-position of the pendant phenyl ring retains high brightness and excellent stability . Here, we report the development of NIR emission Si-rhodamine dyes (SiRMO) with the methoxy groups in the ortho-position of the benzene moiety (Chart ).…”

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confidence: 99%

Improving Brightness and Stability of Si-Rhodamine for Super-Resolution Imaging of Mitochondria in Living Cells

et al. 2020

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Photostable and bright organic dyes emitting in the near-infrared region are highly desirable for long-term dynamic bioimaging. Herein, we report a synthetic approach to build novel methoxy modified Si-rhodamine (SiRMO) dyes by introducing the methoxybenzene on the xanthene moiety. The brightness of SiRMO increased from 2300 M–1 cm–1 (SiRMO-0) to 49000 M–1 cm–1 (SiRMO-2) when the substituent 2,5-dimethoxybenzene was replaced with 2,6-dimethoxybenzene. Moreover, the stability of SiRMO-2 was significantly improved due to the steric hindrance protection of the two methoxy groups on the ninth carbon atom of the xanthene. After fast cellular uptake, the SiRMO dyes selectively stained the mitochondria with a low background in live cultured cells and primary neurons. The high brightness and stability of SiRMO-2 significantly improved the capability of monitoring mitochondria dynamic processes in living cells under super-resolution conditions. Moreover, with the fluorescence nanoscopy techniques, we observed the structure of mitochondrial cristae and mitochondria fission, fusion, and apoptosis with a high temporal resolution. Under two-photon illumination, SiRMO-2 showed also enhanced two-photon brightness and stability, which are important for imaging in thick tissue.

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Near-infrared probes based on fluorinated Si-rhodamine for live cell imaging

Abstract: Si-rhodamine probe with a trifluoromethyl group on the 2-position of the pendant phenyl ring retains high brightness and excellent stability in a harsh physiological environment.

Cited by 9 publications

References 47 publications

The Role of N‐Substituents in Radiationless Deactivation of Aminated Derivatives of a Locked GFP Chromophore

The Role of N‐Substituents in Radiationless Deactivation of Aminated Derivatives of a Locked GFP Chromophore

Synthesis and Applications of Selected Fluorine-Containing Fluorophores

Improving Brightness and Stability of Si-Rhodamine for Super-Resolution Imaging of Mitochondria in Living Cells

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