107070-67-7Relevant articles and documents
Novel rhodamine dye with large Stokes shifts by fusing the 1,4-diethylpiperazine moiety and its applications in fast detection of Cu2+
Gong, Jin,He, Song,Jiao, Xiaojie,Liu, Chang,Zeng, Xianshun,Zhao, Liancheng
, p. 38038 - 38044 (2020)
Rhodamine dyes were widely developed for designing probes due to their excellent photophysical properties and biocompatibility. However, traditional rhodamine dyes still bear major drawbacks of short emission wavelengths (600 nm) and narrow Stokes shifts (30 nm), which limit their biological imaging applications. Herein, we reported a novel mitochondria-Targeted fluorescent dye JRQ with near-infrared (NIR) emission wavelength and improved Stokes shift (63 nm) by tuning the donor-Acceptor-donor (D-A-D) character of the rhodamine skeleton. As expected, JRQ exhibited multiple excellent properties and could accumulate in mitochondria, and can therefore be used as a signal reporter for the design of fluorescent probes by taking advantage of the fluorescence controlled mechanism of the ring opening and closing chemical processes of the spirolactone platform. By using JRQ as a precursor, a highly sensitive fluorescent probe JRQN for the fast detection of mitochondrial Cu2+ ions was synthesized based on the Cu2+-Triggered specific hydrolysis mechanism because mitochondria are an important reservoir of intracellular Cu2+. We expect that the Stokes shift increase of rhodamine dyes via tuning the donor-Acceptor-donor (D-A-D) character of the rhodamine skeleton will provide a novel synthetic approach for the development of rhodamine dyes and expansion of their applications. This journal is
Deep red emitting triphenylamine based coumarin-rhodamine hybrids with large Stokes shift and viscosity sensing: Synthesis, photophysical properties and DFT studies of their spirocyclic and open forms
Kothavale, Shantaram,Jadhav, Amol G.,Sekar, Nagaiyan
, p. 329 - 341 (2017)
We designed and synthesized triphenylamine based and coumarin fused rhodamine hybrid dyes and characterized using 1H, 13C NMR and HR-LCMS analysis. Both the newly synthesized hybrid dyes were found to show red shifted absorption as well as emissions and large Stokes shift (40–68 nm) as compared to the small Stokes shift (25–30 nm) of reported dyes Rhodamine B and 101. Photophysical properties of these dyes were studied in different solvents and according to the solvents acidity or basicity they preferred to remain in their spirocyclic or open form in different ratio. We studied the spirocyclic as well as open form derivatives of these dyes for their viscosity sensitivity in three different mixture of solvents i.e. polar-protic [EtOH-PEG 400], polar-aprotic [toluene-PEG 400] and non-polar-aprotic [toluene-paraffin]. They are found to show very high viscosity sensitivity in polar-protic mixture of solvents [EtOH-PEG 400] and hence concluded that both polarity as well as viscosity factor worked together for the higher emission enhancement rather than only viscosity factor. As these dyes showed very high viscosity sensitivity in their spirocyclic as well as open form, they can be utilized as viscosity sensors in visible as well as deep red region. We also correlated our experimental finding theoretically by using Density Functional theory computations.
Synthesis and properties of seminaphthorhodafluor red laser dyes
Ming, Wei,Hu, Xiaojie,Zhang, Zhizhong,Chang, Shunzhou,Chen, Risheng,Tian, Baozhu,Zhang, Jinlong
, p. 1991 - 2002 (2020)
In the present work, we synthesized two seminaphthorhodafluor red laser dyes SNARF-X1 and SNARF-X2 and investigated their photo-physical properties in different solvents and the laser properties in ethanol. It was found that the wavelengths of absorption and fluorescence emission spectra are not very sensitive to the solvent polarity, while the fluorescence intensities decrease with the increase in solvent polarity. SNARF-X1 and SNARF-X2 not only emit tunable red laser (590–670?nm for SNARF-X1 and 600–680?nm for SNARF-X2) but also show high laser conversion efficiency. The above two dyes also show high photo-stability under 532?nm ND:YAG laser irradiation. In this regard, the half-lives of laser efficiency for SNARF-X1 and SNARF-X2 are 7?h and 6?h, respectively.
A novel near-infrared fluorescent probe with an improved Stokes shift for specific detection of Hg2+in mitochondria
Gong, Jin,He, Song,Jiao, Xiaojie,Liu, Chang,Zeng, Xianshun,Zhao, Liancheng
, p. 5238 - 5244 (2020)
The mercury ion (Hg2+), one of the most notorious heavy metal ions, not only causes environmental pollution, but also endangers human health. There is evidence that Hg2+ tends to accumulate in the mitochondria and to induce apoptosis. However, mitochondria-targeted near-infrared (NIR) fluorescent probes with large Stokes shifts are still scarcely described for the specific detection of Hg2+. In this work, a novel near-infrared fluorescent probe JRQNS with a large Stokes shift (78 nm) was reported, and applied for sensitive and specific detection of Hg2+ in mitochondria by incorporating an additional amine group with fused rings to rhodamine dyes to enhance the electron donating ability of amine groups. As expected, the probe exhibited high selectivity and sensitivity to Hg2+ with a detection limit as low as 1.5 nM and fast response times (3 min), revealing that JRQNS could be used as a practical probe for quantitative detection of Hg2+ in real-time. Importantly, JRQNS can be used as an efficient organelle-targeting probe for imaging Hg2+ in the mitochondria of living cells, and thus detect Hg2+ in real-time there. The application of the probe for its selective localization in mitochondria along with the nanomolar level of limit of detection to Hg2+ ions provided a potential tool for studying the cytotoxic mechanisms of Hg2+. This journal is
Stress response decay with aging visualized using a dual-channel logic-based fluorescent probe
Guo, Yuan,James, Tony D.,Li, Jian,Li, Xiaokang,Li, Xinming,Shi, Donglei,Teng, Hao,Tian, Jingye,Zhang, Yanhui
, p. 13483 - 13491 (2021/11/01)
Diagnosing aging for preventative intervention generally relies on the tracking of aging biomarkers in the resting state. However, the static marker levels are insufficient to fully evaluate aging, particularly given that the stress response capacity (SRC) decay is currently viewed as a critical feature of aging. Therefore, we have developed a dual-channel fluorescent probe ROKS capable of the logic-based visualization of thiophenol (stressor) and HOCl (thiophenol-activated stress response product) in vivo, which provides a new strategy from the time dimension to precisely assess the SRC of individuals under stress using the dual-channel fluorescence ratio. Using ROKS we observed that the SRC of live cells decayed with senescence, and that a higher SRC was found for young vs. aged Caenorhabditis elegans. As such, our study offers a promising strategy for the fluorescence-guided diagnosis of aging and paves the way for accurate evaluation of the efficacy of anti-aging drugs.
