5418-63-3Relevant academic research and scientific papers
A mitochondria-selective near-infrared-emitting fluorescent dye for cellular imaging studies
Choi, Peter,Noguchi, Katsuya,Ishiyama, Munetaka,Denny, William A.,Jose, Jiney
, p. 2013 - 2017 (2018)
This communication details the synthesis, evaluation of photophysical properties, and cellular imaging studies of cyanine chromophore based fluorescent dye 1 as a selective imaging agent for mitochondria.
A highly selective and reversible fluorescent Cu2+ and S2- probe under physiological conditions and in live cells
Zhou, Quan,Zhu, Yong,Sheng, Pengtao,Wu, Zeming,Cai, Qingyun
, p. 46951 - 46954 (2014)
A new spiropyran functionalized rhodamine derivative RB-SP2 has been synthesized and applied to detect Cu2+ and S2-. RB-SP2 was then used as an imaging probe for detection of these ions in HeLa cells at the physiological pH. This jou
A study of dye anchoring points in half-squarylium dyes for dye-sensitized solar cells
Connell, Arthur,Holliman, Peter J.,Davies, Matthew L.,Gwenin, Christopher D.,Weiss, Sophie,Pitak, Mateusz B.,Horton, Peter N.,Coles, Simon J.,Cooke, Graeme
, p. 4055 - 4066 (2014)
This paper reports the synthesis of a series of new half-squaraine dyes (Hf-SQ) based around a common chromophoric unit consisting of linked indoline and squaric acid moieties. Carboxylate groups have been incorporated onto this core structure at four different points to study the influence of the anchoring group position on dye-sensitized solar cell (DSC) device performance. Dyes have been linked to TiO2 directly through the squaric acid moiety, through a modified squaric acid unit where a vinyl dicyano group has replaced one carbonyl, via an alkyl carboxylate attached to the indole N or through a carboxylate attached to the 4 position of a benzyl indole. Contact angle measurements have been studied to investigate the hydrophobic/hydrophilic properties of the dyes and the results have been compared to N719 and Z907. Full characterization data of all the dyes and synthetic intermediates are reported including single-crystal X-ray structural analysis for dye precursors; the indole (2a) and the half-squarylium esters (3a) and (6b), as well as the dyes (4c), (8) and (12). Dye colours range from yellow to red/brown in solution (λmax range from 430 to 476 nm) with ε ranging from 38000 to 133 p;100 M-1 cm-1. The performance of the dyes in DSCs shows the highest efficiency yet reported for a Hf-SQ dye (η = 5.0%) for 1 cm2 devices with a spectral response ranging from 400 to 700 nm depending on the dye substituents. Co-sensitization of half-squarylium dye (7b) with squaraine dye (SQ2) resulted in a broader spectral response and an improved device efficiency (η = 6.1%). Density functional theory (DFT) calculations and cyclic voltammetry have been used to study the influence of linker position on dye HOMO-LUMO levels and the data has been correlated with I-V and EQE data.
A series of water-soluble A-π-A′ typological indolium derivatives with two-photon properties for rapidly detecting HSO3-/SO32- in living cells
Zhu, Yingzhong,Du, Wei,Zhang, Mingzhu,Xu, Ying,Song, Leilei,Zhang, Qiong,Tian, Xiaohe,Zhou, Hongping,Wu, Jieying,Tian, Yupeng
, p. 3862 - 3869 (2017)
It is believed that HSO3- and SO32- play important roles in several physiological processes. However, probes with two-photon absorption to detect HSO3- or SO32- in living cells are still limited. Herein, a series of novel indolium derivatives (L1-L4) with an A-π-A′ structure was designed and synthesized as ratiometric probes to detect HSO3-/SO32-in vitro. L3 and L4 display a colorimetric and ratiometric fluorescence dual response to HSO3-/SO32- with a very fast (～15 s) and high specificity, as well as low detection limits (～22 nM). Furthermore, their detection is also carried out by using a two-photon excited fluorescence method. A nucleophilic addition reaction is proposed for the sensing mechanism, which is supported by MS, 1H NMR, and density functional theory (DFT) investigations. Importantly, L3 was successfully used for detecting intrinsically generated intracellular HSO3-/SO32- in cancerous cells under one- and two-photon excited fluorescence imaging.
Phospholipid-Biomimetic Fluorescent Mitochondrial Probe with Ultrahigh Selectivity Enables in Situ and High-Fidelity Tissue Imaging
Zhang, Ruoyao,Sun, Yuming,Tian, Minggang,Zhang, Ge,Feng, Ruiqing,Li, Xuechen,Guo, Lifang,Yu, Xiaoqiang,Sun, Jing Zhi,He, Xiuquan
, p. 6575 - 6582 (2017)
In situ and directly imaging mitochondria in tissues instead of isolated cells can offer more native and accurate information. Particularly, in the clinical diagnose of mitochondrial diseases such as mitochondrial myopathy, it is a routine examination item to directly observe mitochondrial morphology and number in muscle tissues from patients. However, it is still a challenging task because the selectivity of available probes is inadequate for exclusively tissue imaging. Inspired by the chemical structure of amphiphilic phospholipids in mitochondrial inner membrane, we synthesized a phospholipid-biomimetic amphiphilic fluorescent probe (Mito-MOI) by modifying a C18-alkyl chain to the lipophilic side of carbazole-indolenine cation. Thus, the phospholipid-like Mito-MOI locates at mitochondrial inner membrane through electrostatic interaction between its cation and inner membrane negative charge. Simultaneously, the C18-alkyl chain, as the second targeting group, is deeply embedded into the hydrophobic region of inner membrane through hydrophobic interaction. Therefore, the dual targeting groups (cation and C18-alkyl chain) actually endow Mito-MOI with ultrahigh selectivity. As expected, high-resolution microscopic photos showed that Mito-MOI indeed stained mitochondrial inner membrane. Moreover, in situ and high-fidelity tissue imaging has been achieved, and particularly, four kinds of mitochondria and their crystal-like structure in muscle tissues were visualized clearly. Finally, the dynamic process of mitochondrial fission in living cells has been shown. The strategy employing dual targeting groups should have reference value for designing fluorescent probes with ultrahigh selectivity to various intracellular membranous components.
A mitochondria-targeted colorimetric and ratiometric fluorescent probe for biological SO2 derivatives in living cells
Liu, Yu,Li, Kun,Wu, Ming-Yu,Liu, Yan-Hong,Xie, Yong-Mei,Yu, Xiao-Qi
, p. 10236 - 10239 (2015)
A ratiometric fluorescent probe for SO2 derivatives based on the conjugate of carbazole and indolium was presented, which could selectively respond to HSO3- over other thiol compounds. More importantly, CZ-Id is a novel mitochondria-targeted ratiometric fluorescent probe to image exogenous SO2 derivatives.
A hemicyanine and cucurbit[n]uril inclusion complex: competitive guest binding of cucurbit[7]uril and cucurbit[8]uril
Xu, Weitao,Kan, Jinglan,Redshaw, Carl,Bian, Bing,Fan, Ying,Tao, Zhu,Xiao, Xin
, p. 457 - 465 (2019)
The interaction between the hemicyanine indole derivative H and the cucubit[n]urils Q[7] and Q[8] has been studied using 1H NMR and UV spectroscopy as well as by fluorescence experiments. Competitive studies on the inclusion of H by Q[7] and Q[
Substituent effect on the acid-induced isomerization of spiropyran compounds
Cui, Lixia,Zhang, Honghong,Zhang, Guomei,Zhou, Ying,Fan, Li,Shi, Lihong,Zhang, Caihong,Shuang, Shaomin,Dong, Chuan
, p. 13 - 17 (2018)
Spiropyran compounds are well known as an isomeric system, the closed spiropyran (SP) could be converted into the open merocyanine (MC) via acid-induced because stable protonated merocyanine (MCH) were formed by combination of MC and H+. In ord
A “turn-on” near-infrared fluorescent probe with high sensitivity for detecting reduced glutathione based on red shift in vitro and in vivo
Wang, Kaiping,Nie, Gang,Ran, Siqi,Wang, Huiling,Liu, Xiqiu,Zheng, Ziming,Zhang, Yu
, (2020)
Fluorescence imaging has become a powerful tool for detecting reduced glutathione (GSH) to comprehend the physiological and pathological roles of GSH and the potential clinical diagnosis of GSH-related diseases, such as AIDS, liver damage, cancer, and leu
Cyanine-based Fluorescent Probe for Cyanide Ion Detection
Gosi, Mahesh,Marepu, Nagaraju,Sunandamma, Yeturu
, p. 1409 - 1415 (2021)
Cyanine-based probe-possessing indolium iodide and indole unit were synthesized in two-step with easy available raw material: a potential probe for the cyanide ion detection. The detecting ability of the probe was investigated and confirmed by a visual and instrumental approach. A noticeable color change from orange to colorless obtained only for cyanide ions and other added ions does not impart any changes visually and through UV and Fluorescence technique. To confirm the mechanism of sensing 1H-NMR recorded. From the result, the peak belonging to?N-methyl displayed an upfield shift from 4.01 δ ppm to 2.74 δ ppm due to the disappearance of indolium iodide ion and the olefin protons peaks were shifted from 7.19 to 6.17 and 8.70 to 7.20 δ ppm confirms the nucleophilic addition of cyanide ion to the probe. Test kit from filter paper prepared for the real-time monitoring cyanide ion. The prepared strip is effective in detecting cyanide ion with a visual color change.
