5418-63-3Relevant articles and documents
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 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.
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 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[
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
A new ratiometric fluorescence assay based on resonance energy transfer between biomass quantum dots and organic dye for the detection of sulfur dioxide derivatives
Zhao, Jingjin,Peng, Yao,Yang, Keqin,Chen, Yunyun,Zhao, Shulin,Liu, Yi-Ming
, p. 41955 - 41961 (2019)
Sulfur dioxide (SO2) is considered as the fourth gas signal molecule after nitric oxide (NO), carbon monoxide (CO) and hydrogen sulfide (H2S). It plays important roles in several physiological processes. Therefore, the design and syn
A mitochondrial-targeted ratiometric probe for detecting intracellular H2S with high photostability
Bu, Dandan,Wang, Yuying,Wu, Na,Feng, Wei,Wei, Donghui,Li, Zhanxian,Yu, Mingming
, p. 1799 - 1802 (2021)
Based on 4-bromo-1,8-naphthalic anhydride, one novel ratiometric fluorescence H2S-probe (IDNA) was designed and synthesized. Further studies indicate that IDNA can sensitively recognize H2S (detection limit of 7 μmol/L) with good selectivity and anti-interference ability. In addition, IDNA has satisfactory photostability in HeLa cells, ability of mitochondrial co-localization, and can be utilized in fluorescence imaging of H2S.
A mitochondria-targeted fluorescent dye naphthalimide-thioether-cyanine for NIR-activated photodynamic treatment of cancer cells
Shen, Ronghua,Bai, Jin,Qian, Ying
, p. 2462 - 2468 (2021/03/23)
In this work, an NIR-activated fluorescent dye naphthalimide-thioether-cyanine (NPSCY) was developed for the photodynamic treatment of cancer cells. In this dye, naphthalimide and cyanine were selected as the two fluorophores, which were linked by the thioether group. Under 660 nm irradiation,NPSCYcould produce1O2rapidly, suggesting the potential for photodynamic therapy. Cys can be considered as one of the markers of cancer cells andNPSCYcould distinguish Cys from three channels (433 nm, 475 nm, 733 nm) due to the bilateral recognition of the thioether group, which was helpful for accurately locating cancer cells. Fortunately,NPSCYcould also produce1O2after being reacted with the intracellular biological thiols, which also avoided the inactivation of the photosensitizer in cancer cells. The co-localization coefficient of 0.873 indicated that the cyanine group promoted the aggregation ofNPSCYin mitochondria. This photosensitizer showed low dark toxicity and high phototoxicity. Meanwhile, the half-maximal inhibitory concentration (IC50) was calculated to be 3.7 μM.NPSCYcould inhibit cell migration after irradiation at 660 nm.
Generalizable synthesis of bioresponsive near-infrared fluorescent probes: Sulfonated heptamethine cyanine prototype for imaging cell hypoxia
Atkinson, Kirk M.,Morsby, Janeala J.,Kommidi, Sai Shradha Reddy,Smith, Bradley D.
supporting information, p. 4100 - 4106 (2021/05/19)
Continued advancement in bioresponsive fluorescence imaging requires new classes of activatable fluorescent probes that emit near-infrared fluorescence with wavelengths above 740 nm. Heptamethine cyanine dyes (Cy7) have suitable fluorescence properties bu
