- A mitochondria-selective near-infrared-emitting fluorescent dye for cellular imaging studies
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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.
- Choi, Peter,Noguchi, Katsuya,Ishiyama, Munetaka,Denny, William A.,Jose, Jiney
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- A highly selective and reversible fluorescent Cu2+ and S2- probe under physiological conditions and in live cells
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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
- Zhou, Quan,Zhu, Yong,Sheng, Pengtao,Wu, Zeming,Cai, Qingyun
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- A study of dye anchoring points in half-squarylium dyes for dye-sensitized solar cells
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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.
- Connell, Arthur,Holliman, Peter J.,Davies, Matthew L.,Gwenin, Christopher D.,Weiss, Sophie,Pitak, Mateusz B.,Horton, Peter N.,Coles, Simon J.,Cooke, Graeme
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- A series of water-soluble A-π-A′ typological indolium derivatives with two-photon properties for rapidly detecting HSO3-/SO32- in living cells
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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.
- Zhu, Yingzhong,Du, Wei,Zhang, Mingzhu,Xu, Ying,Song, Leilei,Zhang, Qiong,Tian, Xiaohe,Zhou, Hongping,Wu, Jieying,Tian, Yupeng
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- Phospholipid-Biomimetic Fluorescent Mitochondrial Probe with Ultrahigh Selectivity Enables in Situ and High-Fidelity Tissue Imaging
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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.
- Zhang, Ruoyao,Sun, Yuming,Tian, Minggang,Zhang, Ge,Feng, Ruiqing,Li, Xuechen,Guo, Lifang,Yu, Xiaoqiang,Sun, Jing Zhi,He, Xiuquan
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- A mitochondria-targeted colorimetric and ratiometric fluorescent probe for biological SO2 derivatives in living cells
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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.
- Liu, Yu,Li, Kun,Wu, Ming-Yu,Liu, Yan-Hong,Xie, Yong-Mei,Yu, Xiao-Qi
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- A hemicyanine and cucurbit[n]uril inclusion complex: competitive guest binding of cucurbit[7]uril and cucurbit[8]uril
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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[
- Xu, Weitao,Kan, Jinglan,Redshaw, Carl,Bian, Bing,Fan, Ying,Tao, Zhu,Xiao, Xin
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- Substituent effect on the acid-induced isomerization of spiropyran compounds
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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
- Cui, Lixia,Zhang, Honghong,Zhang, Guomei,Zhou, Ying,Fan, Li,Shi, Lihong,Zhang, Caihong,Shuang, Shaomin,Dong, Chuan
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- A “turn-on” near-infrared fluorescent probe with high sensitivity for detecting reduced glutathione based on red shift in vitro and in vivo
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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
- Wang, Kaiping,Nie, Gang,Ran, Siqi,Wang, Huiling,Liu, Xiqiu,Zheng, Ziming,Zhang, Yu
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- Cyanine-based Fluorescent Probe for Cyanide Ion Detection
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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.
- Gosi, Mahesh,Marepu, Nagaraju,Sunandamma, Yeturu
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- A new ratiometric fluorescence assay based on resonance energy transfer between biomass quantum dots and organic dye for the detection of sulfur dioxide derivatives
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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
- Zhao, Jingjin,Peng, Yao,Yang, Keqin,Chen, Yunyun,Zhao, Shulin,Liu, Yi-Ming
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- Neutral merocyanine dyes: For: in vivo NIR fluorescence imaging of amyloid-β plaques
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Two neutral merocyanine-based near-infrared fluorescent probes were for the first time developed through rational engineering of the classical cationic cyanine scaffold IR-780 for in vivo imaging of amyloid-β plaques. In vivo NIRF imaging revealed that the probe could penetrate the blood-brain barrier and efficiently differentiate the living transgenic and wild-type mice.
- Yan, Jin-Wu,Zhu, Jia-Ying,Zhou, Kai-Xiang,Wang, Jin-Sheng,Tan, Hui-Ya,Xu, Zhong-Yong,Chen, Shuo-Bin,Lu, Yu-Ting,Cui, Meng-Chao,Zhang, Lei
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- A mitochondrial-targeted ratiometric probe for detecting intracellular H2S with high photostability
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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.
- Bu, Dandan,Wang, Yuying,Wu, Na,Feng, Wei,Wei, Donghui,Li, Zhanxian,Yu, Mingming
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- Mitochondria-targeted fluorescent probe for rapid detection of thiols and its application in bioimaging
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Biothiols are crucial reactive sulfur species in living cells, playing an essential role in maintaining the normal function of organisms. Effective detection of biothiols promotes the exploration of metabolic pathways and physiological functions of organisms. In this paper, a cyanine-based, mitochondria-targetable fluorescent probe, Cy-DNBS, was designed and synthesized. This probe uses a lipophilic cation unit as mitochondrial targeting site and DNBS group as the fluorescence quencher as well as the recognition site. The probe shows a distinct fluorescence emission at 604 nm upon rapid interaction with intracellular biothiols, owing to the removal of the 2,4-dinitrobenzene-sulfonyl (DNBS) group and the blockage of PET process. Moreover, the probe can not only image endogenous thiols, but also efficiently target mitochondria and evaluate thiol fluctuations under mitochondrial oxidative stress induced by H2O2. Collectively, the new low cytotoxic probe can serve as a promising tool for monitoring cellular thiols and further exploring elevant disease processes.
- Zhu, Yuedong,Pan, Haiting,Song, Yanyan,Jing, Chao,Gan, Jia-An,Zhang, Junji
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- Generalizable synthesis of bioresponsive near-infrared fluorescent probes: Sulfonated heptamethine cyanine prototype for imaging cell hypoxia
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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
- Atkinson, Kirk M.,Morsby, Janeala J.,Kommidi, Sai Shradha Reddy,Smith, Bradley D.
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supporting information
p. 4100 - 4106
(2021/05/19)
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- Polymethine-Based Semiconducting Polymer Dots with Narrow-Band Emission and Absorption/Emission Maxima at NIR-II for Bioimaging
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Deep-penetration fluorescence imaging in the second near-infrared (NIR-II) window heralds a new era of clinical surgery, in which high-resolution vascular/lymphatic anatomy and detailed cancerous tissues can be visualized in real time. Described here is a series of polymethine-based semiconducting polymers with intrinsic emission maxima in the NIR-IIa (1300–1400 nm) window and absorption maxima ranging from 1082 to 1290 nm. These polymers were prepared as semiconducting polymer dots (Pdots) in aqueous solutions with fluorescence quantum yields of 0.05–0.18 %, and they demonstrate promising applications in noninvasive through-skull brain imaging in live mice with remarkable spatial resolution as well as signal-to-background contrast. This study offers a platform for future design of NIR-IIa or even NIR-IIb emitting Pdots.
- Liu, Ming-Ho,Zhang, Zhe,Yang, Yu-Chi,Chan, Yang-Hsiang
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supporting information
p. 983 - 989
(2020/11/30)
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- Fluorescent probe for gastric acid monitoring, and preparation method and application thereof
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The invention provides a fluorescent probe for gastric acid monitoring and a preparation method and application thereof. The molecular formula of the fluorescent probe is C. 34 H42 N3+ The preparation method of the fluorescent probe comprises the following steps: 2, 3, 3 - trimethyl - 3H - indole are reacted under the action of methyl iodide and ethanol, and the compound 1 is generated. A dichloromethane solution of cyclohexanone was added dropwise to N, N -dimethylformamide and dichloromethane solution of phosphorus oxychloride, and the reflux reaction was heated to give compound 2. Compound 1, Compound 2 and sodium acetate were reacted in acetic anhydride to give compound 3. The compound 3 and dimethylamine were reacted in ethanol to give a fluorescent probe. The fluorescent probe has good water solubility, and the fluorescence signal changes obviously along pH value in an aqueous solution, so that the fluorescence probe responds to pH value, can specifically detect the change of pH value, is not influenced by other molecules, and can be used for monitoring gastric acid in near-infrared fluorescence technology.
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Paragraph 0059; 0061-0064
(2021/10/05)
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- Active inorganic sulfur species two-photon fluorescent probe as well as synthesis method and application thereof
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The invention relates to an active inorganic sulfur species two-photon fluorescent probe, which takes 1-pyrenecarboxaldehyde-hemicyanine as a parent and has a structural general formula shown in the specification. The active inorganic sulfur species two-p
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Paragraph 0035-0037; 0040
(2021/03/24)
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- NOVEL SQUARYLIUM COMPOUNDS, AND COMPOSITIONS COMPRISING SAME
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The present disclosure is disclosed herein. The present invention relates to a novel squarylium compound and a near infrared absorbing resin composition containing the squarylium compound.
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Paragraph 0107; 0109; 0110; 0111
(2021/04/29)
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- A mitochondria-targeted fluorescent dye naphthalimide-thioether-cyanine for NIR-activated photodynamic treatment of cancer cells
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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.
- Shen, Ronghua,Bai, Jin,Qian, Ying
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p. 2462 - 2468
(2021/03/23)
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- Disruption of mitochondrial redox homeostasis by enzymatic activation of a trialkylphosphine probe
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Redox homeostasis is essential for cell function and its disruption is associated with multiple pathologies. Redox balance is largely regulated by the relative concentrations of reduced and oxidized glutathione. In eukaryotic cells, this ratio is different in each cell compartment, and disruption of the mitochondrial redox balance has been specifically linked to metabolic diseases. Here, we report a probe that is selectively activated by endogenous nitroreductases, and releases tributylphosphine to trigger redox stress in mitochondria. Mechanistic studies revealed that, counterintuitively, release of a reducing agent in mitochondria rapidly induced oxidative stress through accumulation of superoxide. This response is mediated by glutathione, suggesting a link between reductive and oxidative stress. Furthermore, mitochondrial redox stress activates a cellular response orchestrated by transcription factor ATF4, which upregulates genes involved in glutathione catabolism.
- Nguyen, Jade,Tirla, Alina,Rivera-Fuentes, Pablo
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supporting information
p. 2681 - 2687
(2021/04/07)
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- Near-Infrared Heptamethine Cyanine Dyes for Nanoparticle-Based Photoacoustic Imaging and Photothermal Therapy
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We have synthesized and characterized a library of near-infrared (NIR) heptamethine cyanine dyes for biomedical application as photoacoustic imaging and photothermal agents. These hydrophobic dyes were incorporated into a polymer-based nanoparticle system to provide aqueous solubility and protection of the photophysical properties of each dye scaffold. Among those heptamethine cyanine dyes analyzed, 13 compounds within the nontoxic polymeric nanoparticles have been selected to exemplify structural relationships in terms of photostability, photoacoustic imaging, and photothermal behavior within the NIR (~650-850 nm) spectral region. The most contributing structural features observed in our dye design include hydrophobicity, rotatable bonds, heavy atom effects, and stability of the central cyclohexene ring within the dye core. The NIR agents developed within this project serve to elicit a structure-function relationship with emphasis on their photoacoustic and photothermal characteristics aiming at producing customizable NIR photoacoustic and photothermal tools for clinical use.
- St. Lorenz, Anna,Buabeng, Emmanuel Ramsey,Taratula, Oleh,Taratula, Olena,Henary, Maged
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p. 8798 - 8805
(2021/06/28)
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- Near infrared ratio fluorescent probe for detecting nitroreductase as well as preparation method and application thereof (by machine translation)
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The invention discloses a novel near-infrared ratio fluorescent probe for detecting nitroreductase and a preparation method thereof as well as a, preparation method of :2, 3, 3 - the novel near-infrared ratio fluorescence 1, 2, 3, 3 - probe; Vilsmeier 2 - 1, 2, 3, 3 - 2 - 2 - [2 - [2 -)] - 1 -]] - 1, 3, 3 - 2 - [2 - [2 -)] - 1 -]] - 1, 3, 3 . (by machine translation)
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Paragraph 0056-0064
(2020/01/25)
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- Synthesis and spectral properties of 6′-triazolyl-dihydroxanthene-hemicyanine fused near-infrared dyes
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We describe the synthesis of a range of 6′-triazolyl-dihydroxanthene-hemicyanine (DHX-hemicyanine) fused dyes through an effective copper-catalyzed azide-alkyne cycloaddition (CuAAC) "click"reaction, with the aim of providing molecular diversity and evaluating the spectral properties of these near-infrared (NIR)-active materials. This was implemented by reacting 15 different aliphatic and aromatic azides with a terminal alkynyl-based DHX-hemicyanine hybrid scaffold prepared in four steps and 35% overall yield from 4-bromosalicylaldehyde. The resulting triazole derivatives have been fully characterized and their optical properties determined both in organic solvents and under simulated physiological conditions (phosphate buffered saline containing 5% of bovine serum albumin protein). This systematic study is a first important step towards the development of NIR-I fluorogenic "click-on"dyes or related photoactive agents for light-based diagnostic and/or therapeutic applications.
- Gu, Lingyue,Renault, Kévin,Romieu, Anthony,Richard, Jean-Alexandre,Srinivasan, Rajavel
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supporting information
p. 12208 - 12215
(2020/07/30)
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- A small-sized benzothiazole-indolium fluorescent probe: The study of interaction specificity targeting c-MYC promoter G-quadruplex structures and live cell imaging
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A small-sized c-MYC promoter G-quadruplex selective fluorescent BZT-Indolium binding ligand was demonstrated for the first time as a highly target-specific and photostable probe for in vitro staining and live cell imaging and it was found to be able to inhibit the amplification of the c-MYC G-rich sequence (G-quadruplex) and down-regulate oncogene c-MYC expression in human cancer cells (HeLa). This journal is
- Zheng, Bo-Xin,She, Meng-Ting,Long, Wei,Xu, Yong-Yu,Zhang, Yi-Han,Huang, Xuan-He,Liu, Wenjie,Hou, Jin-Qiang,Wong, Wing-Leung,Lu, Yu-Jing
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supporting information
p. 15016 - 15019
(2020/12/22)
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- Synthesis of spiropyran with methacrylate at the benzopyran moiety and control of the water repellency and cell adhesion of its polymer film
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Stimuli-responsive materials have been actively researched over the past few decades. Among such materials, spiropyran is one of the most attractive compounds because the structure and polarity of the material are dramatically changed after photo irradiation, unlike other materials. In this work, we designed and synthesized a spiropyran derivative (SpMA) with a methacryloyl group on the nitrobenzene ring of a spiropyran skeleton. The UV spectra of the newly synthesized SpMA showed the photo-isomerization of spiropyran. The maximum absorption wavelength (λmax) of SpMA was 616 nm in n-hexane, a nonpolar solvent, although λmax of SpMA was 532 nm in methanol, a polar protic solvent, which resulted in an 84 nm blue-shift. SpMA was successfully polymerized by ruthenium (Ru)-catalyzed living radical polymerization. Poly(SpMA) (PSpMA) was then spin-coated on a PET substrate in order to control the surface properties of water repellency and cell adhesion. The water repellency was decreased approximately 10° under UV irradiation, because of the polarity change of PSpMA caused by photo-isomerization from the spiropyran (SP) type to the merocyanine (MC) type. In addition, NIH3T3 cells were spread only on 6% of the surface of the PSpMA thin film after UV irradiation compared with no UV irradiation. The polarity change of PSpMA by photo-isomerization is also believed to be the reason for this behavior. As a result, we successfully synthesized a photo-controllable cell culture scaffold.
- Ajiro, Hiroharu,Ando, Tsuyoshi,Murase, Nobuo
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p. 1489 - 1495
(2020/03/06)
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- Synthetic method of cyanine dye and application of cyanine dye as acid-base response fluorescent reagent
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The invention relates to a synthesis and preparation technology of cyanine dyes, in particular to design and synthesis of cyanine dyes with remarkable response to acid and alkali, which detects absorption spectra and fluorescence spectra of the cyanine dyes in PBS solutions with different pH values. Tests find that the absorption and fluorescence spectra of the compound are obviously changed underacidic and alkaline conditions, and the compound is suitable for detecting cancer cells.
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Paragraph 0019; 0022
(2020/05/14)
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- Ultrabright and Serum-Stable Squaraine Dyes
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Highly stable symmetric and asymmetric squaraine fluorophores have been synthesized featuring an internal salt bridge between a quaternary ammonium cation and the central oxycyclobutenolate ring of the chromophore. Some of our newly synthesized symmetric and asymmetric compounds display increased molar absorptivity, quantum yield in serum, and thermal/photochemical stability over previously reported squaraine-based dyes. Consequently, both classes show great promise in resurfacing the normal environment-labile squaraine dyes as novel imaging agents and scaffolds for fluorescence sensing. Furthermore, incorporating a covalent attachment point away from the conjugated system allows for biological tagging applications without disturbing the optimum optical characteristics of the newly designed fluorophore.
- Yadav, Yogesh,Owens, Eric,Nomura, Shinsuke,Fukuda, Takeshi,Baek, Yoonji,Kashiwagi, Satoshi,Choi, Hak Soo,Henary, Maged
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p. 9436 - 9445
(2020/10/19)
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- Four-condensed-ring quinoxaline derivative and preparation method therefor
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In view of the problem that the existing quinoxaline compounds are single in structure, the invention provides a full-novel structure-diversified four-condensed-ring quinoxaline derivative and a preparation method therefor. The four-condensed-ring quinoxaline derivative has a structural general formula represented by a formula (I). The four-condensed-ring quinoxaline derivative provided by the invention has cytotoxic activity to tumor cells in vitro and in vivo and can serve as an antitumor drug.
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Paragraph 0058; 0063-0065
(2020/03/05)
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- Design and Synthesis of Near-Infrared Mechanically Interlocked Molecules for Specific Targeting of Mitochondria
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The entrapment of squaraine (SQ) within a molecular container to form rotaxane has been shown to improve the dye stability and the fluorescence proficiency inside the mitochondria. The macrocycle provides shelter and protects the near-infrared (NIR) SQ chromophore from nucleophilic attacks made by the exposed thiol of Cys-containing mitochondrial proteins and mitochondrial glutathione. Herein a microwave-assisted template-directed clipping reaction on low-loading 2-chlorotrityl chloride resin is used to develop an NIR unsymmetrical squaraine rotaxane in high quantum yield.
- Chatterjee, Sudipta,Das, Rabi Sankar,Guha, Samit,Mukherjee, Ayan,Saha, Pranab Chandra,Sepay, Nayim
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- Novel near-infrared rate fluorescent probe for detecting hydrogen sulphide and preparation method and application of novel near-infrared rate fluorescent probe
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The invention discloses a novel near-infrared rate fluorescent probe for detecting hydrogen sulphide and a preparation method and application of the novel near-infrared rate fluorescent probe. The probe is a 2-[2-[2-(4-benzylazide carbobenzoxy) benzylamine-3-[(1,3-dihydrogen-1,3,3-trimethyl-2H-indole-2-idene) ethylidene]-1-cyclohexene-1-base]vinyl]-1,3,3-trimethyl-indole-onium iodide. The preparation method comprises the following steps of enabling 1,2,3,3-tetramethyl-3H-iodination indole and 2-chlorine-1-formyl-3-hydroxymethyl cyclohexene to have a dehydration and condensation reaction; enabling the obtained 2-[2-[2-chlorine-3-[(1,3-dihydrogen-1,3,3-trimethyl-2H-indole-2-idene)ethylidene]-1-cyclohexene-1-base]vinyl]-1,3,3-trimethyl indole-onium iodide and benzylamine to a reaction; and enabling the obtained 2-[2-[2-benzylamino-3-[(1,3-dihydrogen-1,3,3-trimethyl-2H-indole-2-idene) ethylidene]-1-cyclohexene-1-base]vinyl ]-1,3,3-trimethyl indole-onium iodide and chloroformic acid to havea reaction on azide base benzyl ester so as to obtain the fluorescent probe. The probe shows higher selectivity on detection of the hydrogen sulphide.
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Paragraph 0056; 0060-0064
(2019/01/23)
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- Novel near-infrared ratio fluorescent probe for detecting mercaptan, and preparation method and application thereof
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The invention discloses a novel near-infrared ratio fluorescent probe for detecting mercaptan, and a preparation method and an application thereof. The probe is 2-[2-[2-[2-[(2-acetoxyethyl)dithio]ethoxycarbonyl]benzylamino]-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-1-hexene-1,yl]vinyl]-1,3,3-trimethylindolium iodide. The preparation method comprises the following steps: carrying out a dehydration condensation reaction on 1,2,3,3-tetramethyl-3H-indolium iodide and 2-chloro-1-formyl-3-hydroxymethylcyclohexene; reacting the obtained 2-[2-[2-chloro-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-1-cyclohexene-1-yl]vinyl]-1,3,3-trimethylindolium iodide with benzylamine; and reacting the obtained 2-[2-[2-benzylamino-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-1-cyclohexene-1-yl]vinyl]-1,3,3-trimethylindolium iodide with [2-[(2-acetoxyethyl)dithio]ethoxy]carbonyl chloride to obtain the novel fluorescent probe. The probe has a high selectivity in the detection of mercaptan.
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Paragraph 0057; 0061-0065
(2019/01/21)
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- Divergent synthesis of 5′,7′-difluorinated dihydroxanthene-hemicyanine fused near-infrared fluorophores
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We describe an expedient access to a 5′,6′,7′-trifluoro dihydroxanthene-hemicyanine fused scaffold in 2 steps and 54% overall yield from the corresponding salicylic aldehyde. A 6′-regioselective nucleophilic aromatic substitution (SNAr) reactio
- Zheng, Shasha,Lingyue, Gu,Ong, Michelle Jui Hsien,Jacquemin, Denis,Romieu, Anthony,Richard, Jean-Alexandre,Srinivasan, Rajavel
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supporting information
p. 4291 - 4300
(2019/05/10)
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- Chiral Symmetry Breaking of Spiropyrans and Spirooxazines by Dynamic Enantioselective Crystallization
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Dynamic enantioselective crystallization enabled the chiral symmetry breaking of two spiropyrans and one spirooxazine. The three spiro compounds afforded racemic conglomerate crystals, and easily racemized in alcoholic solution without irradiation. Optically pure enantiomorphic crystals were obtained by vapor-diffusion crystallization or attrition-enhanced deracemization (Viedma ripening). Their absolute configurations were determined by single-crystal X-ray analysis and each enantiomorphic crystal was correlated with its solid-state circular dichroism (CD) spectrum.
- Ishikawa, Hiroki,Uemura, Naohiro,Saito, Rei,Yoshida, Yasushi,Mino, Takashi,Kasashima, Yoshio,Sakamoto, Masami
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supporting information
p. 9758 - 9763
(2019/07/04)
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- Tuning lipophilicity for optimizing the H2S sensing performance of coumarin-merocyanine derivatives
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Hydrogen sulfide (H2S) is an endogenous signaling molecule involved in various physiopathological processes; coumarin-based merocyanines have been successfully utilized for developing fluorescent H2S sensors. However, subtle changes in the chemical structure of merocyanines could induce distinct difference in the H2S sensing behavior. Investigation of the structure-property relationship of merocyanine dyes is of great importance for the development of ideal sensors with desirable performance. In this work, a series of coumarin/merocyanine (CMC) hybrid fluorescent probes with different lipophilicities have been developed. By altering the N-alkyl chain, the reaction rate with H2S and intracellular distribution of CMC sensors are optimized. The results showed that increasing the lipophilicity by attaching longer N-alkyl chains leads to a faster sensing response as well as a higher efficiency of the mitochondrial targeting ability. By virtue of rapid sensing of H2S and impressive mitochondrial co-localization ability, CM-NC6 could monitor H2S levels via a dual channel ratiometric mode. In addition, CM-NC6 is also capable of in vivo imaging of exogenous H2S. The work provided a powerful strategy for developing H2S sensors with optimized performance, which would be helpful for understanding the complicated roles of H2S in various physiological processes.
- Fang, Hongbao,Chen, Yuncong,Shi, Xiangchao,Bai, Yang,Chen, Zhongyan,Han, Zhong,Zhang, Yuming,He, Weijiang,Guo, Zijian
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supporting information
p. 14800 - 14805
(2019/09/30)
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- Water-soluble dye of indole hemicyanine structure and synthesis method of water-soluble dye
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The invention discloses a water-soluble dye of an indole hemicyanine structure and a synthesis method of the water-soluble dye. The compound structure is shown as a following formula: (please see thespecifications for the formula). According to the synthesis method, a 2,3,3-trimethylindolenine derivative and pyrrole-2-carboxaldehyde are taken as raw materials, a single condensation reaction is conducted, and the water-soluble dye of the indole hemicyanine structure is synthesized. According to the water-soluble dye of the indole hemicyanine structure, the synthesis method is simple, reactionconditions are easy to control, and the yield is high. The water-soluble dye has good water solubility and pH response and is applied to a biological body advantageously.
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Paragraph 0035-0039
(2019/11/13)
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- Iodine-Promoted Domino Oxidative Cyclization for the One-Pot Synthesis of Novel Fused Four-Ring Quinoxaline Fluorophores by sp3 C?H Functionalization
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A method for the synthesis of novel fused four-ring quinoxaline skeleton has been described by an I2 promoted sp3 C?H functionalization between 1,2,3,3-tetramethyl-3H-indolium iodides and 1,2-diamines. This transformation proceeds smoothly under metal- and peroxide-free conditions through a sequential iodination, oxidation, annulation and rearrangement. Moreover, 8,9-dichloro-5,12,12-trimethyl-2-(trifluoromethyl)-5,12-dihydroquinolino[2,3-b]quinoxaline showed good photophysical properties and was used in live cell imaging, indicating the potential value of this skeleton as a fluorophore in probes.
- Zhang, Yong,Yang, Min,Jia, Chengli,Ji, Min
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supporting information
p. 13709 - 13713
(2019/11/05)
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- A multi-signal fluorescent probe for the discrimination of cysteine/homocysteine and glutathione and application in living cells and zebrafish
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Biological thiols are ubiquitous, common in living organisms and play an important role in metabolism and redox homeostasis. Abnormal concentrations of biological thiols may lead to many malignant diseases. It is difficult to distinguish biological thiols
- Xu, Gaoping,Tang, Yonghe,Lin, Weiying
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supporting information
p. 12615 - 12620
(2018/08/01)
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- Novel near infrared ratio fluorescence probe for detecting hydrogen peroxide as well as preparation method and application of probe
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The invention discloses a novel near infrared ratio fluorescence probe for detecting hydrogen peroxide as well as a preparation method and an application of the probe. The probe is 2-[2-[2-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxycarbonyl]benzylamino]-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-1-cyclohexen-1-yl]ethenyl]-1,3,3-trimethylindolium iodide. The preparation method comprises steps as follows: 1,2,3,3-tetramethyl-3H-iodoindole and 2-chloro-1-formyl-3-hydroxymethylcyclohexene are subjected to a dehydration condensation reaction; obtained 2-[2-[2-chloro-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-1-cyclohexen-1-yl]ethenyl]-1,3,3-trimethylindolium iodide and benzylamine react; obtained 2-[2-[2-benzylamino-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylidene]-1-cyclohexen-1-yl]ethenyl]-1,3,3-trimethylindolium iodide and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbobenzoxy chloride react, and the novel fluorescence probe is obtained. The probe shows higher selectivity for detection of hydrogen peroxide.
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Paragraph 0052; 0056-0060
(2019/01/15)
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- SQUARAINE DYES AND APPLICATIONS THEREOF
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The present invention disclosed a squaraine dye of formula (I) and process for the preparation thereof. Further, the present invention disclosed to an electronic device comprising dye of formula (I).
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Page/Page column 23
(2018/02/28)
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- A near-infrared cyanine dye preparation method (by machine translation)
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The invention discloses a having excellent light stability of the near-infrared cyanine dye preparation method and use, the dye of the formula I as shown in the structural formula, R1 Hydrogen, methyl, in any one of a carboxyl group; R2 Hydrogen, methyl, alkoxy in any one of; X- Is iodine ion, bromide ion in any one of; n=1 - 5 is any integer. The dye through chemical bonding will be blocked piperidine structure unit introduced into the cycloheptane boeki indole cyanine in the mother's body, such that the resulting dye has good light stability, in the near-infrared region with absorption and emission, and has good photosensitive, photo-thermal characteristic, so that the fabric is colored, near-infrared fluorescence imaging, the photodynamic treatment, heat treating the field have good application prospect. (by machine translation)
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Paragraph 0038; 0046; 0051; 0052; 0053; 0068
(2019/01/14)
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- Environmentally sensitive material based on Benzofuroxan as well as preparation method and application thereof
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The invention provides an environmentally sensitive material based on Benzofuroxan as well as a preparation method and an application thereof. The environmentally sensitive material has a structural formula as shown in the specification, wherein R1 is sel
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Paragraph 0046; 0048; 0054; 0055
(2018/05/16)
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- Erlotinib-Guided Self-Assembled Trifunctional Click Nanotheranostics for Distinguishing Druggable Mutations and Synergistic Therapy of Nonsmall Cell Lung Cancer
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The outcome of molecular targeted therapies is restricted by the ambiguous molecular subtypes of nonsmall cell lung cancer (NSCLC), which are difficult to be defined with druggable mutations, and the inevitable emergence of drug-resistance. Here we used the Cu-catalyzed click chemistry to synthesize a chitosan-based self-assembled nanotheranostics (CE7Ns) composed of a near-infrared (NIR) fluorescent photosensitizer Cy7 and molecular targeted drug erlotinib. The well-characterized CE7Ns can release erlotinib and Cy7 fast under acidic condition in the presence of lysozyme, distinguish three molecular subtypes of NSCLC, and specifically bind to the erlotinib-sensitive epidermal growth factor receptor (EGFR)-mutated PC-9 cells. The uptake of CE7Ns is much more in PC-9 cells than in other NSCLC cells, thus generating a notable fluorescence signal in PC-9 cells. Upon NIR irradiation, Cy7 in CE7Ns produces high reactive oxygen species in PC-9 cells. The synergistic effect between erlotinib-targeted therapy and photodynamic therapy significantly up-regulates cancer suppressor p53 and inhibits Survivin, which results in more apoptosis and cell cycle arrest. Upon intravenous administration, the erlotinib-guided CE7Ns significantly accumulate in PC-9-seeded mouse lungs and produce strong fluorescence. Upon NIR irradiation, CE7Ns significantly inhibit the subcutaneously implanted PC-9 tumor growth. This study provides, for the first time, a novel strategy to synthesize a multifunctional theranostic entity to simultaneously distinguish and image druggable mutations and combine targeted therapy with photodynamic therapy to overcome drug resistance.
- Gao, Yu,Zhang, Huijuan,Zhang, Yingying,Lv, Tingting,Zhang, Lu,Li, Ziying,Xie, Xiaodong,Li, Fengqiao,Chen, Haijun,Jia, Lee
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p. 5146 - 5161
(2018/10/31)
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- Synthesis and optical properties of near-infrared meso-phenyl-substituted symmetric heptamethine cyanine dyes
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Heptamethine cyanine dyes are a class of near infrared fluorescence (NIRF) probes of great interest in bioanalytical and imaging applications due to their modifiability, allowing them to be tailored for particular applications. Generally, modifications at the meso-position of these dyes are achieved through Suzuki-Miyaura C-C coupling and SRN1 nucleophilic substitution of the chlorine atom at the meso-position of the dye. Herein, a series of 15 meso phenyl-substituted heptamethine cyanines was synthesized utilizing a modified dianil linker. Their optical properties, including molar absorptivity, fluorescence, Stokes shift, and quantum yield were measured. The HSA binding affinities of two representative compounds were measured and compared to that of a series of trimethine cyanines previously synthesized by our lab. The results indicate that the binding of these compounds to HSA is not only dependent on hydrophobicity, but may also be dependent on steric interferences in the binding site and structural dynamics of the NIRF compounds.
- Levitz, Andrew,Marmarchi, Fahad,Henary, Maged
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- Novel Spiropyran Based Composition and Application Thereof as Security Tag
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The present invention discloses the spiropyran compound of formula (I), process for preparation thereof and a composition comprising spiropyran compound of formula (I) on a support, wherein said support selected from polymers such as Poly (ethylene oxide), Polydimethylsiloxane (PDMS), Ethylene propylene diene monomer (EPDM).
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Paragraph 0061; 0062
(2018/06/30)
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- Cyanine fluorescent dye and synthesis method thereof
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The invention discloses a cyanine fluorescent dye having the structural formula represented by one of the formula I and the formula II defined in the specification. The cyanine fluorescent dye provided by the invention has both the excitation wavelength and the fluorescence emission wavelength reaching a near infrared region, and the Stokes shifts are each greater than 60 nm; the background fluorescence of the biological environment and the self-quenching and self-absorption effects of the dye in the application of living imaging are significantly reduced, the signal-to-noise ratio is improved, and the sensitivity is improved. The synthesis method of the fluorescent dye provided by the invention is simple, the raw materials are easy to obtain, and the yield is high; the fluorescent dye provided by the invention has good effect in cell imaging and living imaging of small animals, and has high light stability.
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Paragraph 0056-0059
(2018/10/11)
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- Tetraphenylethylene-based subcellular organelle viscosity probe, and preparation method and application thereof
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The invention provides a tetraphenylethylene-based subcellular organelle viscosity probe, and a preparation method and an application thereof. The subcellular organelle viscosity probe comprises a mitochondrial viscosity probe and a lysosomal viscosity probe. The preparation method mainly comprises the following steps (1) synthesis of a compound TPE-Br, (2) synthesis of a compound TPE-CHO, (3) synthesis of the mitochondrial viscosity probe, and (4) synthesis of the lysosomal viscosity probe. The synthesized viscosity probe can be used for detecting the viscosity of subcellular organelles. Thepreparation method of the tetraphenylethylene-based subcellular organelle viscosity probe is simple; the synthesized viscosity probe has good water solubility, and has no influences on the state of studied cells in the working concentration range; the viscosity probe has weak self-fluorescence background, so the imaging contrast of the subcellular organ viscosity monitoring is improved; and the viscosity probe is sensitive to the viscosity, has strong anti-interference, and has good targeting specificity to the subcellular organelles.
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Paragraph 0064; 0082-0083; 0098; 0112-0113
(2018/09/28)
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- Charge balanced fluorescence contrast agent for high signal to background ratio and Method for imaging using the same
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The present invention relates to a charge balanced fluorescence contrast agent, capable of providing a high signal to background ratio when optically observing tissues and cells using a fluorescence imaging device for image guided surgery, wherein the contrast agent emits fluorescence so that the signal to background ratio is detected to be at least 1.1 or greater, wherein the conjugate is represented by chemical formula I.COPYRIGHT KIPO 2019
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Paragraph 0033
(2019/02/26)
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- Two-photon fluorescent probe for detecting viscosity of positioning mitochondria and synthesizing method and application thereof
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The invention provides a two-photon fluorescent probe for detecting viscosity of positioning mitochondria and a synthesizing method and application thereof, and belongs to the field of small-moleculefluorescent probes. The structural formula of the two-photon viscosity probe is shown in the description; the probe can be prepared by reacting products of 3-bromine-9-ethyl carbazole and 4-formyl benzene boric acid and the products of 2, 3, 3-trimethyl-3H-benzpyrole and iodomethane. The probe has two-photon effect and is high in sensitivity relative to viscosity and is capable of detecting viscosity in a solution, cells and zebra fish body under a single-photon or a two-photon mode; and the probe has a wide application prospect in the field of biomolecule detection.
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Paragraph 0023; 0024
(2019/01/14)
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- Synthesis of stereochemically-biased spiropyrans by microwave-promoted, one-pot alkylation-condensation
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A microwave-assisted, two-step, one-pot synthesis of spiropyrans has been developed. This process was used to synthesise a range of sterically-congested spiropyrans from readily available precursors, employing environmentally benign solvents. The unusual substituent pattern possessed by these structures has been shown to influence the stereoselectivity of spiropyran ring-closure.
- Perry, Alexis,Davis, Kane,West, Lara
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p. 7245 - 7254
(2018/10/24)
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- A spiropyran-coumarin platform: An environment sensitive photoresponsive drug delivery system for efficient cancer therapy
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In spite of inventing several anticancer agents the clinical payoff still remains unsatisfactory because of their severe host toxicity due to their nonspecific biodistribution in the body. To achieve high efficiency in anti-cancer drug delivery, thus, we designed and developed a single component photoresponsive drug delivery system, a fusion of two platforms spiropyran and coumarin, which synchronizes two controlling factors: first, the lower pH of cancer tissue, which acts as an internal control and leads to the ring opening of spiropyran resulting in a distinct colour change and fluorescence activation of coumarin; and second, the release of the anti-tumor drug by the externally controlled light. Highly fluorescent nature and promising biocompatibility make the SP-Cou-Cbl system suitable for cell imaging and in vitro studies.
- Barman, Shrabani,Das, Joyjyoti,Biswas, Sandipan,Maiti,Pradeep Singh
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supporting information
p. 3940 - 3944
(2017/07/11)
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- Development of a Modular Ratiometric Fluorescent Probe for the Detection of Extracellular Superoxide
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Extracellular detection of endogeneous analytes (e.g., superoxide) can provide important insights into mechanisms of homeostasis and diseases, such as tumorigenesis. A ratiometric probe with a fluorescent reference and an analyte-specific switch-on dye was developed. Detection of ROS in the extracellular milieu was ensured by connecting the two fluorophores with a modular peptide-nucleic-acid-based linker. The ROS-sensing ability was assessed and validated in cell-free assays and in cell culture.
- Andina, Diana,Brambilla, Davide,Munzinger, Noah,Frei, Jasmine,Zivko, Cristina,Leroux, Jean-Christophe,Luciani, Paola
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supporting information
p. 4765 - 4769
(2017/04/14)
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- Synthesis, characterization and protein-association of dicyanomethylene squaraine dyes
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We prepared several new dicyanomethylene squaraine dyes derived from indolenine, benzothiazole and benzoselenazole, with different substituent groups. All the obtained dyes display intense and narrow absorption bands and bright fluorescence emission in the Vis/NIR region (665–716 nm) when dissolved in organic solvents, especially for the unsymmetrical dyes containing sulphur and selenium atoms. The use of synthesized squaraine dyes as fluorescent probes for detection of bovine serum albumin (BSA) and human serum albumin (HSA) was explored in Tris-HCl buffer solutions. We observed that all the dyes are non-emissive in buffer solution but become fluorescent in the presence of BSA or HSA proteins, with the emission intensity increasing proportionally to the protein concentration (0.00–1.22 μM). The most pronounced effect was observed for the symmetrical squaraine having two moieties of indolenine.
- Martins, Tiago D.,Pacheco, Marlene L.,Boto, Renato E.,Almeida, Paulo,Farinha, José Paulo S.,Reis, Lucinda V.
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p. 120 - 129
(2017/08/14)
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