- Synthesis of A2-D2-A1-D1 type red-emitting unsymmetrical squaraine dye: Influence of additional pyridine moiety on photophysical, electrochemical, photo and thermal stability
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We have synthesized a π-conjugated acceptor–donor–acceptor-donor (A2-D2-A1-D1) type of unsymmetrical squaraine dye, signified by USQ-1 based on 1-ethyl-2,3,3,8-tetramethyl-2,3-dihydro-1H-pyrrolo[3,2-h] quinoline moiety to improve the absorption as well as emission spectra to the red-emitting region. The influence of pyridine as a subsidiary electron acceptor unit on various properties in USQ-1 dye was compared with their close relative dye (USQ-2). The synthesized dyes were examined by FT-IR, HR-MS, 1H, and 13C NMR spectroscopy. This novel unsymmetrical squaraine dye shows a strong absorption with high molar absorptivity (?105 L mol?1 cm?1) in the range of 676–661 nm from non-polar to polar solvents. The intramolecular charge transfer (ICT) process from donor to the acceptor moiety in a non-polar to polar solvent has been investigated with the help of oscillator strengths (f), as well as transition dipole moments (μeg). These dyes showed a negative solvatochromic shift from non-polar to polar solvent. The quantitative analysis of charge transfer from the ground to the excited state of these squaraine dyes was calculated by Reichardt's ET (30) scale plot. The comparative electrochemical, as well as the thermal study of these unsymmetrical squaraines, were studied with the aid of cyclic voltammetry and thermogravimetric analysis (TGA), respectively. Additionally, A2-D2-A1-D1 type dye (USQ-1) showed an improved photo-stability compared to D2-A1-D1 type dye (USQ-2). The computational (theoretical) study of these dyes was supported with the assistance of density functional theory (DFT) together with time-dependent density functional theory (TD-DFT).
- Bhise, Rupali,Jachak, Mahesh,Khopkar, Sushil,Mehta, Viral,Shankarling, Ganapati
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- Bioorthogonal Ligation-Activated Fluorogenic FRET Dyads
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An energy transfer-based signal amplification relay concept enabling transmission of bioorthogonally activatable fluorogenicity of blue-excitable coumarins to yellow/red emitting cyanine frames is presented. Such relay mechanism resulted in improved cyani
- Albitz, Evelin,Kern, Dóra,Kormos, Attila,Bojtár, Márton,T?r?k, Gy?rgy,Biró, Adrienn,Szatmári, ágnes,Németh, Krisztina,Kele, Péter
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supporting information
(2021/12/30)
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- The Development of Highly Fluorescent Hemicyanine and Dicyanoisophorone Dyes for Applications in Dye-Sensitized Solar Cells
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Ruthenium-based metal complex dyes have been employed extensively in dye-sensitized solar cells (DSSCs) as photosensitizers, but the cost and toxicity of metal complexes have promoted the development of metal-free organic dyes. The present investigation d
- Shabir, Ghulam,Arooj, Sama,Javed, Ahad Hussain,Saeed, Aamer,Shahzad, Nadia,Iqbal, Naseem,Jabeen, Erum
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p. 799 - 815
(2022/02/05)
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- Acridinium-conjugated aromatic heterocycles as highly potent FtsZ inhibitors: Design, synthesis, and biological evaluation
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The epidemic of multidrug resistance (MDR) is a serious threat to public health, and new classes of antibiotics with novel mechanisms of action are in critical need. We rationally designed and efficiently synthesized three series of new chemical entities with potential antibacterial activity targeting filamenting temperature-sensitive mutant Z (FtsZ). Evaluation of these compounds against a panel of Gram-positive bacteria including MDR and vancomycin-resistant Enterococcus?strains indicated that most compounds showed enhanced antibacterial efficacy, comparable or even superior to the reference drugs. The newly synthesized compounds proved to be substrates of the Escherichia coli efflux pump AcrB, thus affecting the activity. Their structure–activity relationships?were summarized in detail. The most potent compound 10f quickly eliminated bacteria in a bactericidal mode, with low susceptibility to induce bacterial resistance. Further mechanistic studies with the BsFtsZ protein revealed that 10f functioned as an effective FtsZ inhibitor through altering the dynamics of FtsZ self-polymerization via a stimulatory mechanism, which leads to inhibition of cell division and cell death. Besides, 10f not only displayed no obvious cytotoxicity to mammalian cells but also had a high efficacy in a murine model of bacteremia in vivo. Regarded as a whole, our findings highlight 10f as a promising new FtsZ-targeting bactericidal agent.
- Chen, Weijin,Guo, Ting,Ma, Shutao,Ma, Yangchun,Song, Di,Zhang, Nan,Zhang, Shenyan
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- The Impact of Chiral Citronellyl-Functionalization on Indolenine and Anilino Squaraine Thin Films
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The impact on chiral aggregation in solution processed and thermally annealed thin films of two indolenine and one anilino squaraines with chiral (S)-citronellyl functionalization at the nitrogen of the squaraine backbone is investigated. A pseudo polymor
- Balzer, Frank,Beverina, Luca,Lützen, Arne,Mattiello, Sara,Meerholz, Klaus,Schiek, Manuela,Schmidtmann, Marc,Schulz, Matthias,Schumacher, Marvin F.,Serdar Sariciftci, N.,Zablocki, Jennifer
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- A Molecular-Splicing Strategy for Constructing a Near-Infrared Fluorescent Probe for UDP-Glucuronosyltransferase 1A1
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UDP-glucuronosyltransferase 1A1 (UGT1A1) is a vital metabolic enzyme responsible for the clearance of endogenous substances and drugs. Hitherto, the development of fluorescent probes for UGTs was severely restricted due to the poor isoform selectivity and
- Cui, Jingnan,Feng, Lei,Gao, Jian,James, Tony D.,Liu, Tao,Ma, Xiaochi,Ma, Yinhua,Tian, Xiangge
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supporting information
p. 24566 - 24572
(2021/10/12)
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- Pyroptosis drug prodrug, preparation method thereof and pyroptosis drug
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The invention discloses a pyroptosis drug prodrug, a preparation method thereof and a pyroptosis drug. The pyroptosis drug prodrug provided by the invention can cause mitochondria damage, release cytochrome c and activate Caspase3 to shear GSDME by targeting mitochondria, so that pyroptosis of cells occurs. The prodrug (NCyNH2) has selectivity to tumor cells, damage to normal cells is reduced, and the activation condition of the prodrug (NCyNH2) can be detected through recovery of self-fluorescence. After intratumor administration, the prodrug can effectively regulate the tumor immune microenvironment and activate T cell mediated anti-tumor immune response. The molecule has huge application prospects in the aspects of mitochondrial targeting, cell respiration inhibition, pyroptosis induction, tumor immune microenvironment improvement, T cell mediated anti-tumor immune response activation and the like.
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Paragraph 0088; 0091-0092
(2021/06/13)
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- The effect of bis-carboxylic groups of squarylium dyes on the efficiency of dye-sensitized solar cells
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Symmetric squarylium dye (SQIND1) with bi-carboxylic groups has been synthesized and photoelectrochemical properties have been studied in comparison with its non-functionalized analog groups (SQIND2). The experimental results showed that the introduction of anchor carboxylic groups in SQIND1 sensitizer provides a more intimate contact with nanoparticles TiO2 which increases the number of charge carriers transferred from the SQIND1 to the semiconductor. The theoretical calculations and absorbance results show that the electron density of LUMO of SQIND1 is delocalized in the whole chromophore, leading to strong electronic coupling between SQIND1 sensitizer and conducting band of TiO2, resulting in improved dye-sensitized solar cell efficiency compared to SQIND2. Hence, the SQIND1 sensitized exhibit better photovoltaic performance. Although, the absence of any linker groups in the SQIND1, then SQIND1 was perfect efficiently sensitized on porous TiO2 with the long UV–Vis and NIR region up to 800?nm of the spectrum and showed higher remarkable performance of values, such as η of 3.3%, a Jsc of 7.6?mA/cm2, a Voc of 0.59, and FF of 0.73.
- Al-horaibi, Sultan A.,Garoon, Eman M.,Bhise, Narendra A.,Gaikwad, Suresh T.,Rajbhoj, Anjali S.
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p. 1769 - 1778
(2019/12/27)
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- The design of a novel near-infrared fluorescent HDAC inhibitor and image of tumor cells
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Histone deacetylases (HDACs) have been found to be biomarkers of cancers and the corresponding inhibitors have attracted much attention these years. Herein we reported a near-infrared fluorescent HDAC inhibitor based on vorinostat (SAHA) and a NIR fluorop
- Bao, Bin,Huang, Ying,Li, Jia,Lu, Wei,Ru, Hong-bo,Yu, Jia-hui,Zang, Yi
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supporting information
(2020/07/15)
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- Photodynamic activity of indolenine-based aminosquaraine cyanine dyes: Synthesis and in vitro photobiological evaluation
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The synthesis and characterization of several indolenine-based symmetrical squaraine dyes is herein reported. These compounds, possessing different amine groups bound to the squaric ring, display strong absorption within the so-called “phototherapeutic window”, have high singlet oxygen generation ability and high stability in the presence of radiation. Moreover, their potential as photosensitizers was evaluated in vitro by a photodynamic activity test in several tumor (Caco-2, MCF-7 and PC-3) and non-tumor (NHDF and N27) cell lines. Light-emitting diode systems emitting radiation at wavelengths close to those of maximum dye absorption were constructed and used in the in vitro assays. Of these, the dye with the unsubstituted four-membered central ring exhibited the most relevant photodynamic properties, with an interesting selectivity for PC-3 cells when compared to the normal human cell line (NHDF) being observed. Aminosquaraine dyes bearing amino and ethanolamino groups, despite showing marked cytotoxicity compared to the zwitterionic dye, produced some phototherapeutic effect. Flow cytometry, using propidium iodide as a viability staining, demonstrated that this zwitterionic dye induces death within the range of 4–24 h after exposure to light. Our study also showed that this dye does not accumulate preferentially in cell's mitochondria. Although in different extents, the squaraine dyes involved in this work presented promising in vitro results as photosensitizers.
- Lima, Eurico,Ferreira, Octávio,Silva, Joana F.,Santos, Adriana O.,Boto, Renato E.,Fernandes, José R.,Almeida, Paulo,Silvestre, Samuel M.,Reis, Lucinda V.
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- Near-infrared fluorescent probe for bimodal detection of sulfur dioxide, and preparation method and application thereof
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The invention discloses a near-infrared fluorescent probe for bimodal detection of sulfur dioxide, and a preparation method and application thereof. The near-infrared fluorescent probe for bimodal detection of sulfur dioxide is a hemicyanine dye derivativ
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Paragraph 0037-0039
(2020/05/02)
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- N-alkylated linear heptamethine polyenes as potent non-azole leads against Candida albicans fungal infections
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In this study, eighteen heptamethine dyes were synthesised and their antifungal activities were evaluated against three clinically relevant yeast species. The eighteen dyes were placed within classes based on their core subunit i.e. 2,3,3-trimethylindolenine (5a-f), 1,1,2-trimethyl-1H-benzo[e]indole (6a-f), or 2-methylbenzothiazole (7a-f). The results presented herein imply that the three families of cyanine dyes, in particular compounds 5a-f, show high potential as selective scaffolds to treat C. albicans infections. This opens up the opportunity for further optimisation and investigation of this class compounds for potential antifungal treatment.
- Critchley, Megan E.,Lawrence, Clare L.,McKenna, Sean T.,Okoh, Adeyi Okoh,Smith, Robert B.,Vishwapathi, Vinod
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supporting information
(2020/07/21)
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- NIR-II Chemiluminescence Molecular Sensor for In Vivo High-Contrast Inflammation Imaging
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Chemiluminescence (CL) sensing without external excitation by light and autofluorescence interference has been applied to high-contrast in vitro immunoassays and in vivo inflammation and tumor microenvironment detection. However, conventional CL sensing u
- Fan, Yong,Lu, Lingfei,Wang, Shangfeng,Yang, Yanling,Yu, Peng,Zhang, Fan,Zhang, Qisong
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supporting information
p. 18380 - 18385
(2020/08/17)
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- Dimer prodrug and preparation method and application thereof
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The present invention discloses a dimer prodrug and a preparation method and an application thereof. A structural formula of the dimer prodrug is shown as follows. The dimer prodrug has a dual fluorescence effect, quenches fluorescences of CyNH2 and DOX through ICT and FRET effects, well monitors an activation process of a drug, also reduces toxicity, also utilizes a synergistic effect of the CyNH2 and DOX, and can also enhance a treatment effect on tumors.
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Paragraph 0059-0060
(2020/12/30)
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- A carbazole-hemicyanine dye based ratiometric fluorescent probe for selective detection of bisulfite (HSO3 ?) in cells and C. elegans
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Bisulfite (HSO3 ?) is an important sulfur dioxide (SO2) derivative, which plays a major role in many physiological processes and is also closely associated with a variety of diseases. Thus the development of highly selective and sensitive fluorescent probes is essential to detect HSO3ˉ in living cells. In this work, we report the synthesis and analysis of a ratiometric fluorescent probe for selective detection of HSO3ˉ based on the 1,4-nucleophilic addition reaction with the carbazole as an electron donor (D) and aldehyde group as an electron acceptor (A). The addition of HSO3ˉ and other ions to our probe can be observed by UV - vis and fluorescence spectrometry. Our investigation proved that the probe is highly selective and sensitive for HSO3ˉ and ratiometric changes. Moreover, the probe has good cell permeability and was successfully applied to the detection of exogenous HSO3ˉ in Hela cells and C. elegans.
- Bi, Keying,Tan, Rui,Hao, Ruiting,Miao, Lanxi,He, Yanqi,Xianghua, Wu,Zhang, Junfeng,Rui, Xu
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p. 545 - 548
(2018/12/11)
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- Siliceous nanoparticle drug carrier, diagnostic and therapeutic preparation thereof and preparation method
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The invention discloses a siliceous nanoparticle drug carrier, a diagnostic therapeutic preparation thereof and a preparation method. The carrier is a vesicle having a lipid bilayer structure formed by doping hydration and self-assembly of a fluorescent amphiphilic molecule and a silicon-containing composite liposome, wherein the fluorescent amphiphilic molecule is a compound taking a glycerol skeleton structure as a core and formed by a bonded hydrophobic long chain and a fluorescent group; the silicon-containing composite liposome is composed of a silicon-containing inorganic precursor, a hydrophobic lipid chain, and a linking group coupling the silicon-containing inorganic precursor and the hydrophobic lipid chain, and the silicon-containing inorganic precursor of the silicon-containingcomposite liposome is hydrolyzed and then hydrolysis products are condensed to form an inorganic silicate network structure distributed on the surface of the vesicle. The diagnostic and therapeutic preparation prepared by using the carrier to load a drug has high stability, combines two drug controlled release mechanisms, that is pH and photothermal response, and enhances the stability of the fluorescent group. Through combination of chemotherapy and photothermal therapy, the recurrence rate of tumors is effectively reduced.
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- IR780 ketone form cyanine dye molecule, and preparation method and crystal structure thereof
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The invention relates to the field of fluorescent dyes, and discloses an IR780 ketone form cyanine dye molecule, and a preparation method and crystal structure thereof. The cyanine dye is simple in synthetic method, less in by-product, high in yield and stable in structure; and an emission spectrum can be in a near infrared region under an acidic condition, and the crystal structure obtained by adopting dichloromethane and diethyl ether diffusion methods through cultivation is stable. Based on the above advantages, the cyanine dye molecule can have good application prospects in the field of fluorescent dyes and bioluminescent imaging studies.
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- Near-infrared fluorescent molecule for controlled release of singlet oxygen and preparation method thereof
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The invention discloses a near-infrared fluorescent molecule for controlled release of singlet oxygen and a preparation method thereof. specifically, cyanine is used as a main structure to synthesizea compound B2, and then the compound B2 reacts with malononitrile to form a C=N double bonds to obtain a target product C2. The target compound C2 can release singlet oxygen under the irradiation of near-infrared light. Through laser irradiation with the wavelength of 635 nm, the absorbancy value reduction rate of C2 molecules at the maximum absorption wavelength is higher than that of rose bengalmolecules; the absorbancy value reduction rate of C2 molecules at 410 nm is faster than that of rose bengal molecules, i.e., the singlet oxygen generation rate is faster than that of rose bengal molecules, wherein the singlet oxygen yield of C2 molecules is 0.56.
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- Near-infrared fluorescent probe for selective detection of Cu2+ in living cells and in Vivo
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A NIR-rhodamine fluorescent probe was designed and successfully synthesized. The structure of the probe NRh-Cu was characterized by 1H NMR, 13C NMR and HRMS. The probe was found to show high sensitivity and high selectivity. The dete
- Xu, Zhiyang,Wang, Hong,Chen, Zhen,Jiang, Hongli,Ge, Yanqing
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supporting information
p. 404 - 410
(2019/03/26)
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- Detection of hypochlorous acid fluctuation via a selective near-infrared fluorescent probe in living cells and in vivo under hypoxic stress
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Hypoxic stress is a common concern in medicine and biology, which can induce the cellular injury and death by excess production of reactive oxygen species (ROS). Hypochlorous acid (HOCl), one of the ROS, plays a crucial role in the oxidative damage to tissue proteins in the pathogenesis of various diseases. Therefore, excess production of HOCl might be an important factor for the damage caused by hypoxic stress. However, most of the present methods cannot meet the demand of real-time detection on account of the labile and reactive chemical properties of HOCl. Herein, we designed a near-infrared fluorescent probe, Cy-HOCl, for the selective imaging of HOCl in cells and in vivo. Cy-HOCl includes two moieties: a 4-amino-3-nitrophenol group as the response unit and a near-infrared heptamethine cyanine fluorophore as the fluorescent modulator. Cy-HOCl exhibits excellent selectivity and sensitivity towards the detection of HOCl. The hypoxic response behavior of Cy-HOCl is evaluated in cells to clarify the relationship between HOCl and hypoxia. The probe is also applied to measure HOCl in ex vivo-dissected organs of an acute ischemia mouse model as well as for real-time monitoring the changes of HOCl in the hypoxic zebrafish model.
- Huang, Yan,He, Na,Wang, Yude,Zhang, Liangwei,Kang, Qi,Wang, Yunqing,Shen, Dazhong,Choo, Jaebum,Chen, Lingxin
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p. 2557 - 2564
(2019/04/17)
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- A hemicyanine derivative for near-infrared imaging of β-amyloid plaques in Alzheimer's disease
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The formation of amyloid-β (Aβ) plaques in the brain is one of the main pathological features of Alzheimer's disease (AD). The imaging probes, capable of detecting Aβ deposition, are important tools for early diagnosis of AD. In this article, we designed, synthesized and evaluated a cyanine-based near-infrared fluorescence (NIRF) probe ZT-1 for the detection of Aβ deposits in the brain. The probe had excellent fluorescent properties with an emission maximum above 720 nm upon binding to Aβ aggregates with affinity of 445.0 nM (Kd). Furthermore, ZT-1 exhibited good biostability, photostability, and binding selectivity toward Aβ1-42 aggregates by in vitro fluorescence staining experiments. In vivo NIRF imaging result also revealed that our probe could efficiently differentiate transgenic and wild-type mice. All these studies indicated that ZT-1 is a promising fluorescent probe for Aβ plaques in the AD brains.
- Yang, Hua-Li,Fang, Si-Qiang,Tang, Yan-Wei,Wang,Luo, Heng,Qu, Lai-Liang,Zhao, Jin-Hua,Shi, Cun-Jian,Yin, Fu-Cheng,Wang, Xiao-Bing,Kong, Ling-Yi
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supporting information
p. 736 - 743
(2019/07/09)
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- Bifunctional fluorescent probe for detecting viscosity and sulfur dioxide
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The invention discloses a bifunctional fluorescent probe for detecting viscosity and sulfur dioxide. The red fluorescence of the fluorescent probe is gradually enhanced along with the increase of viscosity, and the blue fluorescence of the fluorescent probe is enhanced along with the increase of SO2, so that different fluorescence response signals are displayed, and the distinguishing detection isrealized. The fluorescent probe provided by the invention has important application value in the field of biochemistry.
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Paragraph 0017; 0021
(2019/11/21)
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- Application of organic molecule in preparation of tumor targeting, diagnosis and therapeutic reagents
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The invention provides an application of an organic molecule in preparation of tumor targeting, diagnosis and therapeutic reagents. In the organic molecule provided by the invention, the organic molecule has good tumor cell mitochondrial targeting property through functional groups of methine cyanine/methine cyanine derivatives; porphyrin/porphyrin derivatives can produce a large amount of reactive oxygen, and have the effect of photodynamic therapy; meanwhile, disulfide bonds can respond to a reductive microenvironment in the tumor cells, are specifically recognized by high-expression glutathione and are broken; after breaking, the intramolecular FRET effect disappears, a fluorescence signal changes greatly, and thus the fluorescence imaging diagnosis of tumors can be performed and the reaction process can be monitored in real time. Furthermore, in the organic molecule, the functional groups of the methine cyanine/methine cyanine derivatives and porphyrin/porphyrin derivative groups have synergistic effects, the synergistically amplified photodynamic effect can be produced, and thus photodynamic therapy on tumors is realized.
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Paragraph 0164-0166; 0173; 0180
(2019/07/16)
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- Lysosome-specific sensing and imaging of pH variations in vitro and in vivo utilizing a near-infrared boron complex
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As a focus issue, the study of lysosomal pH has attracted much attention as it is closely associated with the state of lysosome, which plays a vital role in endocytosis and autophagy. In order to investigate the lysosomal pH, fluorescence bioimaging is one of the most widely-explored approaches. Unfortunately, the probes are insufficient to absorb or emit in the near-infrared (NIR) region, which could minimize photodamage to organisms and maximize tissue penetration in living systems. As a novel family of NIR dyes, hemicyanine has been selected for NIR bioimaging and biosensing owing to its excellent optical properties, easy preparation and good biocompatibility. Employing a classic rhodamine-hemicyanine hybrid, we first designed and synthesized a NIR boron complex (HCy-BIZ-BF2) with lysosome-targeting and pH-sensing properties. It is worth mentioning that after HCy-BIZ was coordinated with boron fluoride, HCy-BIZ-BF2 exhibited an improved photostability as well as an enlarged Stokes shift, and was subsequently applied to monitor the lysosomal pH in cells stimulated with chloroquine. Further investigation of pH changes in mice illustrated that HCy-BIZ-BF2 performed well in detecting the pH in living organisms. Therefore, this concept of boron complex derived from hemicyanine is not only applicable in pH detection, but also conducive for preparing promising novel NIR bioprobes and obtaining precise measurements of physiological parameters in specific physiological processes.
- Shi, Yuxiang,Meng, Xiangchun,Yang, Huiran,Song, Linna,Liu, Shujuan,Xu, Aqiang,Chen, Zejing,Huang, Wei,Zhao, Qiang
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supporting information
p. 3569 - 3575
(2019/06/13)
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- Observation of Acetylcholinesterase in Stress-Induced Depression Phenotypes by Two-Photon Fluorescence Imaging in the Mouse Brain
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Oxidative stress in depression is a prime cause of neurotransmitter metabolism dysfunction in the brain. Acetylcholinesterase (AChE), a key hydrolase in the cholinergic system, directly determines the degradation of neurotransmitters. However, due to the complexity of the brain and lack of appropriate in situ imaging tools, the mechanism underlying the changes in AChE activity in depression remains unclear. Hence, we generated a two-photon fluorescence probe (MCYN) for real-time visualization of AChE with excellent sensitivity and selectivity. AChE can specifically recognize and cleave the carbamic acid ester bond in MCYN, and MCYN emits bright fluorescence at 560 nm by two-photon excitation at 800 nm. By utilizing MCYN to monitor AChE, we discovered a significant increase in AChE activity in the brains of mice with depression phenotypes. Notably, with the assistance of a two-photon fluorescence imaging probe of the superoxide anion radical (O2?-), in vivo visualization for the first time revealed the positive correlation between AChE and O2?- levels associated with depressive behaviors. This finding suggests that oxidative stress may induce AChE overactivation, leading to depression-related behaviors. This work provides a new and rewarding perspective to elucidate the role of oxidative stress regulating AChE in the pathology of depression.
- Wang, Xin,Li, Ping,Ding, Qi,Wu, Chuanchen,Zhang, Wen,Tang, Bo
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p. 2061 - 2068
(2019/02/05)
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- Fluorescent dye, preparation method and applications thereof
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The invention belongs to the technical field of organic synthesis, and particularly relates to a fluorescent dye, a preparation method and applications thereof, wherein the fluorescent dye has a structural general formula represented by a formula I defined in the specification, X and Y are the same or different O, S, C(CH3)2 or NR6, R2 and R3 are the same or different hydrogen or functional groups, R1, R4, R5 and R6 are all functional groups, and Z is a negative ion. According to the present invention, the fluorescent dye has living cell membrane permeability, can be used for fluorescence imaging of living cell microstructures, and can obtain STED super-resolution fluorescence imaging, laser confocal imaging and other fluorescence imaging of living cells.
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Page/Page column 9; 10; 29; 30; 35; 36; 41; 42
(2019/10/01)
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- Fluorescent probe for detecting fluoride ions
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The invention discloses a fluorescent probe for detecting fluoride ions in an organism, and belongs to the technical field of analytical chemistry. The fluorescent probe uses a cyanine dye QCy7 as a parent body, a silicon-oxygen bond as a switch and hydroxybenzyl as a linker, and the chemical structure general formula of the fluorescent probe is as shown in a formula (I). The fluorescent probe hassimple synthesis and is convenient to use, can specifically react with the fluoride ions, breaks the silicon-oxygen bond, and releases fluorescence of fluorogen QCy7 through electron transfer. The fluorescent probe is not interfered with other ions in the process of detecting the fluoride ions, has good selectivity to the fluoride ions, and can accurately detect the fluoride ions in the organism.
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Paragraph 0014; 0027
(2019/11/12)
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- An Optical/Photoacoustic Dual-Modality Probe: Ratiometric in/ex Vivo Imaging for Stimulated H2S Upregulation in Mice
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Tracking signaling H2S in live mice demands responsive imaging with fine tissue imaging depth and low interferences from tissue scattering/autofluorescence and probe concentration. With complementary advantages of fluorescence and photoacoustic (PA) imaging, optical/PA dual-modality imaging was suggested for in/ex vivo H2S imaging. Therefore, a meso-benzoyloxyltricarboheptamethine cyanine, HS-CyBz, was prepared as the first ratiometric optical/PA dual-modality probe for H2S, profiting from a keto-enol transition sensing mechanism. Tail intravenous injection of this probe leads to probe accumulation in the liver of mice, and the endogenous H2S upregulation triggered by S-adenosyl-l-methionine has been verified by ratiometric optical/PA imaging, suggesting the promising potential of this ratiometric dual-modality imaging.
- Chen, Zhongyan,Mu, Xueling,Han, Zhong,Yang, Shiping,Zhang, Changli,Guo, Zijian,Bai, Yang,He, Weijiang
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supporting information
p. 17973 - 17977
(2019/11/28)
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- Compound with fluorescence resonance energy transfer performance and its application
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The invention relates to a compound with fluorescence resonance energy transfer performance and its application. The compound is prepared by trimethine cyanine dye and pentamethine cyanine dye througha proper connecting arm. The compound provided by the invention can be applied to detect active oxygen and active nitrogen, and is not influenced by probe concentration, background fluorescence, instrumental error and other factors; moreover, the compound has relatively high FRET efficiency.
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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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- A ratiometric fluorescent probe for peroxynitrite prepared by: De novo synthesis and its application in assessing the mitochondrial oxidative stress status in cells and in vivo
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A ratiometric fluorescent probe Cy-NEt2 for detecting ONOO- is designed and prepared by de novo synthesis, which is a reliable, cheap and flexible route. The probe is applied for monitoring the level of mitochondrial ONOO-
- Zhou, Dong-Ye,Li, Yongfei,Jiang, Wen-Li,Tian, Yang,Fei, Junjie,Li, Chun-Yan
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supporting information
p. 11590 - 11593
(2018/11/27)
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- A ruthenium(ii) complex-cyanine energy transfer scaffold based luminescence probe for ratiometric detection and imaging of mitochondrial peroxynitrite
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A novel ruthenium(ii) complex-cyanine energy transfer scaffold has been established for the development of a ratiometric luminescence probe for ONOO- detection. The probe, Ru-Cy5, is localized in mitochondria of live cells, allowing ratiometric sensing and imaging of ONOO- therein.
- Zhang, Wenzhu,Liu, Yi,Gao, Quankun,Liu, Chaolong,Song, Bo,Zhang, Run,Yuan, Jingli
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supporting information
p. 13698 - 13701
(2019/01/03)
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- Two-photon fluorescent probe capable of recognizing mitochondrion pH and application
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The invention discloses a two-photon fluorescent probe capable of recognizing the mitochondrion pH, and further discloses application of the fluorescent probe in mitochondrion pH detection. Experiments prove that the two-photon fluorescent probe detects t
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Paragraph 0017
(2017/03/08)
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- A highly selective, colorimetric, and environment-sensitive optical potassium ion sensor
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Potassium ions (K+) play vital roles in many biological processes and thus highly selective sensors for K+ are critical for disease diagnosis and health monitoring. Herein, we report a colorimetric K+ sensor (KS7) in which a hemicyanine dye was used as a fluorophore and phenylaza-[18]crown-6 lariat ether (ACLE) was utilized as a K+ ligand. The maximum absorption peak of KS7 shifted hypsochromically by 77 nm (from 515 to 438 nm) with an isosbestic point at 452 nm upon the addition of K+ to its aqueous solution accompanied by a color change from red to yellow. This sensor exhibited a linear response range to K+ from 1 to 200 mM, indicating its wide detection range for cellular, urinary, and environmental potassium ions. Further, this sensor is solvent-sensitive, implying its environmental sensitivity. For the demonstration of its applications, we prepared filter paper-based K+ test strips, which were used to detect K+ in urine conveniently.
- Song, Guangjie,Sun, Ruofan,Du, Jiqing,Chen, Meiwan,Tian, Yanqing
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supporting information
p. 5602 - 5605
(2017/07/10)
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- A turn-on spiropyran derivative based reversible photo-driven colorimetric and fluorescent chemosensor for trivalent metal ions
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A reversible colorimetric and fluorescent chenosensor for trivalent metal ions (M3+), 1′-ethyl-3′,3′-dimethyl-6-nitrospiro [chromene-2,2′-indoline] spiropyran (SP) has been synthesized. The sensing ability of SP towards M3+ (Fe3+, Al3+ and Cr3+) was investigated by SEM, 1H NMR and HRMS. And the performances of SP are investigated by using of UV–vis absorption and fluorescence spectra. The SP is proved to be a colorimetric and fluorescent chemosensor, which is selective, sensitive, good linear-relationship, low detection limit, good repeatability to M3+. Moreover, the SP also could be employed as colorimetric test strips to detect M3+ and a reusable three-state molecular logic function.
- Meng, Juxiang,Xu, Henan,Li, Zhongyu,Xu, Song,Yao, Chao
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p. 6637 - 6643
(2017/10/23)
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- Hemicyanine-structured near infrared dye as well as preparation method and application of hemicyanine-structured near infrared dye
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The invention provides a hemicyanine-structured near infrared dye as well as a preparation method and application of the hemicyanine-structured near infrared dye. The structural formula of the dye is represented by formula I (shown in the description), wherein R1 represents C1-C32 linear, branched or cyclic alkyl, and R2 represents one of hydrogen, bromine, methoxyl, N,N-dimethylamino, ethyoxyl, hydroxyl, carboxyl methoxy or acetyl methoxy. The dye is prepared through the reaction of a Cy7 cyanine dye and resorcinol with benzimidazole. By introducing a benzimidazole group, the prepared dye is capable of absorbing and emitting in a near infrared region and responds to the pH value of the environment.
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Paragraph 0026; 0027; 0028
(2017/08/26)
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- A selective coumarin-based “turn-on” fluorescent sensor for the detection of cysteine and its applications for bioimaging
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A coumarin-based compound (1) was designed and synthesized as a new turn-on fluorescent probe for the detection of cysteine. The probe exhibited higher selectivity towards the target molecule over other thiol and amino acids at pH 7.2 in aqueous media CH3CN-HEPES (0.02 mol/L, pH 7.2, 1:9, v/v). The reaction mechanism is attributed to the cysteine-induced SNAr substitution-rearrangement reaction. Remarkable enhancement of up to 20-fold in fluorescence intensity was achieved in the detection of cysteine. When applied for the fluorescence imaging of cysteine, the compound 1 emitted a green fluorescence in Hi5 cell cytoplasm. The in vivo imaging of Caenorhabditis elegans had further confirmed the cysteine detection by compound 1.
- Yang, Yan,Wang, Huan,Wei, Yu-Lin,Zhou, Jie,Zhang, Jun-Feng,Zhou, Ying
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supporting information
p. 2023 - 2026
(2017/10/30)
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- Indolinyl spiropyran colorimetric probe, preparation method and application
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The invention relates to an indolinyl spiropyran colorimetric probe. The colorimetric probe is 1'-ethyl-3',3'-dimethyl-6-nitrospiro[benzopyran-2,2'-indoline]. A preparation method for the indolinyl spiropyran colorimetric probe comprises the steps of preparing a 1-ethyl-2,3,3-trimethyl-3H-indolyl iodine salt, preparing 1'-ethyl-3',3'-dimethyl-6-nitrospiro[benzopyran-2,2'-indoline] and carrying out separation and purification. According to an application of the indolinyl spiropyran colorimetric probe, the colorimetric probe is used for detecting Fe in solutions. The indolinyl spiropyran colorimetric probe, the preparation method and the application have the beneficial effects that the synthetic process of the indolinyl spiropyran colorimetric probe is relatively simple, the reaction conditions are easily controlled, and the pure product can be obtained through simple aftertreatment, so that the indolinyl spiropyran colorimetric probe has excellent chemical stability; the probe is solid powder and is convenient to store, thereby having a good prospect; and the probe is stable in property under the condition of ethanol solution, and the physical and chemical properties of the probe do not change fundamentally after the probe is stored for 2 months.
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Paragraph 0010; 0024; 0025
(2017/07/05)
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- Unraveling the Hydrolysis of Merocyanine-Based Probes in Biological Assay
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Merocyanine dyes, owing to their unique photochemical properties, are widely used to fabricate probes for the detection of biologically active small molecules and bioimaging. In this paper, merocyanine-based probes were proved of undergoing unwanted hydrolysis. To explore the strategies toward avoiding the hydrolysis, the detailed hydrolysis mechanism was first investigated, which was also confirmed by density functional theory (DFT) calculation. Then a series of merocyanine dyes were rationally designed. Influences of molecular structures of the probes, the analytical media such as pH and components of the solution on the hydrolysis were systematically studied. The experimental results suggest that merocyanine based probes with low electron density are more likely to suffer the hydrolysis, which could be exacerbated by the well-accepted strategy for constructing type-II probes. It is worth noting that chemical surroundings could also exert distinctive influence on the hydrolysis. The hydrolysis could be obviously aggravated when fetal calf serum or DMSO was deployed. Our findings will definitely provide an effective and reliable approach for guiding the rational design of highly robust merocyanine-based probes and the optimization of the analytical media, which is helpful in terms of avoiding the hydrolysis of the probes and hydrolysis caused analytical errors.
- Wang, Liqiang,Hao, Yuanqiang,Huang, Jianhan,He, Yonghui,Zeng, Ke,Li, Juan,Chabu, Johnny Muya,Chen, Wansong,Yang, Minghui,Deng, Liu,Liu, You-Nian
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p. 9136 - 9142
(2016/09/28)
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- FRET-Based Mito-Specific Fluorescent Probe for Ratiometric Detection and Imaging of Endogenous Peroxynitrite: Dyad of Cy3 and Cy5
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Peroxynitrite (OONO-) is profoundly implicated in health and disease. The physiological and pathological outcome of OONO- is related to its local concentration, and hence, a reliable OONO- assay is highly desired. We have developed a FRET-based small-molecule fluorescent probe (PNCy3Cy5), harnessing the differential reactivity of Cy3 and Cy5 toward OONO- by fine-tuning. It exhibits high detection sensitivity and yields a ratiometric fluorescent signal. We have exemplified that it can be applied in semiquantitative determination of OONO- in living cells. Notably, it specifically localizes in mitochondria, where endogenous OONO- is predominantly generated. Thus, PNCy3Cy5 is a promising molecular tool for peroxynitrite biology.
- Jia, Xiaotong,Chen, Qiangqiang,Yang, Yingfang,Tang, Yao,Wang, Rui,Xu, Yufang,Zhu, Weiping,Qian, Xuhong
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p. 10778 - 10781
(2016/09/09)
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- Quantification of cysteine hydropersulfide with a ratiometric near-infrared fluorescent probe based on selenium-sulfur exchange reaction
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Cysteine hydropersulfide (Cys-SSH) plays primary roles in the synthesis of sulfur-containing cofactors, regulation of cellular signaling, activation or inactivation of enzyme activities, and modulation of cellular redox milieu. However, its biofunctions need to be further addressed due to the fact that many issues remain to be clarified. Herein, we conceive a novel ratiometric near-infrared fluorescent probe Cy-Dise for the sensitive and selective detection of Cys-SSH in living cells and in vivo for the first time. Cy-Dise is composed of three moieties: bis(2-hydroxyethyl) diselenide, heptamethine cyanine, and d-galactose. Cy-Dise exhibits a satisfactory linear ratio response to Cys-SSH via a selenium-sulfur exchange reaction in the range of 0-12 μM Cys-SSH. The experimental detection limit is determined to be 0.12 μM. The results of ratio imaging analyses confirm the qualitative and quantitative detection capabilities of Cy-Dise in HepG2 cells, HL-7702 cells, and primary hepatocytes. The level changes of Cys-SSH in cells stimulated by some related reagents are also observed. The probe is also suitable for deep tissue ratio imaging. Organ targeting tests with Cy-Dise in normal Spraque-Dawley (SD) rats and Walker-256 tumor SD rats verify its predominant localization in the liver. The probe is promising for revealing the roles of Cys-SSH in physiological and pathological processes.
- Han, Xiaoyue,Yu, Fabiao,Song, Xinyu,Chen, Lingxin
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p. 5098 - 5107
(2016/07/29)
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- Polymethine dye precursor, the precursor of the skeleton contg. squarilium dye, a dye-sensitized solar cell using the same, and a photoelectric conversion element
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PROBLEM TO BE SOLVED: To provide: a dye that can improve photoelectric conversion efficiency in a visible region and a near infrared region, that is difficult to be deactivated, and that is appropriate for a near infrared region; and a dye-sensitized solar cell and a photoelectric conversion element using the same.SOLUTION: A squarylium dye is represented by formula (5) typically, and a dye-sensitized solar cell or a photoelectric conversion element uses the squarylium dye. In the formula, Rand Rdenote each a hydrogen atom, an alkyl group or the like, Ydenotes a hydrogen atom, -CH=C(CN)COOR, -COOR, -POR or the like, and Xand Xdenote each C(CH), O, N, S or the like.
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Paragraph 0077; 0079
(2019/12/05)
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- Survey, fluorescence spectra, and solubility of liquid cyanine dyes
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We synthesized four liquid cyanine dyes, namely N,N′-didodecyl 44,N,N′-dioctadecyl indolenium 45,N,N′-bis(2,5,8-trioxa-10-octadecanyl)benzoxazolium 50 and benzothiazolium 51, which have a bis(perfluorobutylsulfonyl)imide anion. In the neat form, these liquid dyes exhibit more intense fluorescence at ?196 °C than at 25 °C. The liquid N,N′-dialkylated indolenium derivatives 44 and 45 exhibited larger solubility in hexane than the corresponding solid derivatives. In addition, the liquid N,N′-bis(2,5,8-trioxa-10-octadecanyl)benzoxazolium and benzothiazolium derivatives 50 and 51 were more soluble in propanol than the corresponding solid derivatives.
- Matsui, Masaki,Yamamoto, Takaya,Kubota, Yasuhiro,Funabiki, Kazumasa
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p. 10187 - 10196
(2016/12/07)
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- A microwave-assisted and environmentally benign approach to the synthesis of near-infrared fluorescent pentamethine cyanine dyes
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A time-efficient and eco-conscious microwave methodology was developed and applied to synthesize a systematic library of pentamethine cyanine dyes and their corresponding precursors. The synthesis outlined herein drastically reduced the reaction pathway for pentamethine carbocyanine dye syntheses from days to min, as well as producing increased yields (89-98%) to the conventional heating method (18-64%). Twelve examples of pentamethine cyanine dyes were synthesized by means of microwave-assisted organic synthesis which provided excellent yield in expedited reaction time and were obtained using facile isolation methods. Furthermore, three cyanines were prepared with a novel methylene dioxy heterocyclic structure which imparted an approximately 40 nm bathochromic shift compared to unsubstituted counterparts; these results were shown to be in agreement with DFT calculations and HOMO-LUMO energy differences.
- Owens, Eric A.,Bruschi, Nicholas,Tawney, Joseph G.,Henary, Maged
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- Bright fluorogenic squaraines with tuned cell entry for selective imaging of plasma membrane vs. endoplasmic reticulum
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A rational design of squaraine dyes with lipophilic and zwitterionic groups tunes cell entry, allowing for selective far-red/near-infrared imaging of plasma membrane vs. endoplasmic reticulum. They exhibit up to 110-fold fluorescence enhancement in biomembranes and enable cellular imaging at 1 nM concentration, which make them the brightest membrane probes to date.
- Collot, Mayeul,Kreder, Rémy,Tatarets, Anatoliy L.,Patsenker, Leonid D.,Mely, Yves,Klymchenko, Andrey S.
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supporting information
p. 17136 - 17139
(2015/12/01)
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- Microwave-Assisted Synthesis of Near-Infrared Fluorescent Indole-Based Squaraines
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(Graph Presented) A microwave-assisted method for the preparation of a wide color range of 2,3,3-trimethylindolenine-based squaraines and their intermediates is described. This practical approach allows the rapid preparation of both symmetrical and nonsymmetrical squaraine dyes, reducing reaction time from days to minutes with more than 2-fold improvement in product yields when compared to conventional methods.
- Barbero, Nadia,Magistris, Claudio,Park, Jinhyung,Saccone, Davide,Quagliotto, Pierluigi,Buscaino, Roberto,Medana, Claudio,Barolo, Claudia,Viscardi, Guido
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supporting information
p. 3306 - 3309
(2015/07/15)
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- Ultrasensitive near-infrared fluorescence-enhanced probe for in vivo nitroreductase imaging
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Nitroreductase (NTR) can be overexpressed in hypoxic tumors, thus the selective and efficient detection of NTR is of great importance. To date, although a few optical methods have been reported for the detection of NTR in solution, an effective optical probe for NTR monitoring in vivo is still lacking. Therefore, it is necessary to develop a near-infrared (NIR) fluorescent detection probe for NTR. In this study, five NIR cyanine dyes with fluorescence reporting structure decorated with different nitro aromatic groups, Cy7-1-5, have been designed and explored for possible rapid detection of NTR. Our experimental results presented that only a para-nitro benzoate group modified cyanine probe (Cy7-1) could serve as a rapid NIR fluorescence-enhanced probe for monitoring and bioimaging of NTR. The structure-function relationship has been revealed by theoretical study. The linker connecting the detecting and fluorescence reporting groups and the nitro group position is a key factor for the formation of hydrogen bonds and spatial structure match, inducing the NTR catalytic ability enhancement. The in vitro response and mechanism of the enzyme-catalyzed reduction of Cy7-1 have been investigated through kinetic optical studies and other methods. The results have indicated that an electro-withdrawing group induced electron-transfer process becomes blocked when Cy7-1 is catalytically reduced to Cy7-NH2 by NTR, which is manifested in enhanced fluorescence intensity during the detection process. Confocal fluorescence imaging of hypoxic A549 cells has confirmed the NTR detection ability of Cy7-1 at the cellular level. Importantly, Cy7-1 can detect tumor hypoxia in a murine hypoxic tumor model, showing a rapid and significant enhancement of its NIR fluorescence characteristics suitable for fluorescence bioimaging. This method may potentially be used for tumor hypoxia diagnosis.
- Li, Yuhao,Sun, Yun,Li, Jiachang,Su, Qianqian,Yuan, Wei,Dai, Yu,Han, Chunmiao,Wang, Qiuhong,Feng, Wei,Li, Fuyou
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supporting information
p. 6407 - 6416
(2015/06/02)
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- COLORING COMPOSITION, COLORING COMPOSITION FOR COLOR FILTER, AND COLOR FILTER
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PROBLEM TO BE SOLVED: To provide a coloring composition using a salt-forming compound, which is soluble in a solvent and can be used as a bright red dye, a coloring composition for a color filter, which is excellent in brightness, heat resistance, and a contrast ratio when used for a color filter, and a color filter having no generation of foreign substances on a coating film. SOLUTION: The coloring composition comprises a salt-forming compound of a cationic cyanine dye represented by general formula (1-1), and an organic solvent. In the formula, A1 and A2 each independently represent -CR12(R13)- or -S-; R1 to R11 each independently represent H, a substituted or unsubstituted alkyl group or the like; R12 and R13 each independently represent a substituted or unsubstituted alkyl group or the like; and Anion- represents a specific sulfate anion. COPYRIGHT: (C)2015,JPO&INPIT
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Paragraph 0173-0174
(2018/02/28)
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- Exploration of cyanine compounds as selective inhibitors of protein arginine methyltransferases: Synthesis and biological evaluation
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Protein arginine methyltransferase 1 (PRMT1) is involved in many biological activities, such as gene transcription, signal transduction, and RNA processing. Overexpression of PRMT1 is related to cardiovascular diseases, kidney diseases, and cancers; therefore, selective PRMT1 inhibitors serve as chemical probes to investigate the biological function of PRMT1 and drug candidates for disease treatment. Our previous work found trimethine cyanine compounds that effectively inhibit PRMT1 activity. In our present study, we systematically investigated the structure-activity relationship of cyanine structures. A pentamethine compound, E-84 (compound 50), showed inhibition on PRMT1 at the micromolar level and 6- to 25-fold selectivity over CARM1, PRMT5, and PRMT8. The cellular activity suggests that compound 50 permeated the cellular membrane, inhibited cellular PRMT1 activity, and blocked leukemia cell proliferation. Additionally, our molecular docking study suggested compound 50 might act by occupying the cofactor binding site, which provided a roadmap to guide further optimization of this lead compound.
- Hu, Hao,Owens, Eric A.,Su, Hairui,Yan, Leilei,Levitz, Andrew,Zhao, Xinyang,Henary, Maged,Zheng, Yujun George
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p. 1228 - 1243
(2015/03/04)
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