- 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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Read Online
- Synthesis of quaternary heterocyclic salts
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The microwave synthesis of twenty quaternary ammonium salts is described. The syntheses feature comparable yields to conventional synthetic methods reported in the current literature with reduced reaction times and the absence of solvent or minimal solvent.
- Winstead, Angela J.,Nyambura, Grace,Matthews, Rachael,Toney, Deveine,Oyaghire, Stanley
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Read Online
- 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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- 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 0262; 0264-0266
(2021/04/29)
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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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- METAL COMPLEX COMPOUND, NITROGEN-CONTAINING HETEROCYCLIC COMPOUND, DYE FOR OPTICAL FILTER, COLORING COMPOSITION AND OPTICAL FILTER
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PROBLEM TO BE SOLVED: To provide a metal complex compound capable of being suitably used as a dye or the like for optical filter such as a color filter as it can selectively absorbs light with predetermined wavelength and is excellent in heat resistance a
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Paragraph 0152-0153
(2017/11/01)
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- Squarylium cyanine dye and preparation method therefor
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The invention provides a squarylium cyanine dye and a preparation method therefor. The preparation method comprises the following steps: (1) firstly mixing a benzoindoles compound with squaric acid diethyl ester in an alcohol solvent, heating under the effect of triethylamine until reflux, reacting for 2-4 h, cooling, and carrying out suction filtration; (2) carrying out a reflux reaction on the product in the step 1) and malononitrile in the alcohol solvent under the effect of triethylamine, reacting for 10-30 min, washing with acetic acid, and carrying out suction filtration; and (3) heating the product in the step (2) and the benzoindoles compound with carboxyl in methylbenzene and n-butyl alcohol until reflux, and reacting for 7-10 h to obtain an end-product. The squarylium cyanine dye is relatively long in absorption and emission wavelength and good in light stability, active group carboxyl is introduced at the same time, and the squarylium cyanine dye can react with amino groups in biomolecules and is used for marking various biomolecules; and the synthetic method is simple, mild in condition and higher in yield, and provides good application prospects in the fields of molecular signature, fluorescence imaging and the like.
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Paragraph 0063
(2016/10/08)
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- A series of asymmetric squaraine cyanine small molecule and its preparation method and application
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The invention discloses a series of asymmetrical squarine micromolecules as well as a preparation method and an application thereof. Donor-receptor-donor type asymmetrical squarine micromolecules are formed by adopting two different electron-rich aromatic units as donors and leading 1,3-squaric acid cells with high electronic affinity into a conjugated system as receptors, so that micromolecule materials with low band gaps are acquired, and the absorption spectrum of the micromolecule materials can cover visual and near-infrared regions by 450-800nm; and meanwhile, the compounds prepared through the preparation method are good in dissolubility and film-forming property, which is very favorable for preparing organic solar cells with good performance.
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Paragraph 0051; 0053
(2016/10/07)
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- Correlating molecular character of NIR imaging agents with tissue-specific uptake
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Near-infrared (NIR) fluorescent contrast agents are emerging in optical imaging as sensitive, cost-effective, and nonharmful alternatives to current agents that emit harmful ionizing radiation. Developing spectrally distinct NIR fluorophores to visualize sensitive vital tissues to selectively avoid them during surgical resection of diseased tissue is of great significance. Herein, we report the synthetic variation of pentamethine cyanine fluorophores with modifications of physicochemical properties toward prompting tissue-specific uptake into sensitive tissues (i.e., endocrine glands). Tissue-specific targeting and biodistribution studies revealed localization of contrast agents in the adrenal and pituitary glands, pancreas, and lymph nodes with dependence on molecular characteristics. Incorporation of hydrophobic heterocyclic rings, alkyl groups, and halogens allowed a fine-tuning capability to the hydrophobic character and dipole moment for observing perturbation in biological activity in response to minor structural alterations. These NIR contrast agents have potential for clinical translation for intraoperative imaging in the delineation of delicate glands.
- Owens, Eric A.,Hyun, Hoon,Tawney, Joseph G.,Choi, Hak Soo,Henary, Maged
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p. 4348 - 4356
(2015/06/08)
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- Near-infrared-fluorescence imaging of lymph nodes by using liposomally formulated indocyanine green derivatives
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Liposomally formulated indocyanine green (LP-ICG) has drawn much attention as a highly sensitive near-infrared (NIR)-fluorescence probe for tumors or lymph nodes in vivo. We synthesized ICG derivatives tagged with alkyl chains (ICG-Cn), and we examined NIR-fluorescence imaging for lymph nodes in the lower extremities of mice by using liposomally formulated ICG-Cn (LP-ICG-Cn) as well as conventional liposomally formulated ICG (LP-ICG) and ICG. Analysis with a noninvasive preclinical NIR-fluorescence imaging system revealed that LP-ICG-Cn accumulates in only the popliteal lymph node 1 h after injection into the footpad, whereas LP-ICG and ICG accumulate in the popliteal lymph node and other organs like the liver. This result indicates that LP-ICG-Cn is a useful NIR-fluorescence probe for noninvasive in vivo bioimaging, especially for the sentinel lymph node.
- Toyota, Taro,Fujito, Hiromichi,Suganami, Akiko,Ouchi, Tomoki,Ooishi, Aki,Aoki, Akira,Onoue, Kazutaka,Muraki, Yutaka,Madono, Tomoyuki,Fujinami, Masanori,Tamura, Yutaka,Hayashi, Hideki
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p. 721 - 727
(2014/01/23)
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- Fluorescent Probe for Imaging Lymph Nodes
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Disclosed is a near-infrared fluorescent imaging agent comprising an indocyanine-based fluorescent dye and a liposome. The near-infrared fluorescent imaging agent of the present invention demonstrates high fluorescence intensity and a long anchoring time in sentinel lymph nodes, thereby making it useful for detecting sentinel lymph nodes in sentinel lymph node navigation surgery. Also disclosed is an indocyanine green derivative that is particularly suitable for use in the near-infrared fluorescent imaging agent of the present invention.
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Paragraph 0065; 0075
(2013/06/04)
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- Novel high performance asymmetrical squaraines for small molecule organic solar cells with a high open circuit voltage of 1.12 v
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An asymmetrically substituted squaraine ASQC bearing a 9-carbazyl substituent exhibits an extremely deep HOMO energy level of -5.46 eV and a relatively low bandgap of 1.65 eV, hence renders solution-processed organic solar cells with an impressive Vo
- Yang, Daobin,Yang, Qianqian,Yang, Lin,Luo, Qian,Huang, Yan,Lu, Zhiyun,Zhao, Suling
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supporting information
p. 10465 - 10467
(2013/11/06)
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- Synthesis and evaluation of carbocyanine dyes as PRMT inhibitors and imaging agents
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Protein arginine methylation regulates multiple biological processes. Deregulation of protein arginine methyltransferase (PRMT) activities has been observed in many disease phenotypes. Small molecule probes that target PRMTs with strong affinity and selectivity can be used as valuable tools to dissect biological mechanisms of arginine methylation and establish the role of PRMT proteins in a disease process. In this work, we report synthesis and evaluation of a class of carbocyanine compounds containing indolium, benz[e]indolium or benz[c,d]indolium heterocyclic moieties that bind to the predominant arginine methyltransferase PRMT1 and inhibit its methyltransferase activity at low micromolar potencies. In particular, the developed molecules have long wavelength colorimetric and fluorometric photoactivities, which can be used for optical and near-infrared fluorescence imaging in cells or biological tissues. Together, these new chemical probes have potential application in PRMT studies both as enzyme inhibitors and as fluorescent dyes for microscope imaging.
- Sinha, Sarmistha Halder,Owens, Eric A.,Feng, You,Yang, Yutao,Xie, Yan,Tu, Yaping,Henary, Maged,Zheng, Yujun George
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experimental part
p. 647 - 659
(2012/09/08)
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- A convenient synthesis of cyanine dyes: Reagents for the labeling of biomolecules
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Four tetramethylindo(di)carbocyanine-derived carboxylic acids have been prepared using a modified one-pot procedure for the dye assembly. The acids were converted into oxysuccinimide esters and phosphoramidite reagents. The efficiency of the reagents in t
- Kvach, Maksim V.,Ustinov, Alexey V.,Stepanova, Irina A.,Malakhov, Andrei D.,Skorobogatyi, Mikhail V.,Shmanai, Vadim V.,Korshun, Vladimir A.
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experimental part
p. 2107 - 2117
(2009/04/05)
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