- Synthesis and spectroscopic study of highly fluorescent β-enaminone based boron complexes
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The newly synthesized 1, 1, 2-trimethyl-1H benzo[e]indoline based β-enaminone boron complexes exhibited the intense fluorescence (Fmax = 522-547 nm) in solution as well as in solid state (Fmax = 570-586 nm). These complexes exhibited large stoke shift, excellent thermal and photo stability when compared to the boron dipyrromethene (BODIPY) colorants. Optimized geometry and orbital distribution in ground states were computed by employing density functional theory (DFT). The cyclic voltammetry study revealed the better electron transport ability of these molecules than current electroluminescent materials like tris(8-hydroxyquinoli-nato)-aluminium (Alq3) and BODIPY, which can find application in electroluminescent devices.
- Kumbhar, Haribhau S.,Gadilohar, Balu L.,Shankarling, Ganapati S.
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- Cyanine Nanocage Activated by Near-IR Light for the Targeted Delivery of Cyclosporine A to Traumatic Brain Injury Sites
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More than 2.8 million annually in the United States are afflicted with some form of traumatic brain injury (TBI), where 75% of victims have a mild form of TBI (MTBI). TBI risk is higher for individuals engaging in physical activities or involved in accidents. Although MTBI may not be initially life-threatening, a large number of these victims can develop cognitive and physical dysfunctions. These late clinical sequelae have been attributed to the development of secondary injuries that can occur minutes to days after the initial impact. To minimize brain damage from TBI, it is critical to diagnose and treat patients within the first or "golden" hour after TBI. Although it would be very helpful to quickly determine the TBI locations in the brain and direct the treatment selectively to the affected sites, this remains a challenge. Herein, we disclose our novel strategy to target cyclosporine A (CsA) into TBI sites, without the need to locate the exact location of the TBI lesion. Our approach is based on TBI treatment with a cyanine dye nanocage attached to CsA, a known therapeutic agent for TBI that is associated with unacceptable toxicities. In its caged form, CsA remains inactive, while after near-IR light photoactivation, the resulting fragmentation of the cyanine nanocage leads to the selective release of CsA at the TBI sites.
- Black, Caroline E.,Zhou, Eugene,Deangelo, Caitlin,Asante, Isaac,Yang, Rong,Petasis, Nicos A.,Louie, Stan G.,Humayun, Mark
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- Synthesis of advanced fluorescent probes — water-soluble symmetrical tricarbocyanines with phosphonate groups
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A method for the synthesis of a series of water-soluble heptamethine indocyanine dyes containing a phosphonate group in the substituent bonded to the quaternary nitrogen atom of the indolenine moiety has been developed.
- Podrugina,Temnov,Doroshenko,Kuzmin,Nekipelova,Proskurnina,Zefirov
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- Synthesis and photochromic properties of spiro(benzindoline-naphthoxazines)
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A new photochromic compound belonging to the class of spiro(indoline-naphthoxazines) was synthesized.Nitration of this compound was carried out and the structures of two photochromic nitro-substituted products were determined.The photochromic properties of the products were studied in solvents of different polarity. - Key words: photochromism; spiro(indoline-naphthoxazines), nitration.
- Nedoshivin, V. Yu.,Zaichenko, N. L.,Shienok, A. I.,Marevtsev, V. S.
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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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- Adenine-based flower-elite probe and preparation method and application thereof
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The present invention belongs to the field of chemical analysis testing, specifically relates to an adenine-based flower cyanine probe and preparation method and application thereof. The CY5.5 dye is synthesized by a four-step reaction. The CY5.5 dye was then reacted with adenine under N, N'-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP) conditions, and the resulting crude product was separated by thin layer chromatography to obtain the final product. The flower probe obtained by the present invention has excellent optical properties and the role of recognizing hemoglobin, which is conducive to the detection of hemoglobin.
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Paragraph 0013; 0023-0024; 0033-0034; 0039-0040
(2022/01/07)
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- Evaluation of asymmetric orthogonal cyanine fluorophores
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Pentamethine cyanine (Cy5) fluorophores have proven to be versatile imaging agents (i.e., tracers) for a range of micro- and macroscopic imaging applications, including image-guided surgery. In this study the relationship between the structure of asymmetric Cy5 fluorophores and their photophysical properties was studied. To this end, seven Cy5 analogues, bearing orthogonal N-indole substituents (H, SO3?, or benzene), were synthesised and evaluated. In-depth analysis revealed that introduction of sulfonates enhanced the fluorescence brightness and photostability, while reducing the lipophilicity, serum binding and stacking tendency. The addition of benzene moieties induced a bathochromic shift of 10–20 nm, increased the lipophilicity (LogP = -1.56–1.23) and serum binding (67.3–93.8percent bound), as well as negatively impacted the brightness (0.74–42.9 · 103 M?1 cm?1), photostability (24.4–90.6percent remaining), and stacking tendency. Chemical stability was uninfluenced by the substitution pattern. Additionally, the generation of a c[RGDyK]-based hybrid tracer based on one of these fluorophores in combination with a diethylenetriaminepentaacetic acid (DTPA) chelate and an 111In-isotope was reported. This compound was evaluated in vitro using αvβ3-overexpressing Geβ3 cells and in vivo using a 4T1 mouse tumour model. Overall, the presented results imply that alterations of the asymmetrical orthogonal Cy5 fluorophore structure have impact on the (photo)physical properties. Furthermore, the orthogonal Cy5 fluorophore framework can readily be applied in tracer development.
- Boutkan, Michael S.,Buckle, Tessa,Hensbergen, Albertus W.,Welling, Mick M.,Wester, Hans-Jürgen,de Kleer, Mathijs A. C.,van Leeuwen, Fijs W. B.,van Willigen, Danny M.,van der Wijk, Felicia A.
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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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- Carbocyanines for G-Quadruplex DNA Stabilization and Telomerase Inhibition
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Cyanines which selectively bind to G-quadruplex DNA complexes, particularly quadruplexes expressed in cancer cells, and methods of making and using thereof are described herein. The cyanine can be a symmetrical or unsymmetrical streptocyanine, hemicyanine, closed chain cyanine, or combinations thereof. The cyanine is preferably substituted with one or more groups that minimize or prevent aggregation of the cyanine and/or inhibit binding of the cyanine to duplex DNA. One or more of the cyanines can be formulated with one or more pharmaceutical excipients and/or carrier to prepare pharmaceutical compositions suitable for administration to a patient, particular a human patient. The compounds and compositions described herein can be used to treat diseases or disorders characterized by the expression of G-quadruplex DNA, such as cancer.
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Paragraph 0312; 0313
(2014/05/25)
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- Method for the preparation of high purity substituted benz ?E! indoles and the alkaline salts thereof
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Method for the preparation of high purity substituted benz?e!indoles corresponding to the general formula STR1 comprising the preparation of an arylhydrazine which is subjected to a Fischer indole synthesis with a suitable ketone, the benz?e!indole thus obtained being reacted with a radical R6, followed by subjection to a purification step. This method may more particularly be applied to the synthesis of Indocyanine Green.
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