41532-84-7Relevant articles and documents
Synthesis and spectroscopic study of highly fluorescent β-enaminone based boron complexes
Kumbhar, Haribhau S.,Gadilohar, Balu L.,Shankarling, Ganapati S.
, p. 80 - 87 (2015)
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.
Synthesis of advanced fluorescent probes — water-soluble symmetrical tricarbocyanines with phosphonate groups
Podrugina,Temnov,Doroshenko,Kuzmin,Nekipelova,Proskurnina,Zefirov
, p. 2722 - 2728 (2016)
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.
Near-Infrared Heptamethine Cyanine Dyes for Nanoparticle-Based Photoacoustic Imaging and Photothermal Therapy
St. Lorenz, Anna,Buabeng, Emmanuel Ramsey,Taratula, Oleh,Taratula, Olena,Henary, Maged
, p. 8798 - 8805 (2021/06/28)
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.
Evaluation of asymmetric orthogonal cyanine fluorophores
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.
, (2020/08/24)
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.