137107-72-3

Usage

InChI:InChI=1/C19H24N.HI/c1-5-6-13-20-14(2)19(3,4)18-16-10-8-7-9-15(16)11-12-17(18)20;/h7-12H,5-6,13H2,1-4H3;1H/q+1;/p-1

Upstream product

• 542-69-8 1-iodo-butane 
• 41532-84-7 2,3,3-trimethylbenzo[e]indole 
• 2243-58-5 2-naphthylhydrazine hydrochloride 
• 563-80-4 3-methyl-butan-2-one 
• 2243-57-4 2-hydrazinonaphthalene 

Downstream Products

• 1196490-92-2 C₂₇H₃₁ClNO⁽¹⁺⁾*I^(1-) 
• 886046-46-4 3-butyl-2-((1E,3E)-3-(3-butyl-1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene)prop-1-en-1-yl)-1,1-dimethyl-1H-benzo[e]indol-3-ium iodide 

Relevant academic research and scientific papers

Synthesis and optical properties of near-infrared meso-phenyl-substituted symmetric heptamethine cyanine dyes

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.

Synthesis of quaternary heterocyclic salts

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.

Near-Infrared Heptamethine Cyanine Dyes for Nanoparticle-Based Photoacoustic Imaging and Photothermal Therapy

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.

NOVEL SQUARYLIUM COMPOUNDS, AND COMPOSITIONS COMPRISING SAME

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.

N-alkylated linear heptamethine polyenes as potent non-azole leads against Candida albicans fungal infections

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.

METAL COMPLEX COMPOUND, NITROGEN-CONTAINING HETEROCYCLIC COMPOUND, DYE FOR OPTICAL FILTER, COLORING COMPOSITION AND OPTICAL FILTER

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

Squarylium cyanine dye and preparation method therefor

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.

A series of asymmetric squaraine cyanine small molecule and its preparation method and application

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.

Correlating molecular character of NIR imaging agents with tissue-specific uptake

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.

Near-infrared-fluorescence imaging of lymph nodes by using liposomally formulated indocyanine green derivatives

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.