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Relevant academic research and scientific papers

Single photon DNA photocleavage at 830 nm by quinoline dicarbocyanine dyes

We have synthesized symmetrical carbocyanine dyes in which two 4-quinolinium rings are joined by a pentamethine bridge that is meso-substituted with H or Cl. Irradiation of the halogenated dye at 830 nm produces hydroxyl radicals that generate DNA direct

Synthesis, crystal structure, spectral and thermodynamic properties of one benzoindole pentamethine cyanine dye

One benzoindole pentamethine cyanine dye was synthesized and characterized by 1H NMR, IR, MS and UV-Vis spectra. The UV-Vis absorption and fluorescence spectra of the dye in chloroform, dimethyl sulfoxide, acetone, ethanol and methanol were investigated, and the λmax of the dye was in the region 682.0-689.0 nmwith large molar extinction coefficients (ε > 105M-1cm-1) in different solvents. The structure of the dye was also characterized and analyzed by X-ray diffraction. Crystallographic data revealed that the dye belonged to orthorhombic, with space group P212121, a = 10.059(2) A, b = 15.098(4) A, c = 24.989(6) A, V = 3794.8(15) A3, Z = 4. TheC-H·F intermolecular hydrogen bonds were displayed in the molecular system, which were effective in the molecular packing. The aggregation behavior and thermodynamic properties of the dye in aqueous methanol solution were also studied by means of UV-Vis spectroscopy methods. The results indicated that the dye existed monomer-dimer equilibrium in aqueous methanol solutions. The fundamental properties of the dye, such as the dimeric association constant KD, the dimeric free energy ΔGD, the dimeric entropy ΔSD, and the dimeric enthalpy ΔHD were determined. The ΔHD of the dye was -46.0 kJ mol -1.

COMPOUNDS FOR PHOTODYNAMIC THERAPY AND RELATED USES

Disclosed herein are symmetrical and unsymmetrical carbocyanine dyes. Irradiation of the dyes generates reactive species which contribute to DNA damage. The dyes are useful for the treatment of various cancers and cell growth disorders.

Easily-modified near-infrared region II organic small molecule dye and synthetic method and application thereof

The invention provides an easily-modified near-infrared region II organic small molecule dye and a synthetic method and application of the easily-modified near-infrared region II organic small molecule dye. The near-infrared region II fluorescent dye belongs to polymethenyl pyran or polymethenyl thiapyran salt organic small molecules, and is prepared by a condensation reaction of polymethenyl aniline salt with pyran or thiopyran salt. The synthetic raw materials are easy to obtain, the cost is low, the preparation process is simple, the yield is high, and large-amount synthesis can be achieved. The purpose of adjusting the fluorescence emission spectrum is achieved by changing an intramolecular polymethenyl chain and hetero atom species. The small molecule dye has the maximum emission wavelength range of 1000-1200 nm, and is high in fluorescence quantum yield, good in light stability and quite applicable to living imaging. The small molecule dye can be linked to groups with specific functions by click chemistry for a variety of bioimaging application. Near-infrared region II fluorescent living imaging achieves low background noise, strong fluorescence signal and high signal-to-noise ratio.

Polymethine Thiopyrylium Fluorophores with Absorption beyond 1000 nm for Biological Imaging in the Second Near-Infrared Subwindow

Small-molecule fluorescence imaging in the second near-infrared (NIR-II, 1000-1700 nm) window has gained increasing interest in clinical application. Till now, very few studies have been exploited in the small-molecule fluorophores with both excitation and emission in the NIR-II window. Inspired by the indocyanine green structure, a series of polymethine dyes with both absorption and emission in the NIR-II window have been developed for NIR-II imaging, providing the feasibility to directly compare optical imaging in the NIR-IIa (1300-1400 nm) subwindow under 1064 nm excitation with that in the NIR-II window under 808 nm excitation. The signal-background ratio and the tumor-normal tissue ratio achieved great improvement under 1064 nm excitation in the imaging of mouse blood pool and U87 glioma tumors. Our study not only introduces a broadband emission fluorophore for both NIR-II and NIR-IIa imaging, but also reveals the advantages of NIR-II excitation over NIR-I in in vivo imaging.

Near-Infrared Illumination of Native Tissues for Image-Guided Surgery

Our initial efforts to prepare tissue-specific near-infrared (NIR) fluorescent compounds generated successful correlation between physicochemical properties and global uptake in major organs after systemic circulation and biodistribution. Herein, we focus on the effects on biodistribution based on modulating electronic influencing moieties from donating to withdrawing moieties at both the heterocyclic site and through meso-substitution of pentamethine cyanine fluorophores. These selected modifications harnessed innate biodistribution pathways through the structure-inherent targeting, resulting in effective imaging of the adrenal glands, pituitary gland, lymph nodes, pancreas, and thyroid and salivary glands. These native-tissue contrast agents will arm surgeons with a powerful and versatile arsenal for intraoperative NIR imaging in real time.

Endocrine-specific NIR fluorophores for adrenal gland targeting

The adrenal glands (AGs) are relatively small yet require definitive identification during their resection, or more commonly their avoidance. To enable image-guided surgery involving the AGs, we have developed novel near-infrared (NIR) fluorophores that target the AGs after a single intravenous injection, which provided dual-NIR image-guided resection or avoidance of the AGs during both open and minimally-invasive surgery.

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.

Carbocyanines for G-Quadruplex DNA Stabilization and Telomerase Inhibition

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.

Oxidative cleavage of DNA by pentamethine carbocyanine dyes irradiated with long-wavelength visible light

Here we report the synthesis of seven symmetrical carbocyanine dyes in which two nitrogen-substituted benz[e]indolium rings are joined by a pentamethine bridge that is meso-substituted with chlorine or bromine versus hydrogen. The heteroatom of benz[e]indolium is modified with a phenylpropyl, methyl, or cationic quaternary ammonium group. In reactions containing micro molar concentrations of halogenated dye, irradiation at 575, 588, 623, or 700 nm produces good photocleavage of plasmid DNA. UV-visible spectra show that the carbocyanines are in their H-aggregated and monomeric forms. Scavenger experiments point to the involvement of singlet oxygen and hydroxyl radicals in DNA photocleavage.