Fluorescence Tumor-Imaging Using a Thermo-Responsive Molecule with an Emissive Aminoquinoline Derivative

Abstract

We synthesized (2,4-trifluoromethyl-7-N-bis(2,5,8,11-tetraoxatridecane-13-yl)-aminoquinoline) TFMAQ-diEg4, an emissive aminoquinoline derivative that incorporated two tetraethyleneglycol chains into an amino group. TFMAQ-diEg4 showed fluorescence and thermo-responsive properties accompanied by a lower critical solution temperature (LCST), due to the introduction of the oligoethylene glycol chain. This thermo-responsive LCST behavior occurred at the border of a cloud point. Below and above the cloud point, self-assemblies of 6-7-nm nanoparticles and ~2000-nm microparticles were observed, in vitro. In addition, TFMAQ-diEg4 showed a high solubility, over 20 mM for aqueous solution, in vivo, which not only prevented thrombosis but also allowed various examinations, such as single intravenous administration and intravenous drips. Intravenous administration of TFMAQ-diEg4, to tumor-bearing, mice led to the accumulation of the molecule in the tumor tissue, as observed by fluorescence imaging. A subset of mice was treated with local heat around their tumor tissue and an intravenous drip of TFMAQ-diEg4, which led to a high intensity of TFMAQ-diEg4 emission within the tumor tissue. Therefore, we revealed that TFMAQ-diEg4 was useful as a fluorescence probe with thermo-responsive properties.

Characterization and Water-Proton Longitudinal Relaxivities of Liposome-Type Radical Nanoparticles Prepared via a Supramolecular Approach

“…To achieve this, the fluorescence changes in various fluorophores were observed (Scheme (c)). We selected TFMAQ-diHEG , TFMAQ-diMe , and 15Nap-Cl as the fluorophores − because these fluorophores show medium fluorescence intensities in polar solvents. Furthermore, these fluorophores possess different water solubilities and fluorescence quantum yields (Scheme and Table ).…”

Fabrication of Antheraea pernyi Silk Fibroin-Based Thermoresponsive Hydrogel Nanofibers for Colon Cancer Cell Culture

“…Particularly in the field of tissue engineering and regenerative medicine, thermoresponsive PNIPAAm exposed immense potential, as it enabled the creation and harvest of biologically functional products called “cell sheets” through the control of the dynamic environment for cells upon a change in temperature [ 21 ]. Hence, it has important applications for thermoresponsive polymers as cancer cell culture platforms, such as fluorescence tumor imaging [ 22 ], drug delivery in tumor screening and anti-cancer treatment [ 23 ]. PNIPAAm-based scaffolds as in vitro tumor culture models have good application in the previous reported, which encapsulate cells in physically cross-linked viscoelastic scaffolds at body temperature and easily release the cells by cooling to room temperature [ 24 ].…”

Selective synthesis of substituted amino-quinoline derivatives by C-H activation and fluorescence evaluation of their lipophilicity-responsive properties

“…We reported that TFMAQ exhibited fluorescence colour changes depending on solvent polarity and crystalline phase transition. The TFMAQ chromophore was further applied to thermo-responsive nanomaterials as in vivo tumour-imaging agent 23,24 . The TFMAQs were also derivatized to phenyl aromatic-substituted amine analogues to investigate the photophysical properties at solid state 25,26 .…”