Highly fluorescent resorcinarene cavitand nanocapsules with efficient renal clearance

Abstract

Nanomaterial based imaging approaches hold substantial promise in addressing current diagnostic and therapeutic challenges. One of the key requirements for the successful clinical translation of nanomaterials is their complete clearance from the body within a reasonable time period preferably via the renal filtration route. This article describes the synthesis of highly fluorescent, water soluble, resorcinarene cavitand nanocapsules and demonstrates their effective renal clearance in mice. The synthesis and functionalization of nanocapsules was accomplished in a one-pot operation via thiol-ene reactions without involving self-assembly, sacrificial templates or emulsions. Water soluble resorcinarene cavitand nanocapsules obtained by this approach were covalently functionalized with Alexa Fluor 750. Highly fluorescent nanocapsules with hydrodynamic diameters of 122 nm and 68 nm and extinction coefficients of 1.3 × 10(9) M(-1) cm(-1) and 1.5 × 10(8) M(-1) cm(-1) respectively were prepared by varying the reaction conditions. The in vivo biodistribution and clearance of these nanocapsules in mice followed by whole-body fluorescence imaging showed that they were both cleared renally within a few hours. Given the inherent encapsulation capabilities of nanocapsules, the renal clearance demonstrated in this work opens up new opportunities for their theranostic applications especially for targeting and treating the urinary tract.

The “Nitrogen Effect”: Complexation with Macrocycles Potentiates Fused Heterocycles to Form Halogen Bonds in Competitive Solvents

“…Small shifts of 0.15 and 0.14 ppm lower were observed. The 1 H, 19 F and 13 C NMRs all reveal very weak to no XB between Qu and XB1 in this mixed and highly competing methanol-chloroform solvent system. However, we know that MeC2 forms endo-complexes with either Qu or Phen in this mixed solvent system.…”

Fluorophore Localization Determines the Results of Biodistribution of Core-Shell Nanocarriers

“…In addition, these researchers proved the presence of entire nanocapsules in the urine of mice collected postmortem. 26 As this phenomenon was observed for liquid core nanocarriers, next, we investigated the differences in biodistribution between liquid nanoemulsion core (NC-RhB-PEG) and solid biodegradable polymeric core (PCL-RhB-PEG) and solid nonbiodegradable polystyrene latex core (LX-RhB-PEG) nanocarriers. Despite differences in the core architecture no differences were observed in the biodistribution profile and removal pathways of the tested nanocarriers labeled within the shell (NC-RhB-PEG, PCL-RhB-PEG and LX-RhB-PEG).…”

In vivo fluorescence imaging of hepatocellular carcinoma using a novel GPC3-specific aptamer probe

“…Due to its long wavelength emission, enhanced photostability and pH-insensitivity over a wide molar range, AF750 was chosen as the fluorescent dye in the in vivo NIR fluorescence imaging to obtain stable images in this study (33,34). In order to avoid the overlap between the tumor and the surrounding tissues in the direction of fluorescence imaging, which could impair the accurate measurement of the tumor fluorescence intensity, the tumor cells were inoculated subcutaneously at the lateral flank of the mice to minimize this superimposition effect.…”