Abstract

A recently reported functionalization of single and multi-walled carbon nanotubes, based on a cycloaddition reaction between carbon nanotubes and a pyrrole derived compound, was exploited for the formation of a doxorubicin (DOX) stacked drug delivery system. The obtained supramolecular nano-conveyors were characterized by wide-angle X-ray diffraction (WAXD), thermogravimetric analysis (TGA), high-resolution transmission electron microscopy (HR-TEM), and Fourier transform infrared (FT-IR) spectroscopy. The supramolecular interactions were studied by molecular dynamics simulations and by monitoring the emission and the absorption spectra of DOX. Biological studies revealed that two of the synthesized nano-vectors are effectively able to get the drug into the studied cell lines and also to enhance the cell mortality of DOX at a much lower effective dose. This work reports the facile functionalization of carbon nanotubes exploiting the “pyrrole methodology” for the development of novel technological carbon-based drug delivery systems.

Highlights

  • Carbon nanotubes (CNT) have a peculiar combination of electrical, thermal, and mechanical properties [15,16,17,18]

  • Characterization of the adducts was carried out employing thermogravimetric analysis (TGA), wide-angle X-ray diffraction (WAXD), high-resolution transmission electron microscopy (HR-TEM), and Fourier transform infrared spectroscopy (FT-IR)

  • We reported the functionalization of single and multi-walled carbon nanotubes with a pyrrole polypropylene glycol derived compound exploiting a Diels-Alder reaction

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Summary

Introduction

The selected sp carbon allotrope was functionalized by mixing it with the pyrrole compound (PyC) and giving either mechanical or thermal energy [37] In the latter case, it was shown [37] that the graphene layers constituting the bulk structure of the carbon substrate remained substantially unaltered. Preliminary indications have been reported [39] that the functionalization with different pyrrole compounds leads to the modification of the solubility parameter of graphene layers in a broad range of values. This manuscript reports on the functionalization of single and multiwalled carbon nanotubes on indicated as CNT with a pyrrole compound obtained from HD and an amine-terminated poly(propylene glycol). Preliminary biological studies revealed that two of the synthesized nano-vectors are effectively able to release the drug in situ

Materials
General Procedure
DOX Calibration Curve by UV-Vis Spectroscopy
DOX Release From CNT Nano Complexes
Wide-Angle X-Ray Diffraction
Calculation of the Hansen Solubility Sphere and Hansen Solubility Parameters
Cell Cultures
Cell Viability Assay
Statistical Analysis
Models Preparation
Molecular Dynamics Simulations
Findings
Conclusions

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