Synthesis of Carboxamide‐Functionalized Multiwall Carbon Nanotubes via Ugi Multicomponent Reaction: Water‐Dispersible Peptidomimetic Nanohybrid as Controlled Drug Delivery Vehicle

Abstract

This paper describes a direct synthesis of novel and valuable carboxamide functionalized multiwall carbon nanotubes (carboxamide-f-MWCNTs) for the development of new nanovectors through covalent functionalization via a one-pot four-component Ugi reaction. This efficient synthetic approach is facile and straightforward procedure for the synthesis of peptidomimetic coated MWCNTs from simple and readily starting materials including aniline, benzaldehyde, isocyanide and the carboxylated MWCNT as an acid component. The new synthesized nanobiohybrid was fully characterized. Also, the stability of nanobiohybrid was assessed using Zeta potential and particle size analyses. The synthesized nanobiohybrid presents unprecedented high and long term dispersity and stability in water. The performance of the nanobiohybrid for the controlled release of folic acid, as a model drug, was investigated and the results depicted pH dependent slow drug release behavior of nanobiohybrid. In addition, biocompatibility and cytotoxicity of carboxamide-f-MWCNTs were examined and no obvious adverse effects on the viability of NIH-3T3 cells were observed. The results manifested its valuable applicability in controlled release drug delivery systems.

Materials Functionalization with Multicomponent Reactions: State of the Art

“…In 2017, Shaabani and co-worker reported a direct synthesis of novel carboxamide-functionalized MWCNTs (carboxamide- f -MWCNTs) as a nanovector through a covalent functionalization via Ugi-4CR approach . The expedient approach was commenced through the reaction of carboxylated MWCNT as an acid component in Ugi-4CR.…”

“…In 2017, Shaabani and co-worker reported a direct synthesis of novel carboxamide-functionalized MWCNTs (carboxamidef-MWCNTs) as a nanovector through a covalent functionalization via Ugi-4CR approach. 41 The expedient approach was commenced through the reaction of carboxylated MWCNT as an acid component in Ugi-4CR. By this functionalization in a single step, the peptidomimetic coated MWCNT nanohybrids were able to serve as promising biocompatible nanocarriers with excellent pH dependent sustainability which prolonged the drug release profile and prevented premature release of Folic acid (FA).…”

Multicomponent Reactions-Based Modified/Functionalized Materials in the Biomedical Platforms

“…Besides, the (18), aniline (19), and cyclohexyl isocyanide (11) for the development of peptidomimetic coated nanovectors (20) (Figure 1a). 75 In water, nano-biohybrid exposed exclusive long and high term stability and dispersity owing to the formation of a valuable carboxamide group with a high hydrophilic nature onto MWCNTs. The controlled release of folic acid showed a pHresponsive slow drug release manner with nonsignificant toxicity against NIH-3T3 cells (Figure 1b).…”

Rhodanine‐Furan Bis‐Heterocyclic Frameworks Synthesis via Green One‐Pot Sequential Six‐Component Reactions: A Synthetic and Computational Study

“…Inspired by the above facts and encouraged by our previous studies in development of MCRs particularly based on higher‐order MCRs, herein, we describe an efficient construction of novel rhodanine‐furan bis ‐heterocyclic frameworks based on the union of MCRs synthetic routes via a tandem Michael/domino cycloaddition/zwitterionic adduct formation/Mumm rearrangement/[1+4] cycloaddition processes sequence. This synthetic route is directly carried out by a one‐pot sequential six‐component reaction from commercially available substrates such as diverse of primary amines, carbon disulfide, maleic anhydride, dialkyl acetylenedicarboxylates as well as various isocyanides in water under ultrasound irradiation conditions at ambient temperature within 80–100 minutes without using any catalyst, additive or organic solvents (Scheme ).…”