Design, Preparation, and Characterization of Novel Calix[4]arene Bioactive Carrier for Antitumor Drug Delivery

Abstract

An amphiphilic and bioactive calix[4]arene derivative 8 (CA) is designed and successfully synthesized from tert-butyl calix[4] arene 1 by sequential inverse F-C alkylation, nitration, O-alkylation, esterification, aminolysis, reduction, and acylation reaction. The blank micelles of FA-CA and doxorubicin (DOX) loaded micelles FA-CA-DOX are prepared subsequently undergoing self-assembly and dialysis of CA and DSPE-PEG2000-FA. The drug release kinetics curve of the encapsulated-DOX micelle demonstrates a rapid release under mild conditions, indicating the good pH-responsive ability. Furthermore, the cytotoxicity of DOX-loaded micelle respect to the blank micelle against seven different human carcinoma (A549, HeLa, HepG2, HCT116, MCF-7, MDA-MB231, and SW480) cells has been also investigated. The results confirm the more significant inhibitory effect of DOX-loaded micelle than those of DOX and the blank micelles. The CDI calculations show a synergistic effect between blank micelles and DOX in inducing tumor cell death. In conclusion, FA-CA micelles reported in this work was a promising drug delivery vehicle for tumor targeting therapy.

Role of Calixarene in Chemotherapy Delivery Strategies

“…To study the release kinetics of DOX from micelles in vitro, the method of dialysis in phosphate buffered saline solution, at various pH conditions, was performed. Initially the DOX fraction present between the hydrophilic and hydrophobic portion of the micelle is released rapidly, then, the DOX fraction encapsulated in the micelle core is released slowly for 24–48 h [ 59 ]. Another study conducted on doxorubicin-containing liposomes shows that this DDS (unlike calixarene) can encapsulate 89% of DOX and release 41% of it in a controlled manner for six hours.…”

Synthesis, Characterization and Host-Guest Complexation of Asplatin: Improved In Vitro Cytotoxicity and Biocompatibility as Compared to Cisplatin

“…Supramolecular host molecules, comprising calix[n]arenes (CXs), cyclodextrins (CDs), cucurbiturils (CBs), and pillararenes, have been suggested as smart drug delivery platforms [1,22,23] and have been used as host molecules to encapsulate various chemotherapeutic drugs to improve their bioavailability, prevent their premature degradation in the bloodstream, and increase their targeted intracellular uptake into cancer cells [1][2][3]. Lately, calix[n]arenes (n = 4, 6, and 8) have been employed in drug targeting [24][25][26]. Calixarenes are idyllic host molecules that are synthesized by linking phenolic rings via methylene bridges encompassing three regions; (1) a lower rim with a phenolic hydroxyl group, (2) an upper rim with a para-substituent of a phenolic unit, and (3) a hydrophobic π electron-rich central cavity.…”

Green Synthesis of Silver Nanoparticles Using the Plant Extract of Acer oblongifolium and Study of Its Antibacterial and Antiproliferative Activity via Mathematical Approaches

“…This maple is one of the few that remains green in winter. Acer oblongifolium is found in eastern, central, and southeastern Asia, from northeast India and Tibet to Japan, including northern Indochina and southern China [14].…”