Self-Assembling Cyclodextrin-Based Nanoparticles Enhance the Cellular Delivery of Hydrophobic Allicin

Abstract

Most chemotherapeutics are hydrophobic molecules and need to be converted into hydrophilic formulations before administration. To address this issue, a novel cyclodextrin-based nanoparticle was proposed as a versatile carrier for cellular delivery of hydrophobic molecules. First, the effect of the polylysine (PL)/NH2-β-cyclodextrin (NH2-β-CD) ratio on particle size and encapsulation efficiency in prepared complexes was investigated. Subsequently, transmission electron microscopy images showed that the sizes of PL/NH2-β-CD nanoparticles ranging from 10 to 260 nm decreased with the reduction in the PL/NH2-β-CD ratio, which was completely consistent with the findings of size distributions. At a PL/NH2-β-CD ratio of 10, the surface charge on the PL/NH2-β-CD nanoparticle was maximized at (+52.8 mV), and encapsulation efficiency was optimal (47.2%), which revealed a great advantage in delivery of hydrophobic allicin. In addition, the positive charge of PL chains facilitated the cellular uptake of the PL/NH2-β-CD-DOX by interacting with the negatively charged cell membrane. Conclusively, this study suggests that the combination of allicin and PL/NH2-β-CD nanoparticles acting on the S and G2/M phases in cell cycle regulation induces apoptosis and exhibits substantial application in killing cancer cells.

Multicharged cyclodextrin supramolecular assemblies

“…To address this issue, He and co-workers reported that CD-based nanoparticles could be used as a multifunctional carrier for the enhanced cellular delivery of the hydrophobic compound allicin. 272 Positively charged polylysine (PL) was attached to NH 2 -β-CD to synthesize the amphiphilic PL/NH 2 -β-CD carrier, which facilitated cellular uptake by using the high affinity of PL for negatively charged cell membranes. Compared with the parent β-CD (Fig.…”

Supramolecular Biopharmaceutical Carriers Based on Host–Guest Interactions

“…Cyclodextrin (CD) is a cyclic oligosaccharide obtained from starch by enzymatic hydrolysis, mainly containing 6, 7 and 8 glucopyranose units forming α-CD, β-CD, and γ-CD respectively. α-, β- and γ-CD have hydrophobic cavities with internal diameters of approximately 0.47–0.53, 0.60–0.65 and 0.75–0.83 nm, respectively. − Hydroxyl groups within the cyclodextrins are not only responsible for aqueous solubility but also allow the hydroxyl groups to interact with the hydrophilic components, making the hydrophobic drugs water-soluble complexes. − In this inclusion complexation phenomenon, multiple cyclodextrin fragments can be involved by encapsulating one or more guest molecules, which can form a variety of complexation phenomena such as 1:1, 1:2, 2:2, etc. Therefore, this section is divided into three main sections on cyclodextrin-inclusive drugs, focusing on (1) natural cyclodextrin-inclusive drugs, (2) modified cyclodextrin-inclusive drugs and (3) cyclodextrin polymer-inclusive drugs.…”

Simple Strategy Preparing Cyclodextrin Carboxylate as a Highly Effective Carrier for Bioactive Compounds

“…However, the modification process required the use of organic chemicals, complicated procedures, and long reaction times, which reduces its commercial viability. In another study, Chen et al 39 synthesized a chemically modified β-CD as a host molecule for a hydrophobic drug (20(S)-protopanaxatriol) and reported that the water dispersibility of the drug increased around 532-fold after encapsulation. Nevertheless, the preparation procedure used in that study to create the modified β-CD also involved the use of organic solvents and was relatively time consuming.…”