Tumor microenvironment responsive supramolecular glyco-nanovesicles based on diselenium-bridged pillar[5]arene dimer for targeted chemotherapy

Abstract

Supramolecular glyco-nanovesicles (SeSe-(P5)2⊃Man-NH3+) based on the host-guest complex of diselenium-bridged pillar[5]arene dimer and mannose derivative have been successfully developed for the first time, which possessed tumor microenvironment-responsiveness and specific targetability...

Pillararene-based supramolecular systems for theranostics and bioapplications

“…One common method is loading hydrophobic drugs in the hydrophobic regions of these self-assemblies or hydrophilic drugs in the intrinsic hollow pores of the vesicles. Pei et al [36] reported a tumor microenvironment-responsive drug delivery system with self-targeting capability based on vesicles formed from a diselenium-bridged pillar[5]arene dimer (1, Figure 3). The host-guest recognition of the pillararene facilitated the assembly of vesicles by binding a hydrophilic mannose-containing guest (2) and forming a supra-amphiphile.…”

“…(b) Illustrations of the formation of vesicles and GSH-controlled DOX release. Reproduced with permission from ref [36]…”

Stimuli-Responsive Amphiphilic Pillar[n]arene Nanovesicles for Targeted Delivery of Cancer Drugs

“…These include acidic pH, high levels of hydrogen peroxide and glutathione (GSH), and overexpressed receptors and proteins, which could be exploited to disrupt the amphiphilic pillar[n] arene nanovesicles and consequent release of their drug loads selectively inside cancer cells without off-target toxic effects on healthy ones. 10 Stimuli-responsive pillar[n]arenes can increase the loading capacity of chemotherapeutic agents, enhance the cytotoxicity and targeting to different cancer cells (rapid release into cancer cells in response to different stimuli) followed by high internalization and endocytosis, and reduce toxicity to normal cells. 6 Therefore, smart drug delivery supramolecular systems can be designed to target the tumor cells where they release their cargo in response to either intracellular stimuli (such as pH variation, overexpression of specific biomolecules, and redox reactions) or external stimuli such as exposure to light.…”

“…The tumor microenvironment has unique features that differ from those of healthy cells. These include acidic pH, high levels of hydrogen peroxide and glutathione (GSH), and overexpressed receptors and proteins, which could be exploited to disrupt the amphiphilic pillar­[ n ] arene nanovesicles and consequent release of their drug loads selectively inside cancer cells without off-target toxic effects on healthy ones …”

Pillar[5]arene-based [1]rotaxanes with salicylaldimine as the stopper: synthesis, characterization and application in the fluorescence turn-on sensing of Zn2+ in water

“…13 Subsequently, extensive studies have been conducted on its synthetic methods, [14][15][16] host-guest molecular recognition motifs, [17][18][19][20] structural transformations, 21 self-assembly properties, [22][23][24][25] and applications. [26][27][28][29][30] In 2011, Stoddart's group fabricated the first pillar [5]arene-based rotaxane (P5R) with 1,8-diaminooctane as the axle that was stoppered with 3,5-di-tert-butylbenzaldehyde. 31 Afterward, P5R compounds have been widely fabricated and studied.…”