Boronic acid liposomes for cellular delivery and content release driven by carbohydrate binding

Abstract

Boronic acid liposomes enable triggered content release and cell delivery driven by carbohydrate binding. Dye release assays using hydrophilic and hydrophobic fluorophores validate dose-dependent release upon carbohydrate treatment. Microscopy results indicate dramatic enhancements in cell delivery, showcasing the prospects of boronic acid lipids for drug delivery.

The challenges of glycan recognition with natural and artificial receptors

“…Liposomes bearing boronic acids on their outer surface showed cell-binding ability, providing a tool for drug delivery upon binding with the glycans on the cell surface. 120,121 Further studies could lead to the development of probes with applications in targeted drug delivery, cell labelling and selective imaging.…”

Improving cellular uptake of therapeutic entities through interaction with components of cell membrane

“…(B) Fluorescence image of cells treated with boronic acid modified liposomes. Reproduced with permission from ref (Zhang et al., 2018). Copyright Royal Society of Chemistry.…”

“…Zhang et al. reported boronic acid decorated liposomes as a means for enhancing both cell infiltration and content delivery based on saccharides binding interactions (Figure 3) (Zhang et al., 2018). PBA modified liposome showed dramatic enhancement of delivery efficiency compared with control liposomes, which suggested that boronic acid is effective for driving liposomal cell entry.…”

Lipid Switches: Stimuli‐Responsive Liposomes through Conformational Isomerism Driven by Molecular Recognition

“…Instead, we relied upon multivalent carbohydrate binding to cause the convergence of lipids within the membrane to disturb packing and trigger release. Toward this end, two boronic acid lipids, represented here by structure 7 , were designed, synthesized, and studied (Scheme ) . Upon titration of liposomes containing 7 with the model carbohydrate heparin, both the hydrophobic dye Nile red and hydrophilic dye sulforhodamine B were released.…”

“…To wardt his end, two boronic acid lipids, represented here by structure 7,w ered esigned, synthesized, and studied (Scheme 8). [29] Upon titrationo fl iposomes containing 7 with the model carbohydrate heparin, both the hydrophobic dye Nile red and hydrophilic dye sulforhodamine Bw ere released. In addition, DLS studies once again showed large size increases upon carbohydrate addition, and TEM images showed liposome perturbation.F inally,f luorescencec ellular microscopy studies indicated dramatically enhanced delivery of fluorescence-labeled liposomes to cells when incorporating 10 %o f boronic acid lipid 7.A ss uch, boronic acid liposomes show strongp otentialf or delivering contents to cells and for triggered release driven by carbohydrate binding.…”