Engineered Metal-Phenolic Capsules Show Tunable Targeted Delivery to Cancer Cells

Abstract

We engineered metal-phenolic capsules with both high targeting and low nonspecific cell binding properties. The capsules were prepared by coating phenolic-functionalized hyaluronic acid (HA) and poly(ethylene glycol) (PEG) on calcium carbonate templates, followed by cross-linking the phenolic groups with metal ions and removing the templates. The incorporation of HA significantly enhanced binding and association with a CD44 overexpressing (CD44+) cancer cell line, while the incorporation of PEG reduced nonspecific interactions with a CD44 minimal-expressing (CD44-) cell line. Moreover, high specific targeting to CD44+ cells can be balanced with low nonspecific binding to CD44- cells simply by using an optimized feed-ratio of HA and PEG to vary the content of HA and PEG incorporated into the capsules. Loading an anticancer drug (i.e., doxorubicin) into the obtained capsules resulted in significantly higher cytotoxicity to CD44+ cells but lower cytotoxicity to CD44- cells.

Stimuli‐Responsive Tannin–FeIII Hybrid Microcapsules Demonstrated by the Active Release of an Anti‐Tuberculosis Agent

“…[13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29] With respect to administration, especially to the human body,i deally such capsules should be fabricated based on ab iocompatibleb iodegradablep olymer consisting of an amphiphilic backbonet hat gives the possibility to bind equally efficiently to the hydrophobic core and cover it but also to have ah igh affinity to water. [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29] With respect to administration, especially to the human body,i deally such capsules should be fabricated based on ab iocompatibleb iodegradablep olymer consisting of an amphiphilic backbonet hat gives the possibility to bind equally efficiently to the hydrophobic core and cover it but also to have ah igh affinity to water.…”

“…Polyphenol microparticulate systems, including both microspheres and microcapsules, have been widely studied in recent years as active vectors with the principle goalo ft he delivery of active substances for achieving controlled release rates of the ingredients and/or targeting effects. [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29] With respect to administration, especially to the human body,i deally such capsules should be fabricated based on ab iocompatibleb iodegradablep olymer consisting of an amphiphilic backbonet hat gives the possibility to bind equally efficiently to the hydrophobic core and cover it but also to have ah igh affinity to water. [42,43] The active releasek inetics should ideally be constant.…”

“…Severalg roups have worked on this topic in the recent past, suggesting an oteworthy variety of the systems ford rug protection and/or transport based on tannins. [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] Crestini et al showedt hat the amphiphilic backbone of tannins, consisting of phenolic, catecholic, and pyrogallolic groups that are prone to stacking was ap rerequisite for the preparation of an ew family of tannin capsules generatedw ithout the use of as olid core template. [30] It wasd emonstrated that sonication of oil in water emulsions of different families of tannins are able to generate micro-and nanocapsules with varying degrees of stability.M ore specifically,o ligomeric condensed tannins were found to be able to form stable nanocapsules.U nfortunately, monomeric tannins such as epigallocatechin gallate (EGCG) or tannic acid( TA)g enerate unstablen anoemulsions and do not support the formation of stable micro-and nanocapsule preparations.…”

Phenolic Building Blocks for the Assembly of Functional Materials

“…[75] The choice of phenolic ligand (small or multidentate ligands) used for deposition strongly influences the final disassembly kinetics of MPN films. [75] Additionally, hybrid synthetic analogs including PEG-DOPA polymers, [76] HA-DOPA polymers, [77] or TA modified with peptides [78] can be used to form MPNs, thereby allowing for new functionalities and applications to be realized.…”

“…Reproduced with permission. [77] Copyright 2016 American Chemical Society. (e) Single-cell encapsulation and artificial sporulation.…”