Abstract
Polydiacetylene vesicles of various compositions were assembled using a two-part mixture of 10,12-pentacosadiynoic acid (PCDA) and ethylenedioxy-bis-ethylamine (EDEA)-labeled PCDA in order to control surface charge and stability within a desired pH range. Investigation of the interaction of the vesicles with mammalian cells as a function of surface charge was carried out and identified a clear correlation in cell–vesicle association and corresponding cell death for vesicles with positive surface charge. The binding behavior of the vesicles was found to be tunable by regulating the proportion of anionic PCDA relative to cationic PCDA–EDEA content within vesicles as to control the surface charge as a function of pH. Association of vesicles with cells thus depended on the corresponding charge of the vesicles and cell surface. The prospect of this work may serve as a step toward future vesicle designs to allow triggered uptake of vesicles locally within low pH tumor microenvironments.
Highlights
Several earlier works thoroughly investigated the potential of 10,12-pentacosadiynoic acid (PCDA)as an amphiphilic building block for the fabrication of self-assembled vesicles that reveal a notable visible color-shift offering it as a popular platform for sensor and assay development [1,2,3,4,5,6,7,8,9]
Formation of polydiacetylene vesicles comprised of PCDA–EDEA, PCDA, or mixtures thereof was carried out by sonication of the component monomeric diaceytlene amphiphiles and subsequent self-assembly by overnight incubation at 4 ◦ C followed by UV polymerization to cross-link the diacetylene amphiphiles
The specific link that we identified between composition and pH is that vesicles comprised purely of PCDA were unstable at low pH suffering aggregation but remained stable at even high pH
Summary
Several earlier works thoroughly investigated the potential of 10,12-pentacosadiynoic acid (PCDA). We constructed complex vesicles comprised of a range of mixtures of carboxylic acid terminated (PCDA) and amine terminated (PCDA–EDEA) amphiphiles in order to examine the link between the composition, colloidal stability, and surface charge response to pH. Extending the application of polydiacetylenees to in vivo studies for tumor imaging and drug delivery applications, polyethylene glycol ( PEG2000) modified polydiacetylene vesicles have shown good in vivo stability and delayed phagocytosis with low toxicity even at 100 mg/kg in rodent models [22,23] While such PEGylated polydiacetylene vesicles have been suggested to accumulate passively in tumors, more sophisticated approaches utilizing polydiacetylene nanoparticles functionalized with targeting moieties have shown more specific uptake by cells overexpressing biotin receptors [24].
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