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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.

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