Abstract
(1) Background: Chiral nanoparticular systems have recently emerged as a compelling platform for investigating stereospecific behavior at the nanoscopic level. We describe chiroselective supramolecular interactions that occur between DNA oligonucleotides and chiral polyurea nanocapsules. (2) Methods: We employ interfacial polyaddition reactions between toluene 2,4-diisocyanate and lysine enantiomers that occur in volatile oil-in-water nanoemulsions to synthesize hollow, solvent-free capsules with average sizes of approximately 300 nm and neutral surface potential. (3) Results: The resultant nanocapsules exhibit chiroptical activity and interact differentially with single stranded DNA oligonucleotides despite the lack of surface charge and, thus, the absence of significant electrostatic interactions. Preferential binding of DNA on d-polyurea nanocapsules compared to their l-counterparts is demonstrated by a fourfold increase in capsule size, a 50% higher rise in the absolute value of negative zeta potential (ζ-potential), and a three times lower free DNA concentration after equilibration with the excess of DNA. (4) Conclusions: We infer that the chirality of the novel polymeric nanocapsules affects their supramolecular interactions with DNA, possibly through modification of the surface morphology. These interactions can be exploited when developing carriers for gene therapy and theranostics. The resultant constructs are expected to be highly biocompatible due to their neutral potential and biodegradability of polyurea shells.
Highlights
Chiral nanomaterials have attracted considerable attention in recent years because they provide a powerful platform for exploring how chiral behavior is impacted by other unique properties attributed to nanometric size, and vice versa [1]
L- or D-lysine was introduced to the oil-in-water emulsion system containing toluene 2,4-diisocyanate (TDI) monomers dissolved in n-butyl acetate as the organic phase, and distilled water with dissolved polyvinyl alcohol (PVA, nonionic polymeric surfactant) as the aqueous phase
We report on a formation of chiral hollow polyurea nanocapsules that can be used for drug delivery and theranostics
Summary
Chiral nanomaterials have attracted considerable attention in recent years because they provide a powerful platform for exploring how chiral behavior is impacted by other unique properties attributed to nanometric size, and vice versa [1]. In early 2020, it was reported that the chirality of supraparticles created through a self-limiting assembly of cobalt oxide nanostructures capped with l-, or d-cysteine controls: (a) the binding of the nanoparticles to cell membrane lipids, (b) the internalization of the nanoparticles by cells and (c) their stability in human plasma [4]. Another recent study reported on a chirality-controlled ability of β-glucan nanoparticles to activate macrophages and produce immune enhancing cytokines which, in combination with their high antitumor drug loading, may enhance antitumor activity [5]. Stereospecific induction of cancer cell death through apoptosis [4] or autophagy [7] was reported for chiral nanoparticles in recent years
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