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Differential Interactions of Chiral Nanocapsules with DNA

The Institute for Drug Research, The School of Pharmacy, Faculty of Medicine, The Hebrew University of Jerusalem, Jerusalem 9112192, Israel
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2021, 22(2), 584;
Received: 10 December 2020 / Revised: 29 December 2020 / Accepted: 30 December 2020 / Published: 8 January 2021
(This article belongs to the Special Issue Assembly Superstructures in Chemistry)
(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. View Full-Text
Keywords: chiral nanoparticles; chiral polymeric nanocapsules; polyurea; stereospecific interactions; DNA binding chiral nanoparticles; chiral polymeric nanocapsules; polyurea; stereospecific interactions; DNA binding
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MDPI and ACS Style

Zoabi, A.; Margulis, K. Differential Interactions of Chiral Nanocapsules with DNA. Int. J. Mol. Sci. 2021, 22, 584.

AMA Style

Zoabi A, Margulis K. Differential Interactions of Chiral Nanocapsules with DNA. International Journal of Molecular Sciences. 2021; 22(2):584.

Chicago/Turabian Style

Zoabi, Amani; Margulis, Katherine. 2021. "Differential Interactions of Chiral Nanocapsules with DNA" Int. J. Mol. Sci. 22, no. 2: 584.

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