Journal
JOURNAL OF PHARMACEUTICAL SCIENCES
Volume 105, Issue 12, Pages 3615-3625Publisher
WILEY-BLACKWELL
DOI: 10.1016/j.xphs.2016.09.008
Keywords
pillar[n]arene; drug delivery; fluorescence; biodiagnostics; host-guest; nanocapsule; molecular modeling; excipient; pharmaceutics
Funding
- Commonwealth Government of Australia
- University of Sydney
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Pillar[n]arenes are a new family of nanocapsules that have shown application in a number of areas, but because of their poor water solubility their biomedical applications are limited. Recently, a method of synthesizing water-soluble pillar[n]arenes was developed. In this study, carboxylated pillar[n]arenes (WP [n], n = 6 or 7) have been examined for their ability to form host-guest complexes with compounds relevant to drug delivery and biodiagnostic applications. Both pillar[n]arenes form host-guest complexes with memantine, chlorhexidine hydrochloride, and proflavine by H-1 nuclear magnetic resonance and modeling. Binding is stabilized by hydrophobic effects within the cavities, and hydrogen bonding and electrostatic interactions at the portals. Encapsulation within WP[6] results in the complete and efficient quenching of proflavine fluorescence, giving rise to on and off states that have potential in biodiagnostics. The toxicity of the pillar[n] arenes was examined using in vitro growth assays with the OVCAR-3 and HEK293 cell lines. The pillar[n]arenes are relatively nontoxic to cells except at high doses and after prolonged continuous exposure. Overall, the results show that there could be a potentially large range of medical applications for carboxylated pillar[n]arene nanocapsules. (C) 2016 American Pharmacists Association (R). Published by Elsevier Inc. All rights reserved.
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