Spiropyran‐based Nanocarrier: A New Zn2+‐Responsive Delivery System with Real Time Intracellular Sensing Capabilities

Heng, S, Zhang, X, Pei, J, Alaknanda, A, Reineck, P, Gibson, B, Hutchinson, M and Abell, A 2018, 'Spiropyran‐based Nanocarrier: A New Zn2+‐Responsive Delivery System with Real Time Intracellular Sensing Capabilities', Chemistry: A European Journal, vol. 25, no. 3, pp. 854-862.


Document type: Journal Article
Collection: Journal Articles

Title Spiropyran‐based Nanocarrier: A New Zn2+‐Responsive Delivery System with Real Time Intracellular Sensing Capabilities
Author(s) Heng, S
Zhang, X
Pei, J
Alaknanda, A
Reineck, P
Gibson, B
Hutchinson, M
Abell, A
Year 2018
Journal name Chemistry: A European Journal
Volume number 25
Issue number 3
Start page 854
End page 862
Total pages 9
Publisher Wiley - V C H Verlag GmbH & Co. KGaA
Abstract A new spiropyran-based stimuli-responsive delivery system is presented that encapsulates and then releases an extraneous compound in response to elevated levels of Zn2+, a critical factor in cell apoptosis. A C12-alkyl substituent on the spiropyran promotes self- assembly into a micelle-like nanocarrier in aqueous media, with nanoprecipitation and encapsulation of added payload. Zn2+ binding occurs to an appended bis(2-pyridylmethyl)amine group at biologically relevant micromolar concentration. This leads to switching of the spiropyran (SP) isomer to the strongly fluorescent ring opened merocyanine-Zn2+ (MC-Zn2+) complex, with associated expansion of the nanocarriers to release the encapsulated payload. Payload release is demonstrated in solution and in HEK293 cells by encapsulation of a blue fluorophore, 7-hydroxycoumarin, and monitoring its release using fluorescence spectroscopy and microscopy. Furthermore, we demonstrate the use of the nanocarriers to deliver a caspase inhibitor, Azure B, into apoptotic cells in response to an elevated Zn2+ concentration. This then inhibits intracellular caspase activity, as evidenced by confocal microscopy and in real-time by time-lapsed microscopy. Finally, the nanocarriers are shown to release an encapsulated proteasome inhibitor (5) in Zn2+-treated breast carcinoma cell line models. This then inhibits intracellular proteasome and induces cytotoxicity to the carcinoma cells.
Subject Nanochemistry and Supramolecular Chemistry
Physical Chemistry of Materials
Nanomaterials
Keyword(s) apoptosis
fluorescence
metal ions
payload delivery
spiropyran-based nanocarrier
DOI - identifier 10.1002/chem.201804816
Copyright notice © 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN 1521-3765
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