Spiropyran-based nanocarrier: a new Zn²⁺-responsive delivery system with real-time intracellular sensing capabilities

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dc.contributor.authorHeng, S.
dc.contributor.authorZhang, X.
dc.contributor.authorPei, J.
dc.contributor.authorAdwal, A.
dc.contributor.authorReineck, P.
dc.contributor.authorGibson, B.C.
dc.contributor.authorHutchinson, M.R.
dc.contributor.authorAbell, A.D.
dc.date.issued2019
dc.description.abstractA new spiropyran-based stimuli-responsive delivery system is fabricated. It 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, the use of the nanocarriers to deliver a caspase inhibitor, Azure B, into apoptotic cells in response to an elevated Zn²⁺ concentration is demonstrated. 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.
dc.description.statementofresponsibilitySabrina Heng, Xiaozhou Zhang, Jinxin Pei, Alaknanda Adwal, Philipp Reineck, Brant C. Gibson, Mark R. Hutchinson and Andrew D. Abell
dc.identifier.citationChemistry - A European Journal, 2019; 25(3):854-862
dc.identifier.doi10.1002/chem.201804816
dc.identifier.issn0947-6539
dc.identifier.issn1521-3765
dc.identifier.orcidPei, J. [0000-0003-2453-929X]
dc.identifier.orcidAdwal, A. [0000-0001-9441-5407]
dc.identifier.orcidHutchinson, M.R. [0000-0003-2154-5950]
dc.identifier.orcidAbell, A.D. [0000-0002-0604-2629]
dc.identifier.urihttp://hdl.handle.net/2440/117844
dc.language.isoen
dc.publisherWiley
dc.relation.granthttp://purl.org/au-research/grants/arc/CE140100003
dc.rights© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
dc.source.urihttps://doi.org/10.1002/chem.201804816
dc.subjectApoptosis; fluorescence; metal ions; payload delivery; spiropyran-based nanocarrier
dc.titleSpiropyran-based nanocarrier: a new Zn²⁺-responsive delivery system with real-time intracellular sensing capabilities
dc.title.alternativeSpiropyran-based nanocarrier: a new Zn2+ -responsive delivery system with real-time intracellular sensing capabilities
dc.typeJournal article
pubs.publication-statusPublished

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