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A Host–Guest Supramolecular Complex with Photoregulated Delivery of Nitric Oxide and Fluorescence Imaging Capacity in Cancer Cells
Author(s) -
Kandoth Noufal,
Malanga Milo,
Fraix Aurore,
Jicsinszky László,
Fenyvesi Éva,
Parisi Tiziana,
Colao Ivana,
Sciortino Maria Teresa,
Sortino Salvatore
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201200640
Subject(s) - supramolecular chemistry , fluorescence , chemistry , hela , biocompatibility , biophysics , photochemistry , fluorescence microscope , cancer cell , conjugate , cyclodextrin , nanotechnology , materials science , cancer , cell , biochemistry , biology , molecule , organic chemistry , optics , physics , genetics , mathematical analysis , mathematics
Herein we report the design, preparation, and properties of a supramolecular system based on a tailored nitric oxide (NO) photodonor and a rhodamine‐labeled β‐cyclodextrin conjugate. The combination of spectroscopic and photochemical experiments shows the absence of significant interchromophoric interactions between the host and the guest in the excited states. As a result, the complex is able to release NO under the exclusive control of visible light, as unambiguously demonstrated by direct detection of this transient species through an amperometric technique, and exhibits the typical red fluorescence of the rhodamine appendage. The supramolecular complex effectively internalizes in HeLa cancer cells as proven by fluorescence microscopy, shows a satisfactory biocompatibility in the dark, and induces about 50 % of cell mortality upon irradiation with visible light. The convergence of all these properties in one single complex makes the present host–guest ensemble an appealing candidate for further delevopment of photoactivatable nanoscaled systems addressed to photostimulated NO‐based therapy.