A photo-responsive fluorescent amphiphile for target-specific and image-guided drug delivery applications

Multifunctional drug delivery systems are the centerpiece of effective chemotherapeutic strategies. Herein, we report the synthesis of an acetazolamide-linked cyanine-3-based NIR-responsive fluorescent macrocyclic amphiphile that self-assembled into spherical nanostructures in the aqueous medium via...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-10, Vol.2 (39), p.783-7813
Main Authors: Dey, Subhasis, Sen, Plaboni, Patel, Anjali, Prusty, Biswa Mohan, Ghosh, Siddhartha Sankar, Manna, Debasis
Format: Article
Language:English
Subjects:
Acetazolamide
Antitumor agents
Aqueous solutions
Cytotoxicity
Doxorubicin
Drug delivery
Drug delivery systems
Fluorescence
Lipids
Self-assembly
System effectiveness
Toxicity
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Summary:Multifunctional drug delivery systems are the centerpiece of effective chemotherapeutic strategies. Herein, we report the synthesis of an acetazolamide-linked cyanine-3-based NIR-responsive fluorescent macrocyclic amphiphile that self-assembled into spherical nanostructures in the aqueous medium via a J-aggregation pattern. The amphiphile shows various favorable properties of lipids. The photocleavage of the strained dioxacycloundecine ring induces spherical to nanotubular self-assembly with concomitant release of an encapsulated anticancer drug, doxorubicin (Dox), in a controlled manner. The CA-IX targeted amphiphile also showed lower cytotoxicity, effective cellular uptake, and Dox delivery to the model carcinoma cells. CYsome: an acetazolamide grafted cyanine-3-based macrocyclic amphiphile demonstrates target-specificity, biocompatibility, self-imaging, and a NIR-responsive release profile for image-guided chemotherapeutic applications.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob01332k