Hierarchical Self‐Assembly of BODIPY Dyes as a Tool to Improve the Antitumor Activity of Capsaicin in Prostate Cancer

Capsaicin (CAP) has been long known for its analgesic properties and more recently for its antitumor activity in various cell types. However, its pungency and the high doses needed to achieve a significant activity have precluded its application in cancer therapy. Herein, we propose a straightforwar...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-12, Vol.57 (52), p.17235-17239
Main Authors: Sampedro, Angel, Ramos‐Torres, Ágata, Schwöppe, Christian, Mück‐Lichtenfeld, Christian, Helmers, Ingo, Bort, Alicia, Díaz‐Laviada, Inés, Fernández, Gustavo
Format: Article
Language:English
Subjects:
Agglomeration
amphiphilic Systems
Analgesics
Anticancer properties
Antitumor activity
aqueous self-assembly
Aqueous solutions
BODIPY dyes
Cancer
Capsaicin
Dismantling
Dyes
Fluorescence
fluorescent probes
Prostate cancer
Pungent principles
Tumors
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Summary:Capsaicin (CAP) has been long known for its analgesic properties and more recently for its antitumor activity in various cell types. However, its pungency and the high doses needed to achieve a significant activity have precluded its application in cancer therapy. Herein, we propose a straightforward novel strategy to improve the antitumor effect of CAP based on the enhancement of its aggregation propensity in aqueous media by covalent attachment of a BODIPY (BDP) dye. The target CAP‐BDP 1 self‐assembles in aqueous solutions into weakly fluorescent globular assemblies that become highly emissive upon cell uptake‐induced disassembly. Remarkably, due to the improved delivery to the tumour tissue upon aggregation, we have succeeded in reducing the doses of CAP‐based drugs in vivo in prostate cancer by two orders of magnitude while maintaining a substantial antitumor activity. Spice up your life! Covalent attachment of a fluorescent BODIPY dye has been exploited to enhance the aggregation propensity of capsaicin—the major active component of chili peppers—in aqueous media. Due to the improved delivery of active capsaicin‐based molecules to the tumour tissue upon aggregation, the effective doses for prostate cancer treatment could be successfully reduced by two orders of magnitude.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201804783