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Hierarchical Self‐Assembly of BODIPY Dyes as a Tool to Improve the Antitumor Activity of Capsaicin in Prostate Cancer
Author(s) -
Sampedro Angel,
RamosTorres Ágata,
Schwöppe Christian,
MückLichtenfeld Christian,
Helmers Ingo,
Bort Alicia,
DíazLaviada Inés,
Fernández Gustavo
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201804783
Subject(s) - capsaicin , prostate cancer , prostate , bodipy , cancer , medicine , cancer research , receptor , fluorescence , physics , quantum mechanics
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.