Self-assembling Releasable Thiocolchicine–Diphenylbutenylaniline Conjugates

The design and the synthesis of new self-assembling conjugates is reported. The target compounds are characterized by the presence of a self-immolative linker that secures a controlled release induced by lipase cleavage. 4-(1,2-Diphenylbut-1-en-1-yl)­aniline is used as a self-assembling inducer and...

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Published in:ACS medicinal chemistry letters 2019-04, Vol.10 (4), p.611-614
Main Authors: Fumagalli, Gaia, Polito, Laura, Colombo, Eleonora, Foschi, Francesca, Christodoulou, Michael S, Galeotti, Francesco, Perdicchia, Dario, Bassanini, Ivan, Riva, Sergio, Seneci, Pierfausto, García-Argáez, Aída, Dalla Via, Lisa, Passarella, Daniele
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Language:English
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Letter
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Summary:The design and the synthesis of new self-assembling conjugates is reported. The target compounds are characterized by the presence of a self-immolative linker that secures a controlled release induced by lipase cleavage. 4-(1,2-Diphenylbut-1-en-1-yl)­aniline is used as a self-assembling inducer and amino-thiocolchicine as prototype of drug. The release of thiocolchicine derivative has been demonstrated in vitro in the presence of porcine pancreatic lipase and Celite-supported lipase. The formation of nanoparticles is confirmed by dynamic light scattering, atomic force microscopy, and fluorescence microscopy. The antiproliferative activity has been proved on two human cancer cell lines.
ISSN:1948-5875
1948-5875
DOI:10.1021/acsmedchemlett.8b00605