A trifunctional self-immolative spacer enables drug release with two non-sequential enzymatic cleavages

Alberto Dal Corso; Simone Arosio; Noemi Arrighetti; Paola Perego; Laura Belvisi; Luca Pignataro; Cesare Gennari

doi:10.1039/D1CC02895B

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A trifunctional self-immolative spacer enables drug release with two non-sequential enzymatic cleavages†

Alberto Dal Corso,

*^a Simone Arosio,^a Noemi Arrighetti,

^b Paola Perego,

^b Laura Belvisi,

^a Luca Pignataro

^a and Cesare Gennari

*^a

Author affiliations

* Corresponding authors

^a Università degli Studi di Milano, Dipartimento di Chimica, via C. Golgi, 19, Milan, Italy
E-mail: alberto.dalcorso@unimi.it, cesare.gennari@unimi.it

^b Fondazione IRCCS Istituto Nazionale dei Tumori, Molecular Pharmacology Unit, Department of Applied Research and Technological Development, via Amadeo 42, Milan, Italy

Abstract

Cyclative cleavage of an amine-carbamate self-immolative spacer to deliver a hydroxyl cargo was inhibited by spacer derivatisation with a phosphate monoester handle. This trifunctional spacer was installed in a model anticancer prodrug that showed fast drug release only when incubated with both a protease and a phosphatase enzyme.

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Article information

DOI: https://doi.org/10.1039/D1CC02895B
Article type: Communication
Submitted: 01 Jun 2021
Accepted: 05 Jul 2021
First published: 05 Jul 2021

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Chem. Commun., 2021,57, 7778-7781

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A trifunctional self-immolative spacer enables drug release with two non-sequential enzymatic cleavages

A. Dal Corso, S. Arosio, N. Arrighetti, P. Perego, L. Belvisi, L. Pignataro and C. Gennari, Chem. Commun., 2021, 57, 7778 DOI: 10.1039/D1CC02895B

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Chemical Communications

A trifunctional self-immolative spacer enables drug release with two non-sequential enzymatic cleavages†

Abstract

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A trifunctional self-immolative spacer enables drug release with two non-sequential enzymatic cleavages

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