Maytansinoids are a successful class of natural and semisynthetic tubulin binders, known for their potent cytotoxic activity. Their wider application as cytotoxins and chemical probes to study tubulin dynamics has been held back by the complexity of natural product chemistry. Here we report the synthesis of long-chain derivatives and maytansinoid conjugates. We confirmed that bulky substituents do not impact their high activity or the scaffold's binding mode. These encouraging results open new avenues for the design of new maytansine-based probes.

Maytansinol Functionalization: Towards Useful Probes for Studying Microtubule Dynamics / Z. Boiarska, H. Pérez-Peña, A. Abel, P. Marzullo, B. Álvarez-Bernad, F. Bonato, B. Santini, D. Horvath, D. Lucena-Agell, F. Vasile, M. Sironi, J.F. Díaz, A.E. Prota, S. Pieraccini, D. Passarella. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 29:5(2023 Jan 24), pp. 1-12. [10.1002/chem.202203431]

Maytansinol Functionalization: Towards Useful Probes for Studying Microtubule Dynamics

Z. Boiarska
Co-primo
;
A. Abel
Co-primo
;
P. Marzullo
Co-primo
;
F. Bonato;B. Santini;F. Vasile;M. Sironi;S. Pieraccini
;
D. Passarella
2023

Abstract

Maytansinoids are a successful class of natural and semisynthetic tubulin binders, known for their potent cytotoxic activity. Their wider application as cytotoxins and chemical probes to study tubulin dynamics has been held back by the complexity of natural product chemistry. Here we report the synthesis of long-chain derivatives and maytansinoid conjugates. We confirmed that bulky substituents do not impact their high activity or the scaffold's binding mode. These encouraging results open new avenues for the design of new maytansine-based probes.
chemical probes; maytansinoids; maytansinol functionalization; microtubules; tubulin
Settore CHIM/06 - Chimica Organica
24-gen-2023
5-dic-2022
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/952967
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