Issue 38, 2011
From the journal:

Chemical Communications

A novel pathway for maytansinoid release from thioether linked antibody–drug conjugates (ADCs) under oxidative conditions†

Nathan Fishkin,*a   Erin K. Maloney,a   Ravi V. J. Charia  and  Rajeeva Singha  

* Corresponding authors

a ImmunoGen, Inc., 830 Winter Street, Waltham, MA, USA
E-mail: nfishkin@immunogen.com
Tel: +1 781-895-0747

Abstract

A novel pathway for ex vivo maytansinoid release from thioether linked antibody maytansinoid conjugates (AMCs) upon incubation in human plasma has been identified. A thioether succinimide-linked AMC can undergo chemical oxidation followed by sulfoxide elimination under mild aqueous conditions (pH 5.5–7.5, 37 °C). Oxidized thioether-linked AMCs exhibit high, target-specific cytotoxicity toward cancer cells.

Graphical abstract: A novel pathway for maytansinoid release from thioether linked antibody–drug conjugates (ADCs) under oxidative conditions

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Article information

DOI
https://doi.org/10.1039/C1CC14164C
Article type
Communication
Submitted
11 Jul 2011
Accepted
10 Aug 2011
First published
26 Aug 2011

Chem. Commun., 2011,47, 10752-10754

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A novel pathway for maytansinoid release from thioether linked antibody–drug conjugates (ADCs) under oxidative conditions

N. Fishkin, E. K. Maloney, R. V. J. Chari and R. Singh, Chem. Commun., 2011, 47, 10752 DOI: 10.1039/C1CC14164C

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