Reversing the undesirable pH-profile of doxorubicin via activation of a di-substituted maleamic acid prodrug at tumor acidity

Anqi Zhang; Lan Yao; Ming An

doi:10.1039/C7CC06843C

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Reversing the undesirable pH-profile of doxorubicin via activation of a di-substituted maleamic acid prodrug at tumor acidity†

Anqi Zhang,

^a Lan Yao

^b and Ming An

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, State University of New York (SUNY), Binghamton University, P.O. Box 6000, Binghamton, New York 13902, USA
E-mail: aming@binghamton.edu
Tel: +1 (607) 777 3224

^b Department of Physics, Applied Physics and Astronomy, SUNY, Binghamton University, P.O. Box 6000, Binghamton, New York 13902, USA

Abstract

The acid-labile behavior of di-substituted maleamic acid (DMA) and its equilibrium with di-substituted maleimide (DMI) are exploited to build an ultra acid-sensitive, small molecule prodrug that can be activated by tumor extracellular pH (pHe) in the range of 6.5–6.9. Such a DMA prodrug reversed the unfavorable pH-profile of doxorubicin (Dox), which may improve its therapeutic window.

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Article information

DOI: https://doi.org/10.1039/C7CC06843C
Article type: Communication
Submitted: 01 Sep 2017
Accepted: 31 Oct 2017
First published: 01 Nov 2017

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Chem. Commun., 2017,53, 12826-12829

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Reversing the undesirable pH-profile of doxorubicin via activation of a di-substituted maleamic acid prodrug at tumor acidity

A. Zhang, L. Yao and M. An, Chem. Commun., 2017, 53, 12826 DOI: 10.1039/C7CC06843C

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Chemical Communications

Reversing the undesirable pH-profile of doxorubicin via activation of a di-substituted maleamic acid prodrug at tumor acidity†

Abstract

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Reversing the undesirable pH-profile of doxorubicin via activation of a di-substituted maleamic acid prodrug at tumor acidity

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