Preprint Article Version 1 This version is not peer-reviewed

Synthesis of a Reactive Oxygen Species-Responsive Doxorubicin Derivative

Version 1 : Received: 28 May 2018 / Approved: 29 May 2018 / Online: 29 May 2018 (08:54:56 CEST)

How to cite: Delehanty, J.B.; Das, S.; Goldberg, E.; Sangtani, A.; Knight, D.A. Synthesis of a Reactive Oxygen Species-Responsive Doxorubicin Derivative. Preprints 2018, 2018050419 (doi: 10.20944/preprints201805.0419.v1). Delehanty, J.B.; Das, S.; Goldberg, E.; Sangtani, A.; Knight, D.A. Synthesis of a Reactive Oxygen Species-Responsive Doxorubicin Derivative. Preprints 2018, 2018050419 (doi: 10.20944/preprints201805.0419.v1).

Abstract

A heterobifunctional reactive oxygen species (ROS)-responsive linker for directed drug assembly onto and delivery from a quantum dot (QD) nanoparticle carrier was synthesized and coupled to doxorubicin using EDC/sulfo-NHS coupling. The doxorubicin conjugate was characterized using 1H NMR and LC-MS and subsequently reacted under conditions of ROS formation (Cu2+/H2O2) resulting in successful and rapid thioacetal oxidative cleavage which was monitored using 1H NMR. The deprotected amine linker is amenable to peptide or protein conjugation prior to QD assembly or to direct conjugation to cognate reactive groups on ligands that cap the QD surface.

Subject Areas

doxorubicin; heterobifunctional; linker

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