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Molecules 2018, 23(7), 1809; https://doi.org/10.3390/molecules23071809

Synthesis of a Reactive Oxygen Species-Responsive Doxorubicin Derivative

1
Center for Bio/Molecular Science and Engineering, Code 6900, Naval Research Laboratory, Washington, DC 20375, USA
2
Chemistry Department, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USA
*
Author to whom correspondence should be addressed.
Received: 28 May 2018 / Revised: 16 July 2018 / Accepted: 18 July 2018 / Published: 21 July 2018
(This article belongs to the Section Medicinal Chemistry)
Full-Text   |   PDF [1104 KB, uploaded 21 July 2018]   |  

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 N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (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. View Full-Text
Keywords: doxorubicin; heterobifunctional; linker doxorubicin; heterobifunctional; linker
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Delehanty, J.B.; Das, S.; Goldberg, E.; Sangtani, A.; Knight, D.A. Synthesis of a Reactive Oxygen Species-Responsive Doxorubicin Derivative. Molecules 2018, 23, 1809.

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