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Synthesis of a Reactive Oxygen Species-Responsive Doxorubicin Derivative.

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⁺/H?O?) resulting in successful and rapid thioacetal oxidative cleavage, which was monitored using ¹H NMR.

SUBMITTER: Delehanty JB

PROVIDER: S-EPMC6100310 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Synthesis of a Reactive Oxygen Species-Responsive Doxorubicin Derivative.

Delehanty James B JB Das Shivani S Goldberg Efram E Sangtani Ajmeeta A Knight D Andrew DA

Molecules (Basel, Switzerland) 20180721 7

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 thioacet ...[more]

PMID: 30037071

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