Stimulus-Responsive Anti-Oxidizing Drug Crystals and their Ecological Implication

Byoung Soo Kim, Jiayu Leong, Seung Jung Yu, Younghak Cho, Chang Gyun Park, Da Hye Kim, Eunkyung Ko, Sung Gap Im, Jonghwi Lee, Young Jun Kim, Hyunjoon Kong

Research output: Contribution to journalArticlepeer-review


Various antioxidants are being used to neutralize the harmful effects of reactive oxygen species (ROS) overproduced in diseased tissues and contaminated environments. Polymer-directed crystallization of antioxidants has attracted attention as a way to control drug efficacy through molecular dissolution. However, most recrystallized antioxidants undertake continuous dissolution independent of the ROS level, thus causing side-effects. This study demonstrates a unique method to assemble antioxidant crystals that modulate their dissolution rate in response to the ROS level. We hypothesized that antioxidants recrystallized using a ROS-labile polymer would be triggered to dissolve when the ROS level increases. We examined this hypothesis by using catechin as a model antioxidant. Catechin was recrystallized using polyethylenimine cross-linked with ROS-labile diselanediylbis-(ethane-2,1-diyl)-diacrylate. Catechin crystallized with the ROS-labile polymer displays accelerated dissolution proportional to the H2O2 concentration. The ROS-responsive catechin crystals protect vascular cells from oxidative insults by activating intracellular glutathione peroxidase expression and, in turn, inhibiting an increase in the intracellular oxidative stress. In addition, ROS-responsive catechin crystals alleviate changes in the heart rate of Daphnia magna in oxidative media. We propose that the results of this study would be broadly useful for improving the therapeutic efficacy of a broad array of drug compounds.

Original languageEnglish (US)
Article number1900765
Issue number21
StatePublished - May 24 2019


  • Daphnia
  • cardioprotective effect
  • catechin
  • drug crystallization
  • oxidative stress

ASJC Scopus subject areas

  • Biotechnology
  • Biomaterials
  • Chemistry(all)
  • Materials Science(all)


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