@article{son_wu_dou_fujita_cao_liu_lindsey_2023, title={Article Tethered Indoxyl-Glucuronides for Enzymatically Triggered Cross-Linking}, volume={28}, ISSN={["1420-3049"]}, DOI={10.3390/molecules28104143}, abstractNote={Indoxyl-glucuronides, upon treatment with β-glucuronidase under physiological conditions, are well known to afford the corresponding indigoid dye via oxidative dimerization. Here, seven indoxyl-glucuronide target compounds have been prepared along with 22 intermediates. Of the target compounds, four contain a conjugatable handle (azido-PEG, hydroxy-PEG, or BCN) attached to the indoxyl moiety, while three are isomers that include a PEG-ethynyl group at the 5-, 6-, or 7-position. All seven target compounds have been examined in indigoid-forming reactions upon treatment with β-glucuronidase from two different sources and rat liver tritosomes. Taken together, the results suggest the utility of tethered indoxyl-glucuronides for use in bioconjugation chemistry with a chromogenic readout under physiological conditions.}, number={10}, journal={MOLECULES}, author={Son, Juno and Wu, Zhiyuan and Dou, Jinghuai and Fujita, Hikaru and Cao, Phuong-Lien Doan and Liu, Qihui and Lindsey, Jonathan S.}, year={2023}, month={May} }
 @article{sato_wu_dou_son_lindsey_2023, title={Indoxyl-glucosides bearing tethers for enzymatically triggered cross-linking}, volume={47}, ISSN={["1369-9261"]}, DOI={10.1039/d2nj06267d}, abstractNote={Tethered indoxyl-glucosides upon treatment with β-glucosidase under physiological conditions afford the corresponding indigoid dye via oxidative dimerization.}, number={17}, journal={NEW JOURNAL OF CHEMISTRY}, author={Sato, Daisuke and Wu, Zhiyuan and Dou, Jinghuai and Son, Juno and Lindsey, Jonathan S. S.}, year={2023}, month={May}, pages={8223–8242} }
 @article{wu_dou_nguyen_eppley_siwawannapong_zhang_lindsey_2022, title={Tailoring the AIE Chromogen 2-(2-Hydroxyphenyl)benzothiazole for Use in Enzyme-Triggered Molecular Brachytherapy}, volume={27}, ISSN={["1420-3049"]}, DOI={10.3390/molecules27248682}, abstractNote={A targeted strategy for treating cancer is antibody-directed enzyme prodrug therapy, where the enzyme attached to the antibody causes conversion of an inactive small-molecule prodrug into an active drug. A limitation may be the diffusion of the active drug away from the antibody target site. A related strategy with radiotherapeutics entails enzymatically promoted conversion of a soluble to insoluble radiotherapeutic agent, thereby immobilizing the latter at the target site. Such a molecular brachytherapy has been scarcely investigated. In distinct research, the advent of molecular designs for aggregation-induced emission (AIE) suggests translational use in molecular brachytherapy. Here, several 2-(2-hydroxyphenyl)benzothiazole substrates that readily aggregate in aqueous solution (and afford AIE) were elaborated in this regard. In particular, (1) the 2-(2-hydroxyphenyl) unit was derivatized to bear a pegylated phosphodiester that imparts water solubility yet undergoes enzymatic cleavage, and (2) a p-phenol unit was attached to the benzo moiety to provide a reactive site for final-step iodination (here examined with natural abundance iodide). The pegylated phosphodiester-iodinated benzothiazole undergoes conversion from aqueous-soluble to aqueous-insoluble upon treatment with a phosphatase or phosphodiesterase. The aggregation is essential to molecular brachytherapy, whereas the induced emission of AIE is not essential but provides a convenient basis for research development. Altogether, 21 compounds were synthesized (18 new, 3 known via new routes). Taken together, blending biomedical strategies of enzyme prodrug therapy with materials chemistry concerning substances that undergo AIE may comprise a step forward on the long road toward molecular brachytherapy.}, number={24}, journal={MOLECULES}, author={Wu, Zhiyuan and Dou, Jinghuai and Nguyen, Kathy-Uyen and Eppley, Jayden C. and Siwawannapong, Kittipan and Zhang, Yunlong and Lindsey, Jonathan S.}, year={2022}, month={Dec} }
 @article{fujita_dou_matsumoto_wu_lindsey_2020, title={Enzymatically triggered chromogenic cross-linking agents under physiological conditions}, volume={44}, ISSN={["1369-9261"]}, DOI={10.1039/c9nj04126e}, abstractNote={Oxidative dimerization of an indoxyl moiety, released by glycosidase action in aqueous solution, yields an indigoid dye in formats that enable bioconjugation and molecular cross-linking.}, number={3}, journal={NEW JOURNAL OF CHEMISTRY}, author={Fujita, Hikaru and Dou, Jinghuai and Matsumoto, Nobuyuki and Wu, Zhiyuan and Lindsey, Jonathan S.}, year={2020}, month={Jan}, pages={719–743} }