4.6 Article

Tethered Indoxyl-Glucuronides for Enzymatically Triggered Cross-Linking

Journal

MOLECULES
Volume 28, Issue 10, Pages -

Publisher

MDPI
DOI: 10.3390/molecules28104143

Keywords

chromogenic; dimerization; beta-glucuronidase; indigoid; indole; oxidation

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In this study, seven target compounds and 22 intermediates were synthesized, and their corresponding indigo dyes were obtained through treatment with β-glucuronidase under physiological conditions. The results indicate that these tethered indoxyl-glucuronides can be used for bioconjugation chemistry with a visible chromogenic readout under physiological conditions.
Indoxyl-glucuronides, upon treatment with beta-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 beta-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.

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