Issue 36, 2019

Synthesis and application of light-switchable arylazopyrazole rapamycin analogs

Abstract

Rapamycin-induced dimerization of FKBP and FRB has been utilized as a tool for co-localizing two proteins of interest in numerous applications. Due to the tight binding interaction of rapamycin with FKBP and FRB, the ternary complex formation is essentially irreversible. Since biological processes occur in a highly dynamic fashion with cycles of protein association and dissociation to generate a cellular response, it is useful to have chemical tools that function in a similar manner. We have developed arylazopyrazole-modified rapamycin analogs which undergo a configurational change upon light exposure and we observed enhanced ternary complex formation for the cis-isomer over the trans-isomer for one of the analogs.

Graphical abstract: Synthesis and application of light-switchable arylazopyrazole rapamycin analogs

Supplementary files

Article information

Article type
Communication
Submitted
04 Aug 2019
Accepted
27 Aug 2019
First published
30 Aug 2019

Org. Biomol. Chem., 2019,17, 8348-8353

Author version available

Synthesis and application of light-switchable arylazopyrazole rapamycin analogs

T. M. Courtney, T. J. Horst, C. P. Hankinson and A. Deiters, Org. Biomol. Chem., 2019, 17, 8348 DOI: 10.1039/C9OB01719D

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