A self-immolative linker that releases thiols detects penicillin amidase and nitroreductase with high sensitivity via absorption spectroscopy

Eli M. Espinoza; Joachim J. Røise; Maomao He; I-Che Li; Alvin K. Agatep; Patrick Udenyi; Hesong Han; Nicole Jackson; D. Lucas Kerr; Dake Chen; Michael R. Stentzel; Emily Ruan; Lee Riley; Niren Murthy

doi:10.1039/D1CC05322A

A self-immolative linker that releases thiols detects penicillin amidase and nitroreductase with high sensitivity via absorption spectroscopy†

Eli M. Espinoza,

^a Joachim J. Røise,

^ab Maomao He,^a I-Che Li,^a Alvin K. Agatep,^a Patrick Udenyi,^b Hesong Han,^a Nicole Jackson,^c D. Lucas Kerr,

^b Dake Chen,^a Michael R. Stentzel,^a Emily Ruan,^b Lee Riley*^c and Niren Murthy

*^ad

Author affiliations

* Corresponding authors

^a Department of Bioengineering, University of California, Berkeley, Berkeley, CA 94720, USA
E-mail: nmurthy@berkeley.edu

^b Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720, USA

^c School of Public Health, Division of Infectious Diseases and Vaccinology, University of California Berkeley, Berkeley, CA, USA
E-mail: lwriley@berkeley.edu

^d Innovative Genomics Institute (IGI), 2151 Berkeley Way, Berkeley, CA, USA

Abstract

This article reports the synthesis and characterization of a novel self-immolative linker, based on thiocarbonates, which releases a free thiol upon activation via enzymes. We demonstrate that thiocarbonate self-immolative linkers can be used to detect the enzymes penicillin G amidase (PGA) and nitroreductase (NTR) with high sensitivity using absorption spectroscopy. Paired with modern thiol amplification technology, the detection of PGA and NTR were achieved at concentrations of 160 nM and 52 nM respectively. In addition, the PGA probe was shown to be compatible with both biological thiols and enzymes present in cell lysates.

Chemical Communications

A self-immolative linker that releases thiols detects penicillin amidase and nitroreductase with high sensitivity via absorption spectroscopy†

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A self-immolative linker that releases thiols detects penicillin amidase and nitroreductase with high sensitivity via absorption spectroscopy

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