Turn on chemiluminescence-based probes for monitoring tyrosinase activity in conjunction with biological thiols

Omri Shelef; Adam C. Sedgwick; Sabina Pozzi; Ori Green; Ronit Satchi-Fainaro; Doron Shabat; Jonathan L. Sessler

doi:10.1039/d1cc05217a

Turn on chemiluminescence-based probes for monitoring tyrosinase activity in conjunction with biological thiols

Omri Shelef, Adam C. Sedgwick, Sabina Pozzi, Ori Green, Ronit Satchi-Fainaro^*, Doron Shabat, Jonathan L. Sessler

^*Corresponding author for this work

University of Texas at Austin

Research output: Contribution to journal › Article › peer-review

25 Scopus citations

Abstract

We report a chemiluminescent probe (CLPT1) that permits the paired detection of tyrosinase (Tyr) and biological thiols. Tyr only leads to a poor chemiluminescence response, a finding ascribed to the formation of a stableo-benzoquinone intermediate. The addition of glutathione (GSH), or ascorbate to theo-benzoquinone intermediate results in thiol conjugation or reduction to this intermediate, respectively. This produces a strong chemiluminescence response. Thiol co-dependence was demonstrated in live cells using the cell permeable analogue,CLPT3. The present chemiluminescence-based strategy allows the concurrent detection of tyrosinase activity and biological thiols.

Original language	English
Pages (from-to)	11386-11389
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	86
DOIs	https://doi.org/10.1039/d1cc05217a
State	Published - 7 Nov 2021

Funding

Funders	Funder number
National Institutes of Health	1 S10 OD021508, CA68682
National Institutes of Health
Welch Foundation	F-0018
Welch Foundation
Israel Science Foundation

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title = "Turn on chemiluminescence-based probes for monitoring tyrosinase activity in conjunction with biological thiols",

abstract = "We report a chemiluminescent probe (CLPT1) that permits the paired detection of tyrosinase (Tyr) and biological thiols. Tyr only leads to a poor chemiluminescence response, a finding ascribed to the formation of a stableo-benzoquinone intermediate. The addition of glutathione (GSH), or ascorbate to theo-benzoquinone intermediate results in thiol conjugation or reduction to this intermediate, respectively. This produces a strong chemiluminescence response. Thiol co-dependence was demonstrated in live cells using the cell permeable analogue,CLPT3. The present chemiluminescence-based strategy allows the concurrent detection of tyrosinase activity and biological thiols.",

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AU - Shelef, Omri

AU - Sedgwick, Adam C.

AU - Pozzi, Sabina

AU - Green, Ori

AU - Satchi-Fainaro, Ronit

AU - Shabat, Doron

AU - Sessler, Jonathan L.

PY - 2021/11/7

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AB - We report a chemiluminescent probe (CLPT1) that permits the paired detection of tyrosinase (Tyr) and biological thiols. Tyr only leads to a poor chemiluminescence response, a finding ascribed to the formation of a stableo-benzoquinone intermediate. The addition of glutathione (GSH), or ascorbate to theo-benzoquinone intermediate results in thiol conjugation or reduction to this intermediate, respectively. This produces a strong chemiluminescence response. Thiol co-dependence was demonstrated in live cells using the cell permeable analogue,CLPT3. The present chemiluminescence-based strategy allows the concurrent detection of tyrosinase activity and biological thiols.

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Turn on chemiluminescence-based probes for monitoring tyrosinase activity in conjunction with biological thiols

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