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

Tel Aviv University

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

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

All Science Journal Classification (ASJC) codes

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d1cc05217a

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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.",

author = "Omri Shelef and Sedgwick, \{Adam C.\} and Sabina Pozzi and Ori Green and Ronit Satchi-Fainaro and Doron Shabat and Sessler, \{Jonathan L.\}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",

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doi = "10.1039/d1cc05217a",

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TY - JOUR

T1 - Turn on chemiluminescence-based probes for monitoring tyrosinase activity in conjunction with biological thiols

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

Y1 - 2021/11/7

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=85118435088&partnerID=8YFLogxK

U2 - 10.1039/d1cc05217a

DO - 10.1039/d1cc05217a

M3 - مقالة

C2 - 34647549

SN - 1359-7345

VL - 57

SP - 11386

EP - 11389

JO - Chemical Communications

JF - Chemical Communications

IS - 86

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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