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Gadolinium-based MRI contrast agent for the detection of tyrosinase

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Abstract

Tyrosinase is a key enzyme that has long been considered as a biomarker for melanoma as it catalyzes the oxidation of tyrosine and L-DOPA in melanogenesis. Recent studies also suggest a link between tyrosinase activity and Parkinson's disease; however, the mechanism of tyrosinase-mediated melanin formation in the brain is poorly understood. To better understand this connection, more advanced tools for the detection of tyrosinase in the brain are required. Herein, we successfully designed and synthesized a tyrosinase-targeting Gd(III)-based MR contrast agent Tyr-GBCA 1. Tyr-GBCA 1 was synthesized by linking m-hydroxyphenyl to Gd-DOTA via a self-immolative linker. Tyr-GBCA 1 shows a 21% increase in the T1 relaxation rate (R1) in the presence of tyrosinase in artificial cerebral spinal fluid. Furthermore, Tyr-GBCA 1 is unreactive to hydrogen peroxide, which is a potential interferent in oxidation-based tyrosinase sensing systems. The reaction mechanism of the probe was studied by electrospray ionization (ESI) mass spectrometry and supports the cleavage of a reaction site.

Graphical abstract: Gadolinium-based MRI contrast agent for the detection of tyrosinase

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Supplementary files

Article information


Submitted
04 Nov 2019
Accepted
14 Dec 2019
First published
17 Dec 2019

Analyst, 2020, Advance Article
Article type
Communication

Gadolinium-based MRI contrast agent for the detection of tyrosinase

H. Seo and H. A. Clark, Analyst, 2020, Advance Article , DOI: 10.1039/C9AN02213A

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