Penta-fluorophenol: a Smiles rearrangement-inspired cysteine-selective fluorescent probe for imaging of human glioblastoma

Abstract

A fluorescent molecular probe for the identification of glioblastoma is developed. The probe allows the tracing of the cysteine (Cys) level, which is recognized as a new biomarker of GBM.

Recent Advances in the Smiles Rearrangement: New Opportunities for Arylation

“…The polar Smiles rearrangement has also sought application in chemical biology, whereby a collaborative project involving Kim, Park, Park, Kang, Oh, and co-workers has shown that cysteine can be used as a nucleophilic component of the Smiles rearrangement, migrating a heterocycle to constitute a fluorescent probe (Scheme 10). 40 Compound 40 undergoes S N Ar via the thiol side-chain of cysteine (41), followed by an S-to-N Smiles rearrangement to give fluorescent compound 42. Given that cysteine levels in biopsy samples have been recognized as a biomarker for the disease glioblastoma, this Smiles based probe can provide a significant fluorescence output with no short-or long-term toxicity or immune response.…”

Concise Biothiol-Activatable HPQ-NBD Conjugate as a Targeted Theranostic Probe for Tumor Cells

“…Therefore, we hypothesized that the generated aggregates during the probe recognition process might produce a high toxicity to cancer cells, thereby killing them. At the same time, we found that Zhang et al reported a class of precipitated fluorophore HPQ (2-(2′-hydroxyphenyl)-4­(3 H )-quinazolinone) with strong insolubility, whose insolubility is regulated by the hydrogen bond between the phenolic hydroxyl group and the imine nitrogen. , Precipitated fluorophore cannot only perform fluorescence imaging in cells for a long time but also has the property of not diffusing easily in cells. − On the other hand, biothiol can be used as an excellent biomarker for the diagnosis and therapy of cancer, and 4-chloro-7-nitro-1,2,3-benzoxadiazole (NBD-Cl) was widely adopted for constructing fluorescent probes for the recognition of biothiol. − Based on the above consideration, we combined precipitated fluorophore HAPQ with NBD-Cl to construct a simple novel theranostic probe HAPQ-NBD . Probe HAPQ-NBD has the advantages of good selectivity, short response time, and satisfactory sensitivity for detecting three different classes of biothiols, including Cys, Hcy, and GSH.…”

A novel quinoline-based fluorescent probe for real-time monitoring of Cys in glioma

“…27 However, these methods have the disadvantages of high cost, time-consuming, complicated detection, and large toxic and side effects. Fortunately, the discovery of cysteine levels, both in human cells and in situ in humans, 28 as a new GBM biomarker, provides a new indicator for the early diagnosis and clinical surgical guidance of GBM.…”