Design and Synthesis of New Acridone-Based Nitric Oxide Fluorescent Probe.

Mikhail Panfilov,Alexander Moskalensky,Irina Khalfina,Aleksey Vorob’Ev,Darya Chernova

doi:10.3390/molecules26144340

Mikhail Panfilov, Alexander Moskalensky + Show 3 more

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https://doi.org/10.3390/molecules26144340

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Abstract

Nitric oxide (NO) is an important signaling molecule involved in a wide range of physiological and pathological processes. Fluorescent imaging is a useful tool for monitoring NO concentration, which could be essential in various biological and biochemical studies. Here, we report the design of a novel small-molecule fluorescent probe based on 9(10H)acridone moiety for nitric oxide sensing. 7,8-Diamino-4-carboxy-10-methyl-9(10H)acridone reacts with NO in aqueous media in the presence of O2, yielding a corresponding triazole derivative with fivefold increased fluorescence intensity. The probe was shown to be capable of nitric oxide sensing in living Jurkat cells.

Highlights

Being a unique molecule, nitric oxide (II) plays a vital role in many physiological processes
Monitoring the level and transformation pathways of nitric oxide is crucial for normal body functioning and for the further understanding of nitric oxide’s biological role
Nitration of 10-(carboxymethyl)-9(10H)acridone ethyl ester (1) with nitric acid in Ac2O/AcOH mixture quantitatively yielded nitro derivative 2, which was reduced with formic acid over Pd/C in ethanol to give aminoacridone 3

Summary

Introduction

Nitric oxide (II) plays a vital role in many physiological processes. The design of the majority of such fluorescent probes is based on the conjugation of fluorophore with phenylene1,2-diamine moiety, which undergoes oxygen-promoted reaction with NO forming the triazole ring. Such transformation causes significant growth of fluorescence quantum yield by blocking the photoinduced electron transfer [7,8]. To this day, a wide range of NO probes utilizing the abovementioned principle have been reported with BODIPY [9], coumarin [10,11], fluorescein [12], rhodamine [13,14], and other fluorophores. We hypothesized that the incorporation of the o-diamine fragment along with the carboxylic group would improve water solubility

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