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

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.

Fluorescent dyes based on rhodamine derivatives for bioimaging and therapeutics: recent progress, challenges, and prospects

“…254,255 It can be endogenously synthesized by three different isoforms of nitric oxide synthase and plays an important role in numerous physiological and pathological processes, such as neuronal signal transduction, immune response, programmed cell death, vasodilation, inhibition of protein and DNA damage, and endothelial dysfunction. 256–262 Moreover, maintaining NO homeostasis reduces the risk of cancer and neurodegenerative diseases. 263,264…”

“…254,255 It can be endogenously synthesized by three different isoforms of nitric oxide synthase and plays an important role in numerous physiological and pathological processes, such as neuronal signal transduction, immune response, programmed cell death, vasodilation, inhibition of protein and DNA damage, and endothelial dysfunction. [256][257][258][259][260][261][262] Moreover, maintaining NO homeostasis reduces the risk of cancer and neurodegenerative diseases. 263,264 Gong et al on the basis of maintaining the rigid planar structure of rhodamine B, designed and prepared an efficient near-infrared dye HN7 by expanding the polyconjugated system of rhodamine B.…”

Smart probes for optical imaging of T cells and screening of anti-cancer immunotherapies

“…39 In another example of cellular uptake, Vorob'ev et al described the preparation of an acridone-based probe for sensing NO in human Jurkat T cells. 40 In this case, the reaction between the smart probe and NO yielded a triazole derivative with increased fluorescence -due to blockage of photoinduced electron transfer (PeT)-and an hypsochromic shift in the emission wavelength (e.g., from 564 nm to 495 nm). Metabolism-associated enzymes are also attractive targets for imaging T cells.…”

Recent progress of organic fluorescent molecules for bioimaging applications: cancer-relevant biomarkers

“…30 The NO appearing in tumor cells is known to promote tumor progression by inducing tumor proliferation and the expression of angiogenic factors. 31 So designing fluorescent probes with the ability to image NO in a tumor environment is of great interest for applications.…”