Development of a hybrid rhodamine-hydrazine NIR fluorescent probe for sensitive detection and imaging of peroxynitrite in necrotizing enterocolitis model

IF 4.5 2区医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Bioorganic Chemistry Pub Date : 2024-08-21 DOI:10.1016/j.bioorg.2024.107729

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Abstract

This study describes the synthesis and characterization of a novel near-infrared (NIR) fluorescent probe RBNE based on a hybrid rhodamine dye, which shows excellent optical capability for detecting and imaging ONOO⁻ in necrotizing enterocolitis (NEC) mouse model. The probe RBNE undergoes hydrazine redox-process, and subsequently the spirocyclic structure’s opening, resulting in a turn-on fluorescence emission with the presence of ONOO⁻, which exhibits several excellent features, including a significant Stokes shift of 108 nm, near-infrared emission at 668 nm, a lower detection limit of 56 nM, low cytotoxicity, and excellent imaging ability for ONOO⁻ both in vitro and in vivo. The presented study introduces a novel optical tool that has the potential to significantly advance our understanding of peroxynitrite (ONOO⁻) behaviors in necrotizing enterocolitis (NEC).

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开发一种混合罗丹明-肼近红外荧光探针，用于在坏死性小肠结肠炎模型中灵敏检测和成像过氧化亚硝酸盐

本研究介绍了一种基于混合罗丹明染料的新型近红外（NIR）荧光探针 RBNE 的合成和表征，该探针在坏死性小肠结肠炎（NEC）小鼠模型中具有出色的检测和成像 ONOO- 的光学能力。探针 RBNE 经历了肼氧化还原过程，随后螺环结构打开，从而在 ONOO- 存在时开启荧光发射，该探针表现出多种优异特性，包括显著的 108 nm 斯托克斯偏移、668 nm 的近红外发射、56 nM 的较低检测限、低细胞毒性以及优异的体外和体内 ONOO- 成像能力。本研究介绍了一种新型光学工具，它有可能极大地促进我们对坏死性小肠结肠炎（NEC）中过氧化亚硝酸盐（ONOO-）行为的了解。

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来源期刊

Bioorganic Chemistry 生物-生化与分子生物学

CiteScore

9.70

自引率

3.90%

发文量

679

审稿时长

31 days

期刊介绍： Bioorganic Chemistry publishes research that addresses biological questions at the molecular level, using organic chemistry and principles of physical organic chemistry. The scope of the journal covers a range of topics at the organic chemistry-biology interface, including: enzyme catalysis, biotransformation and enzyme inhibition; nucleic acids chemistry; medicinal chemistry; natural product chemistry, natural product synthesis and natural product biosynthesis; antimicrobial agents; lipid and peptide chemistry; biophysical chemistry; biological probes; bio-orthogonal chemistry and biomimetic chemistry. For manuscripts dealing with synthetic bioactive compounds, the Journal requires that the molecular target of the compounds described must be known, and must be demonstrated experimentally in the manuscript. For studies involving natural products, if the molecular target is unknown, some data beyond simple cell-based toxicity studies to provide insight into the mechanism of action is required. Studies supported by molecular docking are welcome, but must be supported by experimental data. The Journal does not consider manuscripts that are purely theoretical or computational in nature. The Journal publishes regular articles, short communications and reviews. Reviews are normally invited by Editors or Editorial Board members. Authors of unsolicited reviews should first contact an Editor or Editorial Board member to determine whether the proposed article is within the scope of the Journal.