کد مقاله کد نشریه سال انتشار مقاله انگلیسی ترجمه فارسی نسخه تمام متن
4765737 1362360 2018 7 صفحه PDF ندارد دانلود رایگان
عنوان انگلیسی مقاله
A novel nitroethylene-based porphyrin as a NIR fluorescence turn-on probe for biothiols based on the Michael addition reaction
کلمات کلیدی
Porphyrin; Nitroethylene; Fluorescent biothiol probe; Cell imaging;
موضوعات مرتبط
مهندسی و علوم پایه مهندسی شیمی مهندسی شیمی (عمومی)
پیش نمایش صفحه اول مقاله
A novel nitroethylene-based porphyrin as a NIR fluorescence turn-on probe for biothiols based on the Michael addition reaction
چکیده انگلیسی

•A novel NIR fluorescence turn-on probe for biothiols based on the Michael addition reaction.•Nitroethylene group successfully introduced to a porphyrin platform for quenching its fluorescence.•An excellent porphyrin-based biothiol probe with good biocompatibility and long-wavelength emission.

Biothiols, such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH), play essential roles in many physiological and pathological processes. In this work, three porphyrin derivatives, XQ1, XQ2 and XQ3, were synthesized by combining the porphyrin framework with nitroethylene, bis(methoxycarbonyl)ethylene and dicyanoethylene moieties, respectively. XQ1 was almost nonfluorescent, which could be utilized as a good starting point for developing fluorescence turn-on probes. Thus, XQ1 exhibits fast fluorescence enhancement and high selectivity towards the biothiols based on the Michael addition mechanism. It also exhibits high sensitivity towards the biothiols with the detection limits of 0.65–1.1 μM. In addition, XQ1 was successfully applied to cell imaging in living A549 cells for visualizing the biothiols. The results compose a good example of designing porphyrin derivatives for detecting biothiols, with the advantages of dramatic fluorescence enhancement in the NIR wavelength range, which exhibits good cell membrane permeability and practicability in detecting both exogenous and endogenous biothiols.

Graphical abstractA novel nitroethylene-based porphyrin was synthesized and used as a NIR fluorescent probe for biothiols based on the Michael addition reaction.Download high-res image (205KB)Download full-size image

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Dyes and Pigments - Volume 148, January 2018, Pages 437-443
نویسندگان
, , , , , ,