Near-infrared pH probes based on phenoxazinium connecting with nitrophenyl and pyridinyl groups

被引：10

作者：

Zhu, Wei-Jin ^{[1
]}

Niu, Jin-Yun ^{[2
]}

He, Dan-Dan ^{[1
]}

Sun, Ru ^{[1
]}

Xu, Yu-Jie ^{[2
]}

Ge, Jian-Feng ^{[1
,3
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, 199 RenAi Rd, Suzhou 215123, Peoples R China

[2] Soochow Univ, Coll Med, Sch Radiat Med & Protect, Suzhou 215123, Peoples R China

[3] Chinese Acad Sci, Jiangsu Key Lab Med Opt, Suzhou Inst Biomed Engn & Technol, Suzhou 215163, Peoples R China

来源：

DYES AND PIGMENTS | 2018年 / 149卷

基金：

中国国家自然科学基金;

关键词：

Phenoxazinium; Phenoxazine; Equilibrium; Near-infrared emission; Lysosome biomarker; FLUORESCENT-PROBE; CANCER-CELLS; IN-VITRO; WATER; SENSOR; FLUOROPHORES; DERIVATIVES; EMISSION; DESIGN; IONS;

D O I：

10.1016/j.dyepig.2017.09.059

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Three phenoxazinium compounds attached with o-nitrophenyl (3a), m-nitrophenyl (3b) and p-nitro phenyl (3c) groups were prepared, and the pH promoted emission spectra were used to evaluate the deprotonated-protonated equilibrium between phenoxazinium and phenoxazine. They showed nearly ON-OFF emission responses at 650-850 nm around pH 8.0-10.8, and the fluorescence related pK(a)s of 3a -c were 8.7, 9.2, and 8.9, respectively. Two phenoxazinium compounds attached with pyridinyl groups (7a-b) were further prepared, the pH promoted emission spectra were influenced by both the deprotonated-protonated equilibrium between phenoxazinium and phenoxazine, and the equilibrium between pyridinyl group and pyridinumyl group. They exhibited more strong red and near-infrared emission at 600-850 nm, probe 7a gave pK(a),1 = 3.71 and pK(a),2 = 9.68, and that of probe 7b was 2.75. Moreover, the fluorescent imaging experiment indicated that probe 7a was a lysosome biomarker for V79 and HeLa cells. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：481 / 490

页数：10

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