BODIPY-derived piperazidine fluorescent near-neutral pH indicator and its bioimaging

被引：25

作者：

Deng, Min

Yang, Chengduan

Gong, Deyan

Iqbal, Anam

Tang, Xiaoliang

Liu, Weisheng

Qin, Wenwu ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, Key Lab Nonferrous Met Chem & Resources Utilizat, Lanzhou 730000, Peoples R China

来源：

SENSORS AND ACTUATORS B-CHEMICAL | 2016年 / 232卷

基金：

美国国家科学基金会;

关键词：

BODIPY; Piperazine; Near-neutral pH; Biological cells; PHOTOPHYSICAL PROPERTIES; LASING PROPERTIES; DYES; DERIVATIVES; PROBES;

D O I：

10.1016/j.snb.2016.04.003

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

Two new 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes (1 and 2) with piperazine subunits on position 3 or 5 were synthesized. Their absorption and steady-state fluorescence properties were investigated as a function of solvent. In water/MeCN (9:1, V/V) solution, the dyes show fluorescent enhancement upon increasing the acidity of the solution. They can be used in water/MeCN (9:1, V/V) solution as fluorescent pH probes excitable with visible light, with pK(a) values near-neutral (around 6.5 and 6.8). Dyes 1 and 2 are readily taken up by biological cells in the cytosol where it has no obvious toxic effects. (C) 2016 Elsevier B.V. All rights reserved.

引用

页码：492 / 498

页数：7

共 29 条

[1]

[Anonymous], SHELX 97 PROGRAM CRY

[2] Correlations between photophysics and lasing properties of dipyrromethene-BF2 dyes in solution [J].

Arbeloa, TL ;

Arbeloa, FL ;

Arbeloa, IL ;

García-Moreno, I ;

Costela, A ;

Sastre, R ;

Amat-Guerri, F .

CHEMICAL PHYSICS LETTERS, 1999, 299 (3-4) :315-321

[3] Boradiazaindacene-appended calix[4]arene: Fluorescence sensing of pH near neutrality [J].

Baki, CN ;

Akkaya, EU .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1512-1513

[4] BODIPY-based hydroxyaryl derivatives as fluorescent pH probes [J].

Baruah, M ;

Qin, WW ;

Basaric, N ;

De Borggraeve, WM ;

Boens, N .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4152-4157

[5] Rational Design, Synthesis, and Spectroscopic and Photophysical Properties of a Visible-Light-Excitable, Ratiometric, Fluorescent Near-Neutral pH Indicator Based on BODIPY [J].

Boens, Noel ;

Qin, Wenwu ;

Baruah, Mukulesh ;

De Borggraeve, Wim M. ;

Filarowski, Aleksander ;

Smisdom, Nick ;

Ameloot, Marcel ;

Crovetto, Luis ;

Talavera, Eva M. ;

Alvarez-Pez, Jose M. .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (39) :10924-10934

[6] DECOMPOSITION OF N-METHYL-N-NITROSOTOLUENE-PARA-SULPHONAMIDE IN BASIC-MEDIA - HYDROLYSIS AND TRANSNITROSATION REACTIONS [J].

CASTRO, A ;

LEIS, JR ;

PENA, ME .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (11) :1861-1866

[7] Synthesis and spectroscopic characterisation of fluorescent indicators for Na+ and K+ [J].

Cielen, E ;

Tahri, A ;

Heyen, KV ;

Hoornaert, GJ ;

De Schryver, FC ;

Boens, N .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (07) :1573-1580

[8] Synthesis and characterisation of Thio-H, a new excitation and emission ratioable fluorescent Ca2+/Mg2+ indicator with high brightness [J].

Cielen, E ;

Stobiecka, A ;

Tahri, A ;

Hoornaert, GJ ;

De Schryver, FC ;

Gallay, J ;

Vincent, M ;

Boens, N .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2002, (06) :1197-1206

[9] Photophysical and lasing properties of new analogs of the boron-dipyrromethene laser dye PM567 in liquid solution [J].

Costela, A ;

García-Moreno, I ;

Gomez, C ;

Sastre, R ;

Amat-Guerri, F ;

Liras, M ;

Arbeloa, FL ;

Prieto, JB ;

Arbeloa, IL .

JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (34) :7736-7742

[10]

Desvergne J.-P., 1997, CHEMOSENSORS ION MOL

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