A new dehydroabietic acid-based arylamine fluorescent probe: Synthesis, structure analysis and in vitro biodiagnose function

被引：20

作者：

Gao, Hong ^{[1
,2
]}

Chen, Shanshan ^{[3
]}

Rao, Xiaoping ^{[1
]}

Shang, Shibin ^{[1
]}

Song, Zhanqian ^{[1
]}

机构：

[1] CAF, Inst Chem Ind Forestry Prod, Natl Engn Lab Biomass Chem Utilizat, Key & Lab Forest Chem Engn,SFA,Key Lab Biomass En, Nanjing 210042, Jiangsu, Peoples R China

[2] CAF, Inst Forest New Technol, Beijing 100091, Peoples R China

[3] Nanjing Normal Univ, Coll Chem & Environm Sci, Nanjing 210046, Jiangsu, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2013年 / 23卷 / 07期

基金：

中国国家自然科学基金;

关键词：

Dehydroabietic acid-based arylamine; Synthesis; Structure; Fluorescent probe; QUANTUM DOTS; QUINOXALINES; VIVO;

D O I：

10.1016/j.bmcl.2013.01.035

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new fluorescent probe (methyl 13-(alpha-naphthalene)aminodeisopropyldehydroabietate) has been synthesized, and its structure was optimized by theoretical DFT calculation and determinated by single-crystal X-ray diffraction analysis. The optimized data are in agreement with the experimental values. The fluorescence properties, photostability, cell toxicity and in vitro fluorescence imaging of the compound have been investigated. The results indicated that it can be effectively taken up by HeLa, 7721, 7901 and A549 cells and strong blue fluorescence signals were detected in these cells. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：2254 / 2259

页数：6

共 26 条

[1] Fluorescence characteristics of some dehydroabietic acid-based arylamines [J].

Burrows, H. D. ;

Chattopadhyay, N. ;

Esteves, M. A. ;

Fernandes, M. ;

Gigante, B. .

JOURNAL OF FLUORESCENCE, 2007, 17 (06) :701-706

[2] Fluorescence study of dehydroabietic acid-based bipolar arylamine-quinoxalines [J].

Burrows, H. D. ;

Fonseca, S. M. ;

Gigante, B. ;

Esteves, M. A. ;

Guerreiro, A. M. .

JOURNAL OF FLUORESCENCE, 2006, 16 (02) :227-231

[3] Aqueous one-pot synthesis of bright and ultrasmall CdTe/CdS near-infrared-emitting quantum dots and their application for tumor targeting in vivo [J].

Chen, Li-Na ;

Wang, Jing ;

Li, Wen-Tao ;

Han, He-You .

CHEMICAL COMMUNICATIONS, 2012, 48 (41) :4971-4973

[4] A Dual-Emission Forster Resonance Energy Transfer Nanoprobe for Sensing/Imaging pH Changes in the Biological Environment [J].

Chiu, Ya-Ling ;

Chen, Show-An ;

Chen, Jean-Hong ;

Chen, Ko-Jie ;

Chen, Hsin-Lung ;

Sung, Hsing-Wen .

ACS NANO, 2010, 4 (12) :7467-7474

[5] Synthesis and antiviral evaluation of benzimidazoles, quinoxalines and indoles from dehydroabietic acid [J].

Fonseca, T ;

Gigante, B ;

Marques, MM ;

Gilchrist, TL ;

De Clercq, E .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (01) :103-112

[6]

Frisch MJ, 2003, GAUSSIAN 03 REVISION

[7] Methyl 12-bromodehydroabietate [J].

Gao, Hong ;

Song, Zhan-Qian ;

Shang, Shi-Bin .

ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 :O1207-U1186

[8] Catechols from abietic acid:: Synthesis and evaluation as bioactive compounds [J].

Gigante, B ;

Santos, C ;

Silva, AM ;

Curto, MJM ;

Nascimento, MSJ ;

Pinto, E ;

Pedro, M ;

Cerqueira, F ;

Pinto, MM ;

Duarte, MP ;

Laires, A ;

Rueff, J ;

Gonçalves, J ;

Pegado, MI ;

Valdeira, ML .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (08) :1631-1638

[9] Quantum chemical calculation studies on 4-phenyl-1-(propan-2-ylidene)thiosemicarbazide [J].

Jian, FF ;

Zhao, PS ;

Bai, ZS ;

Zhang, L .

STRUCTURAL CHEMISTRY, 2005, 16 (06) :635-639

[10] A Drug-Loaded Aptamer-Gold Nanoparticle Bioconjugate for Combined CT Imaging and Therapy of Prostate Cancer [J].

Kim, Dongkyu ;

Jeong, Yong Yeon ;

Jon, Sangyong .

ACS NANO, 2010, 4 (07) :3689-3696

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