Synthesis, Optical Properties and Biological Imaging of A New Two-photon Fluorescence Dye with Dicyano-group

LI Long-long; ZHAO Ning; LI Bing; PENG Dan; ZHOU Ning-ning; LIU Shi-xin

doi:10.3788/fgxb20173812.1575

您当前的位置：

首页 >

文章列表页 >

Synthesis, Optical Properties and Biological Imaging of A New Two-photon Fluorescence Dye with Dicyano-group

更新时间：2020-08-12

- Synthesis, Optical Properties and Biological Imaging of A New Two-photon Fluorescence Dye with Dicyano-group
- Chinese Journal of Luminescence Vol. 38, Issue 12, Pages: 1575-1581(2017)
- 作者机构：
  
  1. 山东省科学院新材料研究所山东省特种含硅新材料重点实验室,山东济南,250014
  2. 山东省计量科学研究院,山东济南,250014
  3. 山东省标准化研究院,山东济南,250014
- 作者简介：
- 基金信息：
  
  Supported by National Natural Science Foundation for Youth(51303097)
- DOI：10.3788/fgxb20173812.1575
  CLC： O625.67
- Received：26 April 2017，
  
  Revised：18 August 2017，
  
  Published Online：28 August 2017，
  
  Published：05 December 2017
- 稿件说明：
移动端阅览
李龙龙, 赵宁, 李冰等. 双氰基荧光染料的合成、光学性质及其生物成像[J]. 发光学报, 2017,38(12): 1575-1581

LI Long-long, ZHAO Ning, LI Bing etc. Synthesis, Optical Properties and Biological Imaging of A New Two-photon Fluorescence Dye with Dicyano-group[J]. Chinese Journal of Luminescence, 2017,38(12): 1575-1581
李龙龙, 赵宁, 李冰等. 双氰基荧光染料的合成、光学性质及其生物成像[J]. 发光学报, 2017,38(12): 1575-1581 DOI： 10.3788/fgxb20173812.1575.

LI Long-long, ZHAO Ning, LI Bing etc. Synthesis, Optical Properties and Biological Imaging of A New Two-photon Fluorescence Dye with Dicyano-group[J]. Chinese Journal of Luminescence, 2017,38(12): 1575-1581 DOI： 10.3788/fgxb20173812.1575.

摘要

设计合成了一种A--D--A型的双光子荧光染料3，6-双（4-乙烯基苯腈）-9-乙基咔唑，测试了其在二氯甲烷（DCM）、乙酸乙酯（EA）、乙醇（EtOH）、乙腈（ACN）、二甲亚砜（DMSO）和磷酸缓冲盐溶液（PBS）等不同溶剂中的紫外吸收光谱、单光子及双光子荧光光谱。化合物3，6-双（4-乙烯基苯腈）-9-乙基咔唑在紫外吸收光谱中存在两个相似的特征吸收带并呈现出复杂的溶剂化效应，在DMSO中具有最大荧光量子产率（86.02%），其相应的活性吸收截面为12.56 GM。在双光子荧光成像方面，染料分子具有优良的细胞膜通透性并且在双光子荧光显微镜下呈现出明亮的绿色荧光，表现出较好的双光子荧光成像性能。这些数据表明，化合物3，6-双（4-乙烯基苯腈）-9-乙基咔唑可用作一种较为理想的双光子荧光标记染料。

Abstract

A novel two-photon fluorescence dye 4

4'-((1Z

1'Z)-(9-ethyl-9H-carbazole-3

6-diyl)bis(ethene-2

1-diyl))dibenzonitrile was synthesized

and the linear absorption and fluorescent spectra of the dye in different solvents were investigated. The results indicate that the dye has a intricate solvent effect existing in UV-Vis absorption spectra

and the quantum yields and two-photon active cross-sections in DMSO are 86.02%

12.56 GM

respectively. About the images

the dye exhibites excellent cell membrane permeability and optical properties. These data show that the compound is a promising candidate for two-photon fluorescence labels.

关键词

Keywords

references

KIM M K, LIM C S, HONG J T, et al.. Sodium-ion-selective two-photon fluorescent probe for in vivo imaging[J]. Angew. Chem. Int. Ed., 2010, 49:364-367.

STALMANS S, WILLEMS M, ADRIAENS E, et al.. Flatworm models in pharmacological research:the importance of compound stability testing[J]. Regul. Toxicol. Pharm., 2014, 70:149-154.

YANEZ C O, ANDRADE C D, YAO S, et al.. Photosensitive polymeric materials for two-photon 3D WORM optical data storage systems[J]. ACS Appl. Mater. Interf., 2009, 1:2219-2229.

HONDT M D, BRACKE N, TAEVERNIE R, et al.. Related impurities in peptide medicines[J]. J. Pharm. Biomed. Anal., 2014, 101:2-30.

JHAVERI S J, MCMULLEN J D, SIJBESMA R, et al.. Direct three-dimensional microfabrication of hydrogels via two-photon lithography in aqueous solution[J]. Chem. Mater., 2009, 21(10):2003-2006.

STALMANS S, GEVAERT B, VERBEKE F, et al.. Quality control of cationic cell-penetrating peptides[J]. J. Pharmaceut. Biomed. Anal., 2016, 117:289-297.

XU D, JIANG L H. Designed filamentous cell penetrating peptides:probing supramolecular structure-dependent membrane activity and transfection efficiency[J]. Chem. Commun., 2015, 51:11757-11760.

LIN T C, CHUNG S J, KIM K S, et al.. Organics and polymers with high two-photon activities and their applications[J]. Adv. Polymer. Sci., 2003, 161:157-193.

OLIVEIRA S L, CORREA D S, MISOGUTI L, et al.. Perylene derivatives with large two-photon-absorption cross-sections for application in optical limiting and up conversion lasing[J]. Adv. Mater., 2005, 17(15):1890-1893.

PETER C F. Polychromophoric Metal complexes for generating the bioregulatory agent nitric oxide by single-and two-photon excitation[J]. ACC Chem. Res, 2008, 41(2):190-200.

DEMIZU Y, OBA M, OKITSU K, et al.. A preorganized -amino acid bearing aguanidinium side chain and its use in cell-penetrating peptides[J]. Org. Biomol. Chem., 2015, 13:5617-5620.

ELLIS-DAVIES G C R. Caged compounds:photorelease technology for control of cellular chemistry and physiology[J]. Nat. Meth., 2007, 4:619-628.

PISTON D W, BENNETT B D, YING G, et al.. Imaging of cellular dynamics by two-photon excitation microscopy[J]. Microsc. Soc. Am., 1995, 1:25-34.

成春文, 王风贺, 段伦超, 等. 一种新型罗丹明类荧光分子探针及其对Fe(Ⅲ)的选择性识别[J]. 发光学报, 2014, 35(1):125-130. CHENG C W, WANG F H, DUAN L C, et al.. Synthesis of a new fluorescent probe based on rhodamine and its performance in selective recognition of Fe(Ⅲ)[J]. Chin. J. Lumin., 2014, 35(1):125-130. (in Chinese)

SONG G F, SUN Y M, LIU Y, et al.. Low molecular weight fluorescent probes with good photostability for imaging RNA-rich nucleolus and RNA in iytoplasm in living cells[J]. Biomaterials, 2014, 35:2103-2112.

殷芳芳, 朱维菊, 方敏, 等. 咔唑-硫脲席夫碱荧光探针对Hg2+和Ag+的可视化识别[J]. 发光学报, 2015, 36(10):1137-1144. YIN F F, ZHU W J, FANG M, et al.. Visual recognition for Hg2+ and Ag+ of carbazole-thiourea schiff base fluorescence probe[J]. Chin. J. Lumin., 2015, 36(10):1137-1144. (in Chinese)

马永山, 张凤霞, 孙友敏, 等. 水溶性苝二酰亚胺类衍生物pH荧光探针的合成及表征[J]. 发光学报, 2011, 32(3):251-255. MA Y S, ZHANG F X, SUN Y M, et al.. Synthesis and characterization of a pH fluorescence probe based on water soluble perylene diimide derivative[J]. Chin. J. Lumin., 2011, 32(3):251-255. (in Chinese)

MIAO F, SONG G F, SUN Y M, et al.. Fluorescent imaging of acidic compartments in living cells with a high selective novel one-photon ratiometric and two-photon acidic pH probe[J]. Biosens. Bioelectron., 2013, 50:42-49.

MIAO F, ZHANG W J, SUN Y M, et al.. Novel fluorescent probes for highly selective two-photon imaging of mitochondria in living cells[J]. Biosens. Bioelectron., 2014, 55:423-429.

JUSTIN THOMAS K R, VELUSAMG M, LIN J T, et al.. Cyanocarbazole derivatives for high-performance electroluminescent devies[J]. Adv. Funct. Mater., 2004, 14(4):387-392.

王永涛, 赵栋, 陈婷婷, 等. 6-溴-3-(2,2-二氰基乙烯基)-N-正丁基咔唑的合成及其光谱性能[J]. 石河子大学学报, 2012, 30(5):625-629. WANG Y T, ZHAO D, CHEN T T, et al.. Synthesis and spectral properties of 6-bromo-3-(2,2-dinitrilevinyl)-N-butylcarbazole[J]. J. Shihezi Univ., 2012, 30(5):625-629. (in Chinese)

NARANG U, ZHAO C F, BHAWAKAR J D. Characterization of a new solvent-sensitive two-photon-induced fluorescent (aminostyryl) pyridinium salt dye[J]. Phys. Chem., 1996, 10:4521-4525.

FROMHERZ P. Monopole-dipole model for symmetrical solvatochromism of hemicyanine dyes[J]. J. Phys. Chem., 1995, 99:7188-7192.

ZHANG D H, ZHOU W, WONG X M. Solvents effects on the luminescent behavior of fluorescent molecules[J]. Inform. Record. Mater., 2010, 11(4):34-39.

Views

459

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Upconversion Fluorescence Photon Generation and Quantum Yield Quantification of Tm³⁺ in Waveguide-typed Aluminum Germanate Glasses

Related Author

ZHU Cai-ling

LIN Hai

WANG Zhi-qiang

ZHAO Xin

Related Institution

School of Textile and Material Engineering, Dalian Polytechnic University

School of Information Science and Engineering, Dalian Polytechnic University

AI问答

Address：No.3888 Dong Nanhu Road, Changchun, Jilin, China Postal code：130033
Tel：0431-86176862 Email：fgxbt@126.com
Technical support is provided by Beijing Founder electronics co., LTD 吉ICP备11002662号-17 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰