Bioinspired water-soluble two-photon fluorophores

被引:21
作者
Beltran Rodrigues, Ana Clara [1 ]
Afonso Mariz, Ines de Fatima [2 ]
Sengo Macoas, Ermelinda Maria [2 ]
Tonelli, Renata Rosito [3 ]
Gaspar Martinho, Jose Manuel [2 ]
Quina, Frank Herbert [1 ]
Bastos, Erick Leite [1 ]
机构
[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Sao Paulo, SP, Brazil
[2] Univ Lisbon, Inst Super Tecn, Ctr Quim Fis Mol, Lisbon, Portugal
[3] Univ Fed Sao Paulo, Dept Ciencias Farmaceut, Diadema, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
Fluorescence; Two-phot; on absorption; Betalains Bioimaging; FLUORESCENCE QUANTUM YIELDS; PHOTOPHYSICAL PROPERTIES; EXCITED-STATE; DENSITY FUNCTIONALS; NATURAL-PRODUCTS; ABSORPTION; EXCITATION; PROBES; STANDARDS; PURIFICATION;
D O I
10.1016/j.dyepig.2017.11.020
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The structural modification of plant pigments allows the development of new functional dyes with tailored photophysical properties. Two-photon excitation fluorescence microscopy has emerged as an important technique, but requires the use of fluorophores having large two-photon absorption cross-sections in water. This feature is rarely found in natural or artificial dyes, but betalains, the main pigments of beetroots and some species of fluorescent flowers, can be modified to produce water-soluble two-photon fluorophores. Herein we describe the semisynthesis and photophysical characterization of two water-soluble artificial coumarinic betalains. The excitation of these compounds in the near-infrared results in yellow fluorescence with two-photon cross-sections in water of 323 GM and 179 GM.
引用
收藏
页码:105 / 111
页数:7
相关论文
共 66 条
[31]   Multiphoton microscopy in life sciences [J].
König, K .
JOURNAL OF MICROSCOPY, 2000, 200 (02) :83-104
[32]  
Lakowicz J.R., 2006, Principles of Fluorescence Spectroscopy, P27, DOI [https://doi.org/10.1007/978-0-387-46312-4, DOI 10.1007/978-0-387-46312-4, 10.1007/978-0-387-46312-42, 10.1007/978-0-387-46312-4]
[33]   Bright ideas for chemical biology [J].
Lavis, Luke D. ;
Raines, Ronald T. .
ACS CHEMICAL BIOLOGY, 2008, 3 (03) :142-155
[34]   Molecular engineering of two-photon fluorescent probes for bioimaging applications [J].
Liu, Hong-Wen ;
Liu, Yongchao ;
Wang, Peng ;
Zhang, Xiao-Bing .
METHODS AND APPLICATIONS IN FLUORESCENCE, 2017, 5 (01)
[35]   Multiwfn: A multifunctional wavefunction analyzer [J].
Lu, Tian ;
Chen, Feiwu .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 2012, 33 (05) :580-592
[36]   A V-shaped cationic dye for nonlinear optical bioimaging [J].
Macoas, Ermelinda ;
Marcelo, Gema ;
Pinto, Sandra ;
Caneque, Tatiana ;
Cuadro, Ana M. ;
Vaquero, Juan J. ;
Martinho, Jose M. G. .
CHEMICAL COMMUNICATIONS, 2011, 47 (26) :7374-7376
[37]  
Magde D, 2002, PHOTOCHEM PHOTOBIOL, V75, P327, DOI 10.1562/0031-8655(2002)075<0327:FQYATR>2.0.CO
[38]  
2
[39]   Two-photon absorption standards in the 550-1600 nm excitation wavelength range [J].
Makarov, Nikolay S. ;
Drobizhev, Mikhail ;
Rebane, Aleksander .
OPTICS EXPRESS, 2008, 16 (06) :4029-4047