TitleComparative Studies of Multi-Photon Induced Emission by Pyridine-Based Small Molecular Probes in Biological Media: Selective Binding of Bioactive Molecules and In Vitro Imaging
AuthorsWu, Wanqing
Kong, Hoi-Kuan
Li, Hongguang
Ho, Yu-Man
Gao, Yuan
Hao, Jianhua
Murphy, Margaret B.
Lam, Michael Hon-Wah
Wong, Ka-Leung
Lee, Chi-Sing
AffiliationCity Univ Hong Kong, Dept Biol & Chem, Kowloon Tong, Hong Kong, Peoples R China.
Shenzhen Univ Town, Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol,Lab Chem Genom, Shenzhen 518055, Peoples R China.
Hong Kong Polytech Univ, Dept Appl Phys, Hung Hum, Hong Kong, Peoples R China.
Hong Kong Baptist Univ, Dept Chem, Kowloon Tong, Hong Kong, Peoples R China.
City Univ Hong Kong, Dept Biol & Chem, TatChee Ave, Kowloon Tong, Hong Kong, Peoples R China.
KeywordsAnions
Fluorescent probes
Imaging agents
Luminescence
Photochemistry
2-PHOTON
EXCITATION
COMPLEX
Issue Date2011
Publisher欧洲有机化学杂志
CitationEUROPEAN JOURNAL OF ORGANIC CHEMISTRY.2011,(26),5054-5060.
AbstractA new class of organic molecular probes (1-3) based on a 1,3-disubstituted diethynylbenzene core has been developed. Both 1 and 2 (with the esters of 1 replaced by diethylamides in 2) show good linear and three-photon induced photophysical properties with two-photon absorption cross-sections (185-210 cm(4)s photon(-1) molecule(-1)) that are suitable for biological applications in live specimens. The propeller pi-conjugated systems of 3 (a C(3) analogue of 1) shows threefold enhancement for the two-photon absorption cross-section (650 cm(4)s photon(-1)molecule(-1)). Solvatochromism was observed in the fluorescence spectra of all these molecular probes; in acidic medium (pH = 4-5) their fluorescence emissions are slightly blueshifted with a threefold enhancement in intensity relative to those observed under basic conditions (pH = 10-11). In the fluorometric titration study against a variety of bioactive small molecules, only 2 shows strong binding affinity (log K(B) > 7) towards citrates and bicarbonates with approximately 30 nm redshift. The in vitro emission spectra of 2 obtained show the same emission upon addition of anions to the solution. The results of these studies could provide new molecular-design strategies for two-photo absorption (TPA) chromophores and new materials for two/multi-photon imaging in vitro.
URIhttp://hdl.handle.net/20.500.11897/238146
ISSN1434-193X
DOI10.1002/ejoc.201100570
IndexedSCI(E)
Appears in Collections:化学生物学与生物技术学院

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