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Synthesis and Characterization of Water-Soluble Conjugated Oligoelectrolytes for Near-Infrared Fluorescence Biological Imaging

Authors
 Shin-Jae Woo  ;  Sungmin Park  ;  Ji-Eun Jeong  ;  Yoochan Hong  ;  Minhee Ku  ;  Bo Yun Kim  ;  Il Ho Jang  ;  Soon Chul Heo  ;  Taejun Wang  ;  Ki Hean Kim  ;  Jaemoon Yang  ;  Jae Ho Kim  ;  Han Young Woo 
Citation
 ACS APPLIED MATERIALS & INTERFACES, Vol.8(25) : 15937-15947, 2016 
Journal Title
 ACS APPLIED MATERIALS & INTERFACES 
ISSN
 1944-8244 
Issue Date
2016
Keywords
Stokes shift ; bioimaging ; conjugated oligoelectrolytes ; near-infrared fluorophores ; vesicle
Abstract
Near-infrared (NIR) fluorophores attract increasing attention as a molecular marker (or probe) for in vivo and in vitro biological fluorescence imaging. Three types of new NIR fluorescent conjugated oligoelectrolytes (COEs: Q-FlTBTTFl, Q-FlBBTFl, and Q-FlTBBTTFl) are synthesized with quaternized ammonium ionic groups in their side-chains for water solubility. The emission wavelength is modulated in the range 600-1300 nm, by adjusting the intramolecular charge transfer in the molecular backbone based on the electron-rich fluorene (and/or thiophene) and electron-deficient benzo[2,1,3]thiadiazole (or benzo[1,2-c:4,5-c']bis[1,2,5]thiadiazole) moieties. The COEs show a remarkably larger Stokes shift (147-276 nm) compared to commercial rhodamine and cyanine dyes in water, avoiding self-quenching and interference from the excitation backscattered light. The photoluminescence (PL) quantum efficiency is improved substantially by up to 27.8% in water by fabricating a vesicular complex, COE/v, with a block ionomer, poly[(ethylene oxide)-block-(sodium 2-acrylamido-2-methyl-1-propanesulfonate)]. In vitro cellular uptake images with the COEs are obtained with good biocompatibility by confocal single-photon and two-photon microscopy. The ex vivo and in vivo images of a mouse xenograft model treated with the Q-FlBBTFl/v exhibit a substantially stronger fluorescence signal at the tumor site than at the other organs, highlighting the potential of the COE/v as an NIR fluorescent imaging agent for the diagnosis of cancer
Full Text
http://pubs.acs.org/doi/abs/10.1021/acsami.6b04276
DOI
10.1021/acsami.6b04276
Appears in Collections:
1. College of Medicine (의과대학) > Dept. of Radiology (영상의학교실) > 1. Journal Papers
Yonsei Authors
Ku, Min Hee(구민희) ORCID logo https://orcid.org/0000-0002-1674-1474
Yang, Jae Moon(양재문) ORCID logo https://orcid.org/0000-0001-7365-0395
URI
https://ir.ymlib.yonsei.ac.kr/handle/22282913/152365
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