Synthesis and Characterization of Water-Soluble Conjugated Oligoelectrolytes for Near-Infrared Fluorescence Biological Imaging
- Authors
- Woo, Shin-Jae; Park, Sungmin; Jeong, Ji-Eun; Hong, Yoochan; Ku, Minhee; Kim, Bo Yun; Jang, Il Ho; Heo, Soon Chul; Wang, Taejun; Kim, Ki Hean; Yang, Jaemoon; Kim, Jae Ho; Woo, Han Young
- Issue Date
- 29-6월-2016
- Publisher
- AMER CHEMICAL SOC
- Keywords
- conjugated oligoelectrolytes; near-infrared fluorophores; vesicle; Stokes shift; bioimaging
- Citation
- ACS APPLIED MATERIALS & INTERFACES, v.8, no.25, pp.15937 - 15947
- Indexed
- SCIE
SCOPUS
- Journal Title
- ACS APPLIED MATERIALS & INTERFACES
- Volume
- 8
- Number
- 25
- Start Page
- 15937
- End Page
- 15947
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/88295
- DOI
- 10.1021/acsami.6b04276
- ISSN
- 1944-8244
- 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-FITBTTFI, Q-FIBBTFI, and Q-FITBBTTFI) 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 QFIBBTFliv 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.
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