A wavelength-tunable and facilely functionable D-A type naphthalene core skeleton: Synthesis, photophysical property, and bio-imaging applications for cells and tissues

Yuna Jung; Youngseo Kim; Na Hee Kim; Junho Lee; Kang Hoon Kim; Junyang Jung; Youngbuhm Huh; Hyeung Jin Jang; Jinmyoung Joo; Sungnam Park; Dokyoung Kim

doi:10.1016/j.dyepig.2018.10.016

A wavelength-tunable and facilely functionable D-A type naphthalene core skeleton: Synthesis, photophysical property, and bio-imaging applications for cells and tissues

Yuna Jung, Youngseo Kim, Na Hee Kim, Junho Lee, Kang Hoon Kim, Junyang Jung, Youngbuhm Huh, Hyeung Jin Jang, Jinmyoung Joo, Sungnam Park, Dokyoung Kim

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

A new wavelength-tunable and facilely functionable electron donor (D)-acceptor (A) type fluorescent naphthalene core skeleton and its application for cell membrane imaging are reported. The core skeleton shows bright green fluorescence with aldehyde(–CHO) moiety at the electron acceptor site, and its emission wavelength is tuned to blue and red by introducing the moiety of nitrile (–CN) and dicyanovinyl (–CH(CN)₂), respectively, at the acceptor site. In addition, the core skeleton can be readily functionable by introducing a targeting moiety at the extra hydroxyl group. For the first demonstration as a fluorescent probe, a long-chain carbon is introduced and evaluated its bio-imaging ability for the cellular membranes on cells and tissues by using confocal laser scanning microscopy (CLSM) and two-photon microscopy (TPM). The synthesis, photophysical property, and quantum chemical calculations are also identified.

Original language	English
Pages (from-to)	104-111
Number of pages	8
Journal	Dyes and Pigments
Volume	162
DOIs	https://doi.org/10.1016/j.dyepig.2018.10.016
Publication status	Published - 2019 Mar

Bibliographical note

Funding Information:
This research was supported by the Bio & Medical Technology Development Program of the National Research Foundation (NRF) of Korea funded by the Ministry of Science & ICT (NRF-2018-M3A9H3021707). This research was also supported by Basic Science Research Program through the National Research Foundation (NRF) of Korea funded by the Ministry of Education (NRF-2018-R1A6A1A03025124, NRF-2018-R1D1A1B07043383, NRF-2017-R1D1A1B03035525). J. Joo thanks to the financial support (2018–7045) from the Asan Institute for Life Sciences, Asan Medical Center, Seoul, Korea.

Funding Information:
This research was supported by the Bio & Medical Technology Development Program of the National Research Foundation (NRF) of Korea funded by the Ministry of Science & ICT ( NRF-2018-M3A9H3021707 ). This research was also supported by Basic Science Research Program through the National Research Foundation (NRF) of Korea funded by the Ministry of Education ( NRF-2018-R1A6A1A03025124 , NRF-2018-R1D1A1B07043383 , NRF-2017-R1D1A1B03035525 ). J. Joo thanks to the financial support ( 2018–7045 ) from the Asan Institute for Life Sciences, Asan Medical Center, Seoul, Korea .

Publisher Copyright:
© 2018

Keywords

Bio-imaging
Fluorescence imaging
Fluorophore
Membrane probe
Two-photon imaging

ASJC Scopus subject areas

General Chemical Engineering
Process Chemistry and Technology

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10.1016/j.dyepig.2018.10.016

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@article{94acbfaea9884c808b85735c11498cce,

title = "A wavelength-tunable and facilely functionable D-A type naphthalene core skeleton: Synthesis, photophysical property, and bio-imaging applications for cells and tissues",

abstract = "A new wavelength-tunable and facilely functionable electron donor (D)-acceptor (A) type fluorescent naphthalene core skeleton and its application for cell membrane imaging are reported. The core skeleton shows bright green fluorescence with aldehyde(–CHO) moiety at the electron acceptor site, and its emission wavelength is tuned to blue and red by introducing the moiety of nitrile (–CN) and dicyanovinyl (–CH(CN)2), respectively, at the acceptor site. In addition, the core skeleton can be readily functionable by introducing a targeting moiety at the extra hydroxyl group. For the first demonstration as a fluorescent probe, a long-chain carbon is introduced and evaluated its bio-imaging ability for the cellular membranes on cells and tissues by using confocal laser scanning microscopy (CLSM) and two-photon microscopy (TPM). The synthesis, photophysical property, and quantum chemical calculations are also identified.",

keywords = "Bio-imaging, Fluorescence imaging, Fluorophore, Membrane probe, Two-photon imaging",

author = "Yuna Jung and Youngseo Kim and Kim, {Na Hee} and Junho Lee and Kim, {Kang Hoon} and Junyang Jung and Youngbuhm Huh and Jang, {Hyeung Jin} and Jinmyoung Joo and Sungnam Park and Dokyoung Kim",

note = "Funding Information: This research was supported by the Bio & Medical Technology Development Program of the National Research Foundation (NRF) of Korea funded by the Ministry of Science & ICT (NRF-2018-M3A9H3021707). This research was also supported by Basic Science Research Program through the National Research Foundation (NRF) of Korea funded by the Ministry of Education (NRF-2018-R1A6A1A03025124, NRF-2018-R1D1A1B07043383, NRF-2017-R1D1A1B03035525). J. Joo thanks to the financial support (2018–7045) from the Asan Institute for Life Sciences, Asan Medical Center, Seoul, Korea. Funding Information: This research was supported by the Bio & Medical Technology Development Program of the National Research Foundation (NRF) of Korea funded by the Ministry of Science & ICT ( NRF-2018-M3A9H3021707 ). This research was also supported by Basic Science Research Program through the National Research Foundation (NRF) of Korea funded by the Ministry of Education ( NRF-2018-R1A6A1A03025124 , NRF-2018-R1D1A1B07043383 , NRF-2017-R1D1A1B03035525 ). J. Joo thanks to the financial support ( 2018–7045 ) from the Asan Institute for Life Sciences, Asan Medical Center, Seoul, Korea . Publisher Copyright: {\textcopyright} 2018",

year = "2019",

month = mar,

doi = "10.1016/j.dyepig.2018.10.016",

language = "English",

volume = "162",

pages = "104--111",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier B.V.",

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T1 - A wavelength-tunable and facilely functionable D-A type naphthalene core skeleton

T2 - Synthesis, photophysical property, and bio-imaging applications for cells and tissues

AU - Jung, Yuna

AU - Kim, Youngseo

AU - Kim, Na Hee

AU - Lee, Junho

AU - Kim, Kang Hoon

AU - Jung, Junyang

AU - Huh, Youngbuhm

AU - Jang, Hyeung Jin

AU - Joo, Jinmyoung

AU - Park, Sungnam

AU - Kim, Dokyoung

N1 - Funding Information: This research was supported by the Bio & Medical Technology Development Program of the National Research Foundation (NRF) of Korea funded by the Ministry of Science & ICT (NRF-2018-M3A9H3021707). This research was also supported by Basic Science Research Program through the National Research Foundation (NRF) of Korea funded by the Ministry of Education (NRF-2018-R1A6A1A03025124, NRF-2018-R1D1A1B07043383, NRF-2017-R1D1A1B03035525). J. Joo thanks to the financial support (2018–7045) from the Asan Institute for Life Sciences, Asan Medical Center, Seoul, Korea. Funding Information: This research was supported by the Bio & Medical Technology Development Program of the National Research Foundation (NRF) of Korea funded by the Ministry of Science & ICT ( NRF-2018-M3A9H3021707 ). This research was also supported by Basic Science Research Program through the National Research Foundation (NRF) of Korea funded by the Ministry of Education ( NRF-2018-R1A6A1A03025124 , NRF-2018-R1D1A1B07043383 , NRF-2017-R1D1A1B03035525 ). J. Joo thanks to the financial support ( 2018–7045 ) from the Asan Institute for Life Sciences, Asan Medical Center, Seoul, Korea . Publisher Copyright: © 2018

PY - 2019/3

Y1 - 2019/3

N2 - A new wavelength-tunable and facilely functionable electron donor (D)-acceptor (A) type fluorescent naphthalene core skeleton and its application for cell membrane imaging are reported. The core skeleton shows bright green fluorescence with aldehyde(–CHO) moiety at the electron acceptor site, and its emission wavelength is tuned to blue and red by introducing the moiety of nitrile (–CN) and dicyanovinyl (–CH(CN)2), respectively, at the acceptor site. In addition, the core skeleton can be readily functionable by introducing a targeting moiety at the extra hydroxyl group. For the first demonstration as a fluorescent probe, a long-chain carbon is introduced and evaluated its bio-imaging ability for the cellular membranes on cells and tissues by using confocal laser scanning microscopy (CLSM) and two-photon microscopy (TPM). The synthesis, photophysical property, and quantum chemical calculations are also identified.

AB - A new wavelength-tunable and facilely functionable electron donor (D)-acceptor (A) type fluorescent naphthalene core skeleton and its application for cell membrane imaging are reported. The core skeleton shows bright green fluorescence with aldehyde(–CHO) moiety at the electron acceptor site, and its emission wavelength is tuned to blue and red by introducing the moiety of nitrile (–CN) and dicyanovinyl (–CH(CN)2), respectively, at the acceptor site. In addition, the core skeleton can be readily functionable by introducing a targeting moiety at the extra hydroxyl group. For the first demonstration as a fluorescent probe, a long-chain carbon is introduced and evaluated its bio-imaging ability for the cellular membranes on cells and tissues by using confocal laser scanning microscopy (CLSM) and two-photon microscopy (TPM). The synthesis, photophysical property, and quantum chemical calculations are also identified.

KW - Bio-imaging

KW - Fluorescence imaging

KW - Fluorophore

KW - Membrane probe

KW - Two-photon imaging

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U2 - 10.1016/j.dyepig.2018.10.016

DO - 10.1016/j.dyepig.2018.10.016

M3 - Article

AN - SCOPUS:85054823300

SN - 0143-7208

VL - 162

SP - 104

EP - 111

JO - Dyes and Pigments

JF - Dyes and Pigments

ER -

A wavelength-tunable and facilely functionable D-A type naphthalene core skeleton: Synthesis, photophysical property, and bio-imaging applications for cells and tissues

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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