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J Photochem Photobiol B. 2017 Jan;166:52-57. doi: 10.1016/j.jphotobiol.2016.11.009. Epub 2016 Nov 12.

Live bio-imaging with fully bio-compatible organic fluorophores.

Author information

1
Department of Chemistry, Seoul National University, Seoul 151-747, Republic of Korea.
2
Department of Biophysics and Chemical Biology, Seoul National University, Seoul 151-747, Republic of Korea.
3
College of Pharmacy, Dongguk University, Goyang, Gyeonggi-do 410-820, Republic of Korea.
4
School of Medicine, Yale University, New Haven, CT 06511, USA.
5
Department of Chemistry, Seoul National University, Seoul 151-747, Republic of Korea; Department of Biophysics and Chemical Biology, Seoul National University, Seoul 151-747, Republic of Korea. Electronic address: seongkim@snu.ac.kr.

Abstract

We synthesized a new organic fluorescent dye named resveratrone glucoside from the photoreaction of naturally-occurring phytoalexin compound resveratrol glucoside (resveratrol-3-β-mono-d-glucoside), which is abundant in various plants such as berries, herbs, nuts and grapes. Just like its predecessor molecule resveratrone that was previously discovered by our group, resveratrone glucoside possesses excellent optical properties including a high fluorescence quantum yield, a large Stokes' shift, and a large two-photon absorption cross section. In addition to these highly desirable properties, both fluorescent molecules can also be used as ideal bio-compatible organic fluorophores since they have remarkably low cytotoxicity, which we verified through our cell morphological study, trypan blue exclusion assay, Western blot analysis and fluorescence imaging of various live biological specimens. In particular, we note that resveratrone glucoside is much more soluble in aqueous solution because of its glycosidic side chain and therefore highly suitable for in vivo imaging. We demonstrated that resveratrone and resveratrone glucoside can be used in one- and two-photon fluorescence microscopic imaging of E. coli, yeast (S. cerevisiae), and mammalian cell lines including HeLa and MCF10A cells as well as to the live imaging and real-time tracking of the zebrafish embryo development. Both organic fluorophores can be readily obtained from a simple photoreaction of commercially available, inexpensive samples.

[Indexed for MEDLINE]

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