Hepatocyte-targeting single galactose-appended naphthalimide: A tool for intracellular thiol imaging in vivo
- Authors
- Lee, M.H.; Han, J.H.; Kwon, P.-S.; Bhuniya, S.; Kim, J.Y.; Sessler, J.L.; Kang, C.; Kim, J.S.
- Issue Date
- Jan-2012
- Publisher
- American Chemical Society
- Citation
- Journal of the American Chemical Society, v.134, no.2, pp 1316 - 1322
- Pages
- 7
- Journal Title
- Journal of the American Chemical Society
- Volume
- 134
- Number
- 2
- Start Page
- 1316
- End Page
- 1322
- URI
- https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/147657
- DOI
- 10.1021/ja210065g
- ISSN
- 0002-7863
1520-5126
- Abstract
- We present the design, synthesis, spectroscopic properties, and biological evaluation of a single galactose-appended naphthalimide (1). Probe 1 is a multifunctional molecule that incorporates a thiol-specific cleavable disulfide bond, a masked phthalamide fluorophore, and a single galactose moiety as a hepatocyte-targeting unit. It constitutes a new type of targetable ligand for hepatic thiol imaging in living cells and animals. Confocal microscopic imaging experiments reveal that 1, but not the galactose-free control system 2, is preferentially taken up by HepG2 cells through galactose-targeted, ASGP-R-mediated endocytosis. Probe 1 displays a fluorescence emission feature at 540 nm that is induced by exposure to free endogenous thiols, most notably GSH. The liver-specificity of 1 was confirmed in vivo via use of a rat model. The potential utility of this probe in indicating pathogenic states and as a possible screening tool for agents that can manipulate oxidative stress was demonstrated in experiments wherein palmitate was used to induce lipotoxicity in HepG2 cells. © 2011 American Chemical Society.
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