期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 2, 页码 1316-1322出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja210065g
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资金
- National Research Foundation of Korea [2011-0000420]
- WCU (World Class University) [R32-2010-000-10217-0]
- Ministry of Education, Science, and Technology (MEST)
- National Research Foundation of Korea [R32-2012-000-10217-0, R32-2010-000-10217-0, 2009-0081566] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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.
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