The DOI matches its Crossref record; 47 of the 47 references it cites were found in a registry or an index.
Hepatocyte-Targeting Single Galactose-Appended Naphthalimide: A Tool for Intracellular Thiol Imaging in Vivo
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.
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Metadata
- Authors
- Lee, M. H., Han, J. H., Kwon, P.-S., Bhuniya, S., Kim, J. Y., Sessler, J. L., Kang, C., & Kim, J. S.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-01-03
- Volume
- 134
- Issue
- 2
- Pages
- 1316-1322
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2003076361
- Cited by
- 408
- References
- 47
- FWCI
- 11.83
- Type
- journal article
- Language
- en
- Open access
- closed
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