The DOI matches its Crossref record; 6 of the 6 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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Cites
Neurodegenerative diseases and oxidative stress
Barnham, K. J., Masters, C. L., & Bush, A. I. (2004) · Nature Reviews Drug Discovery · doi:10.1038/nrd1330 · Cited by 3,683
Reactive oxygen species have a causal role in multiple forms of insulin resistance
Houstis, N., Rosen, E. D., & Lander, E. S. (2006) · Nature · doi:10.1038/nature04634 · Cited by 2,525
Carbohydrate-Specific Receptors of the Liver
Ashwell, G., & Harford, J. (1982) · Annual Review of Biochemistry · doi:10.1146/annurev.bi.51.070182.002531 · Cited by 1,914
Fluorescent and colorimetric probes for detection of thiols
Chen, X., Zhou, Y., Peng, X., & Yoon, J. (2010) · Chemical Society Reviews · doi:10.1039/b925092a · Cited by 1,580
The common biology of cancer and ageing
Finkel, T., Serrano, M., & Blasco, M. A. (2007) · Nature · doi:10.1038/nature05985 · Cited by 988
Lee, Y. C., Townsend, R. R., Hardy, M. R., Lönngren, J., Arnarp, J., Haraldsson, M., & Lönn, H. (1983) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)33240-x · Cited by 503
Cited by
Small molecule-based ratiometric fluorescence probes for cations, anions, and biomolecules
Lee, M. H., Kim, J. S., & Sessler, J. L. (2015) · Chemical Society Reviews · doi:10.1039/c4cs00280f · Cited by 1,642
Self-citationDesign strategies of fluorescent probes for selective detection among biothiols
Niu, L.-Y., Chen, Y.-Z., Zheng, H.-R., Wu, L.-Z., Tung, C.-H., & Yang, Q.-Z. (2015) · Chemical Society Reviews · doi:10.1039/c5cs00152h · Cited by 870
Activatable Photosensitizers: Agents for Selective Photodynamic Therapy
Li, X., Kolemen, S., Yoon, J., & Akkaya, E. U. (2017) · Advanced Functional Materials · doi:10.1002/adfm.201604053 · Cited by 544
Chen, X., Xu, C., Wang, T., Zhou, C., Du, J., Wang, Z., Xu, H., Xie, T., Bi, G., Jiang, J., et al. (2016) · Angewandte Chemie International Edition · doi:10.1002/anie.201601252 · Cited by 445
Lee, M. H., Kim, J. Y., Han, J. H., Bhuniya, S., Sessler, J. L., Kang, C., & Kim, J. S. (2012) · Journal of the American Chemical Society · doi:10.1021/ja303998y · Cited by 309
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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
- 6
- FWCI
- 11.83
- Type
- journal article
- Language
- en
- Open access
- closed
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- Lee, M. H., Han, J. H., Kwon, P.-S., Bhuniya, S., Kim, J. Y., Sessler, J. L., Kang, C., & Kim, J. S. (2012). Hepatocyte-Targeting Single Galactose-Appended Naphthalimide: A Tool for Intracellular Thiol Imaging in Vivo. Journal of the American Chemical Society. https://doi.org/10.1021/ja210065g
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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