The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.
Gold(I) Carbene Complexes Causing Thioredoxin 1 and Thioredoxin 2 Oxidation as Potential Anticancer Agents
Abstract
Gold(I) complexes with 1,3-substituted imidazole-2-ylidene and benzimidazole-2-ylidene ligands of the type NHC-Au-L (NHC = N-heterocyclic carbene L = Cl or 2-mercapto-pyrimidine) have been synthesized and structurally characterized. The compounds were evaluated for their antiproliferative properties in human ovarian cancer cells sensitive and resistant to cisplatin (A2780S/R), as well in the nontumorigenic human embryonic kidney cell line (HEK-293T), showing in some cases important cytotoxic effects. Some of the complexes were comparatively tested as thioredoxin reductase (TrxR) and glutathione reductase (GR) inhibitors, directly against the purified proteins or in cell extracts. The compounds showed potent and selective TrxR inhibition properties in particular in cancer cell lines. Remarkably, the most effective TrxR inhibitors induced extensive oxidation of thioredoxins (Trxs), which was more relevant in the cancerous cells than in HEK-293T cells. Additional biochemical assays on glutathione systems and reactive oxygen species formation evidenced important differences with respect to the classical cytotoxic Au(I)-phosphine compound auranofin.
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Cites
OLEX2 : a complete structure solution, refinement and analysis program
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., & Puschmann, H. (2009) · Journal of Applied Crystallography · doi:10.1107/s0021889808042726 · Cited by 32,811
Thioredoxin and Related Molecules–From Biology to Health and Disease
Lillig, C. H., & Holmgren, A. (2007) · Antioxidants & Redox Signaling · doi:10.1089/ars.2007.9.25 · Cited by 724
Thioredoxin Reductase Is Irreversibly Modified by Curcumin
Fang, J., Lu, J., & Holmgren, A. (2005) · Journal of Biological Chemistry · doi:10.1074/jbc.m414645200 · Cited by 521
Cited by
N-Heterocyclic carbene metal complexes in medicinal chemistry
Oehninger, L., Rubbiani, R., & Ott, I. (2013) · Dalton Trans. · doi:10.1039/c2dt32617e · Cited by 560
Bertrand, B., & Casini, A. (2014) · Dalton Trans. · doi:10.1039/c3dt52524d · Cited by 441
Self-citationHighly Selective Off–On Fluorescent Probe for Imaging Thioredoxin Reductase in Living Cells
Zhang, L., Duan, D., Liu, Y., Ge, C., Cui, X., Sun, J., & Fang, J. (2014) · Journal of the American Chemical Society · doi:10.1021/ja408792k · Cited by 254
Metadata
- Authors
- Schuh, E., Pflüger, C., Citta, A., Folda, A., Rigobello, M. P., Bindoli, A., Casini, A., & Mohr, F.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-06-04
- Volume
- 55
- Issue
- 11
- Pages
- 5518-5528
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2160782716
- Cited by
- 246
- References
- 3
- FWCI
- 11.08
- Type
- journal article
- Language
- en
- Open access
- closed
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