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A simple synthetic entryway into (N-heterocyclic carbene)gold-steroidyl complexes and their anticancer activity

Thomas Scattolin (UGent) , Petra Lippmann, Marek Beliš (UGent) , Kristof Van Hecke (UGent) , Ingo Ott and Steven Nolan (UGent)
(2024) APPLIED ORGANOMETALLIC CHEMISTRY. 38(10).
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Abstract
A straightforward synthetic route to new N-heterocyclic carbene (NHC)-gold-steroidyl complexes is reported. The desired complexes were obtained using a weak base (such as K2CO3) through a concerted-metallation-deprotonation (CMD) reaction mechanism occurring between [Au(NHC)Cl] and ethisterone as a model steroid-based alkyne. Most complexes displayed good cytotoxicity against a panel of cancer cell lines with IC50 values in the low micromolar range. Cellular uptake of the most active complex 2a into MCF-7 breast cancer cells was facilitated by the coordinated ethisterone ligand.
Keywords
anticancer activity, gold-acetylide complexes, N-heterocyclic carbene ligands, steroids, weak base route, N-HETEROCYCLIC CARBENE, NHC, ROUTES

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Citation

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MLA
Scattolin, Thomas, et al. “A Simple Synthetic Entryway into (N-Heterocyclic Carbene)Gold-Steroidyl Complexes and Their Anticancer Activity.” APPLIED ORGANOMETALLIC CHEMISTRY, vol. 38, no. 10, 2024, doi:10.1002/aoc.6624.
APA
Scattolin, T., Lippmann, P., Beliš, M., Van Hecke, K., Ott, I., & Nolan, S. (2024). A simple synthetic entryway into (N-heterocyclic carbene)gold-steroidyl complexes and their anticancer activity. APPLIED ORGANOMETALLIC CHEMISTRY, 38(10). https://doi.org/10.1002/aoc.6624
Chicago author-date
Scattolin, Thomas, Petra Lippmann, Marek Beliš, Kristof Van Hecke, Ingo Ott, and Steven Nolan. 2024. “A Simple Synthetic Entryway into (N-Heterocyclic Carbene)Gold-Steroidyl Complexes and Their Anticancer Activity.” APPLIED ORGANOMETALLIC CHEMISTRY 38 (10). https://doi.org/10.1002/aoc.6624.
Chicago author-date (all authors)
Scattolin, Thomas, Petra Lippmann, Marek Beliš, Kristof Van Hecke, Ingo Ott, and Steven Nolan. 2024. “A Simple Synthetic Entryway into (N-Heterocyclic Carbene)Gold-Steroidyl Complexes and Their Anticancer Activity.” APPLIED ORGANOMETALLIC CHEMISTRY 38 (10). doi:10.1002/aoc.6624.
Vancouver
1.
Scattolin T, Lippmann P, Beliš M, Van Hecke K, Ott I, Nolan S. A simple synthetic entryway into (N-heterocyclic carbene)gold-steroidyl complexes and their anticancer activity. APPLIED ORGANOMETALLIC CHEMISTRY. 2024;38(10).
IEEE
[1]
T. Scattolin, P. Lippmann, M. Beliš, K. Van Hecke, I. Ott, and S. Nolan, “A simple synthetic entryway into (N-heterocyclic carbene)gold-steroidyl complexes and their anticancer activity,” APPLIED ORGANOMETALLIC CHEMISTRY, vol. 38, no. 10, 2024.
@article{8748295,
  abstract     = {{A straightforward synthetic route to new N-heterocyclic carbene (NHC)-gold-steroidyl complexes is reported. The desired complexes were obtained using a weak base (such as K2CO3) through a concerted-metallation-deprotonation (CMD) reaction mechanism occurring between [Au(NHC)Cl] and ethisterone as a model steroid-based alkyne. Most complexes displayed good cytotoxicity against a panel of cancer cell lines with IC50 values in the low micromolar range. Cellular uptake of the most active complex 2a into MCF-7 breast cancer cells was facilitated by the coordinated ethisterone ligand.}},
  articleno    = {{e6624}},
  author       = {{Scattolin, Thomas and Lippmann, Petra and Beliš, Marek and Van Hecke, Kristof and Ott, Ingo and Nolan, Steven}},
  issn         = {{0268-2605}},
  journal      = {{APPLIED ORGANOMETALLIC CHEMISTRY}},
  keywords     = {{anticancer activity,gold-acetylide complexes,N-heterocyclic carbene ligands,steroids,weak base route,N-HETEROCYCLIC CARBENE,NHC,ROUTES}},
  language     = {{eng}},
  number       = {{10}},
  pages        = {{9}},
  title        = {{A simple synthetic entryway into (N-heterocyclic carbene)gold-steroidyl complexes and their anticancer activity}},
  url          = {{http://doi.org/10.1002/aoc.6624}},
  volume       = {{38}},
  year         = {{2024}},
}
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