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Article

When Chirality Makes the Difference: The Case of Novel Enantiopure N-Heterocyclic Carbene–Gold and –Silver Complexes

by
Maria Marra
1,†,
Annaluisa Mariconda
2,†,
Domenico Iacopetta
1,
Jessica Ceramella
1,*,
Assunta D’Amato
3,
Camillo Rosano
4,*,
Kateryna Tkachenko
4,
Michele Pellegrino
1,
Stefano Aquaro
5,
Maria Stefania Sinicropi
1,‡ and
Pasquale Longo
3,‡
1
Department of Pharmacy, Health and Nutritional Sciences, University of Calabria, Via P. Bucci, 87036 Arcavacata di Rende, Italy
2
Department of Science, University of Basilicata, Viale dell’Ateneo Lucano 10, 85100 Potenza, Italy
3
Department of Chemistry and Biology, University of Salerno, Via Giovanni Paolo II, 132, 84084 Fisciano, Italy
4
U.O. Proteomica e Spettrometria di Massa, IRCCS Ospedale Policlinico San Martino, L.go Rosanna Benzi 10, 16132 Genova, Italy
5
Department of Life, Health and Environmental Sciences, University of L’Aquila, Piazzale Salvatore Tommasi 1, Blocco 11, Coppito, 67010 L’Aquila, Italy
*
Authors to whom correspondence should be addressed.
†
These authors contributed equally to this work.
‡
These authors also contributed equally to this work.
Molecules 2024, 29(22), 5262; https://doi.org/10.3390/molecules29225262
Submission received: 29 September 2024 / Revised: 29 October 2024 / Accepted: 5 November 2024 / Published: 7 November 2024
(This article belongs to the Special Issue Chemistry and Health: Nitrogen Heterocycle Chemistry and Medicinal Chemistry)
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Abstract

N-heterocyclic carbene (NHC)–gold and –silver complexes have attracted the interest of the scientific community because of their multiple applications and their versatility in being chemically modified in order to improve their biological properties. However, most of these complexes contain one or more chiral centers, and have been obtained and studied as racemic mixture. In particular, concerning the interesting biological and medicinal properties, many questions about how the chirality may influence these properties still remain unanswered. Aiming at a better understanding, herein a series of enantiopure NHC–gold and –silver complexes was synthesized, characterized and biologically evaluated in different in vitro systems. The individuated complexes exerted different properties based on the complexed metal and the specific configuration, with the (R)-gold–NHC complexes being the most active, particularly as anti-inflammatory molecules. Docking simulations indicated a different binding mode for each enantiomer. Moreover, anticancer and antibacterial activities were also evaluated for the considered enantiomers. Overall, the reported data may contribute to a better understanding of the different biological properties exerted by the enantiopure gold and silver complexes.
Keywords: N-heterocyclic carbenes (NHC); enantiopure complexes; iNOS inhibition; anticancer; antibacterial N-heterocyclic carbenes (NHC); enantiopure complexes; iNOS inhibition; anticancer; antibacterial

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MDPI and ACS Style

Marra, M.; Mariconda, A.; Iacopetta, D.; Ceramella, J.; D’Amato, A.; Rosano, C.; Tkachenko, K.; Pellegrino, M.; Aquaro, S.; Sinicropi, M.S.; et al. When Chirality Makes the Difference: The Case of Novel Enantiopure N-Heterocyclic Carbene–Gold and –Silver Complexes. Molecules 2024, 29, 5262. https://doi.org/10.3390/molecules29225262

AMA Style

Marra M, Mariconda A, Iacopetta D, Ceramella J, D’Amato A, Rosano C, Tkachenko K, Pellegrino M, Aquaro S, Sinicropi MS, et al. When Chirality Makes the Difference: The Case of Novel Enantiopure N-Heterocyclic Carbene–Gold and –Silver Complexes. Molecules. 2024; 29(22):5262. https://doi.org/10.3390/molecules29225262

Chicago/Turabian Style

Marra, Maria, Annaluisa Mariconda, Domenico Iacopetta, Jessica Ceramella, Assunta D’Amato, Camillo Rosano, Kateryna Tkachenko, Michele Pellegrino, Stefano Aquaro, Maria Stefania Sinicropi, and et al. 2024. "When Chirality Makes the Difference: The Case of Novel Enantiopure N-Heterocyclic Carbene–Gold and –Silver Complexes" Molecules 29, no. 22: 5262. https://doi.org/10.3390/molecules29225262

APA Style

Marra, M., Mariconda, A., Iacopetta, D., Ceramella, J., D’Amato, A., Rosano, C., Tkachenko, K., Pellegrino, M., Aquaro, S., Sinicropi, M. S., & Longo, P. (2024). When Chirality Makes the Difference: The Case of Novel Enantiopure N-Heterocyclic Carbene–Gold and –Silver Complexes. Molecules, 29(22), 5262. https://doi.org/10.3390/molecules29225262

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