When Chirality Makes the Difference: The Case of Novel Enantiopure <i>N</i>-Heterocyclic Carbene–Gold and –Silver Complexes
<i>N</i>-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 complex...
Saved in:
| Main Authors: | , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2024-11-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/29/22/5262 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1846152853937192960 |
|---|---|
| author | Maria Marra Annaluisa Mariconda Domenico Iacopetta Jessica Ceramella Assunta D’Amato Camillo Rosano Kateryna Tkachenko Michele Pellegrino Stefano Aquaro Maria Stefania Sinicropi Pasquale Longo |
| author_facet | Maria Marra Annaluisa Mariconda Domenico Iacopetta Jessica Ceramella Assunta D’Amato Camillo Rosano Kateryna Tkachenko Michele Pellegrino Stefano Aquaro Maria Stefania Sinicropi Pasquale Longo |
| author_sort | Maria Marra |
| collection | DOAJ |
| description | <i>N</i>-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 (<i>R</i>)-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. |
| format | Article |
| id | doaj-art-67b99db78f124b0a9098662b5214a096 |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-67b99db78f124b0a9098662b5214a0962024-11-26T18:15:20ZengMDPI AGMolecules1420-30492024-11-012922526210.3390/molecules29225262When Chirality Makes the Difference: The Case of Novel Enantiopure <i>N</i>-Heterocyclic Carbene–Gold and –Silver ComplexesMaria Marra0Annaluisa Mariconda1Domenico Iacopetta2Jessica Ceramella3Assunta D’Amato4Camillo Rosano5Kateryna Tkachenko6Michele Pellegrino7Stefano Aquaro8Maria Stefania Sinicropi9Pasquale Longo10Department of Pharmacy, Health and Nutritional Sciences, University of Calabria, Via P. Bucci, 87036 Arcavacata di Rende, ItalyDepartment of Science, University of Basilicata, Viale dell’Ateneo Lucano 10, 85100 Potenza, ItalyDepartment of Pharmacy, Health and Nutritional Sciences, University of Calabria, Via P. Bucci, 87036 Arcavacata di Rende, ItalyDepartment of Pharmacy, Health and Nutritional Sciences, University of Calabria, Via P. Bucci, 87036 Arcavacata di Rende, ItalyDepartment of Chemistry and Biology, University of Salerno, Via Giovanni Paolo II, 132, 84084 Fisciano, ItalyU.O. Proteomica e Spettrometria di Massa, IRCCS Ospedale Policlinico San Martino, L.go Rosanna Benzi 10, 16132 Genova, ItalyU.O. Proteomica e Spettrometria di Massa, IRCCS Ospedale Policlinico San Martino, L.go Rosanna Benzi 10, 16132 Genova, ItalyDepartment of Pharmacy, Health and Nutritional Sciences, University of Calabria, Via P. Bucci, 87036 Arcavacata di Rende, ItalyDepartment of Life, Health and Environmental Sciences, University of L’Aquila, Piazzale Salvatore Tommasi 1, Blocco 11, Coppito, 67010 L’Aquila, ItalyDepartment of Pharmacy, Health and Nutritional Sciences, University of Calabria, Via P. Bucci, 87036 Arcavacata di Rende, ItalyDepartment of Chemistry and Biology, University of Salerno, Via Giovanni Paolo II, 132, 84084 Fisciano, Italy<i>N</i>-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 (<i>R</i>)-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.https://www.mdpi.com/1420-3049/29/22/5262<i>N</i>-heterocyclic carbenes (NHC)enantiopure complexesiNOS inhibitionanticancerantibacterial |
| spellingShingle | Maria Marra Annaluisa Mariconda Domenico Iacopetta Jessica Ceramella Assunta D’Amato Camillo Rosano Kateryna Tkachenko Michele Pellegrino Stefano Aquaro Maria Stefania Sinicropi Pasquale Longo When Chirality Makes the Difference: The Case of Novel Enantiopure <i>N</i>-Heterocyclic Carbene–Gold and –Silver Complexes Molecules <i>N</i>-heterocyclic carbenes (NHC) enantiopure complexes iNOS inhibition anticancer antibacterial |
| title | When Chirality Makes the Difference: The Case of Novel Enantiopure <i>N</i>-Heterocyclic Carbene–Gold and –Silver Complexes |
| title_full | When Chirality Makes the Difference: The Case of Novel Enantiopure <i>N</i>-Heterocyclic Carbene–Gold and –Silver Complexes |
| title_fullStr | When Chirality Makes the Difference: The Case of Novel Enantiopure <i>N</i>-Heterocyclic Carbene–Gold and –Silver Complexes |
| title_full_unstemmed | When Chirality Makes the Difference: The Case of Novel Enantiopure <i>N</i>-Heterocyclic Carbene–Gold and –Silver Complexes |
| title_short | When Chirality Makes the Difference: The Case of Novel Enantiopure <i>N</i>-Heterocyclic Carbene–Gold and –Silver Complexes |
| title_sort | when chirality makes the difference the case of novel enantiopure i n i heterocyclic carbene gold and silver complexes |
| topic | <i>N</i>-heterocyclic carbenes (NHC) enantiopure complexes iNOS inhibition anticancer antibacterial |
| url | https://www.mdpi.com/1420-3049/29/22/5262 |
| work_keys_str_mv | AT mariamarra whenchiralitymakesthedifferencethecaseofnovelenantiopureiniheterocycliccarbenegoldandsilvercomplexes AT annaluisamariconda whenchiralitymakesthedifferencethecaseofnovelenantiopureiniheterocycliccarbenegoldandsilvercomplexes AT domenicoiacopetta whenchiralitymakesthedifferencethecaseofnovelenantiopureiniheterocycliccarbenegoldandsilvercomplexes AT jessicaceramella whenchiralitymakesthedifferencethecaseofnovelenantiopureiniheterocycliccarbenegoldandsilvercomplexes AT assuntadamato whenchiralitymakesthedifferencethecaseofnovelenantiopureiniheterocycliccarbenegoldandsilvercomplexes AT camillorosano whenchiralitymakesthedifferencethecaseofnovelenantiopureiniheterocycliccarbenegoldandsilvercomplexes AT katerynatkachenko whenchiralitymakesthedifferencethecaseofnovelenantiopureiniheterocycliccarbenegoldandsilvercomplexes AT michelepellegrino whenchiralitymakesthedifferencethecaseofnovelenantiopureiniheterocycliccarbenegoldandsilvercomplexes AT stefanoaquaro whenchiralitymakesthedifferencethecaseofnovelenantiopureiniheterocycliccarbenegoldandsilvercomplexes AT mariastefaniasinicropi whenchiralitymakesthedifferencethecaseofnovelenantiopureiniheterocycliccarbenegoldandsilvercomplexes AT pasqualelongo whenchiralitymakesthedifferencethecaseofnovelenantiopureiniheterocycliccarbenegoldandsilvercomplexes |