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3 results on '"Carbene complexe"'

1. The effects of two gold-N-heterocyclic carbene (NHC) complexes in ovarian cancer cells: a redox proteomic study

Author

Lara Massai, Luigi Messori, Andrea Carpentieri, Angela Amoresano, Chiara Melchiorre, Tania Fiaschi, Alessandra Modesti, Tania Gamberi, Francesca Magherini, Massai, L., Messori, L., Carpentieri, A., Amoresano, A., Melchiorre, C., Fiaschi, T., Modesti, A., Gamberi, T., and Magherini, F.

Subjects
Pharmacology, Ovarian Neoplasms, Proteomics, Cancer Research, Redox proteomic, Antineoplastic Agents, Carbene complexe, Carcinoma, Ovarian Epithelial, Toxicology, Gold Compounds, Oncology, Coordination Complexes, Ovarian cancer, Cell Line, Tumor, Humans, Pharmacology (medical), Female, Gold, Methane, Oxidation-Reduction, Gold drug
Abstract

Purpose Ovarian cancer is the fifth leading cause of cancer-related deaths in women. Standard treatment consists of tumor debulking surgery followed by platinum and paclitaxel chemotherapy; yet, despite the initial response, about 70–75% of patients develop resistance to chemotherapy. Gold compounds represent a family of very promising anticancer drugs. Among them, we previously investigated the cytotoxic and pro-apoptotic properties of Au(NHC) and Au(NHC)2PF6, i.e., a monocarbene gold(I) complex and the corresponding bis(carbene) complex. Gold compounds are known to alter the redox state of cells interacting with free cysteine and selenocysteine residues of several proteins. Herein, a redox proteomic study has been carried out to elucidate the mechanisms of cytotoxicity in A2780 human ovarian cancer cells. Methods A biotinylated iodoacetamide labeling method coupled with mass spectrometry was used to identify oxidation-sensitive protein cysteines. Results Gold carbene complexes cause extensive oxidation of several cellular proteins; many affected proteins belong to two major functional classes: carbohydrate metabolism, and cytoskeleton organization/cell adhesion. Among the affected proteins, Glyceraldehyde-3-phosphate dehydrogenase inhibition was proved by enzymatic assays and by ESI–MS studies. We also found that Au(NHC)2PF6 inhibits mitochondrial respiration impairing complex I function. Concerning the oxidized cytoskeletal proteins, gold binding to the free cysteines of actin was demonstrated by ESI–MS analysis. Notably, both gold compounds affected cell migration and invasion. Conclusions In this study, we deepened the mode of action of Au(NHC) and Au(NHC)2PF6, identifying common cellular targets but confirming their different influence on the mitochondrial function.

Published
2022

2. Synthesis of the first chiral phosphorous chelate aminophosphino-carbene complex and its applications in stereoselective addition reactions

Author

Maiorana, S, Papagni, A, Licandro, E, Perdicchia, D, Baldoli, C, Graiff, C, Tiripicchio, A, PAPAGNI, ANTONIO, Tiripicchio, A., Maiorana, S, Papagni, A, Licandro, E, Perdicchia, D, Baldoli, C, Graiff, C, Tiripicchio, A, PAPAGNI, ANTONIO, and Tiripicchio, A.

Abstract

The first phosphorous chelate chiral aminophosphinomethyl carbene complex 5 has been synthesized. Its conjugated base represents a new chiral cr-unsubstituted amide enolate equivalent for stereoselective addition reactions. The structure of the major diastereoisomer of the aldol addition complex between 5 and pO(2)N-C6H4-CHO, solved by X-ray diffraction, shows that the (S)-enantiomer of the conjugated base of 5 reacts preferentially with the re face of the carbonyl function. (C) 1999 Elsevier Science S.A. All rights reserved

Published
1999

3. Synthesis of the first chiral phosphorous chelate aminophosphino-carbene complex and its applications in stereoselective addition reactions

Author

Antonio Tiripicchio, Emanuela Licandro, Dario Perdicchia, Stefano Maiorana, Claudia Graiff, Antonio Papagni, Clara Baldoli, Maiorana, S, Papagni, A, Licandro, E, Perdicchia, D, Baldoli, C, Graiff, C, and Tiripicchio, A

Subjects
Addition reaction, Chemistry, Stereochemistry, carbene complexe, Diastereomer, intramolecular phosphorous coordination, Conjugated system, Inorganic Chemistry, chemistry.chemical_compound, Aldol reaction, Amide, Polymer chemistry, Materials Chemistry, Stereoselectivity, Chelation, diastereoselective aldol addition, Physical and Theoretical Chemistry, Carbene
Abstract

The first phosphorous chelate chiral aminophosphinomethyl carbene complex 5 has been synthesized. Its conjugated base represents a new chiral cr-unsubstituted amide enolate equivalent for stereoselective addition reactions. The structure of the major diastereoisomer of the aldol addition complex between 5 and pO(2)N-C6H4-CHO, solved by X-ray diffraction, shows that the (S)-enantiomer of the conjugated base of 5 reacts preferentially with the re face of the carbonyl function. (C) 1999 Elsevier Science S.A. All rights reserved

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