Rational Design of Palladium(II) Indenyl and Allyl Complexes Bearing Phosphine and Isocyanide Ancillary Ligands with Promising Antitumor Activity
A new class of palladium–indenyl complexes characterized by the presence of one bulky alkyl isocyanide and one aryl phosphine serving as ancillary ligands has been prepared, presenting high yields and selectivity. All the new products were completely characterized using spectroscopic and spectrometr...
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MDPI AG
2024-01-01
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| Online Access: | https://www.mdpi.com/1420-3049/29/2/345 |
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| author | Enrica Bortolamiol Eleonora Botter Enrico Cavarzerani Matteo Mauceri Nicola Demitri Flavio Rizzolio Fabiano Visentin Thomas Scattolin |
| author_facet | Enrica Bortolamiol Eleonora Botter Enrico Cavarzerani Matteo Mauceri Nicola Demitri Flavio Rizzolio Fabiano Visentin Thomas Scattolin |
| author_sort | Enrica Bortolamiol |
| collection | DOAJ |
| description | A new class of palladium–indenyl complexes characterized by the presence of one bulky alkyl isocyanide and one aryl phosphine serving as ancillary ligands has been prepared, presenting high yields and selectivity. All the new products were completely characterized using spectroscopic and spectrometric techniques (NMR, FT-IR, and HRMS), and, for most of them, it was also possible to define their solid-state structures via X-ray diffractometry, revealing that the indenyl fragment always binds to the metal centre with a hapticity intermediate between ƞ<sup>3</sup> and ƞ<sup>5</sup>. A reactivity study carried out using piperidine as a nucleophilic agent proved that the indenyl moiety is the eligible site of attack rather than the isocyanide ligand or the metal centre. All complexes were tested as potential anticancer agents against three ovarian cancer cell lines (A2780, A2780<i>cis</i>, and OVCAR-5) and one breast cancer cell line (MDA-MB-231), displaying comparable activity with respect to cisplatin, which was used as a positive control. Moreover, the similar cytotoxicity observed towards A2780 and A2780<i>cis</i> cells (cisplatin-sensitive and cisplatin-resistant, respectively) suggests that our palladium derivatives presumably act with a mechanism of action different than that of the clinically approved platinum drugs. For comparison, we also synthesized Pd-ƞ<sup>3</sup>-allyl derivatives, which generally showed a slightly higher activity towards ovarian cancer cells and lower activity towards breast cancer cells with respect to their Pd-indenyl congeners. |
| first_indexed | 2024-03-08T09:49:30Z |
| format | Article |
| id | doaj.art-39419906a8464228a47a159993887713 |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-08T09:49:30Z |
| publishDate | 2024-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-39419906a8464228a47a1599938877132024-01-29T14:07:43ZengMDPI AGMolecules1420-30492024-01-0129234510.3390/molecules29020345Rational Design of Palladium(II) Indenyl and Allyl Complexes Bearing Phosphine and Isocyanide Ancillary Ligands with Promising Antitumor ActivityEnrica Bortolamiol0Eleonora Botter1Enrico Cavarzerani2Matteo Mauceri3Nicola Demitri4Flavio Rizzolio5Fabiano Visentin6Thomas Scattolin7Department of Molecular Sciences and Nanosystems, Università Ca’ Foscari, Campus Scientifico, Via Torino 155, 30174 Venezia, ItalyDepartment of Molecular Sciences and Nanosystems, Università Ca’ Foscari, Campus Scientifico, Via Torino 155, 30174 Venezia, ItalyDepartment of Molecular Sciences and Nanosystems, Università Ca’ Foscari, Campus Scientifico, Via Torino 155, 30174 Venezia, ItalyDepartment of Molecular Sciences and Nanosystems, Università Ca’ Foscari, Campus Scientifico, Via Torino 155, 30174 Venezia, ItalyElettra-Sincrotrone Trieste, Area Science Park, S.S. 14 Km 163.5 Basovizza, 34149 Trieste, ItalyDepartment of Molecular Sciences and Nanosystems, Università Ca’ Foscari, Campus Scientifico, Via Torino 155, 30174 Venezia, ItalyDepartment of Molecular Sciences and Nanosystems, Università Ca’ Foscari, Campus Scientifico, Via Torino 155, 30174 Venezia, ItalyDipartimento di Scienze Chimiche, Università Degli Studi di Padova, Via Marzolo 1, 35131 Padova, ItalyA new class of palladium–indenyl complexes characterized by the presence of one bulky alkyl isocyanide and one aryl phosphine serving as ancillary ligands has been prepared, presenting high yields and selectivity. All the new products were completely characterized using spectroscopic and spectrometric techniques (NMR, FT-IR, and HRMS), and, for most of them, it was also possible to define their solid-state structures via X-ray diffractometry, revealing that the indenyl fragment always binds to the metal centre with a hapticity intermediate between ƞ<sup>3</sup> and ƞ<sup>5</sup>. A reactivity study carried out using piperidine as a nucleophilic agent proved that the indenyl moiety is the eligible site of attack rather than the isocyanide ligand or the metal centre. All complexes were tested as potential anticancer agents against three ovarian cancer cell lines (A2780, A2780<i>cis</i>, and OVCAR-5) and one breast cancer cell line (MDA-MB-231), displaying comparable activity with respect to cisplatin, which was used as a positive control. Moreover, the similar cytotoxicity observed towards A2780 and A2780<i>cis</i> cells (cisplatin-sensitive and cisplatin-resistant, respectively) suggests that our palladium derivatives presumably act with a mechanism of action different than that of the clinically approved platinum drugs. For comparison, we also synthesized Pd-ƞ<sup>3</sup>-allyl derivatives, which generally showed a slightly higher activity towards ovarian cancer cells and lower activity towards breast cancer cells with respect to their Pd-indenyl congeners.https://www.mdpi.com/1420-3049/29/2/345palladium indenyl complexesphosphine ligandsisocyanide ligandsmetallodrugsantitumor activityovarian cancer |
| spellingShingle | Enrica Bortolamiol Eleonora Botter Enrico Cavarzerani Matteo Mauceri Nicola Demitri Flavio Rizzolio Fabiano Visentin Thomas Scattolin Rational Design of Palladium(II) Indenyl and Allyl Complexes Bearing Phosphine and Isocyanide Ancillary Ligands with Promising Antitumor Activity Molecules palladium indenyl complexes phosphine ligands isocyanide ligands metallodrugs antitumor activity ovarian cancer |
| title | Rational Design of Palladium(II) Indenyl and Allyl Complexes Bearing Phosphine and Isocyanide Ancillary Ligands with Promising Antitumor Activity |
| title_full | Rational Design of Palladium(II) Indenyl and Allyl Complexes Bearing Phosphine and Isocyanide Ancillary Ligands with Promising Antitumor Activity |
| title_fullStr | Rational Design of Palladium(II) Indenyl and Allyl Complexes Bearing Phosphine and Isocyanide Ancillary Ligands with Promising Antitumor Activity |
| title_full_unstemmed | Rational Design of Palladium(II) Indenyl and Allyl Complexes Bearing Phosphine and Isocyanide Ancillary Ligands with Promising Antitumor Activity |
| title_short | Rational Design of Palladium(II) Indenyl and Allyl Complexes Bearing Phosphine and Isocyanide Ancillary Ligands with Promising Antitumor Activity |
| title_sort | rational design of palladium ii indenyl and allyl complexes bearing phosphine and isocyanide ancillary ligands with promising antitumor activity |
| topic | palladium indenyl complexes phosphine ligands isocyanide ligands metallodrugs antitumor activity ovarian cancer |
| url | https://www.mdpi.com/1420-3049/29/2/345 |
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