Synthesis, characterization, and anticancer activity of ferrocenyl complexes bearing different organopalladium fragments

Scattolin, Thomas; Moro, Giulia; Serena, Anita; Pattaro, Alessia Guadagnin; Rizzolio, Flavio; Canzonieri, Vincenzo; Demitri, Nicola; Bortolamiol, Enrica; Moretto, Ligia Maria; Visentin, Fabiano

doi:10.1002/aoc.6629

Cited by 3 publications

(6 citation statements)

References 85 publications

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“…The main drawback of palladium complexes is the rapid hydrolysis in aqueous medium compared with platinum derivatives. A good solution to this problem is the use of ligands firmly anchored to the metal center, and, among these, organopalladium derivatives, by virtue of the presence of at least one strong Pd–C bond, have so far provided the best results . In this context, Scattolin and Visentin have recently described the remarkable cytotoxicity of cationic NHC-Pd(II)-η 3 -allyl complexes .…”

Section: Biologically Active Metal-n-heterocyclic Carbene Complexesmentioning

confidence: 99%

Advances in the Synthesis and Applications of N-Heterocyclic Carbene Metal Complexes with a Focus on the Weak Base Route

Scattolin,

Logvinov,

Tzouras

et al. 2023

Organometallics

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N-heterocyclic carbene (NHC) ligands have evolved from being simple lab curiosities to tertiary phosphine mimics to finally take center stage as unique supporting ligands in organometallic chemistry, homogeneous catalysis, and more recently in medicinal chemistry and materials science applications. Some of these aspects are presented here from a perspective of researchers that have been fascinated by the area for quite some time.

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Section: Biologically Active Metal-n-heterocyclic Carbene Complexesmentioning

confidence: 99%

Advances in the Synthesis and Applications of N-Heterocyclic Carbene Metal Complexes with a Focus on the Weak Base Route

Scattolin,

Logvinov,

Tzouras

et al. 2023

Organometallics

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“…Also our group has been involved in this topic, preparing and testing as anticancer agents, a large number of organopalladium complexes. The organometallic motifs by us so far examined included Pd(II)-allyls, [21][22][23][24][25][26][27] palladacyclopentadienyls, [27,28,29] Pd(0)-olefins [27,30] and more recently Pd(II)-indenyls, [31][32][33] while other research groups turned their attention to Pd(II)-alkynyls [34] and an extensive panel of cyclopalladates. [19,[35][36][37][38] All these works indicate the primary importance of the organic fragment in determining the activity of the complex although it can be modulated by a careful choice of the ancillary ligands.…”

Section: Introductionmentioning

confidence: 99%

“…Our research group has recently proposed a systematic study of the antiproliferative activity towards ovarian cancer cells of different organopalladium derivatives coordinating dppf, obtaining interesting responses. [27] Ultimately, the aim of this work is the preparation of a series of new Pd-imidoyl complexes coordinating PTA, DAPTA and dppf, with a preliminary study of their antiproliferative and proapoptotic activity towards ovarian cancer cells.…”

Section: Introductionmentioning

confidence: 99%

“…Derivatives of this popular organometallic function have been extensively studied as antibacterial, antifungal and anticancer agents, [53–56] and therefore the coordination of the chelating dppf to a transition metal centre allows obtaining bimetallic systems with a possible synergic effect. Our research group has recently proposed a systematic study of the antiproliferative activity towards ovarian cancer cells of different organopalladium derivatives coordinating dppf, obtaining interesting responses [27] …”

Section: Introductionmentioning

confidence: 99%

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Palladium(II)‐Imidoyl Complexes: A New Piece in the Puzzle of Organopalladium Anticancer Agents

Bortolamiol,

Novaselich,

Tupini

et al. 2024

Eur J Inorg Chem

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Oursearch of new organopalladium compounds able to promote an effective antiproliferative action towards ovarian cancer cells continues. In this paper we have examined for the first time the anticancer activity of palladium imidoyl complexes, for which two different types of phosphines have been chosen as ancillary ligands: i) PTA and DAPTA to take advantage from their solubility in aqueous environment, and ii) dppf for combining the action of the Pd‐imidoyl fragment with that, well‐known, of ferrocene. The synthetic protocols as well as the exhaustive characterisation of the complexes through spectroscopic and diffractometric methods are described. In vitro tests carried out to assess the cytotoxicity of the new compounds towards two ovarian cancer cell lines (one cisplatin sensitive and the other cisplatin resistant) have revealed an interesting effect of the halide coordinated to the palladium centre (halogen effect). Moreover, all complexes have shown the same activity against the cisplatin‐sensitive (A2780) and cisplatin‐resistant (A2780cis) cell lines, suggesting different modes of action with respect to the “classical” platinum‐based drugs. Finally, a selection of the most active compounds has shown some selectivity towards ovarian cancer cells.

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“…To date, no study has been reported in the literature about the biological properties of palladium complexes equipped with tertiary alkyl isocyanides [ 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 ], and our choice to test the anticancer activity of Pd(II)-indenyl and Pd(II)-allyl complexes supported by these kinds of ligands is intended to begin filling this gap.…”

Section: Introductionmentioning

confidence: 99%

Rational Design of Palladium(II) Indenyl and Allyl Complexes Bearing Phosphine and Isocyanide Ancillary Ligands with Promising Antitumor Activity

Bortolamiol,

Botter,

Cavarzerani

et al. 2024

Molecules

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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 ƞ3 and ƞ5. 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, A2780cis, 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 A2780cis 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-ƞ3-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.

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Synthesis, characterization, and anticancer activity of ferrocenyl complexes bearing different organopalladium fragments

Cited by 3 publications

References 85 publications

Advances in the Synthesis and Applications of N-Heterocyclic Carbene Metal Complexes with a Focus on the Weak Base Route

Advances in the Synthesis and Applications of N-Heterocyclic Carbene Metal Complexes with a Focus on the Weak Base Route

Palladium(II)‐Imidoyl Complexes: A New Piece in the Puzzle of Organopalladium Anticancer Agents

Rational Design of Palladium(II) Indenyl and Allyl Complexes Bearing Phosphine and Isocyanide Ancillary Ligands with Promising Antitumor Activity

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