Cationic palladium(<scp>ii</scp>)-indenyl complexes bearing phosphines as ancillary ligands: synthesis, and study of indenyl amination and anticancer activity

Bortolamiol, Enrica; Fama, Francesco; Zhang, Ziyun; Demitri, Nicola; Cavallo, Luigi; Caligiuri, Isabella; Rizzolio, Flavio; Scattolin, Thomas; Visentin, Fabiano

doi:10.1039/d2dt01821g

Cited by 9 publications

(28 citation statements)

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“…In this context, we have recently reported the first systematic study dealing with the reactivity and antitumor activity of a large library of palladium(II) indenyl complexes bearing monodentate or bidentate phosphine ligands, showing the significant influence of steric and electronic parameters of the employed phosphines on the behaviour of the target organopalladium compounds. [8] We believe that the interesting biological results exposed in our first contribution can be a good starting point to make targeted changes in the coordinative sphere of palladium in order to improve the anticancer properties of Pd(II)-indenyl complexes. For this purpose, in this paper we have prepared a selection of palladium(II) indenyl complexes coordinating one phosphine and one N-heterocyclic carbene ligand.…”

Section: Introductionmentioning

confidence: 83%

“…More specifically, they have proven to be efficient antiproliferative agents towards three different ovarian cancer cell lines, with IC 50 values always within the micro/nano-molar range, showing slightly better performances than palladium(II) indenyl complexes bearing two phosphine ligands previously studied. [8] The cytotoxicity seems to moderately depend on the type of the phosphine ligand with the lowest activity in the case of PTA derivatives and the highest for the complex bearing P(OEt) 3 . Moreover, it should be emphasized that the antiproliferative activity of all complexes is practically the same towards A2780 (cisplatin-sensitive) and A2780cis (cisplatin-resistant) cells, suggesting a mechanism of action different from that of platinum-based drugs.…”

Section: Entrymentioning

confidence: 99%

“…The only exception to this general trend is represented by complex 3 g, for which the coordination on the metal centre of 2trifurylphosphine lowers the chemical shift of the peak in the 31 P{ 1 H} NMR spectrum of about 19 ppm, confirming a behaviour already previously observed in other contributions. [8,11] Moreover, the 19 F{ 1 H} NMR spectra of complexes 3 c-d, equipped with fluorinated phosphines, show the signal of para substituents. In the 1 H and 13 C{ 1 H} NMR spectra, all the peaks attributable to coordinate N-heterocyclic carbene can be easily identified, with the signal of the carbene carbon that resonates as a doublet (at ca.…”

Section: Synthesis Of Mixed (Hetero)aryl Phosphine/nhc Palladium(ii) ...mentioning

confidence: 99%

“…In recent time, also our research group has dealt with this research field, preparing and testing different classes of organopalladium derivatives. [6c-i] In particular, our recent study has revealed the promising anticancer activity of palladium(II) indenyl complexes, [8] and in this work we intend to deepen the issue, investigating the effect of the simultaneous presence of one phosphine and one N-heterocyclic carbene as ancillary ligands. Preliminarily to the biological tests, the stability of all complexes has been checked in a DMSO-d 6 /D 2 O solution by NMR spectroscopy: after 24 h no appreciable degradation has been observed with the only exception of complexes 3 a and 3 c that for this reason have been excluded from the screening.…”

Section: Antiproliferative Activity On Ovarian Cancer and Normal Cell...mentioning

confidence: 99%

“…For this reason, the Pd(II)‐indenyl moiety presents an higher coordinative saturation and is less susceptible to nucleophilic attack than the Pd(II)‐allyl one. In this context, we have recently reported the first systematic study dealing with the reactivity and antitumor activity of a large library of palladium(II) indenyl complexes bearing monodentate or bidentate phosphine ligands, showing the significant influence of steric and electronic parameters of the employed phosphines on the behaviour of the target organopalladium compounds [8] . We believe that the interesting biological results exposed in our first contribution can be a good starting point to make targeted changes in the coordinative sphere of palladium in order to improve the anticancer properties of Pd(II)‐indenyl complexes.…”

Section: Introductionmentioning

confidence: 99%

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Biological and Catalytic Applications of Pd(II)‐Indenyl Complexes Bearing Phosphine andN‐Heterocyclic Carbene Ligands

et al. 2023

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A general synthetic entryway into novel cationic Pd(II) indenyl complexes bearing one alkyl/aryl phosphine and one Nheterocyclic carbene is reported. All metal complexes have been exhaustively characterized by spectroscopic and structural analyses, highlighting that the indenyl fragment has an hapticity intermediate between η 3 and η 5 . Most of the target complexes are stable in solid state and in solution for a long time. Two different applications of these organopalladium compounds are proposed. Firstly, they have been tested as antiproliferative agents towards three different ovarian cancer cell lines, showing a cytotoxicity significantly higher than that of cisplatin, with a clear dependence on the nature of the coordinated phosphine. Moreover, the similar cytotoxicity towards cisplatin-sensitive and cisplatin-resistant cell lines suggests that these new palladium derivatives act with a different mechanism of action with respect to classical platinum-based drugs. Finally, the water-soluble palladium complexes bearing 1,3,5triaza-7-phosphaadamantane (PTA) have demonstrated interesting catalytic performances in Suzuki-Miyaura coupling in aqueous media, being, inter alia, readily and efficiently recyclable.

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Section: Introductionmentioning

confidence: 83%

Section: Entrymentioning

confidence: 99%

Section: Synthesis Of Mixed (Hetero)aryl Phosphine/nhc Palladium(ii) ...mentioning

confidence: 99%

Section: Antiproliferative Activity On Ovarian Cancer and Normal Cell...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Biological and Catalytic Applications of Pd(II)‐Indenyl Complexes Bearing Phosphine andN‐Heterocyclic Carbene Ligands

et al. 2023

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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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Synthesis and Anticancer Properties of Heterobimetallic Fe(II)/Pd(II) Complexes Bearing Different Butadienyl Fragments

Bortolamiol,

Dalla Pozza,

Demitri

et al. 2024

Eur J Inorg Chem

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In this work, we describe the synthesis of heterobimetallic Fe(II)/Pd(II) complexes bearing different halides and halide‐substituted butadienyl ligands. The synthetic approach involves the preparation of suitable Pd(II)‐butadienyl precursors containing a thioquinoline moiety, followed by the substitution of this relatively labile ligand with dppf (dppf = 1,1'‐bis(diphenylphosphino)ferrocene). With the exception of complexes containing at least one iodine atom, all compounds were synthesized in high yields and purity, and thoroughly characterized using spectroscopic and diffractometric methods. The investigation of the antiproliferative activity of the synthesized organometallic complexes against ovarian and breast cancer cell lines revealed that all compounds exhibit noteworthy cytotoxicity, with IC50 values in the micromolar range and generally comparable to those of cisplatin. Interestingly, significant differences of cytotoxicity among the analysed compounds were observed in the case of MRC‐5 normal cells. Of particular interest is the dichloride derivative 3a, which is essentially inactive towards non‐cancerous cells (IC50 > 100 µM), thus demonstrating promising in vitro selectivity that we believe warrants further investigation in the future.

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Cationic palladium(ii)-indenyl complexes bearing phosphines as ancillary ligands: synthesis, and study of indenyl amination and anticancer activity

Abstract: The reactivity of palladium(II) indenyl derivatives and their applications are topics relatively little studied, though in recent times these compounds have been used as pre-catalysts able to promote challenging cross-coupling...

Cited by 9 publications

References 75 publications

Biological and Catalytic Applications of Pd(II)‐Indenyl Complexes Bearing Phosphine andN‐Heterocyclic Carbene Ligands

Biological and Catalytic Applications of Pd(II)‐Indenyl Complexes Bearing Phosphine andN‐Heterocyclic Carbene Ligands

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

Synthesis and Anticancer Properties of Heterobimetallic Fe(II)/Pd(II) Complexes Bearing Different Butadienyl Fragments

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