Exploring the potential of N^C^N cyclometalated Pt(II) complexes bearing 1,3-di(2-pyridyl)benzene derivatives for imaging and photodynamic therapy

Soricellis, Giulia De; Fagnani, Francesco; Colombo, Alessia; Dragonetti, Claudia; Roberto, Dominique

doi:10.1016/j.ica.2022.121082

Cited by 10 publications

(11 citation statements)

References 104 publications

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“…In general, the values are consistent with the Φ Δ values described in the bibliographic literature for comparable Re(I) complexes with bidentate ligands, 25,33,68 as well as for Pt(II) complexes with tridentate luminophores. 69 Furthermore, the estimation of P Od 2 T can be achieved by using the experimental values of τ air and τ Ar (see Table 1). Notably, the fraction of triplet states quenched by dioxygen ( 3 O 2 ) remains consistently high across all examined cases.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Functional Pt(II) and Re(I) Complexes with CO- and β-Carboline-Based Coligands: From Time-Resolved Photoluminescence Spectroscopy and Evaluation of ¹O₂ Photosensitization Efficiency toward in vitro (Photo)cytotoxicity

Kirse,

Maisuls,

Denofrio

et al. 2024

Organometallics

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In this study, the synthesis, photophysical characterization, and (photo)biological assessment of functional rhenium(I)-and platinum(II)based complexes are presented. These compounds feature anionic 1,2,4triazolylpyridine-based chromophores and neutral βC-based monodentate coligands, specifically 9H-pyrido[3,4-b]indole (nHo) or 9-methyl-9H-pyrido-[3,4-b]indole (MenHo), which have been chosen to promote their biological activity. The impact of transition metal cations, coordination geometries, substitution patterns of the luminophore and coligands on the properties of these complexes was thoroughly assessed, encompassing photoluminescence and singlet dioxygen ( 1 O 2 ) quantum yields, excited state lifetimes, and (non)radiative rate constants, across various temperatures and phases. Superior photophysical characteristics were attained by the Pt(II)-based complexes, while effective capabilities as photosensitizers of 1 O 2 were observed for all coordination compounds. Incorporation of these complexes into a polymeric matrix (PMMA) significantly enhanced their luminescence efficiencies by preventing diffusional quenching arising from triplet dioxygen ( 3 O 2 ). Furthermore, a comprehensive (photo)cytotoxicity study on human telomerase reverse transcriptase (hTERT)-immortalized cells was conducted to assess the potential applications of these complexes in photodynamic therapy. In summary, a versatile platform for designing photofunctional materials with photosensitizing properties is offered by this coordination chemical approach. Precise control of photophysical and (photo)biological attributes is achievable through the careful selection of metal centers, substitution patterns, and ancillary ligands.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Functional Pt(II) and Re(I) Complexes with CO- and β-Carboline-Based Coligands: From Time-Resolved Photoluminescence Spectroscopy and Evaluation of ¹O₂ Photosensitization Efficiency toward in vitro (Photo)cytotoxicity

Kirse,

Maisuls,

Denofrio

et al. 2024

Organometallics

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“…81 In recent years, luminescent metal based drugs, in particular Ru(II) Ir(III) and Pt(II) complexes, are being actively investigated due to their outstanding results in PDT based cancer therapy. 40,[82][83][84][85][86][87] Due to the ability of these iridium complexes to generate 1 O 2 upon irradiation and their photostability, they can be considered as potential tools in phototheranostics. Therefore, we decided to evaluate the potential use of complexes 2b-Cl and 2c-Cl in photodynamic therapy based on their light cytotoxic effects in normal cell culture.…”

Section: Dalton Transactions Papermentioning

confidence: 99%

A new family of luminescent iridium complexes: synthesis, optical, and cytotoxic studies

et al. 2023

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“…In the search for blocking such binding mode, the focus later shifted toward the use of analogous substituted at 5-position of the phenyl group or alternatively at 4 and 6 positions, receiving special attention the pro-ligand 1,3-di(2-pyridyl)-4,6-dimethylbenzene . Among the complexes supported by these scaffolds, platinum(II) derivatives attract growing interest, partially due to their use for application in photonics, optoelectronics, and medicinal chemistry . The rigidity of the M(κ 3 - N , C , N ) scaffold and the stability of the tridentate bonding are among the main features provided by the mer -coordination .…”

Section: Introductionmentioning

confidence: 99%

Competition between N,C,N-Pincer and N,N-Chelate Ligands in Platinum(II)

et al. 2023

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Replacement of the chloride ligand of PtCl{κ3-N,C,N-[py-C6HR2-py]} (R = H (1), Me (2)) and PtCl{κ3-N,C,N-[py-O-C6H3-O-py]} (3) by hydroxido gives Pt(OH){κ3-N,C,N-[py-C6HR2-py]} (R = H (4), Me (5)) and Pt(OH){κ3-N,C,N-[py-O-C6H3-O-py]} (6). These compounds promote deprotonation of 3-(2-pyridyl)pyrazole, 3-(2-pyridyl)-5-methylpyrazole, 3-(2-pyridyl)-5-trifluoromethylpyrazole, and 2-(2-pyridyl)-3,5-bis(trifluoromethyl)pyrrole. The coordination of the anions generates square-planar derivatives, which in solution exist as a unique species or equilibria between isomers. Reactions of 4 and 5 with 3-(2-pyridyl)pyrazole and 3-(2-pyridyl)-5-methylpyrazole provide Pt{κ3-N,C,N-[py-C6HR2-py]}{κ1-N 1-[R′pz-py]} (R = H; R′ = H (7), Me (8). R = Me; R′ = H (9), Me (10)), displaying κ1-N 1-pyridylpyrazolate coordination. A 5-trifluoromethyl substituent causes N1-to-N2 slide. Thus, 3-(2-pyridyl)-5-trifluoromethylpyrazole affords equilibria between Pt{κ3-N,C,N-[py-C6HR2-py]}{κ1-N 1-[CF3pz-py]} (R = H (11a), Me (12a)) and Pt{κ3-N,C,N-[py-C6HR2-py]}{κ1-N 2-[CF3pz-py]} (R = H (11b), Me (12b)). 1,3-Bis(2-pyridyloxy)phenyl allows the chelating coordination of the incoming anions. Deprotonations of 3-(2-pyridyl)pyrazole and its substituted 5-methyl counterpart promoted by 6 lead to equilibria between Pt{κ3-N,C,N-[pyO-C6H3-Opy]}{κ1-N 1-[R′pz-py]} (R′ = H (13a), Me (14a)) with a κ-N 1-pyridylpyrazolate anion, keeping the pincer coordination of the di(pyridyloxy)aryl ligand, and Pt{κ2-N,C-[pyO-C6H3(Opy)]}{κ2-N,N-[R′pz-py]} (R′ = H (13c), Me (14c)) with two chelates. Under the same conditions, 3-(2-pyridyl)-5-trifluoromethylpyrazole generates the three possible isomers: Pt{κ3-N,C,N-[pyO-C6H3-Opy]}{κ1-N 1-[CF3pz-py]} (15a), Pt{κ3-N,C,N-[pyO-C6H3-Opy]}{κ1-N 2-[CF3pz-py]} (15b), and Pt{κ2-N,C-[pyO-C6H3(Opy)]}{κ2-N,N-[CF3pz-py]} (15c). The N1-pyrazolate atom produces a remote stabilizing effect on the chelating form, pyridylpyrazolates being better chelate ligands than pyridylpyrrolates. Accordingly, reactions of 4–6 with 2-(2-pyridyl)-3,5-bis(trifluoromethyl)pyrrole yield Pt{κ3-N,C,N-[py-C6HR2-py]}{κ1-N 1-[(CF3)2C4(py)HN]} (R = H (16), Me (17)) or Pt{κ3-N,C,N-[pyO-C6H3-Opy]}{κ1-N 1-[(CF3)2C4(py)HN]} (18), displaying κ1-N 1-pyrrolate coordination. Complexes 7–10 are efficient green phosphorescent emitters (488–576 nm). In poly(methyl methacrylate) (PMMA) films and in dichloromethane, they experience self-quenching, due to molecular stacking. Aggregation occurs through aromatic π–π interactions, reinforced by weak platinum–platinum interactions.

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Exploring the potential of N^C^N cyclometalated Pt(II) complexes bearing 1,3-di(2-pyridyl)benzene derivatives for imaging and photodynamic therapy

Cited by 10 publications

References 104 publications

Functional Pt(II) and Re(I) Complexes with CO- and β-Carboline-Based Coligands: From Time-Resolved Photoluminescence Spectroscopy and Evaluation of ¹O₂ Photosensitization Efficiency toward in vitro (Photo)cytotoxicity

Functional Pt(II) and Re(I) Complexes with CO- and β-Carboline-Based Coligands: From Time-Resolved Photoluminescence Spectroscopy and Evaluation of ¹O₂ Photosensitization Efficiency toward in vitro (Photo)cytotoxicity

A new family of luminescent iridium complexes: synthesis, optical, and cytotoxic studies

Competition between N,C,N-Pincer and N,N-Chelate Ligands in Platinum(II)

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Exploring the potential of N^C^N cyclometalated Pt(II) complexes bearing 1,3-di(2-pyridyl)benzene derivatives for imaging and photodynamic therapy

Cited by 10 publications

References 104 publications

Functional Pt(II) and Re(I) Complexes with CO- and β-Carboline-Based Coligands: From Time-Resolved Photoluminescence Spectroscopy and Evaluation of 1O2 Photosensitization Efficiency toward in vitro (Photo)cytotoxicity

Functional Pt(II) and Re(I) Complexes with CO- and β-Carboline-Based Coligands: From Time-Resolved Photoluminescence Spectroscopy and Evaluation of 1O2 Photosensitization Efficiency toward in vitro (Photo)cytotoxicity

A new family of luminescent iridium complexes: synthesis, optical, and cytotoxic studies

Competition between N,C,N-Pincer and N,N-Chelate Ligands in Platinum(II)

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Product

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Functional Pt(II) and Re(I) Complexes with CO- and β-Carboline-Based Coligands: From Time-Resolved Photoluminescence Spectroscopy and Evaluation of ¹O₂ Photosensitization Efficiency toward in vitro (Photo)cytotoxicity

Functional Pt(II) and Re(I) Complexes with CO- and β-Carboline-Based Coligands: From Time-Resolved Photoluminescence Spectroscopy and Evaluation of ¹O₂ Photosensitization Efficiency toward in vitro (Photo)cytotoxicity