Triphenylamine-appended cyclometallated iridium(III) complexes: Preparation, photophysical properties and application in biology/luminescence imaging

Liu, Xicheng; Hao, Hailong; Ge, Xingxing; He, Xiangdong; Liu, Yifei; Wang, Yan; Wang, Haojie; Shao, Mingxiao; Tian, Laijin; Liu, Zhe

doi:10.1016/j.jinorgbio.2019.110757

Cited by 18 publications

(14 citation statements)

References 55 publications

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“…Therefore, metastasis inhibition study is one of the foremost research areas of advanced cancer treatment. 30,31 For evaluating the effect of compounds on the migration capacity, HeLa cells were treated with complexes 1–4 at their IC 50 values and analysed for cell migration with time intervals. After 24 h of drug treatment, the treated cells show little or no migration at all in the scratched wound region while the PBS-treated cells (without drug treatment) showed significant migration to the scratched wound region (Fig.…”

Section: Resultsmentioning

confidence: 99%

Pyrene-based fluorescent Ru(ii)-arene complexes for significant biological applications: catalytic potential, DNA/protein binding, two photon cell imaging andin vitrocytotoxicity

et al. 2022

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Section: Resultsmentioning

confidence: 99%

Pyrene-based fluorescent Ru(ii)-arene complexes for significant biological applications: catalytic potential, DNA/protein binding, two photon cell imaging andin vitrocytotoxicity

et al. 2022

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“…These complexes can prevent several cancerous processes, such as cell migration, metastasis, invasion, colony formation, and angiogenesis. A series of published triphenylamine conjugated complexes showed that the modification of ligands enabled researchers to fine-tune the lipophilicity of these complexes, and, while they all accumulated in the lysosome and have good IC 50 values, only one was selective of cancerous cells over normal cells (Table 1: IR16) [38]. The resulting complexes (Figure 3: IR16) acquired good fluorescence properties that enabled the identification of lysosomal accumulation and appear to be dual-functional with both metastasis inhibition and lysosomal mediated cell death.…”

Section: Lysosomal Targetingmentioning

confidence: 99%

“…The resulting complexes (Figure 3: IR16) acquired good fluorescence properties that enabled the identification of lysosomal accumulation and appear to be dual-functional with both metastasis inhibition and lysosomal mediated cell death. Iridium complexes: half-sandwich complex IR13 [34], cyclometallated complexes IR15 [37] and IR16 [38], and P^P complex IR14 [36].…”

Section: Lysosomal Targetingmentioning

confidence: 99%

Photoactive and Luminescent Transition Metal Complexes as Anticancer Agents: A Guiding Light in the Search for New and Improved Cancer Treatments

McGhie

Aldrich‐Wright

2022

Biomedicines

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Cancer continues to be responsible for the deaths of more than 9 million people worldwide each year. Current treatment options are diverse, but low success rates, particularly for those with late-stage cancers, continue to be a problem for clinicians and their patients. The effort by researchers globally to find alternative treatment options is ongoing. In the present study, we focused on innovations in inorganic anticancer therapies, specifically those with photoactive and luminescent properties. Transition metals offer distinct advantages compared to wholly organic compounds in both chemotherapeutics and luminescence properties. Here we report on the characteristics that result from discrete structural changes that have been expertly used to fine-tune their properties, and how diverse inherent luminescent properties have been widely employed to monitor cellular localization to photodynamic therapy.

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“…The 4,4′-diTPAbpy ligand and related systems have been more well studied. Iridium(III) complexes of 4,4′-diTPAbpy have been examined as luminescence imaging probes and for their anticancer activity . A family of heteroleptic Ru(II) 4,4′-diTPAbpy complexes have been used as dyes for DSSC. − Additionally, Housecroft, Constable, and co-workers have synthesized a range of 4,4′-diTPAbpy featuring additional substituents (R 1 = Me, Et, Bu, Ph, and Nap) in the 6,6′ position of the bpy.…”

Section: Introductionmentioning

confidence: 99%

“…27 The 4,4′-diTPAbpy ligand and related systems have been more well studied. Iridium(III) complexes of 4,4′-diTPAbpy have been examined as luminescence imaging probes 28 and for their anticancer activity. 29 A family of heteroleptic Ru(II) 4,4′-diTPAbpy complexes have been used as dyes for DSSC.…”

Section: ■ Introductionmentioning

confidence: 99%

6,6′-Ditriphenylamine-2,2′-bipyridine: Coordination Chemistry and Electrochemical and Photophysical Properties

et al. 2021

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A 2,2′-bipyridine with bulky triphenylamine substituents in the 6 and 6′ positions of the ligand (6,6′-ditriphenylamine-2,2′-bipyridine, 6,6′-diTPAbpy) was generated. Despite the steric bulk, the ligand readily formed bis(homoleptic) complexes with copper(I) and silver(I) ions. Unfortunately, efforts to use the 6,6′-diTPAbpy system to generate heteroleptic [Cu(6,6′-diTPAbpy)(bpy)]+ complexes were unsuccessful with only the [Cu(6,6′-diTPAbpy)2](PF6) complex observed. The 6,6′-diTPAbpy ligand could also be reacted with 6-coordinate metal ions that featured small ancillary ligands, namely, the [Re(CO)3Cl] and [Ru(CO)2Cl2] fragments. While the complexes could be formed in good yields, the steric bulk of the TPA units does alter the coordination geometry. This is most readily seen in the [(6,6′-diTPAbpy)Re(CO)3Cl] complex where the Re(I) ion is forced to sit 23° out of the plane formed by the bpy unit. The electrochemical and photophysical properties of the family of compounds were also examined. 6,6′-diTPAbpy exhibits a strong ILCT absorption band (356 nm, 50 mM–1 cm–1) which displays a small increase in intensity for the homoleptic complexes ([Cu(6,6′-diTPAbpy)2]+; 353 nm, 72 mM–1 cm–1, [Ag(6,6′-diTPAbpy)2]+; 353 nm, 75 mM–1 cm–1), despite containing 2 equiv of the ligand, attributed to an increased dihedral angle between the TPA and bpy moieties. For the 6-coordinate complexes the ILCT band is further decreased in intensity and overlaps with MLCT bands, consistent with a further increased TPA-bpy dihedral angle. Emission from the 1ILCT state is observed at 436 nm (τ = 4.4 ns) for 6,6′-diTPAbpy and does not shift for the Cu, Ag, and Re complexes, although an additional 3MLCT emission is observed for [Re(6,6′-diTPAbpy)(CO)3Cl] (640 nm, τ = 13.8 ns). No emission was observed for [Ru(6,6′-diTPAbpy)(CO)2Cl2]. Transient absorption measurements revealed the population of a 3ILCT state for the Cu and Ag complexes (τ = 80 ns). All assignments were supported by TD-DFT calculations and resonance Raman spectroscopic measurements.

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Triphenylamine-appended cyclometallated iridium(III) complexes: Preparation, photophysical properties and application in biology/luminescence imaging

Cited by 18 publications

References 55 publications

Pyrene-based fluorescent Ru(ii)-arene complexes for significant biological applications: catalytic potential, DNA/protein binding, two photon cell imaging andin vitrocytotoxicity

Pyrene-based fluorescent Ru(ii)-arene complexes for significant biological applications: catalytic potential, DNA/protein binding, two photon cell imaging andin vitrocytotoxicity

Photoactive and Luminescent Transition Metal Complexes as Anticancer Agents: A Guiding Light in the Search for New and Improved Cancer Treatments

6,6′-Ditriphenylamine-2,2′-bipyridine: Coordination Chemistry and Electrochemical and Photophysical Properties

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