Phosphorescent ruthenium complexes with bromopyrene unit that enhance oxygen sensitivity

Kurihara, Ryohsuke; Ikegami, Ryo; Asahi, Wataru; Tanabe, Kazuhito

doi:10.1016/j.bmc.2018.03.043

Cited by 6 publications

(6 citation statements)

References 28 publications

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“…Ir(III) complexes have attracted increasing attention because of their excellent photophysical and electrochemical properties in a variety of applications, as well as their ease of chemical modification. Typical applications include organic light-emitting diodes (OLED), light-emitting electrochemical cells, photoredox catalysts, photodynamic therapy (PDT), and bioimaging. − As an application for bioimaging, Ir(III) complexes have been used as optical probes for molecular oxygen (O 2 ) in living cells and tissues − in addition to other transition-metal complexes such as Pt(II) and Pd(II) porphyrins, − Ru(II) complexes, − and Pt(II) complexes . Oxygen levels are generally quantified based on lifetime measurements of phosphorescent probes, while ratiometric probes that do not require lifetime measurement have also been developed using phosphorescent metal complexes. − Although the lifetime-based method requires sophisticated equipment, the quantitative accuracy of in vivo measurements is generally superior to the ratiometric method.…”

Section: Introductionmentioning

confidence: 99%

Near-Infrared Emitting Ir(III) Complexes Bearing a Dipyrromethene Ligand for Oxygen Imaging of Deeper Tissues In Vivo

et al. 2022

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Phosphorescence lifetime imaging microscopy (PLIM) using a phosphorescent oxygen probe is an innovative technique for elucidating the behavior of oxygen in living tissues. In this study, we designed and synthesized an Ir(III) complex, PPYDM-BBMD, that exhibits long-lived phosphorescence in the near-infrared region and enables in vivo oxygen imaging in deeper tissues. PPYDM-BBMD has a π-extended ligand based on a mesomesityl dipyrromethene structure and phenylpyridine ligands with cationic dimethylamino groups to promote intracellular uptake. This complex gave a phosphorescence spectrum with a maximum at 773 nm in the wavelength range of the so-called biological window and exhibited an exceptionally long lifetime (18.5 μs in degassed acetonitrile), allowing for excellent oxygen sensitivity even in the near-infrared window. PPYDM-BBMD showed a high intracellular uptake in cultured cells and mainly accumulated in the endoplasmic reticulum. We evaluated the oxygen sensitivity of PPYDM-BBMD phosphorescence in alpha mouse liver 12 (AML12) cells based on the Stern−Volmer analysis, which gave an O 2 -induced quenching rate constant of 1.42 × 10 3 mmHg −1 s −1 . PPYDM-BBMD was administered in the tail veins of anesthetized mice, and confocal one-photon PLIM images of hepatic tissues were measured at different depths from the liver surfaces. The PLIM images visualized the oxygen gradients in hepatic lobules up to a depth of about 100 μm from the liver surfaces with a cellular-level resolution, allowing for the quantification of oxygen partial pressure based on calibration results using AML12 cells.

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Section: Introductionmentioning

confidence: 99%

Near-Infrared Emitting Ir(III) Complexes Bearing a Dipyrromethene Ligand for Oxygen Imaging of Deeper Tissues In Vivo

et al. 2022

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“…Emission images of A549 cells incubated with Ru-BrPy. Reproduced from ref with permission. Copyright (2018) Elsevier Ltd. (f) AuNRs-Laden macrophages for tumor PA imaging and PTT.…”

Section: Hypoxia Imagingmentioning

confidence: 99%

“…To enhance the O 2 response of phosphorescence, Ryohsuke et al created ruthenium complexes by adding naphthalene, bromopyrene, or anthracene units (Figure 13e). 385 The ruthenium complexes with a bromopyrene unit (Ru-BrPy) showed good sensitivity to molecular O 2 for detecting cellular hypoxia. The phosphorescence imaging nanostrategies can directly measure O 2 levels in vivo for hypoxia imaging and are developed well owing to the direct measurement of molecular O 2 and their excellent spatial resolution.…”

Section: Aggregation-induced Emission (Aie)mentioning

confidence: 99%

“…Phosphorescent ruthenium complexes are an extremely helpful imaging tool for determining the presence of hypoxia. To enhance the O 2 response of phosphorescence, Ryohsuke et al created ruthenium complexes by adding naphthalene, bromopyrene, or anthracene units (Figure e) . The ruthenium complexes with a bromopyrene unit (Ru-BrPy) showed good sensitivity to molecular O 2 for detecting cellular hypoxia.…”

Section: Hypoxia Imagingmentioning

confidence: 99%

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Nanomedicine Strategies in Conquering and Utilizing the Cancer Hypoxia Environment

Pan,

Liu,

Mou

et al. 2023

ACS Nano

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Cancer with a complex pathological process is a major disease to human welfare. Due to the imbalance between oxygen (O 2 ) supply and consumption, hypoxia is a natural characteristic of most solid tumors and an important obstacle for cancer therapy, which is closely related to tumor proliferation, metastasis, and invasion. Various strategies to exploit the feature of tumor hypoxia have been developed in the past decade, which can be used to alleviate tumor hypoxia, or utilize the hypoxia for targeted delivery and diagnostic imaging. The strategies to alleviate tumor hypoxia include delivering O 2 , in situ O 2 generation, reprogramming the tumor vascular system, decreasing O 2 consumption, and inhibiting HIF-1 related pathways. On the other side, hypoxia can also be utilized for hypoxia-responsive chemical construction and hypoxia-active prodrug-based strategies. Taking advantage of hypoxia in the tumor region, a number of methods have been applied to identify and keep track of changes in tumor hypoxia. Herein, we thoroughly review the recent progress of nanomedicine strategies in both conquering and utilizing hypoxia to combat cancer and put forward the prospect of emerging nanomaterials for future clinical transformation, which hopes to provide perspectives in nanomaterials design.

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“…Recently, several technologies including oxygen-responsive electrodes, 8,9 functional nanomaterials, 10-12 uorescence [13][14][15][16][17][18][19][20] or phosphorescence emission [21][22][23][24][25][26][27][28][29][30][31][32] and magnetic resonance imaging (MRI) [33][34][35][36] have been adapted to visualize tumor hypoxia. Although these methods are useful for diagnosis, each has considerable limitations.…”

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confidence: 99%

Biological reduction of nitroimidazole-functionalized gold nanorods for photoacoustic imaging of tumor hypoxia

et al. 2019

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Phosphorescent ruthenium complexes with bromopyrene unit that enhance oxygen sensitivity

Cited by 6 publications

References 28 publications

Near-Infrared Emitting Ir(III) Complexes Bearing a Dipyrromethene Ligand for Oxygen Imaging of Deeper Tissues In Vivo

Near-Infrared Emitting Ir(III) Complexes Bearing a Dipyrromethene Ligand for Oxygen Imaging of Deeper Tissues In Vivo

Nanomedicine Strategies in Conquering and Utilizing the Cancer Hypoxia Environment

Biological reduction of nitroimidazole-functionalized gold nanorods for photoacoustic imaging of tumor hypoxia

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