Development of Azo‐Based Fluorescent Probes to Detect Different Levels of Hypoxia

Piao, Wen; Tsuda, S.; Tanaka, Yuji; Maeda, Satoshi; Liu, Fengyi; Takahashi, Shodai; Kushida, Yu; Komatsu, Toshimitsu; Ueno, Takahiro; Terai, Takuya; Nakazawa, Toru; Uchiyama, Masanobu; Morokuma, Keiji; Nagano, Tetsuo; Hanaoka, Kenjiro

doi:10.1002/anie.201305784

Cited by 252 publications

(217 citation statements)

References 41 publications

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“…Hanaoka et al conceived a further improvement to azobased hypoxia sensors. 186 They directly conjugated the azo group to per-rhodamine fluorophores and obtained two probes (53a and 53b). Once reduced under hypoxia, the two probes resulted in free fluorophores.…”

Section: Hypoxia-mediated Tumor Imagingmentioning

confidence: 99%

Fluorescent chemical probes for accurate tumor diagnosis and targeting therapy

et al. 2017

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Surgical resection of solid tumors is currently the gold standard and preferred therapeutic strategy for cancer. Chemotherapy drugs also make a significant contribution by inhibiting the rapid growth of tumor cells and these two approaches are often combined to enhance treatment efficacy. However, surgery and chemotherapy inevitably lead to severe side effects and high systemic toxicity, which in turn results in poor prognosis. Precision medicine has promoted the development of treatment modalities that are developed to specifically target and kill tumor cells. Advances in in vivo medical imaging for visualizing tumor lesions can aid diagnosis, facilitate surgical resection, investigate therapeutic efficacy, and improve prognosis. In particular, the modality of fluorescence imaging has high specificity and sensitivity and has been utilized for medical imaging. Therefore, there are great opportunities for chemists and physicians to conceive, synthesize, and exploit new chemical probes that can image tumors and release chemotherapy drugs in vivo. This review focuses on small molecular ligand-targeted fluorescent imaging probes and fluorescent theranostics, including their design strategies and applications in clinical tumor treatment. The progress in chemical probes described here suggests that fluorescence imaging is a vital and rapidly developing field for interventional surgical imaging, as well as tumor diagnosis and therapy.

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Section: Hypoxia-mediated Tumor Imagingmentioning

confidence: 99%

Fluorescent chemical probes for accurate tumor diagnosis and targeting therapy

et al. 2017

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“…Probes Ir1-Ir8 are eligible to function in a complex biological background because their phosphorescent response could be obtained in a mixed solution containing high concentration of ions or bio-related reducing agents in a suitable pH range. These probes could also penetrate 3D multicellular spheroids over 100 μm and image the hypoxic regions in the center which are more suitable models for in vivo solid tumors using fluorescence imaging [31]. …”

Section: Small Molecule and Dye Based Probesmentioning

confidence: 99%

Luminescent Probe Based Techniques for Hypoxia Imaging

Jaworski¹

2017

JNMR

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Hypoxia is a condition of tissue environments wherein a lower than normal level of oxygen is available, and it serves as the root cause and indicator of various diseases. Detection of hypoxia in tumors is imperative for furthering our understanding of the pathological effects and the development of proper treatments, as it is well established that hypoxic tumors are able to impede the cancer treatment process by being resistant to many therapies. It is important therefore to be able to detect hypoxia in tissues and tumors through in vivo imaging methods. A growing area for detection of hypoxia in vivo is the use of fluorescent/luminescent probes which has accelerated in recent years. The continued quest for improvements in selectivity and sensitivity has inspired researchers to pursue new strategies for fluorescence/luminescent probe design. This review will discuss various luminescent probes based on small molecules, dyes, macromolecules, and nanoparticles for sensitive and specific detection of oxygen levels directly or by indirect mechanisms such as the presence of enzymes or related factors that arise in a hypoxic environment. Following the particular mechanism of detection, each probe has specific structural and photophysical properties which permit its selectivity and sensitivity. These probes show promise in terms of low toxicity and high specificity among other merits discussed, and in providing new dimensions for hypoxia detection, these works contribute to future potential methods for clinical diagnosis of hypoxic tissues and tumors.

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“…2-(anthracene-9,10-dione-2-yl)-1-phenyl-1H-imidazo [4,5-f] [1,10]phenanthroline (L 1 ). A mixture of 9,10-phenanthrenequinone (0.212 g, 1.0 mmol), 2-formyl-9,10-anthraquinone (0.236 g, 1.0 mmol), aniline (0.13 g, 1.2 mmol) and ammonium acetate (0.949 g, 12.23 mmol) was refluxing in glacial acetic acid (10 mL) for 24 h under an argon atmosphere.…”

Section: Synthesis Of Ligands L 1e3mentioning

confidence: 99%

“…With this in mind, we synthesised three ruthenium(II) anthraquinone complexes [Ru(bpy) 2 (L 1 )] 2þ (RuL 1 ), [Ru(bpy) 2 (L 2 )] 2þ (RuL 2 ), and [Ru(bpy) 2 [1,10]phenanth roline). The Ru(II) complexes were obtained in yields ranging from 74% to 82% by the direct reaction of L 1e3 with appropriate molar ratios of cis-Ru(bpy) 2 Cl 2 in ethylene glycol.…”

Section: Design and Synthesismentioning

confidence: 99%