ortho-Carboranylphenoxyacetanilides as inhibitors of hypoxia-inducible factor (HIF)-1 transcriptional activity and heat shock protein (HSP) 60 chaperon activity

Li, Guangzhe; Azuma, Soyoko; Sato, Shinichi; Minegishi, Hidemitsu; Nakamura, Hiroyuki

doi:10.1016/j.bmcl.2015.04.088

Cited by 19 publications

(4 citation statements)

References 30 publications

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“…These inhibitors primarily inhibit Hsp60, which inhibits HIF-1 accumulation directly or indirectly. 29 31 Most of the analogs of this series exhibited good GI 50 values consistent with their IC 50 values as shown in Table 9.…”

Section: Boron-based Inhibitorssupporting

confidence: 54%

“…The ortho‐carborane derivative bearing an oxyacrylic amide linker without boronic acid or boronic ester substitution at the phenolic ring ( 20c ) also maintained potency with an IC 50 value of 1.3 μM. A longer linker was not tolerated (IC 50 = 14.6 μM for 20d ) . Most of the analogs of this series exhibited good GI 50 values consistent with their IC 50 values as shown in Table .…”

Section: Boron‐based Inhibitorsmentioning

confidence: 99%

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Hypoxia‐inducible factor‐1 (HIF‐1) inhibitors from the last decade (2007 to 2016): A “structure–activity relationship” perspective

Bhattarai

Lee

2017

Medicinal Research Reviews

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Tumor hypoxia is a common feature in most solid tumors and is associated with overexpression of the hypoxia response pathway. Overexpression of the hypoxia-inducible factor (HIF-1) protein leads to angiogenesis, metastasis, apoptosis resistance, and many other pro-tumorigenic responses in cancer development. HIF-1 is a promising target in cancer drug development to increase the patient's response to chemotherapy and radiotherapy as well as the survival rate of cancer patients. Since up to 1% of genes are hypoxia-sensitive, a target-specific HIF-1 inhibitor may be a better clinical candidate in cancer drug discovery. Though no HIF-1 inhibitor is clinically available to date, a lot of effort has been applied during the last decade in search of potent HIF-1 inhibitors. In this review, we will summarize the structure-activity relationship of ten different chemotypes reported to be HIF-1 inhibitors in the last decade (2007-2016), their mechanisms of action for HIF-1 inhibition, progress in the way of target-specific inhibitors, and problems associated with current inhibitors. It is anticipated that the results of these research on the medicinal chemistry of HIF-1 inhibitors will provide decent information in the design and development of future inhibitors.

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Section: Boron-based Inhibitorssupporting

confidence: 54%

Section: Boron‐based Inhibitorsmentioning

confidence: 99%

Hypoxia‐inducible factor‐1 (HIF‐1) inhibitors from the last decade (2007 to 2016): A “structure–activity relationship” perspective

Bhattarai

Lee

2017

Medicinal Research Reviews

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“…In particular, we focused on globular substituents called o ‐carboranes, which are known as “plastic crystals” . o ‐Carborane (C 2 H 12 B 10 ) is an icosahedral boron cluster that contains two adjacent carbon atoms in the cage . Recent studies have demonstrated that o ‐carborane derivatives that are connected to a π‐conjugated aryl unit at the C1 (and/or C2) position present emissions with intramolecular charge transfer (ICT) character .…”

Section: Introductionmentioning

confidence: 99%

Solid‐State Thermochromic Luminescence through Twisted Intramolecular Charge Transfer and Excimer Formation of a Carborane−Pyrene Dyad with an Ethynyl Spacer

et al. 2017

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The pyrene-tetheredc arborane CBEP,w hichexhibited rapid and dramatic luminochromism, was synthesized. Based on opticalm easurements, we found that CBEP exhibited orange emission at room temperature, which was caused by intramolecular charget ransfer in the solid state, and green excimer emissiona t7 7K.W ep roposed that exci-mer formation could be encouraged by introducing as mall amount of steric hindrance with an ethynyl spacer group. We found that o-carborane could suppress aggregationcausedq uenching without the inhibition of excimer formation because of this steric hindrance.[a] Dr.

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“…[6] o-Carborane (C 2 H 12 B 10 )i sapolyhedral boron-carbon cluster in which two carbon atoms are arranged in an adjacent position. [7] Recently,v arioust ypes of luminescent materials have been constructed based on modified o-carboranes. [8] We also have paid attention to o-carborane as al uminescent "elementblock", [9a] which is defined asaminimum functional unit composed of heteroatoms,f or preparing optically functional solid materials.…”

Section: Introductionmentioning

confidence: 99%

Luminescence Color Tuning from Blue to Near Infrared of Stable Luminescent Solid Materials Based on Bis‐o‐Carborane‐Substituted Oligoacenes

Naito

Nishino

Morisaki

et al. 2017

Chemistry An Asian Journal

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Aryl-substituted o-carboranes have shown highly efficient solid-state emission in previous studies. To demonstrate color tuning of the solid-state emission in an aryl-o-carborane-based system, bis-o-carborane-substituted oligoacenes were synthesized and their properties were systematically investigated. Optical and electrochemical measurements revealed efficient decreases in energy band gaps and lowest unoccupied molecular orbital (LUMO) levels by adding a number of fused benzene rings for the extension of π-conjugation. As a consequence, bright solid-state emission was observed in the region from blue to near infrared (NIR). Furthermore, various useful features were obtained from the modified o-carboranes as an optical material. The naphthalene derivatives exhibited aggregation-induced emission (AIE) and almost 100 % quantum efficiency in the crystalline state. Furthermore, it was shown that the tetracene derivative with NIR-emissive properties had high durability toward photo-bleaching under UV irradiation.

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ortho-Carboranylphenoxyacetanilides as inhibitors of hypoxia-inducible factor (HIF)-1 transcriptional activity and heat shock protein (HSP) 60 chaperon activity

Cited by 19 publications

References 30 publications

Hypoxia‐inducible factor‐1 (HIF‐1) inhibitors from the last decade (2007 to 2016): A “structure–activity relationship” perspective

Hypoxia‐inducible factor‐1 (HIF‐1) inhibitors from the last decade (2007 to 2016): A “structure–activity relationship” perspective

Solid‐State Thermochromic Luminescence through Twisted Intramolecular Charge Transfer and Excimer Formation of a Carborane−Pyrene Dyad with an Ethynyl Spacer

Luminescence Color Tuning from Blue to Near Infrared of Stable Luminescent Solid Materials Based on Bis‐o‐Carborane‐Substituted Oligoacenes

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