Design and discovery of novel dipeptide boronic acid ester proteasome inhibitors, an oral slowly-released prodrug for the treatment of multiple myeloma

Wang, Xueyuan; Zhang, Wen; Wen, Tiantian; Miao, Hang; Hu, Wenjiao; Liu, Hailong; Meng, Lei; Zhu, Yongqiang

doi:10.1016/j.ejmech.2023.115187

Cited by 7 publications

(2 citation statements)

References 24 publications

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“…Wang et al. reported recently the synthesis of a series of dipeptide boronic acid esters and investigated their ability to inhibit the β5 subunit of 20S proteasome as potential oral proteasome inhibitors for the treatment of MM 73 . A new prodrug was found to be stable enough in simulated gastric juice and simulated intestinal juice and displayed strong anti-RPMI-8226 activity both in vitro and in vivo in comparison to the known ixazomib citrate.…”

Section: Other Anticancer Boron-containing Drugs Discoverymentioning

confidence: 99%

Organoboronic acids/esters as effective drug and prodrug candidates in cancer treatments: challenge and hope

Al-Omari,

Elaarag,

Al-Zoubi

et al. 2023

Journal of Enzyme Inhibition and Medicinal Chemistry

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Boronic acids/esters have recently emerged in the field of medicinal and pharmaceutical research due to their exceptional oxophilicity, low toxicity, and unique structure. They are known as potent enzyme inhibitors, cancer therapy capture agents, and can mimic certain types of antibodies to fight infections. They have been designed and developed into drugs, and this approach has emerged in the last 20 years. Five boronic acid drugs have been approved by the FDA and Health Canada, two of which are used to treat cancer, specifically multiple myeloma. The purpose of this review is to investigate boronic acid/ester derivatives as potential pharmaceutical agents as well as the mechanism of action. It will concentrate on six types of cancer: multiple myeloma, prostate cancer, breast cancer, lung cancer, cervical cancer, and colon cancer. Some newly developed boron-containing compounds have already demonstrated highly promising activities, but further investigation is required before final conclusions can be drawn.

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Section: Other Anticancer Boron-containing Drugs Discoverymentioning

confidence: 99%

Organoboronic acids/esters as effective drug and prodrug candidates in cancer treatments: challenge and hope

Al-Omari,

Elaarag,

Al-Zoubi

et al. 2023

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Despite the vast body of scientific evidence, it has not been conclusively reported that B is necessary for both humans and animals. In fact, several BCCs, such as borates, boronates, and boronic acids, exhibited interesting biological activities, including antiviral [2], antibacterial [3,4], antifungal and antiparasitic [5,6], antioxidant [7,8], wound healing [9], anti-inflammatory [10,11], antimutagenic [12], anticancerogenic [13,14], radiobiological [15], and neuroprotective properties [16,17]. Interestingly it was found that people living in B-rich regions had less cancer incidence than the people living in B-poor regions [18].…”

Section: Introductionmentioning

confidence: 99%

Oxidative, Genotoxic and Cytotoxic Damage Potential of Novel Borenium and Borinium Compounds

Oguzkan,

Turkez,

Ugras

et al. 2023

Inorganics

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In this study, the biological properties of novel borenium and borinium compounds in terms of their oxidative, genotoxic, and cytotoxic effects were assessed on cultured human peripheral blood cells, as well as several types of cancer cells. Our results revealed that the borinium compounds yielded the best results in terms of supporting total antioxidant capacity (TAC). In fact, borenium 1, borenium 2, borenium 3, borinium 4, and borinium 5 compounds elevated TAC levels of cultured human blood cells at rates of 42.8%, 101.5%, 69.8%, 33.3%, and 49.2%, respectively. There were no statistically significant differences (p > 0.05) between the negative control and the groups treated with all borinium and borenium concentrations from the micronucleus (MN) and chromosome aberration (CA) assays, demonstrating the non-genotoxic effects. Moreover, borenium 1 (60.7% and 50.7%), borenium 2 (70.4% and 57.2%), borenium 3 (53.1% and 45.2%), borinium 4 (55.1% and 48.1%), and borinium 5 (51.0% and 36.1%) minimized the mitomycin C(MMC)-induced genotoxic damages at different rates as determined using CA and MN assays, respectively. Again, it was found that the borinium compounds exhibited higher cytotoxic activity on cancer cells when compared to borenium compounds. Consequently, in light of our in vitro findings, it was suggested that the novel borinium and borenium compounds could be used safely in pharmacology, cosmetics, and various medical fields due to their antioxidant and non-genotoxic features, as well as their cytotoxicity potential on cancer cells.

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Recent Advances in Transition‐Metal‐Catalyzed Ring‐Retentive Addition Reactions of Oxa(aza)benzonorbornadienes

Lin,

Yang

2023

Adv Synth Catal

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Oxa(aza)benzonorbornadienes are utilized as important synthetic intermediates and useful building blocks in organic synthesis due to their structural features and reactivity. In addition to ring‐opening reactions, the transition‐metal‐catalyzed ring‐retentive addition reactions of oxa(aza)bicyclic alkenes have increasingly drawn the attention of various researchers. Numerous efficient protocols in this field have been investigated that enable facile and efficient transformations of oxa(aza)benzonorbornadienes to related valuable adducts, which are summarized and discussed in detail in this review.

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Design and discovery of novel dipeptide boronic acid ester proteasome inhibitors, an oral slowly-released prodrug for the treatment of multiple myeloma

Cited by 7 publications

References 24 publications

Organoboronic acids/esters as effective drug and prodrug candidates in cancer treatments: challenge and hope

Organoboronic acids/esters as effective drug and prodrug candidates in cancer treatments: challenge and hope

Oxidative, Genotoxic and Cytotoxic Damage Potential of Novel Borenium and Borinium Compounds

Recent Advances in Transition‐Metal‐Catalyzed Ring‐Retentive Addition Reactions of Oxa(aza)benzonorbornadienes

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