Alpha (α-) and beta (β-carboranyl-C-deoxyribosides: Syntheses, structures and biological evaluation

Šnajdr, Ivan; Janoušek, Zbyněk; Takagaki, Masao; Cı́sařová, Ivana; Hosmane, Narayan S.; Kotora, Martin

doi:10.1016/j.ejmech.2014.06.005

Cited by 10 publications

(5 citation statements)

References 32 publications

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“…[14] Anomeric deoxyribosyl acid reacted smoothly to furnish the product as a mixture of α and β-anomers in high yield (4c, 85%, β : α= 1 : 2). [15] It is gratifying that the reaction of anomeric glucosyl acid proceed well to afford the product in good yield while excellent α selectivity was observed (4d, 76% yield, α : β > 99 : 1). The stereochemistry of 4d is consistent with that reported in the literature and further validated by NMR data analysis (Schemes S1-S2).…”

Section: Resultsmentioning

confidence: 97%

Highly Stereoselective C‐Glycosylation by Photocatalytic Decarboxylative Alkynylation on Anomeric Position: A Facile Access to Alkynyl C‐Glycosides

Liu

et al. 2022

Chin. J. Chem.

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The highly stereoselective synthesis of diverse medicinally valuable alkynyl C-glycosides under mild and green reaction conditions remains a great challenge. Herein, we wish to report a visible-light induced photocatalytic decarboxylative alkynylation approach. By utilizing an iridium photocatalyst in the presence of visible light, glycosyl radicals are in-situ generated via the decarboxylation of anomeric acids and efficiently coupled with a variety of ethynylbenziodoxolones (EBXs), which allows the facile synthesis of a variety of alkynyl C-glycosides in moderate to high yields and with excellent diastereoselectivity..

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Section: Resultsmentioning

confidence: 97%

Highly Stereoselective C‐Glycosylation by Photocatalytic Decarboxylative Alkynylation on Anomeric Position: A Facile Access to Alkynyl C‐Glycosides

Liu

et al. 2022

Chin. J. Chem.

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“…In addition to thymidine analogs, Hosmane et al have synthesized and evaluated a series of carborane-appended 5-thio-D-glucopyranose [60] and deoxyribose derivatives [57] as promising BNCT agents (Fig. 2).…”

Section: Nucleoside and Carbohydrate Analogsmentioning

confidence: 98%

“…Boronated deoxyribose derivatives have been investigated as a novel approach to improve boron uptake in tumor cells due to their higher metabolic activity [57]. These agents are a primary substrate for human thymidine kinase-1 and achieve their tumor selectivity through subsequent phosphorylations which entraps them intracellularly [58].…”

Section: Nucleoside and Carbohydrate Analogsmentioning

confidence: 99%

Advancements in Tumor Targeting Strategies for Boron Neutron Capture Therapy

2015

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Boron neutron capture therapy (BNCT) is a promising cancer therapy modality that utilizes the nuclear capture reaction of epithermal neutrons by boron-10 resulting in a localized nuclear fission reaction and subsequent cell death. Since cellular destruction is limited to approximately the diameter of a single cell, primarily only cells in the neutron field with significant boron accumulation will be damaged. However, the emergence of BNCT as a prominent therapy has in large part been hindered by a paucity of tumor selective boron containing agents. While L-boronophenylalanine and sodium borocaptate are the most commonly investigated clinical agents, new agents are desperately needed due to their suboptimal tumor selectivity. This review will highlight the various strategies to improve tumor boron delivery including: nucleoside and carbohydrate analogs, unnatural amino acids, porphyrins, antibody-dendrimer conjugates, cationic polymers, cell-membrane penetrating peptides, liposomes and nanoparticles.

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“…Highly oxygenated regions (close proximity to blood vessels) are characterized with fast tumor proliferation and oxidative metabolism (12), while hypoxic regions (with low oxygenation) are characterized with low proliferation and reductive metabolism (13). Hypoxic conditions in GBM tumors have been shown to decrease cell proliferation (14), induce metastasis (15), promote angiogenesis (16), and confer resistance to chemotherapy (17) and XRT (18).…”

Section: Introductionmentioning

confidence: 99%

A Hypoxia-Targeted Boron Neutron Capture Therapy Agent for the Treatment of Glioma

et al. 2016

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Purpose Boron neutron capture therapy (BNCT) has the potential to become a viable cancer treatment modality, but its clinical translation has been limited by the poor tumor selectivity of agents. To address this unmet need, a boronated 2-nitroimidazole derivative (B-381) was synthesized and evaluated for its capability of targeting hypoxic glioma cells. Methods B-381 has been synthesized from a 1-step reaction. Using D54 and U87 glioma cell lines, the in vitro cytotoxicity and cellular accumulation of B-381 has been evaluated under normoxic and hypoxic conditions compared to L-boronophenylalanine (BPA). Furthermore, tumor retention of B-381 was evaluated in vivo. Results B-381 had low cytotoxicity in normal and cancer cells. Unlike BPA, B-381 illustrated preferential retention in hypoxic glioma cells compared to normoxic glioma cells and normal tissues in vitro. In vivo, B-381 illustrated significantly higher long-term tumor retention compared to BPA, with 9.5-fold and 6.5-fold higher boron levels at 24 and 48 h, respectively. Conclusions B-381 represents a new class of BNCT agents in which their selectivity to tumors is based on tumor hypoxic metabolism, and further studies are warranted to evaluate this compound and similar compounds as preclinical candidates for future BNCT clinical trials for the treatment of glioma.

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Alpha (α-) and beta (β-carboranyl-C-deoxyribosides: Syntheses, structures and biological evaluation

Cited by 10 publications

References 32 publications

Highly Stereoselective C‐Glycosylation by Photocatalytic Decarboxylative Alkynylation on Anomeric Position: A Facile Access to Alkynyl C‐Glycosides

Highly Stereoselective C‐Glycosylation by Photocatalytic Decarboxylative Alkynylation on Anomeric Position: A Facile Access to Alkynyl C‐Glycosides

Advancements in Tumor Targeting Strategies for Boron Neutron Capture Therapy

A Hypoxia-Targeted Boron Neutron Capture Therapy Agent for the Treatment of Glioma

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