Design and synthesis of boron containing monosaccharides by the hydroboration of d-glucal for use in boron neutron capture therapy (BNCT)

Itoh, Taiki; Tamura, Kazutoshi; Ueda, Hiroki R.; Tanaka, Tomohiro; Sato, Kyouhei; Kuroda, Reiko; Aoki, Shin

doi:10.1016/j.bmc.2018.10.041

Cited by 23 publications

(39 citation statements)

References 127 publications

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“…We were unable to isolate the arabino -configurated epimer from the reaction mixture, which, if present, may therefore be formed in a very small amount. As expected, no regioisomer was detected, due to the contribution of both steric and electronic effects on the hydroboration at C-1 [7].…”

Section: Resultssupporting

confidence: 53%

“…Usually, β-alkoxyboronates are reasonably stable with some exceptions [9], while β-hydroxyboronic acids are prone to elimination. However, β-hydroxyboronic acids are described, such as in the case of the previously mentioned glucopyranos-2-ylboronic acid [7] as well as in other reports where they are usually isolated after conversion into trifluoroborates [10].…”

Section: Resultsmentioning

confidence: 99%

“…In the frame of a more general research program, we have recently published the synthesis of boronic acids derivatives of monosaccharides in which one of the sugar hydroxy groups is substituted by a boronic acid moiety [6]. A related approach has been described [7] recently, where, among other derivatives, 1,2-dideoxy-ᴅ-glucopyranos-2-ylboronic acid has been synthesized through a regio- and stereoselective hydroboration of persilylated glucal.…”

Section: Introductionmentioning

confidence: 99%

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Anomeric sugar boronic acid analogues as potential agents for boron neutron capture therapy

Imperio¹,

Grosso²,

Fallarini³

et al. 2019

Beilstein J. Org. Chem.

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After the development of accelerators as neutron source, the access to new suitable agents for boron neutron capture therapy (BNCT) became a major need. Among many others, sugar boronic acids have recently attracted attention as boron carriers. Herein we report the synthesis and preliminary biological studies of two new sugar analogues containing a boronic acid at the anomeric position. The analogues were obtained by hydroboration of proper open-chain terminal alkenes that, after quenching with water, spontaneously afforded cyclic boronic acids with hemiacetal-like structures.

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Section: Resultssupporting

confidence: 53%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Anomeric sugar boronic acid analogues as potential agents for boron neutron capture therapy

Imperio¹,

Grosso²,

Fallarini³

et al. 2019

Beilstein J. Org. Chem.

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“…In addition, we also found that 7 was efficiently transferred into cancer cell lines (Jurkat, A549 and HeLa S3 cells). 15 , 20 In subsequent studies, the decomposition of ortho -carborane-polyamine conjugates upon metal complexation was discovered and applied to the magnetic resonance imaging (MRI) of Cu 2+ in solutions. 21 …”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Boron-Containing Macrocyclic Polyamines and Their Zinc(II) Complexes for Boron Neutron Capture Therapy

et al. 2021

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Boron neutron capture therapy (BNCT) is a binary therapeutic method for cancer treatment based on the use of a combination of a cancer-specific drug containing boron-10 ( 10 B) and thermal neutron irradiation. For successful BNCT, 10 B-containing molecules need to accumulate specifically in cancer cells, because destructive effect of the generated heavy particles is limited basically to boron-containing cells. Herein, we report on the design and synthesis of boron compounds that are functionalized with 9-, 12-, and 15-membered macrocyclic polyamines and their Zn 2+ complexes. Their cytotoxicity, intracellular uptake activity into cancer cells and normal cells, and BNCT effect are also reported. The experimental data suggest that mono- and/or diprotonated forms of metal-free [12]aneN 4 - and [15]aneN 5 -type ligands are uptaken into cancer cells, and their complexes with intracellular metals such as Zn 2+ would induce cell death upon thermal neutron irradiation, possibly via interactions with DNA.

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“…Mannose and its related compounds are also uptaken by mannose receptors broadly expressed in many types of cancer cells [29][30][31]. The Warburg effect, by which anaerobic glycolysis is upregulated in the growing tumor cells and tissues of malignant tumors, relies on glucose, fructose, galactose, and also mannose as the main nutritive supplies [32][33][34]. Recently, a saccharide-conjugated carborane compound (galactosyl carborane) [35], boronated carbohydrates [36][37][38][39], and carbohydrate derivatives of the closo-dodecaborate anion [40][41][42] were reported as specific targeting agents for potential application to BNCT.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of a Novel Boron-Containing α-d-Mannopyranoside for BNCT

Tsurubuchi

Shirakawa

Kurosawa

et al. 2020

Cells

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Boron neutron capture therapy (BNCT) is a unique anticancer technology that has demonstrated its efficacy in numerous phase I/II clinical trials with boronophenylalanine (BPA) and sodium borocaptate (BSH) used as 10B delivery agents. However, continuous drug administration at high concentrations is needed to maintain sufficient 10B concentration within tumors. To address the issue of 10B accumulation and retention in tumor tissue, we developed MMT1242, a novel boron-containing α-d-mannopyranoside. We evaluated the uptake, intracellular distribution, and retention of MMT1242 in cultured cells and analyzed biodistribution, tumor-to-normal tissue ratio and toxicity in vivo. Fluorescence imaging using nitrobenzoxadiazole (NBD)-labeled MMT1242 and inductively coupled mass spectrometry (ICP-MS) were performed. The effectiveness of BNCT using MMT1242 was assessed in animal irradiation studies at the Kyoto University Research Reactor. MMT1242 showed a high uptake and broad intracellular distribution in vitro, longer tumor retention compared to BSH and BPA, and adequate tumor-to-normal tissue accumulation ratio and low toxicity in vivo. A neutron irradiation study with MMT1242 in a subcutaneous murine tumor model revealed a significant tumor inhibiting effect if injected 24 h before irradiation. We therefore report that 10B-MMT1242 is a candidate for further clinical BNCT studies.

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Design and synthesis of boron containing monosaccharides by the hydroboration of d-glucal for use in boron neutron capture therapy (BNCT)

Cited by 23 publications

References 127 publications

Anomeric sugar boronic acid analogues as potential agents for boron neutron capture therapy

Anomeric sugar boronic acid analogues as potential agents for boron neutron capture therapy

Design, Synthesis, and Biological Evaluation of Boron-Containing Macrocyclic Polyamines and Their Zinc(II) Complexes for Boron Neutron Capture Therapy

Evaluation of a Novel Boron-Containing α-d-Mannopyranoside for BNCT

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