Tuning a modular system – synthesis and characterisation of a boron-rich <i>s</i>-triazine-based carboxylic acid and amine bearing a galactopyranosyl moiety

Kellert, Martin; Hoppenz, Paul; Lönnecke, Peter; Worm, Dennis J.; Riedl, Bernd; Koebberling, Johannes; Beck‐Sickinger, Annette G.; Hey‐Hawkins, Evamarie

doi:10.1039/c9dt04031e

Cited by 11 publications

(11 citation statements)

References 64 publications

(102 reference statements)

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“…G-protein-coupled receptors (GPCRs) refer to a large family of cell-surface receptors. 88 , 89 , 90 , 91 , 92 As a seven-pass transmembrane protein, GPCRs that are overexpressed on the membrane of cancer cells bound to peptide ligands and thus could be used as a shuttle for tumor-directed boron absorption systems ( Figure 3 H). 88 Among them, human Y1 receptor (hY1R), 88 , 89 gastrin-releasing peptide receptor (GRPR), 90 and ghrelin receptor (GhrR) 91 , 92 have become viable targets for BNCT by virtue of their high expression on the surface of cancer cells and their ability to internalize the bound ligands.…”

Section: Applications Of Carboranes As Boron Neutron Capture Therapy Agentsmentioning

confidence: 99%

Carboranes as unique pharmacophores in antitumor medicinal chemistry

Chen

Tang

et al. 2022

Molecular Therapy - Oncolytics

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Section: Applications Of Carboranes As Boron Neutron Capture Therapy Agentsmentioning

confidence: 99%

Carboranes as unique pharmacophores in antitumor medicinal chemistry

Chen

Tang

et al. 2022

Molecular Therapy - Oncolytics

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“…After an initial demonstration of the synthetic feasibility, two units of 9-mercaptometa-carborane and some simple nucleophiles (Scheme 8) were introduced on a triazine core [54]. More complex derivatives containing a galactose unit were obtained exploiting previously developed sugar-containing building blocks and 9-mercapto-meta-carborane 47 (Scheme 9) or a newly developed tris-cluster derivative 53 of 47 (Scheme 10) [55,56]. More complex derivatives containing a galactose unit were obtained exploiting previously developed sugar-containing building blocks and 9-mercapto-meta-carborane 47 (Scheme 9) or a newly developed tris-cluster derivative 53 of 47 (Scheme 10) [55,56].…”

Section: 14 X For Peer Review 11 Of 19mentioning

confidence: 99%

“…More complex derivatives containing a galactose unit were obtained exploiting previously developed sugar-containing building blocks and 9-mercapto-meta-carborane 47 (Scheme 9) or a newly developed tris-cluster derivative 53 of 47 (Scheme 10) [55,56]. Compound 47 was also used as a scaffold and decorated with two galactosyl moieties and a carboxymethyl group which allowed the conjugation with neuropeptide Y (NPY), known to be recognized by tumor-overexpressed G protein-coupled receptor (GPCR) [57].…”

Section: 14 X For Peer Review 11 Of 19mentioning

confidence: 99%

Sweet Boron: Boron-Containing Sugar Derivatives as Potential Agents for Boron Neutron Capture Therapy

Imperio

Panza

2022

Symmetry

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Boron neutron capture therapy (BNCT) is a binary type of radiotherapy for the treatment of cancer. Due to recent developments of neutron accelerators and their installation in some hospitals, BNCT is on the rise worldwide and is expected to have a significant impact on patient treatments. Therefore, there is an increasing need for improved boron delivery agents. Among the many small molecules and delivery systems developed, a significant amount of recent research focused on the synthesis of boron-containing sugar and amino acid derivatives to exploit specific transport proteins, as d-glucose transporter 1 (GLUT1) and large neutral amino acid transporter (LAT1), overexpressed by tumor cells. This review will discuss the last year’s achievements in the synthesis and some biological evaluation of boronated sugars derivatives. The compounds described in this review are intrinsically asymmetric due to the presence of chiral sugar moieties, often joined to boron clusters, which are structural elements with high symmetry.

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“…To enhance boron molecular mass fractions, clusters like carboranes (C 2 B 10 H 12 ) [13] can be used for new 2-nitroimidazole-containing BNCT agents. Modular systems based on triazines are yet described and are combined with m-carboranes to boron-rich compounds [14][15][16]. In this paper, a symmetrical hybrid compound containing two carborane residues and 2-nitroimidazole moiety on a triazine scaffold is described as a potential agent for BNCT.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterisation of a Boron-Rich Symmetric Triazine Bearing a Hypoxia-Targeting Nitroimidazole Moiety

et al. 2021

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Boron Neutron Capture Therapy (BNCT) is a binary therapy that promises to be suitable in treating many non-curable cancers. To that, the discovery of new boron compounds able to accumulate selectively in the tumour tissue is still required. Hypoxia, a deficiency of oxygen in tumor tissue, is a great challenge in the conventional treatment of cancer, because hypoxic areas are resistant to conventional anticancer treatments. 2-Nitroimidazole derivatives are known to be hypoxia markers due to their enrichment by bioreduction in hypoxic cells. In the present work, 2-nitroimidazole was chosen as the starting point for the synthesis of a new boron-containing compound based on a 1,3,5-triazine skeleton. Two o-carborane moieties were inserted to achieve a high ratio of boron on the molecular weight, exploiting a short PEG spacer to enhance the polarity of the compound and outdistance the active part from the core. The compound showed no toxicity on normal human primary fibroblasts, while it showed noteworthy toxicity in multiple myeloma cells together with a consistent intracellular boron accumulation.

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Tuning a modular system – synthesis and characterisation of a boron-rich s-triazine-based carboxylic acid and amine bearing a galactopyranosyl moiety

Abstract: Introduction of a galactopyranosyl moiety in s-triazine-based boron-rich carboxylic acids and amines results in soluble and suitable coupling partners for tumour-selective biomolecules with applications in boron neutron capture therapy (BNCT).

Cited by 11 publications

References 64 publications

Carboranes as unique pharmacophores in antitumor medicinal chemistry

Carboranes as unique pharmacophores in antitumor medicinal chemistry

Sweet Boron: Boron-Containing Sugar Derivatives as Potential Agents for Boron Neutron Capture Therapy

Synthesis and Characterisation of a Boron-Rich Symmetric Triazine Bearing a Hypoxia-Targeting Nitroimidazole Moiety

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