Glycoconjugates of polyhedral boron clusters

Satapathy, Rashmirekha; Dash, Barsha; Mahanta, Chandra Sekhara; Swain, Biswa Ranjan; Jena, Bibhuti Bhusan; Hosmane, Narayan S.

doi:10.1016/j.jorganchem.2015.06.027

Cited by 26 publications

(27 citation statements)

References 70 publications

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“…In the past decade, saccharides have been widely studied due to their low toxicities, generally having high water solubility, high expression of specific receptor on the tumor cell surface (specifically in the brain capillary endothelial cells that form the brain barriers, resulting in optimal BBB penetration), and an increased rate of glycolysis in cancer cells. According to this and in order to improve boron uptake, carbohydrates such as ribose, mannose, maltose, and galactose have been chosen to generate carbohydrate-based boron delivery platforms for successful BNCT approach [32,33]. Since the first description by Hawthorne's group [34], there have been numerous works on the synthesis and biological evaluation of carboranylcarbohydrate conjugates.…”

Section: Closo-carboranes and Metallacarboranes Designed And Studied mentioning

confidence: 99%

Medicinal Chemistry of Boron-Bearing Compounds for BNCT- Glioma Treatment: Current Challenges and Perspectives

Cerecetto¹,

Couto²

2019

Glioma - Contemporary Diagnostic and Therapeutic Approaches

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Since its first description, boron neutron capture therapy (BNCT) was a special type of radiotherapy for treatment of cancer and with focus mainly on glioma therapeutic. This procedure requires the selective accumulation of boron into the tumoral cells, and due to this requirement, different boron-enriched compounds have been designed and developed. Efforts to circumvent the selectivity-uptake challenge and other problems, such as solubility, stability, and toxicity, have been to driving force behind the medicinal chemistry field in boron-based compounds. In this regard, a wide diversity of medicinal chemistry hypothesis has been used to obtain new and efficient potential BNCT-glioma drugs. In this chapter, these ideas are analyzed focusing on their medicinal chemistry characteristics.

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Section: Closo-carboranes and Metallacarboranes Designed And Studied mentioning

confidence: 99%

Medicinal Chemistry of Boron-Bearing Compounds for BNCT- Glioma Treatment: Current Challenges and Perspectives

Cerecetto¹,

Couto²

2019

Glioma - Contemporary Diagnostic and Therapeutic Approaches

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“…Boronated glyco-conjugate derivatives, such as glycosides, have attracted significant interest as potential vehicles for the delivery of boron [88], since their precursor glyco-conjugates are important in several biological processes that include cell growth, intercellular communication and intracellular recognition processes [89,90]. Glycoproteins-based targeting is guided by carbohydrate receptor-specific sites at the cell surface and by the expression of lectins at tumour cells [91].…”

Section: Carbohydratesmentioning

confidence: 99%

“…Boronated glyco-conjugate formation is normally facilitated by glycosidic bonds between the carborane unit and the carbohydrate moiety [92]. To impart water solubility to such conjugates [88], the hydrophilic-lipophilic balance of the molecule may be adjusted by elongating the hydroxyl group-decorated carbohydrate moiety. An alternative approach to the synthesis of carboranyl carbohydrates involves the in situ formation of the boron cage.…”

Section: Carbohydratesmentioning

confidence: 99%

Towards carborane-functionalised structures for the treatment of brain cancer

Calabrese

Daou

Barbu

et al. 2018

Drug Discovery Today

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Boron neutron capture therapy (BNCT) is a promising targeted chemoradiotherapeutic technique for the management of invasive brain tumors, such as glioblastoma multiforme (GBM). A prerequisite for effective BNCT is the selective targeting of tumour cells with B-rich therapeutic moieties. To this end, polyhedral boranes, especially carboranes, have received considerable attention because they combine a high boron content with relative low toxicity and metabolic inertness. Here, we review progress in the molecular design of recently investigated carborane derivatives in light of the widely accepted performance requirements for effective BNCT.

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“…Because of the short trajectories of these heavy particles (5–9 μm; approximately one cell diameter), radiation damage is limited to those cells that containing 10 B. Thus, side effects typically associated with ionizing radiation can be prevented if 10 B agents can be selectively targeted to tumor cells [ 1 , 2 , 3 , 4 , 5 , 6 ].…”

Section: Introductionmentioning

confidence: 99%

o-Carboranylalkoxy-1,3,5-Triazine Derivatives: Synthesis, Characterization, X-ray Structural Studies, and Biological Activity

et al. 2018

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Morpholine- and bis(2-methoxyethyl)amine-substituted 1,3,5-triazine derivatives containing an alkoxy-o-carborane in the 6-position of the triazine ring were successfully synthesized. The molecular structures of the methoxy- and ethoxy-o-carboranyl-1,3,5-triazines were established by X-ray crystallography. In vitro studies showed that the methylene bridged morpholine- and bis(2-methoxyethyl)amine-substituted o-carboranyl-1,3,5-triazines accumulated to high levels in B16 melanoma cells and exhibited higher cytotoxicity than p-boronophenylalanine.

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Glycoconjugates of polyhedral boron clusters

Cited by 26 publications

References 70 publications

Medicinal Chemistry of Boron-Bearing Compounds for BNCT- Glioma Treatment: Current Challenges and Perspectives

Medicinal Chemistry of Boron-Bearing Compounds for BNCT- Glioma Treatment: Current Challenges and Perspectives

Towards carborane-functionalised structures for the treatment of brain cancer

o-Carboranylalkoxy-1,3,5-Triazine Derivatives: Synthesis, Characterization, X-ray Structural Studies, and Biological Activity

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