Abstract
Introduction of a bis(isopropylidene)-protected 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 as selective agents for boron neutron capture therapy (BNCT). Bearing either a carboxylic acid or primary amine as a functional group, these compounds are highly versatile and thus largely extend the possible coupling strategies with suitable biomolecules. Modification of the gastrin-releasing peptide receptor (GRPR) selective agonist [d-Phe6, β-Ala11, Ala13, Nle14]Bn(6-14) with the carboxylic acid derivative yielded a bioconjugate with an optimal receptor activation and internalisation profile. This demonstrates the great potential of this approach for the development of novel boron delivery agents.
Highlights
Since the first report by Locher in 1936, boron neutron capture therapy (BNCT) has been developed as a very promising approach for cancer treatment.1 It combines two non-toxic components to produce cytotoxic species, which are able to destroy malignant tissue
4,6-bis(1,7-dicarba-closo-dodecaboran-9-ylthio)-1,3,5-triazine [2], which was synthesised from 9-mercapto-(1,7-dicarba-closododecaborane)(12) [1] and cyanuric chloride
By modifying s-triazine derivatives with a galactopyranosyl moiety the modular system based on readily available building blocks like 9-mercapto-1,7-dicarba-closo-dodecaborane [1] and cyanuric chloride was further extended to compounds with reduced hydrophobicity
Summary
Since the first report by Locher in 1936, boron neutron capture therapy (BNCT) has been developed as a very promising approach for cancer treatment.1 It combines two non-toxic components to produce cytotoxic species, which are able to destroy malignant tissue. Tuning a modular system – synthesis and characterisation of a boron-rich s-triazine-based carboxylic acid and amine bearing a galactopyranosyl moiety Tuning a modular system – synthesis and characterisation of a boron-rich s-triazine-based Cite this: Dalton Trans., 2020, 49, 57 carboxylic acid and amine bearing a galactopyranosyl moiety† The introduction of the two 9-mercapto-meta-carborane clusters [1] was achieved with K2CO3 as base resulting in almost quantitative formation of tert-butyl-N-[4,6-bis(1,7-dicarba-closo-dodecaboran-9-ylthio)-
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