Synthesis and characterization of carborane-functionalized hyperbranched polyester for boron neutron capture therapy

Year 2021, Volume: 6 Issue: 1, 252 - 262, 31.03.2021

Gülten Özçayan Yüksel Şahin A. Ernur Söylemez M. Elif Ünsal

https://doi.org/10.30728/boron.763317

Abstract

The purpose of this study is to synthesize new boron containing carrier compound for Boron Neutron Capture Therapy (BNCT) which is two-component radiation therapy method that especially is promising for the treatment of brain tumors and is being actively researched in many countries. For this research hyperbranched polyester (HBP), bifunctional p-carborane and carborane-functionalized HBP were synthesized. Dipentaerythritol was chosen as a core molecule of the HBP and esterified with dimethylol propionic acid. Observed characteristic ester bands and OH stretching band in the FTIR spectrum and the methyl & methylene peaks in the 1H NMR spectrum of HBP indicated that hyperbranched polyester synthesis was done successfully. A bifunctionalized p-carborane containing an acid group and a benzyl ether protected alcohol was prepared in three-step reactions. As a result of these reactions, a bifunctionalized p-carborane compound was produced with 60% yield. Then, the HBP was esterified with the bifunctional p-carborane. The characterization of the synthesized compounds was determined by FTIR and NMR spectra. The synthesis of carborane-functionalized HBP was confirmed by disappearance of HBP's OH groups and B-H stretching band observed in the FTIR spectrum of carborane-functionalized HBP and in addition, appearance of proton signals of HBP core, carborane linker and peripheral-protecting groups in the 1H-NMR spectrum. Finally, synthesized water-soluble carborane-containing HB carrying many boron atoms should be served as potential BNCT agents.

Keywords

Bnct, boron, carborane, esterification, hyperbranced polyester

Supporting Institution

Türkiye Atom Enerjisi Kurumu

Project Number

TAEK-A3.H2.P2.01 (2010)

Thanks

The author thanks for the support of the TAEK (Turkish Atomic Energy Authority) through TAEK-A3.H2.P2.01 project. Also, the author would like to express her gratitude and appreciation to Prof. Dr. Güngör GÜNDÜZ at Middle East Technical University for the helpful discussions about hyperbranched polyester synthesis.

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