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<p>Two efficient synthetic procedures for charge-compensated cobalt bis(dicarbollide) conjugates with 4,4-difluoro-4-bora-3a,4a-diaza-<i>s</i>-indacene (BODIPY), in which the boron cluster is attached to the <i>meso</i> position of the dipyrrylmethene moiety were developed: (1) through the nucleophilic opening of cyclic oxonium derivatives of cobalt bis(dicarbollide) by BODIPYs modified with the benzyldimethylamino group; (2) through the synthesis of cobalt bis(dicarbollide) aldehydes followed by their condensation with 2,4-dimethylpyrrole, oxidation, and complexation with BF<sub>3</sub>•Et<sub>2</sub>O. The study of the optical properties of the BODIPY derivative with the benzyldimethylamino substituent and its boron-containing conjugates demonstrated that the attachment of the boron cluster enhances the fluorescence of BODIPY. Therefore, the synthesized compounds can be used for further biological assays as fluorescent boron neutron capture therapy agents to determine the distribution of boron in the body.</p>

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Synthesis of charge-compensated cobalt bis(dicarbollide) derivatives with BODIPY

  • 期刊论文

  • 发表日期：

    2025年11月1日

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  • A. A. Druzina,
  • N. V. Dudarova,
  • O. B. Zhidkova,
  • I. D. Kosenko,
  • I. B. Sivaev,
  • V. I. Bregadze

摘要

Two efficient synthetic procedures for charge-compensated cobalt bis(dicarbollide) conjugates with 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY), in which the boron cluster is attached to the meso position of the dipyrrylmethene moiety were developed: (1) through the nucleophilic opening of cyclic oxonium derivatives of cobalt bis(dicarbollide) by BODIPYs modified with the benzyldimethylamino group; (2) through the synthesis of cobalt bis(dicarbollide) aldehydes followed by their condensation with 2,4-dimethylpyrrole, oxidation, and complexation with BF3•Et2O. The study of the optical properties of the BODIPY derivative with the benzyldimethylamino substituent and its boron-containing conjugates demonstrated that the attachment of the boron cluster enhances the fluorescence of BODIPY. Therefore, the synthesized compounds can be used for further biological assays as fluorescent boron neutron capture therapy agents to determine the distribution of boron in the body.