Improvement of water solubility of mercaptoundecahydrododecaborate (Bsh)-peptides by conjugating with ethylene glycol linker and interaction with cyclodextrin

Mizuki Kitamatsu, Ayaka Nakamura-Tachibana, Yoshimichi Ishikawa, Hiroyuki Michiue

Research output: Contribution to journalArticlepeer-review

Abstract

We previously developed a conjugate consisting of10B cluster BSH and tri-arginine peptide (BSH-3R). This could potentially be used as a boron agent for boron neutron capture therapy; however, it possesses poor water solubility and thus needs to be improved for use as medicine. In this study, we devised several means of improving the water solubility of BSH-3R. As one of them, we used cyclodextrin (CD), which was expected to improve the water solubility resulting from interaction of the BSH-3R with CD. We evaluated the solubility of BSH-3R in aqueous CD solution by using reverse-phase high-performance liquid chromatography. As we expected, the solubility of BSH-3R was increased in a manner dependent on the addition of β-CD and γ-CD in aqueous solution. Furthermore, we synthesized BSH conjugated to oligoarginine having various chain lengths (BSH-nR) and BSH-3R with ethylene glycol linkers introduced between BSH and 3R (BSH-nEg-3R). The water solubility of these BSH peptides was also evaluated and the results showed that the introduction of nEg to BSH-3R markedly improved the water solubility. Furthermore, we found that the water solubility of these peptides can be further improved by also applying CD.

Original languageEnglish
Article number167
Pages (from-to)1-11
Number of pages11
JournalProcesses
Volume9
Issue number1
DOIs
Publication statusPublished - Jan 2021

Keywords

  • BSH
  • Cell-penetrating peptide
  • Cyclodextrin
  • Ethylene glycol

ASJC Scopus subject areas

  • Bioengineering
  • Chemical Engineering (miscellaneous)
  • Process Chemistry and Technology

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