Enhancing Membrane Permeability of Fluorescein-Type Chromophore Through Covalent Attachment of Chlorinated Dodecaborate

Hibiki Nakamura; Satoshi Yamamoto; Yumiko K. Kawamura; Taro Kitazawa; Mutsumi Kimura; Yu Kitazawa

doi:10.3390/molecules29225416

Enhancing Membrane Permeability of Fluorescein-Type Chromophore Through Covalent Attachment of Chlorinated Dodecaborate

Hibiki Nakamura, Satoshi Yamamoto, Yumiko K. Kawamura, Taro Kitazawa^*, Mutsumi Kimura, Yu Kitazawa^*

^*Corresponding author for this work

Department of Molecular Biology and Genetics - Neurobiology

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

1 Citation (Scopus)

Abstract

Anionic boron clusters, such as [B₁₂X₁₂]²⁻ (X = Cl, Br, I), have attracted attention in pharmaceuticals due to their unique superchaotropic properties. In particular, [B₁₂Br₁₂]²⁻ (1) has demonstrated strong interactions with biomolecules, facilitating cargo translocation across plasma membranes. In this study, we investigated the effect of covalently attaching chlorinated dodecaborate moiety [B₁₂Cl₁₁O-]²⁻ to 6-carboxyfluorescein (6-FAM) (3) via a PEG3 linker to form conjugate (4). We compared the membrane permeability of this covalent conjugate with that of non-covalent interactions between 6-FAM (3) and [B₁₂Cl₁₂]²⁻ (2). Live-cell fluorescence imaging revealed that the covalent conjugate exhibited enhanced membrane permeability and water solubility while maintaining low cytotoxicity. These results highlight the potential of covalent conjugation with boron clusters for improving the cellular uptake of hydrophilic cargos.

Original language	English
Article number	5416
Journal	Molecules
Volume	29
Issue	22
ISSN	1420-3049
DOIs	https://doi.org/10.3390/molecules29225416
Publication status	Published - Nov 2024

Keywords

boron cluster
chaotropic anion
membrane transport

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10.3390/molecules29225416

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title = "Enhancing Membrane Permeability of Fluorescein-Type Chromophore Through Covalent Attachment of Chlorinated Dodecaborate",

abstract = "Anionic boron clusters, such as [B12X12]2− (X = Cl, Br, I), have attracted attention in pharmaceuticals due to their unique superchaotropic properties. In particular, [B12Br12]2− (1) has demonstrated strong interactions with biomolecules, facilitating cargo translocation across plasma membranes. In this study, we investigated the effect of covalently attaching chlorinated dodecaborate moiety [B12Cl11O-]2− to 6-carboxyfluorescein (6-FAM) (3) via a PEG3 linker to form conjugate (4). We compared the membrane permeability of this covalent conjugate with that of non-covalent interactions between 6-FAM (3) and [B12Cl12]2− (2). Live-cell fluorescence imaging revealed that the covalent conjugate exhibited enhanced membrane permeability and water solubility while maintaining low cytotoxicity. These results highlight the potential of covalent conjugation with boron clusters for improving the cellular uptake of hydrophilic cargos.",

keywords = "boron cluster, chaotropic anion, membrane transport",

author = "Hibiki Nakamura and Satoshi Yamamoto and Kawamura, {Yumiko K.} and Taro Kitazawa and Mutsumi Kimura and Yu Kitazawa",

note = "Publisher Copyright: {\textcopyright} 2024 by the authors.",

year = "2024",

month = nov,

doi = "10.3390/molecules29225416",

language = "English",

volume = "29",

journal = "Molecules",

issn = "1420-3049",

publisher = "M D P I AG",

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Enhancing Membrane Permeability of Fluorescein-Type Chromophore Through Covalent Attachment of Chlorinated Dodecaborate. / Nakamura, Hibiki; Yamamoto, Satoshi; Kawamura, Yumiko K. et al.
In: Molecules, Vol. 29, No. 22, 5416, 11.2024.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

TY - JOUR

T1 - Enhancing Membrane Permeability of Fluorescein-Type Chromophore Through Covalent Attachment of Chlorinated Dodecaborate

AU - Nakamura, Hibiki

AU - Yamamoto, Satoshi

AU - Kawamura, Yumiko K.

AU - Kitazawa, Taro

AU - Kimura, Mutsumi

AU - Kitazawa, Yu

PY - 2024/11

Y1 - 2024/11

N2 - Anionic boron clusters, such as [B12X12]2− (X = Cl, Br, I), have attracted attention in pharmaceuticals due to their unique superchaotropic properties. In particular, [B12Br12]2− (1) has demonstrated strong interactions with biomolecules, facilitating cargo translocation across plasma membranes. In this study, we investigated the effect of covalently attaching chlorinated dodecaborate moiety [B12Cl11O-]2− to 6-carboxyfluorescein (6-FAM) (3) via a PEG3 linker to form conjugate (4). We compared the membrane permeability of this covalent conjugate with that of non-covalent interactions between 6-FAM (3) and [B12Cl12]2− (2). Live-cell fluorescence imaging revealed that the covalent conjugate exhibited enhanced membrane permeability and water solubility while maintaining low cytotoxicity. These results highlight the potential of covalent conjugation with boron clusters for improving the cellular uptake of hydrophilic cargos.

AB - Anionic boron clusters, such as [B12X12]2− (X = Cl, Br, I), have attracted attention in pharmaceuticals due to their unique superchaotropic properties. In particular, [B12Br12]2− (1) has demonstrated strong interactions with biomolecules, facilitating cargo translocation across plasma membranes. In this study, we investigated the effect of covalently attaching chlorinated dodecaborate moiety [B12Cl11O-]2− to 6-carboxyfluorescein (6-FAM) (3) via a PEG3 linker to form conjugate (4). We compared the membrane permeability of this covalent conjugate with that of non-covalent interactions between 6-FAM (3) and [B12Cl12]2− (2). Live-cell fluorescence imaging revealed that the covalent conjugate exhibited enhanced membrane permeability and water solubility while maintaining low cytotoxicity. These results highlight the potential of covalent conjugation with boron clusters for improving the cellular uptake of hydrophilic cargos.

KW - boron cluster

KW - chaotropic anion

KW - membrane transport

U2 - 10.3390/molecules29225416

DO - 10.3390/molecules29225416

M3 - Journal article

C2 - 39598805

AN - SCOPUS:85210574422

SN - 1420-3049

VL - 29

JO - Molecules

JF - Molecules

IS - 22

M1 - 5416

ER -

Enhancing Membrane Permeability of Fluorescein-Type Chromophore Through Covalent Attachment of Chlorinated Dodecaborate

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Keywords

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