Enhanced cellular uptake efficiency of DCM probes or SN38 conjugating with phenylboronic acids

Qiumeng Zhang; Rui Che; Wei Lu

doi:10.1016/j.bmc.2020.115377

Enhanced cellular uptake efficiency of DCM probes or SN38 conjugating with phenylboronic acids

Qiumeng Zhang, Rui Che, Wei Lu^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

High-level of sialic acid (SA) expression on the surface of cancer cells is observed extremely common. Phenylboronic acids (PBAs) have a high affinity with SA. The cellular uptake efficiency could be enhanced by the strategy of introducing PBA fragments to the compounds. In this work, we synthesized five new probes with the Dicyanomethylene-4H-pyran (DCM) fluorophore, three of them conjugated with different phenylboronic acid fragments. By cellular uptake experiments, DLCB and DLAB showed enhanced cellular uptake abilities compared with DLN and DLO. These two effective phenylboronic acid fragments were then conjugated with SN-38 and the conjugates showed enhanced cellular uptake abilities by 3-fold or 7-fold compared with irinotecan. In summary, the strategy of introducing 4-carboxyphenylboronic acid and 3-amino-benzoxaborole groups shows great potential in drug delivery system. Moreover, the released linkers between boric acid and drugs deserve further studies.

Original language	English
Article number	115377
Journal	Bioorganic and Medicinal Chemistry
Volume	28
Issue number	7
DOIs	https://doi.org/10.1016/j.bmc.2020.115377
State	Published - 1 Apr 2020

Keywords

Cellular uptake
Phenylboronic acid
Probe
SN38
Sialic acid

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmc.2020.115377

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@article{c38e33b5b29c465fa7274ab30166d346,

title = "Enhanced cellular uptake efficiency of DCM probes or SN38 conjugating with phenylboronic acids",

abstract = "High-level of sialic acid (SA) expression on the surface of cancer cells is observed extremely common. Phenylboronic acids (PBAs) have a high affinity with SA. The cellular uptake efficiency could be enhanced by the strategy of introducing PBA fragments to the compounds. In this work, we synthesized five new probes with the Dicyanomethylene-4H-pyran (DCM) fluorophore, three of them conjugated with different phenylboronic acid fragments. By cellular uptake experiments, DLCB and DLAB showed enhanced cellular uptake abilities compared with DLN and DLO. These two effective phenylboronic acid fragments were then conjugated with SN-38 and the conjugates showed enhanced cellular uptake abilities by 3-fold or 7-fold compared with irinotecan. In summary, the strategy of introducing 4-carboxyphenylboronic acid and 3-amino-benzoxaborole groups shows great potential in drug delivery system. Moreover, the released linkers between boric acid and drugs deserve further studies.",

keywords = "Cellular uptake, Phenylboronic acid, Probe, SN38, Sialic acid",

author = "Qiumeng Zhang and Rui Che and Wei Lu",

note = "Publisher Copyright: {\textcopyright} 2020 Elsevier Ltd",

year = "2020",

month = apr,

day = "1",

doi = "10.1016/j.bmc.2020.115377",

language = "英语",

volume = "28",

journal = "Bioorganic and Medicinal Chemistry",

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TY - JOUR

T1 - Enhanced cellular uptake efficiency of DCM probes or SN38 conjugating with phenylboronic acids

AU - Zhang, Qiumeng

AU - Che, Rui

AU - Lu, Wei

PY - 2020/4/1

Y1 - 2020/4/1

N2 - High-level of sialic acid (SA) expression on the surface of cancer cells is observed extremely common. Phenylboronic acids (PBAs) have a high affinity with SA. The cellular uptake efficiency could be enhanced by the strategy of introducing PBA fragments to the compounds. In this work, we synthesized five new probes with the Dicyanomethylene-4H-pyran (DCM) fluorophore, three of them conjugated with different phenylboronic acid fragments. By cellular uptake experiments, DLCB and DLAB showed enhanced cellular uptake abilities compared with DLN and DLO. These two effective phenylboronic acid fragments were then conjugated with SN-38 and the conjugates showed enhanced cellular uptake abilities by 3-fold or 7-fold compared with irinotecan. In summary, the strategy of introducing 4-carboxyphenylboronic acid and 3-amino-benzoxaborole groups shows great potential in drug delivery system. Moreover, the released linkers between boric acid and drugs deserve further studies.

AB - High-level of sialic acid (SA) expression on the surface of cancer cells is observed extremely common. Phenylboronic acids (PBAs) have a high affinity with SA. The cellular uptake efficiency could be enhanced by the strategy of introducing PBA fragments to the compounds. In this work, we synthesized five new probes with the Dicyanomethylene-4H-pyran (DCM) fluorophore, three of them conjugated with different phenylboronic acid fragments. By cellular uptake experiments, DLCB and DLAB showed enhanced cellular uptake abilities compared with DLN and DLO. These two effective phenylboronic acid fragments were then conjugated with SN-38 and the conjugates showed enhanced cellular uptake abilities by 3-fold or 7-fold compared with irinotecan. In summary, the strategy of introducing 4-carboxyphenylboronic acid and 3-amino-benzoxaborole groups shows great potential in drug delivery system. Moreover, the released linkers between boric acid and drugs deserve further studies.

KW - Cellular uptake

KW - Phenylboronic acid

KW - Probe

KW - SN38

KW - Sialic acid

UR - https://www.scopus.com/pages/publications/85079555794

U2 - 10.1016/j.bmc.2020.115377

DO - 10.1016/j.bmc.2020.115377

M3 - 文章

C2 - 32081629

AN - SCOPUS:85079555794

SN - 0968-0896

VL - 28

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 7

M1 - 115377

ER -

Enhanced cellular uptake efficiency of DCM probes or SN38 conjugating with phenylboronic acids

Abstract

Keywords

UN SDGs

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