Synthesis and Biological Properties of Water-Soluble p-Boronophenylalanine Derivatives. Relationship between Water Solubility, Cytotoxicity, and Cellular Uptake

Hisao Nemoto, Jianping Cai, Naoki Asao, Satoshi Iwamoto, Yoshinori Yamamoto

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    54 Citations (Scopus)

    Abstract

    Water-soluble p-boronophenylalanine (BPA) derivatives having cascade polyols, the monohydroxy derivative BPA(OH) (4), the dihydroxy analogue BPA(OH)2 (5), and the tetrahydroxy analogue BPA(OH)4 (6), were synthesized in order to elucidate a relationship between the molecular structures and the cellular uptake. Biological properties of these compounds in addition to BPA (1) itself were investigated. Water solubility increased in the order of BPA < BPA(OH) ≥ BPA(OH)2 > BPA(OH)4. Cytotoxicity to B-16 melanoma and TIG hybrobrast cells decreased in the order of BPA ≫ BPA(OH) ≥ BPA(OH)2 > BPA(OH)4. The cellular uptake by both B-16 and TIG cells decreased in the order of BPA > BPA(OH) ≥ BPA(OH)2 > BPA(OH)4, whereas the uptake ratio of B-16/TIG increased in the order of BPA < BPA(OH) ≤ BPA(OH)2 < BPA(OH)4. The latter ratio indicates the selectivity on the uptake by a cancer to normal cell.

    Original languageEnglish
    Pages (from-to)1673-1678
    Number of pages6
    JournalJournal of Medicinal Chemistry
    Volume38
    Issue number10
    DOIs
    Publication statusPublished - 1995 May 1

    ASJC Scopus subject areas

    • Molecular Medicine
    • Drug Discovery

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