Gene delivery by aminofullerenes: Structural requirements for efficient transfection

Hiroyuki Isobe, Waka Nakanishi, Naoki Tomita, Shigeki Jinno, Hiroto Okayama, Eiichi Nakamura

    Research output: Contribution to journalArticlepeer-review

    94 Citations (Scopus)

    Abstract

    A series of aminofullerenes that share a common structural motif have been synthesized and subjected to a systematic investigation of structure activity relationship regarding their ability for transient transfection and cytotoxicity. DNA-binding tests indicated that any water-soluble fullerene-bearing amino group would bind to double-stranded DNA. For these molecules to be effective transfection reagents, however, they require additional structural features. First, the molecule must be capable of producing submicrometer-sized fullerene/DNA aggregates that can be internalized into mammalian cells through endocytosis. Second, the molecule must be capable of releasing DNA as the aggregates are transferred into the cytoplasm. This can be achieved in at least two ways: by loss of the DNA-binding amino groups from the fullerene core, and by transformation of the amino groups to neutral groups such as amides. The screening experiments led us to identify the best reagent, a tetrapiperidinofullerene, that can be synthesized in two steps from fullerene, piperazine, and molecular oxygen, and that is more efficient at transfection than a commonly used lipid-based transfection reagent.

    Original languageEnglish
    Pages (from-to)167-175
    Number of pages9
    JournalChemistry - An Asian Journal
    Volume1
    Issue number1-2
    DOIs
    Publication statusPublished - 2006 Sep 20

    Keywords

    • Aggregation
    • Amphiphiles
    • Drug delivery
    • Fullerenes
    • Gene expression

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry

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