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Diverse Morphologies of Self-Assemblies from Homoditopic 1,18-Nucleotide-Appended Bolaamphiphiles: Effects of Nucleobases and Complementary Oligonucleotides

Authors

  • Rika Iwaura,

    Corresponding author
    1. National Food Research Institute (NFRI) National Agriculture and Food Research Organization (NARO) 2-1-12 Kannondai, Tsukuba, Ibaraki, 305-8642 (Japan)
    2. Precursory Research for Embryonic Science and Technology (PRESTO) Japan Science and Technology Agency (JST) 4-1-8 Honcho Kawaguchi, Saitama, 332-0012 (Japan)
    • National Food Research Institute (NFRI) National Agriculture and Food Research Organization (NARO) 2-1-12 Kannondai, Tsukuba, Ibaraki, 305-8642 (Japan).
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  • Tomohiko Iizawa,

    1. National Food Research Institute (NFRI) National Agriculture and Food Research Organization (NARO) 2-1-12 Kannondai, Tsukuba, Ibaraki, 305-8642 (Japan)
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  • Hiroyuki Minamikawa,

    1. Nanotube Research Center (NTRC) National Institute of Advanced Industrial Science and Technology Tsukuba Central 5, 1-1-1 Higashi Tsukuba Ibaraki, 305-8565 (Japan)
    2. Solution-Oriented Research for Science and Technology (SORST) Japan Science and Technology Agency (JST) 4-1-8 Honcho Kawaguchi, Saitama, 332-0012 (Japan)
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  • Mayumi Ohnishi-Kameyama,

    1. National Food Research Institute (NFRI) National Agriculture and Food Research Organization (NARO) 2-1-12 Kannondai, Tsukuba, Ibaraki, 305-8642 (Japan)
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  • Toshimi Shimizu

    1. Nanotube Research Center (NTRC) National Institute of Advanced Industrial Science and Technology Tsukuba Central 5, 1-1-1 Higashi Tsukuba Ibaraki, 305-8565 (Japan)
    2. Solution-Oriented Research for Science and Technology (SORST) Japan Science and Technology Agency (JST) 4-1-8 Honcho Kawaguchi, Saitama, 332-0012 (Japan)
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Abstract

The synthesis of 1,18-nucleotide-appended bolaamphiphiles (1, 2, 4, and 6) is reported, in which a 3′-phosphorylated guanidine, adenosine, thymidine, or cytidine is connected to each end of an octadecamethylene chain. Single-component self-assemblies and binary self-assemblies with the complementary oligonucleotides dC20, dT20, dA20, and dG20 are studied by atomic force microscopy, powder X-ray diffraction analysis, temperature-dependent UV absorption, circular dichroism, and attenuated total-reflection Fourier-transform infrared spectroscopy. The single-component self-assembly of 1 forms a two-dimensional sheet, whereas the binary self-assembly 1/dC20 gives helical nanofibers. Non-helical nanofibers are observed for the single-component self-assemblies of 2 and 4, and helical nanofibers form from the binary self-assembly 2/dT20. Interestingly, helical nanorod structures are obtained from the binary self-assembly 4/dA20, and the aligned nanorods form a nematic phase. The single-component and binary self-assemblies from 6 give unilamellar vesicles owing to a lack of stacking interaction between the cytosine moieties.

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