Diverse morphologies of self-assemblies from homoditopic 1,18-nucleotide-appended bolaamphiphiles: effects of nucleobases and complementary oligonucleotides.
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 dC(20), dT(20), dA(20), and dG(20) 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/dC(20) 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/dT(20). Interestingly, helical nanorod structures are obtained from the binary self-assembly 4/dA(20), 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.
Iwaura
Rika
R
National Food Research Institute National Agriculture and Food Research Organization, 2-1-12 Kannondai, Tsukuba, Ibaraki, 305-8642, Japan. riwaura@affrc.go.jp
Iizawa
Tomohiko
T
Minamikawa
Hiroyuki
H
Ohnishi-Kameyama
Mayumi
M
Shimizu
Toshimi
T
D002942:Circular Dichroism; D018625:Microscopy, Atomic Force; D015394:Molecular Structure; D049329:Nanostructures / Q000737:chemistry*; D036103:Nanotechnology; D009841:Oligonucleotides / Q000737:chemistry*; D013501:Surface-Active Agents / Q000737:chemistry*
D009841:Oligonucleotides; D013501:Surface-Active Agents