Functionalizable Organic Nanochannels Based on Lipid Nanotubes:  Encapsulation and Nanofluidic Behavior of Biomacromolecules

Abstract

The amino groups on the inner surface of the nanotube that was self-assembled from unsymmetrical bolaamphiphile, N-(2-aminoethyl)-N‘-(β-d-glucopyranosyl)-icosanediamide 1, were modified covalently with a fluorescence donor dye. This functionalization of the nanotube inner surfaces has allowed us to achieve the construction of an optical recognition system for the encapsulation of guest molecules. Fluorescence resonance energy transfer (FRET) from the fluorescence donor located on the inner surface to the ferritin labeled with fluorescence acceptor enabled us to visualize the encapsulation and nanofluidic features of the ferritin in the nanochannel shaped by the hollow cylinder structure. By using this system, we were able to estimate the diffusion constants for ferritin and gold nanoparticles in the organic nanochannels on the basis of lipid nanotubes. We have also demonstrated that the size and surface charge of the nanochannel strongly affect the encapsulation behavior toward the biomacromolecules such as DNA and spherical proteins.

Self‐assembled organic nanotubes: Toward attoliter chemistry

“…6). Interestingly, packing-directed 15 and chiral molecular self-assembly 15 52,53 As a result, the obtained inner diameters of the nanotubes were found to have 80 and 20 nm, respectively (Fig. 6).…”

“…This finding remarkably contrasts to the view that the carboxylic-1(12) or amine-based amphiphiles 2(n) (n ¼ 12, 14, 16, and 17) that possess relatively shorter oligomethylene spacers has a tendency to form nanotubes or tape-like assemblies with antiparallel molecular packing, respectively. 48,52,53 Although certain tube-forming compounds self-assemble in elegant tubular self-assemblies with a monodisperse thickness of membrane wall, 20,56,57 the self-assembled organic nanotubes, which possess well-defined dimensions and also asymmetric feature characterized by different inner and outer surfaces, still remain little.…”

“…9). 53 On the other hand, the relatively narrower organic nanotube of 2(18) with 20 nm inner diameters cannot encapsulate the DNA. The persistence length of the double-stranded DNA is typically 50 nm long.…”

The Headgroup (A)Symmetry Strongly Determines the Aggregation Behavior of Single-Chain Phenylene-Modified Bolalipids and Their Miscibility with Classical Phospholipids

“…This asymmetry leads to two different orientations of the bolalipids in lamellar structures, either parallel or antiparallel. A parallel orientation of the bolalipids provokes the formation of rods, nanotubes [19][20][21] or nanotapes 22 with, e.g., a different curvature of the inner and outer surface of the nanotube. On the other hand, an antiparallel (interdigitated) orientation of the bolalipid results in the formation of monolayer-like aggregates.…”

Synthesis and characterization of nanoarchitectures from fatty acid derivatives of 2,6-diaminopyridine and 2-aminopyridine

“…Although related literature on further practical application of cardanol-based glycolipids is absent, its selfassembling properties have promoted the synthesis of several glycolipids such as monosaccharide esters with diamino-aromatic linkers [12], amygdalin-based esters [13] and dialkanoate derivative of sugar alcohols [14]. Unlike the carbon nanotubes (CNTs), organic nanotubes have excellent dispersibility in water and incorporate guest substance of over 10 nm in size, such as nucleic acids and proteins [15]. The organic nanotubes can provide suitable hollow cylindrical space for biomacromolecules that are at least 10 times larger in dimension as compared to macrocylic molecules used for host-guest study [16].…”