Dipeptide derived from benzylcystine forms unbranched nanotubes in aqueous solution
Abstract
Abstract
The essence of modern nanotechnology is manifested in the formation of well-ordered nanostructures by a process of self-association. Peptides are among the most useful building blocks for organic bionanostructures such as nanotubes, nanospheres, nanotapes, nanofibrils, and other different ordered structures at the nanoscale. Peptides are biocompatible, chemically diverse, and much more stable and can be readily synthesized on a large scale. Also, they have diverse application in biosensors, tissue engineering, drug delivery, etc. Here, we report a short cystine-based dipeptide, which spontaneously self-associates to form straight, unbranched nanotubes. Such self-assembled nanobiomaterials provide a novel possibility of designing new functional biomaterials with potential applications in nanobiotechnology. The formation of nanotubes in solution state has been demonstrated by atomic force microscopy and scanning electron microscopy. Infrared absorption and circular dichroism demonstrated the intermolecular β-sheet-like backbone hydrogen bonding in juxtaposing and stacking of aromatic side chains.
Keywords
- Nanotube,
- Dipeptide,
- π-π stacking,
- Cystine,
- Self-assembly
References
- Cui et al. (2001) Nanowire nanosensors for highly sensitive and selective detection of biological and chemical species 293(5533) (pp. 1289-1292) https://doi.org/10.1126/science.1062711
- Diehl et al. (2002) Self-assembled, deterministic carbon nanotube wiring networks 41(2) (pp. 353-356) https://doi.org/10.1002/1521-3773(20020118)41:2<353::AID-ANIE353>3.0.CO;2-Y
- Collins et al. (2001) Engineering carbon nanotubes and nanotube circuits using electrical breakdown 292(5517) (pp. 706-709) https://doi.org/10.1126/science.1058782
- Gao and Matsui (2005) Peptide-based nanotubes and their applications in bionanotechnology 17(17) (pp. 2037-2050) https://doi.org/10.1002/adma.200401849
- Wang et al. (2010) Facile assembly of size- and shape-tunable IV−VI nanocrystals into superlattices 26(24) (pp. 19129-19135) https://doi.org/10.1021/la103444h
- Whitesides (2005) Nanoscience, nanotechnology, and chemistry 1(2) (pp. 172-179) https://doi.org/10.1002/smll.200400130
- Martin and Kohli (2003) The emerging field of nanotube biotechnology (pp. 29-37) https://doi.org/10.1038/nrd988
- Bong et al. (2001) Self-assembling organic nanotubes 40(6) (pp. 988-1011) https://doi.org/10.1002/1521-3773(20010316)40:6<988::AID-ANIE9880>3.0.CO;2-N
- Gazit (2007) Self-assembled peptide nanostructures: the design of molecular building blocks and their technological utilization 36(8) (pp. 1263-1269) https://doi.org/10.1039/b605536m
- Lv et al. (2013) Self-assembly of double helical nanostructures inside carbon nanotubes
- Colombo et al. (2007) Peptide self-assembly at the nanoscale: a challenging target for computational and experimental biotechnology 25(5) (pp. 211-218) https://doi.org/10.1016/j.tibtech.2007.03.004
- Brea et al. (2004) Self-assembly of cyclic peptides in hydrogen-bonded nanotubes (pp. 3439-3457) Marcel Dekker
- Ghadiri et al. (1993) Self-assembling organic nanotubes based on a cyclic peptide architecture 366(6453) (pp. 324-327) https://doi.org/10.1038/366324a0
- Khazanovich et al. (1994) Nanoscale tubular ensembles with specified internal diameters. Design of a self-assembled nanotube with a 13 Å pore 116(13) (pp. 6011-6012) https://doi.org/10.1021/ja00092a079
- Ghadiri et al. (1994) Artificial transmembrane ion channels from self-assembling peptide nanotubes 369(6478) (pp. 301-304) https://doi.org/10.1038/369301a0
- Panciera et al. (2013) Design of stable β-sheet-based cyclic peptide assemblies assisted by metal coordination: selective homo- and heterodimer formation
- Amin et al. (2009) Artificially designed DNA nanostructures 4(3) (pp. 119-139) https://doi.org/10.1142/S1793292009001666
- Maity et al. (2011) Fabrication of hollow self-assembled peptide microvesicles and transition from sphere-to-rod structure 27(7) (pp. 3835-3841) https://doi.org/10.1021/la104461m
- Tao et al. (2011) Self-assembly of short Aβ(16–22) peptides: effect of terminal capping and the role of electrostatic interaction 27(6) (pp. 2723-2730) https://doi.org/10.1021/la1034273
- Tian et al. (2010) Peptide separation through a CB[8]-mediated supramolecular trap-and-release process 27(4) (pp. 1387-1390) https://doi.org/10.1021/la104346k
- Hauser and Zhang (2010) Designer self-assembling peptide nanofiber biological materials 39(8) (pp. 2780-2790) https://doi.org/10.1039/b921448h
- Banerji et al. (2012) Conformation and cytotoxicity of a tetrapeptide constellated with alternative d- and l-proline 2(17) (pp. 6744-6747) https://doi.org/10.1039/c2ra20616a
- Banerji et al. (2012) Synthesis, characterization and cytotoxicity study of magnetic (Fe3O4) nanoparticles and their drug conjugate 2(6) (pp. 2493-2497) https://doi.org/10.1039/c2ra01118b
- Rudra et al. (2012) Melatonin inhibits matrix metalloproteinase-9 activity by binding to its active site
10.1186/2193-8865-3-12