Shortening and dispersion of single-walled carbon nanotubes upon interaction with mixed supramolecular compounds

Abstract Congo red (CR) dye molecules self-associate in water solutions creating ribbon-like supramolecular structures that can bind various aromatic compounds by intercalation, forming mixed supramolecular systems. Mixed supramolecular systems, such as CR-doxorubicin and CR-Evans blue, interact with the surface of carbon nanotubes, leading to their stiffening and ultimately to their breaking and shortening. This work presents a simple method of obtaining short and straight carbon nanotubes with significantly better dispersion in aqueous solutions and consequently improved usability in biological systems.

[1]  S. V. Anisimov,et al.  Congo red and protein aggregation in neurodegenerative diseases , 2007, Brain Research Reviews.

[2]  I Roterman,et al.  Evidence that supramolecular Congo red is the sole ligation form of this dye for L chain lambda derived amyloid proteins. , 2001, Folia histochemica et cytobiologica.

[3]  Y. Nodasaka,et al.  Influence of length on cytotoxicity of multi-walled carbon nanotubes against human acute monocytic leukemia cell line THP-1 in vitro and subcutaneous tissue of rats in vivo. , 2005, Molecular bioSystems.

[4]  H. Fenniri,et al.  Nanotechnology-based drug delivery systems , 2007, Journal of occupational medicine and toxicology.

[5]  Aiguo Shen,et al.  Water-soluble single-walled carbon nanotubes via noncovalent functionalization by a rigid, planar and conjugated diazo dye , 2006 .

[7]  Irena Roterman-Konieczna,et al.  The use of Titan yellow dye as a metal ion binding marker for studies on the formation of specific complexes by supramolecular Congo red , 2015, Bio Algorithms Med Syst..

[8]  M. Prato,et al.  Functionalized carbon nanotubes for plasmid DNA gene delivery. , 2004, Angewandte Chemie.

[9]  A. C. Crooke,et al.  The determination of plasma volume by the Evans blue method , 1942, The Journal of physiology.

[10]  M. Prato,et al.  Translocation mechanisms of chemically functionalised carbon nanotubes across plasma membranes. , 2012, Biomaterials.

[11]  J. Wallace DIAGNOSIS OF AMYLOID DISEASE BY THE INTRAVENOUS INJECTION OF CONGO-RED. , 1932 .

[12]  Leszek Konieczny,et al.  Self‐assembly of Congo Red—A theoretical and experimental approach to identify its supramolecular organization in water and salt solutions , 1998 .

[13]  T. Mustelin,et al.  Dispersion of pristine single-walled carbon nanotubes in water by a thiolated organosilane: application in supramolecular nanoassemblies. , 2006, The journal of physical chemistry. B.

[14]  Seong-Rin Lim,et al.  Effect of the addition mode of carbon nanotubes for the production of chitosan hydrogel core-shell beads on adsorption of Congo red from aqueous solution. , 2011, Bioresource technology.

[15]  James Hope,et al.  Synthesis and evaluation of analogues of Congo red as potential compounds against transmissible spongiform encephalopathies. , 2003, European journal of medicinal chemistry.

[16]  M. Szlachta,et al.  Adsorption of methylene blue and Congo red from aqueous solution by activated carbon and carbon nanotubes. , 2013, Water science and technology : a journal of the International Association on Water Pollution Research.

[17]  H. Dai,et al.  Nanotube molecular transporters: internalization of carbon nanotube-protein conjugates into Mammalian cells. , 2004, Journal of the American Chemical Society.

[18]  M. Prato,et al.  Chemistry of carbon nanotubes. , 2006, Chemical reviews.

[19]  Hongjie Dai,et al.  Supramolecular Chemistry on Water- Soluble Carbon Nanotubes for Drug Loading and Delivery , 2007 .

[20]  I. Roterman,et al.  In vivo accumulation of self-assembling dye Congo red in an area marked by specific immune complexes: possible relevance to chemotherapy. , 2004, Folia histochemica et cytobiologica.

[21]  I. Roterman,et al.  Supramolecular ligands: monomer structure and protein ligation capability. , 1998, Biochimie.

[22]  Leszek Konieczny,et al.  An approach to understand the complexation of supramolecular dye Congo red with immunoglobulin L chain λ , 2005, Biopolymers.

[23]  A. Cuschieri,et al.  Can the properties of carbon nanotubes influence their internalization by living cells , 2008 .

[24]  R. Haddon,et al.  Water soluble single-walled carbon nanotubes inhibit stimulated endocytosis in neurons. , 2008, Nano letters.

[25]  M. Prato,et al.  Cellular uptake of functionalized carbon nanotubes is independent of functional group and cell type. , 2007, Nature nanotechnology.

[26]  C. Bertozzi,et al.  A cell nanoinjector based on carbon nanotubes , 2007, Proceedings of the National Academy of Sciences.

[27]  I Roterman,et al.  Bis azo dyes--studies on the mechanism of complex formation with IgG modulated by heating or antigen binding. , 1993, Journal of physiology and pharmacology : an official journal of the Polish Physiological Society.

[28]  Leszek Konieczny,et al.  The structure and protein binding of amyloid-specific dye reagents. , 2003, Acta biochimica Polonica.

[29]  M. Prato,et al.  Translocation of bioactive peptides across cell membranes by carbon nanotubes. , 2004, Chemical communications.