Double functionalization of carbon nanotubes with purine and pyrimidine derivatives.

Herein, we have developed a synthetic strategy for the covalent double functionalization of single-walled carbon nanotubes (SWCNTs) with a combination of purine-pyrimidine and purine-purine nucleobase systems. The nucleobases were introduced on the sidewall of oxidized SWCNTs through 1,3-dipolar cycloaddition and by amidation of the carboxylic acids located at the tips and defect sites of the nanotubes. The new nanohybrids were characterized by transmission electron microscopy, thermogravimetric analysis, FTIR and Raman spectroscopy, magic-angle spinning NMR spectroscopy, and Kaiser test. The nucleobase/SWCNT conjugates can be envisaged for the modulation of the interactions with nucleic acids by means of base pairing, thereby opening new possibilities in the development of DNA/CNT nanobioconjugates.

[1]  J. Hirschinger,et al.  Chemical shift powder spectra enhanced by multiple-contact cross-polarization under slow magic-angle spinning. , 2013, Journal of magnetic resonance.

[2]  A. Bianco,et al.  Nucleobase-pairing triggers the self-assembly of uracil-ferrocene on adenine functionalized multi-walled carbon nanotubes , 2012 .

[3]  P. N. Day,et al.  On modeling biomolecular–surface nonbonded interactions: application to nucleobase adsorption on single-wall carbon nanotube surfaces , 2012, Nanotechnology.

[4]  A. Bianco,et al.  G-quartet type self-assembly of guanine functionalized single-walled carbon nanotubes. , 2012, Nanoscale.

[5]  F. Rius,et al.  Disruption of small double stranded DNA molecules on carbon nanotubes: A molecular dynamics study , 2012 .

[6]  F. Toma,et al.  Formation of efficient catalytic silver nanoparticles on carbon nanotubes by adenine functionalization. , 2011, Angewandte Chemie.

[7]  M. Prato,et al.  Functional motor recovery from brain ischemic insult by carbon nanotube-mediated siRNA silencing , 2011, Proceedings of the National Academy of Sciences.

[8]  F. Toma,et al.  Carbon nanotube-nucleobase hybrids: nanorings from uracil-modified single-walled carbon nanotubes. , 2011, Chemistry.

[9]  N. Hadipour,et al.  Covalent hybridization of CNT by thymine and uracil: A computational study , 2011, Journal of molecular modeling.

[10]  F. Toma,et al.  Polyamine functionalized carbon nanotubes: synthesis, characterization, cytotoxicity and siRNA binding , 2011 .

[11]  J. Zemek,et al.  Studies of oxidized carbon nanotubes in temperature range RT–630 °C by the infrared and electron spectroscopies , 2010 .

[12]  J. Coleman,et al.  Dispersion and Exfoliation of Nanotubes with Synthetic Oligonucleotides: Variation of Dispersion Efficiency and Oligo-Nanotube Interaction with Base Type , 2010 .

[13]  K Kostarelos,et al.  Promises, facts and challenges for carbon nanotubes in imaging and therapeutics. , 2009, Nature nanotechnology.

[14]  F. Toma,et al.  Synthesis and characterization of nucleobase-carbon nanotube hybrids. , 2009, Journal of the American Chemical Society.

[15]  Ming Zheng,et al.  DNA sequence motifs for structure-specific recognition and separation of carbon nanotubes , 2009, Nature.

[16]  Maurizio Prato,et al.  Synthesis and characterization of a carbon nanotube-dendron series for efficient siRNA delivery. , 2009, Journal of the American Chemical Society.

[17]  N. Zhang,et al.  Base-pairing mediated non-covalent polymers. , 2009, Chemical Society reviews.

[18]  M. Prato,et al.  Cancer therapy: Small 10/2009 , 2009 .

[19]  M. Prato,et al.  Antitumor activity and prolonged survival by carbon-nanotube-mediated therapeutic siRNA silencing in a human lung xenograft model. , 2009, Small.

[20]  Ya‐Ping Sun,et al.  Advances in Bioapplications of Carbon Nanotubes , 2009 .

[21]  Yixuan Wang.  Theoretical Evidence for the Stronger Ability of Thymine to Disperse SWCNT than Cytosine and Adenine: self-stacking of DNA bases vs their cross-stacking with SWCNT. , 2008, The journal of physical chemistry. C, Nanomaterials and interfaces.

[22]  M. Hersam.  Progress towards monodisperse single-walled carbon nanotubes. , 2008, Nature nanotechnology.

[23]  R. Varadarajan,et al.  Binding of nucleobases with single-walled carbon nanotubes: Theory and experiment , 2007, 0709.3071.

[24]  Ravindra Pandey,et al.  First-principles study of physisorption of nucleic acid bases on small-diameter carbon nanotubes , 2007, Nanotechnology.

[25]  R. Graupner.  Raman spectroscopy of covalently functionalized single‐wall carbon nanotubes , 2007 .

[26]  Jonathan L Sessler,et al.  Molecular recognition via base-pairing. , 2007, Chemical Society reviews.

[27]  Michael S Strano,et al.  Detection of DNA hybridization using the near-infrared band-gap fluorescence of single-walled carbon nanotubes. , 2006, Nano letters.

[28]  E. Tu,et al.  Label-free detection of DNA hybridization using carbon nanotube network field-effect transistors. , 2006, Proceedings of the National Academy of Sciences of the United States of America.

[29]  Alan Gelperin,et al.  DNA-decorated carbon nanotubes for chemical sensing , 2005, Nano letters.

[30]  H. Dai,et al.  Carbon nanotubes as multifunctional biological transporters and near-infrared agents for selective cancer cell destruction. , 2005, Proceedings of the National Academy of Sciences of the United States of America.

[31]  M. Prato,et al.  Binding and condensation of plasmid DNA onto functionalized carbon nanotubes: toward the construction of nanotube-based gene delivery vectors. , 2005, Journal of the American Chemical Society.

[32]  Stuart J Rowan,et al.  Nucleobases as supramolecular motifs. , 2005, Chemical Society reviews.

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

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

[35]  L. Ley,et al.  Functionalization of single-walled carbon nanotubes with (R-)oxycarbonyl nitrenes. , 2003, Journal of the American Chemical Society.

[36]  M. Zheng,et al.  DNA-assisted dispersion and separation of carbon nanotubes , 2003, Nature materials.

[37]  W. Pamler,et al.  Carbon Nanotubes in Microelectronic Applications , 2003, cond-mat/0410360.

[38]  Ijeoma F. Uchegbu,et al.  The Lower-Generation Polypropylenimine Dendrimers Are Effective Gene-Transfer Agents , 2002, Pharmaceutical Research.

[39]  I. Rouzina,et al.  Thermodynamics of cationic lipid binding to DNA and DNA condensation: roles of electrostatics and hydrophobicity. , 2002, Journal of the American Chemical Society.

[40]  P. Dash,et al.  Methodologies for monitoring nanoparticle formation by self-assembly of DNA with poly(l-lysine). , 2002, Analytical biochemistry.

[41]  M. Prato,et al.  Organic functionalization of carbon nanotubes. , 2002, Journal of the American Chemical Society.

[42]  M. Prato,et al.  Novel versatile fullerene synthons. , 2001, The Journal of organic chemistry.

[43]  Richard E. Smalley,et al.  Enhancement of adsorption inside of single-walled nanotubes: opening the entry ports , 2000 .

[44]  Jong-sang Park,et al.  Synthesis of a Barbell-like Triblock Copolymer, Poly(l-lysine) Dendrimer-block-Poly(ethylene glycol)-block-Poly(l-lysine) Dendrimer, and Its Self-Assembly with Plasmid DNA , 2000 .

[45]  R. Podgornik,et al.  The Structure of DNA−Liposome Complexes , 1997 .

[46]  G. Bodenhausen,et al.  NMR cross polarization by adiabatic passage through the Hartmann-Hahn condition (APHH) , 1994 .

[47]  T. Ichihashi,et al.  Single-shell carbon nanotubes of 1-nm diameter , 1993, Nature.

[48]  M. S. de Vries,et al.  Cobalt-catalysed growth of carbon nanotubes with single-atomic-layer walls , 1993, Nature.

[49]  S. Iijima.  Helical microtubules of graphitic carbon , 1991, Nature.

[50]  S. K. Vashist,et al.  Advances in carbon nanotube based electrochemical sensors for bioanalytical applications. , 2011, Biotechnology advances.

[51]  F. Cataldo,et al.  Medicinal chemistry and pharmacological potential of fullerenes and carbon nanotubes , 2008 .

[52]  M. Prato,et al.  Carbon nanotube cell translocation and delivery of nucleic acids in vitro and in vivo , 2008 .

[53]  P. Beer,et al.  Anion interaction with ferrocene-functionalised cyclic and open-chain polyaza and aza-oxa cycloalkanes , 2000 .

[54]  B. Fung,et al.  An improved broadband decoupling sequence for liquid crystals and solids. , 2000, Journal of magnetic resonance.

[55]  L. Huang,et al.  Protamine sulfate enhances lipid-mediated gene transfer , 1997, Gene Therapy.