Functional single-walled carbon nanotubes/chitosan conjugate for tumor cells targeting

The application of single-walled carbon nanotubes (SWCNTs) in the field of biomedicine is becoming an exciting topic because of their flexible structure and propensity for chemical functionalization. In this assay, a novel noncovalently functional SWCNTs based on a natural biocompatible polymer chitosan has been developed for tumor cells targeting. First, SWCNTs were modified by chitosan (CHIT-SWCNT). Second, CHIT-SWCNT was coupled with fluorescein isothiocyanate (FITC), based on the reaction between the isothiocyanate group of FITC and the primary amino group of chitosan. Third, the FITC functionalized CHIT-SWCNT was conjugated with folic acid (FA) after activation with EDC/NHS, based on the reaction between the NHS group of FA and the primary free amino group of chitosan to construct the functional SWCNT/CHIT conjugate, CHIT-SWCNT-FA. The fluorescence CHIT-SWCNT-FA has been used to detect tumor cells with confocal microscopy imaging technology. Our experimental results indicate that the novel CHIT-SWCNT-FA is soluble and stable in PBS, and it can be readily transported inside tumor cells. Combining the intrinsic properties of carbon nanotubes and the versatility of chitosan, CHIT-SWCNT can be used as potential devices for targeted drug delivery and tumor cell sensing. The proposed assay could provide a feasible alternative to presently available functional SWCNTs in biological applications.

[1]  R. Hendren,et al.  Folate-mediated drug delivery: effect of alternative conjugation chemistry. , 1999, Journal of drug targeting.

[2]  Zhuang Liu,et al.  Carbon nanotubes as intracellular transporters for proteins and DNA: an investigation of the uptake mechanism and pathway. , 2006, Angewandte Chemie.

[3]  A. Domb,et al.  Chitosan chemistry and pharmaceutical perspectives. , 2004, Chemical reviews.

[4]  M. Rinaudo,et al.  Chitin and chitosan: Properties and applications , 2006 .

[5]  Maurizio Prato,et al.  Soluble carbon nanotubes. , 2003, Chemistry.

[6]  L. Dai,et al.  Chemistry of Carbon Nanotubes , 2003 .

[7]  S. Hudson,et al.  Review of vinyl graft copolymerization featuring recent advances toward controlled radical-based reactions and illustrated with chitin/chitosan trunk polymers. , 2001, Chemical reviews.

[8]  Feifan Zhou,et al.  Functional single-walled carbon nanotubes based on an integrin αvβ3 monoclonal antibody for highly efficient cancer cell targeting , 2009, Nanotechnology.

[9]  R. Bruce Weisman,et al.  SWCNT PEG-eggs: Single-walled carbon nanotubes in biocompatible shell-crosslinked micelles , 2007 .

[10]  Maogen Zhang,et al.  Carbon nanotube-chitosan system for electrochemical sensing based on dehydrogenase enzymes. , 2004, Analytical chemistry.

[11]  Philip S Low,et al.  Folate-mediated delivery of macromolecular anticancer therapeutic agents. , 2002, Advanced drug delivery reviews.

[12]  S. Hou,et al.  Amperometric glucose biosensor based on layer-by-layer assembly of multilayer films composed of chitosan, gold nanoparticles and glucose oxidase modified Pt electrode. , 2007, Biosensors & bioelectronics.

[13]  S. Hou,et al.  Amperometric glucose biosensor based on multilayer films via layer-by-layer self-assembly of multi-wall carbon nanotubes, gold nanoparticles and glucose oxidase on the Pt electrode. , 2007, Biosensors & bioelectronics.

[14]  Baoyan Wu,et al.  Layer-by-layer assemblies of chitosan/multi-wall carbon nanotubes and glucose oxidase for amperometric glucose biosensor applications , 2009 .

[15]  H. Dai,et al.  Soluble single-walled carbon nanotubes as longboat delivery systems for platinum(IV) anticancer drug design. , 2007, Journal of the American Chemical Society.

[16]  R. Smalley,et al.  Reversible water-solubilization of single-walled carbon nanotubes by polymer wrapping , 2001 .

[17]  C. Laurencin,et al.  Development of injectable thermogelling chitosan-inorganic phosphate solutions for biomedical applications. , 2007, Biomacromolecules.

[18]  M. Foldvari,et al.  Carbon nanotubes as functional excipients for nanomedicines: I. Pharmaceutical properties. , 2008, Nanomedicine : nanotechnology, biology, and medicine.

[19]  J. Xin,et al.  Decoration of carbon nanotubes with chitosan , 2005 .

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

[21]  Hui-Ming Cheng,et al.  The present status and key problems of carbon nanotube based polymer composites , 2007 .