Antibody covalent immobilization on carbon nanotubes and assessment of antigen binding.

Controlling the covalent bonding of antibodies onto functionalized carbon nanotubes is a key step in the design and preparation of nanotube-based conjugates for targeting cancer cells. For this purpose, an anti-MUC1 antibody (Ab) is linked to both multi-walled (MWCNTs) and double-walled carbon nanotubes (DWCNTs) using different synthetic strategies. The presence of the Ab attached to the nanotubes is confirmed by gel electrophoresis and thermogravimetric analysis. Most importantly, molecular recognition of the antigen by surface plasmon resonance is able to determine similar Ab binding capacities for both Ab-DWCNTs and Ab-MWCNTs. These results are very relevant for the design of future receptor-targeting strategies using chemically functionalized carbon nanotubes.

[1]  Giorgia Pastorin,et al.  Crucial Functionalizations of Carbon Nanotubes for Improved Drug Delivery: A Valuable Option? , 2009, Pharmaceutical Research.

[2]  N. Peat,et al.  Molecular cloning and expression of human tumor-associated polymorphic epithelial mucin. , 1990, The Journal of biological chemistry.

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

[4]  Maurizio Prato,et al.  Functionalized carbon nanotubes for probing and modulating molecular functions. , 2010, Chemistry & biology.

[5]  H. Dai,et al.  Targeted single-wall carbon nanotube-mediated Pt(IV) prodrug delivery using folate as a homing device. , 2008, Journal of the American Chemical Society.

[6]  F. Toma,et al.  Potentiometric titration as a straightforward method to assess the number of functional groups on shortened carbon nanotubes , 2010 .

[7]  M. Prato,et al.  Adsorption of carbon nanotubes on active carbon microparticles , 2008 .

[8]  J. S. Gutkind,et al.  Nano Delivers Big: Designing Molecular Missiles for Cancer Therapeutics , 2011, Pharmaceutics.

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

[10]  C. Gaillard,et al.  Carbon nanotube‐coupled cell adhesion peptides are non‐immunogenic: a promising step toward new biomedical devices , 2011, Journal of peptide science : an official publication of the European Peptide Society.

[11]  Douglas R. Kauffman,et al.  Carbon nanotube gas and vapor sensors. , 2008, Angewandte Chemie.

[12]  Y. Niv,et al.  MUC1 and colorectal cancer pathophysiology considerations. , 2008, World journal of gastroenterology.

[13]  M. Prato,et al.  Functionalized carbon nanotubes in drug design and discovery. , 2008, Accounts of chemical research.

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

[15]  J. McFadden,et al.  Triple functionalisation of single-walled carbon nanotubes with doxorubicin, a monoclonal antibody, and a fluorescent marker for targeted cancer therapy , 2009 .

[16]  M. Prato,et al.  Amino acid functionalisation of water soluble carbon nanotubes. , 2002, Chemical communications.

[17]  G. Ellman,et al.  Tissue sulfhydryl groups. , 1959, Archives of biochemistry and biophysics.

[18]  Austin D. Swafford,et al.  Thermal ablation of tumor cells with antibody-functionalized single-walled carbon nanotubes , 2008, Proceedings of the National Academy of Sciences.

[19]  M. Endo,et al.  Carbon nanotubes: biomaterial applications. , 2009, Chemical Society reviews.

[20]  Ya‐Ping Sun,et al.  Immuno‐Carbon Nanotubes and Recognition of Pathogens , 2005, Chembiochem : a European journal of chemical biology.

[21]  Giada Cellot,et al.  Carbon Nanotubes Carrying Cell‐Adhesion Peptides do not Interfere with Neuronal Functionality , 2009 .

[22]  M. Prato,et al.  Synthesis, structural characterization, and immunological properties of carbon nanotubes functionalized with peptides. , 2003, Journal of the American Chemical Society.

[23]  Ching-An Peng,et al.  In vitro photothermal destruction of neuroblastoma cells using carbon nanotubes conjugated with GD2 monoclonal antibody , 2009, Nanotechnology.

[24]  Stanislaus S. Wong,et al.  Functionalized single-walled carbon nanotubes as rationally designed vehicles for tumor-targeted drug delivery. , 2008, Journal of the American Chemical Society.

[25]  D. Guldi,et al.  Covalent and noncovalent phthalocyanine-carbon nanostructure systems: synthesis, photoinduced electron transfer, and application to molecular photovoltaics. , 2010, Chemical reviews.

[26]  R. B. Merrifield,et al.  Quantitative monitoring of solid-phase peptide synthesis by the ninhydrin reaction. , 1981, Analytical biochemistry.

[27]  D. Scheinberg,et al.  Tumor Targeting with Antibody-Functionalized, Radiolabeled Carbon Nanotubes , 2007, Journal of Nuclear Medicine.

[28]  J W Hershey,et al.  Methyl 4-mercaptobutyrimidate as a cleavable cross-linking reagent and its application to the Escherichia coli 30S ribosome. , 1973, Biochemistry.

[29]  David A Scheinberg,et al.  Imaging and treating tumor vasculature with targeted radiolabeled carbon nanotubes , 2010, International journal of nanomedicine.

[30]  D. Tasis,et al.  Current progress on the chemical modification of carbon nanotubes. , 2010, Chemical reviews.

[31]  James F Rusling,et al.  Targeted killing of cancer cells in vivo and in vitro with EGF-directed carbon nanotube-based drug delivery. , 2009, ACS nano.

[32]  R. Cavicchi,et al.  Anti-HER2 IgY antibody-functionalized single-walled carbon nanotubes for detection and selective destruction of breast cancer cells , 2008, BMC Cancer.

[33]  Robert N. Azad,et al.  Specific thermal ablation of tumor cells using single‐walled carbon nanotubes targeted by covalently‐coupled monoclonal antibodies , 2009, International journal of cancer.

[34]  Liang Zhao,et al.  P-glycoprotein antibody functionalized carbon nanotube overcomes the multidrug resistance of human leukemia cells. , 2010, ACS nano.

[35]  E. Kaiser,et al.  Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. , 1970, Analytical biochemistry.

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

[37]  R. Traut,et al.  Addition of sulfhydryl groups to Escherichia coli ribosomes by protein modification with 2-iminothiolane (methyl 4-mercaptobutyrimidate). , 1978, Biochemistry.

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

[39]  H. Gronemeyer,et al.  Multivalent DR5 peptides activate the TRAIL death pathway and exert tumoricidal activity. , 2010, Cancer research.

[40]  M. Prato,et al.  Organic functionalisation and characterisation of single-walled carbon nanotubes. , 2009, Chemical Society reviews.

[41]  F. Toma,et al.  Enhanced anticancer activity of multi-walled carbon nanotube-methotrexate conjugates using cleavable linkers. , 2010, Chemical communications.

[42]  M. Prato,et al.  The alluring potential of functionalized carbon nanotubes in drug discovery , 2010, Expert opinion on drug discovery.

[43]  M. Terrones,et al.  Protein immobilization on carbon nanotubes via a two-step process of diimide-activated amidation , 2004 .

[44]  H. Dai,et al.  Carbon nanotubes in biology and medicine: In vitro and in vivo detection, imaging and drug delivery , 2009, Nano research.

[45]  Filip Braet,et al.  Carbon nanomaterials in biosensors: should you use nanotubes or graphene? , 2010, Angewandte Chemie.

[46]  Y. Gun’ko,et al.  Recent Advances in Research on Carbon Nanotube–Polymer Composites , 2010, Advanced materials.

[47]  Ching-An Peng,et al.  Photothermolysis of glioblastoma stem-like cells targeted by carbon nanotubes conjugated with CD133 monoclonal antibody. , 2011, Nanomedicine : nanotechnology, biology, and medicine.

[48]  S. Gendler,et al.  Molecular cloning and analysis of the mouse homologue of the tumor-associated mucin, MUC1, reveals conservation of potential O-glycosylation sites, transmembrane, and cytoplasmic domains and a loss of minisatellite-like polymorphism. , 1991, The Journal of biological chemistry.