Abstract
The approach to the preparation of fluorescein-labeled single-walled carbon nanotubes was proposed. The investigation of physico-chemical properties of obtained modified nanotubes was performed. The method of the design of non-covalent hybrids of fluorescein-labeled carbon nanotubes with nucleic acid fragments containing pyrene residues at 5′-termini was developed. This method is based on stacking interactions of pyrene residues with carbon nanotubes surface. The effect of carbon nanotubes functionalization type on the efficacy of sorption of pyrene conjugates of oligonucleotides was examined.
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Abbreviations
- CNT:
-
carbon nanotube
- DMF:
-
N,N-dimethylformamide
- EDC:
-
1-ethyl-3-[3-(dimethylamino)-propyl]carbodiimide
- FITC:
-
fluorescein isothiocyanate
- HMDA:
-
hexamethylenediamine
- PAMAM:
-
polyamidoamine dendrimer
- SWCNT:
-
single-walled carbon nanotube
- TEA:
-
triethylamine
References
D. Tasis, N. Tagmatarchis, A. Bianco, and M. Prato, “Chemistry of Carbon Nanotubes,” Chem. Rev. 106, 1105–1136 (2006).
D. Eder, “Carbon Nanotube-Inorganic Hybrids,” Chem. Rev. 110, 1348–1385 (2010).
D. Cui, “Advances and Prospects on Biomolecules Functionalized Carbon Nanotubes,” J. Nanosci. Nanotechno l7, 1298–1314 (2007).
C. Klumpp, K. Kostarelos, M. Prato, and A. Bianco, “Functionalized Carbon Nanotubes as Emerging Nanovectors for the Delivery of Therapeutics,” Biochim. Biophys. Acta 1758, 404–412 (2006).
M. Foldvari and M. Bagonluri, “Carbon Nanotubes as Functional Excipients for Nanomedicines: I. Pharmaceutical Properties,” Nanomed.: NBM 4, 173–182 (2008).
M. Foldvari and M. Bagonluri, “Carbon Nanotubes as Functional Excipients for Nanomedicines: II. Drug Delivery and Biocompatibility Issues,” Nanomed.: NBM 4, 183–200 (2008).
L. Lacerda, A. Bianco, M. Prato, and K. Kostarelos, “Carbon Nanotubes as Nanomedicines: From Toxicology to Pharmacology,” Adv. Drug Deliv. Rev. 58, 1460–1470 (2006).
W. Wei, A. Sethuraman, C. Jin, N. A. Monteiro-Riviere, and R. J. Narayan, “Biological Properties of Carbon Nanotubes,” J. Nanosci. Nanotechnol. 7, 1284–1297 (2007).
A. Bianco, K. Kostarelos, and M. Prato, “Applications of Carbon Nanotubes in Drug Delivery,” Curr. Opin. Chem. Biol. 9, 674–679 (2005).
J. Miyawaki, M. Yudasaka, T. Azami, Y. Kubo, and S. Iijima, “Toxicity of Single-Walled Carbon Nanohorns,” ACS Nano 2, 213–226 (2008).
K. Kostarelos, “The Long and Short of Carbon Nanotube Toxicity,” Nature Biotechnol. 26, 774–776 (2008).
A. Bianco, K. Kostarelos, C. D. Partidos, and M. Prato, “Biomedical Applications of Functionalised Carbon Nanotubes,” Chem. Commun. 41, 571–577 (2005).
X. Shi, S. H. Wang, M. Shen, M. E. Antwerp, X. Chen, C. Li, E. J. Petersen, Q. Huang, W. J. Weber, and J. R. Baker, “Multifunctional Dendrimer-Modified Multiwalled Carbon Nanotubes: Synthesis, Characterization, and in vitro Cancer Cell Targeting and Imaging,” Biomacromol. 10, 1744–1750 (2009).
L. Gu, P. G. Luo, H. Wang, M. J. Meziani, Y. Lin, L. M. Veca, L. Cao, F. Lu, X. Wang, R. A. Quinn, W. Wang, P. Zhang, S. Lacher, and Y. P. Sun, “Single-Walled Carbon Nanotube as a Unique Scaffold for the Multivalent Display of Sugars,” Biomacromol. 9, 2408–2418 (2008).
D. Pantarotto, J. P. Briand, M. Prato, and A. Bianco, “Translocation of Bioactive Peptides across Cell Membranes by Carbon Nanotubes,” Chem. Commun. 40, 16–17 (2004).
I. J. Majoros, A. Myc, T. Thomas, C. B. Mehta, and J. R. Baker, Jr., “PAMAM Dendrimer-Based Multifunctional Conjugate for Cancer Therapy: Synthesis, Characterization, and Functionality,” Biomacromol. 7, 572–579 (2006).
D. S. Novopashina, A. N. Sinyakov, V. A. Ryabinin, A. G. Venyaminova, L. Halby, J.-S. Sun, and A. S. Boutorine, “Sequence-Specific Conjugates of Oligo(2′-O-Methylribonucleotides) and Hairpin Oligocarboxamide Minor-Groove Binders: Design, Synthesis, and Binding Studies with Double-Stranded DNA,” Chem. Biodiv. 2, 936–952 (2005).
D. S. Novopashina, O. S. Totskaya, S. A. Kholodar’, M. I. Meshchaninova, and A. G. Ven’yaminova, “Oligo(2′-O-Methylribonucleotides) and Their Derivatives. III. 5′-Mono- and 5′-Bispyrenyl Conjugates of Oligo(2′-O-Methylribonucleotides) and Their 3′-Modified Analogues: Synthesis and Properties,” Russ. J. Bioorg. Chem. 34, 602 (2008).
V. K. Sarin, S. B. Kent, J. P. Tam, and R. B. Merrifield, “Quantitative Monitoring of Solid-Phase Peptide Synthesis by the Ninhydrin Reaction,” Anal. Biochem. 117, 147–157 (1981).
C. Zhao, Y. Peng, Y. Song, J. Ren, and X. Qu, “Self-Assembly of Single-Stranded RNA on Carbon Nanotube: Polyadenylic Acid to Form a Duplex Structure,” Small 4, 656–661 (2008).
X. Y. Yang, Z. F. Liu, J. Mao, S. J. Wang, Y. F. Ma, and Y. S. Chen, “The Preparation of Functionalized Single Walled Carbon Nanotubes as High Efficiency DNA Carriers,” Chin. Chem. Lett. 18, 1551–1553 (2007).
I. Montesa, E. Munoz, A. M. Benito, W. K. Maser, and M. T. Martinez, “FTIR and Thermogravimetric Analysis of Biotin-Functionalized Single-Walled Carbon Nanotubes,” J. Nanosci. Nanotechnol. 7, 3473–3476 (2007).
A. Jimeno, S. Goyanes, A. Eceiza, G. Kortaberria, I. Mondragon, and M. A. Corcuera, “Effects of Amine Molecular Structure on Carbon Nanotubes Functionalization,” J. Nanosci. Nanotechnol. 9, 6222–6227 (2009).
A. Gromov, S. Dittmer, J. Svensson, O. Nerushev, S. A. Perez-García, L. Licea-Jiménez, R. Rychwalski, and E. E. B. Campbell, “Covalent Amino-Functionalisation of Single-Wall Carbon Nanotubes,” J. Mater. Chem. 15, 3334–3339 (2005).
C. Thomsen and S. Reich, “Raman Scattering in Carbon Nanotubes,” in Light Scattering in Solid IX, Ed. by M. Cardona and R. Merlin (Springer, Berlin, Heidelberg, 2007), pp. 115–234.
R. R. Johnson, A. T. Johnson, and M. L. Klein, “Probing the Structure of DNA-Carbon Nanotube Hybrids with Molecular Dynamics,” Nano Lett. 8, 69–75 (2008).
J. E. Podesta, K. T. Al-Jamal, M. A. Herrero, B. Tian, H. Ali-Boucetta, V. Hegde, A. Bianco, M. Prato, and K. Kostarelos, “Antitumor Activity and Prolonged Survival by Carbon-Nanotube-Mediated Therapeutic SiRNA Silencing in a Human Lung Xenograft Model,” Small 5, 1176–1185 (2009).
Y. Tomonari, H. Murakami, and N. Nakashima, “Solubilization of Single-Walled Carbon Nanotubes by Using Polycyclic Aromatic Ammonium Amphiphiles in Water-Strategy for the Design of High-Performance Solubilizers,” Chem. Eur. J. 12, 4027–4034 (2006).
K. Yang, X. Wang, L. Zhu, and B. Xing, “Competitive Sorption of Pyrene, Phenanthrene, and Naphthalene on Multiwalled Carbon Nanotubes,” Environ. Sci. Technol. 40, 5804–5810 (2006).
S. Zhu, Z. Liu, W. Zhang, S. Han, L. Hu, and G. Xu, “Nucleic Acid Detection Using Single-Walled Carbon Nanohorns as a Fluorescent Sensing Platform,” Chem. Commun. 47, 6099–6101 (2011).
G. E. Pozmogova, A. N. Chuvilin, I. P. Smirnov, M. A. Zaitseva, O. N. Tatarinova, and V. M. Govorun, “Preparation and Properties of Associates of Nickel Nanoparticles with ss-DNA and Proteins,” Nanotechnol. Russ. 3, 391 (2008).
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Original Russian Text © E.K. Apartsin, D.S. Novopashina, Yu.V. Nastaushev, A.G. Ven’yaminova, 2012, published in Rossiiskie Nanotekhnologii, 2012, Vol. 7, Nos. 3–4.
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Apartsin, E.K., Novopashina, D.S., Nastaushev, Y.V. et al. Fluorescently labeled single-walled carbon nanotubes and their hybrids with oligonucleotides. Nanotechnol Russia 7, 99–109 (2012). https://doi.org/10.1134/S1995078012020024
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DOI: https://doi.org/10.1134/S1995078012020024