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Synthesis, pharmacokinetics, and biological use of lysine-modified single-walled carbon nanotubes
We aimed to create a more robust and more accessible standard for amine-modifying single-walled carbon nanotubes (SWCNTs). A 1,3-cycloaddition was developed using an azomethine ylide, generated by reacting paraformaldehyde and a side-chain-Boc (tert-Butyloxycarbonyl)-protected, lysine-derived alpha-...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Dove Medical Press
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4160330/ https://www.ncbi.nlm.nih.gov/pubmed/25228803 http://dx.doi.org/10.2147/IJN.S66050 |
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author | Mulvey, J Justin Feinberg, Evan N Alidori, Simone McDevitt, Michael R Heller, Daniel A Scheinberg, David A |
author_facet | Mulvey, J Justin Feinberg, Evan N Alidori, Simone McDevitt, Michael R Heller, Daniel A Scheinberg, David A |
author_sort | Mulvey, J Justin |
collection | PubMed |
description | We aimed to create a more robust and more accessible standard for amine-modifying single-walled carbon nanotubes (SWCNTs). A 1,3-cycloaddition was developed using an azomethine ylide, generated by reacting paraformaldehyde and a side-chain-Boc (tert-Butyloxycarbonyl)-protected, lysine-derived alpha-amino acid, H-Lys(Boc)-OH, with purified SWCNT or C60. This cycloaddition and its lysine adduct provides the benefits of dense, covalent modification, ease of purification, commercial availability of reagents, and pH-dependent solubility of the product. Subsequently, SWCNTs functionalized with lysine amine handles were covalently conjugated to a radiometalated chelator, 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA). The (111)In-labeled construct showed rapid renal clearance in a murine model and a favorable biodistribution, permitting utility in biomedical applications. Functionalized SWCNTs strongly wrapped small interfering RNA (siRNA). In the first disclosed deployment of thermophoresis with carbon nanotubes, the lysine-modified tubes showed a desirable, weak SWCNT-albumin binding constant. Thus, lysine-modified nanotubes are a favorable candidate for medicinal work. |
format | Online Article Text |
id | pubmed-4160330 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | Dove Medical Press |
record_format | MEDLINE/PubMed |
spelling | pubmed-41603302014-09-16 Synthesis, pharmacokinetics, and biological use of lysine-modified single-walled carbon nanotubes Mulvey, J Justin Feinberg, Evan N Alidori, Simone McDevitt, Michael R Heller, Daniel A Scheinberg, David A Int J Nanomedicine Original Research We aimed to create a more robust and more accessible standard for amine-modifying single-walled carbon nanotubes (SWCNTs). A 1,3-cycloaddition was developed using an azomethine ylide, generated by reacting paraformaldehyde and a side-chain-Boc (tert-Butyloxycarbonyl)-protected, lysine-derived alpha-amino acid, H-Lys(Boc)-OH, with purified SWCNT or C60. This cycloaddition and its lysine adduct provides the benefits of dense, covalent modification, ease of purification, commercial availability of reagents, and pH-dependent solubility of the product. Subsequently, SWCNTs functionalized with lysine amine handles were covalently conjugated to a radiometalated chelator, 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA). The (111)In-labeled construct showed rapid renal clearance in a murine model and a favorable biodistribution, permitting utility in biomedical applications. Functionalized SWCNTs strongly wrapped small interfering RNA (siRNA). In the first disclosed deployment of thermophoresis with carbon nanotubes, the lysine-modified tubes showed a desirable, weak SWCNT-albumin binding constant. Thus, lysine-modified nanotubes are a favorable candidate for medicinal work. Dove Medical Press 2014-09-04 /pmc/articles/PMC4160330/ /pubmed/25228803 http://dx.doi.org/10.2147/IJN.S66050 Text en © 2014 Mulvey et al. This work is published by Dove Medical Press Limited, and licensed under Creative Commons Attribution – Non Commercial (unported, v3.0) License The full terms of the License are available at http://creativecommons.org/licenses/by-nc/3.0/. Non-commercial uses of the work are permitted without any further permission from Dove Medical Press Limited, provided the work is properly attributed. |
spellingShingle | Original Research Mulvey, J Justin Feinberg, Evan N Alidori, Simone McDevitt, Michael R Heller, Daniel A Scheinberg, David A Synthesis, pharmacokinetics, and biological use of lysine-modified single-walled carbon nanotubes |
title | Synthesis, pharmacokinetics, and biological use of lysine-modified single-walled carbon nanotubes |
title_full | Synthesis, pharmacokinetics, and biological use of lysine-modified single-walled carbon nanotubes |
title_fullStr | Synthesis, pharmacokinetics, and biological use of lysine-modified single-walled carbon nanotubes |
title_full_unstemmed | Synthesis, pharmacokinetics, and biological use of lysine-modified single-walled carbon nanotubes |
title_short | Synthesis, pharmacokinetics, and biological use of lysine-modified single-walled carbon nanotubes |
title_sort | synthesis, pharmacokinetics, and biological use of lysine-modified single-walled carbon nanotubes |
topic | Original Research |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4160330/ https://www.ncbi.nlm.nih.gov/pubmed/25228803 http://dx.doi.org/10.2147/IJN.S66050 |
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