Synthesis, pharmacokinetics, and biological use of lysine-modified single-walled carbon nanotubes Journal Article

   


Authors: Mulvey, J. J.; Feinberg, E.; Alidori, S.; McDevitt, M. R.; Heller, D. A.; Scheinberg, D. A.
Article Title: Synthesis, pharmacokinetics, and biological use of lysine-modified single-walled carbon nanotubes
Abstract: 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 In-111-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.
Keywords: mice; chemistry; functionalization; cycloaddition; biodistribution; delivery; dispersion; dota; in-111; fullerene; azomethine ylides; azomethine; graphene; thermophoresis
Journal Title: International Journal of Nanomedicine
Volume: 9
ISSN: 1178-2013
Publisher: Dove Medical Press Ltd  
Date Published: 2014-09-04
Start Page: 4245
End Page: 4255
Language: English
ACCESSION: WOS:000341196700001
DOI: 10.2147/ijn.s66050
PROVIDER: wos
PMCID: PMC4160330
PUBMED: 25228803
Notes: Article -- Source: Wos
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MSK Authors
  1. Michael R Mcdevitt
    144 Mcdevitt
  2. David Scheinberg
    499 Scheinberg
  3. Simone Alidori
    11 Alidori
  4. Daniel Alan Heller
    112 Heller
  5. Evan Feinberg
    5 Feinberg
  6. Joseph Justin Mulvey
    14 Mulvey
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