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 (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.
Original language | English (US) |
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Pages (from-to) | 4245-4255 |
Number of pages | 11 |
Journal | International Journal of Nanomedicine |
Volume | 9 |
DOIs | |
State | Published - 2014 |
Externally published | Yes |
Keywords
- 111In
- DOTA
- azomethine
- cycloaddition
- fullerene
- thermophoresis
ASJC Scopus subject areas
- Biophysics
- Bioengineering
- Biomaterials
- Pharmaceutical Science
- Drug Discovery
- Organic Chemistry