Hyaluronan-carbon nanotube derivatives: Synthesis, conjugation with model drugs, and DOSY NMR characterization

Riccardo Marega, M. Bergamin, V. Aroulmoji, F. Dinon, M. Prato, E. Murano

Research output: Contribution to journalArticle

Abstract

Carbon nanotube (CNTs) derivatives are nowadays under thorough investigation as biomedically interesting materials. In this paper we describe a method for the preparation of water-soluble CNTs by condensation of the carboxylic groups introduced onto the carbon framework and the primary amine moieties inserted in the naturally occurring biopolymer hyaluronan (HA). The covalent conjugation between CNTs and HA should merge the biocompatibility and further processability of the HA chains with the well-known cellular penetration properties of the CNT derivatives to produce novel drug delivery platforms. In fact, thanks to the primary amino groups introduced in the HA chains, HA-CNT derivatives can be further covalently modified with model drugs like ibuprofen and methotrexate. We describe also the monitoring of all the CNT derivatization steps by diffusion-ordered NMR spectroscopy (DOSY), a technique that allows fast and reliable characterization of these novel derivatives.
Original languageEnglish
Pages (from-to)5617-5625
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number28
DOIs
Publication statusPublished - 1 Oct 2011

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Carbon Nanotubes
Hyaluronic Acid
conjugation
Nuclear magnetic resonance spectroscopy
drugs
carbon nanotubes
Nuclear magnetic resonance
Derivatives
nuclear magnetic resonance
synthesis
Pharmaceutical Preparations
spectroscopy
Biopolymers
Ibuprofen
biopolymers
biocompatibility
Drug delivery
Biocompatibility
Methotrexate
Amines

Cite this

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abstract = "Carbon nanotube (CNTs) derivatives are nowadays under thorough investigation as biomedically interesting materials. In this paper we describe a method for the preparation of water-soluble CNTs by condensation of the carboxylic groups introduced onto the carbon framework and the primary amine moieties inserted in the naturally occurring biopolymer hyaluronan (HA). The covalent conjugation between CNTs and HA should merge the biocompatibility and further processability of the HA chains with the well-known cellular penetration properties of the CNT derivatives to produce novel drug delivery platforms. In fact, thanks to the primary amino groups introduced in the HA chains, HA-CNT derivatives can be further covalently modified with model drugs like ibuprofen and methotrexate. We describe also the monitoring of all the CNT derivatization steps by diffusion-ordered NMR spectroscopy (DOSY), a technique that allows fast and reliable characterization of these novel derivatives.",
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Hyaluronan-carbon nanotube derivatives: Synthesis, conjugation with model drugs, and DOSY NMR characterization. / Marega, Riccardo; Bergamin, M.; Aroulmoji, V.; Dinon, F.; Prato, M.; Murano, E.

In: European Journal of Organic Chemistry, No. 28, 01.10.2011, p. 5617-5625.

Research output: Contribution to journalArticle

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AU - Marega, Riccardo

AU - Bergamin, M.

AU - Aroulmoji, V.

AU - Dinon, F.

AU - Prato, M.

AU - Murano, E.

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