Nanocrystalline cellulose-fullerene: Novel conjugates

A Herreros-López; M Carini; T Da Ros; T Carofiglio; C Marega; V La Parola; V Rapozzi; L E Xodo; Ali A Alshatwi; C Hadad; M Prato

doi:10.1016/j.carbpol.2017.01.068

Nanocrystalline cellulose-fullerene: Novel conjugates

Carbohydr Polym. 2017 May 15:164:92-101. doi: 10.1016/j.carbpol.2017.01.068. Epub 2017 Jan 23.

Authors

A Herreros-López¹, M Carini², T Da Ros³, T Carofiglio⁴, C Marega⁵, V La Parola⁶, V Rapozzi⁷, L E Xodo⁸, Ali A Alshatwi⁹, C Hadad¹⁰, M Prato¹¹

Affiliations

¹ Centre of Excellence for Nanostructured Materials (CENMAT), INSTM, Department of Chemical and Pharmaceutical Sciences, University of Trieste, P.le Europa 1, 34127, Trieste, Italy. Electronic address: ana.herreroslopez@gmail.com.
² Centre of Excellence for Nanostructured Materials (CENMAT), INSTM, Department of Chemical and Pharmaceutical Sciences, University of Trieste, P.le Europa 1, 34127, Trieste, Italy. Electronic address: marco_carini@yahoo.it.
³ Centre of Excellence for Nanostructured Materials (CENMAT), INSTM, Department of Chemical and Pharmaceutical Sciences, University of Trieste, P.le Europa 1, 34127, Trieste, Italy. Electronic address: daros@units.it.
⁴ Department of Chemical Sciences, University of Padova, Via Marzolo 1, 35131 Padova, Italy. Electronic address: tommaso.carofiglio@unipd.it.
⁵ Department of Chemical Sciences, University of Padova, Via Marzolo 1, 35131 Padova, Italy. Electronic address: carla.marega@unipd.it.
⁶ Institute for the Nanostructured Materials Studies ISMN-CNR, Via La Malfa 153, 90146 Palermo, Italy. Electronic address: laparola@pa.ismn.cnr.it.
⁷ Department of Medical and Biological Sciences,, University of Udine, P.le Kolbe 4, 33100 Udine, Italy. Electronic address: valentina.rapozzi@uniud.it.
⁸ Department of Medical and Biological Sciences,, University of Udine, P.le Kolbe 4, 33100 Udine, Italy. Electronic address: luigi.xodo@uniud.it.
⁹ Department of Food and Nutrition, College of Food and Agriculture Science, King Saud University, P. O. Box 2460 Riyadh 11451, Saudi Arabia. Electronic address: alshatwi@ksu.edu.sa.
¹⁰ Centre of Excellence for Nanostructured Materials (CENMAT), INSTM, Department of Chemical and Pharmaceutical Sciences, University of Trieste, P.le Europa 1, 34127, Trieste, Italy. Electronic address: chadad@units.it.
¹¹ Centre of Excellence for Nanostructured Materials (CENMAT), INSTM, Department of Chemical and Pharmaceutical Sciences, University of Trieste, P.le Europa 1, 34127, Trieste, Italy; CIC BiomaGUNE, Parque Tecnológico de San Sebastián, Paseo Miramón, 182, 20009 San Sebastián, Guipúzcoa, Spain; Basque Foundation for Science, Ikerbasque, Bilbao 48013, Spain. Electronic address: prato@units.it.

PMID: 28325349
DOI: 10.1016/j.carbpol.2017.01.068

Abstract

The covalent grafting of two amino-fullerene C₆₀ derivatives (C₆₀-LC-NH₂ and C₆₀-SC-NH_2, LC=long chain and SC=short chain) onto the surface of TEMPO oxidized nanocrystalline cellulose (NCC-COOH) has been reported for the first time. These hybrids (NCC-LC-C₆₀ and NCC-SC-C₆₀) form stable colloidal suspensions at concentrations up to 0.5mg/mL and act as effective photosensitizers for singlet oxygen production as demonstrated by the oxidation of L-methionine-methyl ester to the corresponding sulphoxide. Using the same approach, in a one-pot reaction both a fluorescent target molecule (FITC-LC-NH₂) and the C₆₀-LC-NH₂ derivative have been successfully attached covalently onto the NCC-COOH surface. These hybrids, which showed no cytotoxicity on MCF-7 human breast cancer cells could be good candidates in photodynamic cancer therapy.

Keywords: Covalent functionalization; Fullerene C(60); Nanocrystalline cellulose; Photooxydation; Water-soluble derivatives.