title: Fullerene as a transporter for doxorubicin investigated by analytical methods and in vivo imaging.
abstract: Carbon nanomaterials, including fullerenes, exhibit not only unique structure and electronic properties but also a significant potential to serve as radical scavengers and/or anti-oxidants. Their conjugation with anticancer drugs such as doxorubicin (DOX) may help to balance severe negative side effects of these cytostatics and also improve the delivery of the drug taking advantage of the enhanced cellular uptake, selectivity to cancer cells, and pH regulated release. In this study, the fullerene (C60) surface was oxidized by concentrated nitric acid, which enabled simple DOX-fullerene conjugation based on π-π stacking and hydrophilic interactions with carboxylic groups. The strength of this noncovalent binding is pH dependent. At a low pH, the amino group of DOX is protonated, however at a higher pH, the amino group is deprotonated, resulting in stronger hydrophobic interactions with the fullerene walls. CE and HPLC were employed for characterization of resulting complexes. The cell toxicity of the conjugates was evaluated using Staphylococcus aureus and finally they were administered into the chicken embryo to assess the applicability for in vivo imaging.
authors.affiliation: Faculty of Agronomy, Department of Chemistry and Biochemistry, Mendel University in Brno, Brno, Czech Republic.
authors.forename: Iva
authors.initials: I
authors.lastname: Blazkova
authors.forename: Hoai
authors.initials: H
authors.lastname: Viet Nguyen
authors.forename: Marketa
authors.initials: M
authors.lastname: Kominkova
authors.forename: Romana
authors.initials: R
authors.lastname: Konecna
authors.forename: Dagmar
authors.initials: D
authors.lastname: Chudobova
authors.forename: Ludmila
authors.initials: L
authors.lastname: Krejcova
authors.forename: Pavel
authors.initials: P
authors.lastname: Kopel
authors.forename: David
authors.initials: D
authors.lastname: Hynek
authors.forename: Ondrej
authors.initials: O
authors.lastname: Zitka
authors.forename: Miroslava
authors.initials: M
authors.lastname: Beklova
authors.forename: Vojtech
authors.initials: V
authors.lastname: Adam
authors.forename: Rene
authors.initials: R
authors.lastname: Kizek
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000493:pharmacokinetics* / Q000494:pharmacology; D002642:Chick Embryo; D004317:Doxorubicin / Q000737:chemistry / Q000493:pharmacokinetics* / Q000494:pharmacology; D004337:Drug Carriers / Q000737:chemistry / Q000493:pharmacokinetics*; D037741:Fullerenes / Q000737:chemistry / Q000493:pharmacokinetics*; D057927:Hydrophobic and Hydrophilic Interactions; D013050:Spectrometry, Fluorescence; D013211:Staphylococcus aureus / Q000187:drug effects; D014018:Tissue Distribution
chemical_list: D000900:Anti-Bacterial Agents; D004337:Drug Carriers; D037741:Fullerenes; D004317:Doxorubicin
keywords: Clinical analysis; Doxorubicin; Drug delivery; Embryo; Fullerene; Nanomedicine