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1.
Chemistry ; 17(51): 14663-71, 2011 Dec 16.
Article in English | MEDLINE | ID: mdl-22095560

ABSTRACT

The dispersion of highly hydrophobic carbon materials such as carbon nanotubes in biological media is a challenging issue. Indeed, the nonspecific adsorption of proteins occurs readily when the nanotubes are introduced in biological media; therefore, a methodology to control adsorption is in high demand. To address this issue, we developed a bifunctional linker derived from pyrene that selectively enables or prevents the adsorption of proteins on single-wall carbon nanotubes (SWNTs). We demonstrated that it is possible to decrease or completely suppress the adsorption of proteins on the nanotube sidewall by using proper functionalization (either covalent or noncovalent). By subsequently activating the functional groups on the nanotube derivatives, protein adsorption can be recovered and, therefore, controlled. Our approach is simple, straightforward, and potentially suitable for other biomolecules that contain thio or amino groups available for coupling.


Subject(s)
Nanotubes, Carbon/chemistry , Proteins/chemistry , Pyrenes/chemistry , Serum Albumin, Bovine/chemistry , Surface-Active Agents/chemistry , Adsorption , Molecular Structure , Pyrrolidinones/chemistry
2.
Chemphyschem ; 12(1): 150-60, 2011 Jan 17.
Article in English | MEDLINE | ID: mdl-21226196

ABSTRACT

We have synthesised a new, pyrene-based, low-molecular-mass, amphiphilic molecule that displays a wealth of properties of potential interest for aggregation and interfacial applications. In order to elucidate some of the key properties of this molecule, which consists of a pyrene-containing hydrophobic head and a short PEG-based hydrophilic tail, we investigate herein some aspects of its concentration-dependent behaviour in aqueous solutions. We show that the inclusion of the hydrophobic pyrene group not only provides the molecule with intriguing bulk and interfacial properties down to low concentrations, but also with various means of assessing its aggregation behaviour by means of its well-characterised fluorescence properties. Combining a range of fluorescence techniques with microscopic imaging (optical and Cryo-TEM), interfacial tension measurements and foaming studies, we have been able to identify and characterise three concentration-dependant regimes. At low concentrations, the molecule is dissolved in monomeric form. At intermediate concentrations, labile aggregates are formed, which, at higher concentrations, give way to aggregates containing pre-associated pyrenes. Our measurements strongly imply that the latter aggregates are hexagonally close-packed tubular micelles. In this latter regime we also find a range of micron-sized precipitates. Additionally, the molecule displays strong interfacial activity, yet a surprisingly slow dynamics of interfacial adsorption. Finally, we demonstrate the possibility of using it to visualize interfaces and also create reasonably stable (1 hour) and fluorescing foams.


Subject(s)
Fluorescence , Fluorescent Dyes/chemistry , Pyrenes/chemistry , Fluorescent Dyes/chemical synthesis , Molecular Structure , Molecular Weight , Particle Size , Polyethylene Glycols/chemistry , Spectrometry, Fluorescence , Surface Properties
3.
Sci Rep ; 3: 1124, 2013.
Article in English | MEDLINE | ID: mdl-23350031

ABSTRACT

Single-walled carbon nanotubes (SWCNTs) have been widely explored as potential technologies for information systems and medical applications. The impact of SWCNTs on human health is of prime concern, if SWCNTs have a future in the manufacturing industry. This study proposes a novel, inflammation-independent paradigm of toxicity for SWCNTs, identifying the protein citrullination process as early-stage indicator of inflammatory responses of macrophages (THP-1) and of subtle phenotypic damages of lung epithelial (A549) cells following exposure to chemically-treated SWCNTs. Our results showed that, while most of the cellular responses of A549 cells exposed to SWCNTs are different to those of similarly treated THP-1 cells, the protein citrullination process is triggered in a dose- and time-dependent manner in both cell lines, with thresholds comparable between inflammatory (THP-1) and non-inflammatory (A549) cell types. The cellular mechanism proposed herein could have a high impact in predicting the current risk associated with environmental exposure to SWCNTs.


Subject(s)
Cell Membrane Permeability/drug effects , Citrulline/metabolism , Nanotubes, Carbon/toxicity , Cell Line , Cell Survival/drug effects , Cytokines/metabolism , Humans , Macrophages/drug effects , Macrophages/metabolism , Nanotubes, Carbon/chemistry
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