136994-44-0Relevant academic research and scientific papers
Synthesis and antibody binding of highly fluorinated amphiphilic MUC1 glycopeptide antigens
Platen, Tobias,Schueler, Timo,Tremel, Wolfgang,Hoffmann-Roeder, Anja
, p. 3878 - 3887 (2011/09/30)
The analysis of humoral immune responses is of great importance for basic and clinical research. Mapping the structural requirements of epitope recognition with modified tumor-associated carbohydrate antigens allows both the development of biomarkers and the design of synthetic anticancer vaccines. For this purpose, double-tailed hydrocarbon/fluorocarbon membrane anchors have been prepared and conjugated to a TN dipeptide. Furthermore, a novel hydrophobized MUC1 tandem repeat glycopeptide antigen was fully assembled on a solid support and its specific binding to different mouse anti-MUC1 antibodies was demonstrated through ELISA, QCM, and SPR measurements. Such functional fluorous MUC1 antigens are of great interest for specific glycan (micro-)array formats and allow a detailed analyses of serum antibodies obtained from immunization studies. In addition, the intriguing characteristics of fluorous surfactants, for example, their strong self-association tendency, might stimulate the use of novel fluorous-tagged antigen conjugates in the development of multivalent micellar glycopeptide vaccines. Copyright
Synthesis, physical-chemical and biological properties of amphiphilic amino acid conjugates of nitroxides
Durand, Gregory,Choteau, Fanny,Prosak, Robert A.,Rockenbauer, Antal,Villamena, Frederick A.,Pucci, Bernard
, p. 1909 - 1920 (2011/01/06)
Due to the dual property of synthetic nitroxide compounds to either act as probe or antioxidant, efforts toward their selective targeting using specific ligands have been extensively explored. Herein, we report the synthesis of novel amphiphilic nitroxides in which the nitroxyl group is grafted onto an amphiphilic carrier comprising a lactobionamide polar group, a non-polar alkyl chain and an amino acid as scaffold. Piperidine and pyrrolidine nitroxides such as 4-amino-TEMPO (4-AT) and 3-carboxyproxyl (3-CP), respectively, were grafted onto the amphiphilic carriers. To further investigate the effect of the nature of the chain on the physical-chemical and biological properties of nitroxides, hydrogenated or perfluorinated alkyl chains were used. The self-aggregation properties in aqueous media of these surfactant-like nitroxides were confirmed by dynamic light scattering (DLS) as well as electron paramagnetic resonance (EPR) spectroscopy, and were correlated with their respective lipophilicity. The effect of the carrier groups on the electrochemical property of nitroxides was investigated using cyclic voltammetry, and the rates of reduction using ascorbate as reducing agent were measured. Finally, their cytoprotective property against toxic concentrations of hydrogen peroxide using bovine aortic endothelial cells was also investigated.
