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Anionic Fullerenes, Calixarenes, Coronenes, and Pyrenes as Activators of Oligo/Polyarginines in Model Membranes and Live Cells

Authors
Futaki, Shiroh
Lazar, Adina N.
Coleman, Anthony W.
Published in Journal of the American Chemical Society. 2005, vol. 127, no. 4, p. 1114-1115
Abstract We report that the efflux of 5(6)-carboxyfluorescein anions from neutral egg yolk phosphatidylcholine vesicles is mediated by oligo/polyarginines only in the presence of activating amphiphilic anions. Screening of anion activators reveals best synergism for amphiphilic carboxylates (fullerene > calix[4]arene ˜ coronene > pyrene > calix[6]arene > alkyl), whereas amphiphilic sulfates show less satisfactory activation despite often lower effective concentrations. The analogous alcohols and one calix[4]arene diphosphate were inactive. These results are discussed in the context of a tentative anion carrier mechanism, where interactions with bilayer (interface-directed translocation) and carrier (arene-templated carboxylate-guanidinium pairing) contribute to activator efficiencies. Applied to HeLa cells, pyrenebutyrate is shown to significantly increase the uptake of a fluorescently labeled octaarginine in a concentration-dependent manner.
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PERRET, Florent et al. Anionic Fullerenes, Calixarenes, Coronenes, and Pyrenes as Activators of Oligo/Polyarginines in Model Membranes and Live Cells. In: Journal of the American Chemical Society, 2005, vol. 127, n° 4, p. 1114-1115. https://archive-ouverte.unige.ch/unige:6996

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Deposited on : 2010-06-18

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