Anionic fullerenes, calixarenes, coronenes, and pyrenes as activators of oligo/polyarginines in model membranes and live cells

Florent Perret; Masamichi Nishihara; Toshihide Takeuchi; Shiroh Futaki; Adina N. Lazar; Anthony W. Coleman; Naomi Sakai; Stefan Matile

doi:10.1021/ja043633c

Anionic fullerenes, calixarenes, coronenes, and pyrenes as activators of oligo/polyarginines in model membranes and live cells

Florent Perret, Masamichi Nishihara, Toshihide Takeuchi, Shiroh Futaki, Adina N. Lazar, Anthony W. Coleman, Naomi Sakai, Stefan Matile

Research output: Contribution to journal › Article › peer-review

117 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1114-1115
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	127
Issue number	4
DOIs	https://doi.org/10.1021/ja043633c
Publication status	Published - Feb 2 2005
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Anionic fullerenes, calixarenes, coronenes, and pyrenes as activators of oligo/polyarginines in model membranes and live cells",

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.",

author = "Florent Perret and Masamichi Nishihara and Toshihide Takeuchi and Shiroh Futaki and Lazar, {Adina N.} and Coleman, {Anthony W.} and Naomi Sakai and Stefan Matile",

year = "2005",

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doi = "10.1021/ja043633c",

language = "English",

volume = "127",

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journal = "Journal of the American Chemical Society",

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AU - Perret, Florent

AU - Nishihara, Masamichi

AU - Takeuchi, Toshihide

AU - Futaki, Shiroh

AU - Lazar, Adina N.

AU - Coleman, Anthony W.

AU - Sakai, Naomi

AU - Matile, Stefan

PY - 2005/2/2

Y1 - 2005/2/2

N2 - 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.

AB - 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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Anionic fullerenes, calixarenes, coronenes, and pyrenes as activators of oligo/polyarginines in model membranes and live cells

Abstract

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