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 journalArticle

109 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 languageEnglish
Pages (from-to)1114-1115
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number4
DOIs
Publication statusPublished - Feb 2 2005
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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