Membrane-active calixarenes: toward 'gating' transmembrane anion transport

Oluyomi A. Okunola, Jennifer L. Seganish, Kevan J. Salimian, Peter Y. Zavalij, Jeffery T. Davis

Research output: Contribution to journalArticlepeer-review

Abstract

This paper describes on-going efforts to develop calixarene amides as transmembrane anion transporters. We report on the transport of Cl- anions across phospholipid membranes as mediated by some lipophilic calixarenes, all fixed in the cone conformation. We present significant findings regarding use of these calixarenes as transmembrane Cl- transporters: (1) the cone conformer cone-H 2a, like its 1,3-alt and paco isomers, transports Cl- across liposomal membranes; (2) the conformation of the calixarene (paco-H 1 vs cone-H 2a) is important for modulating Cl- transport rates; (3) the substitution pattern on the calixarene's upper rim is crucial for Cl- transport function; and (4) at least one of the four arms of the calixarene can be left unmodified without loss of function, enabling development of a pH-sensitive anion transporter (TAC-OH 3). This last finding is useful given the interest in gating the activity of synthetic ion transporters with external stimuli.

Original languageEnglish (US)
Pages (from-to)10743-10750
Number of pages8
JournalTetrahedron
Volume63
Issue number44
DOIs
StatePublished - Oct 29 2007
Externally publishedYes

Keywords

  • Anion transport
  • Calix[4]arene
  • Transmembrane

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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