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 language | English (US) |
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Pages (from-to) | 10743-10750 |
Number of pages | 8 |
Journal | Tetrahedron |
Volume | 63 |
Issue number | 44 |
DOIs | |
State | Published - Oct 29 2007 |
Externally published | Yes |
Keywords
- Anion transport
- Calix[4]arene
- Transmembrane
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry