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Molecular recognition by macrocyclic receptors having multiple hydrophobic branches in a synthetic bilayer membrane
Author(s) -
Kikuchi JunIchi,
Matsushima Chiemi,
Tanaka Yumi,
Hie KenIchi,
Suehiro Kazuaki,
Hayashida Osamu,
Murakami Yukito
Publication year - 1992
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610051004
Subject(s) - chemistry , bilayer , cationic polymerization , lipid bilayer , cyclophane , hydrophobic effect , membrane , lipid bilayer phase behavior , stereochemistry , calixarene , crystallography , polymer chemistry , organic chemistry , molecule , biochemistry
Abstract Hybrid molecular assemblies were prepared in combinations of a synthetic peptide lipid, involving an L‐alanine residue interposed between an anionic head group and a hydrophobic double‐chain segment, with cationic macrocyclic hosts, a steroid cyclophane bearing four rigid steroid moieties and octopus cyclophanes having eight flexible hydrocarbon branches. On addition of the cyclophanes to multi‐walled bilayer membranes composed of the anionic lipid, thermodynamic parameters (Δ H and Δ S ) associated with the phase transition between the gel and liquidcrystalline states were subjected to changes that are consistent with the formation of the hybrid assemblies. Anionic fluorescent guests, 8‐anilinonaphthalene‐1‐sulphonate and 6‐ p ‐toluidinonaphthalene‐2‐sulphonate, were effectively incorporated into the hydrophobic cavities provided by the cationic cyclophanes embedded in the bilayer membrane through hydrophobic and electrostatic interactions. The guest‐binding modes of the hybrid assemblies are classified into two types; a guest is included in the proximity of the hydrogen‐belt domain of the bilayer membrane in one mode, and a guest is incorporated into the hydrophobic bilayer domain composed of double hydrocarbon chains of the lipid in another.