PMID- 22563986 OWN - NLM STAT- MEDLINE DCOM- 20120921 LR - 20120529 IS - 1520-5827 (Electronic) IS - 0743-7463 (Linking) VI - 28 IP - 21 DP - 2012 May 29 TI - Effects of amphiphile topology on the aggregation of oligocholates in lipid membranes: macrocyclic versus linear amphiphiles. PG - 8165-73 LID - 10.1021/la301090t [doi] AB - A macrocyclic and a linear trimer of a facially amphiphilic cholate building block were labeled with a fluorescent dansyl group. The environmentally sensitive fluorophore enabled the aggregation of the two oligocholates in lipid membranes to be studied by fluorescence spectroscopy. Concentration-dependent emission wavelength and intensity revealed a higher concentration of water for the cyclic compound. Both compounds were shown by the red-edge excitation shift (REES) to be located near the membrane/water interface at low concentrations, but the cyclic trimer was better able to migrate into the hydrophobic core of the membrane than the linear trimer. Fluorescent quenching by a water-soluble (NaI) and a lipid-soluble (TEMPO) quencher indicated that the cyclic trimer penetrated into the hydrophobic region of the membrane more readily than the linear trimer, which preferred to stay close to the membrane surface. The fluorescent data corroborated with the previous leakage assays that suggested the stacking of the macrocyclic cholate trimer into transmembrane nanopores, driven by the strong associative interactions of water molecules inside the macrocycles in a nonpolar environment. FAU - Widanapathirana, Lakmini AU - Widanapathirana L AD - Department of Chemistry, Iowa State University, Ames, Iowa 50011-3111, United States. FAU - Zhao, Yan AU - Zhao Y LA - eng PT - Journal Article PT - Research Support, U.S. Gov't, Non-P.H.S. DEP - 20120514 PL - United States TA - Langmuir JT - Langmuir : the ACS journal of surfaces and colloids JID - 9882736 RN - 0 (Cholates) RN - 0 (Lipid Bilayers) RN - 0 (Macrocyclic Compounds) RN - 0 (Surface-Active Agents) SB - IM MH - Cholates/chemical synthesis/*chemistry MH - Fluorescence MH - Lipid Bilayers/chemical synthesis/*chemistry MH - Macrocyclic Compounds/chemical synthesis/*chemistry MH - Models, Molecular MH - Spectrometry, Fluorescence MH - Surface-Active Agents/chemical synthesis/*chemistry EDAT- 2012/05/09 06:00 MHDA- 2012/09/22 06:00 CRDT- 2012/05/09 06:00 PHST- 2012/05/09 06:00 [entrez] PHST- 2012/05/09 06:00 [pubmed] PHST- 2012/09/22 06:00 [medline] AID - 10.1021/la301090t [doi] PST - ppublish SO - Langmuir. 2012 May 29;28(21):8165-73. doi: 10.1021/la301090t. Epub 2012 May 14.