p-octiphenyl beta-barrels with ion channel and esterase activity.
Design, synthesis, and esterase and ion channel activity of a novel barrel-stave supramolecule with hydrophobic exterior and histidine-rich interior are reported. Voltage-dependent binding of pyrenyl-8-oxy-1,3,6-trisulfonates by histidines within p-octiphenyl beta-barrels (and not monomers) via ionic (and not hydrophobic) interactions (K(D), K(I), K(M) < 1 microM) is the basis for superb esterolytic proficiency up to (k(cat)/K(M))/k(uncat) = 9.6 x 10(5) in water and bilayer membranes. The conductance of labile ion channels formed in planar bilayer membranes is shown to be reduced by 8-hydroxypyrene-1,3,6-trisulfonate on the single- and multichannel level. [reaction: see text]
Baumeister
B
B
Department of Organic Chemistry, University of Geneva, CH-1211 Geneva, Switzerland.
Sakai
N
N
Matile
S
S
D004950:Esterases / Q000187:drug effects* / Q000378:metabolism; D006868:Hydrolysis; D007473:Ion Channels / Q000187:drug effects* / Q000502:physiology; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D007473:Ion Channels; D010636:Phenols; C080417:4-octylphenol; D004950:Esterases