Unmasking tandem site interaction in human acetylcholinesterase. Substrate activation with a cationic acetanilide substrate

Biochemistry. 2003 May 13;42(18):5438-52. doi: 10.1021/bi027065u.

Abstract

Acetylcholinesterase (AChE) contains a narrow and deep active site gorge with two sites of ligand binding, an acylation site (or A-site) at the base of the gorge, and a peripheral site (or P-site) near the gorge entrance. The P-site contributes to catalytic efficiency by transiently binding substrates on their way to the acylation site, where a short-lived acyl enzyme intermediate is produced. A conformational interaction between the A- and P-sites has recently been found to modulate ligand affinities. We now demonstrate that this interaction is of functional importance by showing that the acetylation rate constant of a substrate bound to the A-site is increased by a factor a when a second molecule of substrate binds to the P-site. This demonstration became feasible through the introduction of a new acetanilide substrate analogue of acetylcholine, 3-(acetamido)-N,N,N-trimethylanilinium (ATMA), for which a = 4. This substrate has a low acetylation rate constant and equilibrates with the catalytic site, allowing a tractable algebraic solution to the rate equation for substrate hydrolysis. ATMA affinities for the A- and P-sites deduced from the kinetic analysis were confirmed by fluorescence titration with thioflavin T as a reporter ligand. Values of a >1 give rise to a hydrolysis profile called substrate activation, and the AChE site-specific mutant W86F, and to a lesser extent wild-type human AChE itself, showed substrate activation with acetylthiocholine as the substrate. Substrate activation was incorporated into a previous catalytic scheme for AChE in which a bound P-site ligand can also block product dissociation from the A-site, and two additional features of the AChE catalytic pathway were revealed. First, the ability of a bound P-site ligand to increase the substrate acetylation rate constant varied with the structure of the ligand: thioflavin T accelerated ATMA acetylation by a factor a(2) of 1.3, while propidium failed to accelerate. Second, catalytic rate constants in the initial intermediate formed during acylation (EAP, where EA is the acyl enzyme and P is the alcohol leaving group cleaved from the ester substrate) may be constrained such that the leaving group P must dissociate before hydrolytic deacylation can occur.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acetanilides / metabolism*
  • Acetophenones / chemistry
  • Acetophenones / metabolism
  • Acetophenones / pharmacology
  • Acetylcholinesterase / chemistry*
  • Acetylcholinesterase / genetics
  • Acetylcholinesterase / metabolism*
  • Acetylthiocholine / metabolism*
  • Acylation
  • Benzothiazoles
  • Binding Sites
  • Catalysis
  • Cholinesterase Inhibitors / metabolism
  • Drug Interactions
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / metabolism
  • Fluorescent Dyes / pharmacology
  • Humans
  • Hydrolysis
  • Ligands
  • Models, Chemical
  • Mutagenesis, Site-Directed
  • Propidium / chemistry
  • Protein Conformation
  • Recombinant Proteins / genetics
  • Recombinant Proteins / isolation & purification
  • Recombinant Proteins / metabolism
  • Stereoisomerism
  • Substrate Specificity / drug effects
  • Thiazoles / chemistry
  • Thiazoles / metabolism
  • Thiazoles / pharmacology

Substances

  • Acetanilides
  • Acetophenones
  • Benzothiazoles
  • Cholinesterase Inhibitors
  • Fluorescent Dyes
  • Ligands
  • Recombinant Proteins
  • Thiazoles
  • m-(N,N,N-trimethylammonio)trifluoroacetophenone
  • thioflavin T
  • Propidium
  • Acetylthiocholine
  • Acetylcholinesterase