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PDBsum entry 1j07
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Contents |
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* Residue conservation analysis
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Enzyme class:
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E.C.3.1.1.7
- acetylcholinesterase.
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Reaction:
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acetylcholine + H2O = choline + acetate + H+
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acetylcholine
Bound ligand (Het Group name = )
matches with 41.18% similarity
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+
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H2O
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=
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choline
Bound ligand (Het Group name = )
matches with 60.00% similarity
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+
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acetate
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+
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H(+)
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Molecule diagrams generated from .mol files obtained from the
KEGG ftp site
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DOI no:
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EMBO J
22:1
(2003)
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PubMed id:
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Structural insights into ligand interactions at the acetylcholinesterase peripheral anionic site.
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Y.Bourne,
P.Taylor,
Z.Radić,
P.Marchot.
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ABSTRACT
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The peripheral anionic site on acetylcholinesterase (AChE), located at the
active center gorge entry, encompasses overlapping binding sites for allosteric
activators and inhibitors; yet, the molecular mechanisms coupling this site to
the active center at the gorge base to modulate catalysis remain unclear. The
peripheral site has also been proposed to be involved in heterologous protein
associations occurring during synaptogenesis or upon neurodegeneration. A novel
crystal form of mouse AChE, combined with spectrophotometric analyses of the
crystals, enabled us to solve unique structures of AChE with a free peripheral
site, and as three complexes with peripheral site inhibitors: the
phenylphenanthridinium ligands, decidium and propidium, and the pyrogallol
ligand, gallamine, at 2.20-2.35 A resolution. Comparison with structures of AChE
complexes with the peptide fasciculin or with organic bifunctional inhibitors
unveils new structural determinants contributing to ligand interactions at the
peripheral site, and permits a detailed topographic delineation of this site.
Hence, these structures provide templates for designing compounds directed to
the enzyme surface that modulate specific surface interactions controlling
catalytic activity and non-catalytic heterologous protein associations.
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Selected figure(s)
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Figure 1.
Figure 1 PAS ligands (AChE inhibitors) used in this study.
Schematic drawings (from top to bottom) of the
phenylphenanthridinium ligands propidium (PI;
3,8-diamino-5[3'-(diethylmethylammonio) propyl]-6-phenyl
phenanthridinium) and decidium (DI; 3,8-diamino-5[10'-
(trimethyl-ammonio) decyl]-6-phenyl phenanthridinium), and of
the pyrogallol ligand gallamine (GAL;
2,2',2"-[1,2,3-benzene-triyltris(oxy)]tris[N,N,N-triethylethanamonium]).
PI and DI were diiodide salts and GAL was a triiodide.
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Figure 5.
Figure 5 Structural comparisons of the DI -mAChE complex with
the Fas2 -mAChE complex and the crystalline mAChE tetramer. (A)
Close-up view of a superimposition of the DI molecule (orange
bonds, blue nitrogen and red oxygen atoms) in the DI -mAChE
complex with the interacting central loop (loop II) of Fas2
(yellow) bound to mAChE in the Fas2 -mAChE complex (1KU6),
according to all C[  ]atoms
of mAChE in the two structures. The Fas2 side chains that match
the structural determinants of the DI molecule are displayed as
green bonds. (B) Superimposition of the DI molecule (colored as
in A) in the DI -mAChE complex with the PAS-occluding short  loop
(yellow) of subunit A in the mAChE tetrameric assembly (1MAA),
according to all C[ ]atoms
of mAChE in the DI -mAChE complex and in the tetramer subunit C.
Those of the mAChE short loop
side chains that match the structural determinants of the DI
molecule are displayed as orange bonds. The mAChE molecular
surfaces buried at the Fas2 -mAChE complex interface (A) and at
the loop
-PAS interface (B) are shown in transparency.
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The above figures are
reprinted
from an Open Access publication published by Macmillan Publishers Ltd:
EMBO J
(2003,
22,
1-0)
copyright 2003.
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Figures were
selected
by an automated process.
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Literature references that cite this PDB file's key reference
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PubMed id
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Reference
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F.Belluti,
M.Bartolini,
G.Bottegoni,
A.Bisi,
A.Cavalli,
V.Andrisano,
and
A.Rampa
(2011).
Benzophenone-based derivatives: a novel series of potent and selective dual inhibitors of acetylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation.
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Eur J Med Chem,
46,
1682-1693.
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M.Amitay,
and
A.Shurki
(2011).
Hydrolysis of organophosphate compounds by mutant butyrylcholinesterase: a story of two histidines.
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Proteins,
79,
352-364.
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M.K.Kesharwani,
B.Ganguly,
A.Das,
and
T.Bandyopadhyay
(2010).
Differential binding of bispyridinium oxime drugs with acetylcholinesterase.
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Acta Pharmacol Sin,
31,
313-328.
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M.S.García-Ayllón,
I.Riba-Llena,
C.Serra-Basante,
J.Alom,
R.Boopathy,
and
J.Sáez-Valero
(2010).
Altered levels of acetylcholinesterase in Alzheimer plasma.
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PLoS One,
5,
e8701.
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S.Bremm,
T.Schreck,
P.Boba,
S.Held,
and
K.Hamacher
(2010).
Computing and visually analyzing mutual information in molecular co-evolution.
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BMC Bioinformatics,
11,
330.
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S.H.Kim,
M.Spensley,
S.K.Choi,
C.P.Calixto,
A.F.Pendle,
O.Koroleva,
P.J.Shaw,
and
J.W.Brown
(2010).
Plant U13 orthologues and orphan snoRNAs identified by RNomics of RNA from Arabidopsis nucleoli.
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Nucleic Acids Res,
38,
3054-3067.
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E.Meggers
(2009).
Targeting proteins with metal complexes.
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Chem Commun (Camb),
(),
1001-1010.
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F.Ekström,
A.Hörnberg,
E.Artursson,
L.G.Hammarström,
G.Schneider,
and
Y.P.Pang
(2009).
Structure of HI-6*sarin-acetylcholinesterase determined by X-ray crystallography and molecular dynamics simulation: reactivator mechanism and design.
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PLoS One,
4,
e5957.
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PDB codes:
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J.Shenouda,
P.Green,
and
L.Sultatos
(2009).
An evaluation of the inhibition of human butyrylcholinesterase and acetylcholinesterase by the organophosphate chlorpyrifos oxon.
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Toxicol Appl Pharmacol,
241,
135-142.
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K.T.Tycowski,
M.D.Shu,
A.Kukoyi,
and
J.A.Steitz
(2009).
A conserved WD40 protein binds the Cajal body localization signal of scaRNP particles.
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Mol Cell,
34,
47-57.
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M.Amitay,
and
A.Shurki
(2009).
The structure of G117H mutant of butyrylcholinesterase: nerve agents scavenger.
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Proteins,
77,
370-377.
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M.F.Montenegro,
M.T.Moral-Naranjo,
E.Muñoz-Delgado,
F.J.Campoy,
and
C.J.Vidal
(2009).
Hydrolysis of acetylthiocoline, o-nitroacetanilide and o-nitrotrifluoroacetanilide by fetal bovine serum acetylcholinesterase.
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FEBS J,
276,
2074-2083.
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M.Pietsch,
L.Christian,
T.Inhester,
S.Petzold,
and
M.Gütschow
(2009).
Kinetics of inhibition of acetylcholinesterase in the presence of acetonitrile.
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FEBS J,
276,
2292-2307.
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R.Pattanayek,
T.Mori,
Y.Xu,
S.Pattanayek,
C.H.Johnson,
and
M.Egli
(2009).
Structures of KaiC circadian clock mutant proteins: a new phosphorylation site at T426 and mechanisms of kinase, ATPase and phosphatase.
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PLoS One,
4,
e7529.
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PDB codes:
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T.A.Slotkin,
I.T.Ryde,
N.Wrench,
J.A.Card,
and
F.J.Seidler
(2009).
Nonenzymatic role of acetylcholinesterase in neuritic sprouting: regional changes in acetylcholinesterase and choline acetyltransferase after neonatal 6-hydroxydopamine lesions.
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Neurotoxicol Teratol,
31,
183-186.
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T.Hansmann,
B.Sanson,
J.Stojan,
M.Weik,
J.L.Marty,
and
D.Fournier
(2009).
Kinetic insight into the mechanism of cholinesterasterase inhibition by aflatoxin B1 to develop biosensors.
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Biosens Bioelectron,
24,
2119-2124.
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Y.P.Pang,
F.Ekström,
G.A.Polsinelli,
Y.Gao,
S.Rana,
D.H.Hua,
B.Andersson,
P.O.Andersson,
L.Peng,
S.K.Singh,
R.K.Mishra,
K.Y.Zhu,
A.M.Fallon,
D.W.Ragsdale,
and
S.Brimijoin
(2009).
Selective and irreversible inhibitors of mosquito acetylcholinesterases for controlling malaria and other mosquito-borne diseases.
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PLoS One,
4,
e6851.
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PDB code:
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C.Teller,
J.Halámek,
J.Zeravík,
W.F.Stöcklein,
and
F.W.Scheller
(2008).
Development of a bifunctional sensor using haptenized acetylcholinesterase and application for the detection of cocaine and organophosphates.
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Biosens Bioelectron,
24,
111-117.
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C.Vardabasso,
L.Manganaro,
M.Lusic,
A.Marcello,
and
M.Giacca
(2008).
The histone chaperone protein Nucleosome Assembly Protein-1 (hNAP-1) binds HIV-1 Tat and promotes viral transcription.
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Retrovirology,
5,
8.
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M.X.Silveyra,
G.Evin,
M.F.Montenegro,
C.J.Vidal,
S.Martínez,
J.G.Culvenor,
and
J.Sáez-Valero
(2008).
Presenilin 1 interacts with acetylcholinesterase and alters its enzymatic activity and glycosylation.
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Mol Cell Biol,
28,
2908-2919.
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R.Pattanayek,
D.R.Williams,
S.Pattanayek,
T.Mori,
C.H.Johnson,
P.L.Stewart,
and
M.Egli
(2008).
Structural model of the circadian clock KaiB-KaiC complex and mechanism for modulation of KaiC phosphorylation.
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EMBO J,
27,
1767-1778.
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PDB code:
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S.K.Cha,
B.Ortega,
H.Kurosu,
K.P.Rosenblatt,
M.Kuro-O,
and
C.L.Huang
(2008).
Removal of sialic acid involving Klotho causes cell-surface retention of TRPV5 channel via binding to galectin-1.
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Proc Natl Acad Sci U S A,
105,
9805-9810.
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Y.Yao,
C.B.Harrison,
P.L.Freddolino,
K.Schulten,
and
M.L.Mayer
(2008).
Molecular mechanism of ligand recognition by NR3 subtype glutamate receptors.
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EMBO J,
27,
2158-2170.
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PDB codes:
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D.Araç,
A.A.Boucard,
E.Ozkan,
P.Strop,
E.Newell,
T.C.Südhof,
and
A.T.Brunger
(2007).
Structures of neuroligin-1 and the neuroligin-1/neurexin-1 beta complex reveal specific protein-protein and protein-Ca2+ interactions.
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Neuron,
56,
992.
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PDB codes:
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F.J.Ekström,
C.Astot,
and
Y.P.Pang
(2007).
Novel nerve-agent antidote design based on crystallographic and mass spectrometric analyses of tabun-conjugated acetylcholinesterase in complex with antidotes.
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Clin Pharmacol Ther,
82,
282-293.
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PDB codes:
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G.J.Towers
(2007).
The control of viral infection by tripartite motif proteins and cyclophilin A.
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Retrovirology,
4,
40.
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I.P.Fabrichny,
P.Leone,
G.Sulzenbacher,
D.Comoletti,
M.T.Miller,
P.Taylor,
Y.Bourne,
and
P.Marchot
(2007).
Structural analysis of the synaptic protein neuroligin and its beta-neurexin complex: determinants for folding and cell adhesion.
|
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Neuron,
56,
979-991.
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PDB codes:
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M.S.García-Ayllón,
M.X.Silveyra,
N.Andreasen,
S.Brimijoin,
K.Blennow,
and
J.Sáez-Valero
(2007).
Cerebrospinal fluid acetylcholinesterase changes after treatment with donepezil in patients with Alzheimer's disease.
|
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J Neurochem,
101,
1701-1711.
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R.R.Jameson,
F.J.Seidler,
and
T.A.Slotkin
(2007).
Nonenzymatic functions of acetylcholinesterase splice variants in the developmental neurotoxicity of organophosphates: chlorpyrifos, chlorpyrifos oxon, and diazinon.
|
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Environ Health Perspect,
115,
65-70.
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T.Schaller,
L.M.Ylinen,
B.L.Webb,
S.Singh,
and
G.J.Towers
(2007).
Fusion of cyclophilin A to Fv1 enables cyclosporine-sensitive restriction of human and feline immunodeficiency viruses.
|
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J Virol,
81,
10055-10063.
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Y.Cheng,
J.K.Suen,
Z.Radić,
S.D.Bond,
M.J.Holst,
and
J.A.McCammon
(2007).
Continuum simulations of acetylcholine diffusion with reaction-determined boundaries in neuromuscular junction models.
|
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Biophys Chem,
127,
129-139.
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A.De Jaco,
D.Comoletti,
Z.Kovarik,
G.Gaietta,
Z.Radic,
O.Lockridge,
M.H.Ellisman,
and
P.Taylor
(2006).
A mutation linked with autism reveals a common mechanism of endoplasmic reticulum retention for the alpha,beta-hydrolase fold protein family.
|
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J Biol Chem,
281,
9667-9676.
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D.Rochu,
C.Cléry-Barraud,
F.Renault,
A.Chevalier,
C.Bon,
and
P.Masson
(2006).
Capillary electrophoresis versus differential scanning calorimetry for the analysis of free enzyme versus enzyme-ligand complexes: in the search of the ligand-free status of cholinesterases.
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Electrophoresis,
27,
442-451.
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J.M.Bui,
and
J.A.McCammon
(2006).
Protein complex formation by acetylcholinesterase and the neurotoxin fasciculin-2 appears to involve an induced-fit mechanism.
|
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Proc Natl Acad Sci U S A,
103,
15451-15456.
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J.P.Colletier,
D.Fournier,
H.M.Greenblatt,
J.Stojan,
J.L.Sussman,
G.Zaccai,
I.Silman,
and
M.Weik
(2006).
Structural insights into substrate traffic and inhibition in acetylcholinesterase.
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EMBO J,
25,
2746-2756.
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PDB codes:
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L.M.Ylinen,
Z.Keckesova,
B.L.Webb,
R.J.Gifford,
T.P.Smith,
and
G.J.Towers
(2006).
Isolation of an active Lv1 gene from cattle indicates that tripartite motif protein-mediated innate immunity to retroviral infection is widespread among mammals.
|
| |
J Virol,
80,
7332-7338.
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M.L.Mayer
(2006).
Glutamate receptors at atomic resolution.
|
| |
Nature,
440,
456-462.
|
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P.J.Atzberger,
and
C.S.Peskin
(2006).
A Brownian Dynamics model of kinesin in three dimensions incorporating the force-extension profile of the coiled-coil cargo tether.
|
| |
Bull Math Biol,
68,
131-160.
|
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R.H.Meltzer,
E.Thompson,
K.V.Soman,
X.Z.Song,
J.O.Ebalunode,
T.G.Wensel,
J.M.Briggs,
and
S.E.Pedersen
(2006).
Electrostatic steering at acetylcholine binding sites.
|
| |
Biophys J,
91,
1302-1314.
|
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R.Pattanayek,
D.R.Williams,
S.Pattanayek,
Y.Xu,
T.Mori,
C.H.Johnson,
P.L.Stewart,
and
M.Egli
(2006).
Analysis of KaiA-KaiC protein interactions in the cyano-bacterial circadian clock using hybrid structural methods.
|
| |
EMBO J,
25,
2017-2028.
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PDB code:
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S.Cursi,
A.Rufini,
V.Stagni,
I.Condò,
V.Matafora,
A.Bachi,
A.P.Bonifazi,
L.Coppola,
G.Superti-Furga,
R.Testi,
and
D.Barilà
(2006).
Src kinase phosphorylates Caspase-8 on Tyr380: a novel mechanism of apoptosis suppression.
|
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EMBO J,
25,
1895-1905.
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Y.Bourne,
Z.Radic,
G.Sulzenbacher,
E.Kim,
P.Taylor,
and
P.Marchot
(2006).
Substrate and product trafficking through the active center gorge of acetylcholinesterase analyzed by crystallography and equilibrium binding.
|
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J Biol Chem,
281,
29256-29267.
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PDB codes:
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Y.P.Pang
(2006).
Novel acetylcholinesterase target site for malaria mosquito control.
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PLoS ONE,
1,
e58.
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Z.Keckesova,
L.M.Ylinen,
and
G.J.Towers
(2006).
Cyclophilin A renders human immunodeficiency virus type 1 sensitive to Old World monkey but not human TRIM5 alpha antiviral activity.
|
| |
J Virol,
80,
4683-4690.
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A.S.Ramos,
and
S.Techert
(2005).
Influence of the water structure on the acetylcholinesterase efficiency.
|
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Biophys J,
89,
1990-2003.
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B.I.Yeh,
Y.K.Kim,
W.Jabbar,
and
C.L.Huang
(2005).
Conformational changes of pore helix coupled to gating of TRPV5 by protons.
|
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EMBO J,
24,
3224-3234.
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L.E.Kennard,
J.R.Chumbley,
K.M.Ranatunga,
S.J.Armstrong,
E.L.Veale,
and
A.Mathie
(2005).
Inhibition of the human two-pore domain potassium channel, TREK-1, by fluoxetine and its metabolite norfluoxetine.
|
| |
Br J Pharmacol,
144,
821-829.
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L.M.Ylinen,
Z.Keckesova,
S.J.Wilson,
S.Ranasinghe,
and
G.J.Towers
(2005).
Differential restriction of human immunodeficiency virus type 2 and simian immunodeficiency virus SIVmac by TRIM5alpha alleles.
|
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J Virol,
79,
11580-11587.
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T.Roenneberg,
and
M.Merrow
(2005).
Circadian clocks: translation.
|
| |
Curr Biol,
15,
R470-R473.
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C.H.Johnson,
and
M.Egli
(2004).
Visualizing a biological clockwork's cogs.
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| |
Nat Struct Mol Biol,
11,
584-585.
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C.Heurteaux,
N.Guy,
C.Laigle,
N.Blondeau,
F.Duprat,
M.Mazzuca,
L.Lang-Lazdunski,
C.Widmann,
M.Zanzouri,
G.Romey,
and
M.Lazdunski
(2004).
TREK-1, a K+ channel involved in neuroprotection and general anesthesia.
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EMBO J,
23,
2684-2695.
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PDB codes:
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PDB code:
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PDB codes:
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The most recent references are shown first.
Citation data come partly from CiteXplore and partly
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only a partial list as not all journals are covered by
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so more and more references will be included with time.
Where a reference describes a PDB structure, the PDB
codes are
shown on the right.
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