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Inhibitor Report for: BW284C51

Inhibitor specific of AChE and used to differentiate AChE activity from BChE activity (inhibited by Iso-OMPA (Austin and Berry 1953) Before this publication distinction of AChE and BChE was difficult: Nu-1250, inhibitor of AChE and Ro-2-0683 or Nu-683 or diisopropylphosphorofluoridate (DFP) ( Hawkins & Mendel,1947) to which BChE appears to be about 100-200 times as sensitive as AChE, were used. Entry of reference human-ACHE
The acetylcholinesterase inhibitor BW284c51 is a potent blocker of Torpedo nicotinic AchRs Olivera et al 2005


General
Type Bisquaternary
Chemical_Nomenclature 1:5-bis(4-allyldimethylammoniumphenyl)-pentan-3-one dibromide
Canonical SMILES C[N+](C)(CC=C)C1=CC=C(C=C1)CCC(=O)CCC2=CC=C(C=C2)[N+](C)(C)CC=C.[Br-].[Br-] C[N+](C)(CC=C)C1=CC=C(C=C1)CCC(=O)CCC2=CC=C(C=C2)[N+](C)(C)CC=C
InChI InChI=1S/C27H38N2O.2BrH/c1-7-21-28(3,4)25-15-9-23(10-16-25)13-19-27(30)20-14-24-11-17-26(18-12-24)29(5,6)22-8-2;;/h7-12,15-18H,1-2,13-14,19-22H2,3-6H3;2*1H/q+2;;/p-2 InChI=1S/C27H38N2O/c1-7-21-28(3,4)25-15-9-23(10-16-25)13-19-27(30)20-14-24-11-17-26(18-12-24)29(5,6)22-8-2/h7-12,15-18H,1-2,13-14,19-22H2,3-6H3/q+2
InChIKey WKDURMTZOWGWTD-UHFFFAOYSA-L ZAEXMNKDGJNLTA-UHFFFAOYSA-N
Other name(s) BW297C50 is the corresponding diiodide ; EBW ; CHEMBL140020 ; BW-28C51 ; SCHEMBL7449688 ; ZINC3814201 ; BW 284 C 51 ; BW-284-C-51
________________________________________________________________________________________________
MW|566.4
Formula|C27H38N2OBr2
CAS_number|402-40-4
PubChem|9820, 1338
UniChem|WKDURMTZOWGWTD-UHFFFAOYSA-L, ZAEXMNKDGJNLTA-UHFFFAOYSA-N
IUPHAR|6600
Wikipedia|

Target
Families | BW284C51 ligand of proteins in family: ACHE
Stucture | 3 structures: 1E3Q, 6O50, 6O52
Protein | torca-ACHE, human-ACHE

References:
Search PubMed for references concerning: BW284C51

24 more
    Title: Cloning and expression of acetylcholinesterase from Bungarus fasciatus venom. A new type of cooh-terminal domain; involvement of a positively charged residue in the peripheral site
    Cousin X, Bon S, Duval N, Massoulie J, Bon C
    Ref: Journal of Biological Chemistry, 271:15099, 1996 : PubMed

            

    Title: Acetylcholinesterase activity of Xenopus laevis oocytes
    Gundersen CB, Miledi R
    Ref: Neuroscience, 10:1487, 1983 : PubMed

            

    Title: Acetylcholinesterase and butyrylcholinesterase activity in the atria of the heart of adult albino rats
    Slavikova J, Vlk J, Hlavickova V
    Ref: Physiol Bohemoslov, 31:407, 1982 : PubMed

            


bunfa-ACHE
MutationKiKsiIc50SubstrateConditionPaper
K285D 10.8 & 2.4 nM 14.4 & 0.8 nM - Acetylthiocholine T25C IS 50 mM phosphate Cousin_1996_J.Biol.Chem_271_15099
M70Y 7.9 & 1.3 nM 17.5 & 1.4 nM - Acetylthiocholine T25C IS 50 mM phosphate Cousin_1996_J.Biol.Chem_271_15099
M70Y/K285D 3.8 & 0.2 nM 9.3 & 0.1 nM - Acetylthiocholine T25C IS 50 mM phosphate Cousin_1996_J.Biol.Chem_271_15099
WT 16.9 & 1.6 nM 28.9 & 0.8 nM - Acetylthiocholine T25C IS 50 mM phosphate Cousin_1996_J.Biol.Chem_271_15099

chick-ACHE
MutationKiKsiIc50SubstrateConditionPaper
WT 240 nM - - Acetylthiocholine 100mM NaCl 50mM Tris pH7.4 Eichler_1994_Mol.Pharmacol_45_335

human-ACHE
MutationKiKsiIc50SubstrateConditionPaper
> Mutations for human-ACHE (30)

human-BCHE
MutationKiKsiIc50SubstrateConditionPaper
> Mutations for human-BCHE (24)

mouse-ACHE
MutationKiKsiIc50SubstrateConditionPaper
> Mutations for mouse-ACHE (12)

mouse-BCHE
MutationKiKsiIc50SubstrateConditionPaper
WT 11300 & 400 nM 42000000 & 5000000 nM - Acetylthiocholine 100mM NaP pH7.0 T22C eq3.gif sch3.gif Radic_1993_Biochemistry_32_12074

torma-ACHE
MutationKiKsiIc50SubstrateConditionPaper
WT 2 nM - - Acetylthiocholine 100mM NaCl 50mM Tris pH7.4 Eichler_1994_Mol.Pharmacol_45_335
WT 15.1 & 0.7 nM 63.6 & 8.4 nM - Acetylthiocholine T25C IS 50 mM phosphate Cousin_1996_J.Biol.Chem_271_15099

WT Kinetics
Kinetic parametersKiKsiIc50SubstrateConditionsPapers
bunfa-ACHE16.9 & 1.6 nM28.9 & 0.8 nM- Acetylthiocholine T25C IS 50 mM phosphate Cousin_1996_J.Biol.Chem_271_15099
chick-ACHE240 nM-- Acetylthiocholine 100mM NaCl 50mM Tris pH7.4 Eichler_1994_Mol.Pharmacol_45_335
human-ACHE10 nM-- Acetylthiocholine 50mM Na phosphate pH8 Barak_1994_J.Biol.Chem_269_6296
human-ACHE170000 nM-- Acetylthiocholine T25C IS 50 mM phosphate Kaplan_2001_Biochemistry_40_7433
human-ACHE--50 nM Acetylthiocholine pH8 T27C 50mM Na phosphate Shafferman_1992_EMBO.J_11_3561
human-ACHE0.13 uM-- Butyrylthiocholine 50mM NaPhosphate pH7.4 Loewenstein-Lichtenstein_1996_Mol.Pharmacol_50_1423
human-BCHE14000 nM-- Acetylthiocholine T25C IS 50 mM phosphate Kaplan_2001_Biochemistry_40_7433
human-BCHE480 & 110 uM-- Butyrylthiocholine 50mM NaPhosphate pH7.4 Loewenstein-Lichtenstein_1996_Mol.Pharmacol_50_1423
mouse-ACHE2.8 & 1.0 nM4.8 & 1.8 nM- Acetylthiocholine 100mM NaP pH7.0 T22C eq3.gif sch3.gif Radic_1993_Biochemistry_32_12074
mouse-BCHE11300 & 400 nM42000000 & 5000000 nM- Acetylthiocholine 100mM NaP pH7.0 T22C eq3.gif sch3.gif Radic_1993_Biochemistry_32_12074
torma-ACHE2 nM-- Acetylthiocholine 100mM NaCl 50mM Tris pH7.4 Eichler_1994_Mol.Pharmacol_45_335
torma-ACHE15.1 & 0.7 nM63.6 & 8.4 nM- Acetylthiocholine T25C IS 50 mM phosphate Cousin_1996_J.Biol.Chem_271_15099