Tz2Pa6-syn1

The AChE inhibitor TZ2PA6 results from 1,3-dipolar cycloaddition (click chemistry) between a PAS inhibitor (phenylphenanthridinium) equipped with an acetylene group at the end of a flexible methylene chain and an active site inhibitor (tacrine)equipped with an azide group at the end of a methylene chain

General

Type : Acridine, Phenanthridinium, Derivative of Tacrine, Alkyl linked bis-ligand, Triazol

Chemical_Nomenclature : 3,8-Diamino-6-Phenyl-5-[6-[1-[2-[(1,2,3,4-tetrahydro-9-acridinyl)amino]ethyl]-1H-1,2,3-triazol-5-yl]hexyl] phenanthridinium

Canonical SMILES : C1CCC2=NC3=CC=CC=C3C(=C2C1)NCCN4C(=CN=N4)CCCCCC[N+]5=C6C=C(C=CC6=C7C=CC(=CC7=C5C8=CC=CC=C8)N)N

InChI : InChI=1S\/C42H44N8\/c43-30-19-21-33-34-22-20-31(44)27-40(34)49(42(37(33)26-30)29-12-4-3-5-13-29)24-11-2-1-6-14-32-28-46-48-50(32)25-23-45-41-35-15-7-9-17-38(35)47-39-18-10-8-16-36(39)41\/h3-5,7,9,12-13,15,17,19-22,26-28,44H,1-2,6,8,10-11,14,16,18,23-25,43H2,(H,45,47)\/p+1

InChIKey : ISUOMOOYAOQQPZ-UHFFFAOYSA-O

Other name(s) : CHEMBL117651


MW :

Formula : C42H45N8

CAS_number :

PubChem : 5289508

UniChem : ISUOMOOYAOQQPZ-UHFFFAOYSA-O

Target

Families : Tz2Pa6-syn1 ligand of proteins in family
ACHE

Structure :
2XUI 2XUJ 2XUK 2XUP 2XUQ 1Q83

Protein :
mouse-ACHE

References (8)

Title : Steric and Dynamic Parameters Influencing In Situ Cycloadditions to Form Triazole Inhibitors with Crystalline Acetylcholinesterase - Bourne_2016_J.Am.Chem.Soc_138_1611
Author(s) : Bourne Y , Sharpless KB , Taylor P , Marchot P
Ref : Journal of the American Chemical Society , 138 :1611 , 2016
Abstract :
PubMedSearch : Bourne_2016_J.Am.Chem.Soc_138_1611
PubMedID: 26731630
Gene_locus related to this paper: mouse-ACHE

Title : Conformational remodeling of femtomolar inhibitor-acetylcholinesterase complexes in the crystalline state - Bourne_2010_J.Am.Chem.Soc_132_18292
Author(s) : Bourne Y , Radic Z , Taylor P , Marchot P
Ref : Journal of the American Chemical Society , 132 :18292 , 2010
Abstract :
PubMedSearch : Bourne_2010_J.Am.Chem.Soc_132_18292
PubMedID: 21090615
Gene_locus related to this paper: mouse-ACHE

Title : Probing gorge dimensions of cholinesterases by freeze-frame click chemistry - Radic_2008_Chem.Biol.Interact_175_161
Author(s) : Radic Z , Manetsch R , Fournier D , Sharpless KB , Taylor P
Ref : Chemico-Biological Interactions , 175 :161 , 2008
Abstract :
PubMedSearch : Radic_2008_Chem.Biol.Interact_175_161
PubMedID: 18555981

Title : Structural insights into conformational flexibility at the peripheral site and within the active center gorge of AChE - Bourne_2005_Chem.Biol.Interact_157-158_159
Author(s) : Bourne Y , Radic Z , Kolb HC , Sharpless KB , Taylor P , Marchot P
Ref : Chemico-Biological Interactions , 157-158 :159 , 2005
Abstract :
PubMedSearch : Bourne_2005_Chem.Biol.Interact_157-158_159
PubMedID: 16259971

Title : Freeze-frame inhibitor captures acetylcholinesterase in a unique conformation - Bourne_2004_Proc.Natl.Acad.Sci.U.S.A_101_1449
Author(s) : Bourne Y , Kolb HC , Radic Z , Sharpless KB , Taylor P , Marchot P
Ref : Proc Natl Acad Sci U S A , 101 :1449 , 2004
Abstract :
PubMedSearch : Bourne_2004_Proc.Natl.Acad.Sci.U.S.A_101_1449
PubMedID: 14757816
Gene_locus related to this paper: mouse-ACHE

Title : In situ click chemistry: enzyme inhibitors made to their own specifications - Manetsch_2004_J.Am.Chem.Soc_126_12809
Author(s) : Manetsch R , Krasinski A , Radic Z , Raushel J , Taylor P , Sharpless KB , Kolb HC
Ref : Journal of the American Chemical Society , 126 :12809 , 2004
Abstract :
PubMedSearch : Manetsch_2004_J.Am.Chem.Soc_126_12809
PubMedID: 15469276

Title : Cover picture: angew. Chem. Int. Ed. 6\/2002 - Lewis_2002_Angew.Chem.Int.Ed.Engl_41_875
Author(s) : Lewis WG , Green LG , Grynszpan F , Radic Z , Carlier PR , Taylor P , Finn MG , Sharpless KB
Ref : Angew Chem Int Ed Engl , 41 :875 , 2002
Abstract :
PubMedSearch : Lewis_2002_Angew.Chem.Int.Ed.Engl_41_875
PubMedID:

Title : Click chemistry in situ: acetylcholinesterase as a reaction vessel for the selective assembly of a femtomolar inhibitor from an array of building blocks -
Author(s) : Lewis WG , Green LG , Grynszpan F , Radic Z , Carlier PR , Taylor P , Finn MG , Sharpless KB
Ref : Angew Chem Int Ed Engl , 41 :1053 , 2002
PubMedID: 12491310