S9B

Biotinylated covalent inhibitors of serine esterases allow detection and rapid isolation of neuropathy target esterase (NTE). This enzyme is the primary target site for those organophosphorus esters (OPs) which cause delayed neuropathy. One moiety of S9B (structurally similar to the active metabolite of TOCP) reacts specifically with the catalytic serine residue of NTE; the second moiety is a biotin molecule that allow the NTE-S9B adduct to be captured on avidin-Sepharose.

General

Type : Organophosphate, Cyclic OP, NTE inhibitor, Not A\/B H target, Sulfur Compound, Biotin derivative

Chemical_Nomenclature : 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[9-[(2-oxo-4H-1,3,2lambda5-benzodioxaphosphinin-2-yl)amino]nonyl]pentanamide

Canonical SMILES : C1C2C(C(S1)CCCCC(=O)NCCCCCCCCCNP3(=O)OCC4=CC=CC=C4O3)NC(=O)N2

InChI : InChI=1S\/C26H41N4O5PS\/c31-24(15-9-8-14-23-25-21(19-37-23)29-26(32)30-25)27-16-10-4-2-1-3-5-11-17-28-36(33)34-18-20-12-6-7-13-22(20)35-36\/h6-7,12-13,21,23,25H,1-5,8-11,14-19H2,(H,27,31)(H,28,33)(H2,29,30,32)\/t21-,23-,25-,36?\/m0\/s1

InChIKey : JZSQBHPKLLZQAH-NYWSWALVSA-N

Other name(s) : 1-(saligenin cyclic phospho)-9-biotinyldiaminononane  ||  DTXSID70935850  ||  N-(9-(4H-1,3,2-Benzodioxaphosphorin-2-ylamino)nonyl)hexahydro-2-oxo-1H-thieno(3,4-d)imidazole-4-pentanamide P-oxide, (3aS-(3aalpha,4beta,6aalpha))-


MW : 552.7

Formula : C26H41N4O5PS

CAS_number : 158040-84-7

PubChem : 133040

UniChem : JZSQBHPKLLZQAH-NYWSWALVSA-N

Target

References (3)

Title : Inhibition with spontaneous reactivation and the ongoing inhibition effect of esterases by biotinylated organophosphorus compounds: S9B as a model - Estevez_2010_Chem.Biol.Interact_187_397
Author(s) : Estevez J , Barril J , Vilanova E
Ref : Chemico-Biological Interactions , 187 :397 , 2010
Abstract :
PubMedSearch : Estevez_2010_Chem.Biol.Interact_187_397
PubMedID: 20493177

Title : Neuropathy target esterase and a homologous Drosophila neurodegeneration-associated mutant protein contain a novel domain conserved from bacteria to man - Lush_1998_Biochem.J_332 ( Pt 1)_1
Author(s) : Lush MJ , Li Y , Read DJ , Willis AC , Glynn P
Ref : Biochemical Journal , 332 ( Pt 1) :1 , 1998
Abstract :
PubMedSearch : Lush_1998_Biochem.J_332 ( Pt 1)_1
PubMedID: 9576844

Title : Synthesis and characterization of a biotinylated organophosphorus ester for detection and affinity purification of a brain serine esterase: neuropathy target esterase - Glynn_1994_Biochem.J_301 ( Pt 2)_551
Author(s) : Glynn P , Read DJ , Guo R , Wylie S , Johnson MK
Ref : Biochemical Journal , 301 ( Pt 2) :551 , 1994
Abstract :
PubMedSearch : Glynn_1994_Biochem.J_301 ( Pt 2)_551
PubMedID: 8043002