Ebselen
Ebselen is a organoselenium compound with anti-inflammatory, anti-oxidant and cytoprotective activity. Ebselen acts as a glutathione peroxidase mimetic and is thereby able to prevent cellular damage induced by reactive oxygen species (ROS). In addition, this agent inhibits the activity of a variety of enzymes including nitric oxide synthase (NOS), 5-lipoxygenase, cyclooxygenase, protein kinase C (PKC), NADPH oxidase and gastric H+/K+-ATPase. Furthermore, ebselen may be neuroprotective due to its ability to neutralize free radicals upon NMDA receptor activation thus, reducing lipoperoxidation mediated by glutamate-induced excitotoxicity. Ebselen is a poor inhibitor of AChE. Ebselen inhibited AChE activity with an IC50 of 29uM. Ebselen is an effective inhibitor of the Ag85 complex through covalent modification of a cysteine residue proximal to the Ag85 active site and is therefore a covalent, allosteric inhibitor
General
Type : Organoselenium,Thiol-reactive
Chemical_Nomenclature : 2-phenyl-1,2-benzoselenazol-3-one
Canonical SMILES : C1=CC=C(C=C1)N2C(=O)C3=CC=CC=C3[Se]2
InChI : InChI=1S\/C13H9NOSe\/c15-13-11-8-4-5-9-12(11)16-14(13)10-6-2-1-3-7-10\/h1-9H
InChIKey : DYEFUKCXAQOFHX-UHFFFAOYSA-N
Other name(s) : 2-Phenyl-1,2-benzisoselenazol-3(2H)-one,Ebselene,Ebseleno,Ebselenum
MW : 274.17
Formula : C13H9NOSe
CAS_number : 60940-34-3
PubChem : 3194
UniChem : DYEFUKCXAQOFHX-UHFFFAOYSA-N
IUPHAR :
Wikipedia : Ebselen
Target
Families : Ebselen ligand of proteins in family: A85-Mycolyl-transferase
Stucture :
Protein : myctu-a85c
References (8)
| Title : Ebselen inhibits the activity of acetylcholinesterase globular isoform G4 in vitro and attenuates scopolamine-induced amnesia in mice - Martini_2018_J.Cell.Biochem_119_5598 |
| Author(s) : Martini F , Pesarico AP , Bruning CA , Zeni G , Nogueira CW |
| Ref : Journal of Cellular Biochemistry , 119 :5598 , 2018 |
| Abstract : Martini_2018_J.Cell.Biochem_119_5598 |
| ESTHER : Martini_2018_J.Cell.Biochem_119_5598 |
| PubMedSearch : Martini_2018_J.Cell.Biochem_119_5598 |
| PubMedID: 29405440 |
| Title : Inhibitory effect of ebselen on cerebral acetylcholinesterase activity in vitro: kinetics and reversibility of inhibition - Martini_2015_Curr.Pharm.Des_21_920 |
| Author(s) : Martini F , Bruning CA , Soares SM , Nogueira CW , Zeni G |
| Ref : Curr Pharm Des , 21 :920 , 2015 |
| Abstract : Martini_2015_Curr.Pharm.Des_21_920 |
| ESTHER : Martini_2015_Curr.Pharm.Des_21_920 |
| PubMedSearch : Martini_2015_Curr.Pharm.Des_21_920 |
| PubMedID: 25312723 |
| Title : Synthesis and biological evaluation of a new series of ebselen derivatives as glutathione peroxidase (GPx) mimics and cholinesterase inhibitors against Alzheimer's disease - Luo_2014_Bioorg.Med.Chem_22_1355 |
| Author(s) : Luo Z , Liang L , Sheng J , Pang Y , Li J , Huang L , Li X |
| Ref : Bioorganic & Medicinal Chemistry , 22 :1355 , 2014 |
| Abstract : Luo_2014_Bioorg.Med.Chem_22_1355 |
| ESTHER : Luo_2014_Bioorg.Med.Chem_22_1355 |
| PubMedSearch : Luo_2014_Bioorg.Med.Chem_22_1355 |
| PubMedID: 24461494 |
| Title : Synthesis and Evaluation of Multi-Target-Directed Ligands against Alzheimer's Disease Based on the Fusion of Donepezil and Ebselen - Luo_2013_J.Med.Chem_56_9089 |
| Author(s) : Luo Z , Sheng J , Sun Y , Lu C , Yan J , Liu A , Luo HB , Huang L , Li X |
| Ref : Journal of Medicinal Chemistry , 56 :9089 , 2013 |
| Abstract : Luo_2013_J.Med.Chem_56_9089 |
| ESTHER : Luo_2013_J.Med.Chem_56_9089 |
| PubMedSearch : Luo_2013_J.Med.Chem_56_9089 |
| PubMedID: 24160297 |
| Title : Novel tacrine-ebselen hybrids with improved cholinesterase inhibitory, hydrogen peroxide and peroxynitrite scavenging activity - Mao_2013_Bioorg.Med.Chem.Lett_23_6737 |
| Author(s) : Mao F , Chen J , Zhou Q , Luo Z , Huang L , Li X |
| Ref : Bioorganic & Medicinal Chemistry Lett , 23 :6737 , 2013 |
| Abstract : Mao_2013_Bioorg.Med.Chem.Lett_23_6737 |
| ESTHER : Mao_2013_Bioorg.Med.Chem.Lett_23_6737 |
| PubMedSearch : Mao_2013_Bioorg.Med.Chem.Lett_23_6737 |
| PubMedID: 24220172 |
| Title : Mechanism of inhibition of Mycobacterium tuberculosis antigen 85 by ebselen - Favrot_2013_Nat.Commun_4_2748 |
| Author(s) : Favrot L , Grzegorzewicz AE , Lajiness DH , Marvin RK , Boucau J , Isailovic D , Jackson M , Ronning DR |
| Ref : Nat Commun , 4 :2748 , 2013 |
| Abstract : Favrot_2013_Nat.Commun_4_2748 |
| ESTHER : Favrot_2013_Nat.Commun_4_2748 |
| PubMedSearch : Favrot_2013_Nat.Commun_4_2748 |
| PubMedID: 24193546 |
| Gene_locus related to this paper: myctu-a85c |
| Title : Pre-treatment with ebselen and vitamin E modulate acetylcholinesterase activity: interaction with demyelinating agents - Mazzanti_2009_Int.J.Dev.Neurosci_27_73 |
| Author(s) : Mazzanti CM , Spanevello R , Ahmed M , Pereira LB , Goncalves JF , Correa M , Schmatz R , Stefanello N , Leal DB , Mazzanti A , Ramos AT , Martins TB , Danesi CC , Graca DL , Morsch VM , Schetinger MR |
| Ref : Int J Developmental Neuroscience , 27 :73 , 2009 |
| Abstract : Mazzanti_2009_Int.J.Dev.Neurosci_27_73 |
| ESTHER : Mazzanti_2009_Int.J.Dev.Neurosci_27_73 |
| PubMedSearch : Mazzanti_2009_Int.J.Dev.Neurosci_27_73 |
| PubMedID: 18930802 |
| Title : The neuroprotective agent ebselen modifies NMDA receptor function via the redox modulatory site - Herin_2001_J.Neurochem_78_1307 |
| Author(s) : Herin GA , Du S , Aizenman E |
| Ref : Journal of Neurochemistry , 78 :1307 , 2001 |
| Abstract : Herin_2001_J.Neurochem_78_1307 |
| ESTHER : Herin_2001_J.Neurochem_78_1307 |
| PubMedSearch : Herin_2001_J.Neurochem_78_1307 |
| PubMedID: 11579139 |