FP-Biotin

Serine Hydrolase probe consisting of a tag linked to a fluorophosphonate (FP) group, whichcovalently labels serines of enzymatically active serine hydrolases. ABPP-Probe (activity based protein profiling probe). Useful as ABPP probe but not specific: Labels lots of non serine hydrolases

General

Type : Organophosphate, ABPP-Probe, Imidazole, Sulfur Compound, Biotin derivative

Chemical_Nomenclature : 10-[ethoxy(fluoro)phosphoryl]-N-[5-[5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanoylamino]pentyl]decanamide

Canonical SMILES : CCOP(=O)(CCCCCCCCCC(=O)NCCCCCNC(=O)CCCCC1C2C(CS1)NC(=O)N2)F

InChI : InChI=1S\/C27H50FN4O5PS\/c1-2-37-38(28,36)20-14-7-5-3-4-6-9-16-24(33)29-18-12-8-13-19-30-25(34)17-11-10-15-23-26-22(21-39-23)31-27(35)32-26\/h22-23,26H,2-21H2,1H3,(H,29,33)(H,30,34)(H2,31,32,35)

InChIKey : ZIFSFLGSUTZFCP-UHFFFAOYSA-N

Other name(s) : 10-Fluoroethoxyphosphinyl-N-biotinamidopentyldecanamide  ||  SCHEMBL13743155  ||  CTK8E8183  ||  RT-013047


MW : 592.75

Formula : C27H50FN4O5PS

CAS_number : 259270-28-5

PubChem : 24762158

UniChem : ZIFSFLGSUTZFCP-UHFFFAOYSA-N

Target

References (20)

Title : DPP9's Enzymatic Activity and Not Its Binding to CARD8 Inhibits Inflammasome Activation - Griswold_2019_ACS.Chem.Biol_14_2424
Author(s) : Griswold AR , Ball DP , Bhattacharjee A , Chui AJ , Rao SD , Taabazuing CY , Bachovchin DA
Ref : ACS Chemical Biology , 14 :2424 , 2019
Abstract :
PubMedSearch : Griswold_2019_ACS.Chem.Biol_14_2424
PubMedID: 31525884
Gene_locus related to this paper: human-DPP9

Title : A novel quantification method for serine hydrolases in cellular expression system using fluorophosphonate-biotin probe - Abdel-Daim_2018_Eur.J.Pharm.Sci_114_267
Author(s) : Abdel-Daim A , Ohura K , Imai T
Ref : Eur J Pharm Sci , 114 :267 , 2018
Abstract :
PubMedSearch : Abdel-Daim_2018_Eur.J.Pharm.Sci_114_267
PubMedID: 29289670

Title : Multicomponent mapping of boron chemotypes furnishes selective enzyme inhibitors - Tan_2017_Nat.Commun_8_1760
Author(s) : Tan J , Cognetta AB, 3rd , Diaz DB , Lum KM , Adachi S , Kundu S , Cravatt BF , Yudin AK
Ref : Nat Commun , 8 :1760 , 2017
Abstract :
PubMedSearch : Tan_2017_Nat.Commun_8_1760
PubMedID: 29170371
Gene_locus related to this paper: human-ABHD3 , mouse-abhd3

Title : Chemical Proteomics Maps Brain Region Specific Activity of Endocannabinoid Hydrolases - Baggelaar_2017_ACS.Chem.Biol_12_852
Author(s) : Baggelaar MP , van Esbroeck AC , van Rooden EJ , Florea BI , Overkleeft HS , Marsicano G , Chaouloff F , van der Stelt M
Ref : ACS Chemical Biology , 12 :852 , 2017
Abstract :
PubMedSearch : Baggelaar_2017_ACS.Chem.Biol_12_852
PubMedID: 28106377
Gene_locus related to this paper: human-ABHD4 , human-ABHD6 , human-ABHD12 , human-DAGLA , human-MGLL

Title : Detection of dichlorvos adducts in a hepatocyte cell line - Bui-Nguyen_2014_J.Proteome.Res_13_3583
Author(s) : Bui-Nguyen TM , Dennis WE , Jackson DA , Stallings JD , Lewis JA
Ref : J Proteome Res , 13 :3583 , 2014
Abstract :
PubMedSearch : Bui-Nguyen_2014_J.Proteome.Res_13_3583
PubMedID: 24978939

Title : Examination of the carboxylesterase phenotype in human liver - Ross_2012_Arch.Biochem.Biophys_522_44
Author(s) : Ross MK , Borazjani A , Wang R , Crow JA , Xie S
Ref : Archives of Biochemistry & Biophysics , 522 :44 , 2012
Abstract :
PubMedSearch : Ross_2012_Arch.Biochem.Biophys_522_44
PubMedID: 22525521

Title : Covalent binding of the organophosphorus agent FP-biotin to tyrosine in eight proteins that have no active site serine - Grigoryan_2009_Chem.Biol.Interact_180_492
Author(s) : Grigoryan H , Li B , Anderson EK , Xue W , Nachon F , Lockridge O , Schopfer LM
Ref : Chemico-Biological Interactions , 180 :492 , 2009
Abstract :
PubMedSearch : Grigoryan_2009_Chem.Biol.Interact_180_492
PubMedID: 19539807

Title : Tyrosines of human and mouse transferrin covalently labeled by organophosphorus agents: a new motif for binding to proteins that have no active site serine - Li_2009_Toxicol.Sci_107_144
Author(s) : Li B , Schopfer LM , Grigoryan H , Thompson CM , Hinrichs SH , Masson P , Lockridge O
Ref : Toxicol Sci , 107 :144 , 2009
Abstract :
PubMedSearch : Li_2009_Toxicol.Sci_107_144
PubMedID: 18930948

Title : Five tyrosines and two serines in human albumin are labeled by the organophosphorus agent FP-biotin - Ding_2008_Chem.Res.Toxicol_21_1787
Author(s) : Ding SJ , Carr J , Carlson JE , Tong L , Xue W , Li Y , Schopfer LM , Li B , Nachon F , Asojo OA , Thompson CM , Hinrichs SH , Masson P , Lockridge O
Ref : Chemical Research in Toxicology , 21 :1787 , 2008
Abstract :
PubMedSearch : Ding_2008_Chem.Res.Toxicol_21_1787
PubMedID: 18707141

Title : Mass spectrometry identifies covalent binding of soman, sarin, chlorpyrifos oxon, diisopropyl fluorophosphate, and FP-biotin to tyrosines on tubulin: a potential mechanism of long term toxicity by organophosphorus agents - Grigoryan_2008_Chem.Biol.Interact_175_180
Author(s) : Grigoryan H , Schopfer LM , Thompson CM , Terry AV , Masson P , Lockridge O
Ref : Chemico-Biological Interactions , 175 :180 , 2008
Abstract :
PubMedSearch : Grigoryan_2008_Chem.Biol.Interact_175_180
PubMedID: 18502412

Title : A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol - Blankman_2007_Chem.Biol_14_1347
Author(s) : Blankman JL , Simon GM , Cravatt BF
Ref : Chemical Biology , 14 :1347 , 2007
Abstract :
PubMedSearch : Blankman_2007_Chem.Biol_14_1347
PubMedID: 18096503
Gene_locus related to this paper: human-ABHD6 , human-ABHD12 , human-MGLL

Title : Deletion of PREPL, a gene encoding a putative serine oligopeptidase, in patients with hypotonia-cystinuria syndrome - Jaeken_2006_Am.J.Hum.Genet_78_38
Author(s) : Jaeken J , Martens K , Francois I , Eyskens F , Lecointre C , Derua R , Meulemans S , Slootstra JW , Waelkens E , de Zegher F , Creemers JW , Matthijs G
Ref : American Journal of Human Genetics , 78 :38 , 2006
Abstract :
PubMedSearch : Jaeken_2006_Am.J.Hum.Genet_78_38
PubMedID: 16385448
Gene_locus related to this paper: human-PREPL

Title : Naturally occurring mutation Leu307Pro of human butyrylcholinesterase in the Vysya community of India - Manoharan_2006_Pharmacogenet.Genomics_16_461
Author(s) : Manoharan I , Wieseler S , Layer PG , Lockridge O , Boopathy R
Ref : Pharmacogenet Genomics , 16 :461 , 2006
Abstract :
PubMedSearch : Manoharan_2006_Pharmacogenet.Genomics_16_461
PubMedID: 16788378
Gene_locus related to this paper: human-BCHE

Title : Characteristic mass spectral fragments of the organophosphorus agent FP-biotin and FP-biotinylated peptides from trypsin and bovine albumin (Tyr410) - Schopfer_2005_Anal.Biochem_345_122
Author(s) : Schopfer LM , Champion MM , Tamblyn N , Thompson CM , Lockridge O
Ref : Analytical Biochemistry , 345 :122 , 2005
Abstract :
PubMedSearch : Schopfer_2005_Anal.Biochem_345_122
PubMedID: 16125664

Title : Reaction kinetics of biotinylated organophosphorus toxicant, FP-biotin, with human acetylcholinesterase and human butyrylcholinesterase - Schopfer_2005_Chem.Res.Toxicol_18_747
Author(s) : Schopfer LM , Voelker T , Bartels CF , Thompson CM , Lockridge O
Ref : Chemical Research in Toxicology , 18 :747 , 2005
Abstract :
PubMedSearch : Schopfer_2005_Chem.Res.Toxicol_18_747
PubMedID: 15833035

Title : Albumin, a new biomarker of organophosphorus toxicant exposure, identified by mass spectrometry - Peeples_2005_Toxicol.Sci_83_303
Author(s) : Peeples ES , Schopfer LM , Duysen EG , Spaulding R , Voelker T , Thompson CM , Lockridge O
Ref : Toxicol Sci , 83 :303 , 2005
Abstract :
PubMedSearch : Peeples_2005_Toxicol.Sci_83_303
PubMedID: 15525694

Title : Synergistic computational and experimental proteomics approaches for more accurate detection of active serine hydrolases in yeast - Baxter_2004_Mol.Cell.Proteomics_3_209
Author(s) : Baxter SM , Rosenblum JS , Knutson S , Nelson MR , Montimurro JS , Di Gennaro JA , Speir JA , Burbaum JJ , Fetrow JS
Ref : Mol Cell Proteomics , 3 :209 , 2004
Abstract :
PubMedSearch : Baxter_2004_Mol.Cell.Proteomics_3_209
PubMedID: 14645503
Gene_locus related to this paper: yeast-FSH1 , yeast-FSH2 , yeast-FSH3 , yeast-mgll , yeast-ppme1 , yeast-YDR428C , yeast-yfd4 , yeast-YLR118c

Title : Direct visualization of serine hydrolase activities in complex proteomes using fluorescent active site-directed probes - Patricelli_2001_Proteomics_1_1067
Author(s) : Patricelli MP , Giang DK , Stamp LM , Burbaum JJ
Ref : Proteomics , 1 :1067 , 2001
Abstract :
PubMedSearch : Patricelli_2001_Proteomics_1_1067
PubMedID: 11990500

Title : Profiling serine hydrolase activities in complex proteomes - Kidd_2001_Biochemistry_40_4005
Author(s) : Kidd D , Liu Y , Cravatt BF
Ref : Biochemistry , 40 :4005 , 2001
Abstract :
PubMedSearch : Kidd_2001_Biochemistry_40_4005
PubMedID: 11300781

Title : Activity-based protein profiling: the serine hydrolases - Liu_1999_Proc.Natl.Acad.Sci.U.S.A_96_14694
Author(s) : Liu Y , Patricelli MP , Cravatt BF
Ref : Proc Natl Acad Sci U S A , 96 :14694 , 1999
Abstract :
PubMedSearch : Liu_1999_Proc.Natl.Acad.Sci.U.S.A_96_14694
PubMedID: 10611275