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 (21)
| Title : Missense variants in CMS22 patients reveal that PREPL has both enzymatic and non-enzymatic functions - Monnens_2024_JCI.Insight__e179276 |
| Author(s) : Monnens Y , Theodoropoulou A , Rosier K , Bhalla K , Mahy A , Vanhoutte R , Meulemans S , Cavani E , Antanasijevic A , Lemmens I , Lee JA , Spellicy CJ , Schroer RJ , Maselli RA , Laverty CG , Agostinis P , Pagliarini DJ , Verhelst S , Marcaida MJ , Rochtus A , Dal Peraro M , Creemers JW |
| Ref : JCI Insight , : , 2024 |
| Abstract : |
| PubMedSearch : Monnens_2024_JCI.Insight__e179276 |
| PubMedID: 39078710 |
| Gene_locus related to this paper: human-PREPL |
| 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 : 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 : 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 : 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 |