Depalmitoylation-probe-2
Pro-fluorescent probe attached to cysteine analog containing octanoyl thioester. Small molecule probes that become fluorescent upon S-depalmitoylase enzymatic activity. The carbamate-linked APT (acyl protein thioesterase) substrate forces the fluorophore into the lactone-closed, non-fluorescent form. Cleavage of the thioester by reaction with an APT releases the thiol, which rapidly cleaves the carbamate, generating a fluorescent product. Enables live cell imaging of thioesterase activity in cytosol
General
Type : Fluorescent Probe, Benzofuran, Xanthene
Chemical_Nomenclature : S-[(2R)-2-[[6'-(dimethylamino)-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl]oxycarbonyl-methylamino]-3-(methylamino)-3-oxopropyl] octanethioate
Canonical SMILES : CCCCCCCC(=O)SCC(C(=O)NC)N(C)C(=O)OC1=CC2=C(C=C1)C3(C4=C(O2)C=C(C=C4)N(C)C)C5=CC=CC=C5C(=O)O3
InChI : InChI=1S\/C36H41N3O7S\/c1-6-7-8-9-10-15-32(40)47-22-29(33(41)37-2)39(5)35(43)44-24-17-19-28-31(21-24)45-30-20-23(38(3)4)16-18-27(30)36(28)26-14-12-11-13-25(26)34(42)46-36\/h11-14,16-21,29H,6-10,15,22H2,1-5H3,(H,37,41)\/t29-,36?\/m0\/s1
InChIKey : GPDHAAKCLSSHTR-FIMWSPJOSA-N
Other name(s) : DPP-2 || depalmitoylation probe-2 || J3.628.677F || Methyl[(R)-1-(methylcarbamoyl)-2-(octanoylthio)ethyl]carbamic acid [3'-oxo-6-(dimethylamino)spiro[9H-xanthene-9,1'(3'H)-isobenzofuran]-3-yl] ester || S-((2R)-2-((((3'-(dimethylamino)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthen]-6'-yl)oxy)carbonyl)(methyl)amino)-3-(methylamino)-3-oxopropyl) octanethioate
MW : 659.8
Formula : C36H41N3O7S
CAS_number :
PubChem : 122362653
UniChem : GPDHAAKCLSSHTR-FIMWSPJOSA-N
Target
Structures : No structure
Families : LYsophospholipase_carboxylesterase, ABHD17-depalmitoylase, ABHD10
References (2)
| Title : Active and dynamic mitochondrial S-depalmitoylation revealed by targeted fluorescent probes - Kathayat_2018_Nat.Commun_9_334 |
| Author(s) : Kathayat RS , Cao Y , Elvira PD , Sandoz PA , Zaballa ME , Springer MZ , Drake LE , Macleod KF , van der Goot FG , Dickinson BC |
| Ref : Nat Commun , 9 :334 , 2018 |
| Abstract : |
| PubMedSearch : Kathayat_2018_Nat.Commun_9_334 |
| PubMedID: 29362370 |
| Gene_locus related to this paper: human-LYPLA1 |
| Title : A fluorescent probe for cysteine depalmitoylation reveals dynamic APT signaling - Kathayat_2017_Nat.Chem.Biol_13_150 |
| Author(s) : Kathayat RS , Elvira PD , Dickinson BC |
| Ref : Nat Chemical Biology , 13 :150 , 2017 |
| Abstract : |
| PubMedSearch : Kathayat_2017_Nat.Chem.Biol_13_150 |
| PubMedID: 27992880 |