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Substrate Report for: mitoDPP-2

Pro-fluorescent probe attached to cyteine analog containing octanoyl thioester. MitoDPPs localize to the mitochondria via an appended triphenylphosphonium group, which delivers the probe to the mitochondria based on the electrochemical potential. The carbamate-linked APT 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. Pro-fluorescent probe attached to cyteine analog containing octanoyl thioester. Enables live cell imaging of thioesterase activity in mitochondria


General
Type Fluorescent Probe, Piperazine, Benzofuran
Chemical_Nomenclature [3-[4-[6'-[methyl-[(2R)-1-(methylamino)-3-octanoylsulfanyl-1-oxopropan-2-yl]carbamoyl]oxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl]piperazin-1-yl]-3-oxopropyl]-triphenylphosphanium
Canonical SMILES [P+](CCC(N1CCN(CC1)C2=CC3=C(C=C2)C5(C4=C(O3)C=C(C=C4)OC(=O)N([C@H](C(=O)NC)CSC(=O)CCCCCCC)C)C6=C(C(O5)=O)C=CC=C6)=O)(C7=CC=CC=C7)(C8=CC=CC=C8)C9=CC=CC=C9.[F-] CCCCCCCC(=O)SCC(C(=O)NC)N(C)C(=O)OC1=CC2=C(C=C1)C3(C4=C(O2)C=C(C=C4)N5CCN(CC5)C(=O)CC[P+](C6=CC=CC=C6)(C7=CC=CC=C7)C8=CC=CC=C8)C9=CC=CC=C9C(=O)O3
InChI InChI=1S/C59H61N4O8PS.FH/c1-4-5-6-7-17-28-55(65)73-41-51(56(66)60-2)61(3)58(68)69-43-30-32-50-53(40-43)70-52-39-42(29-31-49(52)59(50)48-27-19-18-26-47(48)57(67)71-59)62-34-36-63(37-35-62)54(64)33-38-72(44-20-11-8-12-21-44,45-22-13-9-14-23-45)46-24-15-10-16-25-46;/h8-16,18-27,29-32,39-40,51H,4-7,17,28,33-38,41H2,1-3H3;1H/t51-,59?;/m0./s1 InChI=1S/C59H61N4O8PS/c1-4-5-6-7-17-28-55(65)73-41-51(56(66)60-2)61(3)58(68)69-43-30-32-50-53(40-43)70-52-39-42(29-31-49(52)59(50)48-27-19-18-26-47(48)57(67)71-59)62-34-36-63(37-35-62)54(64)33-38-72(44-20-11-8-12-21-44,45-22-13-9-14-23-45)46-24-15-10-16-25-46/h8-16,18-27,29-32,39-40,51H,4-7,17,28,33-38,41H2,1-3H3/p+1/t51-,59?/m0/s1
InChIKey JGCKOSKUFLQGEB-PZXRBRNOSA-N CJVHXLDTLYVANM-HLYGUMIZSA-O
Other name(s)
________________________________________________________________________________________________
MW|1037.19
Formula|C59H62FN4O8PS
CAS_number|
PubChem|139033751
UniChem|JGCKOSKUFLQGEB-PZXRBRNOSA-N, CJVHXLDTLYVANM-HLYGUMIZSA-O
IUPHAR|
Wikipedia|

Target
Families | mitoDPP-2 ligand of proteins in family: ABHD10
Protein | mouse-abhda, human-ABHD10

References:
Search PubMed for references concerning: mitoDPP-2
    Title: Activity-Based Sensing of S-Depalmitoylases: Chemical Technologies and Biological Discovery
    Azizi SA, Kathayat RS, Dickinson BC
    Ref: Acc Chem Res, 52:3029, 2019 : PubMed

            

    Title: ABHD10 is an S-depalmitoylase affecting redox homeostasis through peroxiredoxin-5
    Cao Y, Qiu T, Kathayat RS, Azizi SA, Thorne AK, Ahn D, Fukata Y, Fukata M, Rice PA, Dickinson BC
    Ref: Nat Chemical Biology, 15:1232, 2019 : PubMed

            

    Title: Active and dynamic mitochondrial S-depalmitoylation revealed by targeted fluorescent probes
    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 : PubMed