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Substrate Report for: mitoDPP-2

Name Class
mitoDPP-2TypeFluorescent Probe
Piperazine
Benzofuran
Xanthene
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
FormulaC59H62FN4O8PS
MW1037.19
PaperKathayat_2018_Nat.Commun_9_334
Azizi_2019_Acc.Chem.Res_52_3029
Cao_2019_Nat.Chem.Biol_15_1232
CommentPro-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
Gene_locusmouse-abhda
human-ABHD10
CID139033751
FamilyABHD10
InChIKeyJGCKOSKUFLQGEB-PZXRBRNOSA-N
CJVHXLDTLYVANM-HLYGUMIZSA-O
CanonicalSMILES[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
InChIInChI=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

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Mail to: Nicolas Lenfant, Thierry Hotelier, Yves Bourne, Pascale Marchot and Arnaud Chatonnet.
Please cite: Lenfant 2013 Nucleic.Acids.Res. or Marchot Chatonnet 2012 Prot.Pept Lett.
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