Photoaffinity study of the cellular interactions of ilimaquinone.
The marine sponge metabolite ilimaquinone (1) displays a broad range of biological activities. To better understand the effects of this natural product, a photoaffinity analogue was synthesized and used to probe the cellular interactions of ilimaquinone. Irradiation of photoaffinity probe 5 with liver cytosol in the presence and absence of excess competitive inhibitor 2 suggests that S-adenosylhomocysteinase is an important intracellular target of ilimaquinone.
Radeke
H S
HS
Eugene F. Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02167-3860, USA.
Snapper
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ML
D043383:Adenosylhomocysteinase; D000818:Animals; D001386:Azides / Q000138:chemical synthesis / Q000528:radiation effects; D002417:Cattle; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D006867:Hydrolases / Q000378:metabolism; D008099:Liver / Q000187:drug effects* / Q000201:enzymology / Q000528:radiation effects / Q000648:ultrastructure; D009281:Naphthalenes / Q000138:chemical synthesis / Q000528:radiation effects; D019920:Photoaffinity Labels / Q000138:chemical synthesis / Q000528:radiation effects; D011809:Quinones / Q000494:pharmacology*; D014466:Ultraviolet Rays
C116213:2-methoxy-5-chloro-6-((octahydro-trimethyl-((6-(4-azidobenzoate-6-amino)-hexanoy)oxy)-methyl)-5-naphthyl)methyl-1,4-cycohexadiene-2,5-dione; D001386:Azides; D004791:Enzyme Inhibitors; D009281:Naphthalenes; D019920:Photoaffinity Labels; D011809:Quinones; C067346:illimaquinone; D006867:Hydrolases; D043383:Adenosylhomocysteinase