title: Synthesis and evaluation of fluorogenic substrates for phospholipase D and phospholipase C.
abstract: Fluorogenic analogues of phosphatidylcholine and lysophosphatidylcholine, DDPB and lysoDDPB, were synthesized by an enzyme-assisted strategy. The analogues were evaluated as substrates for phospholipases C and D and lysophospholipase D. DDPB was cleaved by bacterial and plant phospholipase D (PLD) enzymes and represents the first direct fluorogenic substrate for real-time measurement of PLD activity. Both fluorogenic substrates have potential in screening for PLD and PC-PLC inhibitors and for monitoring spatiotemporal changes in PLD activity in cells. [structure: see text]
authors.affiliation: Department of Medicinal Chemistry, University of Utah, 419 Wakara Way, Suite 205, Salt Lake City, UT 84108, USA.
authors.forename: Tyler M
authors.initials: TM
authors.lastname: Rose
authors.forename: Glenn D
authors.initials: GD
authors.lastname: Prestwich
mesh_terms: D001409:Bacillus cereus / Q000201:enzymology; D003016:Clostridium perfringens / Q000201:enzymology; D004789:Enzyme Activation / Q000502:physiology; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000378:metabolism; D008244:Lysophosphatidylcholines / Q000138:chemical synthesis* / Q000378:metabolism; D010713:Phosphatidylcholines / Q000138:chemical synthesis* / Q000378:metabolism; D010739:Phospholipase D / Q000737:chemistry* / Q000378:metabolism*; D010727:Phosphoric Diester Hydrolases / Q000378:metabolism; D013111:Spider Venoms / Q000201:enzymology / Q000378:metabolism; D010738:Type C Phospholipases / Q000737:chemistry* / Q000378:metabolism*
chemical_list: D005456:Fluorescent Dyes; D008244:Lysophosphatidylcholines; D010713:Phosphatidylcholines; D013111:Spider Venoms; C055161:loxosceles venom; D010727:Phosphoric Diester Hydrolases; D010738:Type C Phospholipases; D010739:Phospholipase D