title: A triterpene oleanolic acid conjugate with 3-hydroxyflavone derivative as a new membrane probe with two-color ratiometric response.
abstract: We report on the synthesis by coupling of a triterpenoid oleanolic acid with 4'-diethylamino-3-hydroxyflavone (FE) to produce an environment-sensitive biomembrane probe with two-band ratiometric response in fluorescence emission. The synthesized compound (probe FOT) was tested in a series of model solvents and demonstrated the response to solvent polarity and intermolecular hydrogen bonding very similar to that of parent probe FE. Meantime when incorporated into lipid bilayer membranes, it showed new features differing in response between lipids of different surface charges as well as between glycerophospholipids and sphingomyelin. We observed that in the conditions of coexistence of rafts and non-raft structures the probe is excluded from the rafts.
authors: TUBITAK Research Institute for Genetic Engineering and Biotechnology, 41470 Gebze-Kocaeli, Turkey.
authors: Zeynep
authors: Z
authors: Turkmen
authors: Andrey S
authors: AS
authors: Klymchenko
authors: Sule
authors: S
authors: Oncul
authors: Guy
authors: G
authors: Duportail
authors: Gulacti
authors: G
authors: Topcu
authors: Alexander P
authors: AP
authors: Demchenko
mesh_terms: D005419:Flavonoids / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D020404:Glycerophospholipids / Q000737:chemistry; D008051:Lipid Bilayers / Q000737:chemistry*; D021962:Membrane Microdomains / Q000737:chemistry*; D009828:Oleanolic Acid / Q000737:chemistry*; D013050:Spectrometry, Fluorescence / Q000379:methods; D013109:Sphingomyelins / Q000737:chemistry
chemical_list: D005419:Flavonoids; D005456:Fluorescent Dyes; D020404:Glycerophospholipids; D008051:Lipid Bilayers; D013109:Sphingomyelins; D009828:Oleanolic Acid; C041477:3-hydroxyflavone