A triterpene oleanolic acid conjugate with 3-hydroxyflavone derivative as a new membrane probe with two-color ratiometric response.
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.
Turkmen
Zeynep
Z
TUBITAK Research Institute for Genetic Engineering and Biotechnology, 41470 Gebze-Kocaeli, Turkey.
Klymchenko
Andrey S
AS
Oncul
Sule
S
Duportail
Guy
G
Topcu
Gulacti
G
Demchenko
Alexander P
AP
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
D005419:Flavonoids; D005456:Fluorescent Dyes; D020404:Glycerophospholipids; D008051:Lipid Bilayers; D013109:Sphingomyelins; D009828:Oleanolic Acid; C041477:3-hydroxyflavone