Author(s):
Queiroz, Maria João R. P. 
; Peixoto, Daniela ; Rodrigues, Ana Rita O. ; Mendes, Pedro M. F. ; Costa, Cátia N. C. ; Coutinho, Paulo J. G. ; Castanheira, Elisabete M. S.
Date: 2013
Persistent ID: http://hdl.handle.net/1822/23329
Origin: RepositóriUM - Universidade do Minho
Subject(s): 1,3-Diarylureas; Thieno[3,2-b]pyridines; Fluorescence; Lipid membranes; Fluorescence probes
Description
New six fluorescent 1,3-diarylureas linked by C-C Suzuki coupling to the 6-position of the methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate moiety were prepared by reaction of the amino groups on the ortho or meta positions relative to the C-C bond of the Suzuki coupling products, with different para-substituted arylisocyanates (H, OMe, CN), in high to excellent yields. The fluorescence properties of the 1,3-diarylureas in solution and in lipid membranes of egg-yolk phosphatidylcholine (Egg-PC), dipalmitoyl phosphatidylcholine (DPPC), dipalmitoyl phosphatidylglycerol (DPPG) or dioctadecyldimethylammonium bromide (DODAB), with or without cholesterol (Ch), were studied. The six 1,3-diarylureas have reasonable fluorescence quantum yields in several solvents (between 0.02 and 0.69) and present a moderately solvent sensitive emission, but are not fluorescent in alcohols and water. The compounds bearing the arylurea moiety in the meta position relative to the C-C bond, especially with the OMe and CN substituents, present the better solvatochromic properties.
Incorporation of the six compounds in lipid membranes indicates that all the compounds are deeply located in the hydrophobic region of the lipid bilayers, feeling the transition between the rigid gel phase and fluid phases.
