Fluorescence studies on potential antitumoral heteroaryl and heteroannulated in...

• Author(s): Castanheira, Elisabete M. S. ; Abreu, Ana S. ; Carvalho, M. Solange D. ; Queiroz, Maria João R. P. ; Ferreira, Paula M. T.
• Date: 2009
• Persistent ID: http://hdl.handle.net/1822/9916
• Origin: RepositóriUM - Universidade do Minho
• Subject(s): Heteroaryl and heteroannulated indoles; Lipid membranes; Fluorescence anisotropy
• Document Type: Article
• Language: English

Description

Fluorescence properties of three potential antitumoral compounds, a 3-(dibenzothien-4-yl)indole 1, a phenylbenzothienoindole 2 and a 3-(dibenzofur-4-yl)indole 3, were studied in solution and in lipid aggregates of dipalmitoyl phosphatidylcholine (DPPC), dioleoyl phosphatidylethanolamine (DOPE) and egg yolk phosphatidylcholine (Egg-PC). The 3-(dibenzofur-4-yl)indole 3 exhibits the higher fluorescence quantum yields in all solvents studied (0.32 ≤ ΦF ≤ 0.51). All the compounds present a solvent sensitive emission, with significant red shifts in alcohols. The results point to an ICT character of the excited state, more pronounced for compound 1. Fluorescence (steady-state) anisotropy measurements of the compounds incorporated in lipid aggregates of DPPC, DOPE and Egg-PC indicate that the three compounds are deeply located in the lipid bilayer, feeling the difference between the rigid gel phase and fluid phases.