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J Fluoresc. 2009 May;19(3):501-9. doi: 10.1007/s10895-008-0439-6. Epub 2008 Nov 29.

Fluorescence studies on potential antitumoral heteroaryl and heteroannulated indoles in solution and in lipid membranes.

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  • 1Centro de FĂ­sica, Universidade do Minho, Campus de Gualtar, 4710-057, Braga, Portugal. ecoutinho@fisica.uminho.pt

Abstract

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 <or= Phi(F) <or= 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.

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