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

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 e...

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Bibliographic Details
Main Author: Castanheira, Elisabete M. S. (author)
Other Authors: Abreu, Ana S. (author), Carvalho, M. Solange D. (author), Queiroz, Maria João R. P. (author), Ferreira, Paula M. T. (author)
Format: article
Language:eng
Published: 2009
Subjects:
Online Access:http://hdl.handle.net/1822/9916
Country:Portugal
Oai:oai:repositorium.sdum.uminho.pt:1822/9916
Description
Summary: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.