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Fluorescence Studies on New Potential Antitumoral Benzothienopyran-1-ones in Solution and in Liposomes

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Abstract

Fluorescence properties of four new potential antitumoral compounds, 3-arylbenzothieno[2,3-c]pyran-1-ones, were studied in solution and in lipid membranes of dipalmitoyl phosphatidylcholine (DPPC), egg yolk phosphatidylcholine (Egg-PC) and dioctadecyldimethylammonium bromide (DODAB). The 3-(4-methoxyphenyl)benzothieno[2,3-c]pyran-1-one (1c) exhibits the higher fluorescence quantum yields in all solvents studied. All compounds present a solvent sensitive emission, with significant red shifts in polar solvents for the methoxylated compounds. The results point to an ICT character of the excited state, more pronounced for compound 1c. Fluorescence (steady-state) anisotropy measurements of the compounds incorporated in liposomes of DPPC, DODAB and Egg-PC indicate that all compounds have two different locations, one due to a deep penetration in the lipid membrane and another corresponding to a more hydrated environment. In general, the methoxylated compounds prefer hydrated environments inside the liposomes. The 3-(4-fluorophenyl)benzothieno[2,3-c]pyran-1-one (1a) clearly prefers a hydrated environment, with some molecules located at the outer part of the liposome interface. On the contrary, the preferential location of 3-(2-fluorophenyl)benzothieno[2,3-c]pyran-1-one (1b) is in the region of lipid hydrophobic tails. Compounds with a planar geometry (1a and 1c) have higher mobility in the lipid membranes when phase transition occurs.

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Abbreviations

DPPC:

Dipalmitoyl phosphatidylcholine

DODAB:

Dioctadecyldimethylammonium bromide

Egg-PC:

Egg yolk phosphatidylcholine

PC:

Phosphatidylcholine

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Acknowledgements

Foundation for the Science and Technology (FCT)—Portugal and FEDER (Fundo Europeu de Desenvolvimento Regional), for financial support through Centro de Física (CFUM) and Centro de Química (CQ-UM) of University of Minho and through the Project PTDC/QUI/81238/2006. M.S.D. Carvalho and R.C. Calhelha acknowledge FCT for their PhD grants SFRH/BD/47052/2008 and SFRH/BD/29274/2006, respectively.

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Authors and Affiliations

  1. Centro de Física (CFUM), Universidade do Minho, Campus de Gualtar, 4710-057, Braga, Portugal

    Elisabete M. S. Castanheira, M. Solange D. Carvalho, Daniel J. G. Soares & Paulo J. G. Coutinho

  2. Centro de Química (CQ-UM), Universidade do Minho, Campus de Gualtar, 4710-057, Braga, Portugal

    M. Solange D. Carvalho, Ricardo C. Calhelha & Maria-João R. P. Queiroz

Authors
  1. Elisabete M. S. Castanheira
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  2. M. Solange D. Carvalho
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  3. Daniel J. G. Soares
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  4. Paulo J. G. Coutinho
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  5. Ricardo C. Calhelha
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  6. Maria-João R. P. Queiroz
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Correspondence to Elisabete M. S. Castanheira.

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Castanheira, E.M.S., Carvalho, M.S.D., Soares, D.J.G. et al. Fluorescence Studies on New Potential Antitumoral Benzothienopyran-1-ones in Solution and in Liposomes. J Fluoresc 21, 911–922 (2011). https://doi.org/10.1007/s10895-010-0607-3

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  • DOI: https://doi.org/10.1007/s10895-010-0607-3

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