Spectroscopic and photodynamic properties of 5,10,15, 20-tetrakis[4-(3-n,n- dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different media

  • Mora S
  • Milanesio M
  • Durantini E
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Abstract

The spectroscopic properties and the photodynamic activity of 5,10,15,20-tetrakis[4-(3-N,Ndimethylaminopropoxy) phenyl]porphyrin (TAPP) and its tetracationic derivative (TAPP4+) were studied in homogeneous media and in microheterogeneous systems. The results were compared with those of 5,10,15,20-tetra(4-N,N,N-trimethylammoniumphenyl)porphyrin (TMAP4+), which represents an active tetracationic photosensitizer. Absorption and fluorescence studies indicated that the tetrapyrrolic macrocycle retains its individual spectroscopic properties. Interaction with β-cyclodextrin (-CD) was found for TAPP4+by fluorescence emission. Also, these porphyrins interact with n-heptane/sodium bis(2-ethylhexyl)sulfosuccinate (AOT)/water reverse micelles. Photosensitization ability was evaluated using 9,10-dimethylanthracene in N,N-dimethylformamide and AOT micelles, while tetrasodium 2,2'-(anthracene-9,10-diyl)bis(methylmalonate) was used in aqueous solutions. Also, photosensitized decomposition of l-tryptophan was investigated in these media. In particular, Trp was fast photooxidized by TAPP in a biomimetic media formed by AOT reverse micelles. Therefore, this intrinsically non-charged porphyrin represents an interesting photosensitizer for the photodynamic inactivation of microorganisms. © 2013 Elsevier B.V.

Author-supplied keywords

  • Cyclodextrin
  • Micelles
  • Photosensitizer
  • Porphyrin
  • Singlet oxygen

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Authors

  • Edgardo N. DurantiniNational Council of Scientific and Technical Research of Argentina (CONICET)

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  • S. Jimena Mora

  • M. Elisa Milanesio

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