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

Paper ID Volume ID Publish Year Pages File Format Full-Text
27409 44020 2013 10 PDF Available
Title
Spectroscopic and photodynamic properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different media
Abstract

•Photodynamic activity of cationic and non-charged porphyrins was compared in different media.•Porphyrin interactions were determined in β-cyclodextrin and AOT reverse micelles.•Anthracene derivatives were used as molecule trap of singlet molecular oxygen.•Efficient photosensitized oxidation of tryptophan was found using non-charged porphyrin.•Porphyrin substituted by aliphatic amine groups represents an interesting agent to photoinactivate microbes.

The spectroscopic properties and the photodynamic activity of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)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 (β-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.

Graphical abstractThe spectroscopic properties and the photodynamic activity of porphyrins substituted by aminopropoxy groups were investigated in homogeneous media and in microheterogeneous systems.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Porphyrin; Photosensitizer; Singlet oxygen; Micelles; Cyclodextrin
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Spectroscopic and photodynamic properties of 5,10,15,20-tetrakis[4-(3-N,N-dimethylaminopropoxy)phenyl]porphyrin and its tetracationic derivative in different media
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 270, 15 October 2013, Pages 75–84
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us