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The synthesis of new potential photosensitizers. 1. Mono-carboxylic acid derivatives of tetraphenylporphyrin.

Zięba G, Rojkiewicz M, Kozik V, Jarzembek K, Jarczyk A, Sochanik A, Kuś P - Monatsh. Chem. (2011)

Bottom Line: A series of mono-alkylcarboxylic acid derivatives of tetraphenylporphyrin have been prepared.Experimental log P were determined by use of reversed-phase thin-layer chromatography with use of log P Rekker.These porphyrins are potential photosensitizers in photodynamic therapy. .

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Silesia, 9, Szkolna Street, 40-006 Katowice, Poland.

ABSTRACT

Abstract: A series of mono-alkylcarboxylic acid derivatives of tetraphenylporphyrin have been prepared. All the porphyrins were completely characterized by use of mass, (1)H NMR, UV-visible, and fluorescence spectroscopy. Experimental log P were determined by use of reversed-phase thin-layer chromatography with use of log P Rekker. These porphyrins are potential photosensitizers in photodynamic therapy.

Graphical abstract: .

No MeSH data available.


Hematoporphyrin and tetraphenylporphyrin
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Fig1: Hematoporphyrin and tetraphenylporphyrin

Mentions: Hematoporphyrin (1), the first compound that was tried in photodynamic therapy (PDT), contains, besides the basic porphyrin ring, two carboxyethylene groups. Photofrin, currently the most frequently used porphyrin-type compound in anticancer therapy, was obtained from hematoporphyrin (1) (Fig. 1) [1]. Photofrin molecules contain carboxyl (carboxyethylene) groups which give the compound its hydrophobic and hydrophilic properties. Photofrin preparations are, however, a mixture of several porphyrin compounds. Numerous research teams around the world have been trying to obtain novel compounds with precisely determined structure and controlled biological properties [2–4]. Several of these compounds are derivatives of tetraphenylporphyrin (2) (tetraarylporphyrin, Fig. 1). The aryl fragments in these porphyrins are modified by substituting hydrogen atoms with various groups altering the hydrophobic–hydrophilic character of the whole molecule, most often without changing its photochemical properties.Fig. 1


The synthesis of new potential photosensitizers. 1. Mono-carboxylic acid derivatives of tetraphenylporphyrin.

Zięba G, Rojkiewicz M, Kozik V, Jarzembek K, Jarczyk A, Sochanik A, Kuś P - Monatsh. Chem. (2011)

Hematoporphyrin and tetraphenylporphyrin
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4494763&req=5

Fig1: Hematoporphyrin and tetraphenylporphyrin
Mentions: Hematoporphyrin (1), the first compound that was tried in photodynamic therapy (PDT), contains, besides the basic porphyrin ring, two carboxyethylene groups. Photofrin, currently the most frequently used porphyrin-type compound in anticancer therapy, was obtained from hematoporphyrin (1) (Fig. 1) [1]. Photofrin molecules contain carboxyl (carboxyethylene) groups which give the compound its hydrophobic and hydrophilic properties. Photofrin preparations are, however, a mixture of several porphyrin compounds. Numerous research teams around the world have been trying to obtain novel compounds with precisely determined structure and controlled biological properties [2–4]. Several of these compounds are derivatives of tetraphenylporphyrin (2) (tetraarylporphyrin, Fig. 1). The aryl fragments in these porphyrins are modified by substituting hydrogen atoms with various groups altering the hydrophobic–hydrophilic character of the whole molecule, most often without changing its photochemical properties.Fig. 1

Bottom Line: A series of mono-alkylcarboxylic acid derivatives of tetraphenylporphyrin have been prepared.Experimental log P were determined by use of reversed-phase thin-layer chromatography with use of log P Rekker.These porphyrins are potential photosensitizers in photodynamic therapy. .

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Silesia, 9, Szkolna Street, 40-006 Katowice, Poland.

ABSTRACT

Abstract: A series of mono-alkylcarboxylic acid derivatives of tetraphenylporphyrin have been prepared. All the porphyrins were completely characterized by use of mass, (1)H NMR, UV-visible, and fluorescence spectroscopy. Experimental log P were determined by use of reversed-phase thin-layer chromatography with use of log P Rekker. These porphyrins are potential photosensitizers in photodynamic therapy.

Graphical abstract: .

No MeSH data available.