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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.


Synthesized compounds
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Fig2: Synthesized compounds

Mentions: In search of novel potential photosensitizers we obtained a series of carboxyalkyloxy tetraphenylporphyrin derivatives 4–8 (Fig. 2). Carboxyl groups are attached to one of the phenyl rings of tetraphenylporphyrin via alkyl chains of different lengths. Previously, compounds with n = 1 and n = 3 were obtained as intermediates during the synthesis of more complex tetraphenylporphyrin derivatives. In particular, cholesterol derivatives of carboxymethylporphyrin (n = 1) were synthesized and their gelator properties described [14]. Butyric acid (n = 3) was attached to arylporphyrin via an ether bond in order to obtain a porphyrin with an easily modifiable fragment (in this case a COOH group). Next, it was substituted using either lipophilic guanosine in order to examine the self-assembly of this group [15] or with a tyrosine group when obtaining modified TiO2 clusters in which photoinduced electron transfer occurred [16]. Amide derivatives of this compound were also obtained as potential agents for photodynamic therapy of cancers [17]. Glycosidic porphyrins obtained from the butyric acid derivative of tritolylphenylporphyrin were also designed as potential PDT agents [18].Fig. 2


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)

Synthesized compounds
© Copyright Policy
Related In: Results  -  Collection

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

Fig2: Synthesized compounds
Mentions: In search of novel potential photosensitizers we obtained a series of carboxyalkyloxy tetraphenylporphyrin derivatives 4–8 (Fig. 2). Carboxyl groups are attached to one of the phenyl rings of tetraphenylporphyrin via alkyl chains of different lengths. Previously, compounds with n = 1 and n = 3 were obtained as intermediates during the synthesis of more complex tetraphenylporphyrin derivatives. In particular, cholesterol derivatives of carboxymethylporphyrin (n = 1) were synthesized and their gelator properties described [14]. Butyric acid (n = 3) was attached to arylporphyrin via an ether bond in order to obtain a porphyrin with an easily modifiable fragment (in this case a COOH group). Next, it was substituted using either lipophilic guanosine in order to examine the self-assembly of this group [15] or with a tyrosine group when obtaining modified TiO2 clusters in which photoinduced electron transfer occurred [16]. Amide derivatives of this compound were also obtained as potential agents for photodynamic therapy of cancers [17]. Glycosidic porphyrins obtained from the butyric acid derivative of tritolylphenylporphyrin were also designed as potential PDT agents [18].Fig. 2

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.