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Investigation of Zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) Porphyrazine for Application as Photosensitizer in Photodynamic Therapy of Cancer.

Sakamoto K, Ohno-Okumura E, Kato T, Watanabe M, Cook MJ - Met Based Drugs (2008)

Bottom Line: Zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine reacted with dimethyl sulfate and monochloroacetic acid to produce their quaternized products and diethyl sulfate to produce the sulfo-substituted products.All quaternized and sulfo-substituted showed amphiphilic character.Identical peaks in cyclic voltammograms appeared for these products before and after quaternization.

View Article: PubMed Central - PubMed

Affiliation: Department of Applied Molecular Chemistry, College of Industrial Technology, Nihon University, 1-2-1 Izumi-cho, Narashino-shi, Chiba-ken 275-8575, Japan.

ABSTRACT
The phthalocyanine analogue containing nonperipheral long alkyl-substituted benzenoid rings and pyridine rings, zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine, was synthesized. Zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine reacted with dimethyl sulfate and monochloroacetic acid to produce their quaternized products and diethyl sulfate to produce the sulfo-substituted products. All quaternized and sulfo-substituted showed amphiphilic character. Identical peaks in cyclic voltammograms appeared for these products before and after quaternization. During the evaluation of zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine for its photodynamic therapy of cancer (PDT) efficacy by cancer cell culture, the light exposed dimethyl sulfate quaternized zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazines in IU-002 cells produce cell disruption that can be detected as a decrease in fluorescence.

No MeSH data available.


Related in: MedlinePlus

Synthetic pathway of zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine.
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Related In: Results  -  Collection


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fig1: Synthetic pathway of zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine.

Mentions: The synthetic procedure used to prepare thenovel nonperipheral-substituted phthalocyanine derivative, zincbis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine, was the same as that usedfor the preparation of zinc bis(1,4-didecylbenzo)-bis(3,4-pyrido) porphyrazine[9–12]. Zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine was synthesized in 80% yieldusing equimolar amounts of 3,6-didecylphthalodinitrile and 2,3-pyridinecarbonitrile in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as basic catalyst (see Figure 1). The targetcompound, zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine, and itsintermediates were studied using Fourier transformation infrared (IR), protonnuclear magnetic resonance (1H-NMR), ultraviolet-visible(UV-Vis) spectroscopy, and elemental analysis. The analytical data of the compound werein good agreement with the proposed structure.


Investigation of Zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) Porphyrazine for Application as Photosensitizer in Photodynamic Therapy of Cancer.

Sakamoto K, Ohno-Okumura E, Kato T, Watanabe M, Cook MJ - Met Based Drugs (2008)

Synthetic pathway of zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine.
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC2266814&req=5

fig1: Synthetic pathway of zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine.
Mentions: The synthetic procedure used to prepare thenovel nonperipheral-substituted phthalocyanine derivative, zincbis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine, was the same as that usedfor the preparation of zinc bis(1,4-didecylbenzo)-bis(3,4-pyrido) porphyrazine[9–12]. Zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine was synthesized in 80% yieldusing equimolar amounts of 3,6-didecylphthalodinitrile and 2,3-pyridinecarbonitrile in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as basic catalyst (see Figure 1). The targetcompound, zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine, and itsintermediates were studied using Fourier transformation infrared (IR), protonnuclear magnetic resonance (1H-NMR), ultraviolet-visible(UV-Vis) spectroscopy, and elemental analysis. The analytical data of the compound werein good agreement with the proposed structure.

Bottom Line: Zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine reacted with dimethyl sulfate and monochloroacetic acid to produce their quaternized products and diethyl sulfate to produce the sulfo-substituted products.All quaternized and sulfo-substituted showed amphiphilic character.Identical peaks in cyclic voltammograms appeared for these products before and after quaternization.

View Article: PubMed Central - PubMed

Affiliation: Department of Applied Molecular Chemistry, College of Industrial Technology, Nihon University, 1-2-1 Izumi-cho, Narashino-shi, Chiba-ken 275-8575, Japan.

ABSTRACT
The phthalocyanine analogue containing nonperipheral long alkyl-substituted benzenoid rings and pyridine rings, zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine, was synthesized. Zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine reacted with dimethyl sulfate and monochloroacetic acid to produce their quaternized products and diethyl sulfate to produce the sulfo-substituted products. All quaternized and sulfo-substituted showed amphiphilic character. Identical peaks in cyclic voltammograms appeared for these products before and after quaternization. During the evaluation of zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazine for its photodynamic therapy of cancer (PDT) efficacy by cancer cell culture, the light exposed dimethyl sulfate quaternized zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazines in IU-002 cells produce cell disruption that can be detected as a decrease in fluorescence.

No MeSH data available.


Related in: MedlinePlus