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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

Typical structures ofquaternized zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazines.
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fig2: Typical structures ofquaternized zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazines.

Mentions: Zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido)porphyrazine (0.17 g, 0.15 mmol) reacted with MCAA (0.57 g, 6 mmol), DES (0.1 g, 0.6 mmol) and DMS (0.2 g, 1.5 mmol), respectively, in N,N-dimetylformamide (DMF) 140°C for 2 hours (see Figures 2 and 3). The reaction mixture was dissolved in acetone (20 cm3), cooledto room temperature, and the resulting solution was filtered. The solvent wasremoved and the product was purified by TLC (eluent : THF-toluene, 8 : 2); theproduct was recovered from the TLC plate via dissolution in pyridine followedby filtration and solvent removal.MCAA:Yield 25%, 1H NMR (δ 400 MHz, C6H6-d6/ppm) 0.87(m, 12H, CH3), 1.13–1.70(m, 56H, γ-CH2), 1.82–2.61(m, 8H, β-CH2), 4.11–4.38(m, 4H, α-CH2), 6.20(s, 2H, CH2),7.14–7.27(m, 4H, Arom), 8.73–.16(m, 6H, Py): IR(ν KBr/cm−1) 3480(νO–H), 3050, 2970(νC–H), 1740(νC=O), 1600, 1500, 1400(νC=C), 1210, 1100, 940, 790,690(δC–H); DES yield 21%,(δ 400 MHz, C6H6-d6/ppm) 0.86(m, 12H, CH3), 1.02–1.63(m, 56H, γ-CH2), 1.88–2.61(m, 8H, β-CH2), 4.26–4.50(m, 4H, α-CH2), 7.37(m, 4H, Arom),8.22(m, 4H, Py): IR(ν KBr/cm−1)3480(νO–H), 3050, 2960(νC–H), 1600, 1460, 1400(νC=C), 1350, 1150(νS=O), 1250, 920, 770(δC–H), 580(δC−S); DMS yield 25%, (δ 400 MHz, C6H6-d6/ppm) 0.90(m, 12H,CH3), 0.95–1.45(m, 56H, γ-CH2), 1.60–2.41(m, 8H, β-CH2), 4.05(s, 6H, CH3), 4.25–4.42(m, 4H, α-CH2), 7.45(m, 4H, Arom),8.02(m, 6H, Py): IR(ν KBr/cm−1)3070, 2980(νC–H), 1500, 1400(νC=C), 1250, 1100, 950, 810,660(δC–H).


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)

Typical structures ofquaternized zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazines.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig2: Typical structures ofquaternized zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido) porphyrazines.
Mentions: Zinc bis(1,4-didecylbenzo)-bis(2,3-pyrido)porphyrazine (0.17 g, 0.15 mmol) reacted with MCAA (0.57 g, 6 mmol), DES (0.1 g, 0.6 mmol) and DMS (0.2 g, 1.5 mmol), respectively, in N,N-dimetylformamide (DMF) 140°C for 2 hours (see Figures 2 and 3). The reaction mixture was dissolved in acetone (20 cm3), cooledto room temperature, and the resulting solution was filtered. The solvent wasremoved and the product was purified by TLC (eluent : THF-toluene, 8 : 2); theproduct was recovered from the TLC plate via dissolution in pyridine followedby filtration and solvent removal.MCAA:Yield 25%, 1H NMR (δ 400 MHz, C6H6-d6/ppm) 0.87(m, 12H, CH3), 1.13–1.70(m, 56H, γ-CH2), 1.82–2.61(m, 8H, β-CH2), 4.11–4.38(m, 4H, α-CH2), 6.20(s, 2H, CH2),7.14–7.27(m, 4H, Arom), 8.73–.16(m, 6H, Py): IR(ν KBr/cm−1) 3480(νO–H), 3050, 2970(νC–H), 1740(νC=O), 1600, 1500, 1400(νC=C), 1210, 1100, 940, 790,690(δC–H); DES yield 21%,(δ 400 MHz, C6H6-d6/ppm) 0.86(m, 12H, CH3), 1.02–1.63(m, 56H, γ-CH2), 1.88–2.61(m, 8H, β-CH2), 4.26–4.50(m, 4H, α-CH2), 7.37(m, 4H, Arom),8.22(m, 4H, Py): IR(ν KBr/cm−1)3480(νO–H), 3050, 2960(νC–H), 1600, 1460, 1400(νC=C), 1350, 1150(νS=O), 1250, 920, 770(δC–H), 580(δC−S); DMS yield 25%, (δ 400 MHz, C6H6-d6/ppm) 0.90(m, 12H,CH3), 0.95–1.45(m, 56H, γ-CH2), 1.60–2.41(m, 8H, β-CH2), 4.05(s, 6H, CH3), 4.25–4.42(m, 4H, α-CH2), 7.45(m, 4H, Arom),8.02(m, 6H, Py): IR(ν KBr/cm−1)3070, 2980(νC–H), 1500, 1400(νC=C), 1250, 1100, 950, 810,660(δC–H).

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