Photophysical properties and photochemistry of a sulfanyl porphyrazine bearing isophthaloxybutyl substituents

Lijewski, Sebastian; Gierszewski, Mateusz; Sobotta, Łukasz; Piskorz, Jaroslaw; Kordas, Paulina; Kucińska, Małgorzata; Baranowski, Daniel; Gdaniec, Zofia; Murias, Marek; Karolczak, Jerzy; Sikorski, Marek; Mielcarek, Jadwiga; Gośliński, Tomasz

doi:10.1016/j.dyepig.2014.10.004

Cited by 21 publications

(23 citation statements)

References 39 publications

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“…For octakis‐substituted Pzs 4 and 8 , the singlet‐oxygen‐generation efficacy was relatively low ( Φ Δ =0.03 for 4 and Φ Δ =0.02 for 8 ). No increase in singlet‐oxygen‐generation efficacy was observed by enlargement of our recently published G 0 symmetrical porphyrazine to 8 , as both revealed low singlet‐oxygen‐generation efficacies with yields of 0.02 in DMF. The photochemical data obtained for Pzs 4 and 8 comply with those previously published for sulfanyl Pzs …”

Section: Resultsmentioning

confidence: 73%

“…2,3‐Bis[4‐(3,5‐dimethoxycarbonylphenoxy)butylsulfanyl]maleonitrile ( 10 ) was synthesized according to previously published procedures . Briefly, the alkylation reaction of dimercaptomaleonitrile disodium salt with dimethyl 5‐(4‐bromobutoxy)isophthalate led to 10 .…”

Section: Resultsmentioning

confidence: 99%

“…Herein, we report the synthesis of a series of dendrimer‐substituted sulfanyl porphyrazines. They were obtained as a part of our research on sulfanyl porphyrazines that bear isophthaloxybutyl substituents on their periphery . The novel compounds were characterized in terms of their photophysical properties.…”

Section: Introductionmentioning

confidence: 99%

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Dendrimeric Sulfanyl Porphyrazines: Synthesis, Physico‐Chemical Characterization, and Biological Activity for Potential Applications in Photodynamic Therapy

et al. 2016

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Sulfanyl porphyrazines substituted at their periphery with different dendrimeric moieties up to their first generation were synthesized and characterized by photochemical and biological methods. The presence of a dendrimeric periphery enhanced the spectral properties of the porphyrazines studied. The singlet‐oxygen‐generation quantum yield of the obtained macrocycles ranged from 0.02 to 0.20 and was strongly dependent on the symmetry of the compounds and the terminal groups of the dendritic outer shell. The in vitro biological effects of three most promising tribenzoporphyrazines were examined; the results indicated their potential as photosensitizers for photodynamic therapy (PDT) against two oral squamous cell carcinoma cell lines derived from the tongue. The highest photocytotoxicity was found for sulfanyl tribenzoporphyrazine that possessed 4‐[3,5‐di(hydroxymethyl)phenoxy]butyl substituents with nanomolar IC50 values at 10 and 42 nm against CAL 27 and HSC‐3 cell lines, respectively.

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Section: Resultsmentioning

confidence: 73%

Section: Resultsmentioning

confidence: 99%

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Dendrimeric Sulfanyl Porphyrazines: Synthesis, Physico‐Chemical Characterization, and Biological Activity for Potential Applications in Photodynamic Therapy

et al. 2016

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“…Sulfanyl magnesium(II) porphyrazine with isophthaloxybutyl substituents 1 was obtained according to the recently published procedure [28]. The demetallation of 1 through the removal of the magnesium ion with trifluoroacetic acid gave the free base porphyrazine 2 in 63% yield (Scheme 1) [3].…”

Section: Synthesismentioning

confidence: 99%

“…Lately, we elaborated the novel magnesium(II) porphyrazine, possessing isophthaloxybutylsulfanyl substituents, and investigated its photophysical and photochemical properties [28]. In this work, we extended our studies to researching the electrochemical properties of the novel Pz macrocycle and its derivatives.…”

Section: Introductionmentioning

confidence: 98%

Electrochemical properties of metallated porphyrazines possessing isophthaloxybutylsulfanyl substituents: Application in the electrocatalytic oxidation of hydrazine

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et al. 2015

Electrochimica Acta

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Improved electrocatalytic response toward hydrogen peroxide reduction of sulfanyl porphyrazine/multiwalled carbon nanotube hybrids deposited on glassy carbon electrodes

et al. 2016

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Photophysical properties and photochemistry of a sulfanyl porphyrazine bearing isophthaloxybutyl substituents

Cited by 21 publications

References 39 publications

Dendrimeric Sulfanyl Porphyrazines: Synthesis, Physico‐Chemical Characterization, and Biological Activity for Potential Applications in Photodynamic Therapy

Dendrimeric Sulfanyl Porphyrazines: Synthesis, Physico‐Chemical Characterization, and Biological Activity for Potential Applications in Photodynamic Therapy

Electrochemical properties of metallated porphyrazines possessing isophthaloxybutylsulfanyl substituents: Application in the electrocatalytic oxidation of hydrazine

Improved electrocatalytic response toward hydrogen peroxide reduction of sulfanyl porphyrazine/multiwalled carbon nanotube hybrids deposited on glassy carbon electrodes

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