Metal template assembly of highly functionalized octacyanoporphyrazine framework from TCNE structural units

Klapshina, Larisa G.; Grigoryev, Ilya S.; Douglas, William E.; Gudilenkov, Ivan D.; Семенов, В. В.; Bushuk, B. A.; Бушук, С. Б.

doi:10.1039/b701994g

Cited by 18 publications

(11 citation statements)

References 19 publications

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“…Two tetracyanotetra(aryl)porphyrazine dyes were tested with 4-biphenyl ( pz II ) and 4-diethylaminophenyl ( pz IV ) groups in the periphery of the porphyrazine macrocycle. For the synthesis of pz II and pz IV , we used a synthetic approach using a metal template assembly of the porphyrazine frameworks that we developed and described in detail previously [ 20 , 21 , 26 ]. The chemical structure of the dyes is shown in Figure 1 .…”

Section: Resultsmentioning

confidence: 99%

Cyanoarylporphyrazines with High Viscosity Sensitivity: A Step towards Dosimetry-Assisted Photodynamic Cancer Treatment

et al. 2021

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Despite the significant relevance of photodynamic therapy (PDT) as an efficient strategy for primary and adjuvant anticancer treatment, several challenges compromise its efficiency. In order to develop an “ideal photosensitizer” and the requirements applied to photosensitizers for PDT, there is still a need for new photodynamic agents with improved photophysical and photobiological properties. In this study, we performed a detailed characterization of two tetracyanotetra(aryl)porphyrazine dyes with 4-biphenyl (pz II) and 4-diethylaminophenyl (pz IV) groups in the periphery of the porphyrazine macrocycle. Photophysical properties, namely, fluorescence quantum yield and lifetime of both photosensitizers, demonstrate extremely high dependence on the viscosity of the environment, which enables them to be used as viscosity sensors. PzII and pz IV easily enter cancer cells and efficiently induce cell death under light irradiation. Using fluorescence lifetime imaging microscopy, we demonstrated the possibility of assessing local intracellular viscosity and visualizing viscosity changes driven by PDT treatment with the compounds. Thus, pz II and pz IV combine the features of potent photodynamic agents and viscosity sensors. These data suggest that the unique properties of the compounds provide a tool for PDT dosimetry and tailoring the PDT treatment regimen to the individual characteristics of each patient.

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Section: Resultsmentioning

confidence: 99%

Cyanoarylporphyrazines with High Viscosity Sensitivity: A Step towards Dosimetry-Assisted Photodynamic Cancer Treatment

et al. 2021

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“…Yb[pz(4‐FC 6 H 4 ) 4 (CN) 4 ](OH)·3H 2 O was prepared using the original synthetic approach reported recently . The starting compound 2‐(4‐fluorophenyl)‐1,1,2‐tricyanoethylene was synthesized according to the literature method …”

Section: Methodsmentioning

confidence: 99%

Novel regular polyimide-graft -(polymethacrylic acid) brushes: Synthesis and possible applications as nanocontainers of cyanoporphyrazine agents for photodynamic therapy

Yakimansky

Мелешко

Ilgach

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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International audienceAn approach to the synthesis of new regular graft-copolymers polyimide (PI)-graft-polymethacrylic acid is elaborated, including (1) synthesis of multicenter PI macroinitiators, (2) controlled ATRP of tert-butylmethacrylate on the prepared macroinitiators, and (3) protonolysis of tert-butyl ester groups of side chains of the resulting PI-graft-poly(tert-butylmethacrylate). Experimental conditions for attaining complete conversions of the first and the third stages of the process are determined by means of 1H NMR and FTIR-spectroscopy. Polymer products of the first and the second stages of the process, as well as poly(tert-butylmethacrylate) side chains cleaved from the PI-graft-poly(tert-butylmethacrylate) copolymers by complete decomposition of the PI backbone under alkaline hydrolysis conditions, are characterized by GPC. The kinetics of poly(tert-butylmethacrylate) chain growth on a PI macroinitiator under ATRP conditions are studied. The results obtained provide evidence for the controlled character of the ATRP process and the regular structure of the synthesized graft-copolymers. It is shown that PI-g-PMAA PI brushes are significantly more efficient intracellular delivery agents for the potential photosensitizer [tetra(4-fluorophenyl)tetracyanoporhyrazine free base] than are the commonly used PEG-micelles

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“…I$C 6 H 6 $3H 2 O and II$4CH 3 C 6 H 5 $3THF were synthesized according to previously published procedures. 3 The UV/Vis spectra were recorded on a Perkin-Elmer Lambda 25 spectrophotometer. Infrared spectra were taken on an FSM 1201 FT spectrophotometer by using Nujol mulls on NaCl plates or as KBr pellets.…”

Section: Methodsmentioning

confidence: 99%

“…Recently, we reported a novel facile synthetic route for the metal template assembly of a tetrapyrrollic framework from TCNE structural units by the reaction of TCNE with p-sandwich metal complexes. 3 This approach provided the first preparation of metalloporphyrazine dyes bearing eight peripheral strongly electron-withdrawing CN substituents (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Novel metal-template assembled highly-functionalized cyanoporphyrazine ytterbium and vanadium complexes for potential photonic and optoelectronic applications

et al. 2009

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Metal template assembly of highly functionalized octacyanoporphyrazine framework from TCNE structural units

Abstract: A new route to the octacyanoporphyrazine framework based on the interaction of metal sandwich pi-complexes with TCNE has been developed.

Cited by 18 publications

References 19 publications

Cyanoarylporphyrazines with High Viscosity Sensitivity: A Step towards Dosimetry-Assisted Photodynamic Cancer Treatment

Cyanoarylporphyrazines with High Viscosity Sensitivity: A Step towards Dosimetry-Assisted Photodynamic Cancer Treatment

Novel regular polyimide-graft -(polymethacrylic acid) brushes: Synthesis and possible applications as nanocontainers of cyanoporphyrazine agents for photodynamic therapy

Novel metal-template assembled highly-functionalized cyanoporphyrazine ytterbium and vanadium complexes for potential photonic and optoelectronic applications

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