Synthesis, characterization, photochemical properties and cytotoxicity of the novel porphyrazine functionalized with nitroimidazolylbutylsulfanyl groups

Lijewski, Sebastian; Piskorz, Jaroslaw; Kucińska, Małgorzata; Wierzchowski, Marcin; Czerniak, Katarzyna; Billert, Hanna; Murias, Marek; Mielcarek, Jadwiga; Gośliński, Tomasz

doi:10.1016/j.inoche.2013.01.001

Cited by 18 publications

(5 citation statements)

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“…Porphyrazines that contain sulfanyl substituents reveal good solubility in common organic solvents and significant photocytotoxicities . Many years of research on sulfanyl porphyrazines led to the expansion of their periphery with various groups; for example, ether/thioether, calixarene, (tetrathiafulvalene)sulfanylethyl, 2′‐(4‐pyridoxy)ethyl, 1‐naphthylmethyl, 2′‐(ferrocenecarboxy)ethyl, and 4‐(4‐nitroimidazol‐1‐yl)butyl …”

Section: Introductionmentioning

confidence: 99%

“…[6][7][8][9] Many years of research on sulfanyl porphyrazines led to the expansion of their periphery with various groups;f or example, ether/thioether, [10,11] calixarene, [12] (tetrathiafulvalene)sulfanylethyl, [13] 2'-(4-pyridoxy)ethyl, [14] 1-naphthylmethyl, [8] 2'-(ferrocenecarboxy)ethyl, [15] and 4-(4-nitroimidazol-1-yl)butyl. [16] The possibility to add and modify dendrimer substituents at the periphery of macrocyclic rings has been applieds of ar for porphyrins and phthalocyanines. [17,18] It has been shownt hat dendrimericm oieties around the porphyrinoid core significantly affect their photophysical characteristics.…”

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: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2016

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“…Both symmetrically and asymmetrically substituted porphyrazines have been synthesized by using a variety of strategies. ,,,− The synthesis of porphyrazines typically begins with an appropriate dinitrile precursor, which is then either directly cyclized into the porphyrinoid product, or first converted to a more reactive pyrroline intermediate. In our earlier work, we relied upon a general procedure that followed the pyrroline method for the synthesis of the p - tert -butyl-substituted porphyrazine, although we did not report the step-by-step details of this synthesis.…”

Section: Resultsmentioning

confidence: 99%

The Influence of Peripheral Substituent Modification on P^V, Mn^III, and Mn^V(O) Corrolazines: X-ray Crystallography, Electrochemical and Spectroscopic Properties, and HAT and OAT Reactivities

et al. 2016

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The influence of remote peripheral substitution on the physicochemical properties and reactivity of phosphorus and manganese corrolazine (Cz) complexes was examined. The substitution of p-MeO for p-t-Bu groups on the eight phenyl substituents of the β-carbon atoms of the Cz ring led to changes in UV–vis transitions and redox potentials for each of the complexes. The oxygen atom transfer (OAT) and hydrogen atom transfer (HAT) reactivity of the MnV(O) complexes was also influenced by p-MeO substitution. The OAT reactivity of MnV(O)(MeOP8Cz) (MeOP8Cz = octakis-(p-methoxyphenyl)corrolazinato3−) with triarylphosphine (PAr3) substrates led to second-order rate constants from 10.2(5) to 3.1(2) × 104 M−1 s−1. These rates of OAT are slower than those seen for MnV(O)(TBP8Cz) (TBP8Cz = octakis(p-tert-butylphenyl) corrolazinato3−). A Hammett study involving para-substituted PAr3 substrates reveals a Hammett ρ-value for MnV(O)(MeOP8Cz) that is more negative than that observed for MnV(O)(TBP8Cz), consistent with a less electrophilic Mn center. The HAT reactivity of MnV(O)(MeOP8Cz) with C–H substrates was examined and revealed second-order rate constants from 6.8(5) × 10−5 to 1.70(2) × 10−1 M−1 s−1. The rate constants varied with the C–H bond strength of the substrate. Slightly faster HAT rates with C–H substrates were observed with MnV(O)(MeOP8Cz) compared to MnV(O)(TBP8Cz), indicating that the basicity of the putative [MnIV(O)]− intermediate likely compensates for the more negative redox potential in the driving force for HAT. In addition, the complete, large-scale synthesis of the para-phenyl-substituted porphyrazines RP8PzH2 (R = p-tert-butylphenyl (TB), p-methoxyphenyl (MeO), and p-isopropylphenyl) and corrolazines RP8CzH3 (TBP8CzH3 and MeOP8CzH3) is presented. The crystal structures of the monoprotonated, metal-free corrolazine [(TBP8CzH3)(H)]+[BArF]−, PV(OMe)2-(MeOP8Cz), and MnIII(MeOP8Cz)(MeOH) are presented. This work provides the first insights into the influence of electronic substituent effects on the corrolazine periphery.

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“…On the other hand, it is important to stress that commercially available simple silylamines, such as N , O ‐bis(trimethylsilyl)acetamide (BSA) and 1,1,1,3,3,3‐hexamethyldisilazane (HMDS), are still the most useful in both organic and inorganic chemistry . In particular, HMDS seems to be a very interesting compound that has recently also been used in the preparation of phthalocyanines and porphyrazines, which are very important molecules from a biological point of view …”

Section: Silicon–nitrogen Bond Formationmentioning

confidence: 99%

Catalytic Formation of Silicon–Heteroatom (N, P, O, S) Bonds

Kuciński

Hreczycho

2017

ChemCatChem

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Silicon and its compounds with other heteroatoms have received considerable attention, particularly because of their applicative ability. Silicon forms a large number of compounds with other p‐block elements (e.g., C, N, S, O, F, Cl, and others). All of them affect practical chemistry to some extent and are characterized by unique properties. This article highlights recent developments and covers the literature from the last 10 years. It is mainly focused on catalytic methods for silicon–nitrogen, silicon–phosphorus, silicon–oxygen, and silicon–sulfur bond formation. The scope and applications of these practical compounds will also be discussed.

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Synthesis, characterization, photochemical properties and cytotoxicity of the novel porphyrazine functionalized with nitroimidazolylbutylsulfanyl groups

Cited by 18 publications

References 43 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

The Influence of Peripheral Substituent Modification on P^V, Mn^III, and Mn^V(O) Corrolazines: X-ray Crystallography, Electrochemical and Spectroscopic Properties, and HAT and OAT Reactivities

Catalytic Formation of Silicon–Heteroatom (N, P, O, S) Bonds

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Synthesis, characterization, photochemical properties and cytotoxicity of the novel porphyrazine functionalized with nitroimidazolylbutylsulfanyl groups

Cited by 18 publications

References 43 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

The Influence of Peripheral Substituent Modification on PV, MnIII, and MnV(O) Corrolazines: X-ray Crystallography, Electrochemical and Spectroscopic Properties, and HAT and OAT Reactivities

Catalytic Formation of Silicon–Heteroatom (N, P, O, S) Bonds

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The Influence of Peripheral Substituent Modification on P^V, Mn^III, and Mn^V(O) Corrolazines: X-ray Crystallography, Electrochemical and Spectroscopic Properties, and HAT and OAT Reactivities