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Journal ArticleDOI: 10.1039/D0DT04351F

Investigation of the biological and photophysicochemical properties of new non-peripheral fluorinated phthalocyanines

02 Mar 2021-Dalton Transactions (The Royal Society of Chemistry)-Vol. 50, Iss: 8, pp 2736-2745
Abstract: This study presents the synthesis of a series of new tetra-substituted phthalocyanines bearing 3,5-bis(trifluoromethyl)phenoxy groups at non-peripheral positions. The resulting macromolecules were characterized by performing different spectroscopic methods including 1H NMR, UV-Vis, FT-IR, and mass spectroscopy. In this study, the synergistic effect of phthalocyanines used as colorants in ink formulas with other chemicals available was probed for the first time. The synergistic effect of methyl laurate on the biological and antioxidant activities of the compounds (2–5) was investigated. Moreover, the therapeutic properties of the complexes (3, 6, and 7) were investigated using photochemical methods. Upon comparison, complex 7 (ΦΔ = 0.42) was found to be more effective than complex 6 (ΦΔ = 0.40) and complex 3 (ΦΔ = 0.27) in terms of producing singlet oxygen. The results confirmed that the heavy atom effect improves the therapeutic effects.

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6 results found

Journal ArticleDOI: 10.1039/D1DT00991E
Abstract: In this study, a new fluorinated phthalonitrile compound namely 5-bis[4-(trifluoromethoxy)-thiophenyl] phthalonitrile was synthesized. In addition, peripherally substituted symmetric metallated phthalocyanine derivatives [M = Co (2) and M = Zn (3)] and unsymmetrically substituted zinc phthalocyanine (ZnPc) complex (4) were synthesized by cyclotetramerization of this phthalonitrile compound. Characterization of all new compounds was carried out using FT-IR, NMR, UV-Vis, and mass spectroscopy. Additionally, antioxidant activity, DNA cleavage activity, antimicrobial activity, biofilm inhibition activity, and bacterial viability inhibition test of the compounds (1–4) were investigated. The antioxidant activities of the new phthalocyanine complexes were studied by performing two different methods. The results indicated that the highest DPPH (1,1-diphenyl-2-picrylhydrazyl) free radical scavenging activity was determined to be 67.85% for 2 and also 3 showed the highest activity with 31.65% for chelating activity at 200 mg L−1 concentration. Phthalocyanine compounds demonstrated effective DNA cleavage and antimicrobial activities. The highest percentage of cell vitality inhibition was found for compound 4, 56.92%. Also, test compounds exhibited good biofilm inhibition activity.

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Topics: Phthalonitrile (64%), Phthalocyanine (56%), Chelating Activity (51%)

4 Citations

Journal ArticleDOI: 10.1016/J.POLY.2021.115479
Ayk Beduoğlu1, Özlem Budak2, Altuğ Mert Sevim1, Atıf Koca2  +1 moreInstitutions (2)
15 Nov 2021-Polyhedron
Abstract: In this study, the synthesis, spectral characterization, electrochemistry, spectroelectrochemistry and electrochromism of a novel double-decker lutetium phthalocyanine, bis-[2(3),9(10),16(17),23(24)-tetrakis-[2-(4-phenyl-2-thiazolyl)sulfanyl] phthalocyaninatolutetium(III), denoted as LuPc2, is reported. The LuPc2 synthesized in this study is unique, being the first thiazole-containing double-decker lutetium phthalocyanine complex published to date. The electrochemistry of LuPc2 was used to support the proposed sandwich structure. A characteristic first reduction couple at 0.32 V indicated reduction of the radical Pc ring of LuPc2. The other redox process indicated electron transfer reactions of each Pc ring, which is in harmony with other sandwich type Pc complexes. Distinct color changes of LuPc2 in solution showed its possible use in the solid state as an electrochromic material; thus, the electrochromic responses were analyzed using a LuPc2 film. Fast, stable and reversible electrochromic responses were observed with green to red color changes.

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Topics: Electrochromism (60%), Phthalocyanine (55%)

Journal ArticleDOI: 10.1039/D1DT02919C
Abstract: This study presents the preparation of a novel tetra-substituted phthalonitrile (1), namely, 3,6-bis(hexyloxy)-4,5-bis(4-(trifluoromethoxy)phenoxy)phthalonitrile (1) and its metal-free (2)/metal {M = Zn (3), Cu (4), Co (5), Lu(CH3COO) (6), Lu (7)} phthalocyanines. A series of various spectroscopic methods (UV-vis, FT-IR, mass, and 1H NMR spectroscopy) were performed for the characterization of the newly synthesized compounds. The potential of compounds 2, 3, and 6 as photosensitizing materials for photodynamic and sonophotodynamic therapies was evaluated by photophysical, photochemical, and sonochemical methods. The highest singlet quantum yields were obtained for the zinc phthalocyanine derivative 3 by performing photochemical and sonochemical methods. In addition, several biological activities of the new compounds 1–7 were investigated. The newly synthesized phthalocyanines exhibited excellent DPPH scavenging activity and also DNA nuclease activity. The antimicrobial activity of the new compounds was evaluated by the disc diffusion assay. Effective microbial cell viability inhibition was observed with phthalocyanine macromolecules. The photodynamic antimicrobial therapy of the phthalocyanines showed 100% bacterial inhibition when compared to the control. They also exhibited significant biofilm inhibition activity against S. aureus and P. aeruginosa. These results indicate that new phthalocyanines are promising photodynamic antimicrobial therapies for the treatment of infectious diseases.

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Topics: Phthalonitrile (55%), Phthalocyanine (52%)

Open accessJournal ArticleDOI: 10.1111/PHP.13553
Abstract: As thiazoles and fluorinated groups are well known as active species of hybrid pharmaceutical agents, this study aimed to evaluate the synergic effect of these groups on the biological features of phthalocyanines for the first time in the hope of discovering efficient pharmaceutical agents. Therefore, a new phthalonitrile derivative namely 4-(2-(4-methylthiazol-5-yl)ethoxy)-5-(4-(trifluoromethoxy)phenoxy)phthalonitrile (1) and its metal-free (2)/metal phthalocyanines (3-5) were prepared and characterized using various spectroscopic techniques. Solubility of new phthalocyanines (2-5) was examined in a series of polar and nonpolar solvents. Additionally, sono/photochemical methods were applied to examine the photophysical and sono/photochemical properties of new zinc phthalocyanine to measure its potential as a probable material for sono/photodynamic therapies. The antioxidant activities of compounds (1-5) were evaluated using the DPPH scavenging activity method and the highest radical scavenging activity was obtained 92.13% (200 mg L-1 ) for manganese phthalocyanine. All the phthalocyanines demonstrated high DNA nuclease activity, as well. The antimicrobial activities of compounds (1-5) were investigated using disk diffusion and microdilution methods. The phthalocyanines exhibited effective microbial cell inhibition activity against Escherichia coli (E. coli). Antimicrobial photodynamic therapy activity was investigated against E. coli by LED irradiation. Compounds (2-5) acted as photosynthesizers. Also, they displayed significant biofilm inhibition activity against Staphylococcus aureus (S. aureus) and Pseudomonas aeruginosa (P. aeruginosa).

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Topics: Phthalonitrile (54%), Phthalocyanine (50%)


49 results found

Journal ArticleDOI: 10.1021/CR00002A004
01 Mar 1991-Chemical Reviews
Abstract: The Hammett equation (and its extended forms) has been one of the most widely used means for the study and interpretation of organic reactions and their mechanisms. Although the Hammett methodology has been criticized by theoreticians because of its empirical foundation, it is astonishing that u constants, obtained simply from the ionization of organic acids in solution, can frequently predict successfully equilibrium and rate constants for a variety of families of reactions in solution. Almost every kind of organic reaction has been treated via the Hammett equation, or its extended form. The literature is so voluminous and extensive that there is no complete review of all that has been accomplished. Hammett's success in treating the electronic effect of substituents on the rates and equilibria of organic reactions1P2 led Taft to apply the same principles to steric and inductive and resonance effects? Then, more recently, octanol/ water partition coefficients (P) have been used for rationalizing the hydrophobic effects of organic compounds interacting with biological systems? The use of log P (for whole molecules) or n (for substituents), when combined with electronic and steric parameters, has opened up whole new regions of biochemical and pharmacological reactions to study by the techniques of physical organic chemistry.sf3 The combination of electronic, steric, hydrophobic, hydrophilic, and hydrogen-bonding7 parameters has been used to derive quantitative structure-activity relationships (QSAR) for a host of interactions of organic compounds with living systems or parts thereof. The binding of organic compounds to proteins,8 their interaction with enzymess and with cellsloJ1 and tiasues,12 their inhibition of organelles,l' and as antimalarial^'^

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Topics: Yukawa–Tsuno equation (69%), Taft equation (67%), Hammett equation (65%) ... show more

6,186 Citations

PatentDOI: 10.1128/AAC.2.1.23
Abstract: There is provided a food-grade microbicidal or microbiostatic composition containing a food or food-grade material and as the primary microbicide a mono-ester of a polyol and a twelve carbon atom aliphatic fatty acid.

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Topics: Fatty acid (60%), Antimicrobial (52%)

953 Citations

Journal ArticleDOI: 10.1021/CR980439Y
Hasrat Ali1, J. E. Van Lier1Institutions (1)
14 Aug 1999-Chemical Reviews

769 Citations

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