Novel water-soluble metal-free and metallophthalocyanines: Synthesis, spectroscopic characterization and aggregation properties

In this work, 3-({6-[3-(dimethylamino)phenoxy]hexyl}oxy)phthalonitrile ( 2) and the target zinc (II) phthalocyanine (3) and its ammonium derivative (3a) are synthesized, and the phototoxic effects of 3a were examined using different methods on A549 lung cancer cells. Then, the toll-like receptor (TLR) signaling pathway was examined to determine the cell death mechanism in the A549 cancer cells. The results showed that 3a did not have noticeable cytotoxic actions on A549 cells at used concentrations. However, the compound markedly reduced the cell viability when irradiated by the red light for 5 and 15 min (LumaCare/LC-122A/LC2020-09-784, Prob: LUM L [700 nm CL] [15 mW cm À2 ]). Additionally, Annexin V/PI staining suggested that the cells were induced apoptosis in the presence of 3a (1 μM) when irradiated with red light for 15 min. Furthermore, the expression of TLR2, TLR4, and caspase-3 significantly increased and phospho-nuclear factor kappa B/total nuclear factor kappa B decreased compared with that of control group (p < 0.05). These results provide strong evidence that 3a is able to induce A549 cell death in a dose and a red-light irradiation time-dependent manner via apoptosis. Therefore, 3a might be an effective photodynamic therapy candidate for lung cancer treatment.

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Evaluation of photodynamic therapy effects of novel zinc (II) phthalocyanine through a possible interaction with toll‐like receptor signaling pathway

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et al. 2023

“…The 1 H‐NMR and 13 C‐NMR spectra of DM‐C6‐Co , DM‐C6‐Cu , DM‐C6‐Mn, DM‐C6‐CoQ , DM‐C6‐CuQ , and DM‐C6‐MnQ could not be recorded due to the paramagnetic metal ions in the ring center. [ 41,42 ] The molecular ion peaks of DM‐C6‐Co , DM‐C6‐Cu , and DM‐C6‐Mn were observed at 1512.63 [M] + , 1517.06 [M] + , and 1508.46 [M‐Cl] + m / z , respectively, in mass spectra. Also, the [(M‐4I)/4] + signals were observed at 393.56 [(M‐4I)/4] + , 394.14 [(M‐4I)/4] + , and 392.22 [(M‐Cl‐4I)/4] + in mass spectra, supported the proposed structures of DM‐C6‐CoQ , DM‐C6‐CuQ , and DM‐C6‐MnQ , respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of peripherally tetra‐({6‐[3‐(dimethylamino)phenoxy]hexyl}oxy) substituted water‐soluble phthalocyanines as cholinesterases inhibitors

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et al. 2022

In this paper, we synthesized peripherally tetra‐({6‐[3‐(dimethylamino)phenoxy]hexyl}oxy) substituted water‐soluble metallophthalocyanines (DM‐C6‐CoQ, DM‐C6‐CuQ, DM‐C6‐MnQ) and investigated their in vitro cholinesterases inhibitory properties by using the spectrophotometric method. The results revealed that the compounds inhibited cholinesterases and had remarkable inhibitory effects when compared with galantamine (p < 0.0001). The IC50 values of the compounds ranged from 2.11 ± 0.20 to 16.40 ± 1.25 μM for AChE and BuChE. Also, the inhibitory type and inhibition constant (Ki) of the compounds were evaluated using Lineweaver–Burk and Dixon plots. These plots showed that DM‐C6‐CoQ, DM‐C6‐CuQ, and DM‐C6‐MnQ were mixed inhibitors against AChE and DM‐C6‐MnQ is the strongest binding inhibitor to the enzyme. Also, DM‐C6‐CoQ inhibited BuChE via competitive manner with 10.05 ± 0.55 μM of Ki value. These results demonstrated that the compounds might be effective agents against Alzheimer's disease.

“…[ 8 ] Pcs are used in industry, biomedical, and therapeutic areas because of their physical and chemical properties. [ 9–13 ] In addition, Pcs can be coordinated with almost all metals such as zinc (II), silicon (IV), gallium (III), iron (II), cobalt (II), copper (II), etc. The zinc metal is one of the most suitable metals for PDT, considering the effect of electron configuration among them.…”

Section: Introductionmentioning

confidence: 99%

DNA interaction, cytotoxic and phototoxic properties of new water‐soluble zinc (II) phthalocyanines

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et al. 2022

In this paper, we have synthesized water‐soluble peripherally tetra and octa‐({6‐[3‐(dimethylamino)phenoxy]hexyl}oxy) groups substituted zinc (II) phthalocyanines (DM‐C6‐ZnQ and o‐DM‐C6‐ZnQ). Also, we have investigated ct‐DNA binding, supercoiled plasmid DNA cleavage properties of DM‐C6‐ZnQ and o‐DM‐C6‐ZnQ by using spectrophotometric and electrophoretic methods. On the other hand, cytotoxic and phototoxic effects of DM‐C6‐ZnQ and o‐DM‐C6‐ZnQ were examined using (3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide (MTT) assay on human lung adenocarcinoma (A549) cell lines. In UV–Vis absorption studies, hypochromism was observed about 18% for DM‐C6‐ZnQ and 57% for o‐DM‐C6‐ZnQ on addition of increasing concentrations of ct‐DNA. The intrinsic binding constant (Kb) values of DM‐C6‐ZnQ and o‐DM‐C6‐ZnQ were 3.82 (±0.14) × 104 M−1 and 2.34 (±0.05) × 105 M−1, respectively. The supercoiled plasmid DNA cleavage studies showed that DM‐C6‐ZnQ and o‐DM‐C6‐ZnQ had no DNA damage actions in the dark. On the other hand, they caused DNA damage depending on the light dose. In the MTT assay, the compounds had low cytotoxic properties on A549 cell lines, but they showed significant phototoxic actions. These results reveal that the compounds interact with DNA and have phototoxic properties; it has been determined that they have the potential to be photosensitizing agents for photodynamic therapy.