Non-aggregated axially disubstituted silicon phthalocyanines: Synthesis, DNA cleavage and in vitro cytotoxic/phototoxic anticancer activities against SH-SY5Y cell line

Barut, Burak; Bıyıklıoğlu, Zekeriya; Yalçın, Can Özgür; Asadi, Mahmoud

doi:10.1016/j.dyepig.2019.107794

Cited by 24 publications

(18 citation statements)

References 28 publications

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“…The protons of Ar-CH 2 , -CH 2 -and Si-O-CH 2 shifted negative [(−0.12)-(−2.03) ppm] for 3PY-Si (Figure 2A) and [(−0.09)-(−2.12) ppm] for 4PY-Si owing to the magnetic anisotropy of the Pc ring. [21] Also, 13 C-NMR spectra supported the 3PY-Si (Figure 2B) and 4PY-Si structures. In the MALDI-TOF MS spectra of 3PY-Si and 4PY-Si, molecular ion peaks at m/z 812.17 [M] + , 812.70 [M] + are in accordance with the calculated values, respectively (Figure S1).…”

Section: Synthesis and Characterizationmentioning

confidence: 63%

Dye‐sensitized solar cells using silicon phthalocyanine photosensitizers with pyridine anchor: Preparation, evaluation of photophysical, electrochemical, and photovoltaic properties

Güzel

Baş

Bıyıklıoğlu

et al. 2021

Applied Organom Chemis

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In this study, novel two silicon phthalocyanine photosensitizers (3PY-Si and 4PY-Si) containing pyridine groups as an electron-withdrawing and anchoring group have been prepared and chemically characterized for dye-sensitized solar cells (DSSCs). Photoelectrochemical and photovoltaic properties of the photosensitizers were evaluated. The new photosensitizers elucidated by spectroscopic and electrochemical techniques. As reported by fluorescence measurements, the silicon phthalocyanine photosensitizers exhibited slightly higher fluorescence quantum yield (Φ F = 0.25) than the unsubstituted zinc phthalocyanine which is favorable for photophysical applications. The DSSC based on complex 3PY-Si shows the highest power conversion efficiency (PCE) of 0.53% with the J sc , V oc and FF values of 1.205 mA cm −2 , 0.612 V, and 0.72, respectively, in the presence of the coadsorbent. These silicon phthalocyanine photosensitizers with bulky axial pyridine substituents found to be important materials for (DSSCs) since they show strong absorption in the red region and their ligands hamper the stacking of rings. This situation prevented the formation of aggregates with a common tendency to photosensitizers on the TiO 2 surface.

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Section: Synthesis and Characterizationmentioning

confidence: 63%

Dye‐sensitized solar cells using silicon phthalocyanine photosensitizers with pyridine anchor: Preparation, evaluation of photophysical, electrochemical, and photovoltaic properties

Güzel

Baş

Bıyıklıoğlu

et al. 2021

Applied Organom Chemis

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“…The synthesis of water‐soluble metallophthalocyanines are given in Figures 2 and 3. DM‐C6‐CN was prepared by the reaction of DM‐C6‐OH [ 39 ] and 4‐nitrophthalonitrile in DMF at 60°C. The metallophthalocyanines ( DM‐C6‐Co , DM‐C6‐Cu , and DM‐C6‐Mn ) were synthesized by reaction of DM‐C6‐CN and metal salts in 1‐pentanol.…”

Section: Resultsmentioning

confidence: 99%

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

Bıyıklıoğlu

Baş

Akkaya

et al. 2022

Applied Organom Chemis

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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.

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“…The studied macromolecules displayed acceptable pBR322 DNA cleavage activities under irradiation. 56 Compared to the literature, compounds 1-QSi (50-200 mg mL À1 ) and 3-QSi (200 mg mL À1 ) can be used as anticancer drugs after further investigations.…”

Section: Dna Cleavage Assaymentioning

confidence: 99%

Anticancer activity of novel silicon phthalocyanines against the colorectal adenocarcinoma cell line (DLD-1)

et al. 2022

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Non-aggregated axially disubstituted silicon phthalocyanines: Synthesis, DNA cleavage and in vitro cytotoxic/phototoxic anticancer activities against SH-SY5Y cell line

Cited by 24 publications

References 28 publications

Dye‐sensitized solar cells using silicon phthalocyanine photosensitizers with pyridine anchor: Preparation, evaluation of photophysical, electrochemical, and photovoltaic properties

Dye‐sensitized solar cells using silicon phthalocyanine photosensitizers with pyridine anchor: Preparation, evaluation of photophysical, electrochemical, and photovoltaic properties

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

Anticancer activity of novel silicon phthalocyanines against the colorectal adenocarcinoma cell line (DLD-1)

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