Synthesis of New Axially Coumarin Disubstituted Silicon(IV) Phthalocyanines, Investigation of their DNA-Binding Properties and Inhibitory Activities on Ache and Buche

Güneş A., MELETLİ F., DANIŞ Ö., Ağırtaş M. S., YALÇIN B.

Current Topics in Medicinal Chemistry, 2025 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2025
  • Doi Numarası: 10.2174/0115680266368541250311084659
  • Dergi Adı: Current Topics in Medicinal Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Biotechnology Research Abstracts, Chemical Abstracts Core, EMBASE, MEDLINE
  • Anahtar Kelimeler: AChE, BuChE, coumarin, DNA-binding, Silicon(IV) phthalocyanines, singlet oxygen
  • Van Yüzüncü Yıl Üniversitesi Adresli: Evet

Özet

Introduction: In this study, we report on the synthesis and characterization of new silicon (IV) phthalocyanine compounds (SiPcs) axially substituted with coumarin-linked derivatives, designed for potential application in photodynamic therapy (PDT) due to their photophysical properties. Methods: Characterization was carried out using FT-IR, UV-Vis, MALDI-TOF-MS, and 1H NMR spectroscopy. In dimethyl sulfoxide (DMSO), the SiPcs produced singlet oxygen with quantum yields of 0.17 to 0.19, assessed by the DPBF quenching method. DNA binding studies via UV-Vis spectroscopy and molecular docking suggested high binding affinities (ΔG0 values between -9.90 to -10.4 kcal/mol) and stable interactions with calf thymus DNA (ct-DNA). Results: The compounds showed promising inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), with IC50 values indicating higher potency and selectivity compared to galantamine, a known cholinesterase inhibitor. Conclusion: The combined singlet oxygen generation, DNA binding, and enzyme inhibition data underscore the potential of these SiPc-coumarin derivatives as multifunctional agents for PDT and neuroprotective applications such as Alzheimer's disease (AD).