From antioxidants to apoptosis: How chain length governs phthalocyanine biofunctionality

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Bahar D., Yenilmez H. Y., Derya Andeden M., Güler N.

POLYHEDRON, cilt.300, sa.118433, ss.1-11, 2026 (SCI-Expanded, Scopus)

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 300 Sayı: 118433
  • Basım Tarihi: 2026
  • Doi Numarası: 10.1016/j.poly.2026.118433
  • Dergi Adı: POLYHEDRON
  • Derginin Tarandığı İndeksler: Academic Search Ultimate (EBSCO), Engineering Source (EBSCO), Scopus, Science Citation Index Expanded (SCI-EXPANDED), Chemical Abstracts Core, Chimica, Compendex
  • Sayfa Sayıları: ss.1-11
  • Açık Arşiv Koleksiyonu: AVESİS Açık Erişim Koleksiyonu
  • Kayseri Üniversitesi Adresli: Evet

Özet

In this study, tetra-substituted zinc and indium phthalocyanines with different chain lengths were synthesized. All compounds were characterized by FT-IR, 1 H NMR, MALDI-TOF, and UV–vis spectroscopy. The in vitro anticancer/cytotoxic properties of the compounds were investigated using 3-(4,5-dimethylthiazol-2-yl)-2,5- diphenyltetrazolium (MTT) assay in colorectal cancer cell lines (DLD-1 and HT29 cells). The effects of chain length and central metal atom on the cytotoxic properties of the phthalocyanine compounds were compared. Fluorescence quantum yields and lifetimes of the phthalocyanine derivatives were determined. Additionally, the singlet oxygen quantum yields of the quaternized phthalocyanine derivatives were determined. The antioxidant activities of the phthalocyanine derivatives were examined using 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The phthalocyanine derivatives exhibited lower DPPH radical-scavenging activity (4.0–53.8%) than BHT (88.0%), indicating modest and compound-dependent cell-free radical-scavenging activity. The compounds were screened for cytotoxic and apoptotic effects against human colon cancer cell lines (DLD-1 and HT29) using MTT and Annexin V assays. The results showed that the compounds have antiproliferative and apoptotic effects against DLD-1 and HT29 cell lines. Overall, the derivatives exhibited distinct photophysical, cell-free radicalscavenging, and cell-line-dependent cytotoxic and apoptotic profiles. However, further mechanistic studies are required to determine whether these properties are functionally related.