Investigation of the photophysical, photochemical, and multifunctional biological properties of fluorinated zinc(ii) phthalocyanine functionalized with carboxylic acid


Özay G., Özçeşmeci M., IŞIK Ş., CAN KARANLIK C., Kalkan Burat A., ERDOĞMUŞ A., ...Daha Fazla

Dalton Transactions, 2026 (SCI-Expanded, Scopus) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2026
  • Doi Numarası: 10.1039/d5dt02774h
  • Dergi Adı: Dalton Transactions
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Chimica, Compendex, MEDLINE
  • Acıbadem Mehmet Ali Aydınlar Üniversitesi Adresli: Evet

Özet

In this study, a peripherally tetra-substituted zinc phthalocyanine with 2′,3′,5′,6′-tetrafluoro-4′-carboxyethylthio-benzyloxy groups (2) was synthesized. FT-IR, NMR, MALDI-TOF MS, and UV-Vis spectroscopy techniques were used to characterize all the synthesized compounds. The photochemical and photophysical properties of compound 2 were also examined. The singlet oxygen quantum yield was calculated as 0.49 for compound 2 using only light irradiation in the photochemical method. Additionally, compound 2 showed moderate photostability under intense light irradiation. The biological properties of compound 2, including antioxidant, antidiabetic, antimicrobial, DNA cleavage, and anti-biofilm activities, were evaluated. The antioxidant activity was measured using the DPPH radical scavenging assay, where compound 2 demonstrated 18.12% activity. The antidiabetic potential was assessed through amylase inhibition tests, indicating that compound 2 has potential antidiabetic activity. The antimicrobial activity of compound 2 was tested with the microdilution method. It showed significant activity, especially against Gram-positive and Gram-negative bacteria. Furthermore, the antimicrobial effects of compound 2via photodynamic therapy showed enhanced activity. E. coli was used to evaluate the inhibitory effect of compound 2 on cell viability, demonstrating 100% inhibition. The compound's ability to inhibit biofilm formation of S. aureus and P. aeruginosa was also assessed, with compound 2 showing high biofilm inhibition. The anti-biofilm effect was generally more pronounced against S. aureus than P. aeruginosa. Importantly, the biocompatibility of compound 2 was confirmed in L929 fibroblast cells. While it exhibited concentration-dependent cytotoxicity in the dark, under light irradiation, cell viability remained close to or above the thresholds defined by ISO 10993-5 for non-cytotoxicity. As a result, compound 2 is a multifunctional phthalocyanine derivative that combines diverse biological activities with a safety profile, supporting its potential as a promising candidate for biomedical applications.