Synthesis and multi-biological evaluation of octa-substituted MESNA-phthalocyanines: from sono-photochemical to antimicrobial, anticancer, enzyme inhibition and in silico studies
Journal of Molecular Structure, cilt.1378, 2026 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 1378
- Basım Tarihi: 2026
- Doi Numarası: 10.1016/j.molstruc.2026.147220
- Dergi Adı: Journal of Molecular Structure
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Chimica, Compendex, INSPEC, Academic Search Ultimate (EBSCO), Engineering Source (EBSCO)
- Anahtar Kelimeler: Anticancer, Antimicrobial, Molecular docking, Phthalocyanine, Singlet oxygen, Sono-photochemical
- Yıldız Teknik Üniversitesi Adresli: Evet
Özet
This work reports the first-time synthesis of a novel starting compound, 4,5-bis(sodium 2-mercaptoethane sulfonate) phthalonitrile (1), and its transformation into a new series of water-soluble phthalocyanine derivatives bearing eight MESNA (sodium 2-mercaptoethanesulfonate) groups at the peripheral octa-positions. The resulting metallophthalocyanines-Cu(II) (2), MnCl(III) (3), GaCl(III) (4), and InCl(III) (5)-were successfully obtained and thoroughly characterized using a range of spectroscopic techniques, including UV–Vis, FT-IR, ¹H NMR, ¹³C NMR, and MALDI-TOF MS. The potential of photochemical and sono-photochemical techniques to enhance singlet oxygen (¹O₂) generation was evaluated. In this study, synthesized GaCl(III)Pc (4) and InCl(III)Pc (5) were investigated under both light-only and combined light + ultrasound conditions. The phthalocyanines demonstrated significant singlet oxygen quantum yields (ΦΔ), with gallium-based derivatives in particular showing enhanced 1O2 production, likely due to favorable triplet-state lifetimes and photophysical properties. These findings highlight the effectiveness of combining photochemical and sonochemical activation and underscore the promise of Ga(III) and In(III) phthalocyanines as potent photosensitizers in next-generation PDT and SPDT applications. The cytotoxic effects of the compounds on A549 lung cancer and C6 rat glioma cell lines were evaluated using the MTT test. Additionally, the inhibitory effects of the compounds on CA I and CA II enzymes were investigated. The results showed that these compounds inhibited CA I and CA II enzymes in a dose-dependent manner, and also had an effect that enhanced the destruction of cancer cells. In this study, the antioxidant activities of Ga(III)ClPc (4), Cu(II)Pc (2), In(III)ClPc (5), and Mn(III)ClPc (3) phthalocyanine derivatives were evaluated and compared with the standard antioxidant ascorbic acid by determining their IC50 values. Among the tested phthalocyanine complexes, In(III)ClPc (2367 ± 1.57 μg/mL) exhibited the highest antioxidant activity with the lowest IC50 value, whereas Mn(III)ClPc (3) (3093 ± 1.66 μg/mL) showed the weakest activity. The activity ranking of the phthalocyanine complexes was determined as In(III)ClPc (5) > Ga(III)ClPc (4) > Cu(II)Pc (2) > Mn(III)ClPc (3). newly synthesized metal phthalocyanine derivatives were evaluated for their in vitro antimicrobial activity against American Type Culture Collection (ATCC) reference strains using the broth microdilution method. The compounds exhibited selective antimicrobial activity, with MIC values ranging from 2.5 to 9.8 mg/mL. The lowest MIC value was observed against Bacillus cereus (2.5 mg/mL). Moderate antibacterial activity was detected against Escherichia coli (4.8–4.9 mg/mL) and Pseudomonas aeruginosa (4.7 mg/mL) for selected derivatives. Antifungal activity against Candida albicans was observed for gallium and manganese-containing compounds (4.8 mg/mL). In contrast, no effective inhibition was detected against Klebsiella pneumoniae or Staphylococcus aureus within the tested concentration range. These findings indicate that metal-dependent structural variations significantly influence the antimicrobial activity of phthalocyanine derivatives.