Synthesis and characterization of newly phthalocyanine molecules: Their enzyme inhibition and antioxidant properties, in silico and in vitro

• Published in: Journal of organometallic chemistry Vol. 1016; pp. 123237 - 123250
• Main Authors: Çelik, Fatih, Ünver, Yasemin, OzTuncay, Fulya, Cakmak, Ummuhan, Kolcuoglu, Yakup, Uzun, Kübra Karaoğlu, Ozturk, Hilal, Yorulmaz, Nuri, Değirmencioğlu, İsmail
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.08.2024; Elsevier
• Subjects: Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; In silico; Inhibition; Phthalocyanine; Physical Sciences; Science & Technology; Tyrosinase; Α-amylase; Phthalocyanine; In silico; Inhibition; Α-amylase; Tyrosinase; PHOTODYNAMIC THERAPY; DERIVATIVES; Acy;-amylase
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/j.jorganchem.2024.123237

•Synthesis and characterization of novel 1,2,3-triazole schiff base fragmented silicon phthalocyanine complexes (6a and 6b).•Investigation of their α-amylase inhibition properties of the synthesized phthalocyanines.•Investigation of their tyrosinase inhibition properties of the synthesized phthalocyanines.•Investigation of their optical properties (such as molecular electrostatic potentials, frontier orbital analysis, natural bond orbital (nbo) properties) due to the DFT and TD-DFT methods. Pcs exhibiting maximum absorption in the phototherapeutic window continue to shine as a beacon of hope in the treatment of cancer. In particular, they maintain skin sensitivity after treatment and can treat deep-seated tumors by stimulating them with broad-spectrum radiation. This makes them advantageous compared to their counterparts. In this study, Novel 1,2,3-triazole schiff base (5a), its methoxy homolog (5b), and their silicon complexes (SiPc-6a and SiPc-6b) were synthesized. Their proposed structures were confirmed by FT-IR, NMR, UV–vis and MS instrumental techniques. Compound (6b) showed inhibitory activity on amylase and glucosidase enzymes. Moreover, considering the glucosidase activity, compound (6b) (IC50, 22.4 ± 1.0 µM) was observed to be more effective than the standard compound (IC50, 186.1 ± 5.8 µM). Molecular docking studies showed that the synthesized compounds bind to the same enzymes with high affinity. The binding energy of SiPc-6a compound with α-amylase, α-glucosidase and tyrosinase enzymes are -10.28, -11.31 and -11.9 kcal/mol, respectively. And another compound, SiPc-6b, has a binding energy of -11.46, -10.11 and -10.27 kcal/mol with a-amylase, a-glucosidase and tyrosinase enzymes, respectively. Based on experimental results that support each other with binding energy values in quality and quantity indicating efficient binding, it is concluded that these compounds can be used in candidate drug discovery. Beside these, as a result of the studies, it was understood that all molecules have antioxidant activity. Additionally, molecular electrostatic potentials, frontier orbital analysis, natural bond orbital (NBO) properties of compounds calculated with DFT and TD-DFT methods and these properties associated with structural properties. [Display omitted]