Synthesis, Physicochemical Properties and Anti-Fungal Activities of New Meso-Arylporphyrins.

In this work, we describe the synthesis of three new meso-arylporphyrins, named meso-tetrakis [4-(nicotinoyloxy)phenyl] porphyrin (H2TNPP), meso-tetrakis [4-(picolinoyloxy)phenyl] porphyrin (H2TPPP), and meso-tetrakis [4-(isonicotinoyloxy) phenyl] porphyrin (H2TIPP). These new synthesized meso-arylporphyrins are characterized using spectroscopic analysis: Fourier Transform Infrared Spectroscopy (FTIR) and One-dimensional Nuclear Magnetic Resonance (1D NMR), and mass spectrometry (MS). The photophysical studies (UV-visible absorption, singlet oxygen (1O2) luminescence, and fluorescence emissions) demonstrate their potential uses as photosensitizers (PSs) in photodynamic therapy (PDT) applications. An in vitro investigation of the anti-fungal activity of H2TNPP, H2TPPP, and H2TIPP against Candida (C.) species (C. albicans, C. glabrata, and C. tropicalis) reveals that their minimum inhibitory concentration (MIC) values ranged from 1.25 to 5 mg/mL. In addition, their in vitro anti-fungal susceptibilities against three dermatophyte clinical isolates (Trichophyton rubrum, Microsporum canis, and Trichophyton mentagrophytes) are also evaluated and they demonstrate good anti-fungal activities. A molecular docking study of these meso-arylporphyrins as anti-fungal agents against C. tropicalis extracellular aspartic proteinases, Protein data Bank in Europe (PDBe code: 1J71) and Trichophyton rubrum Sialidases (PDBe code: 7P1D) underlines the possible interactions of H2TNPP, H2TPPP, and H2TIPP with the key amino acid residues of these fungal target proteins.