title: Synthesis, aggregation and spectroscopic studies of novel water soluble metal free, zinc, copper and magnesium phthalocyanines and investigation of their anti-bacterial properties.
abstract: In this study, novel phthalonitrile derivative (3) was synthesized by the reaction between 4-nitrophthalonitrile (2) and a triazole derivative (1) containing pyridine moiety. Crystal structure of compound (3) was characterized by X-ray diffraction. New metal free and metallo-phthalocyanine complexes (Zn, Cu, and Mg) were synthesized using the phthalonitrile derivative (3). Cationic derivatives of these phthalocyanines (5, 7, 9, and 11) were prepared from the non-ionic phthalocyanines (4, 6, 8, and 10). All proposed structures were supported by instrumental methods. The aggregation behaviors of the phthalocyanines (4-11) were investigated in different solvents such as dimethylsulfoxide (DMSO), N,N-dimethylformamide (DMF), chloroform and water. Water soluble cationic Pcs (5, 7, 9, and 11) aggregated in water and sodium dodecyl sulfate was used to prevent the aggregation. The second derivatives of the UV-Vis spectra of aggregated Pcs were used for analyzing the Q and B bands of aggregated species. Thermal behaviors of the phthalocyanines were also studied. In addition, anti-bacterial properties of the phthalocyanines were investigated. We used four gram negative and two gram positive bacteria to determine antibacterial activity of these compounds. Compound 7 has the best activity against the all bacteria with 125μg/mL of MIC value. Compounds 4, 6, and 10 have the similar effect on the bacteria with 250μg/mL of MIC value.
authors: Department of Chemistry, Faculty of Arts and Sciences, Sinop University, 57000 Sinop, Turkey. Electronic address: bayrakriza@ktu.edu.tr.
authors: Rıza
authors: R
authors: Bayrak
authors: Department of Chemistry, Faculty of Art and Sciences, Recep Tayyip Erdoğan University, 53100 Rize, Turkey.
authors: Hakkı Türker
authors: HT
authors: Akçay
authors: Department of Biology, Faculty of Sciences, Recep Tayyip Erdogan University, 53100 Rize, Turkey.
authors: Fatih Şaban
authors: FŞ
authors: Beriş
authors: Department of Chemistry, Faculty of Science, Atatürk University, 2524 Erzurum, Turkey.
authors: Ertan
authors: E
authors: Sahin
authors: Department of Chemistry, Faculty of Sciences, Karadeniz Technical University, 61100 Trabzon, Turkey.
authors: Hacer
authors: H
authors: Bayrak
authors: Department of Chemistry, Faculty of Sciences, Karadeniz Technical University, 61100 Trabzon, Turkey.
authors: Ümit
authors: Ü
authors: Demirbaş
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001424:Bacterial Infections / Q000188:drug therapy; D003300:Copper / Q000737:chemistry* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D006801:Humans; D007211:Indoles / Q000737:chemistry* / Q000494:pharmacology; D054833:Isoindoles; D008274:Magnesium / Q000737:chemistry* / Q000494:pharmacology; D008958:Models, Molecular; D009942:Organometallic Compounds / Q000737:chemistry* / Q000494:pharmacology; D012995:Solubility; D014867:Water / Q000737:chemistry; D015032:Zinc / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D007211:Indoles; D054833:Isoindoles; D009942:Organometallic Compounds; D014867:Water; D003300:Copper; D008274:Magnesium; D015032:Zinc; C013647:phthalocyanine
keywords: Aggregation; Anti-bacterial activity.; Cationic phthalocyanine; Sodium dodecylsulfate; Thermal stability; X-ray diffraction