Synthesis, aggregation and spectroscopic studies of novel water soluble metal free, zinc, copper and magnesium phthalocyanines and investigation of their anti-bacterial properties

Spectrochim Acta A Mol Biomol Spectrosc. 2014 Dec 10;133:272-80. doi: 10.1016/j.saa.2014.05.075. Epub 2014 Jun 7.

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.

Keywords: Aggregation; Anti-bacterial activity.; Cationic phthalocyanine; Sodium dodecylsulfate; Thermal stability; X-ray diffraction.

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Bacteria / drug effects
  • Bacterial Infections / drug therapy
  • Copper / chemistry*
  • Copper / pharmacology
  • Crystallography, X-Ray
  • Humans
  • Indoles / chemistry*
  • Indoles / pharmacology
  • Magnesium / chemistry*
  • Magnesium / pharmacology
  • Models, Molecular
  • Organometallic Compounds / chemistry*
  • Organometallic Compounds / pharmacology
  • Solubility
  • Water / chemistry
  • Zinc / chemistry*
  • Zinc / pharmacology

Substances

  • Anti-Bacterial Agents
  • Indoles
  • Organometallic Compounds
  • Water
  • Copper
  • Magnesium
  • Zinc
  • phthalocyanine