Synthesis and antimicrobial activity of meso-substituted polymethine cyanine dyes

• Published in: Bioorganic chemistry 2004-08, Vol.32 (4), p.193-210
• Main Authors: Abd El-Aal, R.M, Younis, M
• Format: Article
• Language: English
• Subjects: Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - pharmacology; Antimicrobial activity; Carbocyanines - chemical synthesis; Carbocyanines - pharmacology; Coloring Agents - chemical synthesis; Coloring Agents - pharmacology; Cyanine dyes; Fungi - drug effects; Gram-Negative Bacteria - drug effects; Gram-Positive Bacteria - drug effects; Microbial Sensitivity Tests; Molecular Structure; Photosensitizing Agents - chemical synthesis; Solvatochromism; Solvents; Spectrum Analysis; Yeasts - drug effects
• ISSN: 0045-2068; 1090-2120
• DOI: 10.1016/j.bioorg.2004.04.001

The condensation reaction of equivalent amounts of 2-cyanomethyl benzooxazole or its derivatives with variously substituted aromatic aldehydes gave 2-cyano-styryl benzooxazole or its derivatives. The subsequent reaction of the 2-cyano-styryl benzooxazoles with 2(4)-methyl substituted heterocyclic quaternary salts afforded meso-substituted styryl-2(4)-polymethine cyanines. The condensation reaction of 2-cyanomethyl benzooxazole or its derivatives with α-nitroso-β-naphthol followed by reaction with 2(4)-methyl substituted heterocyclic quaternary salts gave meso-substituted aza-2(4)-polymethine cyanines. The reaction of 2-cyanomethyl benzooxazole or its derivatives with N-methyl heterocyclic quaternary salts followed by the reaction with 2-methylquinolinium methiodide afforded the corresponding meso-substituted trimethine cyanine dyes. Elemental analyses, visible absorption, IR, 1H NMR spectroscopy, and mass spectra established the structures of these compounds. The relationship between the structure and properties of these dyes has been studied and the solvatochromic behavior of some selected cyanine dyes in organic solvents is discussed. Finally, the antimicrobial activity of selected novel dyes was investigated in vitro using a wide spectrum of microbial strains.