Synthesis, characterization and in vitro antimicrobial activity of a new fluorescent tris-benzo[de]anthracen-7-one and its Cu(II) complex

Abstract A new green fluorescent tripod has been synthesised by reaction of 2-chloro-N-(7-oxo-7H-benzo[de]anthracene-3-yl)-acetamide and benzene-1,3,5,-tricarboxylic acid (BT). A Cu(II) complex of the tripod has been also synthesized [Cu(BT)SO4]. The basic photophysical characteristics have been investigated in organic solvents of different polarity. It has been found that the new compound is solvatochromic in nature. Antibacterial and antifungal activity of the new [Cu(BT)SO4] has been investigated. It has been found that the complex has good antibacterial and antifungal potential suggesting opportunities for its application in biomedicine for designing new effective antimicrobial preparations such as effective antibacterial wound dressings for treatment modalities of chronic wounds.

[1]  J. Chovelon,et al.  Synthesis of benzanthron derivatives for selective detection by fluorescence of copper ions , 2009 .

[2]  J. Chovelon,et al.  Optical sensor for aliphatic amines based on the simultaneous colorimetric and fluorescence responses of smart textile , 2007 .

[3]  I. Boyaci,et al.  Synthesis, characterization and in vitro antimicrobial activity of a new blue fluorescent Cu(II) metal complex of bis-1,8-naphthalimide , 2015 .

[4]  L. Silver Challenges of Antibacterial Discovery , 2011, Clinical Microbiology Reviews.

[5]  M. Willis,et al.  Zinc-induced copper deficiency: a report of three cases initially recognized on bone marrow examination. , 2005, American journal of clinical pathology.

[6]  V. Bojinov,et al.  Synthesis of ethyl 3-aryl-1-methyl-8-oxo- 8H-anthra[9,1-gh]quinoline-2-carboxylates as dyes for potential application in liquid crystal displays. , 2003, Organic letters.

[7]  Abdullah M. Asiri,et al.  Synthesis and spectral characterization of a new PPA dendrimer modified with 4-bromo-1,8-naphthalimide and in vitro antimicrobial activity of its Cu(II) and Zn(II) metal complexes , 2015 .

[8]  G. Plesch,et al.  Coordination geometries and cooperative ordering effects in copper(II) complexes with tridentate Schiff base dianions—III. EPR study on N-salicylideneglycinatocopper(II) complexes with thiourea derivatives , 1991 .

[9]  S. Belyakov,et al.  Fluorescent substituted amidines of benzanthrone: synthesis, spectroscopy and quantum chemical calculations. , 2013, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[10]  Kathryn L Haas,et al.  Application of metal coordination chemistry to explore and manipulate cell biology. , 2009, Chemical reviews.

[11]  E. Vasileva-Tonkova,et al.  Poly(propylenamine) dendrimers modified with 4-amino-1,8-naphthalimide: Synthesis, characterization and in vitro microbiological tests of their Cu(II) and Zn(II) complexes , 2015 .

[12]  P. Kinnunen,et al.  Newly synthesized benzanthrone derivatives as prospective fluorescent membrane probes , 2014 .

[13]  J. Chovelon,et al.  Fluorescent benzo[de]anthracen-7-one pH-sensor in aqueous solution and immobilized on viscose fabrics , 2006 .

[14]  Combination of sensor potential and antimicrobial activity of a new 4-(2-dimethylaminoethyloxy)-N-buthyl-1,8-naphthalimide , 2014 .

[15]  D. Staneva,et al.  Synthesis and functional properties of new optical pH sensor based on benzo[de]anthracen-7-one immobilized on the viscose , 2007 .

[16]  I. Grabchev,et al.  Synthesis and properties of benzanthrone derivatives as luminophore dyes for liquid crystals , 1998 .

[17]  A. Asiri,et al.  Synthesis, photophysical and antimicrobial activity of new water soluble ammonium quaternary benzanthrone in solution and in polylactide film. , 2015, Journal of photochemistry and photobiology. B, Biology.

[18]  V. Bojinov,et al.  Functional properties of azomethine substituted benzanthrone dyes for use in nematic liquid crystals , 1998 .

[19]  R. Weigand,et al.  Solvent dependence of the inhibition of intramolecular charge-transfer in N-substituted 1,8-naphthalimide derivatives as dye lasers , 1996 .