Novel Cationic Dye Based on Naphthalimide: Part 1: Synthesis, Characterization and Evaluation of Biology Efficacy as Antimicrobial Agent


Journal: Vol.9, No.4, autumn 2016 - Article 5   Pages :  261 Until 268



Article Code:
PCCC-2016-08-27-335

Authors:
Hanieh Shaki: Golestan University - Chemical Engineering
A. Khosravi: Amirkabir University of Technology - Department of Polymer Engineering and Color Technology
K. Gharanjig: Institute for Color Science and Technology - Department of Organic Colorants


Article's abstract:

In this paper, synthesis and antimicrobial properties of cationic dye were investigated. 4-acetylamino-N-2-aminomethylpyridine-1,8-naphthalimide was reacted with 1-bromobutane as the alkylating agent and a cationic dye was obtained. The final product was purified by column chromatography method. The chemical structure of the novel cationic dye and its intermediates was chracterisized by using FTIR, 1HNMR, 13CNMR and DSC techniques. The antimicrobial efficacy of the dye was evaluated by using a minimum inhibitory cocentration MIC and disk difusion methods. The synthesized dye and its intermediates showed good antimicrobial activities against both Gram positive and Gram negative bacteria. Also, the results indicated that cationic dye 3 containing 1-bromobutane as the alkylating agent had highest antimicrobial activity against all the bacteria used.The MIC of the novel cationic dye against E. coli was 125 μg ml−1 and S.aureus was 62.5 μg ml−1.


Keywords:
Cationic dye, Naphthalimide, Antimicrobial agent, Synthesis, Aminomethylpyridine.

References:
[1] J. Griffiths, The Functional Dyes – Definition, Design and Development, Chimia., 45 (1991), 304-307. [2] G. Sun, M. Ma, Multifunctional antimicrobial dyes, US 20050011012 A1, 2005. [3] Y.C. Chao, M. J. Chang, C.H. Chang, Water-repellent acid dyes: The influence of the perfluorobutamido group on the colour, dyeing and fastness properties of 2-(p-alkyl) phenylazo-1-naphthol acid dyes, Dyes Pigments, 39 (1998), 183-191. [4] M. Hosseinnezhad, S. Moradian, K. Gharanjig, Acid azo dyes for efficient molecular photovoltaic: study of dye-sensitized solar cells performance, Prog. Color Colorants Coat., 9 (2016), 61-70. [5] M. Ma, Y. Sun, G. Sun, Antimicrobial cationic dyes: part 1: synthesis and characterization, Dyes Pigments, 58 (2003), 27-35. [6] J. Liu, G. Sun, The synthesis of novel cationic anthraquinone dyes with high potent antimicrobial activity, Dyes Pigments, 77 (2008), 380-386. [7] J. Liu, G. Sun, The biocidal properties of anthraquininoid dyes, Dyes Pigments, 81 (2009), 231–234. [8] T. Zhao, G. Sun, Antimicrobial Finishing of Cellulose with Incorporation of Aminopyridinium Salts to Reactive and Direct Dyed Fabrics, J. Appl. Polym. Sci., 106 (2007), 2634–2639. [9] S. Liu, J. Ma, D. Zhao, Synthesis and characterization of cationic monoazo dyes incorporating quaternary ammonium salts, Dyes Pigments, 75 (2007), 255-262. [10] H. Shaki, K. Gharanjig, Sh. Rouhani, A. Khosravi, J. Fakhar, Synthesis and application of some novel antimicrobial monoazonaphthalimide dyes: synthesis and characterisation, Color. Technol., 128 (2012), 270-275. [11] H. Shaki, K. Gharanjig, S. Rouhani, A. Khosravi, Synthesis and photophysical properties of some novel fluorescent dyes based on naphthalimide derivatives, J Photoch Photobio A Chem., 216 (2010), 44-50. [12] H. Shaki, A. Khosravi, K. Gharanjig, A. Mahboubi, Investigation of synthesis, characterization, photophysical and biological properties of novel antimicrobial fluorescent naphthalimide derivatives, Mater Technol. Adv. Performance Materials., 31(2016), 322-331. [13] M. Yu , W. Du, W. Zhou, H. Li, C. Liu, L. Wei, Z. Li, H. Zhang, A 1,8-naphthalimide-based chemosensor with an off-on fluorescence and lifetime imaging response for intracellular Cr3 and further for S2−, Dyes Pigments, 126, (2016), 279–285. [14] Y. Niu, Y. Qian, Synthesis and aggregation-induced emission enhancement of naphthalimide-rhodamine dye, J Photoch Photobio A Chem., 329, (2016), 88–95. [15] H. Shaki, K. Gharanjig, A. Khosravi, Synthesis and investigation of antimicrobial activity and spectrophotometric and dyeing properties of some novel azo disperse dyes based on naphthalimides, Biotechnol. Prog. 31 (2015), 1086-1095. [16] A. Khosravi, K. Gharanjig, S. Moradian, M. Hosseinnezhad, A kinetic study on the dissolution of two naphthalimide based synthesized disperse dyestuffs in the presence of dispersing agents, Prog. Color Colorants Coat., 4 (2011), 107-112. [17] K. Gharanjig, Effect of additional hydroxyl groups on dissolution of azo dyes derived from N-carboxylic acid-1,8-naphthalimide in aqueous solutions containing various surface active agents, Prog. Color Colorants Coat., 6 (2013), 67-79. [18] M. Hosseinnezhad , S. Moradian, K. Gharanjig, Synthesis and Application of Two Organic Dyes for Dye-Sensitized Solar Cells, Prog. Color Colorants Coat., 6 (2013), 109-117. [19] S. Kinali-Demirci, S. Demirci, M. Kurt, Synthesis, structure characterization and antimicrobial evaluation of 4-(substituted phenylazo)-3,5-diacetamido-1H-pyrazoles, Spectrochim. Acta A Mol Biomol Spectrosc., 106 (2013), 12-18. [20] Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, Clinical and Laboratory Standards Institute, Approved Standard. 7th edn, 26, 14–16, 2006. [21] M. Okazaki, T. Tanaka, S. Taniguchi, Derivatives of 4-aminonaphthalimides, Yuki Gosei Kagaku Kyokai Shi., 14 (1956), 344-346. [22] A. Khosravi, S. Moradian, K. Gharanjig, F. Afshar Taromi, Synthesis and Characterization of Some Monoazo Disperse Dyestuffs Based on Naphthalimide Derivatives for Dyeing of Polyester Fabrics, J. Chin. Chem. Soc., 52 (2005), 495-502. [23] R. M. Christie, Fluorescent dyes, Rev. Prog. Coloration., 23 (1993), 1-18. [24] W.B. Hugo, The mode of action of antibacterial agents, J Appl Bacteriol., 30 (1967), 17–50. [25] J. Ninkovic1, V. Anand, R. Dutta, L. Zhang, A. Saluja, J. Meng, L. Koodie, S. Banerjee, S. Roy, Differential effects of gram-positive and gram-negative bacterial products on morphine induced inhibition of phagocytosis, Sci. Rep., 6 (2016), 1-16.


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