Login Register Cart 0
Generic placeholder image

Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1573-4064
ISSN (Online): 1875-6638

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Incorporating Antimicrobial Activity During Synthesis of New Acid-Azo Dyes: Thermal Stability and Application on Various Fabrics

Author(s): Ambreen Sarwar, Abdul Jabbar*, Saadia Riaz, Samina Parveen, Shafia Sagheer and Muhammad Iqbal Choudhary

Volume 19, Issue 9, 2023

Published on: 03 May, 2023

Page: [889 - 896] Pages: 8

DOI: 10.2174/1573406419666230331083942

Price: $65

Abstract

Background: Textile materials are susceptible to microbial attack as they provide suitable conditions for their growth. The microbes grow with normal body secretions on garments. These microbes are responsible for the weakening, brittleness, and discoloration of the substrate. Furthermore, they cause many health issues to the wearer, including dermal infection, bad odour etc. They threaten the human health as well as create tenderness in fabric.

Objectives: Usually, antimicrobial textiles are prepared by applying antimicrobial finishes after dyeing, which is an expensive approach. Concerning these adversities, in the present study, a series of antimicrobial acid-azo dyes have been synthesized by incorporating antimicrobial sulphonamide moiety into the dye molecules during its synthesis.

Methods: A commercially available sulphonamide-based compound, sulfadimidine Na-salt was used as a diazonium component and coupled with different aromatic amines to get desired dye molecules. Since dyeing and finishing are two separate energy-intensive processes, in the current research work, an approach to combine both processes in one step has been adopted that would be economical, timesaving, and environment friendly. Structures of the resultant dye molecules have been confirmed using different spectral techniques such as Mass spectrometry, 1H-NMR spectroscopy, FT-IR, and UV-Visible spectroscopy.

Results: Thermal stability of the synthesized dyes was also determined. These dyes have been applied to wool and nylon-6 fabrics. Their various fastness properties were examined using ISO standard methods.

Conclusion: All the compounds exhibited good to excellent fastness properties. The synthesized dyes and the dyed fabrics were screened biologically against Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 10536, resulting in significant antibacterial activities.

« Previous Next »
Graphical Abstract

[1]
Oda, H. An approach to the photostabilization of dyes: the effect of UV absorbers containing a built-in photostabilizer moiety on the light fastness of acid dyes. Dyes Pigments, 2001, 48(2), 151-157.
[http://dx.doi.org/10.1016/S0143-7208(00)00096-6]
[2]
Singh, R.; Jain, A.; Panwar, S.; Gupta, D.; Khare, S.K. Antimicrobial activity of some natural dyes. Dyes Pigments, 2005, 66(2), 99-102.
[http://dx.doi.org/10.1016/j.dyepig.2004.09.005]
[3]
Ketema, A.; Worku, A. Antibacterial finishing of cotton fabric using stinging nettle (Urtica dioica L.) plant leaf extract. J. Chem., 2020, 2020, 1-10.
[http://dx.doi.org/10.1155/2020/4049273]
[4]
Kumar, P.S.; Jayanthi, B.; Abdul, K.; Prasad, U.; Kumar, Y.N.; Sarma, P. A validated High Performance Liquid Chromatography (HPLC) method for the estimation of cefuroxime axetil. Res. J. Pharm. Biol. Chem. Sci., 2012, 3(2), 752-761.
[5]
Mirjalili, M.; Karimi, L. Extraction and characterization of natural dye from green walnut shells and its use in dyeing polyamide: focus on antibacterial properties. J. Chem., 2013, 2013, 1-9.
[http://dx.doi.org/10.1155/2013/375352]
[6]
Sekar, N. Advances in the Dyeing and Finishing of Technical Textiles; Gulrajani, M.L., Ed.; Woodhead Publishing in Series of Textile: India, 2013, pp. 47-77.
[http://dx.doi.org/10.1533/9780857097613.1.47]
[7]
Park, S. H. Antibacterial acid dyes and method of preparing the same and antibacterial fiber dyed thereby. Patent: W02006091024A1, 2008.
[8]
Hebeish, A.; El-Naggar, M.E.; Fouda, M.M.G.; Ramadan, M.A.; Al-Deyab, S.S.; El-Rafie, M.H. Highly effective antibacterial textiles containing green synthesized silver nanoparticles. Carbohydr. Polym., 2011, 86(2), 936-940.
[http://dx.doi.org/10.1016/j.carbpol.2011.05.048]
[9]
Kiwi, J.; Pulgarin, C. Innovative self-cleaning and bactericide textiles. Catal. Today, 2010, 151(1-2), 2-7.
[http://dx.doi.org/10.1016/j.cattod.2010.01.032]
[10]
Maria, S.G.; Anca, D.; Elena, G.M.; Germaine, S.; Mihaiela, A.; Gianina, B. Azo compounds with antimicrobial activity. Afr. J. Microbiol. Res., 2010, 4(8), 618-625.
[11]
Abedi, D.; Mortazavi, S.M.; Mehrizi, M.K.; Feiz, M. Antimicrobial properties of acrylic fabrics dyed with direct dye and a copper salt. Text. Res. J., 2008, 78(4), 311-319.
[http://dx.doi.org/10.1177/0040517508090486]
[12]
Sayed, A.Z.; El-Gaby, M.S.A. Synthesis of novel dyestuffs containing sulphonamido moieties and their application on wool and polyamide fibres. Color. Technol., 2001, 117(5), 293-297.
[http://dx.doi.org/10.1111/j.1478-4408.2001.tb00078.x]
[13]
Zani, F.; Vicini, P. Antimicrobial activity of some 1,2-benzisothiazoles having a benzenesulfonamide moiety. Arch. Pharm., 1998, 331(6), 219-223.
[http://dx.doi.org/10.1002/(SICI)1521-4184(199806)331:6<219:AID-ARDP219>3.0.CO;2-U] [PMID: 9713255]
[14]
Li, J.J.; Anderson, G.D.; Burton, E.G.; Cogburn, J.N.; Collins, J.T.; Garland, D.J.; Gregory, S.A.; Huang, H.C.; Isakson, P.C.; Koboldt, C.M. 1,2-Diarylcyclopentenes as selective cyclooxygenase-2 inhibitors and orally active anti-inflammatory agents. J. Med. Chem., 1995, 38(22), 4570-4578.
[http://dx.doi.org/10.1021/jm00022a023] [PMID: 7473585]
[15]
Jabbar, A. Ambreen; Riaz, S.; Navaid, F.A.; Choudhary, M.I. A series of new acid dyes; study of solvatochromism, spectroscopy and their application on wool fabric. J. Mol. Struct., 2019, 1195, 161-167.
[http://dx.doi.org/10.1016/j.molstruc.2019.05.019]
[16]
Riaz, S. Ambreen; Navaid, F.A.; Choudhary, M.I.; Jabbar, A. Synthesis, characterization, solvatochromic study, and application of new heterocyclic monoazo acid dyes. J. Mol. Liq., 2019, 287, 110917.
[http://dx.doi.org/10.1016/j.molliq.2019.110917]
[17]
Aspland, J.R. Textile Dyeing and Coloration AATCC Textile Chemist and Colorist; Research Triangle Park, North Carolina, 1997.
[18]
Shore, J. Colorants and Auxiliaries, 2nd ed; Society of Dyers and Colorants: London, 2002.
[19]
Gordon, P.F.; Gregory, P. Organic Chemistry in Colour; Springer: Berlin, 2012.
[20]
Zollinger, H. Color Chemistry: Synthesis, Properties, and Applications of Organic Dyes and Pigments, 3rd ed; John Wiley and Sons: Weinheim, 2003.
[21]
Gaffer, H.E.; Mohamed, M.E.; Zahran, M.K. Synthesis of some novel antibacterial sulfonamide reactive dyes. Life Sci., 2014, 11(11), 138-142.
[22]
Ibrahim, N.A. Handbook of Textile and Industrial Dyeing; Clark, M., Ed.; Elsevier: Amsterdam, 2011, 2, pp. 147-172.
[http://dx.doi.org/10.1533/9780857094919.1.147]
[23]
Awad, I.M.A. Heterocyclo-substituted sulfa drugs: Part XI. Novel biologically active N-(piperidino-, morpholino-, piperazino-) dithiocarbamyl-azo dyes and their chelates. Phosphorus Sulfur Silicon Relat. Elem., 2000, 163(1), 219-251.
[http://dx.doi.org/10.1080/10426500008046622]
[24]
Shah, M.R.; Ali, S.; Ateeq, M.; Perveen, S.; Ahmed, S.; Bertino, M.F.; Ali, M. Morphological analysis of the antimicrobial action of silver and gold nanoparticles stabilized with ceftriaxone on Escherichia coli using atomic force microscopy. New J. Chem., 2014, 38(11), 5633-5640.
[http://dx.doi.org/10.1039/C4NJ00751D]
[25]
Erdem, A.K. Yürüdü, N.Ö.Ş. The evaluation of antibacterial activity of fabrics impregnated with dimethyltetradecyl (3-(trimethoxysilyl) propyl) ammonium chloride. IUFS J. Biol., 2008, 67(2), 115-122.
[26]
Akhtar, Z.; Ali, S.I.; Abbas, N.; Ali, M.; Khan, M.Y.; Hasan, S.A.; Ahmed, S.; Manzoor, S.; Lutfi, Z. Evaluation of antibacterial potential of new acid dyes based on substituted aryl amines and amino hydroxy sulfonic acid. J. Chem. Pak., 2020, 42(5), 783-788.
[27]
Verma, S.K.; Verma, R.; Xue, F.; Thakur, P.K.; Girish, Y.R.; Rakesh, K.P. Antibacterial activities of sulfonyl or sulfonamide containing heterocyclic derivatives and its Structure-Activity Relationships (SAR) studies: A critical review. Bioorg Chem, 2020, 105, 104400.
[http://dx.doi.org/10.1016/j.bioorg.2020.104400]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy