Investigation of Some Azo Dyes by QSAR Method and Acute Toxicity Test with Daphnia Magna

Öz

Azo dyes represent the most important class of textile dyes. Biotransformation of azo dyes can release aromatic amines. It is well known that some aromatic amines have genotoxic and/or carcinogenic properties. In this study, it was aimed to investigate the effects of azo dyes, which are composed of aromatic amines, and are widely used in the textile industry, on the environment using acute water toxicity test. The acute water toxicity test using Daphnia Magna was investigated experimentally and theoretically. The OECD QSAR Toolbox program, which has recently attracted attention in theoretical studies and is also used in international regulations, has been preferred. As a result of the studies, it was seen that the experimental and theoretical results gave parallel results. This study showed that theoretical studies can be substituted for experimental studies in order to reduce cost, time, and animal mortality in acute toxicity tests on Daphnia Magna. In addition, according to the results of this study, it was found by experimental and theoretical methods that Basic Yellow 28, Disperse Blue 291, and Disperse Brown 27-1 azo dye are ecotoxicologically toxic.

Anahtar Kelimeler

• Aromatic amines
• Azo Dyes
• QSAR
• Theoretical chemistry
• Daphnia Amgna
• Ecotoxicology

Bazı Azo Boyalarının QSAR Yöntemi ve Daphnia Magna ile Akut Toksisite Testi ile İncelenmesi

Öz

Azo boyalar, tekstil boyalarının en önemli sınıfını temsil eder. Azo boyaların biyotransformasyonu aromatik aminleri serbest bırakabilir. Bazı aromatik aminlerin genotoksik ve/veya kanserojen özelliklere sahip olduğu iyi bilinmektedir. Bu çalışmada, tekstil sektöründe yaygın olarak kullanılan aromatik aminlerden oluşan azo boyalarının çevre üzerindeki etkilerinin akut su toksisitesi testi ile araştırılması amaçlanmıştır. Daphnia Magna kullanılarak yapılan akut su toksisite testi deneysel ve teorik olarak incelenmiştir. Teorik çalışmalarda son zamanlarda ilgi gören ve ülkeler arası yönetmeliklerde de kullanılan OECD QSAR Toolbox programı tercih edilmiştir. Yapılan çalışmalar sonucunda deneysel ve teorik sonuçların paralel sonuçlar verdiği görülmüştür. Bu çalışma, Daphnia Magna üzerinde yapılan akut toksisite testlerinde maliyeti, süreyi ve hayvan ölümlerini azaltmak amacıyla teorik çalışmaların deneysel çalışmalara ikame olabileceğini göstermiştir. Ayrıca, bu çalışma sonuçlarına göre Basic Yellow 28, Dispers Blue 291 ve Dispers Brown 27-1 azo boyalarının ekotoksikolojik olarak toksik olduğu deneysel ve teorik yöntemler ile bulunmuştur

Anahtar Kelimeler

• Aromatik aminler
• Azo boyaları
• QSAR
• Teorik kimya
• Daphnia Magna
• Ekotoksikoloji

Kaynakça

1. Achwal, W.B. (1997). Problems during analysis of textile as per ecostandards and the customer articles ordinance (Part I). Colourage, 44(5), 29-31.
2. Bae, J.S. and Freeman, H.S. (2007). Aquatic toxicity evaluation of new direct dyes to the Daphnia Magna. Dyes and Pigments, 73(1), 81-85. DOI: 10.1016/j.dyepig.2005.10.015
3. Bae, J.S., Freeman, H.S., Kim, S.D. (2006). Influences of new azo dyes to the aquatic ecosystem. Fibers and polymers, 7, 30-35. DOI: 10.1007/BF02933599
4. Benigni, R. and Passerini, L. (2002). Carcinogenicity of the Aromatic Amines: From Structure-Activity Relationships to Mechanisms of Action and Risk Assessment. Mutation Research, 511(3), 191-206. DOI: 10.1016/s1383-5742(02)00008-x
5. Bulut, C., Çetinkaya, O., Kubilay, A., Akçimen, U., Ceylan, M. (2013). Acute Toxicity of Zinc (Cu+2) on Sand Smelt. Süleyman Demirel University Journal of Natural and Applied Science, 17(3), 32-38. DOI: 10.22392/actaquatr.874241
6. Brüschweiler, B.J. and Merlot, C. (2017). Azo Dyes In Clothing Textiles Can Be Cleaved Into A Series of Mutagenic Aromatic Amines Which Are Not Regulated Yet. Regulatory Toxicology and Pharmacology, 88, 214-226. DOI: 10.1016/j.yrtph.2017.06.012
7. Carliell, C.M., Barclay, S.J., Naidoo, N., Buckley, C.A., Mulholland, D.A., Senior, E. (1995). Microbial Decolourisation of A Reactive Azo Dye Under Anaerobic Conditions. Water SA, 21(1), 61-69.
8. Chung, K.T. (2016). Azo dyes and human health: A review. Part C: Environ. Carcinog. Ecotoxicol. Rev., 34, 233-261. DOI: 10.1080/10590501.2016.1236602

9. Correia, V.M., Stephenson, T., Judd, S.J. (1994). Characterisation of Textile Wastewaters ‐ A Review. Environmental Technology, 15, 917-929. DOI:10.1080/09593339409385500
10. Dimitrov, S.D., Diderich, R., Sobanski, T., Pavlov, T.S., Chankov, G.V., Chapkanov, A.S., Karakolev, Y.H., Temelkov, S.G., Vasilev, R.A., Gerova, K.D., Kuseva, C.D., Todorova, N.D., Mehmed, A.M., Rasenberg, M., Mekenyan, O.G. (2016). QSAR Toolbox – workflow and major functionalities. Environmental Research, 27(3), 203-219. DOI: 10.1080/1062936X.2015.1136680
11. Ekici, P., Leupol, G., Parlar, H. (2001). Degradability of selected azo dye metabolites in activated sludge systems. Chemosphere, 44(4), 721-728. DOI: 10.1016/S0045-6535(00)00345-3
12. Ferraz, E.R.A., Umbuzeiro, G.A., De Almeida, G., Caloto Oliveira, A., Chequer, F.M.D., Dorta, D.J., Oliveira, D.P. (2011). Differential toxicity of disperse red 1 and disperse red 13 in the Ames test, HepG2 cytotoxicity assay, and Daphnia acute toxicity test. Environ Toxicol., 26(5), 489–497. DOI: 10.1002/tox.20576
13. Hildenbrand, S., Schmahl, F.W., Wodarz, R., Kimmel, R., Dartsch, P.C. (1999). Azo Dyes and Carcinogenic Aromatic Amines in Cell Cultures. International Archives of Occupational and Environmental Health, 72, M052-M056.
14. Jaafarzadeh, N., Takdastan, A., Jorfi, S., Ghanbari, F., Ahmadi, M., Barzegar, G. (2018). The performance study on ultrasonic/Fe3O4/H2O2 for degradation of azo dye and real textile wastewater treatment. J. Mol. Liq., 256, 462-470. DOI: 10.1016/j.molliq.2018.02.047
15. Jarosz-wilkolazka, A., Kochmanska-Rdest, J., Malarczyk, E., Wardas, W., Leonowicz, A. (2002). Fungi and their ability to decolorize azo and anthraquinonic dyes. Enzyme and Microbial Technology, 30(4), 566-572. DOI: 10.1016/S0141-0229(02)00022-4
16. Jillella, G.K., Roy, K. (2021). QSAR modelling of organic dyes for their acute toxicity in Daphnia Magna using 2D-descriptors. SAR and QSAR in Environmental Research, 33(2), 111-139. DOI: 10.1080/1062936X.2022.2033318
17. Keşkek Karabulut, Y. (2020). Bazı Aromatik Aminlerin Toksikolojik Ve Ekotoksikolojik Özelliklerinin Qsar Yöntemi ile İncelenmesi. Doctoral Thesis, Institute of Science, Namık Kemal University, Tekirdağ, Türkiye.
18. Kuseva, C., Schultz, T.W., Yordanova, D., Tankova, K., Kutsarova, S., Pavlov, T., Chapkanov, A., Georgiev, M., Gissi, A., Sobanski, T., Mekenyan, O.G. (2019). The implementation of RAAF in the OECD QSAR Toolbox. Regulatory Toxicology and Pharmacology, 105, 51-61. DOI: 10.1016/j.yrtph.2019.03.018
19. Kutsarova, S., Schultz, T.W., Chapkanov, A., Cherkezova, D., Mehmed, A., Stoeva, S., Kuseva, C., Yordanova, D., Georgiev, M., Petkov, T., Mekenyan, O.G. (2021). The QSAR Toolbox Automated Read-across Workflow for Predicting Acute Oral Toxicity: II. Verification and Validation. Computational Toxicology, 20, 2468-1113. DOI: 10.1016/j.comtox.2022.100219
20. Majcen-Le, M.A., Slokar, Y.M., Taufer, T. (1997). Decoloration of chlorotriazine reactive azo dyes with H2O2/UV. Dyes Pigments, 33(4), 281-298. DOI:10.1016/S0143-7208(96)00057-5
21. Nam, S., Renganathan, V. (2000). Non enzymatic reduction of azo dyes by NADH. Chemosphere, 40(4), 351-357. DOI: 10.1016/S0045-6535(99)00226-X
22. OECD (2004). Test No. 202: Daphnia sp. acute immobilisation test. In OECD Guidelines for the Testing of Chemicals, OECD Publishing, Paris.
23. Ohe, T., Watanabe, T., Wakabayashi, K. (2004). Mutagens in Surface Waters: A Review. Mutation Research, 567(2-3), 109-149. DOI: 10.1016/j.mrrev.2004.08.003
24. Organization for Economic Cooperation and Development (OECD) (2020). Overview of Concepts and Available Guidance related to Integrated Approaches to Testing and Assessment (IATA). OECD Series on Testing and Assessment No. 329, OECD, Paris.
25. O’Neill, C., Hawkes, F.R., Hawkes, D.L., Lourenco, N.D., Pinheiro, H.M., Delée, W. (1999). Colour in textile effluents – sources, measurement, discharge consents, and simulation: a review. Journal of Chemical Technology and Biotechnology, 74(11), 1009-1018. DOI:10.1002/(SICI)1097-4660(199911)74:11<1009::AID-JCTB153>3.0.CO;2-N
26. Pearce, C.I., Lloyd, J.R., Guthrie, J.T. (2003). The removal of color from textile wastewater using whole bacterial cells: a review. Dyes and Pigments, 58(3), 179-196. DOI:10.1016/S0143-7208(03)00064-0
27. Pinheiro, H.M., Touraud, E., Thomas, O. (2004). Aromatic Amines from Azo Dye Reduction: Status Review with Emphasis on Direct UV Spectrophotometric Detection in Textile Industry Wastewaters. Dyes and Pigments, 61(2), 121–139. DOI: 10.1016/j.dyepig.2003.10.009
28. Puvaneswari, N., Muthukrishnan, J., Gunasekaran, P. (2006). Toxicity Assessment And Microbial Degradation Of Azo Dyes. Indian Journal of Experimental Biology, 44(8), 618-626. PMID: 16924831
29. Ramos, E.U., Vaal, M.A., Hermens, J.L.M. (2002). Interspecies Sensitivity in the Aquatic Toxicity of Aromatic Amines. Environmental Toxicology and Pharmacology, 11(3-4), 149-158. DOI:10.1016/s1382-6689(02)00004-2
30. Rawat, D., Mishra, V., Sharma, R.S. (2016). Detoxification of azo dyes in the context of environmental processes. Chemosphere, 155, 591-605. DOI: 10.1016/j.chemosphere.2016.04.068
31. Staples, C.A., Adams, W.J., Parkerton, T.F., Gorsuch, J.W., Biddinger, G.R., Reinert, K.H. (2009). Aquatic toxicity of eighteen phthalate esters. Environmental Toxicology and Chemistry, 16(5), 837-1086. DOI:10.1002/etc.5620160507
32. Umbuzeiro, G.A., Szymczyk, M., Li, M., Chen, Y., Vendemiatti, J.A.S., Albuquerque, A.F., Santos, A., Maselli, B.S., Kummrow, F., Vinueza, N.R., Freeman, H.S. (2017). Purification and characterization of three commercial phenylazoaniline disperse dyes. Coloration Technology, 133(6), 513-518. DOI: 10.1111/cote.12307
33. Umbuzeiro, G.A., Freeman, H.S., Warren, S.H., Oliveira, D.P., Terao, Y., Watanabe, T., Claxton, L.D. (2005). The contribution of azo dyes to the mutagenic activity of Cristais River. Chemosphere, 60(1), 55–64. DOI: 10.1016/j.chemosphere.2004.11.100
34. Umbuzeiro, G.A., Roubicek, D.A., Rech, C.M., Sato, M.I.Z., Claxton, L.D. (2004). Investigating the sources of the mutagenic activity found in a river using the Salmonella assay and different water extraction procedures. Chemosphere, 54(11), 1589–1597. DOI: 10.1016/j.chemosphere.2003.09.009
35. Umbuzeiro, G.A., Freeman, H., Warren, S.H., Kummrow, F., Claxton, L.D. (2005). Mutagenicity evaluation of the commercial product CI Disperse Blue 291 using different protocols of the Salmonella assay. Food and Chemical Toxicology, 43(1), 49-56. DOI: 10.1016/j.fct.2004.08.011
36. Vacchi, F.I., Albuquerque, A.F., Vendemiatti, J.A.S., Morales, D.A., Ormond, A.B., Freeman, H.S., Zocolo, G.J., Zanoni, M.V.B., Umbuzeiro, G.A. (2013). Chlorine disinfection of dye wastewater: Implications for a commercial azo dye mixture. Science of the Total Environment, 442, 302–309.DOI:10.1016/j.scitotenv.2012.10.019
37. Ventura-Camargo, B.C., Marin-Morales, M.A. (2013). Azo Dyes: Characterization and Toxicity A Review. Textiles and Light Industrial Science and Technology (TLIST), 2(2), 85-103.
38. Wexler, P. (2014). Encyclopedia of Toxicology, 3rd edn, US National Library of Medicine, Bethesda, MD, USA.