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INVESTIGATION OF TOXICOLOGICAL PROPERTIES OF SOME AZO DYES BY OECD QSAR METHOD

Year 2023, , 1 - 22, 30.06.2023
https://doi.org/10.34186/klujes.1242876

Abstract

In this study, the toxicological properties of some of the aromatic amine raw materials commonly used in textile dyes and the dyestuffs produced from these raw materials were examined with the OECD QSAR method and their toxicological effects on human health were investigated. In the literature review conducted with the relevant structures, it was seen that no study set was found in terms of toxicology, considering the comparison of raw materials and products.
Studies have found that some aromatic amine raw materials and azo dyes produced from these raw materials are generally moderately irritating. While the related raw materials generally have eye irritant properties, the products do not have any irritating properties. It can be said that 12 aromatic amine raw materials and 13 azo dyes have skin sensitizing properties. The raw materials are 2,6-dibromo-4-nitro aniline, 6-methoxybenzothiazole-2-ylamine, 2-Bromo-4,6-dinotroaniline, and azo dyes, which are Disperse Brown 27-1, Disperse Brown 19 and Disperse Blue 291, are mutagenic.

Supporting Institution

SETAS Kimya San. A.Ş. R&D Center Ministry Projects

Project Number

BY18-0005

References

  • Keşkek Karabulut, Y. and Yalçın Gürkan, Y., Investigation of Ecotoxicological Properties of Some Azo Dyes by OECD QSAR Method. Journal Of Materials and Electronic Devices, 3(1), 27, 2022.
  • Majcen-Le Marechal, A., Slokar, Y.M., and Taufer, T., Decoloration of Chlorotriazine Reactive Azo Dyes with H2O2/UV. Dyes and Pigments, 33(4), 281, 1997.
  • Puvaneswari, N., Muthukrishnan, J., Gunasekaran, P., Toxicity Assessment And Microbial Degradation Of Azo Dyes. Indian J Exp Biol, 44(8), 618, 2006.
  • Weisburger, J.H., A perspective on the history and significance of carcinogenic and Mutagenic N-substituted aryl compounds in human health. Mutation Research, 376, 261, 1997.
  • Lin, Y.H., Leu, J.Y., Kinetics of reactive azo-dye decolorization by Pseudomonas luteola in a biological activated carbon process. Biochemical Engineering Journal, 39(3), 457, 2008.
  • Lin, J.K., Wu, Y.H., Studies on the mechanism of methemoglobin formation induced by amino azo compounds. Biochemistry Pharmacology, 22(15), 1883, 1973.
  • Pielesz, A., Baranowska, I., Rybak, A., Włochowicz, A., Detection and Determination of Aromatic Amines as Products of Reductive Splitting from Selected Azo Dyes. Ecotoxicology and Environmental Safety, 53(1), 42, 2002.
  • Choudhary, G., Human health perspectives on environmental exposure to benzidine: a review. Chemosphere, 32(2), 267, 1996.
  • Benigni, R., Passerini, L., Carcinogenicity of the aromatic amines: from structure-activity relationships to mechanisms of action and risk assessment. Mutation Research, 511 (3), 191, 2002.
  • Pinheiro, H.M., Touraud, E., Thomas, O., Aromatic amines from azo dye reduction: a status review with emphasis on direct UV spectrophotometric detection in textile industry wastewaters. Dyes and Pigments, 61(2), 121, 2004.
  • Petry, T., Knowles, R., Meads, R., An analysis of the proposed REACH regulation. Regulatory Toxicology and Pharmacology, 44 (1), 24, 2006.
  • European Parliament (EC) No. Regulation 1907/2006 on the Registration, Evaluation, Authorization, and Restriction of Chemicals (REACH).
  • 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., QSAR Toolbox – workflow and major functionalities. Environmental Research, 27 (3), 203, 2016.
  • Saouter, E., Biganzoli, F., Pant, R., Sala, S., Versteeg, D., Using REACH for the EU environmental footprint: building a usable ecotoxicity database, part I. Integrated Environmental Assessment and Management, 15(5), 783, 2019. Basketter, D.A.; Andersen, K.E.; Liden, C.; Van Loveren, H.; Boman, A.; Kimber, I.; Alanko, K.; Berggren, E., Evaluation of the skin sensitizing potency of chemicals by using the existing methods and considerations of relevance for elicitation. Contact Dermatitis, 52 (1), 39, 2005.
  • Alves, V.M.; Muratov, E.; Fourches, D.; Strickland, J.; Kleinstreuer, N.; Andrade, C.H.; Tropsha, A., Predicting chemically-induced skin reactions. Part I: QSAR models of skin sensitization and their application to identify potentially hazardous compounds. Toxicol. Appl. Pharmacol., 284 (2), 262, 2015.
  • Sarı, S., Bazı yeni 2-Sübstitüe benzotiyazol türevlerinin ames test sistemi ile mutajenik etkilerinin belirlenmesi. Master's Thesis, Yüksek Lisans Tezi, Institute of science, Hacettepe University, Ankara, Türkiye, 2014.
  • Oğuz, S., Omurtag, G.Z., Arıcıoğlu, F., Şardaş, S. Mutajenik Karsinojen Etkinin Ames Testi ile Araştırılması. Müsbed, 3 (2), 75, 2013.
  • Nartop, D., Demirel, B., Güleç, M., Hasanoğlu Özkan, E., Kurnaz Yetim, N., Sarı, N., Çeker, S., Öğütçü, H., Ağar, G. Novel polymeric microspheres: Synthesis, enzyme immobilization, antimutagenic activity, and antimicrobial evaluation against pathogenic microorganisms. Journal of Biochemical anda Molecular Toxicology, 34(2), 2019.
  • Nartop, D., Hasanoğlu Özkan, E., Gündem, M., Çeker, S., Ağar, G., Öğütçü, H., Sarı, N. Synthesis, antimicrobial and antimutagenic effects of novel polymeric-Schiff bases including indol. Journal of Molecular Structure, 1195, 877,2019.
  • Nartop, D., Tokmak, E., Hasanoğlu Özkan, E., Kızıl, H. E., Öğütcü, H., Ağar, G., Allı, S. Synthesis of novel polymers containing Schiff base as potential antimutagenic and antimicrobial agents. Journal of Medicinal and Chemical Sciences, 3(4), 363, 2020.

Bazı Azo Boyaların Toksikolojik Özelliklerinin OECD QSAR Yöntemiyle Araştırılması

Year 2023, , 1 - 22, 30.06.2023
https://doi.org/10.34186/klujes.1242876

Abstract

Bu çalışmada tekstil boyalarında yaygın olarak kullanılan bazı aromatik amin hammaddelerin ve bu hammaddelerden üretilen boyarmaddelerin toksikolojik özellikleri OECD QSAR yöntemi ile incelenmiş ve insan sağlığı üzerindeki toksikolojik etkileri araştırılmıştır. İlgili yapılarla yapılan literatür taramasında, hammadde ve ürün karşılaştırmasına bakıldığında toksikolojik açıdan herhangi bir çalışma setine rastlanmadığı görülmüştür.
Yapılan araştırmalarda bazı aromatik amin hammaddelerin ve bu hammaddelerden üretilen azo boyaların genel olarak orta derecede tahriş edici olduğunu bulunmuştur. İlgili hammaddeler genel olarak gözü tahriş edici özelliğe sahipken, ürünlerde herhangi bir tahriş edici özellik bulunmamaktadır. 12 aromatik amin hammaddenin ve 13 azo boyasının cildi hassaslaştırıcı özelliği olduğu söylenebilir. Hammaddeler, 2,6-dibromo-4-nitro anilin, 6-methoxybenzothiazole-2-ylamine, 2-Bromo-4,6-dinotroanilin ve bu hammaddelerden üretilen Dispers Brown 27-1, Dispers Brown 19 ve Dispers Blue 291 azo boyaları mutajeniktir.

Project Number

BY18-0005

References

  • Keşkek Karabulut, Y. and Yalçın Gürkan, Y., Investigation of Ecotoxicological Properties of Some Azo Dyes by OECD QSAR Method. Journal Of Materials and Electronic Devices, 3(1), 27, 2022.
  • Majcen-Le Marechal, A., Slokar, Y.M., and Taufer, T., Decoloration of Chlorotriazine Reactive Azo Dyes with H2O2/UV. Dyes and Pigments, 33(4), 281, 1997.
  • Puvaneswari, N., Muthukrishnan, J., Gunasekaran, P., Toxicity Assessment And Microbial Degradation Of Azo Dyes. Indian J Exp Biol, 44(8), 618, 2006.
  • Weisburger, J.H., A perspective on the history and significance of carcinogenic and Mutagenic N-substituted aryl compounds in human health. Mutation Research, 376, 261, 1997.
  • Lin, Y.H., Leu, J.Y., Kinetics of reactive azo-dye decolorization by Pseudomonas luteola in a biological activated carbon process. Biochemical Engineering Journal, 39(3), 457, 2008.
  • Lin, J.K., Wu, Y.H., Studies on the mechanism of methemoglobin formation induced by amino azo compounds. Biochemistry Pharmacology, 22(15), 1883, 1973.
  • Pielesz, A., Baranowska, I., Rybak, A., Włochowicz, A., Detection and Determination of Aromatic Amines as Products of Reductive Splitting from Selected Azo Dyes. Ecotoxicology and Environmental Safety, 53(1), 42, 2002.
  • Choudhary, G., Human health perspectives on environmental exposure to benzidine: a review. Chemosphere, 32(2), 267, 1996.
  • Benigni, R., Passerini, L., Carcinogenicity of the aromatic amines: from structure-activity relationships to mechanisms of action and risk assessment. Mutation Research, 511 (3), 191, 2002.
  • Pinheiro, H.M., Touraud, E., Thomas, O., Aromatic amines from azo dye reduction: a status review with emphasis on direct UV spectrophotometric detection in textile industry wastewaters. Dyes and Pigments, 61(2), 121, 2004.
  • Petry, T., Knowles, R., Meads, R., An analysis of the proposed REACH regulation. Regulatory Toxicology and Pharmacology, 44 (1), 24, 2006.
  • European Parliament (EC) No. Regulation 1907/2006 on the Registration, Evaluation, Authorization, and Restriction of Chemicals (REACH).
  • 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., QSAR Toolbox – workflow and major functionalities. Environmental Research, 27 (3), 203, 2016.
  • Saouter, E., Biganzoli, F., Pant, R., Sala, S., Versteeg, D., Using REACH for the EU environmental footprint: building a usable ecotoxicity database, part I. Integrated Environmental Assessment and Management, 15(5), 783, 2019. Basketter, D.A.; Andersen, K.E.; Liden, C.; Van Loveren, H.; Boman, A.; Kimber, I.; Alanko, K.; Berggren, E., Evaluation of the skin sensitizing potency of chemicals by using the existing methods and considerations of relevance for elicitation. Contact Dermatitis, 52 (1), 39, 2005.
  • Alves, V.M.; Muratov, E.; Fourches, D.; Strickland, J.; Kleinstreuer, N.; Andrade, C.H.; Tropsha, A., Predicting chemically-induced skin reactions. Part I: QSAR models of skin sensitization and their application to identify potentially hazardous compounds. Toxicol. Appl. Pharmacol., 284 (2), 262, 2015.
  • Sarı, S., Bazı yeni 2-Sübstitüe benzotiyazol türevlerinin ames test sistemi ile mutajenik etkilerinin belirlenmesi. Master's Thesis, Yüksek Lisans Tezi, Institute of science, Hacettepe University, Ankara, Türkiye, 2014.
  • Oğuz, S., Omurtag, G.Z., Arıcıoğlu, F., Şardaş, S. Mutajenik Karsinojen Etkinin Ames Testi ile Araştırılması. Müsbed, 3 (2), 75, 2013.
  • Nartop, D., Demirel, B., Güleç, M., Hasanoğlu Özkan, E., Kurnaz Yetim, N., Sarı, N., Çeker, S., Öğütçü, H., Ağar, G. Novel polymeric microspheres: Synthesis, enzyme immobilization, antimutagenic activity, and antimicrobial evaluation against pathogenic microorganisms. Journal of Biochemical anda Molecular Toxicology, 34(2), 2019.
  • Nartop, D., Hasanoğlu Özkan, E., Gündem, M., Çeker, S., Ağar, G., Öğütçü, H., Sarı, N. Synthesis, antimicrobial and antimutagenic effects of novel polymeric-Schiff bases including indol. Journal of Molecular Structure, 1195, 877,2019.
  • Nartop, D., Tokmak, E., Hasanoğlu Özkan, E., Kızıl, H. E., Öğütcü, H., Ağar, G., Allı, S. Synthesis of novel polymers containing Schiff base as potential antimutagenic and antimicrobial agents. Journal of Medicinal and Chemical Sciences, 3(4), 363, 2020.
There are 20 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Issue
Authors

Yasemin Keşkek Karabulut 0000-0002-6742-783X

Yelda Yalçın Gürkan 0000-0002-6316-5510

Project Number BY18-0005
Publication Date June 30, 2023
Published in Issue Year 2023

Cite

APA Keşkek Karabulut, Y., & Yalçın Gürkan, Y. (2023). INVESTIGATION OF TOXICOLOGICAL PROPERTIES OF SOME AZO DYES BY OECD QSAR METHOD. Kirklareli University Journal of Engineering and Science, 9(1), 1-22. https://doi.org/10.34186/klujes.1242876