DETERMINATION OF PHYSICOCHEMICAL AND TOXICOLOGICAL PROPERTIES OF AZO DYES USING IN SILICO METHODS

Gülendam Pirinççi; Şimal Kürümoğlu

doi:10.17780/ksujes.1811220

TR EN

IN SILICO YÖNTEMLERİ KULLANILARAK AZO BOYALARIN FİZİKOKİMYASAL VE TOKSİKOLOJİK ÖZELLİKLERİNİN BELİRLENMESİ

Öz

Bu çalışmada, Dispers Black 9 ve Mordant Black 9 azo boyaları teorik araştırmanın konusu olmuştur. Boyaların karakterizasyonu, Yoğunluk Fonksiyonel Teorisi (DFT) yöntemi kullanılarak incelenmiştir. Moleküller optimize edilmiş ve enerji seviyeleri B3LYP teori seviyesi ve 6-311++G(d,p) temel seti kullanılarak hesaplanmıştır. Sonuç olarak, en yüksek dolu moleküler orbitalin (EHOMO) enerjisini ve en düşük boş moleküler orbitalin (ELUMO) enerjisini tahmin etmek için sınır moleküler orbital (FMO) kullanılmıştır. Ayrıca, HOMO–LUMO enerji aralığı değerleri de dahil olmak üzere, küresel sertlik, küresel yumuşaklık, elektronik kimyasal potansiyel, elektrofilik indeks, elektronegatiflik, moleküler elektrostatik potansiyeller, iyonlaşma enerjisi ve elektron afinitesi gibi küresel reaktivite tanımlayıcı değerleri hesaplanmıştır. Aynı zamanda, boyaların toksikolojik ve ADMET özellikleri hesaplandı. Bu değerler hesaplanarak, azo boyaların insan sağlığı ve çevre üzerindeki potansiyel etkileri karşılaştırıldı. Verilerin toplanması için ProTox 3.0, ToxTree, ECOSAR ve T.E.S.T. gibi bilgisayar tabanlı in silico programlar kullanılmıştır. Moleküler modelleme yöntemleri verimliliği artırmış, zamandan tasarruf sağlamış, maliyetleri düşürmüş ve daha hızlı sonuçlar elde edilmesini sağlamıştır. Bu çalışma, araştırmacılara çevre ve su kirliliğine neden olan kirleticilerin özellikleri ve toksisitesi hakkında bilgi vermeyi amaçlamaktadır.

Anahtar Kelimeler

DETERMINATION OF PHYSICOCHEMICAL AND TOXICOLOGICAL PROPERTIES OF AZO DYES USING IN SILICO METHODS

Abstract

In this study, Disperse Black 9 and Mordant Black 9 azo dyes were the objects of theoretical research. The characterization of the dyes was studied using the Density Functional Theory (DFT) method. The molecules were optimized, and their energy levels were calculated using the B3LYP theory level and the 6-311++G(d,p) basis set. Consequently, the frontier molecular orbital (FMO) was utilized to estimate the energy of the highest occupied molecular orbital (EHOMO) and the energy of the lowest unoccupied molecular orbital (ELUMO). Furthermore, global reactivity descriptor values such as global hardness, global softness, electronic chemical potential, electrophilic index, electronegativity, molecular electrostatic potentials, ionization energy, and electron affinity were calculated, including the values of the HOMO–LUMO energy gap. Concurrently, the toxicological and ADMET properties of the dyes were calculated. By calculating these values, the potential effects of azo dyes on human health and the environment were compared. Computer-based in silico programs such as ProTox 3.0, ToxTree, ECOSAR, and T.E.S.T. were used to collect the data. Molecular modeling methods have increased efficiency, saving time, reducing costs, and providing faster results. This study aims to inform researchers about the properties and toxicity of pollutants causing environmental and water pollution.

Keywords

Kaynakça

Adekoya, O. C., Adekoya, G. J., Sadiku, E. R., Hamam, Y., & Ray, S. S. (2022). Application of DFT Calculations in Designing Polymer-Based Drug Delivery Systems: An Overview. Pharmaceutics, 14(9). https://doi.org/10.3390/pharmaceutics14091972
Al Prol, A. E. (2019). Study of Environmental Concerns of Dyes and Recent Textile Effluents Treatment Technology: A Review. Asian Journal of Fisheries and Aquatic Research, 1-18. https://doi.org/10.9734/ajfar/2019/v3i230032
Al-Ghouti, M. A., & Sweleh, A. O. (2019). Optimizing textile dye removal by activated carbon prepared from olive stones. Environmental Technology & Innovation, 16, 100488. https://doi.org/10.1016/j.eti.2019.100488
Arnot, J. A., & Gobas, F. A. (2006). A generic QSAR for assessing the bioaccumulation potential of organic chemicals in aquatic food webs. Environmental Toxicology and Chemistry, 25(9), 2346-2355
Bhatia, S., Schultz, T., Roberts, D., Shen, J., Kromidas, L., & Api, A. M. (2015). Comparison of Cramer classification between Toxtree, the OECD QSAR Toolbox and expert judgment. Regulatory Toxicology and Pharmacology, 71(1), 52-62. https://doi.org/10.1016/j.yrtph.2014.11.005
Bicheng, Z., Cheng, B., Zhang, L., & Yu, J. (2019). Review on DFT calculation of s‐triazine‐based carbon nitride. Carbon Energy, 1. https://doi.org/10.1002/cey2.1
Bukola M Adesanmi, Yung-Tse Hung, Paul, H. H., & Huhnke, C. R. (2022). Comparison of dye wastewater treatment methods: A review. https://doi.org/10.5281/ZENODO.6331586
Contrera, J. F. (2013). Validation of Toxtree and SciQSAR in silico predictive software using a publicly available benchmark mutagenicity database and their applicability for the qualification of impurities in pharmaceuticals. Regulatory Toxicology and Pharmacology, 67(2), 285-293. https://doi.org/10.1016/j.yrtph.2013.08.008

Chung, K. T., & Cerniglia, C. E. (1992). Mutagenicity of azo dyes: Structure-activity relationships. Mutation Research/Reviews in Genetic Toxicology, 277(3), 201-220
ECOSAR. https://www.epa.gov/tsca-screening-tools/ecological-structure-activity-relationships-ecosar-predictive-model
Frisch, M. (2009). gaussian 09, Revision d. 01, Gaussian. Inc, Wallingford CT, 201
Frydrych, A., & Jurowski, K. (2024). The comprehensive prediction of carcinogenic potency and tumorigenic dose (TD50) for two problematic N-nitrosamines in food: NMAMPA and NMAMBA using toxicology in silico methods. Chemico-Biological Interactions, 389, 110864. https://doi.org/10.1016/j.cbi.2024.110864
Gita, S., Hussan, A., & Choudhury, T. G. (2017). Impact of Textile Dyes Waste on Aquatic Environments and its Treatment
Hansch, C., & Leo, A. (1995). Exploring QSAR: Fundamentals and Applications in Chemistry and Biology. Washington, DC: American Chemical Society
Jurowski, K., & Kobylarz, D. (2025). Toxicity assessment of the novel psychoactive substance HU-210 (Hebrew University 210; CAS: 112830–95-2): First insight into toxicophores and critical toxicity parameters (acute toxicity, health effects, genotoxicity, skin and eye irritation, cardiotoxicity and endocrine disruption) using in silico methods for applications in clinical and forensic toxicology. Toxicology Letters, 410, 39-57. https://doi.org/10.1016/j.toxlet.2025.05.012
Karaçıray, E. (2019). Tekstil atık sularından farklı özellikteki boyar maddelerin membran biyoreaktör (MBR) sistemindeki arıtımı. Yüksek Lisans Tezi. Bilecik: Bilecik Şeyh Edebali Üniversitesi, Fen Bilimleri Enstitüsü.
Katheresan, V., Kansedo, J., & Lau, S. Y. (2018). Efficiency of various recent wastewater dye removal methods: A review. Journal of Environmental Chemical Engineering, 6(4), 4676-4697. https://doi.org/10.1016/j.jece.2018.06.060
Kaya Kınaytürk, N. (2023). Bromukonazol’ ün Moleküler Etkileşim Mekanizmasının DFT ve Moleküler Kenetleme Yöntemleri İle Açıklanması. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 27(2), 266-272. https://doi.org/10.19113/sdufenbed.1213761
Kocaer, F. O., & Alkan, U. (2002). Boyar madde içeren tekstil atıksularının arıtım alternatifleri. Uludağ Üniversitesi Mühendislik-Mimarlık Fakültesi Dergisi, 7(1).
Liao, J., Xu, F., Cheng, H., Liu, Y., Zhang, R., Cheng, W., & Duan, N. (2024). An efficient measure for controlling pollution in the dye industry: Experimental and DFT investigations on direct determination of 3-(N,N-diethylamino)acetanilide. Journal of Cleaner Production, 466, 142872. https://doi.org/10.1016/j.jclepro.2024.142872
Liu, H., Cheng, L., Hu, Y., Chen, D., Wang, X., Zhang, X., Li, Z., & Wu, Z. (2024). Hepatotoxicity of oral exposure to 2-methyl-4-nitroaniline: Toxicity prediction and in vivo evaluation. Toxicology Letters, 399, 1-8. https://doi.org/10.1016/j.toxlet.2024.07.002
Meyland, W.M., Howard, P.H., 1998. User’s Guide for the ECOSAR Class Program. USEPA, North Syracuse, New York, USA
Myatt, G. J., Ahlberg, E., Akahori, Y., Allen, D., Amberg, A., Anger, L. T., Aptula, A., Auerbach, S., Beilke, L., Bellion, P., Benigni, R., Bercu, J., Booth, E. D., Bower, D., Brigo, A., Burden, N., Cammerer, Z., Cronin, M. T. D., Cross, K. P., … Hasselgren, C. (2018). In silico toxicology protocols. Regulatory Toxicology and Pharmacology, 96, 1-17. https://doi.org/10.1016/j.yrtph.2018.04.014
Ngo, A. C. R., & Tischler, D. (2022). Microbial Degradation of Azo Dyes: Approaches and Prospects for a Hazard-Free Conversion by Microorganisms. International Journal of Environmental Research and Public Health, 19(8). https://doi.org/10.3390/ijerph19084740
Niżnik, Ł., Jabłońska, K., Orczyk, M., Orzechowska, M., Toporowska-Kaźmierak, J., Sowińska, M., Jasińska, J., & Jurowski, K. (2024). Toxicity of New Psychoactive Substance (NPS): Threo-4-methylmethylphenidate (4-Mmph) – Prediction of toxicity using in silico methods. Toxicology in Vitro, 99, 105891. https://doi.org/10.1016/j.tiv.2024.105891
Noga, M., & Jurowski, K. (2025). Reexamining the acute toxicity of chloropicrin: Comprehensive estimation using in silico methods. Toxicology in Vitro, 105, 106033. https://doi.org/10.1016/j.tiv.2025.106033
Omar, A. Z., Mohamed, M. G., Hamed, E. A., & El-atawy, M. A. (2023). Characterization, DFT calculations and dyeing performance on polyester fabrics of some azo disperse dyes containing pyrazole ring. Journal of Saudi Chemical Society, 27(1), 101594. https://doi.org/10.1016/j.jscs.2022.101594
Ölmez, T. (1999). Tekstil endüstrisinde reaktif boya banyolarında ozon ile renk giderimi. Yüksek Lisans Tezi. İstanbul: İstanbul Teknik Üniversitesi, Fen Bilimleri Enstitüsü
Parr, R. G., & Pearson, R. G. (1983). Absolute hardness: companion parameter to absolute electronegativity. Journal of the American Chemical Society, 105(26), 7512-7516
Pearson, R. G. (1963). Hard and soft acids and bases. Journal of the American Chemical Society, 85(22), 3533-3539
Pinheiro, H. M., Touraud, E., & Thomas, O. (2004). Aromatic amines from azo dye reduction: status and perspectives. Water Research, 38(9), 2305-2317 ProTox 3.0. https://tox.charite.de/protox3/#.
Sanderson, H., Johnson, D. J., Wilson, C. J., Brain, R. A., & Solomon, K. R. (2003). Probabilistic hazard assessment of environmentally occurring pharmaceuticals toxicity to fish, daphnids and algae by ECOSAR screening. Toxicology Letters, 144(3), 383-395. https://doi.org/10.1016/S0378-4274(03)00257-1
Sardi, F. K. G., Behpour, M., Ramezani, Z., & Masoum, S. (2021). Simultaneous removal of Basic Blue41 and Basic Red46 dyes in binary aqueous systems via activated carbon from palm bio-waste: Optimization by central composite design, equilibrium, kinetic, and thermodynamic studies. Environmental Technology & Innovation, 24, 102039. https://doi.org/10.1016/j.eti.2021.102039
Sneha, P., Keerthikumar, C. T., Ramyakumari, C. T., & Nirupanandaswamy. (2025). Synthesis and Characterization of Sulfadiazine Azo Dyes: Electrochemical and Photophysical Properties. Results in Surfaces and Interfaces, 100475. https://doi.org/10.1016/j.rsurfi.2025.100475
Sokolowska-Gajda, J., Freeman, H. S., & Reife, A. (1996). Synthetic dyes based on environmental considerations. Part 2: Iron complexes for protein fibers. Dyes and Pigments, 30(1), 1-20
Song, P. N., Mahy, J. G., Farcy, A., Calberg, C., Fagel, N., & Lambert, S. D. (2024). Development of novel composite materials based on kaolinitic clay modified with ZnO for the elimination of azo dyes by adsorption in water. Results in Surfaces and Interfaces, 16, 100255. https://doi.org/10.1016/j.rsurfi.2024.100255 TEST. https://www.epa.gov/comptox-tools/toxicity-estimation-software-tool-test. Toxtree. https://apps.ideaconsult.net/data/ui/toxtree.
Ukaogo, P. O., Ewuzie, U., & Onwuka, C. V. (2020). 21—Environmental pollution: Causes, effects, and the remedies. İçinde P. Chowdhary, A. Raj, D. Verma, & Y. Akhter (Ed.), Microorganisms for Sustainable Environment and Health (ss. 419-429). Elsevier. https://doi.org/10.1016/B978-0-12-819001-2.00021-8
Valerio, L. G. (2009). In silico toxicology for the pharmaceutical sciences. Toxicology and Applied Pharmacology, 241(3), 356-370. https://doi.org/10.1016/j.taap.2009.08.022
Valerio, L. G. (2014). In Silico Methods. İçinde P. Wexler (Ed.), Encyclopedia of Toxicology (Third Edition) (Third Edition, ss. 1026-1029). Academic Press. https://doi.org/10.1016/B978-0-12-386454-3.01057-5
Vesilind, P. A., Peirce, J. J., & Weiner, R. F. (2013). Environmental Pollution and Control. Elsevier.
Worachartcheewan, A., Mandi, P., Prachayasittikul, V., Toropova, A. P., Toropov, A. A., & Nantasenamat, C. (2014). Large-scale QSAR study of aromatase inhibitors using SMILES-based descriptors. Chemometrics and Intelligent Laboratory Systems, 138, 120–126.
Zeyrekli, S., Karaman, Y., & Menek, N. (2021). Investigation of Electrochemical Behavior of Mordant Dye (C.I. 17135). International Journal of Electrochemical Science, 16(5), 210533. https://doi.org/10.20964/2021.05.61

Ayrıntılar

Birincil Dil

İngilizce

Konular

Sağlık ve Ekolojik Risk Değerlendirmesi , Çevresel ve Sürdürülebilir Süreçler , Kimya Mühendisliği (Diğer) , Tekstil Kimyası

Bölüm

Araştırma Makalesi

Yazarlar

Gülendam Pirinççi
0009-0002-6276-0534
Türkiye

Şimal Kürümoğlu ^*
0000-0001-9456-5456
Türkiye

Yayımlanma Tarihi

3 Mart 2026

Gönderilme Tarihi

26 Ekim 2025

Kabul Tarihi

2 Ocak 2026

Yayımlandığı Sayı

Yıl 2026 Cilt: 29 Sayı: 1

DOI

https://doi.org/10.17780/ksujes.1811220

IZ

https://izlik.org/JA84LD39GA

Kaynak Göster

RIS / Bibtex

APA

Pirinççi, G., & Kürümoğlu, Ş. (2026). DETERMINATION OF PHYSICOCHEMICAL AND TOXICOLOGICAL PROPERTIES OF AZO DYES USING IN SILICO METHODS. Kahramanmaraş Sütçü İmam Üniversitesi Mühendislik Bilimleri Dergisi, 29(1), 243-258. https://doi.org/10.17780/ksujes.1811220