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P. Carter, P. Scherle, Jodi Muckelbauer, M. Voss, Rui-Qin Liu, L. Thompson, A. Tebben, K. Solomon, Yvonne Lo, Zhong Li, P. Strzemienski, Gengjie Yang, Nikoo Falahatpisheh, Meizhong Xu, Zhongren Wu, N. Farrow, K. Ramnarayan, Jing Wang, D. Rideout, V. Yalamoori, P. Domaille, D. Underwood, J. Trzăskos, S. Friedman, R. Newton, C. Decicco (2001)Photochemically enhanced binding of small molecules to the tumor necrosis factor receptor-1 inhibits the binding of TNF-α
Proceedings of the National Academy of Sciences of the United States of America, 98
(2021)Nigerian Patent NG/PT/NC/2021/5695
Or (2012)Guidance for Industry S 2 ( R 1 ) Genotoxicity Testing and Data Interpretation for Pharmaceuticals Intended for Human Use
F. Rafii, J. Hall, C. Cerniglia (1997)Mutagenicity of azo dyes used in foods, drugs and cosmetics before and after reduction by Clostridium species from the human intestinal tract.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 35 9
8 - Ammonionaphthalene - 2 - sulfonate monohydrate : the zwitterionic hydrate of 1 , 7 - Cleve ’ s acid
C. Lipinski (2016)Rule of five in 2015 and beyond: Target and ligand structural limitations, ligand chemistry structure and drug discovery project decisions.
Advanced drug delivery reviews, 101
M. Tsuboy, J. Angeli, M. Mantovani, S. Knasmüller, G. Umbuzeiro, L. Ribeiro (2007)Genotoxic, mutagenic and cytotoxic effects of the commercial dye CI Disperse Blue 291 in the human hepatic cell line HepG2.
Toxicology in vitro : an international journal published in association with BIBRA, 21 8
Giuseppe Barca, C. Bertoni, L. Carrington, D. Datta, N. Silva, J. Deustua, D. Fedorov, J. Gour, A. Gunina, Emilie Guidez, Taylor Harville, S. Irle, J. Ivanic, K. Kowalski, Sarom Leang, Hui Li, Wei Li, J. Lutz, I. Magoulas, J. Mato, V. Mironov, H. Nakata, Buu Pham, P. Piecuch, David Poole, Spencer Pruitt, Alistair Rendell, Luke Roskop, K. Ruedenberg, Tosaporn Sattasathuchana, Michael Schmidt, Jun Shen, L. Slipchenko, M. Sosonkina, Vaibhav Sundriyal, Ananta Tiwari, Jorge Vallejo, Bryce Westheimer, M. Włoch, Peng Xu, F. Zahariev, Mark Gordon (2020)Recent developments in the general atomic and molecular electronic structure system.
The Journal of chemical physics, 152 15
Vong Dien-Yu, Hwang Siaw-San, Chee Wezen, Sim Ui-Hang (2022)Computational ligand–receptor docking simulation of piperine with apoptosis-associated factors
Journal of Applied Biology & Biotechnology
Britnie James, T. Griffith (2014)Tumor necrosis factor-related apoptosis-inducing ligand-induced apoptotic pathways in cancer immunosurveillance: molecular mechanisms and prospects for therapy
Atrayee Bandyopadhyay, S. Ghoshal, A. Mukherjee (2008)Genotoxicity Testing of Low-Calorie Sweeteners: Aspartame, Acesulfame-K, and Saccharin
Drug and Chemical Toxicology, 31
R. Combes, R. Haveland-Smith (1982)A review of the genotoxicity of food, drug and cosmetic colours and other azo, triphenylmethane and xanthene dyes.
Mutation research, 98 2
Narendra Singh (2005)Apoptosis assessment by the DNA diffusion assay.
Methods in molecular medicine, 111
O. Thomas, O. Adegoke (2015)Toxicity of food colours and additives: A review
African Journal of Pharmacy and Pharmacology, 9
R. Jung, D. Steinle, R. Anliker (1992)A compilation of genotoxicity and carcinogenicity data on aromatic aminosulphonic acids.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 30 7
K. Chung (2016)Azo dyes and human health: A review
Journal of Environmental Science and Health, Part C, 34
Alex Roche (1982)Organic Chemistry:
Graham Smith, U. Wermuth, D. Young, J. White (2004)Zwitterionic 5-amino-2-naphthalenesulfonic acid
Acta Crystallographica Section E-structure Reports Online, 60
O. Adegoke, Jin Kyu, A. Mukherjee (2012)In vitro genotoxicity evaluation of 4-carboxyl-2,6-dinitrophenylazohydroxynaphthalenes using human lymphocytes.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 50 3-4
M. Nouri, M. Al-Halbosiy, B. Dheeb, A. Hashim (2015)Cytotoxicity and genotoxicity of gliotoxin on human lymphocytes in vitro
Journal of King Saud University - Science, 27
G. Brambilla, A. Martelli (2009)Update on genotoxicity and carcinogenicity testing of 472 marketed pharmaceuticals.
Mutation research, 681 2-3
N. Zengin, D. Yüzbaşıoğlu, F. Ünal, S. Yılmaz, H. Aksoy (2011)The evaluation of the genotoxicity of two food preservatives: sodium benzoate and potassium benzoate.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 49 4
D. Dougherty (2013)The cation-π interaction.
Accounts of chemical research, 46 4
O. Thomas, O. Adegoke (2022)Synthesis, characterization and solvatochromic behaviour of new water-soluble 8-hydroxy-3,6-disulphonaphthyl azohydroxynaphthalenes
Journal of Taibah University for Science, 16
G. Das, Abjal Shaik, K. Jamil (2006)Estimation of Apoptosis and Necrosis Caused by Pesticides In Vitro on Human Lymphocytes Using DNA Diffusion Assay
Drug and Chemical Toxicology, 29
T. Gichner, A. Mukherjee, E. Wagner, M. Plewa (2005)Evaluation of the nuclear DNA Diffusion Assay to detect apoptosis and necrosis.
Mutation research, 586 1
Julia Bausinger, G. Speit (2016)The impact of lymphocyte isolation on induced DNA damage in human blood samples measured by the comet assay.
Mutagenesis, 31 5
P. Møller, A. Azqueta, É. Boutet-Robinet, G. Koppen, S. Bonassi, M. Milić, G. Gajski, S. Costa, J. Teixeira, Cristiana Pereira, M. Dusinska, R. Godschalk, G. Brunborg, K. Gutzkow, L. Giovannelli, M. Cooke, E. Richling, B. Laffon, V. Valdiglesias, N. Başaran, C. Bo’, B. Žegura, M. Novak, H. Stopper, P. Vodicka, Sona Vodenkova, V. Andrade, M. Šrámková, A. Gábelová, A. Collins, S. Langie (2020)Minimum Information for Reporting on the Comet Assay (MIRCA): recommendations for describing comet assay procedures and results
Nature Protocols, 15
N. Xie, Q. Du, Jianxiu Li, R. Huang (2015)Exploring Strong Interactions in Proteins with Quantum Chemistry and Examples of Their Applications in Drug Design
PLoS ONE, 10
John Millar (1992)Evaluation of the
Physical review. B, Condensed matter, 45 24
Manosij Ghosh, Maumita Bandyopadhyay, A. Mukherjee (2010)Genotoxicity of titanium dioxide (TiO2) nanoparticles at two trophic levels: plant and human lymphocytes.
Chemosphere, 81 10
N. Singh, Michael McCoy, R. Tice, E. Schneider (1988)A simple technique for quantitation of low levels of DNA damage in individual cells.
Experimental cell research, 175 1
Alja Plošnik, M. Vračko, M. Dolenc (2016)Mutagenic and carcinogenic structural alerts and their mechanisms of action
Archives of Industrial Hygiene and Toxicology, 67
D. Hwang (2013)Cation-π Interaction
Mahima Bajpayee, Ashutosh Kumar, A. Dhawan (2013)The comet assay: assessment of in vitro and in vivo DNA damage.
Methods in molecular biology, 1044
E. Pettersen, Thomas Goddard, Conrad Huang, Gregory Couch, Daniel Greenblatt, E. Meng, T. Ferrin (2004)UCSF Chimera—A visualization system for exploratory research and analysis
Journal of Computational Chemistry, 25
P. Mpountoukas, A. Pantazaki, E. Kostareli, P. Christodoulou, D. Kareli, Stamatia Poliliou, Costas Mourelatos, V. Lambropoulou, T. Lialiaris (2010)Cytogenetic evaluation and DNA interaction studies of the food colorants amaranth, erythrosine and tartrazine.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 48 10
W. Foye, T. Lemke, David Williams (2002)Foye's Principles of Medicinal Chemistry
Sammar Alsaedi, Bandar Babgi, Magda Abdellatif, A. Emwas, Mariusz Jaremko, M. Humphrey, M. Hussien (2021)Effect of Net Charge on DNA-Binding, Protein-Binding and Anticancer Properties of Copper(I) Phosphine-Diimine Complexes
Journal of Inorganic and Organometallic Polymers and Materials, 31
Timothy Allen, Matthew Grayson, J. Goodman, S. Gutsell, P. Russell (2018)Using Transition State Modeling To Predict Mutagenicity for Michael Acceptors
Journal of chemical information and modeling, 58 6
S. Dallakyan, A. Olson (2015)Small-molecule library screening by docking with PyRx.
Methods in molecular biology, 1263
E. Ferraz, M. Grando, D. Oliveira (2011)The azo dye Disperse Orange 1 induces DNA damage and cytotoxic effects but does not cause ecotoxic effects in Daphnia similis and Vibrio fischeri.
Journal of hazardous materials, 192 2
(2000)Guidance for Industry and other stakeholders: Toxicological principles for the safety assessment of food ingredients
Yanxin Lu, Yang Liu, Chunzhang Yang (2017)Evaluating In Vitro DNA Damage Using Comet Assay.
Journal of visualized experiments : JoVE, 128
H. Wajant, D. Siegmund (2019)TNFR1 and TNFR2 in the Control of the Life and Death Balance of Macrophages
Frontiers in Cell and Developmental Biology, 7
D. Mcilwain, T. Berger, T. Mak (2013)Caspase functions in cell death and disease.
Cold Spring Harbor perspectives in biology, 5 4
G. Lin, W. Solodar (1988)Structure-activity relationship studies on the mutagenicity of some azo dyes in the Salmonella/microsome assay.
Mutagenesis, 3 4
Kumbhakar Vishambhar, Datta Kumar, Das Debadrito, Ghosh Bapi, Pramanik Ankita, G. Sudha (2018)Assessment of Cytotoxicity and Cellular Apoptosis Induced by Azo-Dyes (Methyl Orange and Malachite Green) and Heavy Metals (Cadmium and Lead) Using Nigella sativa L. (Black Cumin)
Abstract Regulatory agencies require demonstration of non-genotoxicity of new chemical entities prior to their use as pharmaceuticals or additives. Consequently, the in vitro cytotoxicity, genotoxicity and apoptoxicity of five novel monoazo colourants (8-hydroxy-3,6-disulphonaphthyl azohydroxynaphthalenes, 3a-e) on human lymphocytes were evaluated using a cell viability assay, alkaline comet assay, DNA diffusion assay, DFT calculations and molecular docking. The test concentrations of the compounds varied from 0 to 3.4 mM. Relative to negative control, the compounds at concentrations up to 0.5mM induced small dose-dependent reduction (< 20%) in viability of lymphocytes. Statistically significant changes (p<0.05) in DNA damage parameters (percent tail DNA, tail extent moment, olive tail moment) were observed at all concentrations of 3a, 3b while 3c-e showed genotoxicity at 2.8, 0.17 and 3.4 mM respectively. Compounds 3a, 3b, 3d induced apoptosis at concentrations below cytotoxic doses while 3c and 3e were non-apoptoxic at all test concentrations. DFT calculations showed the genotoxicity of 3a-e increased with electrophilicity and ionization potentials of the compounds. Molecular docking of 3a-e with apoptosis-associated proteins revealed binding affinity patterns that were consistent with observed experimental apoptoxicity. The structure-genotoxicity relationships of five novel monoazo compounds, which can be employed in the design of safer congeners, have been elucidated.
Analytical Chemistry Letters – Taylor & Francis
Published: Jan 2, 2023
Keywords: Azo compounds; Alkaline comet assay; DNA diffusion assay; DFT calculation; Molecular docking
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