Research Article
Year 2023,
Volume: 4 Issue: 4, 610 - 620
Abstract
Project Number
BAP- 2017/6-34 M
References
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- 2. Bajpayee, M, Pandey, AK, Parmar, D, et al. Current status of short-term tests for evaluation of genotoxicity, mutagenicity and carcinogenicity of environmental chemicals and NCEs. Toxicology Mechanisms and Methods. 2005; 15, 155.
- 3. McDaniels, AE, Reyes, AL, Wymer, LJ, et al. Comparison of the Salmonella (Ames) test, umu tests, and the SOS chromo tests for detecting genotoxins. Environmental and Molecular Mutagenesis. 1990; 16, 204.
- 4. Czyz, A, Szpilewska, H, Dutkiewicz, R, et al.Comparison of the Ames test and a newly developed assay for detection of mutagenic pollution of marine environments. Mutation Research/Genetic Toxicology and Environmental Mutagenesis. 2002; 519, 67.
- 5. Jena, GB, Kaul, P, Ramarao, P. Genotoxicity testing, a regulatory requirement for drug discovery and development: impact of ICH guidelines. Indian Journal of Pharmacology. 2002; 37, 86.
- 6. Snyder LR, Peters JE, Henkin TM, et al. Molecular Genetics of Bacteria, 4th. ASM Press, Washington.2012 p. 417-424.
- 7. Ames, BN, Mccann, J, Yamasaki, E. Methods for detecting carcinogens and mutagens with the Salmonella/mammalian-microsome mutagenicity test. Mutation Research. 1975; 31, 347.
- 8. Maron, DM, Ames, BN. Revised methods for the Salmonella mutagenicity test. Mutation Research/Environmental Mutagenesis and Related Subjects. 1983;113, 173.
- 9. Mortelmans, K, Zeiger, E. The Ames Salmonella/microsome mutagenicity assay. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis. 2000; 455, 29.
- 10. Kayraldiz, A, Kaya, FF, Canımoğlu, S, et al. Mutagenicity of five food additives in Ames/Salmonella/microsome test. Annals of Microbiology. 2006; 56, 129.
- 11. Barraja, P, Sciabica, L, Diana, P, et al. Synthesis and photochemotherapeutic activity of thiopyrano[2,3-e]indol-2-ones. Bioorganic&Medicinal Chemistry Letters. 2005; 15, 2291.
- 12. Tor, Y, Libman, J, Shanzer, A, et al. Biomimetic ferric ion carriers. A chiral analog of enterobactin. Journal of the American Chemical Society. 1987; 109, 6517.
- 13. Grigg, R, Armstrong, P. X=Y−ZH systems as potential 1,3-dipoles. Part 25. Intramolecular cycloaddition reactions of pyridoxalimines of ε-alkenyl α-amino esters. A possible new approach to pyridoxal enzyme inhibition. Tetrahedron. 1989; 45, 7581.
- 14. Hay, RW, Galyer, AL, Lawrance, GA. The chemistry of sulphur–nitrogen ligands. Part I. Complex-formation and dealkylation reactions of 1,9-bis(tritylthio)- and 1,9-bis(benzyl-thio)-3,7-diazanonane in the presence of metal(II) salts, and the synthesis of dibromo{3,13-dithia-6,10-diazabicyclo[13.4.0]nonadeca-1(15),16,18-triene}nickel(II) Journal of the Chemical Society, DaltonTransactions. 1976; 11, 939.
- 15. Dixon, NE, Gazzola, C, Blakeley, RL, et al. Jack bean urease (EC 3.5.1.5). Metallo enzyme. Simple biological role for nickel. Journal of the American Chemical Society. 1975; 97, 4131.
- 16. Sigel, H, Sigel, A. Nickel and its role in biology. Metal Ions in Biological Systems. 1989; 239, 359.
- 17. Vančo, J, Marek, J, Trávníček, Z, et al. Synthesis, structural characterization, antiradical and antidiabetic activities of copper(II) and zinc(II) Schiff base complexes derived from salicylaldehyde and β-alanine. Inorganic Biochemistry. 2008; 102, 595.
- 18. Sorenson, JRJ. Copper chelates as possible active forms of the antiarthritic agents. Journal of Medicinal Chemistry. 1976; 19, 135.
- 19. May, P.M, Williams, D.R. Role of low molecular weight copper complexes in the control of rheumatoid arthritis. Metal Ions in Biological Systems, Helmut Siegel (ed). Marcel Deccker, New York; 1981 p. 283-317.
- 20. Tumer, F, Goksu, S, Secen, H. Russian. First synthesis of (+/-)-vertilecanin A. Chemical Bullettin. 2005; 54, 2466.
- 21. Karabörk, M, Kırpık, H, Sayın, K, et al. New diazo-containing phenolic oximes: structural characterization, computational studies, and solvent extraction of Cu (II), Ni(II), and Zn(II) ions. Turkish Journal of Chemistry. 2019; 43, 197.
- 22. Onur, S, Köse, M, Koçer, F, et al. Synthesis, characterization and antibacterial effect of diarylmethylamine-based imines. Journal of Molecular Structure. 2020; 1214, 128150.
- 23. Sanner, MF. . Python: A programming language for software integration and development. Journal of molecular graphics & modelling. 1999; 17, 57.
- 24. Ricci, CG., and Netz, PA. Docking studies on DNA-ligand ınteractions: building and application of a protocol to ıdentify the binding mode. Journal of Chemical Information and Modeling. 2009; 49, 1925.
- 25. Nasab, RR., Hassanzadeh F, Khodarahmi GA, et al. Docking study, synthesis and antimicrobial evaluation of some novel 4-anilinoquinazoline derivatives. Research in pharmaceutical sciences. 2017; 12, 425.
- 26. Husunet MT, Mısırlı RÇ, Istıflı ES et al. Investigation of the genotoxic effects of patent blue V (E131) in human peripheral lymphocytes and insilico molecular docking, Drug and Chemical Toxicology. 2021; 27, 1.
- 27. Shityakov, S, and Förster, C. In silico predictive model to determine vector-mediated transport properties for the blood-brain barrier choline transporter. Advances and applications in bioinformatics and chemistry: AABC. 2014; 7, 23.
- 28. Pawan Kumar BK, Reena Gupta MG. Imidazole: Chemistry and biological activities. Think India Journal. 2019; 22(37):359-380.
- 29. Al-Fakeh, MS, Alsikhan MA, Alnawmasi JS. Physico-Chemical Study of Mn (II), Co (II), Cu (II), Cr (III), and Pd (II) Complexes with Schiff-Base and Aminopyrimidyl Derivatives and Anti-Cancer, Antioxidant, Antimicrobial Applications. Molecules. 2023; 28(6):2555.
- 30. Bouhidel Z, Cherouana A, Durand P, et al. Synthesis, spectroscopic characterization, crystal structure, Hirshfeld surface analysis and antimicrobial activities of two triazole Schiff bases and their silver complexes. Inorganica Chimica Acta. 2018; 482, 34-47.
- 31. Zelelew D, Endale M, Melaku Y, et al. Synthesis, Antibacterial, and Antioxidant Activities of Thiazolyl-Pyrazoline Schiff Base Hybrids: A Combined Experimental and Computational Study. Journal of Chemistry. 2022.
- 32. Sathiyanarayanan V, Prasath PV, Sekhar PC, et al. Docking and in vitro molecular biology studies of p-anisidine-appended 1-hydroxy-2-acetonapthanone Schiff base lanthanum (III) complexes. RSC advances. 2020; 10(28):16457-16472.
- 33. Rastija, Vesna, et al. "Effects of coumarinyl schiff bases against phytopathogenic fungi, the soil-beneficial bacteria and entomopathogenic nematodes: Deeper insight into the mechanism of action." Molecules. 2022; 27(7):2196.
- 34. Tian P, Liu D, Liu Z, et. al. Design, synthesis, and insecticidal activity evaluation of novel 4‐(N, N‐diarylmethylamines) furan‐2 (5H)‐one derivatives as potential acetylcholine receptor insecticides. Pest management science. 2019; 75(2), 427-437.
Determination of mutagenic potentials of diarylmethylamine based imine compounds by ames test and computational molecular docking
Abstract
In recent years, studies that investigate the effects of chemical compounds on organisms have increased in direct proportion to their widespread use. In this study, four different bidentate imine ligands and bidentate imine ligands+Cu(II) complexes were synthesized from the bioactive synthetic diarylmethylamine compound. After the ligands and metal complexes obtained were purified using chromatographic and analytical methods, their mutagenic effects were investigated with the Ames/Salmonella test system. In addition, interactions of four different Cu(II) complexes with B-DNA were evaluated with molecular docking analysis. Accordingly, the results indicated a significant increase in the colonies formed in the presence (+S9) and absence (-S9) of the metabolic activation system, meaning a mutagenic effect against strain TA98 and TA100 strains in general.
Keywords
Diarylmethylamine Imine Compounds Salicylaldehyde Cu (II) Complexes Salmonella/Microsome Test Molecular Docking
Supporting Institution
Kahramanmaras Sutcu Imam University
Project Number
BAP- 2017/6-34 M
References
- 1. Claxton, LD, Umbuzeiro, GdeA, et al. The Salmonella mutagenicity assay: the stethoscope of genetic toxicology for the 21st century. Environmental Health Perspectives. 2010; 118, 1515.
- 2. Bajpayee, M, Pandey, AK, Parmar, D, et al. Current status of short-term tests for evaluation of genotoxicity, mutagenicity and carcinogenicity of environmental chemicals and NCEs. Toxicology Mechanisms and Methods. 2005; 15, 155.
- 3. McDaniels, AE, Reyes, AL, Wymer, LJ, et al. Comparison of the Salmonella (Ames) test, umu tests, and the SOS chromo tests for detecting genotoxins. Environmental and Molecular Mutagenesis. 1990; 16, 204.
- 4. Czyz, A, Szpilewska, H, Dutkiewicz, R, et al.Comparison of the Ames test and a newly developed assay for detection of mutagenic pollution of marine environments. Mutation Research/Genetic Toxicology and Environmental Mutagenesis. 2002; 519, 67.
- 5. Jena, GB, Kaul, P, Ramarao, P. Genotoxicity testing, a regulatory requirement for drug discovery and development: impact of ICH guidelines. Indian Journal of Pharmacology. 2002; 37, 86.
- 6. Snyder LR, Peters JE, Henkin TM, et al. Molecular Genetics of Bacteria, 4th. ASM Press, Washington.2012 p. 417-424.
- 7. Ames, BN, Mccann, J, Yamasaki, E. Methods for detecting carcinogens and mutagens with the Salmonella/mammalian-microsome mutagenicity test. Mutation Research. 1975; 31, 347.
- 8. Maron, DM, Ames, BN. Revised methods for the Salmonella mutagenicity test. Mutation Research/Environmental Mutagenesis and Related Subjects. 1983;113, 173.
- 9. Mortelmans, K, Zeiger, E. The Ames Salmonella/microsome mutagenicity assay. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis. 2000; 455, 29.
- 10. Kayraldiz, A, Kaya, FF, Canımoğlu, S, et al. Mutagenicity of five food additives in Ames/Salmonella/microsome test. Annals of Microbiology. 2006; 56, 129.
- 11. Barraja, P, Sciabica, L, Diana, P, et al. Synthesis and photochemotherapeutic activity of thiopyrano[2,3-e]indol-2-ones. Bioorganic&Medicinal Chemistry Letters. 2005; 15, 2291.
- 12. Tor, Y, Libman, J, Shanzer, A, et al. Biomimetic ferric ion carriers. A chiral analog of enterobactin. Journal of the American Chemical Society. 1987; 109, 6517.
- 13. Grigg, R, Armstrong, P. X=Y−ZH systems as potential 1,3-dipoles. Part 25. Intramolecular cycloaddition reactions of pyridoxalimines of ε-alkenyl α-amino esters. A possible new approach to pyridoxal enzyme inhibition. Tetrahedron. 1989; 45, 7581.
- 14. Hay, RW, Galyer, AL, Lawrance, GA. The chemistry of sulphur–nitrogen ligands. Part I. Complex-formation and dealkylation reactions of 1,9-bis(tritylthio)- and 1,9-bis(benzyl-thio)-3,7-diazanonane in the presence of metal(II) salts, and the synthesis of dibromo{3,13-dithia-6,10-diazabicyclo[13.4.0]nonadeca-1(15),16,18-triene}nickel(II) Journal of the Chemical Society, DaltonTransactions. 1976; 11, 939.
- 15. Dixon, NE, Gazzola, C, Blakeley, RL, et al. Jack bean urease (EC 3.5.1.5). Metallo enzyme. Simple biological role for nickel. Journal of the American Chemical Society. 1975; 97, 4131.
- 16. Sigel, H, Sigel, A. Nickel and its role in biology. Metal Ions in Biological Systems. 1989; 239, 359.
- 17. Vančo, J, Marek, J, Trávníček, Z, et al. Synthesis, structural characterization, antiradical and antidiabetic activities of copper(II) and zinc(II) Schiff base complexes derived from salicylaldehyde and β-alanine. Inorganic Biochemistry. 2008; 102, 595.
- 18. Sorenson, JRJ. Copper chelates as possible active forms of the antiarthritic agents. Journal of Medicinal Chemistry. 1976; 19, 135.
- 19. May, P.M, Williams, D.R. Role of low molecular weight copper complexes in the control of rheumatoid arthritis. Metal Ions in Biological Systems, Helmut Siegel (ed). Marcel Deccker, New York; 1981 p. 283-317.
- 20. Tumer, F, Goksu, S, Secen, H. Russian. First synthesis of (+/-)-vertilecanin A. Chemical Bullettin. 2005; 54, 2466.
- 21. Karabörk, M, Kırpık, H, Sayın, K, et al. New diazo-containing phenolic oximes: structural characterization, computational studies, and solvent extraction of Cu (II), Ni(II), and Zn(II) ions. Turkish Journal of Chemistry. 2019; 43, 197.
- 22. Onur, S, Köse, M, Koçer, F, et al. Synthesis, characterization and antibacterial effect of diarylmethylamine-based imines. Journal of Molecular Structure. 2020; 1214, 128150.
- 23. Sanner, MF. . Python: A programming language for software integration and development. Journal of molecular graphics & modelling. 1999; 17, 57.
- 24. Ricci, CG., and Netz, PA. Docking studies on DNA-ligand ınteractions: building and application of a protocol to ıdentify the binding mode. Journal of Chemical Information and Modeling. 2009; 49, 1925.
- 25. Nasab, RR., Hassanzadeh F, Khodarahmi GA, et al. Docking study, synthesis and antimicrobial evaluation of some novel 4-anilinoquinazoline derivatives. Research in pharmaceutical sciences. 2017; 12, 425.
- 26. Husunet MT, Mısırlı RÇ, Istıflı ES et al. Investigation of the genotoxic effects of patent blue V (E131) in human peripheral lymphocytes and insilico molecular docking, Drug and Chemical Toxicology. 2021; 27, 1.
- 27. Shityakov, S, and Förster, C. In silico predictive model to determine vector-mediated transport properties for the blood-brain barrier choline transporter. Advances and applications in bioinformatics and chemistry: AABC. 2014; 7, 23.
- 28. Pawan Kumar BK, Reena Gupta MG. Imidazole: Chemistry and biological activities. Think India Journal. 2019; 22(37):359-380.
- 29. Al-Fakeh, MS, Alsikhan MA, Alnawmasi JS. Physico-Chemical Study of Mn (II), Co (II), Cu (II), Cr (III), and Pd (II) Complexes with Schiff-Base and Aminopyrimidyl Derivatives and Anti-Cancer, Antioxidant, Antimicrobial Applications. Molecules. 2023; 28(6):2555.
- 30. Bouhidel Z, Cherouana A, Durand P, et al. Synthesis, spectroscopic characterization, crystal structure, Hirshfeld surface analysis and antimicrobial activities of two triazole Schiff bases and their silver complexes. Inorganica Chimica Acta. 2018; 482, 34-47.
- 31. Zelelew D, Endale M, Melaku Y, et al. Synthesis, Antibacterial, and Antioxidant Activities of Thiazolyl-Pyrazoline Schiff Base Hybrids: A Combined Experimental and Computational Study. Journal of Chemistry. 2022.
- 32. Sathiyanarayanan V, Prasath PV, Sekhar PC, et al. Docking and in vitro molecular biology studies of p-anisidine-appended 1-hydroxy-2-acetonapthanone Schiff base lanthanum (III) complexes. RSC advances. 2020; 10(28):16457-16472.
- 33. Rastija, Vesna, et al. "Effects of coumarinyl schiff bases against phytopathogenic fungi, the soil-beneficial bacteria and entomopathogenic nematodes: Deeper insight into the mechanism of action." Molecules. 2022; 27(7):2196.
- 34. Tian P, Liu D, Liu Z, et. al. Design, synthesis, and insecticidal activity evaluation of novel 4‐(N, N‐diarylmethylamines) furan‐2 (5H)‐one derivatives as potential acetylcholine receptor insecticides. Pest management science. 2019; 75(2), 427-437.
There are 34 citations in total.
Details
| Primary Language | English |
|---|---|
| Subjects | Toxicology |
| Journal Section | Research Articles |
| Authors | |
| Project Number | BAP- 2017/6-34 M |
| Early Pub Date | February 15, 2024 |
| Publication Date | |
| Submission Date | December 11, 2023 |
| Acceptance Date | February 10, 2024 |
| Published in Issue | Year 2023 Volume: 4 Issue: 4 |
