Research Article
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DNA Interactions, Mutagenic, Anti-Mutagenic And Antimicrobial Activities of (E)-2-((3,5-Bis(Trifluoromethyl)Phenylimino)Methyl)-4,6- Dimethoxyphenol

Year 2021, , 339 - 348, 15.04.2021
https://doi.org/10.16984/saufenbilder.793776

Abstract

Small molecules that interact with DNA are known to be effective as anticancer and antimicrobial agents. Therefore it is significant to search for new molecules interacting with DNA as potential new therapeutic agents. In this study, we aimed to investigate interactions of novel fluorine substituted imine compound with DNA, (E)-2-((3,5-bis(trifluoromethyl) phenylimino)methyl)-4,6-dimethoxyphenol, and investigate its biological activities. DNA interactions of the compound were investigated by UV-Vis absorption spectroscopy and gel electrophoresis. The results demonstrated that the compound binds to DNA via intercalation. Agarose gel electrophoresis experiments showed that the compound does not cleave pBR322 plasmid DNA hydrolytically or oxidatively. Furthermore, mutagenic, anti-mutagenic, and antimicrobial activities of the compound were studied by Ames and broth microdilution test, respectively. The compound showed mutagenic activity on both TA98 and TA100 strains. Also, the antimutagenic activity was observed in TA100 strain of S. typhimurium. It demonstrated antimicrobial activity against the microorganisms tested in the concentration range of 16-64 µg/µL. The results show that the compound intercalates with DNA and has promising biological activities.

Supporting Institution

Çanakkale Onsekiz Mart University, Scientific Research Project Committee (ÇOMÜ BAP)

Project Number

FBA-2017-1125

Thanks

We are grateful to Assoc. Prof. Dr. Mustafa YILDIZ in Çanakkale Onsekiz Mart University, Faculty of Arts And Sciences, Chemistry Department for providing the compound that used in this research.

References

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  • [2] N. Li, Y. Ma, C. Yang, L. Guo, and X. Yang, “Interaction of anticancer drug mitoxantrone with DNA analyzed by electrochemical and spectroscopic methods,” Biophys. Chem., vol. 116, no. 3, pp. 199–205, 2005.
  • [3] S. Ghosh, “Cisplatin: The first metal based anticancer drug,” Bioorganic Chemistry, vol. 88. p. 102925, 2019.
  • [4] S. M. Pradeepa, H. S. Bhojya Naik, B. Vinay Kumar, K. Indira Priyadarsini, A. Barik, and S. Jayakumar, “Synthesis and characterization of cobalt(II), nickel(II) and copper(II)-based potential photosensitizers: Evaluation of their DNA binding profile, cleavage and photocytotoxicity,” Inorganica Chim. Acta, vol. 428, pp. 138–146, 2015.
  • [5] B. L. Fei et al., “Effects of copper ions on DNA binding and cytotoxic activity of a chiral salicylidene Schiff base,” J. Photochem. Photobiol. B Biol., vol. 132, pp. 36–44, 2014.
  • [6] R. Gust, W. Beck, G. Jaouen, and H. Schönenberger, “Optimization of cisplatin for the treatment of hormone dependent tumoral diseases. Part 1: Use of steroidal ligands,” Coordination Chemistry Reviews, vol. 253, no. 21–22. pp. 2742–2759, 2009.
  • [7] K. Dhara, P. Roy, J. Ratha, M. Manassero, and P. Banerjee, “Synthesis, crystal structure, magnetic property and DNA cleavage activity of a new terephthalate-bridged tetranuclear copper(II) complex,” Polyhedron, vol. 26, no. 15, pp. 4509–4517, 2007.
  • [8] Y. L. Æ. Z. Yang, “Crystal structures , antioxidation and DNA binding properties of Yb ( III ) complexes with Schiff-base ligands derived from 8-hydroxyquinoline-2-carbaldehyde and four aroylhydrazines,” Biometals, pp. 733–751, 2009.
  • [9] B. dui Wang, Z. Y. Yang, and T. rong Li, “Synthesis, characterization, and DNA-binding properties of the Ln(III) complexes with 6-hydroxy chromone-3-carbaldehyde-(2′-hydroxy) benzoyl hydrazone,” Bioorganic Med. Chem., vol. 14, no. 17, pp. 6012–6021, 2006.
  • [10] Z. C. Liu et al., “Crystal structures, DNA-binding and cytotoxic activities studies of Cu(II) complexes with 2-oxo-quinoline-3-carbaldehyde Schiff-bases,” Eur. J. Med. Chem., vol. 45, no. 11, pp. 5353–5361, 2010.
  • [11] G. Zhang, S. Shuang, C. Dong, D. Liu, and M. M. F. Choi, “Investigation on DNA assembly to neutral red-cyclodextrin complex by molecular spectroscopy,” J. Photochem. Photobiol. B Biol., vol. 74, no. 2004, pp. 127–134, 2004.
  • [12] X. Qiao et al., “Study on potential antitumor mechanism of a novel Schiff Base copper(II) complex: Synthesis, crystal structure, DNA binding, cytotoxicity and apoptosis induction activity,” J. Inorg. Biochem., vol. 105, no. 5, pp. 728–737, 2011.
  • [13] S. Dhar, P. A. N. Reddy, M. Nethaji, S. Mahadevan, M. K. Saha, and A. R. Chakravarty, “Effect of Steric Encumbrance of Tris(3-phenylpyrazolyl)borate on the Structure and Properties of Ternary Copper(II) Complexes Having N,N-Donor Heterocyclic Bases Complexes of formulation [Cu(Tp Ph )(L)](ClO 4 ) (1−4), where Tp,” vol. 41, no. 2002, pp. 3469–3476, 2002.
  • [14] D. K. Chand et al., “Affinity and Nuclease Activity of Macrocyclic Polyamines and Their CuII Complexes,” Chem. – A Eur. J., vol. 6, no. 21, pp. 4001–4008, 2000.
  • [15] B. E. Smart, “Fluorine substituent effects (on bioactivity),” in Journal of Fluorine Chemistry, vol. 109, no. 1, pp. 3–11, 2001.
  • [16] T. C. Jenkins, “Optical Absorbance and Fluorescence Techniques for Measuring DNA–Drug Interactions,” in Drug-DNA Interaction Protocols, New Jersey: Humana Press, pp. 195–218, 1997.
  • [17] V. C. da Silveira, J. S. Luz, C. C. Oliveira, I. Graziani, M. R. Ciriolo, and A. M. da C. Ferreira, “Double-strand DNA cleavage induced by oxindole-Schiff base copper(II) complexes with potential antitumor activity,” J. Inorg. Biochem., vol. 102, no. 2008, pp. 1090–1103, 2008.
  • [18] D. M. Maron and B. N. Ames, “Revised methods for the Salmonella mutagenicity test,” Mutation Research/Environmental Mutagenesis and Related Subjects, vol. 113, no. 3–4. Elsevier, pp. 173–215, 1983.
  • [19] K. Mortelmans and E. Zeiger, “The Ames Salmonella/microsome mutagenicity assay,” Mutat. Res. - Fundam. Mol. Mech. Mutagen., vol. 455, no. 1–2, pp. 29–60, 2000.
  • [20] Y. Ikken, P. Morales, A. Martínez, M. L. Marín, A. I. Haza, and M. I. Cambero, “Antimutagenic effect of fruit and vegetable ethanolic extracts against N-nitrosamines evaluated by the Ames test,” J. Agric. Food Chem., vol. 47, no. 8, pp. 3257–3264, 1999.
  • [21] P. S. Negi, G. K. Jayaprakasha, and B. S. Jena, “Antioxidant and antimutagenic activities of pomegranate peel extracts,” Food Chem., vol. 80, no. 3, pp. 393–397, 2003.
  • [22] C. E. Hong and S. Y. Lyu, “Genotoxicity detection of five medicinal plants in Nigeria,” J. Toxicol. Sci., vol. 36, no. 1, pp. 87–93, 2011.
  • [23] Clinical and Laboratory Standards Institute, “Clinical and Laboratory Standards Institute,” Wane, Pennsylvania: Clinical and Laboratory Satandards Institute, pp. 604–604, 2019.
  • [24] G. J. Chen et al., “Synthesis, DNA binding, photo-induced DNA cleavage, cytotoxicity and apoptosis studies of copper(II) complexes,” J. Inorg. Biochem., vol. 105, no. 2, pp. 119–126, 2011.
  • [25] A. M. Pyle, J. P. Rehmann, R. Meshoyrer, N. J. Turro, J. K. Barton, and C. V Kumar, “Mixed-Ligand complexes of ruthenium(II): Factors governing binding to DNA,” J. Am. Chem. Soc., vol. 111, no. 8, pp. 3051–3058, 1989.
  • [26] N. Vamsikrishna, M. P. Kumar, G. Ramesh, N. Ganji, S. Daravath, and Shivaraj, “DNA interactions and biocidal activity of metal complexes of benzothiazole Schiff bases: synthesis, characterization and validation,” J. Chem. Sci., vol. 129, no. 5, pp. 609–622, 2017.
  • [27] R. Prabhakaran et al., “DNA binding, antioxidant, cytotoxicity (MTT, lactate dehydrogenase, NO), and cellular uptake studies of structurally different nickel(II) thiosemicarbazone complexes: Synthesis, spectroscopy, electrochemistry, and X-ray crystallography,” J. Biol. Inorg. Chem., vol. 18, no. 2, pp. 233–247, 2013.
  • [28] J. B. Chaires, “Energetics of drug-DNA interactions,” Biopolymers, vol. 44, no. 3, pp. 201–215, 1997.
  • [29] R. Palchaudhuri and P. J. Hergenrother, “DNA as a target for anticancer compounds: methods to determine the mode of binding and the mechanism of action,” Curr. Opin. Biotechnol., vol. 18, no. 6, pp. 497–503, 2007.
  • [30] R. D. Snyder, J. McNulty, G. Zairov, D. E. Ewing, and L. B. Hendry, “The influence of N-dialkyl and other cationic substituents on DNA intercalation and genotoxicity,” Mutat. Res. - Fundam. Mol. Mech. Mutagen., vol. 578, no. 1–2, pp. 88–99, 2005.
  • [31] R. D. Snyder, “Assessment of atypical DNA intercalating agents in biological and in silico systems,” Mutat. Res. - Fundam. Mol. Mech. Mutagen., vol. 623, no. 1–2, pp. 72–82, 2007.
  • [32] L. Subha, C. Balakrishnan, S. Thalamuthu, and M. A. Neelakantan, “Mixed ligand Cu(II) complexes containing o-vanillin-L-tryptophan Schiff base and heterocyclic nitrogen bases: Synthesis, structural characterization, and biological properties,” J. Coord. Chem., vol. 68, no. 6, pp. 1021–1039, 2015.
  • [33] L. Strekowski and B. Wilson, “Noncovalent interactions with DNA: An overview,” Mutat. Res. - Fundam. Mol. Mech. Mutagen., vol. 623, no. 1–2, pp. 3–13, 2007.
  • [34] H. S. B. N. Sangeetha Gowda K.R., Blessy Baby Mathew, C.N. Sudhamani, “Mechanism of DNA Binding and Cleavage, Biomedicine and Biotechnology,” Biomed. Biotechnol., vol. Vol. 2 No., no. 1, pp. 1–9, 2014.
  • [35] E. Buraka et al., “DNA-binding studies of AV-153, an antimutagenic and DNA repair-stimulating derivative of 1,4-dihydropiridine,” Chem. Biol. Interact., vol. 220, no. 2014, pp. 200–207, 2014.
Year 2021, , 339 - 348, 15.04.2021
https://doi.org/10.16984/saufenbilder.793776

Abstract

Project Number

FBA-2017-1125

References

  • [1] A. Rabbani-Chadegani, S. Keyvani-Ghamsari, and N. Zarkar, “Spectroscopic studies of dactinomycin and vinorelbine binding to deoxyribonucleic acid and chromatin,” Spectrochim. Acta - Part A Mol. Biomol. Spectrosc., vol. 84, no. 1, pp. 62–67, 2011.
  • [2] N. Li, Y. Ma, C. Yang, L. Guo, and X. Yang, “Interaction of anticancer drug mitoxantrone with DNA analyzed by electrochemical and spectroscopic methods,” Biophys. Chem., vol. 116, no. 3, pp. 199–205, 2005.
  • [3] S. Ghosh, “Cisplatin: The first metal based anticancer drug,” Bioorganic Chemistry, vol. 88. p. 102925, 2019.
  • [4] S. M. Pradeepa, H. S. Bhojya Naik, B. Vinay Kumar, K. Indira Priyadarsini, A. Barik, and S. Jayakumar, “Synthesis and characterization of cobalt(II), nickel(II) and copper(II)-based potential photosensitizers: Evaluation of their DNA binding profile, cleavage and photocytotoxicity,” Inorganica Chim. Acta, vol. 428, pp. 138–146, 2015.
  • [5] B. L. Fei et al., “Effects of copper ions on DNA binding and cytotoxic activity of a chiral salicylidene Schiff base,” J. Photochem. Photobiol. B Biol., vol. 132, pp. 36–44, 2014.
  • [6] R. Gust, W. Beck, G. Jaouen, and H. Schönenberger, “Optimization of cisplatin for the treatment of hormone dependent tumoral diseases. Part 1: Use of steroidal ligands,” Coordination Chemistry Reviews, vol. 253, no. 21–22. pp. 2742–2759, 2009.
  • [7] K. Dhara, P. Roy, J. Ratha, M. Manassero, and P. Banerjee, “Synthesis, crystal structure, magnetic property and DNA cleavage activity of a new terephthalate-bridged tetranuclear copper(II) complex,” Polyhedron, vol. 26, no. 15, pp. 4509–4517, 2007.
  • [8] Y. L. Æ. Z. Yang, “Crystal structures , antioxidation and DNA binding properties of Yb ( III ) complexes with Schiff-base ligands derived from 8-hydroxyquinoline-2-carbaldehyde and four aroylhydrazines,” Biometals, pp. 733–751, 2009.
  • [9] B. dui Wang, Z. Y. Yang, and T. rong Li, “Synthesis, characterization, and DNA-binding properties of the Ln(III) complexes with 6-hydroxy chromone-3-carbaldehyde-(2′-hydroxy) benzoyl hydrazone,” Bioorganic Med. Chem., vol. 14, no. 17, pp. 6012–6021, 2006.
  • [10] Z. C. Liu et al., “Crystal structures, DNA-binding and cytotoxic activities studies of Cu(II) complexes with 2-oxo-quinoline-3-carbaldehyde Schiff-bases,” Eur. J. Med. Chem., vol. 45, no. 11, pp. 5353–5361, 2010.
  • [11] G. Zhang, S. Shuang, C. Dong, D. Liu, and M. M. F. Choi, “Investigation on DNA assembly to neutral red-cyclodextrin complex by molecular spectroscopy,” J. Photochem. Photobiol. B Biol., vol. 74, no. 2004, pp. 127–134, 2004.
  • [12] X. Qiao et al., “Study on potential antitumor mechanism of a novel Schiff Base copper(II) complex: Synthesis, crystal structure, DNA binding, cytotoxicity and apoptosis induction activity,” J. Inorg. Biochem., vol. 105, no. 5, pp. 728–737, 2011.
  • [13] S. Dhar, P. A. N. Reddy, M. Nethaji, S. Mahadevan, M. K. Saha, and A. R. Chakravarty, “Effect of Steric Encumbrance of Tris(3-phenylpyrazolyl)borate on the Structure and Properties of Ternary Copper(II) Complexes Having N,N-Donor Heterocyclic Bases Complexes of formulation [Cu(Tp Ph )(L)](ClO 4 ) (1−4), where Tp,” vol. 41, no. 2002, pp. 3469–3476, 2002.
  • [14] D. K. Chand et al., “Affinity and Nuclease Activity of Macrocyclic Polyamines and Their CuII Complexes,” Chem. – A Eur. J., vol. 6, no. 21, pp. 4001–4008, 2000.
  • [15] B. E. Smart, “Fluorine substituent effects (on bioactivity),” in Journal of Fluorine Chemistry, vol. 109, no. 1, pp. 3–11, 2001.
  • [16] T. C. Jenkins, “Optical Absorbance and Fluorescence Techniques for Measuring DNA–Drug Interactions,” in Drug-DNA Interaction Protocols, New Jersey: Humana Press, pp. 195–218, 1997.
  • [17] V. C. da Silveira, J. S. Luz, C. C. Oliveira, I. Graziani, M. R. Ciriolo, and A. M. da C. Ferreira, “Double-strand DNA cleavage induced by oxindole-Schiff base copper(II) complexes with potential antitumor activity,” J. Inorg. Biochem., vol. 102, no. 2008, pp. 1090–1103, 2008.
  • [18] D. M. Maron and B. N. Ames, “Revised methods for the Salmonella mutagenicity test,” Mutation Research/Environmental Mutagenesis and Related Subjects, vol. 113, no. 3–4. Elsevier, pp. 173–215, 1983.
  • [19] K. Mortelmans and E. Zeiger, “The Ames Salmonella/microsome mutagenicity assay,” Mutat. Res. - Fundam. Mol. Mech. Mutagen., vol. 455, no. 1–2, pp. 29–60, 2000.
  • [20] Y. Ikken, P. Morales, A. Martínez, M. L. Marín, A. I. Haza, and M. I. Cambero, “Antimutagenic effect of fruit and vegetable ethanolic extracts against N-nitrosamines evaluated by the Ames test,” J. Agric. Food Chem., vol. 47, no. 8, pp. 3257–3264, 1999.
  • [21] P. S. Negi, G. K. Jayaprakasha, and B. S. Jena, “Antioxidant and antimutagenic activities of pomegranate peel extracts,” Food Chem., vol. 80, no. 3, pp. 393–397, 2003.
  • [22] C. E. Hong and S. Y. Lyu, “Genotoxicity detection of five medicinal plants in Nigeria,” J. Toxicol. Sci., vol. 36, no. 1, pp. 87–93, 2011.
  • [23] Clinical and Laboratory Standards Institute, “Clinical and Laboratory Standards Institute,” Wane, Pennsylvania: Clinical and Laboratory Satandards Institute, pp. 604–604, 2019.
  • [24] G. J. Chen et al., “Synthesis, DNA binding, photo-induced DNA cleavage, cytotoxicity and apoptosis studies of copper(II) complexes,” J. Inorg. Biochem., vol. 105, no. 2, pp. 119–126, 2011.
  • [25] A. M. Pyle, J. P. Rehmann, R. Meshoyrer, N. J. Turro, J. K. Barton, and C. V Kumar, “Mixed-Ligand complexes of ruthenium(II): Factors governing binding to DNA,” J. Am. Chem. Soc., vol. 111, no. 8, pp. 3051–3058, 1989.
  • [26] N. Vamsikrishna, M. P. Kumar, G. Ramesh, N. Ganji, S. Daravath, and Shivaraj, “DNA interactions and biocidal activity of metal complexes of benzothiazole Schiff bases: synthesis, characterization and validation,” J. Chem. Sci., vol. 129, no. 5, pp. 609–622, 2017.
  • [27] R. Prabhakaran et al., “DNA binding, antioxidant, cytotoxicity (MTT, lactate dehydrogenase, NO), and cellular uptake studies of structurally different nickel(II) thiosemicarbazone complexes: Synthesis, spectroscopy, electrochemistry, and X-ray crystallography,” J. Biol. Inorg. Chem., vol. 18, no. 2, pp. 233–247, 2013.
  • [28] J. B. Chaires, “Energetics of drug-DNA interactions,” Biopolymers, vol. 44, no. 3, pp. 201–215, 1997.
  • [29] R. Palchaudhuri and P. J. Hergenrother, “DNA as a target for anticancer compounds: methods to determine the mode of binding and the mechanism of action,” Curr. Opin. Biotechnol., vol. 18, no. 6, pp. 497–503, 2007.
  • [30] R. D. Snyder, J. McNulty, G. Zairov, D. E. Ewing, and L. B. Hendry, “The influence of N-dialkyl and other cationic substituents on DNA intercalation and genotoxicity,” Mutat. Res. - Fundam. Mol. Mech. Mutagen., vol. 578, no. 1–2, pp. 88–99, 2005.
  • [31] R. D. Snyder, “Assessment of atypical DNA intercalating agents in biological and in silico systems,” Mutat. Res. - Fundam. Mol. Mech. Mutagen., vol. 623, no. 1–2, pp. 72–82, 2007.
  • [32] L. Subha, C. Balakrishnan, S. Thalamuthu, and M. A. Neelakantan, “Mixed ligand Cu(II) complexes containing o-vanillin-L-tryptophan Schiff base and heterocyclic nitrogen bases: Synthesis, structural characterization, and biological properties,” J. Coord. Chem., vol. 68, no. 6, pp. 1021–1039, 2015.
  • [33] L. Strekowski and B. Wilson, “Noncovalent interactions with DNA: An overview,” Mutat. Res. - Fundam. Mol. Mech. Mutagen., vol. 623, no. 1–2, pp. 3–13, 2007.
  • [34] H. S. B. N. Sangeetha Gowda K.R., Blessy Baby Mathew, C.N. Sudhamani, “Mechanism of DNA Binding and Cleavage, Biomedicine and Biotechnology,” Biomed. Biotechnol., vol. Vol. 2 No., no. 1, pp. 1–9, 2014.
  • [35] E. Buraka et al., “DNA-binding studies of AV-153, an antimutagenic and DNA repair-stimulating derivative of 1,4-dihydropiridine,” Chem. Biol. Interact., vol. 220, no. 2014, pp. 200–207, 2014.
There are 35 citations in total.

Details

Primary Language English
Subjects Structural Biology
Journal Section Research Articles
Authors

Nuray Yıldırım 0000-0002-4807-5357

Neslihan Demir 0000-0002-2347-8344

Project Number FBA-2017-1125
Publication Date April 15, 2021
Submission Date September 17, 2020
Acceptance Date January 27, 2021
Published in Issue Year 2021

Cite

APA Yıldırım, N., & Demir, N. (2021). DNA Interactions, Mutagenic, Anti-Mutagenic And Antimicrobial Activities of (E)-2-((3,5-Bis(Trifluoromethyl)Phenylimino)Methyl)-4,6- Dimethoxyphenol. Sakarya University Journal of Science, 25(2), 339-348. https://doi.org/10.16984/saufenbilder.793776
AMA Yıldırım N, Demir N. DNA Interactions, Mutagenic, Anti-Mutagenic And Antimicrobial Activities of (E)-2-((3,5-Bis(Trifluoromethyl)Phenylimino)Methyl)-4,6- Dimethoxyphenol. SAUJS. April 2021;25(2):339-348. doi:10.16984/saufenbilder.793776
Chicago Yıldırım, Nuray, and Neslihan Demir. “DNA Interactions, Mutagenic, Anti-Mutagenic And Antimicrobial Activities of (E)-2-((3,5-Bis(Trifluoromethyl)Phenylimino)Methyl)-4,6- Dimethoxyphenol”. Sakarya University Journal of Science 25, no. 2 (April 2021): 339-48. https://doi.org/10.16984/saufenbilder.793776.
EndNote Yıldırım N, Demir N (April 1, 2021) DNA Interactions, Mutagenic, Anti-Mutagenic And Antimicrobial Activities of (E)-2-(3,5-Bis(Trifluoromethyl)Phenylimino)Methyl)-4,6- Dimethoxyphenol. Sakarya University Journal of Science 25 2 339–348.
IEEE N. Yıldırım and N. Demir, “DNA Interactions, Mutagenic, Anti-Mutagenic And Antimicrobial Activities of (E)-2-((3,5-Bis(Trifluoromethyl)Phenylimino)Methyl)-4,6- Dimethoxyphenol”, SAUJS, vol. 25, no. 2, pp. 339–348, 2021, doi: 10.16984/saufenbilder.793776.
ISNAD Yıldırım, Nuray - Demir, Neslihan. “DNA Interactions, Mutagenic, Anti-Mutagenic And Antimicrobial Activities of (E)-2-((3,5-Bis(Trifluoromethyl)Phenylimino)Methyl)-4,6- Dimethoxyphenol”. Sakarya University Journal of Science 25/2 (April 2021), 339-348. https://doi.org/10.16984/saufenbilder.793776.
JAMA Yıldırım N, Demir N. DNA Interactions, Mutagenic, Anti-Mutagenic And Antimicrobial Activities of (E)-2-((3,5-Bis(Trifluoromethyl)Phenylimino)Methyl)-4,6- Dimethoxyphenol. SAUJS. 2021;25:339–348.
MLA Yıldırım, Nuray and Neslihan Demir. “DNA Interactions, Mutagenic, Anti-Mutagenic And Antimicrobial Activities of (E)-2-((3,5-Bis(Trifluoromethyl)Phenylimino)Methyl)-4,6- Dimethoxyphenol”. Sakarya University Journal of Science, vol. 25, no. 2, 2021, pp. 339-48, doi:10.16984/saufenbilder.793776.
Vancouver Yıldırım N, Demir N. DNA Interactions, Mutagenic, Anti-Mutagenic And Antimicrobial Activities of (E)-2-((3,5-Bis(Trifluoromethyl)Phenylimino)Methyl)-4,6- Dimethoxyphenol. SAUJS. 2021;25(2):339-48.

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