Study of the DNA damage and cell death in human peripheral blood mononuclear and HepG2/C3A cells exposed to the synthetic 3-(3-hydroxyphenyl)-7-hydroxycoumarin

References

• Al-Haiza, M. A., M. S. Mostafa, and M. Y. El-Kady. 2003. “Synthesis and Biological Evaluation of Some New Coumarin Derivatives.” Molecules 8 (2): 275–286. https://doi.org/10.3390/80200275.
   Web of Science ®Google Scholar
• Alshibl, H. M., E. S. Al-Abdullah, M. E. Haiba, H. M. Alkahtani, G. E. A. Awad, A. H. Mahmoud, B. M. M. Ibrahim, A. Bari, and A. Villinger. 2020. “Synthesis and Evaluation of New Coumarin Derivatives as Antioxidant, Antimicrobial, and Anti-Inflammatory Agents.” Molecules (Basel, Switzerland) 25 (14): 3251. https://doi.org/10.3390/molecules25143251.
   PubMed Web of Science ®Google Scholar
• Annunziata, F., C. Pinna, S. Dallavalle, L. Tamborini, and A. Pinto. 2020. “An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities.” International Journal of Molecular Sciences 21 (13): 4618. https://doi.org/10.3390/ijms21134618.
   PubMed Web of Science ®Google Scholar
• Araldi, R. P., T. C. de Melo, T. B. Mendes, P. L. de Sá Júnior, B. H. Nozima, E. T. Ito, R. F. de Carvalho, E. B. Souza, and R. Cassia-Stocco. 2015. “Using the Comet and Micronucleus Assays for Genotoxicity Studies: A Review.” Biomedicine & Pharmacotherapy 72:74–82. https://doi.org/10.1016/j.biopha.2015.04.004.
   PubMed Web of Science ®Google Scholar
• Araújo, J. R. S., J. G. S. Morais, C. M. Santos, K. C. A. Rocha, A. C. A. R. Fagundes, F. A. Silva-Filho, F. A. Martins, and P. M. Almeida. 2021. “Phytochemical Prospecting, Isolation, and Protective Effect of the Ethanolic Extract of the Leaves of Jatropha mollissima (Pohl) Baill.” Journal of Toxicology and Environmental Health Part A 84 (18): 743–760. https://doi.org/10.1080/15287394.2021.1938767.
   PubMed Web of Science ®Google Scholar
• Azqueta, A., H. Stopper, B. Zegura, M. Dusinska, and P. Peter-Møller. 2022. “Do Cytotoxicity and Cell Death Cause False Positive Results in the In Vitro Comet Assay?” Mutation Research/Genetic Toxicology and Environmental Mutagenesis 881:503520. https://doi.org/10.1016/j.mrgentox.2022.503520.
   PubMed Web of Science ®Google Scholar
• Baillie, T. A. 2008. “Metabolism and Toxicity of Drugs. Two Decades of Progress in Industrial Drug Metabolism.” Chemical Research in Toxicology 21:129–137. https://doi.org/10.1021/tx7002273.
   PubMed Web of Science ®Google Scholar
• Bhattarai, N., A. A. Kumbhar, Y. R. Pokharel, and P. N. Yadav. 2021. “Anticancer Potential of Coumarin and Its Derivatives.” Mini-Reviews in Medicinal Chemistry 21 (19): 2996–3029. https://doi.org/10.2174/1389557521666210405160323.
   PubMed Web of Science ®Google Scholar
• Borges, F., F. Roleira, N. Milhanzes, L. Santana, and E. Uriarte. 2005. “Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity.” Current Medicinal Chemistry 12 (8): 887–916. https://doi.org/10.2174/0929867053507315.
   PubMed Web of Science ®Google Scholar
• Born, S. L., J. K. Hu, and L. D. Lehman-Mckeeman. 2000. “O-Hydroxyphenylacetaldehyde Is a Hepatotoxic Metabolite of Coumarin.” Drug Metabolism and Disposition: The Biological Fate of Chemicals 28 (2): 218–223.
   PubMed Web of Science ®Google Scholar
• Castanha, A. P. M., L. M. Almeida-Terassi, E. Guardado-Yordi, M. J. Matos, and E. L. Maistro. 2023. “Cytogenotoxicity Assessment of 3-(3,4-Dihydroxyphenyl)-7,8-Dihydroxycoumarin on HepG2/C3A Cells and Leukocytes.” Journal of Applied Toxicology 43 (2): 323–334. https://doi.org/10.1002/jat.4384.
   PubMed Web of Science ®Google Scholar
• Cheke, R. S., H. M. Patel, V. M. Patil, I. A. Ansari, J. P. Ambhore, S. D. Shinde, A. Kadri, et al. 2022. “Molecular Insights into Coumarin Analogues as Antimicrobial Agents: Recent Developments in Drug Discovery.” Antibiotics 11 (5): 566. https://doi.org/10.3390/antibiotics11050566.
   Google Scholar
• Chuang, J. Y., Y. F. Huang, H. F. Lu, H. C. Ho, J. S. Yang, T. M. Li, N. W. Chang, and J. G. Chung. 2007. “Coumarin Induces Cell Cycle Arrest and Apoptosis in Human Cervical Cancer HeLa Cells Through a Mitochondria- and Caspase-3 Dependent Mechanism and NF-kappaB Down-Regulation.” Vivo 21 (6): 1003–1009.
   PubMed Web of Science ®Google Scholar
• Chu, C. Y., Y. Y. Tsai, C. J. Wang, W. L. Lin, and T. H. Tseng. 2001. “Induction of Apoptosis by Esculetin in Human Leukemia Cells.” European Journal of Pharmacology 416 (1–2): 25–32. https://doi.org/10.1016/S0014-2999(01)00859-7.
   PubMed Web of Science ®Google Scholar
• Costa, T. M., L. B. B. Tavares, and D. Oliveira. 2016. “Fungi as a Source of Natural Coumarins Production.” Applied Microbiology and Biotechnology 100 (15): 6571–6584. https://doi.org/10.1007/s00253-016-7660-z.
   PubMed Web of Science ®Google Scholar
• Crowley, L. C., B. J. Marfell, M. E. Christensen, and N. J. Waterhouse. 2016. “Measuring Cell Death by Trypan Blue Uptake and Light Microscopy.” Cold Spring Harbor Protocols 2016 (7): pdb.prot087155. https://doi.org/10.1101/pdb.prot087155.
   Google Scholar
• Fais, A., B. Era, S. Asthana, V. Sogos, R. Medda, L. Santana, E. Uriarte, M. J. Matos, F. Delogu, and A. Kumar. 2018. “Coumarin Derivatives as Promising Xanthine Oxidase Inhibitors Int.” International Journal of Biological Macromolecules 120:1286–1293. https://doi.org/10.1016/j.ijbiomac.2018.09.001.
   PubMed Web of Science ®Google Scholar
• Fenech, M. 2000. “The in vitro micronucleus technique.” Mutat. Res 455: 81–95.
   PubMed Web of Science ®Google Scholar
• Fort, D. J., E. L. Stover, T. Propst, M. A. Hull, and J. A. Bantle. 1998. “Evaluation of the Developmental Toxicities of Coumarin, 4-Hydroxycoumarin, and 7-Hydroxycoumarin Using FETAX.” Drug and Chemical Toxicology 21 (1): 15–26. https://doi.org/10.3109/01480549809017847.
   PubMed Web of Science ®Google Scholar
• Fylaktakidou, K. C., D. J. Hadipavlou-Litina, K. E. Litinas, and D. N. Nicolaides. 2004. “Natural and Synthetic Coumarin Derivatives with Anti-Inflammatory/antioxidant Activities.” Current Pharmaceutical Design 10 (30): 3813–3833. https://doi.org/10.2174/1381612043382710.
   PubMed Web of Science ®Google Scholar
• Gaspar, A., M. J. Matos, J. Garrido, E. Uriarte, and F. Borges. 2014. “Chromone: A Valid Scaffold in Medicinal Chemistry.” Chemical Reviews 114 (9): 4960–4992. https://doi.org/10.1021/cr400265z.
   PubMed Web of Science ®Google Scholar
• Goel, A., A. K. Prasad, V. S. Parmar, B. Ghosh, and N. Saini. 2009. “Apoptogenic Effect of 7,8-Diacetoxy-4-Methylcoumarin and 7,8-Diacetoxy-4-Methylthiocoumarin in Human Lung Adenocarcinoma Cell Line: Role of NF-κB, Akt, ROS and MAP Kinase Pathway.” Chemico-Biological Interactions 179 (2–3): 363–374. https://doi.org/10.1016/j.cbi.2008.10.060.
   PubMed Web of Science ®Google Scholar
• Guardado-Yordi, E., E. Molina, A. Pérez, L. León, L. Santana, E. Uriarte, and M. J. Matos. 2017. “QSAR Study of Synthetic 3-Arylcoumarins: In Silico Clastogenic Prediction.” International Electronic Conferences on Synthetic Organic Chemistry 20:1–30.
   Google Scholar
• Hartmann, A., and G. Speit. 1997. “The Contribution of Cytotoxicity to DNA-Effects in the Single Cell Gel Test (Comet Assay).” Toxicology Letters 90 (2–3): 183–188. https://doi.org/10.1016/S0378-4274(96)03847-7.
   PubMed Web of Science ®Google Scholar
• Harvey, R. G., C. Cortex, T. P. Ananthanarayan, and S. Schmolka. 1988. “A New Coumarin Synthesis and Its Utilization for the Synthesis of Polycyclic Coumarin Compounds with Anticarcinogenic Properties.” The Journal of Organic Chemistry 53 (17): 3936–3943. https://doi.org/10.1021/jo00252a011.
   Web of Science ®Google Scholar
• Hewitt, N. J., and P. Hewitt. 2004. “Phase I and II Enzyme Characterization of Two Sources of HepG2 Cell Lines.” Xenobiotica 34 (3): 243–256. https://doi.org/10.1080/00498250310001657568.
   PubMed Web of Science ®Google Scholar
• Jing, W., C. Liu, C. Su, L. Liu, P. Chen, X. Li, X. Zhang, B. Yuan, H. Wang, and X. Du. 2023. “Role of Reactive Oxygen Species and Mitochondrial Damage in Rheumatoid Arthritis and Targeted Drugs.” Frontiers in Immunology 14:1107670. https://doi.org/10.3389/fimmu.2023.1107670.
   PubMedGoogle Scholar
• Jung, J., J. Kin, and O. S. Park. 2001. “A Convenient One-Pot Synthesis of 4-Hydroxycoumarin, 4-Hydroxythiocoumarin, and 4-Hydroxyquinolin-2(1H)-One.” Synthetic Communications 31 (8): 1195–1200. https://doi.org/10.1081/SCC-100104003.
   Web of Science ®Google Scholar
• Kostova, I., G. Momekov, T. Tzanova, and M. Karaivanova. 2006. “Synthesis, Characterization, and Cytotoxic Activity of New Lanthanum (III) Complexes of Bis-Coumarins.” Bioinorganic Chemistry and Applications 25651:1–9. https://doi.org/10.1155/BCA/2006/25651.
   Google Scholar
• Kumar, A., and V. Jaitak. 2019. “Natural Products as Multidrug Resistance Modulators in Cancer.” European Journal of Medicinal Chemistry 176:268–291. https://doi.org/10.1016/j.ejmech.2019.05.027.
   PubMed Web of Science ®Google Scholar
• Kumar, P., A. Nagarajan, and P. D. Uchil. 2018. “Analysis of Cell Viability by the MTT Assay.” Cold Spring Harbor Protocols 2018 (6): db.prot095505. https://doi.org/10.1101/pdb.prot095505.
   Google Scholar
• Küpeli-Akkol, E., Y. Genç, B. Karpuz, E. Sobarzo-Sánchez, and R. Capasso. 2020. “Coumarins and Coumarin-Related Compounds in Pharmacotherapy of Cancer.” Cancers (Basel) 12 (7): 1959. https://doi.org/10.3390/cancers12071959.
   PubMed Web of Science ®Google Scholar
• Li, Z., D. Kong, Y. Liu, and M. Li. 2021. “Pharmacological Perspectives and Molecular Mechanisms of Coumarin Derivatives Against Virus Disease.” Genes & Diseases 209 (1): 80–94. https://doi.org/10.1016/j.gendis.2021.03.007.
   Google Scholar
• Li, Q., L. Wei, J. Zhang, G. Gu, and Z. Guo. 2019. “Significantly Enhanced Antioxidant Activity of Chitosan Through Chemical Modification with Coumarins.” Polymer Chemistry 10 (12): 1480–1488. https://doi.org/10.1039/C8PY01790E.
   Web of Science ®Google Scholar
• Loeb, L. A. 2008. “Cancer Exhibit a Mutator Phenotype: Clinical Implications.” Cancer Research 68 (10): 3551–3557. https://doi.org/10.1158/0008-5472.CAN-07-5835.
   PubMed Web of Science ®Google Scholar
• Madhavan, G. R., V. Balraju, B. Mallesham, R. Chakrabarti, and V. B. Lohray. 2003. “Novel Coumarin Derivatives of Heterocyclic Compounds as Lipid-Lowering Agents.” Bioorganic & Medicinal Chemistry Letters 13 (15): 2547–2551. https://doi.org/10.1016/S0960-894X(03)00490-6.
   PubMed Web of Science ®Google Scholar
• Matos, M. J., F. Mura, S. Vazquez-Rodriguez, F. Borges, L. Santana, E. Uriarte, and C. Olea-Azar. 2015. “Study of Coumarin-Resveratrol Hybrids as Potent Antioxidant Compounds.” Molecules 20 (2): 3290–3308. https://doi.org/10.3390/molecules20023290.
   PubMed Web of Science ®Google Scholar
• Matos, M. J., P. Novo, L. Mayán, I. Torres, E. Uriarte, M. Yáñez, J. A. Fontenla, Fontenla, JÁ, Ortuso F, Alcaro S, Procopio F, Rodríguez-Franco, MI. 2023. “8-Amide and 8-Carbamate Substitution Patterns as Modulators of 7-Hydroxy-4-Methylcoumarin’s Antidepressant Profile: Synthesis, Biological Evaluation and Docking Studies.” European Journal of Medicinal Chemistry 248:115091. https://doi.org/10.1016/j.ejmech.2023.115091.
   PubMed Web of Science ®Google Scholar
• Matos, M. J., F. Pérez-Cruz, S. Vazquez-Rodriguez, E. Uriarte, L. Santana, F. Borges, and C. Olea-Azar. 2013. “Remarkable Antioxidant Properties of a Series of Hydroxy-3-Arylcoumarins.” Bioorganic & Medicinal Chemistry 21 (13): 3900–3906. https://doi.org/10.1016/j.bmc.2013.04.015.
   PubMed Web of Science ®Google Scholar
• Matos, M. J., E. Uriarte, and L. Santana. 2021. “3-Phenylcoumarins as a Privileged Scaffold in Medicinal Chemistry: The Landmarks of the Past Decade.” Molecules 26 (21): 6755. https://doi.org/10.3390/molecules26216755.
   PubMed Web of Science ®Google Scholar
• Moffet, R. S. 1964. “Central Nervous System Depressants. VII. 1 Pyridyl Coumarins.” Journal of Medicinal Chemistry 7 (4): 446–449. https://doi.org/10.1021/jm00334a010.
   PubMed Web of Science ®Google Scholar
• Mosmann, T. 1983. “Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays.” Journal of Immunological Methods 65 (1–2): 55–63. https://doi.org/10.1016/0022-1759(83)90303-4.
   PubMed Web of Science ®Google Scholar
• Murray, R. D. H. 1978. Naturally Occurring Plant Coumarins, 200–209. 1st ed. New York: Springer, Verlag.
   Google Scholar
• Musa, M. A., V. L. Badisa, L. M. Latinwo, T. A. Patterson, and M. A. Owens. 2012. “Coumarin-Based Benzopyranone Derivatives Induced Apoptosis in Human Lung (A549) Cancer Cells.” Anticancer Research 32 (10): 4271–4276.
   PubMed Web of Science ®Google Scholar
• Musiciki, B., A. M. Periers, P. Laurin, D. Ferroud, Y. Benedetti, S. Lachaud, F. Chatreaux, et al. 2000. “Improved Antibacterial Activities of Coumarin Antibiotics Bearing 5′,5′-Dialkylnoviose: Biological Activity of RU79115.” Bioorganic & Medicinal Chemistry Letters 10 (15): 1695–1699. https://doi.org/10.1016/S0960-894X(00)00304-8.
   PubMed Web of Science ®Google Scholar
• OECD, TG 487. 2016. “Guidelines for the Testing of Chemicals.” In Vitro Mammalian Cell Micronucleus Test, Paris: OECD Publishing. https://www.oecd-ilibrary.org/docserver/9789264264861-en.pdf?expires=1698341887&id=id&accname=guest&checksum=09BAC7689422AA437B189E144817BDB4.
   Google Scholar
• OECD, TG 489. 2016. “Guidelines for the Testing of Chemicals.” In Vivo Mammalian Alkaline Comet Assay, Paris: OECD Publishing. https://www.oecd.org/env/test-no-489-in-vivo-mammalian-alkaline-comet-assay-9789264264885-en.htm.
   Google Scholar
• Pitaro, M., N. Croce, V. Gallo, A. Arienzo, G. Salvatore, and G. Antonini. 2022. “Coumarin-Induced Hepatotoxicity: A Narrative Review.” Molecules (Basel, Switzerland) 27 (24): 9063. https://doi.org/10.3390/molecules27249063.
   PubMed Web of Science ®Google Scholar
• Sawecka, J., B. Golos, and J. Malec. 1986. “Mechanism of Unbalanced Growth-Induced Cell Damage. II. A Probable Relationship Between Unbalanced Growth, DNA Breakage and Cell Death.” Chemico-Biological Interactions 60 (1): 47–55. https://doi.org/10.1016/0009-2797(86)90016-5.
   PubMed Web of Science ®Google Scholar
• Shokoohinia, Y., L. Hosseinzadeh, M. Alipour, A. Mostafaie, and H. R. Mohammadi-Motlagh. 2014. “Comparative Evaluation of Cytotoxic and Apoptogenic Effects of Several Coumarins on Human Cancer Cell Lines: Osthole Induces Apoptosis in p53 deficient H1299 Cells.” Advances in Pharmacological Sciences 2014:1–8. https://doi.org/10.1155/2014/847574.
   Google Scholar
• Silva, E. S., M. J. Matos, and E. L. Maistro. 2023. “Evaluation of In Vitro Cytotoxic and Genotoxic Effects of the 3-(3,4-Dihydroxyphenyl)-8-Hydroxycoumarin.” Journal of Applied Toxicology 2023:1–11. https://doi.org/10.1002/jat.4479.
   Google Scholar
• Soto-Nuñez, M., K. Díaz-Morales, P. Cuautle-Rodríguez, V. Torres-Flores, J. S. Lopez-González, J. J. Mandoki-Weitzner, and J. A. Molina-Guarneros. 2015. “Single-Cell Microinjection Assay Indicates That 7-Hydroxycoumarin Induces Rapid Activation of Caspase-3 in A549 Cancer Cells.” Experimental and Therapeutic Medicine 10 (5): 1789–1795. https://doi.org/10.3892/etm.2015.2765.
   PubMed Web of Science ®Google Scholar
• Srikrishna, D., C. Godugu, and P. K. Dubey. 2016. “A Review on Pharmacological Properties of Coumarins.” Mini Reviews in Medicinal Chemistry 16:1–1. https://doi.org/10.2174/1389557516666160801094919.
   Google Scholar
• Stefanachi, A., F. Leonetti, L. Pisani, M. Catto, and A. Carotti. 2018. “Coumarin: A Natural, Privileged and Versatile Scaffold for Bioactive Compounds.” Molecules 23 (2): 250. https://doi.org/10.3390/molecules23020250.
   PubMed Web of Science ®Google Scholar
• Stratton, M. R., P. J. Campbell, and P. A. Futreal. 2009. “The Cancer Genome.” Nature 458 (7239): 719–724. https://doi.org/10.1038/nature07943.
   PubMed Web of Science ®Google Scholar
• Tanaka, Y., W. Fujii, H. Hori, Y. Kitagawa, and K. Ozaki. 2016. “Relationship Between Coumarin-Induced Hepatocellular Toxicity and Mitochondrial Function in Rats.” Food & Chemical Toxicology 90:1–9. https://doi.org/10.1016/j.fct.2016.01.007.
   PubMed Web of Science ®Google Scholar
• Tice, R. R., E. Agurell, D. Anderson, B. Burlinson, A. Hartmann, H. Kobayashi, Y. Miyamae, E. Rojas, J. C. Ryu, and Y. F. Sasaki. 2000. “Single Cell Gel/Comet Assay: Guidelines for In Vitro and In Vivo Genetic Toxicology Testing.” Environmental and Molecular Mutagenesis 35 (3): 206–221. https://doi.org/10.1002/(SICI)1098-2280(2000)35:3<206:AID-EM8>3.0.CO;2-J.
   PubMed Web of Science ®Google Scholar
• Tosun, A., E. Kupelı, and E. Yesılada. 2009. “Anti-Inflammatory and Antinociceptive Activity of Coumarins from Seseli Gummiferum Subsp. Corymbosum (Apiaceae).” Zeitschrift für Naturforschung C 64 (1–2): 56–62. https://doi.org/10.1515/znc-2009-1-210.
   PubMed Web of Science ®Google Scholar
• Traykova, M., and I. Kostova. 2005. “Coumarin Derivatives and Oxidative Stress.” International Journal of Pharmacology 1 (1): 29–32. https://doi.org/10.3923/ijp.2005.29.32.
   Google Scholar
• Véras, J. H., C. R. Vale, E. F. L. C. Bailão, M. M. Anjos, C. G. Cardoso, M. G. Oliveira, J. R. Paula, G. R. Oliveira, C. R. Ribeiro-Silva, and L. Chen-Chen. 2022. “Protective Effects and DNA Repair Induction of a Coumarin-Chalcone Hybrid Against Genotoxicity Induced by Mutagens.” Journal of Toxicology and Environmental Health Part A 85 (22): 937–951. https://doi.org/10.1080/15287394.2022.2120585.
   PubMed Web of Science ®Google Scholar
• Vianna, D. R., L. Hamerski, F. Figueiró, A. Bernardi, L. C. Visentin, E. N. Pires, H. F. Teixeira, et al. 2012. “Selective Cytotoxicity and Apoptosis Induction in Glioma Cell Lines by 5-Oxygenated-6,7-Methylenedioxycoumarins from Pterocaulon Species.” European Journal of Medicinal Chemistry 57:268–274. https://doi.org/10.1016/j.ejmech.2012.09.007.
   PubMed Web of Science ®Google Scholar
• Weigta, S., N. Hueblera, R. Streckerb, T. Braunbeckb, and T. H. Broscharda. 2012. “Developmental Effects of Coumarin and the Anticoagulant Coumarin Derivative Warfarin on Zebrafish (Danio rerio) Embryos.” Reproductive Toxicology (Elmsford, NY) 33 (2): 133–141. https://doi.org/10.1016/j.reprotox.2011.07.001.
   PubMed Web of Science ®Google Scholar
• Williams, J. R., J. B. Little, and W. U. Shipley. 1974. “Association of Mammalian Cell Death with a Specific Endonucleolytic Degradation of DNA.” Nature 252 (5485): 754–755. https://doi.org/10.1038/252754a0.
   PubMed Web of Science ®Google Scholar
• Zhang, L., G. Jiang, F. Yao, Y. He, G. Liang, Y. Zhang, B. Hu, et al. 2012. “Growth Inhibition and Apoptosis Induced by Osthole, a Natural Coumarin, in Hepatocellular Carcinoma.” PloS One 7 (5): e37865. https://doi.org/10.1371/journal.pone.0037865.
   PubMed Web of Science ®Google Scholar
• Zheng, S. Y. 2012. “Anticancer Effect and Apoptosis Induction by Quercetin in the Human Lung Cancer Cell Line A-549.” Molecular Medicine Reports 5:822–826. https://doi.org/10.3892/mmr.2011.726.
   PubMed Web of Science ®Google Scholar
• Zhu, J. J., and J. G. Jiang. 2018. “Pharmacological and Nutritional Effects of Natural Coumarins and Their Structure–Activity Relationships.” Molecular Nutrition & Food Research 62 (14): e1701973. https://doi.org/10.1002/mnfr.201701073.
   Web of Science ®Google Scholar