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DNA interaction studies of sesamol (3,4-methylenedioxyphenol) food additive

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Abstract

The interaction of native calf thymus DNA (CT-DNA) with sesamol (3,4-methylenedioxyphenol) in Tris–HCl buffer at neutral pH 7.4 was monitored by absorption spectrophotometry, viscometry and spectrofluorometry. It is found that sesamol molecules could interact with DNA outside and/or groove binding modes, as are evidenced by: hyperchromism in UV absorption band, very slow decrease in specific viscosity of DNA, and small increase in the fluorescence of methylene blue (MB)-DNA solutions in the presence of increasing amounts of sesamol, which indicates that it is able to partially release the bound MB. Furthermore, the enthalpy and entropy of the reaction between sesamol and CT-DNA showed that the reaction is enthalpy-favored and entropy-disfavored (ΔH = −174.08 kJ mol−1; ΔS = −532.92 J mol−1 K−1). The binding constant was determined using absorption measurement and found to be 2.7 × 104 M−1; its magnitude suggests that sesamol interacts to DNA with a high affinity.

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References

  1. Elleuch M, Besbes S, Roiseux O, Blecker C, Attia H (2007) Quality characteristics of sesame seeds and by-products. Food Chem 103:641–650

    Article  CAS  Google Scholar 

  2. Kanimozhi P, Prasad NR (2009) Antioxidant potential of sesamol and its role on radiation-induced DNA damage in whole-body irradiated Swiss albino mice. Environ Toxicol Pharmacol 28:192–197

    Article  PubMed  CAS  Google Scholar 

  3. Chopra K, Tiwari V, Arora V, Kuhad A (2010) Sesamol suppresses neuro-inflammatory cascade in experimental model of diabetic neuropathy. J Pain 11(10):950–957

    Article  PubMed  CAS  Google Scholar 

  4. Chang CC, Lu WJ, Chiang CW, Jayakumar T, Ong ET, Hsiao G, Fong TH, Chou DS, Sheu JR (2010) Potent antiplatelet activity of sesamol in an in vitro and in vivo model: pivotal roles of cyclic AMP and p38 mitogen-activated protein kinase. J Nutr Biochem 21(12):1214–1221

    Article  PubMed  CAS  Google Scholar 

  5. Hayes JE, Stepanyan V, Allen P, O’Grady MN, Kerry JP (2010) Effect of lutein, sesamol, ellagic acid and olive leaf extract on the quality and shelf-life stability of packaged raw minced beef patties. Meat Sci 84:613–620

    Article  PubMed  CAS  Google Scholar 

  6. Ismail HA, Lee EJ, Ko KY, Ahn DU (2008) Effects of aging time and natural antioxidants on the color, lipid oxidation and volatiles of irradiated ground beef. Meat Sci 80:582–591

    Article  PubMed  CAS  Google Scholar 

  7. Daly T, Ryan E, Aherne SA, O’Grady MN, Hayes J, Allen P, Kerry JP, O’Brien NM (2010) Bioactivity of ellagic acid-, lutein- or sesamol-enriched meat patties assessed using an in vitro digestion and Caco-2 cell model system. Food Res Int 43:753–760

    Article  CAS  Google Scholar 

  8. Konsoula Z, Liakopoulou-Kyriakides M (2010) Effect of endogenous antioxidants of sesame seeds and sesame oil to the thermal stability of edible vegetable oils. LWT: Food Sci Technol 43:1379–1386

    Article  CAS  Google Scholar 

  9. Ahmad S, Yousuf S, Ishrat T, Khan MB, Bhatia K, Fazli IS, Khan JS, Ansari NH, Islam F (2006) Effect of dietary sesame oil as antioxidant on brain hippocampus of rat in focal cerebral ischemia. Life Sci 79:1921–1928

    Article  PubMed  CAS  Google Scholar 

  10. Fujimoto A, Shingai Y, Oyama TB, Kawanai T, Hashimoto E, Koizumi K, Kimura K, Masuda T, Oyama Y (2010) Apoptosis-inducing action of two products from oxidation of sesamol, an antioxidative constituent of sesame oil: a possible cytotoxicity of oxidized antioxidant. Toxicol In Vitro 24:1720–1726

    Article  PubMed  CAS  Google Scholar 

  11. Hiros M, Fukushima S, Shirai T, Hasegawa R, Kato T, Tanaka H, Asakawa E, Ito N, Jpn J (1990) Stomach carcinogenicity of caffeic acid, sesamol and catechol in rats and mice. Cancer Res 81:207–212

    Google Scholar 

  12. Kashanian S, Ezzati Nazhad Dolatabadi J (2009) DNA binding studies of 2-tert-butylhydroquinone (TBHQ) food additive. Food Chem 116:743–747

    Article  CAS  Google Scholar 

  13. Liu J, Zhang T, Lu T, Qu L, Zhou H, Zhang Q, Ji L (2002) DNA-binding and cleavage studies of macrocyclic copper(II) complexes. Inorg Biochem 91:269–276

    Article  CAS  Google Scholar 

  14. Liu Z-Q, Li Y-T, Wu Z-Y, Zhang S-F (2009) [Cu4(H2O)4(dmapox)2(btc)]n -10nH2O: the first two-dimensional polymeric copper(II) complex with bridging l-trans-oxamidate and μ4-1,2,4,5-benzentetracarboxylato ligands: synthesis, crystal structure and DNA binding studies. Inorg Chim Acta 362:71–77

    Article  CAS  Google Scholar 

  15. Kashanian S, Khodaei MM, Roshanfekr H, Shahabadi N, Rezvani A, Mansouri Gh (2010) DNA-binding, DNA cleavage and cytotoxicity studies of new copper(II) complexes. DNA Cell Biol 30:287–296

    Article  Google Scholar 

  16. Tan L-F, Chao H (2007) DNA-binding and photocleavage studies of mixed polypyridyl ruthenium(II) complexes with calf thymus DNA. Inorg Chim Acta 360:2016–2022

    Article  CAS  Google Scholar 

  17. Wang X-L, Chao H, Li H, Hong X-L, Liu Y-J, Tan L-F, Ji L-N (2004) DNA interactions of cobalt(III) mixed-polypyridyl complexes containing asymmetric ligands. Inorg Biochem 98:1143–1150

    Article  CAS  Google Scholar 

  18. Xi P-X, Xu Z-H, Liu X-H, Cheng F-J, Zeng Z–Z (2008) Synthesis, characterization and DNA-binding studies of 1-cyclohexyl-3-tosylurea and its Ni(II), and Cd(II) complexes. Spectrochimica Acta Part A 71:523–528

    Article  Google Scholar 

  19. Shahabadi N, Kashanian S, Darabi F (2010) DNA binding and DNA cleavage studies of a water soluble cobalt(II) complex containing dinitrogen Schiff base ligand: the effect of metal on the mode of binding. Eur J Med Chem 45:4239–4245

    Article  PubMed  CAS  Google Scholar 

  20. Kashanian S, DolatabadiJ Ezzati Nazhad (2010) In vitro studies on calf thymus DNA interaction and 2-tert-butyl-4-methylphenol food additive. Eur Food Res Technol 230(6):821–825

    Article  CAS  Google Scholar 

  21. Ling X, Zhong W, Huang Q, Ni K (2008) Spectroscopic studies on the interaction of pazufloxacin with calf thymus DNA. J Photochem Photobiol B 93:172–176

    Article  PubMed  CAS  Google Scholar 

  22. Kashanian S, Khodaei MM, Pakravan P (2010) Spectroscopic Studies on the Interaction of Isatin with Calf Thymus DNA. DNA Cell Biol 29:639–646

    Article  PubMed  CAS  Google Scholar 

  23. Shahabadi N, Kashanian S, Khosravi M, Mahdavi M (2010) Multispectroscopic DNA interaction studies of a water-soluble nickel(II) complex containing different dinitrogen aromatic ligands. Transition Met Chem 35:699–705

    Article  CAS  Google Scholar 

  24. Kashanian S, Askari S, Ahmadi F, Omidfar K, Ghobadi S, Abasi Tarighat F (2008) In vitro study of DNA interaction with clodinafop–propargyl herbicide. DNA Cell Biol 27(10):581–586

    Article  PubMed  CAS  Google Scholar 

  25. Nafisi Sh, Saboury AA, Keramat N, Neault JF, Tajmir-Raihi HA (2007) Stability and structural features of DNA intercalation with ethidium bromide, acridine orange and methylene blue. Mol Struct 827:35–43

    Article  CAS  Google Scholar 

  26. Xu ZH, Chen FJ, Xi PX, Liu XH, Zeng ZZ (2008) Synthesis, characterization, and DNA-binding properties of the cobalt(II) and nickel(II) complexes with salicylaldehyde 2-phenylquinoline-4-carboylhydrazone. J Photochem Photobiol A Chem 196:77–83

    Article  CAS  Google Scholar 

  27. Kashanian S, Heidary Zeidali S (2011) DNA binding studies of tartrazine food additive. DNA Cell Biol 30:499–505

    Article  PubMed  CAS  Google Scholar 

  28. Kashanian S, Shahabadi N, Roshnfekr H, Shalmashi K, Omidfar K (2008) DNA binding studies of PdCl2(LL) (LL = chelating diamine ligand: N,N-dimethyl trimethylen diamine) complex. Biochemistry (Moscow) 73(8):929–936

    Article  CAS  Google Scholar 

  29. Mahadevan S, Palaniandavar M (1997) Spectroscopic and voltammetric study on copper complexes of 2/9-dimethyl-1/10-phenanthrolines bound to calf thymus DNA. Inorg Chim Acta 254:291–302

    Article  Google Scholar 

  30. Shahabadi N, Kashanian S, Darabi F (2009) In vitro study of DNA interaction with a water-soluble dinitrogen schiff base. DNA Cell Biol 28:589–596

    Article  PubMed  CAS  Google Scholar 

  31. Chen F, Xu Z, Xi P, Liu X, Zeng Z (2009) DNA-binding and cleavage studies of a novel two-dimensional manganese(II) azide complex with N-Methylimidazole. Anal Sci 25:359–363

    Article  PubMed  Google Scholar 

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Authors and Affiliations

  1. Faculty of Chemistry, Sensor and Biosensor Research Center (SBRC) & Nanoscience and Nanotechnology Research Center (NNRC) Razi University, Kermanshah, P.O. Box: 67149, Islamic Republic of Iran

    Soheila Kashanian

  2. Department of Biology, Faculty of Science, Razi University, Kermanshah, Islamic Republic of Iran

    Ameneh Tahmasian Ghobadi & Zohreh Shariati

  3. Department of Chemistry, Islamic Azad University, Ilam Branch, Ilam, Islamic Republic of Iran

    Hamideh Roshanfekr

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  1. Soheila Kashanian
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  2. Ameneh Tahmasian Ghobadi
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  3. Hamideh Roshanfekr
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  4. Zohreh Shariati
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Correspondence to Soheila Kashanian.

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Kashanian, S., Tahmasian Ghobadi, A., Roshanfekr, H. et al. DNA interaction studies of sesamol (3,4-methylenedioxyphenol) food additive. Mol Biol Rep 40, 1173–1179 (2013). https://doi.org/10.1007/s11033-012-2159-x

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  • DOI: https://doi.org/10.1007/s11033-012-2159-x

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