DNA damage induced by resveratrol and its synthetic analogues in the presence of Cu (II) ions: Mechanism and structure-activity relationship |
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| Affiliation: | 1. Institute of Biophysics of the CAS, v.v.i.; Královopolská 135, 612 65 Brno, Czech Republic;2. Institute of Analytical Chemistry of the CAS, v.v.i.; Veveří 97, 602 00 Brno, Czech Republic;1. College of Electronic and Information Engineering, Shandong University of Science and Technology, Qingdao, 266590 Shandong, People''s Republic of China;2. College of Science, China University of Petroleum(East China), Qingdao, 266580 Shandong, People''s Republic of China;3. College of Electrical Engineering and Automation, Shandong University of Science and Technology, Qingdao, 266590 Shandong, People''s Republic of China;1. Division of Vascular Diseases and Surgery, The Ohio State University Wexner Medical Center, Columbus, OH;2. Division of Vascular Surgery, University of Texas Health Science Center at San Antonio, San Antonio, TX;1. Department of Physics, Faculty of Sciences, University of Zanjan, Zanajn, Iran;2. Department of Medical Physics and Biomedical Engineering, School of Medicine, Shahid Beheshti University of Medical Science, Tehran, Iran |
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| Abstract: | The prooxidant effect of resveratrol (3,5,4′-trihydroxy-trans-stibene) and its synthetic analogues (ArOH), that is, 3,4,4′-trihydroxy-trans-stibene (3,4,4′-THS), 3,4,5-trihydroxy-trans-stibene (3,4,5-THS), 3,4-dihydroxy-trans-stibene (3,4-DHS), 4,4′-dihydroxy-trans-stibene (4,4′-DHS), 2,4-dihydroxy-trans-stilbene (2,4-DHS), 3,5-dihydroxy-trans-stilbene (3,5-DHS) and 3,5,4′-trimethoxy-trans-stibene (3,5,4′-TMS), on supercoiled pBR322 plasmid DNA strand breakage and calf thymus DNA damage in the presence of Cu (II) ions has been studied. It was found that the compounds bearing ortho-dihydroxyl groups (3,4-DHS, 3,4,4′-THS, and 3,4,5-THS) or bearing 4-hydroxyl groups (2,4-DHS, 4,4′-DHS, and resveratrol) exhibit remarkably higher activity in the DNA damage than the ones bearing no such functionalities. Kinetic analysis by UV-visible spectra demonstrates that the formation of ArOH-Cu (II) complexes, the stabilization of oxidative intermediate derived from ArOH and Cu (II)/Cu (I) redox cycles, might be responsible for the DNA damage. This study also reveals a good correlation between antioxidant and prooxidant activity, as well as cytotoxicity against human leukemia (HL-60 and Jurkat) cell lines. The mechanisms and implications of these observations are discussed. |
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