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Electrochemical Comparison of the Interaction of 5-Nitrouracil with Single- or Double-Stranded DNA at mercury and glassy carbon electrodes

Yıl 2014, Cilt: 2 Sayı: 1, 1 - 8, 01.04.2014
https://doi.org/10.5505/apjes.2014.46855

Öz

The interaction of the 5-Nitrouracil (5NU), with ss-, and ds-DNA was investigated electrochemically in absence and presence of copper ions by using cyclic voltammetry (CV) and differential pulse stripping voltammetry (DPSV) at hanging mercury drop electrode (HMDE) and glassy carbon electrode (GCE) surfaces. It was found that, in absence of copper ions, the addition of ss- or ds-DNA to a buffered solution of 5NU results in a decrease on the 5NU redox peak current with a remarkable change in the peak potential (ca. 150 mV vs. Ag/AgCl) at both electrodes. This means that, an interaction of 5NU molecules with both ss- and ds-DNA was observed. The results also demonstrate that a distinguish between ss-, and ds-DNA can be achieved in presence of copper ion through their interaction with 5NU. The binding constants of 5NU with ds-DNA at HMDE and GCE were determined through the changes on the 5NU redox peak currents (at HMDE, 1.45x10^5 and at GCE, 2.65x10^5). The calibration plot for the DNA determination was obtained through the corresponding decreases on the DPSV peak current of 5NU to different additions of DNA (ss- or ds-DNA) concentration levels at the optimum conditions.

Kaynakça

  • Pharmacology, 6th ed. (Appleton & Lang, Norwalk,CT; 1995.
  • Lawrence TS, Davis MA, Maybaum J, Stetson PL, Ensminger WD. The Effect of Single versus Halogenated Radiosensitization and DNA Strand Breakage in Human Tumor Cells. Radiat Res 1990; 123: 192- Basic and Clinical Double-Strand Substitution Pyrimidine-Induced
  • Jain KS, Chitre TS, Miniyar PB, Kathiaravan MK, Bendre VS, Veer VS, et al. Biological and medicinal significance of pyrimidines. J Curr Sci 2006; 90(6):793-803.
  • Longley DB, Harkin DP, Johnston PG. 5- Fluorouracil: mechanisms of action and clinical strategies. Nat Rev Can 2003; 3:330-8.
  • Buchsbaum DJ, Khazaeli MB, Davis MA, Lawrence TS. Sensitization of radiolabeled monoclonal bromodeoxyuridine.Cancer 1994; 73: 999-1005.
  • Chelladurai M, Lobocki CA, Sultani M, Hanna Y, Drelichman A, Pieper DR, et al. Bromodeoxyuridine improves the cytotoxic effect of cisplatin: a comparison with 5-fluorouracil. Cancer Chemother Pharmacol 1997; 40(6):463-8.
  • Wardman P, Clarke ED, Flockhart IR, Wallace RG. The rationale for the development of improved hypoxic cell radiosensitizers. Brit J Cancer 1978 (Suppl. III) 1-5.
  • Lee BH, Shin JH, Lim MK, Jang TS, Park JS, Kim KH, et al. Bull. Partition property of 5- nitrothiopyrimidine Nucleoside. Bull Korean Chem Soc 1979; 18(7): 734-6.
  • Jiménez BM, Kranz P, Lee CS, Gero AM, O'Sullivan phosphorylase pyrimidine analogs. Biochem Pharmacol 1989; 38(21): 3785-9.
  • Copik A, Suwinski J, Walczak K, Bronikowska J, Czuba Z, Kr َol W. Synthesis of 1-(2-hydroxy-3-methoxypropyl)uracils and their activity against L1210 and macrophage raw 264.7 cells. Nucleosides Nucleotides Nucleic Acids 2002; (21): 377-383.
  • Puccetti G, Perigaud A, Badan J, Ledoux I, Zyss J. 5-Nitrouracil: a transparent and efficient nonlinear organic crystal. J Opt Soc Am B 1993; 10 (4): 733- 744.
  • Smiley JA, Angelot JM, Cannon RC, Marshall EM, Asch DK. Radioactivity-based and spectrophotometric decarboxylase: identification of the thymidine salvage pathway in lower eukaryotes. Anal Biochem 1999; 266(1): 85-92.
  • Coats E, Glave WR, Hansch C. Structure- activity relations in thymidine phosphorylase inhibitors. A correlation using substituent constants and regression analysis. Med J Chem 1970; 13(5): 913–9.
  • Gills JJ, Lopoiccolo J, Denni PA. Nelfinavir, a new anti-cancer drug with pleiotropic effects and many paths to autophagy. Autophagy 2008; 4(1):107-9.
  • Hurley LH. DNA and its associated processes as targets for cancer therapy. Nat Rev Cancer 2002; 2(3): 188–200.
  • Shahabadi N, Moghadam NH. Determining the mode of interaction of calf thymus DNA with the drug sumatriptan using voltammetric and spectroscopic techniques. Spectrochimica Acta Part Spectroscopy 2012; 99:18–22.
  • Arkin MR, Stemp EDA, Turro C, Turro NJ, Barton JK. Luminescence Quenching in Supramolecular Systems: A Comparison of DNA- SDS Micelle-Mediated Photo-induced Electron Transfer between Metal Complexes. J Am Chem Soc 1996; 118: 2267-74.
  • Chlorobenzylidine-herring interaction: binding mode and thermodynamic sperm DNA Treated 2012; 88: 244-251.
  • Bian CL, Zeng QX, Yang LJ, Xiong HY, Zhang XH, Wang SF. Voltammetric studies of the interaction of rutin with DNA and its analytical applications on the MWNTs–COOH/Fe3O4 modified electrode. Sensors and Actuators B 2011; 156(2): 615– 620.
  • Wang Y, Ni Y, Kokot S. Voltammetric behavior of complexation of salbutamol with calf thymus DNA and its analytical application. Analytical Biochemistry 2011; 419(2): 76–80.
  • Carter MT, Rodriguez M, Bard AJ. Voltammetric studies of the interaction of metal chelates with DNA. 2. Tris-chelated complexes of cobalt(III) and iron(II) with 1,10-phenanthroline and 2,2'-bipyridine. J Am Chem Soc 1989; 111(24): 8901-11.
  • Ibrahim MS. Voltammetric studies of the interaction of nogalamycin antitumor drug with DNA. Anal Chim Acta 2001; 443:63–72.
  • Ibrahim MS, Kamal MM, Temerk YM. Comparison of the voltammetric studies at mercury and glassy carbon electrodes for the interaction of lumichrome with DNA and analytical applications. Anal Bioanal Chem 2003; 375:1024–30.
  • Temerk YM, Ibrahim MS, Kotb M. Voltammetric and spectroscopic studies on binding of antitumor Morin, Morin-Cu complex and Spectrochim Acta A 2009; 71 (5):1830–6.
  • Temerk YM, Ibrahim MS, Kotb M, Schuhmann W. Interaction of antitumor flavonoids with dsDNA in the absence and presence of Cu(II). Anal Bioanal Chem 2013; 405(11):3839-46.
  • Pang DW, Abruna HD. Micromethod for the investigation of the Interactions between DNA and Redox-Active Molecules. Anal Chem 1998; 70:3162-9.
  • Bard AJ, Faulkner LR. Electrochemical Methods Fundamentals and Applications. Wiley, New York 1980.
  • Frei YF, Miller IR. Influence of Adsorbed Positively Polarographic Currents of Cationic Depolarizers. II. J Phys Chem 1965; 69(9): 3018-23.
  • Wang ZY, Han R, in: Pharmaceutical Treatment of Tumor (in Chinese), People’s Health Press, Beijing, 1987; 72-4.
  • Zhu Z, Li NQ. Electrochemical studies of 9,10-anthraquinone interacting with hemoglobin and determination of hemoglobin. Mikrochim Acta 1999; 130(4): 301-8.
  • Feng Q, Li NQ, Jiang YY. Electrochemical studies of porphyrin interacting with DNA and determination of DNA. Anal Chim Acta 1997; 344:97-104.
  • Schäfer S, Sheldrick WS. Coligand tuning of the DNA binding properties of halfsandwich organometallic polypyridyl (pp) and monodentate ligands (L=Cl, (NH2)2CS, (NMe2)2CS) on the intercalation of (η5-pentamethylcyclopentadienyl)iridium dipyridoquinoxaline complexes. J Organ Chem 2007; 692: 1300-9.
  • Ortiz M, Fragoso A, Ortiz PJ, O’Sullivan CK. Elucidation of the mechanism of single stranded DNA interaction with methylene blue: A spectroscopic approach. J Photochem Photobio A: Chem 2011; 218: 26–32. Polyelectrolytes on influence of (III)- and –dipyridophenazine

Electrochemical Comparison of the Interaction of 5-Nitrouracil with Single-or Double-Stranded DNA at mercury and glassy carbon electrodes

Yıl 2014, Cilt: 2 Sayı: 1, 1 - 8, 01.04.2014
https://doi.org/10.5505/apjes.2014.46855

Öz

The interaction of the 5-Nitrouracil (5NU), with ss-, and ds-DNA was investigated electrochemically in
absence and presence of copper ions by using cyclic voltammetry (CV) and differential pulse stripping
voltammetry (DPSV) at hanging mercury drop electrode (HMDE) and glassy carbon electrode (GCE)
surfaces. It was found that, in absence of copper ions, the addition of ss- or ds-DNA to a buffered solution of
5NU results in a decrease on the 5NU redox peak current with a remarkable change in the peak potential (ca.
150 mV vs. Ag/AgCl) at both electrodes. This means that, an interaction of 5NU molecules with both ss- and
ds-DNA was observed. The results also demonstrate that a distinguish between ss-, and ds-DNA can be
achieved in presence of copper ion through their interaction with 5NU. The binding constants of 5NU with
ds-DNA at HMDE and GCE were determined through the changes on the 5NU redox peak currents (at
HMDE, 1.45x105 and at GCE, 2.65x105). The calibration plot for the DNA determination was obtained
through the corresponding decreases on the DPSV peak current of 5NU to different additions of DNA (ss- or
ds-DNA) concentration levels at the optimum conditions.

Kaynakça

  • Pharmacology, 6th ed. (Appleton & Lang, Norwalk,CT; 1995.
  • Lawrence TS, Davis MA, Maybaum J, Stetson PL, Ensminger WD. The Effect of Single versus Halogenated Radiosensitization and DNA Strand Breakage in Human Tumor Cells. Radiat Res 1990; 123: 192- Basic and Clinical Double-Strand Substitution Pyrimidine-Induced
  • Jain KS, Chitre TS, Miniyar PB, Kathiaravan MK, Bendre VS, Veer VS, et al. Biological and medicinal significance of pyrimidines. J Curr Sci 2006; 90(6):793-803.
  • Longley DB, Harkin DP, Johnston PG. 5- Fluorouracil: mechanisms of action and clinical strategies. Nat Rev Can 2003; 3:330-8.
  • Buchsbaum DJ, Khazaeli MB, Davis MA, Lawrence TS. Sensitization of radiolabeled monoclonal bromodeoxyuridine.Cancer 1994; 73: 999-1005.
  • Chelladurai M, Lobocki CA, Sultani M, Hanna Y, Drelichman A, Pieper DR, et al. Bromodeoxyuridine improves the cytotoxic effect of cisplatin: a comparison with 5-fluorouracil. Cancer Chemother Pharmacol 1997; 40(6):463-8.
  • Wardman P, Clarke ED, Flockhart IR, Wallace RG. The rationale for the development of improved hypoxic cell radiosensitizers. Brit J Cancer 1978 (Suppl. III) 1-5.
  • Lee BH, Shin JH, Lim MK, Jang TS, Park JS, Kim KH, et al. Bull. Partition property of 5- nitrothiopyrimidine Nucleoside. Bull Korean Chem Soc 1979; 18(7): 734-6.
  • Jiménez BM, Kranz P, Lee CS, Gero AM, O'Sullivan phosphorylase pyrimidine analogs. Biochem Pharmacol 1989; 38(21): 3785-9.
  • Copik A, Suwinski J, Walczak K, Bronikowska J, Czuba Z, Kr َol W. Synthesis of 1-(2-hydroxy-3-methoxypropyl)uracils and their activity against L1210 and macrophage raw 264.7 cells. Nucleosides Nucleotides Nucleic Acids 2002; (21): 377-383.
  • Puccetti G, Perigaud A, Badan J, Ledoux I, Zyss J. 5-Nitrouracil: a transparent and efficient nonlinear organic crystal. J Opt Soc Am B 1993; 10 (4): 733- 744.
  • Smiley JA, Angelot JM, Cannon RC, Marshall EM, Asch DK. Radioactivity-based and spectrophotometric decarboxylase: identification of the thymidine salvage pathway in lower eukaryotes. Anal Biochem 1999; 266(1): 85-92.
  • Coats E, Glave WR, Hansch C. Structure- activity relations in thymidine phosphorylase inhibitors. A correlation using substituent constants and regression analysis. Med J Chem 1970; 13(5): 913–9.
  • Gills JJ, Lopoiccolo J, Denni PA. Nelfinavir, a new anti-cancer drug with pleiotropic effects and many paths to autophagy. Autophagy 2008; 4(1):107-9.
  • Hurley LH. DNA and its associated processes as targets for cancer therapy. Nat Rev Cancer 2002; 2(3): 188–200.
  • Shahabadi N, Moghadam NH. Determining the mode of interaction of calf thymus DNA with the drug sumatriptan using voltammetric and spectroscopic techniques. Spectrochimica Acta Part Spectroscopy 2012; 99:18–22.
  • Arkin MR, Stemp EDA, Turro C, Turro NJ, Barton JK. Luminescence Quenching in Supramolecular Systems: A Comparison of DNA- SDS Micelle-Mediated Photo-induced Electron Transfer between Metal Complexes. J Am Chem Soc 1996; 118: 2267-74.
  • Chlorobenzylidine-herring interaction: binding mode and thermodynamic sperm DNA Treated 2012; 88: 244-251.
  • Bian CL, Zeng QX, Yang LJ, Xiong HY, Zhang XH, Wang SF. Voltammetric studies of the interaction of rutin with DNA and its analytical applications on the MWNTs–COOH/Fe3O4 modified electrode. Sensors and Actuators B 2011; 156(2): 615– 620.
  • Wang Y, Ni Y, Kokot S. Voltammetric behavior of complexation of salbutamol with calf thymus DNA and its analytical application. Analytical Biochemistry 2011; 419(2): 76–80.
  • Carter MT, Rodriguez M, Bard AJ. Voltammetric studies of the interaction of metal chelates with DNA. 2. Tris-chelated complexes of cobalt(III) and iron(II) with 1,10-phenanthroline and 2,2'-bipyridine. J Am Chem Soc 1989; 111(24): 8901-11.
  • Ibrahim MS. Voltammetric studies of the interaction of nogalamycin antitumor drug with DNA. Anal Chim Acta 2001; 443:63–72.
  • Ibrahim MS, Kamal MM, Temerk YM. Comparison of the voltammetric studies at mercury and glassy carbon electrodes for the interaction of lumichrome with DNA and analytical applications. Anal Bioanal Chem 2003; 375:1024–30.
  • Temerk YM, Ibrahim MS, Kotb M. Voltammetric and spectroscopic studies on binding of antitumor Morin, Morin-Cu complex and Spectrochim Acta A 2009; 71 (5):1830–6.
  • Temerk YM, Ibrahim MS, Kotb M, Schuhmann W. Interaction of antitumor flavonoids with dsDNA in the absence and presence of Cu(II). Anal Bioanal Chem 2013; 405(11):3839-46.
  • Pang DW, Abruna HD. Micromethod for the investigation of the Interactions between DNA and Redox-Active Molecules. Anal Chem 1998; 70:3162-9.
  • Bard AJ, Faulkner LR. Electrochemical Methods Fundamentals and Applications. Wiley, New York 1980.
  • Frei YF, Miller IR. Influence of Adsorbed Positively Polarographic Currents of Cationic Depolarizers. II. J Phys Chem 1965; 69(9): 3018-23.
  • Wang ZY, Han R, in: Pharmaceutical Treatment of Tumor (in Chinese), People’s Health Press, Beijing, 1987; 72-4.
  • Zhu Z, Li NQ. Electrochemical studies of 9,10-anthraquinone interacting with hemoglobin and determination of hemoglobin. Mikrochim Acta 1999; 130(4): 301-8.
  • Feng Q, Li NQ, Jiang YY. Electrochemical studies of porphyrin interacting with DNA and determination of DNA. Anal Chim Acta 1997; 344:97-104.
  • Schäfer S, Sheldrick WS. Coligand tuning of the DNA binding properties of halfsandwich organometallic polypyridyl (pp) and monodentate ligands (L=Cl, (NH2)2CS, (NMe2)2CS) on the intercalation of (η5-pentamethylcyclopentadienyl)iridium dipyridoquinoxaline complexes. J Organ Chem 2007; 692: 1300-9.
  • Ortiz M, Fragoso A, Ortiz PJ, O’Sullivan CK. Elucidation of the mechanism of single stranded DNA interaction with methylene blue: A spectroscopic approach. J Photochem Photobio A: Chem 2011; 218: 26–32. Polyelectrolytes on influence of (III)- and –dipyridophenazine
Toplam 33 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Mühendislik
Bölüm Makaleler
Yazarlar

Mohamed Sayed Ibrahim Bu kişi benim

Hossieny Sameh Mohamed Ibrahim Bu kişi benim

Moustafa Mohamed Kamal Bu kişi benim

Yassin Mohamed Temerk Bu kişi benim

Yayımlanma Tarihi 1 Nisan 2014
Gönderilme Tarihi 14 Kasım 2015
Yayımlandığı Sayı Yıl 2014 Cilt: 2 Sayı: 1

Kaynak Göster

IEEE M. S. Ibrahim, H. S. M. Ibrahim, M. M. Kamal, ve Y. M. Temerk, “Electrochemical Comparison of the Interaction of 5-Nitrouracil with Single- or Double-Stranded DNA at mercury and glassy carbon electrodes”, APJES, c. 2, sy. 1, ss. 1–8, 2014, doi: 10.5505/apjes.2014.46855.