Antioxidant activity of a series of fluorinated pyrano-nucleoside analogues of N 4-benzoyl cytosine and N 6-benzoyl adenine

International Journal of Molecular Sciences

Volumn 8, Issue 7, 2007, Pages 695-704

  Spanou, Chrysoula ^a   Manta, Stella ^a   Komiotis, Dimitri ^a   Dervishi, Albiona ^a   Kouretas, Demetrios ^a  

^a UNIVERSITY OF THESSALY   (Greece)

Author keywords

Antioxidants; DNA damage; DPPH; Fluorinated nucleosides; ROS

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; DNA; HYDROXYL RADICAL; NUCLEOSIDE ANALOG; PEROXY RADICAL; REACTIVE OXYGEN METABOLITE;

ANTIOXIDANT ACTIVITY; ARTICLE; DNA DETERMINATION; DNA STRAND; DNA STRAND BREAKAGE; IN VITRO STUDY;

EID: 34547620662     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/i8070695     Document Type: Article

References (35)

1. Zhou, W.; Gumina, G.; Chong, Y.; Wang, J.; Shinazi, R.F.; Chu, C.K. Synthesis, Structure-Activity Relationships, and Drug Resistance of β-D-3′-Fluoro-2′,3′-Unsaturated Nucleosides as Anti-HIV Agents. J. Med. Chem. 2004, 47, 3399-3408.
2. Perigaud, C.; Gosselin, G.; Imbach, J.L. Nucleosides Analogues as Chemotherapeutic Agents: A Review. Nucleosides Nucleotides 1992, 11, 903-945.
3. Robins, R.K.; Kini, G.D. Purines and Purine Nucleoside Analogues as Antitumor Agents. In The Chemistry of Antitumor Agents; Wilman, D.E.V. Ed.; Chapman and Hall: New York, 1990; pp 299-321.
4. MacCoss, M.; Robins, M.J. Anticancer Pyrimidines, Pyrimidine Nucleosides and Prodrugs. In the chemistry of Antitumor Agents; Wilman, D.E.V. Ed.; Chapman and Hall: New York, 1990; pp 261-298.
5. Verheggen, I.; Van Aerschot, A.; Toppet, S.; Snoeck, R.; Janssen, G.; Balzarini, J.; De Clercq, E.; Herdewijn, P. Synthesis and Antiherpes Virus Activity of 1,5-Anhydrohexitol Nucleosides. J. Med. Chem. 1993, 36, 2033-2040.
6. Verheggen, I.; Van Aerschot, A.; Van Meervelt, L.; Rozenski, J.; Wiebe, L.; Snoeck, R.; Andrei, G.; Balzarini, J.; Claes, P.; De Clercq, E.; Herdewijn, P. Synthesis, Biological Evaluation and Structure Analysis of New 1,5-Anhydrohexitol Nucleosides. J. Med. Chem. 1995, 38, 826-835.
7. Ostrowski, T.; Wroblowski, B.; Busson, R.; Rozenski, J.; De Clercq, E.; Bennet, M.S.; Champness, J.N.; Summers, W.C.; Sanderson, M.R.; Herdewijn, P. 5-Substituted Pyrimidines with a 1,5-Anhydro-2,3-Dideoxy-D-Arabino- Hexitol Moiety at N-1: Synthesis, Antiviral Activity, Conformational Analysis, and Interaction with Viral Thymidine Kinase. J. Med. Chem. 1998, 41, 4343-4353.
8. Maurinsh, Y.; Schraml, J.; De Winter, H.; Blaton, N.; Peeters, O.; Lescrinier, E.; Rozenski, J.; Van Aerschot, A.; De Clercq, E.; Busson, R.; Herdewijn, P. Synthesis and Conformational Study of 3-Hydroxy-4-(Hydroxymethyl)- 1-Cyclohexanyl Purines and Pyrimidines. J. Org. Chem. 1997, 62, 2861-2871.
9. Haouz, A.; Vanheusden, V.; Munier-Lechman, H.; Froeyen, M.; Herdewijn, P.; Van Galenbergh, S.; Delarue, M. Enzymatic and Structural Analysis of Inhibitors Designed Against Mycobacterium Tuberculosis Thymidylate Kinase. New Insights into the Phosphoryl Transfer Mechanism. J. Biol. Chem. 2003, 278, 4963-4971.
10. Vastmans, K.; Pochet, S.; Peys, A.; Kerremans, L.; Van Aerschot, A.; Hendrix, C.; Marliere, P.; Herdewijn, P. Enzymatic Incorporation in DNA of 1,5-Anhydrohexitol Nucleotides. Biochemistry 2000, 39, 12757-12765.
11. Vastmans, K.; Froeyen, M.; Kerremans, L.; Pochet, S.; Herdewijn, P. Reverse Transcriptase Incorporation of 1,5-Anhydrohexitol Nucleotides. Nucleic Acids Res. 2001, 29, 3154-3163.
12. Paterson, J.; Uriel, C.; Egron, M.J.; Herscovici, J.; Antonakis, K.; Alaoui, M. Antiproliferative and Apoptotic Activities of Ketonucleosides and Keto-C-Glycosides against Non-Small-Cell Lung Cancer Cells with Intrinsic Drug Resistance. Antimicrob. Agents Chemother. 1998, 42, 779-784.
13. Alaoui, M.; Lasne, C.; Antonakis, K.; Chouroulinkov, I. Absence of Genotoxic Effects in Cells Exposed to Four Ketonucleoside Derivatives. Mutagenesis 1986, 1, 411-417.
14. Alaoui, M.; Egron, M.J.; Bessodes, M.; Antonakis, K.; Chouroulinkov, I. Relationship Between The Structure and Cytotoxic Activity of New Unsaturated Ketonucleosides Tested on Eight Cell Lines. Eur. J. Med. Chem. 1987, 22, 305-310.
15. Egron, M.J.; Komiotis, D.; Dorange, I.; Herscovici, J.; Antonakis, K. New Short Route to Unsaturated Fluoroketonucleosides: Case of 5-Fluoro-1-(6- O-Acetyl-3,4-Di-deoxy-3-Fluoro-β-D-Glycero-Hex-3-Eno- Pyranos-2-Ulosyl) Uracil. Nucleosides, Nucleotides, and Nucleic Acids 2005, 24, 243-246.
16. Halmos, T.; Komiotis, D.; Antonakis, K. Cancer Oriented Ketonucleosides: Synthesis of 7-[6-O-(5-Carboxypentyl)-3.4-Dideoxy-and 3,4-Dideoxy-6-O-(6-Hydroxyexyl)-β-D-Glycero-Hex-3- Enopyranosyl-2-ulose]Theophyllines and Their Coupling with Cancer-Specific Proteins. Carbohydr. Res. 1986, 156, 256-263.
17. Antonakis, K.; Chouroulinkov, I. Studies on the Inhibition of the Growth of KB Cells by 9- and 7-(Ketonucleosides). Biochem. Pharmacol. 1974, 23, 2095-2100.
18. Halmos, T.; Cardon, A.; Antonakis, K. Interactions of Cytostatic Unsaturated Ketonucleosides with Sulfhydryl Containing Cell Constituents. Chem. Biol. Interact. 1983, 46, 11-29.
19. Antonakis, K.; Halmos, T.; Bach, J.; Chouroulinkov, I. Antitumor Activity of Ketonucleosides. Unsaturated Ketohexosyl Purines. Eur. J. Med. Chem. 1980, 15, 237-240.
20. Chouroulinkov, I.; Antonakis, K. Antitumor Effects of Keto-Nucleosides. Study of the Antitumor Activity of Y(3′-O-Acetyl-4′,6′- Dideoxy-Beta-L-Glycero-Hex-3′-Eno-pyranosyl)Theophylline and 1(4′-Keto-2′,3′-O-Isopropylidene-Alpha-L- "Rhammosyl" O Thymine Against L1210 Leukemia in Mice. C R Acad. Sci. Hebd Seances Acad. Sci. D 1977, 285, 1021-1024.
21. Antonakis, K. Synthesis of Nucleoside Analogues. Chimia 1975, 29, 59.
22. Antonakis, K.; Egron, M.J. Unsaturated Ketonucleosides. The Synthesis and Properties of 7-(3-O-Acetyl-4,6-Dideoxy-β-L-Glycero-Hex-3 Enopyranosylulose)Theophylline. Carbohydr. Res. 1973, 27, 468-470.
23. Egron, M.J.; Leclercq, F.; Antonakis, K.; Bennani-Baiti, I.; Frayssinet, C. Synthesis and Antineoplastic Properties of 3′-Deoxy-3′- Fluoroketonucleoside Derivatives. Correlations Between Structure and Biological Activity. Carbohydr. Res. 1993, 248, 143-150.
24. Van Aerschot, A.; Herdewijn, P.; Balzarini, J.; Pawels, R.; De Clerq, E. 3′-Fluoro-2′,3′-Dideoxy-5-Chlorouridine: Most Selective Anti-HIV-1 Agent Among a Series of New 2′- and 3′-Fluorinated 2′,3′-Dideoxynucleoside Analogues. J. Med. Chem. 1989, 32, 1743-1749.
25. Blandin, M.; Son, T.D.; Catlin, J.C.; Guschlbauer, W. Nucleoside conformations. 16. Nuclear Magnetic Resonance and Circular Dichroism Studies on Pyrimidine-2′-Fluoro-2′-Deoxyribonucleosides. Biochim. Biophys. Acta 1974, 361, 249-253.
26. Morton, G.O.; Lancaster, J.E.; Van Lear, G.E.; Fulmor, W.; Meyer, W.E. The Structure of Nucleocidin. 3. (A New Structure). J. Amer. Chem. Soc. 1969, 91, 1535-1537.
27. Lipnick, R.L.; Fissekis, J.D. A Comparative Conformational Study of Certain 2′-Deoxy-2′-Fluoro-Arabinofuranosylcytosine Nucleosides. Biochim. Biophys. Acta 1980, 608, 96-102.
28. 4-Benzoyl Cytosine. Bioorg. Med. Chem. 2007, 15, 980-987.
29. 6-Benzoyl Adenine. Eur. J. Med. Chem. (in press).
30. Prior, R.L.; Wu, X.; Schaich, K. Standardized Methods for the Determination of Antioxidant Capacity and Phenolics in Foods and Dietary Supplements. J. Agric. Food Chem. 2005, 53, 4290-4302.
31. Mylonas, C.; Kouretas, D. Lipid Peroxidation and Tissue Damage. In Vivo 1999, 13, 295-310.
32. Brand-Williams, W.; Cuvelier, M.E.; Berset, C. Use of a Free Radical Method to Evaluate Antioxidant Activity. Lebensm. Wiss. Technol. 1995, 28, 25-30.
33. Chang, S.T.; Wu, J.H.; Wang, S.Y.; Kang, P.L.; Yang, N.S.; Shyur, L.F. Antioxidant Activity of Extracts from Acacia confusa Bark and Heartwood. J. Agric. Food Chem. 2001, 49, 3420-3424.
34. Spanou, C.; Stagos, D.; Tousias, L.; Angelis, A.; Aligiannis, N.; Skaltsounis, A.L.; Kouretas, D. Assessment of Antioxidant Activity of Extracts from Unique Greek Varieties of Leguminosae Family Plants Using in vitro Assays. Anticancer Research (submitted).
35. Keum, Y.S.; Park, K.K.; Lee, J.M.; Chun, K.S.; Park, J.H.; Lee, S.K.; Kwon, H.; Surch, Y. Antioxidant and Anti-tumor Promoting Activities of the Methanol Extract of the Heat-Processed Ginseng. Cancer Lett. 2000, 150, 41-48.