In vitro antioxidant activity of selected 4-hydroxy-chromene-2-one derivatives-SAR, QSAR and DFT studies

International Journal of Molecular Sciences

Volumn 12, Issue 5, 2011, Pages 2822-2841

  Mladenović, Milan ^a   Mihailović, Mirjana ^b   Bogojević, Desanka ^b   Matić, Sanja ^a   Nićiforović, Neda ^a   Mihailović, Vladimir ^a   Vuković, Nenad ^a   Sukdolak, Slobodan ^a   Solujić, Slavica ^a  

^a UNIVERSITY OF KRAGUJEVAC   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

4 hydroxycoumarins; Antioxidant activity in vitro; BDEs; Design; DFT; QSAR

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 4 HYDROXY CHROMENE 2 ONE DERIVATIVE; 4 HYDROXYCOUMARIN DERIVATIVE; FERROUS ION; LINOLEIC ACID; UNCLASSIFIED DRUG; 2,2-DIPHENYL-1-PICRYLHYDRAZYL; ANTIOXIDANT; BIPHENYL DERIVATIVE; FREE RADICAL; LIPID PEROXIDE; PICRIC ACID; SCAVENGER;

ACIDITY; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; LIPID PEROXIDATION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STRUCTURE ACTIVITY RELATION; CHEMICAL STRUCTURE; CHEMISTRY;

4-HYDROXYCOUMARINS; ANTIOXIDANTS; BIPHENYL COMPOUNDS; FREE RADICAL SCAVENGERS; FREE RADICALS; LIPID PEROXIDES; MODELS, MOLECULAR; PICRATES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79957795403     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms12052822     Document Type: Article

References (36)

1. Traykova, M.; Kostova, I. Coumarin derivatives and antioxidative stress. Int. J. Pharmacol. 2005, 1, 29-32.
2. Droge, W. Free radicals in the physiological control of the cell function. Physiol. Rev. 2002, 82, 47-95.
3. Halliwell, B. How to characterize a biological antioxidant. Free Rad. Res. 1990, 9, 1-32.
4. Juliano, L.; Colavita, A.R.; Leo, R.; Pratico, D.; Violi, F. Oxygen free radicals and platelet activation. Free Rad. Biol. Med. 1997, 22, 999-1006.
5. Lassegue, B.; Griendling, K.K. Reactive oxygen species in hypertension. Am. J. Hyper. 2004, 17, 852-860.
6. McIntosh, L.J.; Trush, M.A.; Tronsoco, J.C. Increased susceptibility of Alzheimer's disease temporal cortex to oxygen-free radical-mediated processes. Free Rad. Biol. Med. 1997, 23, 183-190.
7. Festa, G.; Aglitti, T.; Duranti, G.; Ricordi, R.; Perticone, P.; Cozzi, R. Strong antioxidant activity of ellagic acid in mammalian cells in vitro revealed by comet assay. Anticancer Res. 2001, 21, 3903-3908.
8. Hoult, J.; Paya, M. Pharmacological and biochemical actions of simple coumarins: Natural products with therapeutic potential. Gen. Pharmacol. 1996, 27, 713-722.
9. Nićiforović, N.; Mihailović, V.; Mašković, P.; Solujić, S.; Stojković, A.; Pavlović Muratspahić, D. Antioxidant activity of selected plant species; potential new sources. Food Chem. Toxicol. 2010, 48, 3125-3130.
10. Sinhg, R.; Singh, B.; Singh, S.; Kumar, N.; Kumar, N.; Arora, S. Umbeliferone-An antioxidant isolated from Acacia nilotica (L.) Willd. Ex. Del. Food Chem. 2010, 120, 825-830.
11. Wu, C.; Huang, M.; Lin, Y.; Ju, H.; Ching, H. Antioxidant properties of Cortex Fraxini and its simple coumarins. Food Chem. 2007, 104, 1464-1471.
12. Ismail, M.; Ibrar, M.; Iqbal, Z.; Hussain, J.; Hussain, H.; Ahmed, M.; Ejaz, A.; Choudhary, M.I. Chemical constituents and antioxidant activity of Geranium wallichianum. Rec. Nat. Prod. 2009, 3, 193-197.
13. Thuong, P.T.; Hung, M.T.; Ngoc, T.M.; Ha do, T.; Min, S.B.; Kwack, J.S.; Kang, S.T.; Choi, S.J.; Bae, H.K. Antioxidant activities of coumarins from Korean medicinal plants and their structure-activity relationships. Phytother. Res. 2010, 24, 101-106.
14. Ćavar, S.; Kovač, F.; Maksimović, M. Synthesis and antioxidant activity of selected 4-methylcoumarins. Food Chem. 2009, 117, 135-142.
15. Kontogiorgis, A.C.; Hadjipavlou-Litina, J.D. Synthesis and biological evaluation of novel coumarin derivatives with a 7-azomethine linkage. Bioorg. Med. Chem. Lett. 2004, 14, 611-614.
16. Mladenović, M.; Vuković, N.; Nićiforović, N.; Sukdolak, S.; Solujić, S. Synthesis and molecular descriptor characterization of novel 4-hydroxy-chromene-2-one derivatives as antimicrobial agents. Molecules 2009, 14, 1495-1512.
17. Vuković, N.; Sukdolak, S.; Solujić, S.; Milošević, T. Synthesis and antimicrobial evaluation of some novel 2-aminothiazole derivatives of 4-hydroxy-chromene-2-one. Arch. der Pharm. 2008, 341, 491-496.
18. Pope, M.; Swenberg, E.C. Electronic Processes in Organic Crystals and Polymers, 2nd ed.; Oxford Science Publications, Oxford University Press: New York, NY, USA, 1999; pp. 143-197.
19. Vuković, N.; Sukdolak, S.; Solujić, S.; Nićiforović, N. Substituted imino and amino derivatives of 4-hydroxycoumarins as novel antioxidant, antibacterial and antifungal agents: Synthesis and in vitro assessments. Food Chem. 2010, 120, 1011-1018.
20. Marković, S.Z.; Manojlović, T.N. DFT study on the reactivity of OH groups in emodin: Structural and electronic features of emodin radicals. Monats. Chem. 2009, 140, 1311-1318.
21. Zhang, Y.H; Wang, F.L. Theoretical elucidation of structure-activity relationship for coumarins to scavenge peroxyl radical. J. Mol. Struc. (TEOCHEM) 2004, 673, 199-202.
22. Duh, P.D.; Tu, Y.Y.; Yen, G.C. Antioxidant activity of aqueous extract of Harnjyur (Chrysanthemum morifolium Ramat). Lebensmwiss Technol. 1999, 32, 269-277.
23. Selassie, C.D. History of quantitative structure-activity relationships. In Burger's Medicinal Chemistry & Drug Discovery, 6th ed.; Abraham, D.J., Ed.; John Wiley and Sons, Inc.: New York, NY, USA, 2003; Volume 1, pp. 1-48.
24. Liu, J.K.; Hu, L.; Dong, Z.J.; Hu, Q. DPPH radical scavenging activity of ten natural p-terphenyl derivatives obtained from three edible mushrooms indigenous to China. Chem. Biodiver. 2004, 1, 601-605.
25. Marx, J.L. Oxygen free radicals linked to many diseases. Science 1985, 235, 529-531.
26. Spessard, O.G. ACD Labs/LogP dB 3.5 and ChemSketch 3.5. J. Chem. Inform. Comp. Sci. 1998, 38, 1250-1253.
27. Prieto, P.; Pineda, M.; Aguilar, M. Spectrophotometric quantification of antioxidant capacity trough the formation of a phosphomolybdenium complex: Specific application to the determination of vitamin E. Anal. Biochem. 1999, 269, 337-341.
28. Origin Pro 8. OriginLab Corporation, One Roundhouse Plaza: Northampton, MA, USA, 2009.
29. Takao, T.; Watanabe, N.; Yagi, I.; Sakata, K. A simple screening method for antioxidants and isolation of several antioxidants produced by marine bacteria from fish and shellfish. Biosci. Biotech. Biochem. 1994, 58, 1780-1783.
30. Masude, T.; Isibe, D.; Jitoe, A.; Naramati, N. Antioxidant curcuminoids from rhizomes of Curcuma zanthorrhiza. Phytochemistry 1992, 33, 3645-3647.
31. Halliwell, B.; Gutteridge, J.M.C.; Aruoma, O. The deoxyribose method: A simple "test-tube" assay for determination of rate constants for reactions of hydroxyl radicals. Anal. Biochem. 1987, 165, 215-219.
32. Carter, P. Spectrophotometric determination of serum iron at the submicrogram level with a new reagent (ferrozine). Anal. Biochem. 1971, 40, 450-458.
33. Software Spartan for Windows. Wavefunction, Inc.: Irvine, CA, USA, 2006.
34. Pedretti, A.; Villa, A.; Vistoli, G. VEGA: A versatile program to convert, handle and visualize molecular structure on Windows-based PCs. J. Mol. Graph. Model. 2002, 21, 47-49.
35. MOPAC 2009. Stewart Computational Chemistry: Colorado Springs, CO, USA, 2009. Available online: http://www.openMOPAC.net (accessed on 13 April 2011).
36. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Montgomery, J.A., Jr.; Vreven, T.; Kudin, K.N.; Burant, J.C.; Millam, J.M.; Iyengar, S.S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G.A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J.E.; Hratchian, H.P.; Cross, J.B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.W.; Ayala, P.Y.; Morokuma, K.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Zakrzewski, V.G.; Dapprich, S.; Daniels, A.D.; Strain, M.C.; Farkas, O.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Ortiz, J.V.; Cui, Q.; Baboul, A.G.; Clifford, S.; Cioslowski, J.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.M.W.; Johnson, B.; Chen, W.; Wong, M.W.; Gonzalez, C.; Pople, J.A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, USA, 2003.