Synthesis and electrochemical and biological studies of novel coumarin-chalcone hybrid compounds

Journal of Medicinal Chemistry

Volumn 56, Issue 15, 2013, Pages 6136-6145

  Pérez Cruz, Fernanda ^a   Vazquez Rodriguez, Saleta ^b   Matos, Maria João ^b   Herrera Morales, Alejandra ^a   Villamena, Frederick A ^c   Das, Amlan ^c   Gopalakrishnan, Bhavani ^c   Olea Azar, Claudio ^a   Santana, Lourdes ^b   Uriarte, Eugenio ^b  

^a UNIVERSITY OF CHILE   (Chile)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^c THE OHIO STATE UNIVERSITY COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANT; CATECHIN; CHALCONE; COUMARIN; HYDROXYL RADICAL; PROTECTIVE AGENT; QUERCETIN;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; BIOASSAY; CELL PROTECTION; CONCENTRATION RESPONSE; CYCLIC POTENTIOMETRY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; ENDOTHELIUM CELL; HYBRID; NONHUMAN; OXIDATION; OXIDATION REDUCTION POTENTIAL; SCAVENGING SYSTEM;

ANIMALS; ANTIOXIDANTS; CATTLE; CELL SURVIVAL; CELLS, CULTURED; CHALCONES; COUMARINS; CYTOPROTECTION; CYTOTOXINS; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE SPECTROSCOPY; ENDOTHELIAL CELLS; FREE RADICAL SCAVENGERS; OXIDATION-REDUCTION; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84881404683     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400546y     Document Type: Article

References (65)

1. Forman, H.; Maiorino, M.; Ursini, F. Signaling functions of reactive oxygen species Biochemistry. 2010, 49, 835-842
2. Lü, J. M.; Lin, P. H.; Yao, Q.; Chen, C. Chemical and molecular mechanisms of antioxidants: experimental approaches and model systems J. Cell. Mol. Med. 2010, 14, 840-860
3. Halliwell, B. Antioxidants and human diseases: a general introduction Nutr. Rev. 1997, 55, 44-52
4. Korkina, L. G.; Afans'Ev, I. B. Antioxidant and chelating properties of flavonoids Adv. Pharmacol. 1996, 38, 151-163
5. Yin, H.; Xu, L.; Porter, N. A. Free radical lipid peroxidation: mechanisms and analysis Chem. Rev. 2011, 111, 5944-5972
6. Sies, H. Oxidative stress: oxidants and antioxidants Exp. Physiol. 1997, 82, 291-295
7. Traykova, M.; Kostova, I. Coumarin derivatives and oxidative stress Int. J. Pharm. 2005, 1, 29-32
8. Obrenovich, M. E.; Li, Y.; Parvathaneni, K.; Yendluri, B. B.; Palacios, H. H.; Leszek, J.; Aliev, G. Antioxidants in health, disease and aging CNS Neurol. Disord.: Drug Targets 2011, 10, 192-207
9. Zou, X. Q.; Peng, S. M.; Hu, C. P.; Tan, L. F.; Deng, H. W.; Li, Y, J. Furoxan nitric oxide donor coupled chrysin derivatives: synthesis and vasculoprotection Bioorg. Med. Chem. Lett. 2011, 21, 1222-1226
10. Liu, R. H.; Hotchkiss, J. H. Potential genotoxicity of chronically elevated nitric oxide: a review Mutat. Res. 1995, 339, 73-89
11. Geier, D. A.; Kern, J. K.; Garver, C. R.; Adams J. B. Audhya, T.; Nataf, R.; Geier, M. R. Biomarkers of environmental toxicity and susceptibility in autism J. Neurol. Sci. 2009, 280, 101-108
12. Pasupathi, P.; Chandrasekar, V.; Kumar, U. S. Evaluation of oxidative stress, enzymatic and non-enzymatic antioxidants and metabolic thyroid hormone status in patients with diabetes mellitus Diabetes Metab. Syndr.: Clin. Res. Rev. 2009, 3, 160-165
13. Reuter, S.; Gupta, S. C.; Chaturvedi, M. M.; Aggarwal, B. B. Oxidative stress, inflammation, and cancer: how are they linked? Free Radical Biol. Med. 2010, 49, 1603-1616
14. Lodovici, M.; Menichetti, S.; Viglianisi, C.; Giuliani, E. Polyhydroxylated 4-thiaflavans as multipotent antioxidants: Protective effect on oxidative DNA damage in vitro Bioorg. Med. Chem. Lett. 2006, 16, 1957-1960
15. Heim, K. E.; Tagliaferro, A. R.; Bobilya, D. J. Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships J. Nutr. Biochem. 2002, 13, 572-584
16. Khlebnikov, A. I.; Schepetkin, I. A.; Domina, N. G.; Kirpotina, L. N.; Quinn, M. T. Improved quantitative structure-activity relationship models to predict antioxidant activity of flavonoids in chemical, enzymatic, and cellular systems Bioorg. Med. Chem. 2007, 15, 1749-1770
17. Kostova, I.; Bhatia, S.; Grigorov, P.; Balkansky, S.; Parmar, V. S.; Prasad, A. K.; Saso, L. Coumarin as antioxidants Curr. Med. Chem. 2011, 18, 3929-3951
18. Torres de Pinedo, A.; Peñalver, P.; Morales, J. C. Synthesis and evaluation of new phenolic-based antioxidants: structure-activity relationship Food Chem. 2007, 103, 55-61
19. Haenen, G. R. M. M.; Arts, M. J. T. J.; Bast, A.; Coleman, M. D. Structure and activity in assessing antioxidant activity in vitro and in vivo: A critical appraisal illustrated with the flavonoids Environ. Toxicol. Pharmacol. 2006, 21, 191-198
20. Perez-Cruz, F.; Serra, S.; Delogu, G.; Lapier, M.; Maya, J. D.; Olea-Azar, C.; Santana, L.; Uriarte, E. Antitrypanosomal and antioxidant properties of 4-hydroxycoumarins derivatives Bioorg. Med. Chem. Lett. 2012, 22, 5569-5573
21. Matos, M. J.; Perez-Cruz, F.; Vazquez-Rodriguez, S.; Uriarte, E.; Santana, L.; Borges, F.; Olea-Azar, C. Remarkable antioxidant properties of a series of hydroxy-3-arylcoumarins Bioorg. Med. Chem. 2013, 21, 3900-3906
22. Kondo, K.; Hirano, R.; Matsumoto, A.; Igarashi, O.; Itakura, H. Inhibition of LDL oxidation by cocoa Lancet. 1996, 348, 1514-1518
23. Mazur, A.; Bayle, D.; Lab, C.; Rock, E.; Rayssiguier, Y. Inhibitory effect of procyanidin-rich extracts on LDL oxidation in vitro Atherosclerosis 1999, 145, 421-422
24. Ferrali, M.; Signorini, C.; Caciotti, B.; Sugherini, L.; Ciccoli, L.; Giachetti, D.; Comporti, M. Protection against oxidative damage of erythrocyte membranes by the flavonoid quercetin and its relation to iron chelating activity FEBS Lett. 1997, 416, 123-129
25. Elliott, A. J.; Scheiber, S. A.; Thomas, C.; Pardini, R. S. Inhibition of glutathione reductase by flavonoids Biochem. Pharmacol. 1992, 44, 1603-1608
26. Hirano, R.; Sasamoto, W.; Matsumoto, A.; Itakura, H.; Igarashi, O.; Kondo, K. Antioxidant ability of various flavonoids against DPPH radicals and LDL oxidation J. Nutr. Sci. Vitaminol. 2001, 47, 357-362
27. Cos, P.; Ying, L.; Calomme, M.; Hu, J. P.; Cimanga, K.; Van Poel, B.; Pieters, L.; Vlietnck, A. J.; Vanden Berghe, D. Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers J. Nat. Prod. 1998, 61, 71-76
28. Sahu, N. K.; Balbhadra, S. S.; Choudhary, J.; Kohli, D. V. Exploring pharmacological significance of chalcone scaffold: a review Curr. Med. Chem. 2012, 19, 209-225
29. Go, M. L.; Wu, X.; Liu, X. L. Chalcones: an update on cytotoxic and chemoprotective properties Curr. Med. Chem. 2005, 12, 483-499
30. Bandgar, B. P.; Gawande, S. S.; Bodade, R. G.; Gawande, N. M.; Khobragade, C. N. Synthesis and biological evaluation of a novel series of pyrazole chalcones as anti-inflammatory, antioxidant and antimicrobial agents Bioorg. Med. Chem. 2009, 17, 8168-8173
31. Gaikwad, P.; Priyadarsini, K. I.; Naumov, S.; Rao, B. S. M. Radiation and quantum chemical studies of chalcone derivatives J. Phys. Chem. A. 2010, 114, 7877-7885
32. Detsi, A.; Majdalani, M.; Kontogiorgis, C. A.; Hadjipavlou-Litina, D.; Kefalas, P. Natural and synthetic 2'-hydroxy-chalcones and aurones: synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity Bioorg. Med. Chem. 2009, 17, 8073-8085
33. Kumar, V.; Kumar, S.; Hassan, M.; Wu, H.; Thimmulappa, R. K.; Kumar, A.; Sharma, S. K.; Parmar, V. S.; Biswal, S.; Malhotra, S. V. Novel chalcone derivatives as potent Nrf2 activators in mice and human lung epithelial cells J. Med. Chem. 2011, 54, 4147-4159
34. Valdameri, G.; Gauthier, C.; Terreux, R.; Kachadourian, R.; Day, B. J.; Winnischofer, S. M. B.; Rocha, M. E. M.; Frachet, V.; Ronot, X.; Di Pietro, A.; Boumendjel, A. Investigation of chalcones as selective inhibitors of the breast cancer resistance protein: critical role of methoxylation in both inhibition potency and cytotoxicity J. Med. Chem. 2012, 55, 3193-3200
35. Kachadourian, R.; Day, B. J.; Pugazhenti, S.; Franklin, C. C.; Genoux-Bastide, E.; Mahaffey, G.; Gauthier, C.; Di Pietro, A.; Boumendjel, A. A synthetic chalcone as a potent inducer of glutathione biosynthesis J. Med. Chem. 2012, 55, 1382-1388
36. Jung, J. C.; Jang, S.; Lee, Y.; Min, D.; Lim, E.; Jung, H.; Oh, M.; Oh, S.; Jung, M. Efficient synthesis and neuroprotective effect of substituted 1,3-diphenyl-2-propen-1-ones J. Med. Chem. 2008, 51, 4054-4058
37. Borges, F.; Roleira, F.; Milhazes, N.; Santana, L.; Uriarte, E. Simple coumarins and analogues in medicinal chemistry: occurrence, synthesis and biological activity Curr. Med. Chem. 2005, 12, 887-916
38. Rao, H. S. P.; Tangeti, V. S. Synthesis of 3-aroylcoumarin-flavone hybrids Lett. Org. Chem. 2012, 9, 218-220
39. Rao, H. S. P.; Sivakumar, S. Condensation of α-aroylketene dithioacetals and 2-hydroxyarylaldehydes results in facile synthesis of a combinatorial library of 3-aroylcoumarins J. Org. Chem. 2006, 71, 8715-8723
40. Matos, M. J.; Vazquez-Rodriguez, S.; Santana, L.; Uriarte, E.; Fuentes-Edfuf, C.; Santos, Y.; Muñoz-Crego, A. Looking for new targets: simple coumarins as antibacterial agents Med. Chem. 2012, 8, 1140-1145
41. Matos, M. J.; Ferino, G.; Cadoni, E.; Laguna, R.; Borges, F.; Uriarte, E.; Santana, L. 8-Substituted 3-arylcoumarins as potent and selective MAO-B inhibitors: synthesis, pharmacological evaluation, and docking studies ChemMedChem 2012, 7, 464-470
42. Matos, M. J.; Vazquez-Rodriguez, S.; Uriarte, E.; Santana, L.; Viña, D. MAO inhibitory activity modulation: 3-phenylcoumarins versus 3-benzoylcoumarins Bioorg. Med. Chem. Lett. 2011, 21, 4224-4227
43. Secci, D.; Carradori, S.; Bolasco, A.; Chimenti, P.; Yañez, M.; Ortuso, F.; Alcaro, S. Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives Eur. J. Med. Chem. 2011, 46, 4846-4852
44. Serra, S.; Chicca, A.; Delogu, G.; Vazquez-Rodriguez, S.; Santana, L.; Uriarte, E.; Casu, L.; Gertsch, J. Synthesis and cytotoxic activity of non-naturally substituted 4-oxycoumarin derivatives Bioorg. Med. Chem. Lett. 2012, 22, 5791-5794
45. 3 adenosine receptor antagonists J. Pharm. Pharmacol. 2013, 65, 697-703
46. Brunet, E.; Alonso, M. T.; Juanes, O.; Velasco, O.; Rodríguez- Ubis, J. C. Novel polyaminocarboxylate chelates derived from 3-aroylcoumarins Tetrahedron 2001, 57, 3105-3116
47. Janzen, E. G.; Kotake, Y.; Randall, D. H. Stabilities of hydroxyl radical spin adducts of PBN-type spin traps Free Radical Biol. Med. 1992, 12, 169-173
48. Ou, B.; Hampsch-Woodill, M.; Prior, R. L. Development and validation of an improved oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe J. Agric. Food Chem. 2001, 49, 4619-4626
49. Clothier, R.; Gómez-Lechón, M. J.; Kinsner-Ovaskainen, A.; Kopp-Schneider, A.; O'Connor, J. E.; Prieto, P.; Stanzel, S. Comparative analysis of eight cytotoxicity assays evaluated within the ACuteTox Project Toxicol. In Vitro 2012, 27, 1347-1356
50. Singgh, R. J.; Hogg, N.; Joseph, J.; Konorev, E.; Kalyanaraman, B. The peroxynitrite generator, SIN-1, becomes a nitric oxide donor in the presence of electron acceptors Arch. Biochem. Biophys. 1999, 361, 331-339
51. M cheminformatics. http://www.molinspiration.com/services/properties. html, Bratislava, Slovak Republic.
52. Vogel, S.; Barbic, M.; Jürgenliemk, G.; Heilmann, J. Synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacological effect Eur. J. Med. Chem. 2010, 45, 2206-2213
53. Zhang, H. Y.; Wang, L. F. Theoretical elucidation of structure-activity relationship for coumarins to scavenge peroxyl radical J. Mol. Struct.: THEOCHEM 2004, 673, 199-202
54. Saprin, A. N.; Piette, L. H. Spin trapping and its application in the study of lipid peroxidation and free radical production with liver microsomes Arch. Biochem. Biophys. 1977, 180, 480-492
55. Durand, G.; Prosak, R. A.; Han, Y.; Ortial, S.; Rockenbauer, A.; Pucci, B.; Villamena, F. A. Spin trapping and cytoprotective properties of fluorinated amphiphilic carrier conjugates of cyclic versus linear nitrones Chem. Res. Toxicol. 2009, 22, 1570-1581
56. Galati, G.; Moridani, M. Y.; Chan, T. S.; O'Brien, P. J. Peroxidative metabolism of apigenin and naringenin versus luteolin and quercetin: glutathione oxidation and conjugation Free Radical Biol. Med. 2001, 30, 370-382
57. Bast, A.; Haenen, G. R. M. M. The toxicity of antioxidants and their metabolites Environ. Toxicol. Pharmacol. 2002, 11, 251-258
58. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Delivery Rev. 1997, 23, 3-25
59. Ertl, P.; Rohde, B.; Selzer, P. Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties J. Med. Chem. 2000, 43, 3714-3717
60. Buu-Hoi, N. P.; Loc, T. B.; Xuong, N. D. 3-(p -Hydroxyaroyl)- and -(p -methoxyaroyl)coumarins Bull. Soc. Chim. Fr. 1958, 3, 361-363
61. Huang, D.; Ou, B.; Hampsch-Woodill, M.; Flanagan, J. A.; Prior, R. L. High-throughput assay of oxygen radical absorbance capacity (ORAC) using a multichannel liquid handling system coupled with a microplate fluorescence reader in 96-well format J. Agric. Food Chem. 2002, 50, 4437-4444
62. Parker, T. L.; Miller, S. A.; Myers, L. E.; Miguez, F. E.; Engeseth, N. J. Evaluation of synergistic antioxidant potential of complex mixtures using oxygen radical absorbance capacity (ORAC) and electron paramagnetic resonance (EPR) J. Agric. Food Chem. 2010, 58, 209-217
63. 2/NaOH/DMSO system by electron spin resonance J. Agric. Food. Chem. 1999, 47, 4653-4656
64. Das, A.; Chakrabarty, S.; Choudhury, D.; Chakrabarti, G. 1,4-Benzoquinone (PBQ) induced toxicity in lung epithelial cells is mediated by the disruption of the microtubule network and activation of caspase-3 Chem. Res. Toxicol. 2010, 23, 1054-1066
65. Das, A.; Bhattacharya, A.; Chakrabarti, G. Cigarette smoke extract induces disruption of structure and function of tubulin-microtubule in lung epithelium cells and in vitro Chem. Res. Toxicol. 2009, 22, 446-459