Behavioral effects of 6-bromoflavanone and 5-methoxy-6,8-dibromoflavanone as anxiolytic compounds

Progress in Neuro-Psychopharmacology and Biological Psychiatry

Volumn 32, Issue 1, 2008, Pages 128-134

  Ognibene, Elisa ^a   Bovicelli, Paolo ^b   Adriani, Walter ^a   Saso, Luciano ^c   Laviola, Giovanni ^a  

^a ISTITUTO SUPERIORE DI SANITÀ   (Italy)

^b CNR   (Italy)

^c SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Anxiety; Elevated plus maze; Halogenated flavonoids; Locomotor activity

Indexed keywords

5 METHOXY 6,8 DIBROMOFLAVANONE; 6 BROMOFLAVANONE; ANXIOLYTIC AGENT; CHRYSIN; DIAZEPAM; FLAVANONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL BEHAVIOR; ANIMAL EXPERIMENT; ARTICLE; BEHAVIORAL SCIENCE; CONTROLLED STUDY; EXPLORATORY BEHAVIOR; LOCOMOTION; MALE; MAZE TEST; MOUSE; NONHUMAN; OPEN FIELD BEHAVIOR; OUTCOME ASSESSMENT; PSYCHOPHARMACOLOGY; RISK ASSESSMENT; TASK PERFORMANCE; TRANQUILIZING ACTIVITY;

ANALYSIS OF VARIANCE; ANIMALS; ANTI-ANXIETY AGENTS; ANXIETY; BEHAVIOR, ANIMAL; DIAZEPAM; DISEASE MODELS, ANIMAL; DOSE-RESPONSE RELATIONSHIP, DRUG; EXPLORATORY BEHAVIOR; FLAVANONES; MALE; MAZE LEARNING; MICE; PSYCHOMOTOR PERFORMANCE;

EID: 38349025894     PISSN: 02785846     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.pnpbp.2007.07.023     Document Type: Article

References (31)

1. Avallone R., Zanoli P., Puia G., Kleinschnitz M., Schreier P., and Baraldi M. Pharmacological profile of apigenin, a flavonoid isolated from Matricaria chamomilla. Biochem Pharmacol 59 (2000) 1387-1394
2. Barnard E.A., Skolnick P., Olsen R.W., Mohler H., Sighart W., Biggio G., et al. Subtypes of GABA receptors. Classification of the basis of subunit structure and receptor function. Pharmacol Rev 50 (1998) 291-313
3. Bovicelli P., Bernini R., Antonioletti R., and Mincione E. Selective halogenation of flavanones. Tetrahedron Lett 32 (2002) 5563-5567
4. Bowery N.G. GABAB receptor pharmacology. Annu Rev Pharmacol Toxicol 3 (1993) 109
5. File S.E. Recent developments in anxiety, stress, and depression. Pharmacol Biochem Behav 54 1 (1996) 3-12
6. File S.E., and Andrews N. Anxiolytic-like effects of 5-HT(1A) agonists in drug-naive and in benzodiazepine-experienced rats. Behav Pharmacol 5 1 (1994) 99-102
7. Gallagher D., and Primus R.J. Benzodiazepine tolerance and dependence: GABA receptor complex locus of change. Biochem Soc Symp 59 (1992) 135-151
8. Griebel G., Perrault G., Tan S., Schoemaker H., and Sanger D.J. Pharmacological studies on synthetic flavonoids: comparison with diazepam. Neuropharmacology 38 (1999) 965-977
9. Haberlein H. Flavonoids from leptospermum scoparium with affinity to the benzodiazepine receptor characterized by structure activity relationships and in vivo studies of a plant extract. Pharmazie 49 (1994) 912-922
10. Hamon M. The pharmacology of anxiety, Els Tr Div (1997)
11. Holmes A., and Rodgers R.J. Influence of spatial and temporal manipulations on the anxiolytic efficacy of chlordiazepoxide in mice previously exposed to the elevated plus-maze. Neurosci Biobehav Rev 23 7 (1999) 971-980
12. Huang X., Liu T., Gu J., Luo X., Ji R., Cao Y., et al. 3D-QSAR model of flavonoids binding at benzodiazepine site in GABAA receptors. J Med Chem 44 12 (2001) 1883-1891
13. Kahnberg P., Lager E., Rosenberg C., Schougaard J., Camet L., Sterner O., et al. Refinement and evaluation of a pharmacophore model for flavone derivatives binding to the benzodiazepine site of the GABA (A) receptor. J Med Chem 45 4 (2002) 188-201
14. Macrì S., Adriani V., Chiarotti F., and Laviola G. Risk taking during exploration of a plus-maze is greater in adolescent than in juvenile or adult mice. Anim Behav 64 (2002) 541-546
15. Marder M., Viola H., Wasowski C., Wolfman C., Waterman P.G., Cassels B.K., et al. 6-Bromoflavone, a high affinity ligand for the central benzodiazepine receptors is a member of a family of active flavonoids. Biochem Biophys Res Commun 223 (1996) 384-389
16. Marder M., Estiù G., Blanch L., Viola H., Wasowski C., Medina J.H., et al. Molecular modeling and QSAR analysis of the interaction of flavone derivatives with the benzodiazepine binding site of the GABAa receptor complex. Bioorg Med Chem (2001) 323-325
17. Marder M., Viola H., Wasowski C., Fernandez S., Medina J.H., and Paladini A.C. 6-methylapigenin and hesperidin: new valeriana flavonoids with activity on the CNS. Pharmacol Biochem Behav 75 3 (2003) 537-545
18. Medina J.H., Viola H., Wolfman C., Marder M., Wasowski C., Calvo D., et al. Overview-flavonoids: a new family of benzodiazepine receptor ligands. Neurochem Res 22 (1997) 419-425
19. Mohler H., Knoflac F., Paysan K., Motejlek K., Benke D., Luscher B., et al. Heterogeneity of GABA receptors. Neurochem Res 20 (1995) 631-638
20. Paladini A.C., Marder M., Viola H., Wolfman C., Wasowski C., and Medina J.H. Flavonoids and the central nervous system: from forgotten factors to potent anxiolytic compounds. J Pharm Pharmacol 51 5 (1999) 519-526
21. Pellow S., Chopin P., File S.E., and Briley M. Validation of open-closed arm entries in an elevated plus-maze, as a measure of anxiety in the rat. J Neurosci Methods 14 (1985) 149-167
22. Rodgers R.J., Cole J.C., Aboualfa K., and Stephenson L.H. Ethopharmacological analysis of the effects of putative "anxiogenic" agents in the mouse elevated plus-maze. Pharmacol Biochem Behav 52 4 (1995) 805-813
23. Sieghart W. Multiplicty of GABA receptors. Trends Pharmacol Sci 10 (1989) 407-409
24. Viola H., Wasowski C., Levi de Stein M., Wolfman C., Silveira R., Dajas F., et al. Apigenin, a component of Matricaria recutita flowers, is a central benzodiazepine receptors-ligand with anxiolytic effects. Planta Med 61 (1995) 213-216
25. Viola H., Marder M., Nunez J., Izquierdo L., Wasowski C., Wolfman C., et al. 6-Methyl-3′-bromoflavone, a high-affinity ligand for the benzodiazepine binding site of the GABA (A) receptor with some antagonistic properties. Biochem Biophys Res Commun 262 (1999) 643-646
26. Viola H., Marder M., Wasowski C., Giorgi O., Paladini A.C., and Medina J.H. 6,3′-dibromoflavone and 6-nitro-3′-bromoflavone: new additions to the 6,3′-disubstituted flavone family of high-affinity ligands of the brain benzodiazepine binding site with agonistic properties. Biochem Biophys Res Commun 273 (2000) 694-698
27. Wang Q., Han Y., and Hong X. Ligands of the GABAa receptor benzodiazepine binding site. CNS Drug Rev 5 - 2 (1999) 125-144
28. Wolfman C., Viola H., Paladini A., Dajas F., and Medina J.H. Possible anxiolyticeffects of chrysin, a central benzodiazepine receptor ligand isolated from Passiflora coerulea. Pharmacol Biochem Behav 47 (1994) 1-4
29. Wolfman C., Viola H., Marder M., Ardenghi P., Wasowski C., Schroder N., et al. Pharmacological characterization of 6-bromo-3′-nitroflavone, a synthetic flavonoid with high affinity for the benzodiazepine receptors. Pharmacol Biochem Behav 61 (1998) 239-246
30. Woods J.H., Kats J.L., and Winger G. Benzodiazepines: use, abuse and consequences. Pharmacol Rev 44 (1992) 151-347
31. Zanoli P., Avallone R., and Baraldi M. Behavioral characterisation of the flavonoids apigenin and chrysin. Fitoterapia 71 (2000) 117-123