In vitro binding affinities of a series of flavonoids for m-opioid receptors. Antinociceptive effect of the synthetic flavonoid 3,3-dibromoflavanone in mice

Neuropharmacology

Volumn 72, Issue , 2013, Pages 9-19

  Higgs, Josefina ^a   Wasowski, Cristina ^a   Loscalzo, Leonardo M ^a   Marder, Mariel ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

3,3 Dibromoflavanone; Acute treatment; Antinociceptive effects; Natural and synthetic flavonoids; Opioid receptors

Indexed keywords

3,3 DIBROMOFLAVANONE; 6 METHYLFLAVONE; ACETIC ACID; ADRENERGIC RECEPTOR; ANTINOCICEPTIVE AGENT; APIGENIN; AURANTIIN; CHRYSIN; DIOSMETIN; ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; FLAVANONE; FLAVONE; FLAVONOID; HESPERETIN; HESPERIDIN; HESPERIDIN METHYLCHALCONE; INDOMETACIN; KETANSERIN; MU OPIATE RECEPTOR; NALTREXONE; NALTRINDOLE; NARINGENIN; NEOHESPERIDIN; NORBINALTORPHIMINE; PRAZOSIN; QUERCETIN; RUTOSIDE; SEROTONIN 2 RECEPTOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; YOHIMBINE;

ANIMAL BEHAVIOR; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; BEHAVIORAL SCIENCE; BINDING AFFINITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG INHIBITION; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; GASTROINTESTINAL TRANSIT; HOT PLATE TEST; IN VITRO STUDY; IN VIVO STUDY; MALE; MOTOR COORDINATION; MOTOR PERFORMANCE; MOUSE; NOCICEPTION; NONHUMAN; PAIN; PHARMACOLOGICAL PARAMETERS; PRIORITY JOURNAL; PROTEIN FUNCTION; PROTEIN INDUCTION; RECEPTOR BLOCKING; SEDATION; TRANQUILIZING ACTIVITY; TREATMENT OUTCOME;

EID: 84884895169     PISSN: 00283908     EISSN: 18737064     Source Type: Journal    
DOI: 10.1016/j.neuropharm.2013.04.020     Document Type: Article

References (59)

1. Abbott, F., Melzack, R., Samue, C., 1982. Morphine analgesia in the tail-flick and formalin pain test is mediated by different neural systems. Exp. Neurol. 75 (3), 644-651. (Pubitemid 12185590)
2. Bannon, A.W., Malmberg, A.B., 2007. Models of nociception: hot plate, tail flick, and formalin tests in rodents. Curr. Protoc. Neurosci. S41, 8.9.1-8.9.16.
3. Barrot, M., 2012. Tests and models of nociception and pain in rodents. Neuroscience 211, 39-50.
4. Bourin, M., Masse, F., Dailly, E., Hascoët, M., 2005. Anxiolytic-like effect of milnacipran in the four-plate test in mice: mechanism of action. Pharmacol. Biochem. Behav. 81, 645-656. (Pubitemid 40973787)
5. Bradford, M.M., 1976. A dye binding assay for protein. Anal. Biochem. 72, 248-254.
6. Carroll, I., Mackey, S., Gaeta, R., 2007. The role of adrenergic receptors and pain: the good, the bad, and the unknown. Semin. Anesth. Perioper. Med. Pain 26, 17-21.
7. Carter, R.B., 1991. Differentiating analgesic and non-analgesic drug activities on rat hot plate: effect of behavioral endpoint. Pain 47, 211-220.
8. Chou, T.C., Chang, L.P., Li, C.Y., Wong, C.S., Yang, S.P., 2003. The anti-inflammatory and analgesic effects of baicalin in carrageenan-evoked thermal hyperalgesia. Anesth. Analg. 97, 1724-1729.
9. Coughenour, L.L., Maclean, J.R., Parker, R.B., 1977. A new device for the rapid measurement of impaired motor function in mice. Pharmacol. Biochem. Behav. 6, 351-353. (Pubitemid 8084883)
10. De Diesbach, H., Kramer, H., 1945. Sur quelques dérivés de la tétrahydro-quinoléine. Helv. Chim. Acta 28 (1), 1399-1405.
11. Fernández, S.P., Wasowski, C., Paladini, A.C., Marder, M., 2006. Central nervous system depressant action of flavonoid glycosides. Eur. J. Pharmacol. 539, 168-176. (Pubitemid 44208813)
12. File, S.E., Pellow, S., 1985. The effects of triazolobenzodiazepines in two animal tests of anxiety and in the hole board. Br. J. Pharmacol. 86, 729-735. (Pubitemid 16235389)
13. Guzmán-Gutiérrez, S.L., Navarrete, A., 2009. Pharmacological exploration of the sedative mechanism of hesperidin identified as the active principle of Citrus sinensis flowers. Planta Med. 75 (4), 295-301.
14. Harbone, J.B., Williams, C., 2000. Advances in flavonoid research since 1992. Phytochemistry 5, 481-505.
15. Havsteen, B.H., 2002. The biochemistry and medical significance of the flavonoids. harmacol. Ther. 96, 67-202. (Pubitemid 35356564)
16. Ioja, E., Tourwé, D., Kertész, I., Tóth, G., Borsodi, A., Benyhe, S., 2007. Novel diastereomeric opioid tetrapeptides exhibit differing pharmacological activity profiles. Brain Res. Bull. 74, 119-129. (Pubitemid 47187918)
17. Jäger, A.K., Lasse, S., 2011. Flavonoids and the CNS. Molecules 16, 1471-1485.
18. Jürgensen, S., Dalbó, S., Angers, P., Santos, A.R., Ribeiro-do-Valle, R.M., 2005.
19. Involvement of 5-HT2 receptors in the antinociceptive effect of Uncaria tomentosa. Pharmacol. Biochem. Behav. 81 (3), 466-477.
20. Katavic, P.L., Navarro, H., Lamb, K., Prisinzano, T.E., 2007. Flavonoids as opioid receptor ligands: identification and preliminary structureeactivity relationships. J. Nat. Prod. 70 (8), 1278-1282. (Pubitemid 47401567)
21. Kaur, R., Singh, D., Chopra, K., 2005. Participation of alpha-2 receptors in the antinociceptive activity of quercetin. J. Med. Food 8 (4), 529-532. (Pubitemid 43121908)
22. Kieffer, B., Gavériaux-Ruff, C., Befort, K., Massotte, D., Becker, J., 2009. Brain opioid receptor systems: molecular and functional aspects. Eur. Neuropsychopharmacol. 19, S1-S2.
23. Koster, R., Anderson, M., Beer, E.J., 1959. Acetic acid for analgesic screening. Fed. Proc. 18, 412-418.
24. Kromer, W., 1988. Endogenous and exogenous opioids in the control of gastrointestinal motility and secretion. Pharmacol. Rev. 40 (2), 121-182.
25. Lakhlani, P.P., Macmillan, L.B., Guo, T.Z., McCool, B.A., Lovinger, D., Maze, M., Limbird, L.E., 1997. Substitution of a mutant a2a-adrenergic receptor via "hit and run" gene targeting reveals the role of this subtype in sedative, analgesic, and anesthetic-sparing responses in vivo. Proc. Natl. Acad. Sci. of U. S. A. 94, 9950-9955.
26. Le Bars, D., Gozariu, M., Cadden, S.W., 2001. Animal models of nociception. Pharmacol. Rev. 53 (4), 597-652. (Pubitemid 33136239)
27. Lister, R.G., 1987. The use of a plus maze to measure anxiety in the mouse. Psychopharmacology (Berl) 92, 180-185. (Pubitemid 17072893)
28. Loscalzo, L.M., Wasowski, C., Paladini, A.C., Marder, M., 2008. Opioid receptors are involved in the sedative and antinociceptive effects of hesperidin as well as in its potentiation with benzodiazepines. Eur. J. Pharmacol. 580, 306-313.
29. Loscalzo, L.M., Yow, T.T., Wasowski, C., Chebib, M., Marder, M., 2011. Hesperidin induces antinociceptive effect in mice and its aglicone, hesperetin, binds to mopioid receptor and inhibits GIRK1/2 currents. Pharmacol. Biochem. Behav. 99, 333-341.
30. Manara, L., Bianchi, G., Ferretti, P., Tavani, A., 1986. Inhibition of gastrointestinal transit by morphine in rats results primarily from direct drug action on gut opioid sites. J. Pharmacol. Exp. Ther. 237 (3), 945-949. (Pubitemid 16088118)
31. Marder, M., Paladini, A.C., 2002. GABAA-receptor ligands of flavonoid structure. Curr. Top. Med. Chem. 2, 853-867.
32. Marder, M., Viola, H.,Wasowski, C., Fernández, S.P., Medina, J.H., Paladini, A.C., 2003. 6-Methylapigenin and hesperidin: new valeriana flavonoids with activity on the CNS. Pharmacol. Biochem. Behav. 75, 537-545. (Pubitemid 36936888)
33. Martinez-Vazquez, M., Ramirez Apan, T.O., Aguilar, H., Bye, R., 1996. Analgesic and antipyretic activities of an aqueous extract and of the flavone linarin of Buddleia cordata. Planta Med. 62, 137-140. (Pubitemid 26163217)
34. Meotti, F.C., Luiz, A.P., Pizzolatti, M.G., Kassuya, C.A.L., Calixto, J.B., Santos, A.R.S., 2006. Analysis of the antinociceptive effect of the flavonoid myricitrin: evidence for a role of the L-arginine-nitric oxide and protein kinase C pathways. J. Pharmacol. Exp. Ther. 316, 789-796. (Pubitemid 43131007)
35. Milano, J., Rossato, M.F., Oliveira, S.M., Drewes, C., Machado, P., Beck, P., Zanatta, N., Martins, M.A., Mello, C.F., Rubin, M.A., Ferreira, J., Bonacorso, H.G., 2008. Antinociceptive action of 4-methyl-5-trifluoromethyl-5- hydroxy-4, 5-dihydro-1Hpyrazole methylester in models of inflammatory pain in mice. Life Sci. 83 (21- 22), 739-746.
36. Millan, M.J., 1994. Serotonin and pain: evidence that activation of 5HT1A receptors does not elicit antinociception against noxious thermal, mechanical and chemical stimuli in mice. Pain 58, 45-61.
37. Moskowitz, A.S., Goodmans, R.R., 1984. Light microscopic autoradiographic localization of m and d opioid binding sites in the mouse central nervous system. J. Neurosci. 4, 1331-1342. (Pubitemid 14076088)
38. Murray, C.W., Porreca, F., Cowan, A., 1988. Methodological refinements to the mouse paw formalin tests: an animal model of tonic pain. J. Pharmacol. Method 20 (2), 175-186.
39. Neubert, J.K., Rossi, H.L., Pogar, J., Jenkins, A.C., Caudle, R.M., 2007. Effects of mu- and kappa-2 opioid receptor agonists on pain and rearing behaviors. Behav. Brain Funct. 3, 49-59.
40. Ognibene, E., Bovicelli, P., Adriani,W., Saso, L., Laviola, G., 2008. Behavioral effects of 6-bromoflavanone and 5-methoxy-6,8-dibromoflavanone as anxiolytic compounds. Prog. Neuropsychopharmacol. Biol. Psychiatry 32 (1), 128-134.
41. Ormazábal, M.J., Goicoechea, C., Alfaro, M.J., Sánchez, E., Martín, M.I., 1999. Study of mechanisms of calcitonin analgesia in mice. Involvement of 5-HT3 receptors. Brain Res. 845, 130-138. (Pubitemid 29486452)
42. Peng, X., Knapp, B.I., Bidlack, J.M., Neumeyer, J.L., 2007. Pharmacological properties of bivalent ligands containing butorphan linked to nalbuphine, naltrexone, and naloxone at m, d, and k opioid receptors. J. Med. Chem. 50, 2254-2258. (Pubitemid 46683079)
43. Philipp, M., Brede, M., Hein, L., 2002. Physiological significance of a2-adrenergic receptor subtype diversity: one receptor is not enough. Am. J. Physiol. Regul. Integr. Comp. Physiol. 283, R287-R295. (Pubitemid 34863874)
44. Rathee, P., Chaudhary, H., Rathee, S., Rathee, D., Kumar, V., Kohli, A., 2009. Mechanism of action of flavonoids as anti-inflammatory agents: a review. Inflamm. Allergy Drug Targets 8, 229-235.
45. Schloss, P., Williams, D.C., 1998. The serotonin transporter: a primary target for antidepressant drugs. J. Psychopharmacol. 12 (2), 115-121. (Pubitemid 28312567)
46. Schreiber, S., Backer, M.M., Pick, C.G., 1999. The antinociceptive effect of venlafaxine in mice is mediated through opioid and adrenergic mechanisms. Neurosci. Lett. 273, 85-88. (Pubitemid 29428113)
47. Schulz, R.,Wuster, M., Herz, A., 1979. Centrally and peripherally mediated inhibition of intestinal motility by opioids. Naunyn-Schmiedeberg's Arch. Pharmacol. 308, 255-260. (Pubitemid 10227363)
48. Takemori, A.E., Portoghese, P.S., 1984. Comparative antagonism by naltrexone and naloxone of m, k, and d agonists. Eur. J. Pharmacol. 104, 101-104. (Pubitemid 14006467)
49. Tanoue, A., Koshimizu, T., Tsujimoto, G., 2002. Transgenic studies of a1-adrenergic receptor subtype function. Life Sci. 71, 2207-2215. (Pubitemid 35246209)
50. Thirugnanasambantham, P., Viswanathan, S., Ramaswamy, S., Krishnamurty, V., Mythirayee, C., Kameswaran, L., 1993. Analgesic activity of certain flavone derivatives: a structureeactivity study. Clin. Exp. Pharmacol. Physiol. 20 (1), 59-63. (Pubitemid 23015733)
51. Tjølsen, A., 1992. The formalin test: an evaluation of the method. Pain 51 (1), 5-17.
52. Umamaheswari, S., Viswanathan, S., Sathiyasekaran, B.W.C., Parvathavarthini, S., Ramaswamy, S., 2006. Antinociceptive activity of certain dihydroxy flavones. Indian J. Pham. Sci. 68 (6), 749-753. (Pubitemid 46457272)
53. Vidyalakshmi, K., Kamalakannan, P., Viswanathan, S., Ramaswamy, S., 2010. Antinociceptive effect of certain dihydroxy flavones in mice. Pharmacol. Biochem. Behav. 96 (1), 1-6.
54. Viswanathan, S., Sambantham, P.T., Reddy, K., Kameswaran, L., 1984. Gossypininduced analgesia in mice. Eur. J. Pharmacol. 98, 289-291.
55. Vogel, H.G., Vogel, W.H., Schölkens, B.A., Sandow, J., Müller, G., Vogel, W.F., 2002. Drug Discovery and Evaluation: Pharmacological Assays, second ed. Springer,Heidelberg.
56. Wasowski, C., Marder, M., 2012. Flavonoids as GABAA receptor ligands: the whole story? J. Exp. Pharmacol. 4, 9-24.
57. Webster, D.E., He, Y., Chen, S., Pauli, G.F., Farnsworth, N.R., Wanga, Z.J., 2011. Opioidergic mechanisms underlying the actions of Vitex agnus-castus L. Biochem. Pharmacol. 81, 170-177.
58. Yoburn, B.C., Lutfy, K., Candido, J., 1991. Species differences in m and d opioid receptors. Eur. J. Pharmacol. 193 (1), 105-108.
59. Yue, C.Q., Ye, J., Li, C.L., Li, R.T., Sun, Q., 2007. Antinociceptive effects of the novel spirocyclopiperazinium salt compound LXM-10 in mice. Pharmacol. Biochem. Behav. 86, 643-650. (Pubitemid 46829317)