Insights into structure-activity relationship of GABA A receptor modulating coumarins and furanocoumarins

European Journal of Pharmacology

Volumn 668, Issue 1-2, 2011, Pages 57-64

  Singhuber, Judith ^a   Baburin, Igor ^a   Ecker, Gerhard F ^a   Kopp, Brigitte ^a   Hering, Steffen ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

(Furano) coumarin; GABA A receptor; Osthole; Oxypeucedanin; Pharmacophore model; Voltage clamp technique

Indexed keywords

4 AMINOBUTYRIC ACID A RECEPTOR; AURAPTENE; BERGAMOTTIN; BERGAPTEN; BERGAPTOL; COUMARIN; COUMARIN DERIVATIVE; FLUMAZENIL; FUROCOUMARIN DERIVATIVE; ISOBERGAPTEN; ISOIMPERATORIN; ISOPIMPINELLIN; OSTHOLE; OSTRUTHIN; OSTRUTHIOL; OXYPEUCEDANIN; PENTOSALEN; PHELLOPTERIN; PIMPINELLIN; SCOPOLETIN; UMBELLIFERONE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CHLORIDE CURRENT; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG BINDING SITE; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG STRUCTURE; FEMALE; HYDROPHOBICITY; MOLECULAR MODEL; NONHUMAN; OOCYTE; PHARMACOPHORE; PRIORITY JOURNAL; PROTEIN EXPRESSION; RECEPTOR UPREGULATION; STRUCTURE ACTIVITY RELATION; VOLTAGE CLAMP; XENOPUS LAEVIS;

ALLOSTERIC REGULATION; ANIMALS; BENZODIAZEPINES; BINDING SITES; CHLORIDES; COUMARINS; ELECTRIC CONDUCTIVITY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OOCYTES; PSORALENS; RECEPTORS, GABA-A; STRUCTURE-ACTIVITY RELATIONSHIP; XENOPUS LAEVIS;

EID: 80052049199     PISSN: 00142999     EISSN: 18790712     Source Type: Journal    
DOI: 10.1016/j.ejphar.2011.06.034     Document Type: Article

References (47)

1. M.M. Abouelzahab, M.A. Metwally, A.M. Dawidar, M. Abdelmogib, and E.A. Abumustafa Photochemical-reactions of the natural furocoumarin, imperatorin Bull. Chem. Soc. Jpn. 60 1987 4433 4435
2. I. Baburin, S. Beyl, and S. Hering Automated fast perfusion of Xenopus oocytes for drug screening Pflugers Arch. Eur. J. Phy. 453 2006 117 123 (Pubitemid 44454892)
3. I. Baburin, S. Khom, E. Timin, A. Hohaus, W. Sieghart, and S. Hering Estimating the efficiency of benzodiazepines on GABA(A) receptors comprising gamma1 or gamma2 subunits Br. J. Pharmacol. 155 2008 424 433
4. R. Baur, U. Simmen, M. Senn, U. Sequin, and E. Sigel Novel plant substances acting as beta subunit isoform-selective positive allosteric modulators of GABA(A) receptors Mol. Pharmacol. 68 2005 787 792 (Pubitemid 41206033)
5. O. Bergendorff, K. Dekermendjian, M. Nielsen, R. Shan, R. Witt, J. Ai, and O. Sterner Furanocoumarins with affinity to brain benzodiazepine receptors in vitro Phytochemistry 44 1997 1121 1124 (Pubitemid 27097057)
6. A.J. Boileau, T. Li, C. Benkwitz, C. Czajkowski, and R.A. Pearce Effects of [gamma]2S subunit incorporation on GABA(A) receptor macroscopic kinetics Neuropharmacology 44 2003 1003 1012 (Pubitemid 36570424)
7. K. Dekermendjian, J. Ai, M. Nielsen, O. Sterner, R. Shan, and M.-R. Witt Characterization of the furanocoumarin phellopterin as a rat brain benzodiazepine receptor partial agonist in vitro Neurosci. Lett. 219 1996 151 154 (Pubitemid 26405555)
8. M.A. Demel, O. Kraemer, P. Ettmayer, E. Haaksma, and G.F. Ecker Ensemble rule-based classification of substrates of the human ABC-transporter ABCB1 using simple physicochemical descriptors Mol. Inf. 29 2010 233 242
9. G. Eisenbrand Toxicological assessment of furocoumarins in foodstuffs Mol. Nutr. Food Res. 51 2007 367 373 (Pubitemid 47083672)
10. F. Epifano, G. Molinaro, S. Genovese, R.T. Ngomba, F. Nicoletti, and M. Curini Neuroprotective effect of prenyloxycoumarins from edible vegetables Neurosci. Lett. 443 2008 57 60
11. S.P. Fernandez, K.N. Mewett, J.R. Hanrahan, M. Chebib, and G.A.R. Johnston Flavan-3-ol derivatives are positive modulators of GABA(A) receptors with higher efficacy for the alpha2 subtype and anxiolytic action in mice Neuropharmacology 55 2008 900 907
12. M. Gebauer Synthesis and structure-activity relationships of novel warfarin derivatives Bioorg. Med. Chem. 15 2007 2414 2420 (Pubitemid 46240909)
13. R.E. Granger, E.L. Campbell, and G.A.R. Johnston (+)- and (-)-borneol: efficacious positive modulators of GABA action at human recombinant [alpha]1[beta]2[gamma]2 L GABA(A) receptors Biochem. Pharmacol. 69 2005 1101 1111 (Pubitemid 40349022)
14. J. Hirsh, J. Dalen, D.R. Anderson, L. Poller, H. Bussey, J. Ansell, and D. Deykin Oral anticoagulants: mechanism of action, clinical effectiveness, and optimal therapeutic range Chest 119 2001 8S 21S (Pubitemid 32154192)
15. M.S. Huen, K.M. Hui, J.W. Leung, E. Sigel, R. Baur, J.T. Wong, and H. Xue Naturally occurring 2'-hydroxyl-substituted flavonoids as high-affinity benzodiazepine site ligands Biochem. Pharmacol. 66 2003 2397 2407 (Pubitemid 37456746)
16. G.A.R. Johnston, J.R. Hanrahan, M. Chebib, R.K. Duke, K.N. Mewett, and S.J. Enna Modulation of Ionotropic GABA Receptors by Natural Products of Plant Origin Advances in Pharmacology 2006 Elsevier San Diego, CA 285 316
17. S. Khom, I. Baburin, E.N. Timin, A. Hohaus, W. Sieghart, and S. Hering Pharmacological properties of GABA(A) receptors containing gamma1 subunits Mol. Pharmacol. 69 2006 640 649 (Pubitemid 43121961)
18. S. Khom, I. Baburin, E. Timin, A. Hohaus, G. Trauner, B. Kopp, and S. Hering Valerenic acid potentiates and inhibits GABA(A) receptors: molecular mechanism and subunit specificity Neuropharmacology 53 2007 178 187 (Pubitemid 47125958)
19. E.R. Korpi, G. Gründer, and H. Lüddens Drug interactions at GABA(A) receptors Prog. Neurobiol. 67 2002 113 159
20. I. Kostova Synthetic and natural coumarins as cytotoxic agents Curr. Med. Chem. Anticancer Agents 5 2005 29 46 (Pubitemid 40081292)
21. I. Kostova Synthetic and natural coumarins as antioxidants Mini-Rev. Med. Chem. 6 2006 365 374
22. Y. Li, I. Plitzko, J. Zaugg, S. Hering, and M. Hamburger HPLC-based activity profiling for GABA(A) receptor modulators: a new dihydroisocoumarin from Haloxylon scoparium J. Nat. Prod. 73 2010 768 770
23. J.J. Luszczki, K. Glowniak, and S.J. Czuczwar Time-course and dose-response relationships of imperatorin in the mouse maximal electroshock seizure threshold model Neurosci. Res. 59 2007 18 22 (Pubitemid 47285389)
24. J.J. Luszczki, K. Glowniak, and S.J. Czuczwar Imperatorin enhances the protective activity of conventional antiepileptic drugs against maximal electroshock-induced seizures in mice Eur. J. Pharmacol. 574 2007 133 139 (Pubitemid 47575522)
25. J.J. Luszczki, M. Andres-Mach, W. Cisowski, I. Mazol, K. Glowniak, and S.J. Czuczwar Osthole suppresses seizures in the mouse maximal electroshock seizure model Eur. J. Pharmacol. 607 2009 107 109
26. J.J. Luszczki, E. Wojda, M. Andres-Mach, W. Cisowski, M. Glensk, K. Glowniak, and S.J. Czuczwar Anticonvulsant and acute neurotoxic effects of imperatorin, osthole and valproate in the maximal electroshock seizure and chimney tests in mice: a comparative study Epilepsy Res. 85 2009 293 299
27. R.M. McKernan, and P.J. Whiting Which GABA(A)-receptor subtypes really occur in the brain? Trends Neurosci. 19 1996 139 143
28. I. Mody, and R.A. Pearce Diversity of inhibitory neurotransmission through GABA(A) receptors Trends Neurosci. 27 2004 569 575 (Pubitemid 39149827)
29. R.D.H. Murray, J. Méndez, and S.A. Brown The Natural Coumarins-Occurrence, Chemistry and Biochemistry 1982 John Wiley and Sons New York 20 53
30. R. O'Kennedy, and R.D. Thorne Coumarins: Biology, Applications and Mode of Action 1997 Wiley Chichester 23 66
31. R.W. Olsen, and W. Sieghart GABA(A) receptors: subtypes provide diversity of function and pharmacology Neuropharmacology 56 2009 141 148
32. X.L. Piao, I.H. Park, S.H. Baek, H.Y. Kim, M.K. Park, and J.H. Park Antioxidative activity of furanocoumarins isolated from Angelicae dahuricae J. Ethnopharmacol. 93 2004 243 246 (Pubitemid 38962411)
33. C.M. Priestley, E.M. Williamson, K.A. Wafford, and D.B. Sattelle Thymol, a constituent of thyme essential oil, is a positive allosteric modulator of human GABA(A) receptors and a homo-oligomeric GABA receptor from Drosophila melanogaster Br. J. Pharmacol. 140 2003 1363 1372 (Pubitemid 38067843)
34. J.E. Sadler Medicine: K is for koagulation Nature 427 2004 493 494
35. W. Sieghart Structure and pharmacology of gamma-aminobutyric acidA receptor subtypes Pharmacol. Rev. 47 1995 181 234
36. W. Sieghart, and G. Sperk Subunit composition, distribution and function of GABA(A) receptor subtypes Curr. Top. Med. Chem. 2 2002 795 816
37. W. Sieghart, and S.J. Enna Structure, Pharmacology, and Function of GABA(A) Receptor Subtypes Advances in Pharmacology 2006 Elsevier San Diego, CA 231 263
38. J. Simon, H. Wakimoto, N. Fujita, M. Lalande, and E.A. Barnard Analysis of the set of GABA(A) receptor genes in the human genome J. Biol. Chem. 279 2004 41422 41435 (Pubitemid 39313583)
39. P.N. Thanh, W. Jin, G. Song, K. Bae, and S.S. Kang Cytotoxic coumarins from the root of Angelica dahurica Arch. Pharm. Res. 27 2004 1211 1215
40. G. Trauner, S. Khom, I. Baburin, B. Benedek, S. Hering, and B. Kopp Modulation of GABAA receptors by valerian extracts is related to the content of valerenic acid Planta Med. 74 2008 19 24 (Pubitemid 351251378)
41. V.B. Tsassi, H. Hussain, B.Y. Meffo, S.F. Kouam, E. Dongo, B. Schulz, I.R. Greene, and K. Krohn Antimicrobial coumarins from the stem bark of Afraegle paniculata Nat. Prod. Commun. 5 2010 559 561
42. S. Vogl, M. Zehl, P. Picker, E. Urban, C. Wawrosch, G. Reznicek, J. Saukel, and B. Kopp Identification and quantification of coumarins in Peucedanum ostruthium (L.) Koch by HPLC-DAD and HPLC-DAD-MS Food Chem. 59 2011 4371 4377
43. J. Widelski, M. Popova, K. Graikou, K. Glowniak, and I. Chinou Coumarins from Angelica lucida L. -antibacterial activities Molecules 14 2009 2729 2734
44. L.L. Yang, M.C. Wang, L.G. Chen, and C.C. Wang Cytotoxic activity of coumarins from the fruits of Cnidium monnieri on leukemia cell lines Planta Med. 69 2003 1091 1095
45. E. Yarnell, and K. Abascal Plant Coumarins: Myths and Realities Alternative & Complementary Therapies 15 2009 24 30
46. J. Zaugg, I. Baburin, B. Strommer, H.J. Kim, S. Hering, and M. Hamburger HPLC-based activity profiling: discovery of piperine as a positive GABA(A) receptor modulator targeting a benzodiazepine-independent binding site J. Nat. Prod. 73 2010 185 191
47. J. Zaugg, E. Eickmeier, D.C. Rueda, S. Hering, and M. Hamburger HPLC-based activity profiling of Angelica pubescens roots for new positive GABA(A) receptor modulators in Xenopus oocytes Fitoterapia 82 2011 434 440