Michael acceptor approach to the design of new salvinorin A-based high affinity ligands for the kappa-opioid receptor

European Journal of Medicinal Chemistry

Volumn 85, Issue , 2014, Pages 818-829

  Polepally, Prabhakar R ^a   Huben, Krzysztof ^a,d   Vardy, Eyal ^b   Setola, Vincent ^b   Mosier, Philip D ^c   Roth, Bryan L ^b   Zjawiony, Jordan K ^a  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

^c VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

^d LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

and mu opioid receptors; Delta; Kappa; Michael acceptor type ligands; Molecular modeling; Salvinorin A and B

Indexed keywords

2 O ACRYLOYLSALVINORIN B; 2 O CINNAMOYLSALVINORIN; 2 O CROTONOYLSALVINORIN B; 2 O METHACRYLOYLSALVINORIN; 2 O(2' METHYL 3' BUTENOYL)SALVINORIN B; 2 O(2'' METHOXYCINNAMOYL)SALVINORIN B; 2 O(2'' NITROCINNAMOYL)SALVINORIN B; 2 O(2'' TRIFLUOROMETHYLCINNAMOYL)SALVINORIN B; 2 O(2'',4'' DIMETHOXYCINNAMOYL)SALVINORIN B; 2 O(2'',5'' DIMETHOXYCINNAMOYL)SALVINORIN; 2 O(2',3' DIMETHYLACRYLOYL)SALVINORIN B; 2 O(3' BUTENOYL)SALVINORIN B; 2 O(3' METHYLBUT 3' ENOYL)SALVINORIN B; 2 O(3'',4'' DIOXYMETHYLENECINNAMOYL)SALVINORIN B; 2 O(3'',4'',5'' TRIMETHOXYCINNAMOYL)SALVINORIN B; 2 O(3',3' DIMETHYLACRYLOYL)SALVINORIN B; 2 O(4'' METHOXYCINNAMOYL)SALVINORIN B; 2 O(4'' NITROCINNAMOYL)SALVINORIN B; 2 O(4'' TRIFLUOROMETHYLCINNAMOYL)SALVINORIN B; 2 O['',5'' BIS(TRIFLUOROMETHYL)CINNAMOYL]SALVINORIN B; DELTA OPIATE RECEPTOR; ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; KAPPA OPIATE RECEPTOR; MU OPIATE RECEPTOR; NALTRINDOLE; SALVINORIN A; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG; CLERODANE DERIVATIVE; LIGAND; PROTEIN BINDING;

ARTICLE; BINDING AFFINITY; CAMP ASSAY; COMPETITIVE BINDING ASSAY; CRYSTAL STRUCTURE; DRUG BINDING SITE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; EC50; HUMAN; HUMAN CELL; MICHAEL ADDITION; MOLECULAR INTERACTION; MOLECULAR MODEL; MUTAGENESIS; RADIOASSAY; STRUCTURE ACTIVITY RELATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; HEK293 CELL LINE; METABOLISM; PROTEIN CONFORMATION; SYNTHESIS;

DITERPENES, CLERODANE; DRUG DESIGN; HEK293 CELLS; HUMANS; LIGANDS; MODELS, MOLECULAR; PROTEIN BINDING; PROTEIN CONFORMATION; RECEPTORS, OPIOID, KAPPA;

EID: 84930245171     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.07.077     Document Type: Article

References (30)

1. A. Ortega, J.F. Blount, P.S. Manchand, Salvinorin, a new trans-neoclerodane diterpene from Salvia divinorum (Labiatae), J. Chem. Soc. Perkins Trans. 1 (1982) 2505-2508.
2. B.L. Roth, K. Baner, R.B. Westkaemper, D. Siebert, K.C. Rice, S. Steinberg, P. Ernsberger, R.B. Rothman, Salvinorin A: a potent naturally occurring nonnitrogenous k opioid selective agonist, Proc. Natl. Acad. Sci. U. S. A. 99 (2002) 11934-11939.
3. C.W. Cunningham, R.B. Rothman, T.E. Prisinzano, Neuropharmacology of the naturally occurring k-opioid hallucinogen salvinorin A, Pharmacol. Rev. 63 (2011) 316-347.
4. J. Fichna, K. Lewellyn, F. Yan, B.L. Roth, J.K. Zjawiony, Synthesis and biological evaluation of new salvinorin A analogues incorporating natural amino acids, Bioorg. Med. Chem. Lett. 21 (2011) 160-163.
5. K.M. Lovell, K.M. Prevatt-Smith, A. Lozama, T.E. Prisinzano, Synthesis of neoclerodane diterpenes and their pharmacological effects, Top. Curr. Chem. 299 (2011) 141-185.
6. A. Lozama, C.W. Cunningham, M.J. Caspers, J.T. Douglas, C.M. Dersch, R.B. Rothman, T.E. Prisinzano, Opioid receptor probes derived from cycloaddition of the hallucinogen natural product salvinorin A, J. Nat. Prod. 74 (2011) 718-726.
7. P.R. Polepally, K. White, E. Vardy, B.L. Roth, D. Ferreira, J.K. Zjawiony, Kappaopioid receptor-selective dicarboxylic ester-derived salvinorin A ligands, Bioorg. Med. Chem. Lett. 23 (2013) 2860-2862.
8. T.E. Prisinzano, Neoclerodanes as atypical opioid receptor ligands. 2012 David W. Robertson award for excellence in medicinal chemistry, J. Med. Chem. 56 (2013) 3435-3443.
9. H. Wu, D. Wacker, M. Mileni, V. Katritch, G.W. Han, E. Vardy, W. Liu, A.A. Thompson, X.-P. Huang, F.I. Carroll, S.W. Mascarella, R.B. Westkaemper, P.D. Mosier, B.L. Roth, V. Cherezov, R.C. Stevens, Structure of the human kopioid receptor in complex with JDTic, Nature 485 (2012) 327-332.
10. F. Yan, R.V. Bikbulatov, V. Mocanu, N. Dicheva, C.E. Parker, W.C. Wetsel, P.D. Mosier, R.B. Westkaemper, J.A. Allen, J.K. Zjawiony, B.L. Roth, Structurebased design, synthesis, and biochemical and pharmacological characterization of novel salvinorin A analogues as active state probes of the k-opioid receptor, Biochemistry 48 (2009) 6898-6908.
11. S. Amslinger, The tunable functionality of a, b-unsaturated carbonyl compounds enables their differential application in biological systems, Chem- MedChem 5 (2010) 351-356.
12. C.-Y. Cheng, S.-C. Wu, L.-W. Hsin, S.W. Tam, Selective reversible and irreversible ligands for the k opioid receptor, J. Med. Chem. 35 (1992) 2243-2247.
13. G.A. Koolpe, W.L. Nelson, T.L. Gioannini, L. Angel, E.J. Simon, Diastereomeric 6- desoxy-6-spiro-a-methylene-g-butyrolactone derivatives of naltrexone and oxymorphone. Selective irreversible inhibition of naltrexone binding in an opioid receptor preparation by a conformationally restricted Michael acceptor ligand, J. Med. Chem. 27 (1984) 1718-1723.
14. J. Pitha, L. Szabo, Z. Szurmai, W. Buchowiecki, J.W. Kusiak, Alkylating prazosin analogue: irreversible label for a1-adrenoceptors, J. Med.Chem. 32 (1989) 96-100.
15. J. Singh, R.C. Petter, T.A. Baillie, A. Whitty, The resurgence of covalent drugs, Nat. Rev. Drug Discov. 10 (2011) 307-317.
16. C. Avonto, O. Taglialatela-Scafati, F. Pollastro, A. Minassi, V. Di Marzo, L. De Petrocellis, G. Appendino, An NMR spectroscopic method to identify and classify thiol-trapping agents: revival of Michael acceptors for drug discovery? Angew. Chem. Int. Ed. Engl. 50 (2011) 467-471.
17. W. Chu, J. Rothfuss, A. d'Avignon, C. Zeng, D. Zhou, R.S. Hotchkiss, R.H. Mach, Isatin sulfonamide analogs containing a Michael addition acceptor: a new class of caspase 3/7 inhibitors, J. Med. Chem. 50 (2007) 3751-3755.
18. R.D. Couch, R.G. Browning, T. Honda, G.W. Gribble, D.L. Wright, M.B. Sporn, A.C. Anderson, Studies on the reactivity of CDDO, a promising new chemopreventive and chemotherapeutic agent: implications for a molecular mechanism of action, Bioorg. Med. Chem. Lett. 15 (2005) 2215-2219.
19. B. Shi, M.F. Greaney, Reversible Michael addition of thiols as a new tool for dynamic combinatorial chemistry, Chem. Commun. (2005) 886-888.
20. K. Tidgewell, C.E. Groer, W.W. Harding, A. Lozama, M. Schmidt, A. Marquam, J. Heimstra, J.S. Partilla, C.M. Dersch, R.B. Rothman, L.M. Bohn, T.E. Prisinzano, Herkinorin analogues with differential b-arrestin-2 interactions, J. Med. Chem. 51 (2008) 2421-2431.
21. W.W. Harding, K. Tidgewell, N. Byrd, H. Cobb, C.M. Dersch, E.R. Butelman, R.B. Rothman, T.E. Prisinzano, Neoclerodane diterpenes as a novel scaffold for m opioid receptor ligands, J. Med. Chem. 48 (2005) 4765-4771.
22. K. Tidgewell, W.W. Harding, M. Schmidt, K.G. Holden, D.J. Murry, T.E. Prisinzano, A facile method for the preparation of deuterium labeled salvinorin A: synthesis of [2, 2, 2-2H3]-salvinorin A, Bioorg. Med. Chem. Lett. 14 (2004) 5099-5102.
23. E. Arkoudis, M. Stratakis, Synthesis of cordiaquinones B, C, J, and K on the basis of a bioinspired approach and the revision of the relative stereochemistry of cordiaquinone C, J. Org. Chem. 73 (2008) 4484-4490.
24. W.E. Truce, P.S. Bailey Jr., The mechanism of alcoholysis of carboxylic acid halides in the presence of triethylamine, J. Org. Chem. 34 (1969) 1341-1345.
25. F. Yan, P.D. Mosier, R.B. Westkaemper, J. Stewart, J.K. Zjawiony, T. Vortherms, D.J. Sheffler, B.L. Roth, Identification of the molecular mechanisms by which the diterpenoid salvinorin A binds to k-opioid receptors, Biochemistry 44 (2005) 8643-8651.
26. V. Katritch, V. Cherezov, R.C. Stevens, Diversity and modularity of G proteincoupled receptor structures, Trends Pharmacol. Sci. 33 (2012) 17-27.
27. A. Negri, M.-L. Rives, M.J. Caspers, T.E. Prisinzano, J.A. Javitch, M. Filizola, Discovery of a novel selective kappa-opioid receptor agonist using crystal structure-based virtual screening, J. Chem. Inf. Model. 53 (2013) 521-526.
28. E. Vardy, P.D. Mosier, K.J. Frankowski, H. Wu, V. Katritch, R.B. Westkaemper, J. Aubé, R.C. Stevens, B.L. Roth, Chemotype-selective modes of action of k-opioid receptor agonists, J. Biol. Chem. 288 (2013) 34470-34483.
29. J.A. Ballesteros, H. Weinstein, Integrated methods for the construction of three-dimensional models and computational probing of structure-function relationships in G-protein coupled receptors, Methods Neurosci. 25 (1995) 366-428.
30. L.M. Kutrzeba, V.T. Karamyan, R.C. Speth, J.S. Williamson, J.K. Zjawiony, In vitro studies on metabolism of salvinorin A, Pharm. Biol. 47 (2009) 1078-1084.