Synthesis and pharmacological evaluation of potent and enantioselective σ1 and σ2 ligands

Farmaco

Volumn 56, Issue 3, 2001, Pages 181-189

  Marrazzo, Agostino ^a   Prezzavento, Orazio ^a   Pasquinucci, Lorella ^a   Vittorio, Franco ^a   Ronsisvalle, Giuseppe ^a  

^a UNIVERSITY OF CATANIA   (Italy)

Author keywords

Ligands; Sigma receptors; Stereoselectivity

Indexed keywords

1 PHENYL 2 CYCLOPROPYLMETHYLAMINE; 1 PHENYL 2 CYCLOPROPYLMETHYLAMINE DERIVATIVE; 1,3 BIS(2 METHYLPHENYL)GUANIDINE; 2 [4 METHOXY 3 (2 PHENYLETHOXY)PHENYL] N,N DIPROPYLETHYLAMINE; AC 915; CARBOXYMETHYLESTER; CB 184; CYCLOPROPANE; DOPAMINE 2 RECEPTOR; ESTER DERIVATIVE; HYDROXYMETHYL; IBOGAINE; N ALLYLNORMETAZOCINE; NALOXONE; OPIATE RECEPTOR; PENTAZOCINE; SIGMA 1 OPIATE RECEPTOR; SIGMA 2 OPIATE RECEPTOR; SIGMA OPIATE RECEPTOR; SIGMA RECEPTOR LIGAND; SPIPERONE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CIS ISOMER; CONTROLLED STUDY; DNA SEQUENCE; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; GUINEA PIG; NONHUMAN; NUCLEOTIDE SEQUENCE; STEREOCHEMISTRY;

AMINO ACID SEQUENCE; ANALGESICS, OPIOID; CYCLAZOCINE; HUMANS; LIGANDS; MOLECULAR SEQUENCE DATA; RECEPTORS, DOPAMINE D2; RECEPTORS, SIGMA; STEREOISOMERISM;

EID: 0035303494     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(01)01039-4     Document Type: Article

References (22)

1. Walker J.M., Bowen W.D., Walker F.O., Matsumoto R.R., De Costa B., Rice K.C. Sigma receptors: biology and function. Pharmacol. Rev. 42:1990;355-402.
2. Quirion R., Bowen W.D., Itzhak Y., Junien J.L., Musacchio J.M., Rothman R.B., Su T.P., Torn S.W., Taylor D.P. A proposal for the classification of sigma binding sites. Trends Pharmacol. Sci. 13:1992;85-86.
3. Leitner M.L., Hohmann A.G., Patrick S.L., Walker J.M. Regional variation in the ratio of sigma 1 to sigma 2 binding in rat brain. Eur. J. Pharm. 259:1994;65-69.
4. Wolfe S.A., Culp S.G. Jr., De Souza E.B. Sigma-receptors in endocrine organs: identification, characterization, and autoradiographic localization in rat pituitary, adrenal, testis and ovary. Endocrinology. 124:1989;1160-1172.
5. Monnet F.P., De Costa B.R., Bowen W.D. Differentiation of sigma ligand-activated receptor subtypes that modulate NMDA-evoked [3H]-noradrenaline release in rat hippocampal slices. Br. J. Pharmacol. 119:1996;65-72.
6. Maurice T., Lockhart B.P. Neuroprotective and anti-amnesic potentials of sigma (sigma) receptor ligands. Prog. Neuro-Psychopharmacol. Biol. Psychiat. 21:1997;69-102.
7. King M., Pan Y.X., Mei J., Chang A., Xu J., Pasternak G.W. Enhanced kappa-opioid receptor-mediated analgesia by antisense targeting the sigma 1 receptor. Eur. J. Pharmacol. 331:1997;R5-R6.
8. Hanner M., Moebius F.F., Flandorfer A., Knaus H.G., Striessnig J., Kempner E., Glossmann H. Purification, molecular cloning, and expression of the mammalian sigma 1-binding site. Proc. Natl. Acad. Sci. USA. 93:1996;8072-8077.
9. Kekuda R., Prasad P.D., Fei Y., Leibach F.H., Ganapathy V. Cloning and functional expression of the human type 1 sigma receptor (hSigmaR1). Biochem. Biophys. Res. Commun. 229:1996;553-558.
10. Moebius F.F., Striessnig J., Glossmann H. The mysteries of sigma receptors: new family members reveal a role in cholesterol synthesis. Trends Pharmacol. Sci. 18:1997;67-70.
11. Torrence-Campbell C., Bowen W.D. Differential solubilization of the rat liver sigma 1 and sigma 2 receptors: retention of sigma 2 sites in particulate fractions. Eur. J. Pharmacol. 304:1996;201-210.
12. Walker J.M., Bowen W.D., Patrick S.L., Williams W.E., Mascarella S.W., Bai X., Carroll F.I. A comparison of (-)-deoxybenzomorphan devoid of opiate activity with their dextrorotatory phenolic counterparts suggest role of sigma 2 receptors in motor function. Eur. J. Pharmacol. 231:1993;61-68.
13. Vilner B.J., John C.S., Bowen W.D. Sigma 1 and sigma 2 receptors are expressed in a wide variety of human and rodent tumor cell lines. Cancer Res. 55:1995;408-413.
14. B.R. De Costa, X.S. He, in: Y. Itzhak (Ed.), Sigma Receptors, Academic Press, San Diego, CA, 1994, Chapter 3, pp. 45-111.
15. 1 binding sites in guinea pig brain. Eur. J. Pharmacol. 251:1994;R1-R2.
16. Maeda D.Y., Williams W., Bowen W.D., Coop A. A sigma-1 receptor selective analogue of BD 1008. A potential substitute for (+)-opioids in sigma receptor binding assay. Bioorg. Med. Chem. Lett. 10:2000;17-18.
17. Berta C.M., Vilner B.J., Mattson M.V., Bowen W.D., Becketts K., Xu H., Rothman R.B., Flippen-Anderson J.L., Rice K.C. (E)-8-benzylidene derivatives of 2-methyl-5-(3-hydroxyphenyl)morphan: highly selective ligands for the sigma 2 receptor subtype. J. Med. Chem. 38:1995;4776-4785.
18. Itzhak Y., Ali S.F. Effect of ibogainer on the various sites of the NMDA receptor complex and sigma binding sites in rat brain. Ann. NY Acad. Sci. 844:1998;245-251.
19. Ronsisvalle G., Pasquinucci L., Pappalardo M.S., Vittorio F., Fronza G., Romagnoli C., Pistacchio E., Spampinato S., Ferri S. Non-peptide ligands for opioid receptors. Design of kappa-specific agonist. J. Med. Chem. 36:1993;1860-1865.
20. Ronsisvalle G., Prezzavento O., Pasquinucci L., Marrazzo A., Vittorio F., Gomez-Vidal J.A., Carboni L., Spampinato S. CCB, a novel specific kappa opioid agonist, which discriminate between opioid and sigma 1 recognition sites. Life Sci. 16:1995;1487-1495.
21. Ronsisvalle G., Prezzavento O., Pasquinucci L., Pappalardo M.S., Marrazzo A., Vittorio F., Carboni L., Spampinato S. Synthesis of (+)-(1′R,2′S) and (1′S,2′R)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-3-[[2′- (alkoxycarbonyl]-2′-phenylcyclopropyl]-methyl]-2,6-methano-3-benzazocin-8- ol. Comparison of the affinities for sigma 1 and opioid receptors with diastereoisomeric MPCB and CCB. Farmaco. 52:(6-7):1997;471-476.
22. Ronsisvalle G., Marrazzo A., Prezzavento O., Pasquinucci L., Falcucci B., Di Toro R., Spampinato S. Substituted 1-phenyl-2cyclopropylmethylamines with high affinity and selectivity for sigma sites. Bioorg. Med. Chem. 8:2000;2124-2134.