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Volumn 75, Issue , 2014, Pages 222-232

Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: Synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity

Author keywords

Alkylbisammonio quaternary salts; Analgesic activity; In vitro pharmacology; In vivo pharmacology; Muscarinic agonists; Muscarinic receptor subtypes

Indexed keywords

ALKYLBISAMMONIO QUATERNARY SALTS; ANALGESIC ACTIVITY; IN VITRO PHARMACOLOGY; IN VIVO PHARMACOLOGY; MUSCARINIC AGONISTS; MUSCARINIC RECEPTOR SUBTYPES;

EID: 84894109151     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.01.032     Document Type: Article
Times cited : (24)

References (39)
  • 1
    • 36549075610 scopus 로고    scopus 로고
    • Modulation of pain transmission by G-protein-coupled receptors
    • DOI 10.1016/j.pharmthera.2007.09.003, PII S0163725807001908
    • H.-L. Pan, Z.-Z. Wu, H.-Y. Zhou, S.-R. Chen, H.-M. Zhang, and D.-P. Li Modulation of pain transmission by G-protein-coupled receptors Pharmacol. Ther. 117 2008 141 161 and references cited therein (Pubitemid 350192674)
    • (2008) Pharmacology and Therapeutics , vol.117 , Issue.1 , pp. 141-161
    • Pan, H.-L.1    Wu, Z.-Z.2    Zhou, H.-Y.3    Chen, S.-R.4    Zhang, H.-M.5    Li, D.-P.6
  • 2
    • 84856677201 scopus 로고    scopus 로고
    • Muscarinic pain pharmacology: Realizing the promise of novel analgesics by overcoming old challenges
    • A.D. Fryer, A. Christopoulos, N.M. Nathanson, Springer-Verlag Berlin Heidelberg and references cited therein
    • D.F. Fiorino, and M. Garcia-Guzman Muscarinic pain pharmacology: realizing the promise of novel analgesics by overcoming old challenges A.D. Fryer, A. Christopoulos, N.M. Nathanson, Muscarinic Receptors, Handbook of Experimental Pharmacology vol. 208 2012 Springer-Verlag Berlin Heidelberg 191 221 and references cited therein
    • (2012) Muscarinic Receptors, Handbook of Experimental Pharmacology , vol.208 VOL. , pp. 191-221
    • Fiorino, D.F.1    Garcia-Guzman, M.2
  • 6
    • 33644845396 scopus 로고    scopus 로고
    • 4 receptor subtypes in regulation of GABAergic inputs to dorsal horn neurons revealed by muscarinic receptor knockout mice
    • 4 receptor subtypes in regulation of GABAergic inputs to dorsal horn neurons revealed by muscarinic receptor knockout mice Mol. Pharmacol. 69 2006 1048 1055 (Pubitemid 43363881)
    • (2006) Molecular Pharmacology , vol.69 , Issue.3 , pp. 1048-1055
    • Zhang, H.-M.1    Chen, S.-R.2    Matsui, M.3    Gautam, D.4    Wess, J.5    Pan, H.-L.6
  • 9
    • 34548362105 scopus 로고    scopus 로고
    • Muscarinic acetylcholine receptors: Mutant mice provide new insights for drug development
    • DOI 10.1038/nrd2379, PII NRD2379
    • J. Wess, R.M. Eglen, and D. Gautam Muscarinic acetylcholine receptors: mutant mice provide new insights for drug development Nat. Rev. Drug Discovery 6 2007 721 733 (Pubitemid 47342315)
    • (2007) Nature Reviews Drug Discovery , vol.6 , Issue.9 , pp. 721-733
    • Wess, J.1    Eglen, R.M.2    Gautam, D.3
  • 12
    • 0035793826 scopus 로고    scopus 로고
    • Evidence for specific analgesic activity of a muscarinic agonist selected among a new series of acetylenic derivatives
    • DOI 10.1016/S0024-3205(01)00973-0, PII S0024320501009730
    • E. Barocelli, V. Ballabeni, S. Bertoni, M. De Amici, and M. Impicciatore Evidence for specific analgesic activity of a muscarinic agonist selected among a new series of acetylenic derivatives Life Sci. 68 2001 1775 1785 (Pubitemid 32245626)
    • (2001) Life Sciences , vol.68 , Issue.15 , pp. 1775-1785
    • Barocelli, E.1    Ballabeni, V.2    Bertoni, S.3    De Amici, M.4    Impicciatore, M.5
  • 15
    • 0023819931 scopus 로고
    • 3H-N-methylscopolamine binding in guinea-pig myocardium by an antidote against organophosphorus intoxication
    • 3H-N-methylscopolamine binding in guinea-pig myocardium by an antidote against organophosphorus intoxication J. Pharmacol. Toxicol. 63 1988 163 168
    • (1988) J. Pharmacol. Toxicol. , vol.63 , pp. 163-168
    • Jepsen, K.1    Lüllmann, H.2    Mohr, K.3    Pfeffer, J.4
  • 17
    • 0037435052 scopus 로고    scopus 로고
    • Systematic development of high affinity bis(ammonio)alkane-type allosteric enhancers of muscarinic ligand binding
    • DOI 10.1021/jm021017q
    • M. Muth, W. Bender, O. Scharfenstein, U. Holzgrabe, E. Balaktova, C. Tränkle, and K. Mohr Systematic development of high affinity bis(ammonio)alkane-type allosteric enhancers of muscarinic ligand binding J. Med. Chem. 46 2003 1031 1040 (Pubitemid 36423149)
    • (2003) Journal of Medicinal Chemistry , vol.46 , Issue.6 , pp. 1031-1040
    • Muth, M.1    Bender, W.2    Scharfenstein, O.3    Holzgrabe, U.4    Balatkova, E.5    Trankle, C.6    Mohr, K.7
  • 18
    • 15444377439 scopus 로고    scopus 로고
    • Muscarinic allosteric enhancers of ligand binding: Pivotal pharmacophoric elements in hexamethonio-type agents
    • DOI 10.1021/jm049616f
    • M. Muth, M. Sennwitz, K. Mohr, and U. Holzgrabe Muscarinic allosteric enhancers of muscarinic ligand: pivotal pharmacophoric elements in hexamethonio-type agents J. Med. Chem. 48 2005 2212 2217 (Pubitemid 40396348)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.6 , pp. 2212-2217
    • Muth, M.1    Sennwitz, M.2    Mohr, K.3    Holzgrabe, U.4
  • 21
    • 77954243052 scopus 로고    scopus 로고
    • Convergent, short synthesis of the muscarinic superagonist iperoxo
    • J. Klöckner, J. Schmitz, and U. Holzgrabe Convergent, short synthesis of the muscarinic superagonist iperoxo Tetrahedron Lett. 51 2010 3470 3472
    • (2010) Tetrahedron Lett. , vol.51 , pp. 3470-3472
    • Klöckner, J.1    Schmitz, J.2    Holzgrabe, U.3
  • 22
    • 33745809867 scopus 로고    scopus 로고
    • Hydroxy-1,2,5-oxadiazolyl moiety as bioisoster of the carboxy function. Synthesis, ionization constants, and pharmacological characterization of γ-aminobutyric acid (GABA) related compounds
    • DOI 10.1021/jm051288b
    • M.L. Lolli, S.L. Hansen, B. Rolando, B. Nielsen, P. Wellendorph, K. Madsen, O. Miller Larsen, U. Kristiansen, R. Fruttero, A. Gasco, and T.N. Johansen Hydroxy-1,2,5-oxadiazolyl moiety as bioisoster of the carboxy function. Synthesis, ionization constants, and pharmacological characterization of γ-aminobutyric acid (GABA) related compounds J. Med. Chem. 49 2006 4442 4446 (Pubitemid 44036687)
    • (2006) Journal of Medicinal Chemistry , vol.49 , Issue.14 , pp. 4442-4446
    • Lolli, M.L.1    Hansen, S.L.2    Rolando, B.3    Nielsen, B.4    Wellendorph, P.5    Madsen, K.6    Larsen, O.M.7    Kristiansen, U.8    Fruttero, R.9    Gasco, A.10    Johansen, T.N.11
  • 25
    • 0031594565 scopus 로고    scopus 로고
    • 2 receptor binding of the selective antagonist AF-DX 384: Possible involvement of the common allosteric site
    • 2 receptor binding of the selective antagonist AF-DX 384: possible involvement of the common allosteric site Mol. Pharmacol. 53 1998 304 312 (Pubitemid 28099741)
    • (1998) Molecular Pharmacology , vol.53 , Issue.2 , pp. 304-312
    • Trankle, C.1    Andresen, I.2    Lambrecht, G.3    Mohr, K.4
  • 26
    • 0023821640 scopus 로고
    • 2 receptors mediating opposite effects on neuromuscular transmission in rabbit vas deferens
    • 2 receptors mediating opposite effects on neuromuscular transmission in rabbit vas deferens Eur. J. Pharmacol. 151 1988 205 221
    • (1988) Eur. J. Pharmacol. , vol.151 , pp. 205-221
    • Eltze, M.1
  • 28
    • 0031774720 scopus 로고    scopus 로고
    • International union of pharmacology. XVII. Classification of muscarinic acetylcholine receptors
    • M.P. Caulfield, and N.J.M. Birdsall International Union of Pharmacology. XVII. Classification of muscarinic acetylcholine receptors Pharmacol. Rev. 50 1998 279 290 (Pubitemid 28304029)
    • (1998) Pharmacological Reviews , vol.50 , Issue.2 , pp. 279-290
    • Caulfield, M.P.1    Birdsall, N.J.M.2
  • 29
    • 84894148511 scopus 로고    scopus 로고
    • This functional test is commonly used to characterize ligands for M1 receptors. However, Melchiorre et al. Suggested that inhibition of the neurogenic contractions in this tissue preparation could be mediated by M4 receptors
    • This functional test is commonly used to characterize ligands for M1 receptors. However, Melchiorre et al. suggested that inhibition of the neurogenic contractions in this tissue preparation could be mediated by M4 receptors [Br. J. Pharmacol. 132 (2001) 1009-1016].
    • (2001) Br. J. Pharmacol. , vol.132 , pp. 1009-1016
  • 30
    • 28844431542 scopus 로고    scopus 로고
    • Search for dual function inhibitors for Alzheimer's disease: Synthesis and biological activity of acetylcholinesterase inhibitors of pyridinium-type and their Aβ fibril formation inhibition capacity
    • DOI 10.1016/j.bmc.2005.08.034, PII S0968089605007881
    • P. Kapková, V. Alptüzün, P. Frey, E. Erciyas, and U. Holzgrabe Search for dual function inhibitors for Alzheimer's disease: synthesis and biological activity of acetylcholinesterase inhibitors of pyridinium-type and their Aβ fibril formation inhibition capacity Bioorg. Med. Chem. 14 2006 472 478 and references cited therein (Pubitemid 41767607)
    • (2006) Bioorganic and Medicinal Chemistry , vol.14 , Issue.2 , pp. 472-478
    • Kapkova, P.1    Alptuzun, V.2    Frey, P.3    Erciyas, E.4    Holzgrabe, U.5
  • 31
  • 32
    • 70349845276 scopus 로고    scopus 로고
    • Mood and anxiety related phenotypes in mice: Characterization using behavioral tests
    • T.D. Gould, D.T. Dao, and C.E. Kovacsics Mood and anxiety related phenotypes in mice: characterization using behavioral tests Neuromethods 42 2009 1 20
    • (2009) Neuromethods , vol.42 , pp. 1-20
    • Gould, T.D.1    Dao, D.T.2    Kovacsics, C.E.3
  • 35
    • 0027276894 scopus 로고
    • Central and peripheral mediation of hypothermia, tremor and salivation induced by muscarinic agonists in mice
    • C. Sánchez, and E. Meier Central and peripheral mediation of hypothermia, tremor and salivation induced by muscarinic agonists in mice Pharmacol. Toxicol. 72 1993 262 267 (Pubitemid 23181607)
    • (1993) Pharmacology and Toxicology , vol.72 , Issue.4-5 , pp. 262-267
    • Sanchez, C.1    Meier, E.2
  • 36
    • 0034705511 scopus 로고    scopus 로고
    • New analogues of oxotremorine and oxotremorine-M estimation of their in vitro affinity and efficacy at muscarinic receptor subtypes
    • DOI 10.1016/S0024-3205(00)00661-5, PII S0024320500006615
    • E. Barocelli, V. Ballabeni, S. Bertoni, C. Dallanoce, M. De Amici, C. De Micheli, and M. Impicciatore New analogues of oxotremorine and oxotremorine-M: estimation of their in vitro affinity and efficacy at muscarinic receptor subtypes Life Sci. 67 2000 717 723 (Pubitemid 30451910)
    • (2000) Life Sciences , vol.67 , Issue.6 , pp. 717-723
    • Barocelli, E.1    Ballabeni, V.2    Bertoni, S.3    Dallanoce, C.4    De Amici, M.5    De Micheli, C.6    Impicciatore, M.7
  • 37
    • 73649209211 scopus 로고
    • Cumulative dose-response curves. II. Technique for the making of dose-response curves in isolated organs and the evaluation of drug parameters
    • J.M. Van Rossum Cumulative dose-response curves. II. Technique for the making of dose-response curves in isolated organs and the evaluation of drug parameters Arch. Int. Pharmacodyn. Ther. 143 1963 299 330
    • (1963) Arch. Int. Pharmacodyn. Ther. , vol.143 , pp. 299-330
    • Van Rossum, J.M.1
  • 38
    • 84981848149 scopus 로고
    • Comparison of dissociation constants and of relative efficacies of selected agonists acting on parasympathetic receptors
    • R.F. Furchgott, and P. Bursztyn Comparison of dissociation constants and of relative efficacies of selected agonists acting on parasympathetic receptors Ann. N. Y. Acad. Sci. 144 1967 882 898
    • (1967) Ann. N. Y. Acad. Sci. , vol.144 , pp. 882-898
    • Furchgott, R.F.1    Bursztyn, P.2


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