메뉴 건너뛰기




Volumn 42, Issue 25, 1999, Pages 5224-5234

Analogues of neuroactive polyamine wasp toxins that lack inner basic sites exhibit enhanced antagonism toward a muscle-type mammalian nicotinic acetylcholine receptor

Author keywords

[No Author keywords available]

Indexed keywords

IONOTROPIC RECEPTOR; N (12 AMINODODECYL) 4 HYDROXY ALPHA [(1 OXOBUTYL)AMINO]BENZENEPROPANAMIDE; NICOTINIC RECEPTOR; PHILANTHOTOXIN 343; POLYAMINE; UNCLASSIFIED DRUG; WASP VENOM;

EID: 0033576734     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9903747     Document Type: Article
Times cited : (44)

References (57)
  • 2
    • 0000170939 scopus 로고
    • Paralysis caused by the digger wasp Philanthus
    • Rathmayer, W. Paralysis caused by the digger wasp Philanthus. Nature 1962, 196, 1148-1151.
    • (1962) Nature , vol.196 , pp. 1148-1151
    • Rathmayer, W.1
  • 3
    • 0015118313 scopus 로고
    • Neuromuscular block in insects caused by the venom of the digger wasp Philanthus triangulum F
    • Piek, T.; Mantel, P.; Engels, E. Neuromuscular block in insects caused by the venom of the digger wasp Philanthus triangulum F. Comput. Gen. Pharmacol. 1971, 2, 317-331.
    • (1971) Comput. Gen. Pharmacol. , vol.2 , pp. 317-331
    • Piek, T.1    Mantel, P.2    Engels, E.3
  • 8
    • 0026704376 scopus 로고
    • Synthesis of novel and photolabile philanthotoxin analogues: Glutamate receptor antagonists
    • Choi, S.-K.; Goodnow, R. A.; Kalivretenos, A.; Chiles, G. W.; Fushiya, S.; Nakanishi, K. Synthesis of novel and photolabile philanthotoxin analogues: glutamate receptor antagonists. Tetrahedron 1992, 23, 4793-4822.
    • (1992) Tetrahedron , vol.23 , pp. 4793-4822
    • Choi, S.-K.1    Goodnow, R.A.2    Kalivretenos, A.3    Chiles, G.W.4    Fushiya, S.5    Nakanishi, K.6
  • 9
    • 0027745352 scopus 로고
    • Synthesis of philanthotoxin analogues with a branched polyamine moiety
    • Kalivretenos, A. G.; Nakanishi, K. Synthesis of philanthotoxin analogues with a branched polyamine moiety. J. Org. Chem. 1993, 58, 6596-6608.
    • (1993) J. Org. Chem. , vol.58 , pp. 6596-6608
    • Kalivretenos, A.G.1    Nakanishi, K.2
  • 10
    • 0027309501 scopus 로고
    • Synthesis and assay of hybrid analogues of argiotoxin-636 and philanthotoxin-433: Glutamate receptor antagonists
    • Choi, S. K.; Nakanishi, K.; Usherwood, P. N. R. Synthesis and assay of hybrid analogues of argiotoxin-636 and philanthotoxin-433: glutamate receptor antagonists. Tetrahedron 1993, 49, 5777-5790.
    • (1993) Tetrahedron , vol.49 , pp. 5777-5790
    • Choi, S.K.1    Nakanishi, K.2    Usherwood, P.N.R.3
  • 11
    • 0027258899 scopus 로고
    • The physiological action of analogues of philanthotoxin-4.3.3 at insect nicotinic acetylcholine receptors
    • Benson, J. A.; Kaufmann, L.; Hue, B.; Pelhate, M.; Schuermann, F.; Gsell, L.; Piek, T. The physiological action of analogues of philanthotoxin-4.3.3 at insect nicotinic acetylcholine receptors. Comp. Biochem. Physiol. 1993, 105C, 303-310.
    • (1993) Comp. Biochem. Physiol. , vol.105 C , pp. 303-310
    • Benson, J.A.1    Kaufmann, L.2    Hue, B.3    Pelhate, M.4    Schuermann, F.5    Gsell, L.6    Piek, T.7
  • 12
    • 0001679024 scopus 로고    scopus 로고
    • Synthesis of philanthotoxin analogues with bulky heads including porphyrins. Self-assembly monitored by circular dichroism
    • Huang, D.; Matile, S.; Berova, N.; Nakanishi, K. Synthesis of philanthotoxin analogues with bulky heads including porphyrins. Self-assembly monitored by circular dichroism. Heterocycles 1996, 42, 723-736.
    • (1996) Heterocycles , vol.42 , pp. 723-736
    • Huang, D.1    Matile, S.2    Berova, N.3    Nakanishi, K.4
  • 13
    • 0030865713 scopus 로고    scopus 로고
    • Synthesis and pharmacological activity of philanthotoxin-343 analogues: Antagonists of ionotropic glutamate receptors
    • Huang, D.; Jiang, H.; Nakanishi, K.; Usherwood, P. N. R. Synthesis and pharmacological activity of philanthotoxin-343 analogues: antagonists of ionotropic glutamate receptors. Tetrahedron 1997, 53, 12391-12404.
    • (1997) Tetrahedron , vol.53 , pp. 12391-12404
    • Huang, D.1    Jiang, H.2    Nakanishi, K.3    Usherwood, P.N.R.4
  • 15
    • 0025974854 scopus 로고
    • Structure-activity relationship of philanthotoxins. I. Pre- and postsynaptic inhibition of the locust neuromuscular transmission
    • Karst, H.; Piek, T.; Van Marie, J.; Lind, A.; Van Weeren-Kramer, J. Structure-activity relationship of philanthotoxins. I. Pre- and postsynaptic inhibition of the locust neuromuscular transmission. Comp. Biochem. Physiol. 1991, 98C, 471-477.
    • (1991) Comp. Biochem. Physiol. , vol.98 C , pp. 471-477
    • Karst, H.1    Piek, T.2    Van Marie, J.3    Lind, A.4    Van Weeren-Kramer, J.5
  • 16
    • 0025981621 scopus 로고
    • Structure-activity relationship of philanthotoxins. II. Effects on the glutamate gated ion channels of the locust muscle fiber membrane
    • Karst, H.; Piek, T. Structure-activity relationship of philanthotoxins. II. Effects on the glutamate gated ion channels of the locust muscle fiber membrane. Comp. Biochem. Physiol. 1991, 98C, 479-489.
    • (1991) Comp. Biochem. Physiol. , vol.98 C , pp. 479-489
    • Karst, H.1    Piek, T.2
  • 17
    • 0024433132 scopus 로고
    • Philanthotoxins, a new class of neuroactive polyamines, block nicotinic transmission in the insect CNS
    • Piek, T.; Hue, B. Philanthotoxins, a new class of neuroactive polyamines, block nicotinic transmission in the insect CNS. Comp. Biochem. Physiol. 1989, 93C, 403-306.
    • (1989) Comp. Biochem. Physiol. , vol.93 C , pp. 403-1306
    • Piek, T.1    Hue, B.2
  • 18
    • 0025203424 scopus 로고
    • Philanthotoxin blocks quisqualate-, AMPA- and kainate-, but not NMDA-, induced excitation of rat brainstem neurons in vivo
    • Jones, M. G.; Anis, N. A.; Lodge, D. Philanthotoxin blocks quisqualate-, AMPA- and kainate-, but not NMDA-, induced excitation of rat brainstem neurons in vivo. Br J. Pharmacol. 1990, 101, 968-970.
    • (1990) Br J. Pharmacol. , vol.101 , pp. 968-970
    • Jones, M.G.1    Anis, N.A.2    Lodge, D.3
  • 19
    • 0027861025 scopus 로고
    • Selective antagonism of native and cloned kainate and NMDA receptors by polyamine-containing toxins
    • Brackley, P. T. H.; Bell, D. R.; Choi, S. K.; Nakanishi, K.; Usherwood, P. N. R. Selective antagonism of native and cloned kainate and NMDA receptors by polyamine-containing toxins. J. Pharmacol Exp. Ther. 1993, 266, 1573-1580.
    • (1993) J. Pharmacol Exp. Ther. , vol.266 , pp. 1573-1580
    • Brackley, P.T.H.1    Bell, D.R.2    Choi, S.K.3    Nakanishi, K.4    Usherwood, P.N.R.5
  • 20
    • 0030426845 scopus 로고    scopus 로고
    • Block of α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptors by polyamines and polyamine toxins
    • Washburn, M. S.; Dingledine, R. Block of α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptors by polyamines and polyamine toxins. J. Pharmacol. Exp. Ther. 1996, 278, 669-678.
    • (1996) J. Pharmacol. Exp. Ther. , vol.278 , pp. 669-678
    • Washburn, M.S.1    Dingledine, R.2
  • 21
    • 0342647787 scopus 로고    scopus 로고
    • Permeation and block of rat GluR6 glutamate receptor channels by internal and external polyamines
    • Bähring, R.; Bowie, D.; Benveniste, M.; Mayer, M. L. Permeation and block of rat GluR6 glutamate receptor channels by internal and external polyamines. J. Physiol. 1997, 502, 575-589.
    • (1997) J. Physiol. , vol.502 , pp. 575-589
    • Bähring, R.1    Bowie, D.2    Benveniste, M.3    Mayer, M.L.4
  • 22
    • 0442315095 scopus 로고    scopus 로고
    • An analysis of philanthotoxin block for recombinant rat GluR6(Q) glutamate receptor channels
    • Bähring, R.; Mayer, M. L. An analysis of philanthotoxin block for recombinant rat GluR6(Q) glutamate receptor channels. J. Physiol. 1998, 509, 635-650.
    • (1998) J. Physiol. , vol.509 , pp. 635-650
    • Bähring, R.1    Mayer, M.L.2
  • 23
    • 0029945947 scopus 로고    scopus 로고
    • Polyamine amides are neuroprotective in cerebellar granule cell cultures challenged with excitatory amino acids
    • Green, A. C.; Nakanishi, K.; Usherwood, P. N. R. Polyamine amides are neuroprotective in cerebellar granule cell cultures challenged with excitatory amino acids. Brain Res. 1996, 717, 135-146.
    • (1996) Brain Res. , vol.717 , pp. 135-146
    • Green, A.C.1    Nakanishi, K.2    Usherwood, P.N.R.3
  • 26
    • 0029138044 scopus 로고
    • Labeling studies of photolabile philanthotoxins with nicotinic acetylcholine receptors: Mode of interaction between toxin and receptor
    • Choi, S.-K.; Kalivretenos, A. G.; Usherwood, P. N. R.; Nakanishi, K. Labeling studies of photolabile philanthotoxins with nicotinic acetylcholine receptors: mode of interaction between toxin and receptor. Chem. Biol. 1995, 2, 23-32.
    • (1995) Chem. Biol. , vol.2 , pp. 23-32
    • Choi, S.-K.1    Kalivretenos, A.G.2    Usherwood, P.N.R.3    Nakanishi, K.4
  • 27
    • 0030050675 scopus 로고    scopus 로고
    • Neuroactive polyamine wasp toxins: Nuclear magnetic resonance spectroscopic analysis of the protolytic properties of philanthotoxin-343
    • Jaroszewski, J. W.; Matzen, L.; Frølund, B.; Krogsgaard-Larsen, P. Neuroactive polyamine wasp toxins: nuclear magnetic resonance spectroscopic analysis of the protolytic properties of philanthotoxin-343. J. Med. Chem. 1996, 39, 515-521.
    • (1996) J. Med. Chem. , vol.39 , pp. 515-521
    • Jaroszewski, J.W.1    Matzen, L.2    Frølund, B.3    Krogsgaard-Larsen, P.4
  • 28
    • 0002370299 scopus 로고
    • Synthesis of d-philanthotoxin
    • Tong, Y. C. Synthesis of d-philanthotoxin. Pesticide Sci. 1988, 24, 340-343.
    • (1988) Pesticide Sci. , vol.24 , pp. 340-343
    • Tong, Y.C.1
  • 29
    • 0024951414 scopus 로고
    • Philanthotoxin-343 - An analogue of a toxin from Philanthus triangulum: A practical synthesis of a potent glutamate antagonist
    • Blagbrough, I. S.; Bycroft, B. W.; Mather, A. J.; Usherwood, P. N. R. Philanthotoxin-343 - an analogue of a toxin from Philanthus triangulum: a practical synthesis of a potent glutamate antagonist. J. Pharm. Pharmacol. 1989, 41 (Suppl), 95P.
    • (1989) J. Pharm. Pharmacol. , vol.41 , Issue.SUPPL.
    • Blagbrough, I.S.1    Bycroft, B.W.2    Mather, A.J.3    Usherwood, P.N.R.4
  • 31
    • 0028459077 scopus 로고
    • Syntheses of O-methacryoyl-N-acyl tyrosines and their adhesiveness to un-etched human dentin
    • Tanaka, J.; Suzuki, K.; Nakai, H. Syntheses of O-methacryoyl-N-acyl tyrosines and their adhesiveness to un-etched human dentin. Dent. Mater. J. 1994, 13, 55-65.
    • (1994) Dent. Mater. J. , vol.13 , pp. 55-65
    • Tanaka, J.1    Suzuki, K.2    Nakai, H.3
  • 32
    • 0028892330 scopus 로고
    • Total syntheses of polyamine amides PhTX-4.3.3 and PhTX-3.4.3: Reductive alkylation is a rapid, practical route to philanthotoxins
    • Moya, E.; Blagbrough, I. S. Total syntheses of polyamine amides PhTX-4.3.3 and PhTX-3.4.3: reductive alkylation is a rapid, practical route to philanthotoxins. Tetrahedron Lett. 1995, 36, 9401-9404.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 9401-9404
    • Moya, E.1    Blagbrough, I.S.2
  • 34
    • 0029119899 scopus 로고
    • 2- and 4-nitrobenzene-sulfonamides: Exceptionally versatile means for preparation of secondary amines and protection of amines
    • Fukuyama, T.; Jow, C.-K.; Cheung, M. 2- and 4-nitrobenzene-sulfonamides: exceptionally versatile means for preparation of secondary amines and protection of amines. Tetrahedron Lett. 1995, 36, 6373-6374.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6373-6374
    • Fukuyama, T.1    Jow, C.-K.2    Cheung, M.3
  • 35
    • 0030936620 scopus 로고    scopus 로고
    • Site-selective N-methylation of peptides on solid support
    • Miller, S. C.; Scanlan, T. S. Site-selective N-methylation of peptides on solid support J. Am. Chem. Soc. 1997, 119, 2301-2302.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 2301-2302
    • Miller, S.C.1    Scanlan, T.S.2
  • 36
    • 33751183730 scopus 로고
    • Mild and selective palladium(0)-catalyzed deallylation of allylic amines. Allylamine and diallylamine as very convenient ammonia equivalents for the synthesis of primary amines
    • Garro-Helion, F.; Merzouk, A.; Guibe, F. Mild and Selective Palladium(0)-Catalyzed Deallylation of Allylic Amines. Allylamine and Diallylamine as Very Convenient Ammonia Equivalents for the Synthesis of Primary Amines. J. Org. Chem. 1993, 58, 6109-6113.
    • (1993) J. Org. Chem. , vol.58 , pp. 6109-6113
    • Garro-Helion, F.1    Merzouk, A.2    Guibe, F.3
  • 37
    • 0021164296 scopus 로고
    • Reagents for the stepwise functionalization of spermidine, homospermidine and bis(3-aminopropyl)amine
    • Bergeron, R. J.; Garlich, J. R.; Stolowich, N. J. Reagents for the stepwise functionalization of spermidine, homospermidine and bis(3-aminopropyl)amine. J. Org. Chem. 1984, 49, 2997-3001.
    • (1984) J. Org. Chem. , vol.49 , pp. 2997-3001
    • Bergeron, R.J.1    Garlich, J.R.2    Stolowich, N.J.3
  • 38
    • 33845280388 scopus 로고
    • Reagents for the stepwise functionalization of spermine
    • Bergeron, R. J.; McManis, J. S. Reagents for the stepwise functionalization of spermine. J. Org. Chem. 1988, 53, 3108-3111.
    • (1988) J. Org. Chem. , vol.53 , pp. 3108-3111
    • Bergeron, R.J.1    McManis, J.S.2
  • 39
    • 0142172992 scopus 로고
    • Ligand effects in enantioface differentiating 1,4-addition to 1,3-diphenyl-2-propen-1-one
    • Leyendecker, F.; Jesser, F.; Laucher, D. Ligand effects in enantioface differentiating 1,4-addition to 1,3-diphenyl-2-propen-1-one. Tetrahedron Lett. 1983, 24, 3513-3516.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 3513-3516
    • Leyendecker, F.1    Jesser, F.2    Laucher, D.3
  • 41
    • 37049158301 scopus 로고
    • The organic chemistry of phosphorus. Part. I. Some new methods for the preparation of alkyl halides
    • Landauer, S. R.; Rydon, H. N. The organic chemistry of phosphorus. Part. I. Some new methods for the preparation of alkyl halides. J. Chem. Soc. 1953, 2224-2234.
    • (1953) J. Chem. Soc. , pp. 2224-2234
    • Landauer, S.R.1    Rydon, H.N.2
  • 42
    • 0002779608 scopus 로고
    • Replacement of alcoholic hydroxy groups by halogens and other nucleophiles via oxyphosphonium intermediates
    • Castro, B. R. Replacement of alcoholic hydroxy groups by halogens and other nucleophiles via oxyphosphonium intermediates. Org. React. 1983, 29, 1-162.
    • (1983) Org. React. , vol.29 , pp. 1-162
    • Castro, B.R.1
  • 43
    • 0001813436 scopus 로고
    • Synthesis of primary amines via alkylation of the sodium salt of trifluoroacetamide: An alternative to the Gabriel synthesis
    • Harland, P. A.; Hodge, P.; Maughan, W.; Wildsmith, E. Synthesis of primary amines via alkylation of the sodium salt of trifluoroacetamide: an alternative to the Gabriel synthesis. Synthesis 1984, 940-943.
    • (1984) Synthesis , pp. 940-943
    • Harland, P.A.1    Hodge, P.2    Maughan, W.3    Wildsmith, E.4
  • 44
    • 0027536936 scopus 로고
    • Interaction of polyamines with neuronal ion channels
    • Scott, R. H.; Suton, K. G.; Dolphin, A. C. Interaction of polyamines with neuronal ion channels. Trends Neurosci. 1993, 16, 153-160.
    • (1993) Trends Neurosci. , vol.16 , pp. 153-160
    • Scott, R.H.1    Suton, K.G.2    Dolphin, A.C.3
  • 45
    • 0030899291 scopus 로고    scopus 로고
    • Modulation and block of ion channels: A new biology of polyamines
    • Williams, K. Modulation and block of ion channels: a new biology of polyamines. Cell Signal. 1997, 9, 1-13.
    • (1997) Cell Signal. , vol.9 , pp. 1-13
    • Williams, K.1
  • 46
    • 0032192053 scopus 로고    scopus 로고
    • The role of hydrophobic interactions in binding of polyamines to non NMDA receptor ion channels
    • Cu, C.; Bähring, R.; Mayer, M. L. The role of hydrophobic interactions in binding of polyamines to non NMDA receptor ion channels. Neuropharmacohgy 1998, 37, 1381-1391.
    • (1998) Neuropharmacohgy , vol.37 , pp. 1381-1391
    • Cu, C.1    Bähring, R.2    Mayer, M.L.3
  • 47
    • 0032159173 scopus 로고    scopus 로고
    • Potentiation and inhibition of nicotinic acetylcholine receptors by spermine in the TE671 human muscle cell line
    • Shao, Z.; Mellor, I. R.; Brierley, M. J.; Harris, J.; Usherwood, P. N. R. Potentiation and inhibition of nicotinic acetylcholine receptors by spermine in the TE671 human muscle cell line. J. Pharmacol. Exp. Ther. 1998, 286, 1269-1276.
    • (1998) J. Pharmacol. Exp. Ther. , vol.286 , pp. 1269-1276
    • Shao, Z.1    Mellor, I.R.2    Brierley, M.J.3    Harris, J.4    Usherwood, P.N.R.5
  • 51
    • 0023834181 scopus 로고
    • The human medulloblastoma cell line TE671 expresses a muscle like acetylcholine receptor - Cloning of the δ-subunit c-DNA
    • Shoepfer, R.; Luther, M.; Lindstrom, J. The human medulloblastoma cell line TE671 expresses a muscle like acetylcholine receptor - cloning of the δ-subunit c-DNA. FEBS Lett. 1988, 226, 235-240.
    • (1988) FEBS Lett. , vol.226 , pp. 235-240
    • Shoepfer, R.1    Luther, M.2    Lindstrom, J.3
  • 53
    • 84987071770 scopus 로고
    • Invertebrate pharmacological assay of novel, potent glutamate receptor antagonists: Acylated spermines
    • Blagbrough, I. S.; Bruce, M.; Bycroft, B. W.; Mather, A. J.; Usherwood, P. N. R. Invertebrate pharmacological assay of novel, potent glutamate receptor antagonists: acylated spermines. Pestic. Sci. 1990, 30, 387-403.
    • (1990) Pestic. Sci. , vol.30 , pp. 387-403
    • Blagbrough, I.S.1    Bruce, M.2    Bycroft, B.W.3    Mather, A.J.4    Usherwood, P.N.R.5
  • 54
    • 0026592727 scopus 로고
    • Philanthotoxins block glutamaterigc transmission in rat hippocampus. II. Inhibition of synaptic transmission in the CA1 region
    • Schluter, N. C. M.; Piek, T.; Da Silva, F. H. L.; Philanthotoxins block glutamaterigc transmission in rat hippocampus. II. Inhibition of synaptic transmission in the CA1 region. Comp. Biochem. Physiol. 1992, 101C, 41-47.
    • (1992) Comp. Biochem. Physiol. , vol.101 C , pp. 41-47
    • Schluter, N.C.M.1    Piek, T.2    Da Silva, F.H.L.3
  • 56
    • 0031935687 scopus 로고    scopus 로고
    • Design, synthesis and biological evaluation of spider toxins (Argiotoxin-636) analogues as NMDA receptor antagonists
    • Moe, S. T.; Smith, D. L.; Chien, Y.; Raszkiewicz, J. L.; Artman, L. D.; Mueller, A. L. Design, synthesis and biological evaluation of spider toxins (Argiotoxin-636) analogues as NMDA receptor antagonists. Pharm. Res. 1998, 15, 31-38.
    • (1998) Pharm. Res. , vol.15 , pp. 31-38
    • Moe, S.T.1    Smith, D.L.2    Chien, Y.3    Raszkiewicz, J.L.4    Artman, L.D.5    Mueller, A.L.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.