메뉴 건너뛰기




Volumn 51, Issue 5, 2008, Pages 1369-1376

A structure-activity relationship study and combinatorial synthetic approach of C-terminal modified bifunctional peptides that are δ/μ opioid receptor agonists and neurokinin 1 receptor antagonists

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL AMIDE DERIVATIVE; BIPHALIN; CARBOXYL GROUP; DELTA OPIATE RECEPTOR AGONIST; ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; ENKEPHALIN[2,5 DEXTRO PENICILLAMINE]; N ACETYLTRYPTOPHAN 3,5 BIS(TRIFLUOROMETHYL)BENZYL ESTER; NEUROKININ 1 RECEPTOR ANTAGONIST; PEPTIDE; PEPTIDE DERIVATIVE; SUBSTANCE P; UNCLASSIFIED DRUG;

EID: 41649107460     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070332f     Document Type: Article
Times cited : (43)

References (49)
  • 1
    • 0019775230 scopus 로고
    • Spinal opiate analgesia: Characteristics and principles of action
    • Yaksh, T. L. Spinal opiate analgesia: characteristics and principles of action. Pain 1981, 11, 293-346.
    • (1981) Pain , vol.11 , pp. 293-346
    • Yaksh, T.L.1
  • 2
    • 20344362179 scopus 로고    scopus 로고
    • Underlying mechanisms of pronociceptive consequences of prolonged morphine exposure
    • Ossipov, M. H.; Lai, J.; King, T.; Vanderah, T. W.; Porreca, F. Underlying mechanisms of pronociceptive consequences of prolonged morphine exposure. Biopolymers 2005, 80, 319-324.
    • (2005) Biopolymers , vol.80 , pp. 319-324
    • Ossipov, M.H.1    Lai, J.2    King, T.3    Vanderah, T.W.4    Porreca, F.5
  • 3
    • 14644439235 scopus 로고    scopus 로고
    • Improving opioid effectiveness: From ideas to evidence
    • Kalso, E. Improving opioid effectiveness: from ideas to evidence. Eur. J. Pain 2005, 9, 131-135.
    • (2005) Eur. J. Pain , vol.9 , pp. 131-135
    • Kalso, E.1
  • 5
    • 26244461682 scopus 로고    scopus 로고
    • Is paradoxical pain induced by sustained opioid exposure an underlying mechanism of opioid antinociceptive tolerance?
    • King, T.; Ossipov, M. H.; Vanderah, T. W.; Porreca, F.; Lai, J. Is paradoxical pain induced by sustained opioid exposure an underlying mechanism of opioid antinociceptive tolerance? Neurosignals 2005, 14, 194-205.
    • (2005) Neurosignals , vol.14 , pp. 194-205
    • King, T.1    Ossipov, M.H.2    Vanderah, T.W.3    Porreca, F.4    Lai, J.5
  • 7
    • 26244461682 scopus 로고    scopus 로고
    • Is paradoxical pain induced by sustained opioid exposure an underlying mechanism of opioid antinociceptive tolerance
    • King, T.; Ossipov, M. H.; Vanderah, T. W.; Porreca, F.; Lai, J. Is paradoxical pain induced by sustained opioid exposure an underlying mechanism of opioid antinociceptive tolerance. Neurosignals 2005, 14 (4), 194-205.
    • (2005) Neurosignals , vol.14 , Issue.4 , pp. 194-205
    • King, T.1    Ossipov, M.H.2    Vanderah, T.W.3    Porreca, F.4    Lai, J.5
  • 8
    • 0034675028 scopus 로고    scopus 로고
    • Morphine treatment induced calcitonin gene-related peptide and substance P increases in cultured dorsal root ganglion neurons
    • Ma, W.; Zheng, W. H.; Kar, S; Quirion, R. Morphine treatment induced calcitonin gene-related peptide and substance P increases in cultured dorsal root ganglion neurons. Neuroscience 2000, 99 (3), 529-539.
    • (2000) Neuroscience , vol.99 , Issue.3 , pp. 529-539
    • Ma, W.1    Zheng, W.H.2    Kar, S.3    Quirion, R.4
  • 9
    • 0141705322 scopus 로고    scopus 로고
    • Inhibition of neurokinin-1 - substance P receptor and prostanoid activity prevents and reverses the development of morphine tolerance in vivo and the morphine-induced increase in CGRP expression in cultured dorsal root ganglion neurons
    • Powell, K. J.; Quirion, R.; Jhamandas, K. Inhibition of neurokinin-1 - substance P receptor and prostanoid activity prevents and reverses the development of morphine tolerance in vivo and the morphine-induced increase in CGRP expression in cultured dorsal root ganglion neurons. Eur. J. Neurosci. 2003, 18 (6), 1572-1583.
    • (2003) Eur. J. Neurosci , vol.18 , Issue.6 , pp. 1572-1583
    • Powell, K.J.1    Quirion, R.2    Jhamandas, K.3
  • 10
    • 0028255873 scopus 로고
    • Spinal co-administration of peptide substance P antagonist increases antinociceptive effect of the opioid peptide biphalin
    • Misterek, K.; Maszczynska, I.; Dorociak, A.; Gumulka, S. W.; Carr, D. B.; Szyfelbein, S. K.; Lipkowski, A. W. Spinal co-administration of peptide substance P antagonist increases antinociceptive effect of the opioid peptide biphalin. Life Sci. 1994, 54 (14), 939-944.
    • (1994) Life Sci , vol.54 , Issue.14 , pp. 939-944
    • Misterek, K.1    Maszczynska, I.2    Dorociak, A.3    Gumulka, S.W.4    Carr, D.B.5    Szyfelbein, S.K.6    Lipkowski, A.W.7
  • 11
    • 23944462196 scopus 로고    scopus 로고
    • Resting and evoked spinal substance P release during chronic intrathecal morphine infusion: Parallels with tolerance and dependence
    • Gu, G.; Kondo, I.; Hua, X. Y.; Yaksh, T. L. Resting and evoked spinal substance P release during chronic intrathecal morphine infusion: parallels with tolerance and dependence. J. Pharmacol. Exp. Ther. 2005, 3/4 (3), 1362-1369.
    • (2005) J. Pharmacol. Exp. Ther , vol.3-4 , Issue.3 , pp. 1362-1369
    • Gu, G.1    Kondo, I.2    Hua, X.Y.3    Yaksh, T.L.4
  • 12
    • 0016757754 scopus 로고
    • Substance P: Localization in the central nervous system and in some primary sensory neurons
    • Hökfelt, T.; Kellerth, J.; Nilsson, G.; Pernow, B. Substance P: localization in the central nervous system and in some primary sensory neurons. Science, 1975, 190, 889-890.
    • (1975) Science , vol.190 , pp. 889-890
    • Hökfelt, T.1    Kellerth, J.2    Nilsson, G.3    Pernow, B.4
  • 13
    • 12944335078 scopus 로고
    • The glycine-extended SP precursor, SP-G, is normally expressed in SP-containing neurons
    • Leeman S. E, Krause J. E, Lembeck, F. eds, New York Academy of Sciences: New York
    • Marchand, J. E.; Kream, R. M. The glycine-extended SP precursor, SP-G, is normally expressed in SP-containing neurons, in Substance P and Related Peptides: Cellular and Molecular Physiology. Leeman S. E., Krause J. E., Lembeck, F. eds.; New York Academy of Sciences: New York, 1990.
    • (1990) Substance P and Related Peptides: Cellular and Molecular Physiology
    • Marchand, J.E.1    Kream, R.M.2
  • 14
    • 0034009505 scopus 로고    scopus 로고
    • Dual Ultrastructural Localization of μ-Opiate Receptors and Substance P in the Dorsal Horn
    • Aicher, S. A.; Sharma, S.; Cheng, P. Y.; Chen, L. Y. L.; Pickel, V. M. Dual Ultrastructural Localization of μ-Opiate Receptors and Substance P in the Dorsal Horn. Synapse 2000, 36, 12-20.
    • (2000) Synapse , vol.36 , pp. 12-20
    • Aicher, S.A.1    Sharma, S.2    Cheng, P.Y.3    Chen, L.Y.L.4    Pickel, V.M.5
  • 16
    • 41649111167 scopus 로고    scopus 로고
    • Yamamoto, T.; Nair, P.; Davis, P.; Ma, S. W.; Moye, S.; Largent, T.; Vanderah, T. W.; Lai, J.; Porreca, F.; Yamamura, H. I.; Hruby, V. J. Design, Structure-Activity Relationships and Biological Evaluation of Novel Bifunctional C-terminal Modified Peptides for δ/μ Opioid Receptor Agonists and Neurokinin-1 Receptor Antagonists. 232nd ACS National Meeting, San Francisco, CA, United States, Sep. 10-14, 2006; p MEDI-7. The in vivo result presented at the conference is also available in the Supporting Information.
    • Yamamoto, T.; Nair, P.; Davis, P.; Ma, S. W.; Moye, S.; Largent, T.; Vanderah, T. W.; Lai, J.; Porreca, F.; Yamamura, H. I.; Hruby, V. J. Design, Structure-Activity Relationships and Biological Evaluation of Novel Bifunctional C-terminal Modified Peptides for δ/μ Opioid Receptor Agonists and Neurokinin-1 Receptor Antagonists. 232nd ACS National Meeting, San Francisco, CA, United States, Sep. 10-14, 2006; p MEDI-7. The in vivo result presented at the conference is also available in the Supporting Information.
  • 18
    • 1642398888 scopus 로고    scopus 로고
    • Spinal antinociceptive effects of AA501, a novel chimeric peptide with opioid receptor agonist and tachykinin receptor antagonist moieties
    • Bonney, I. M.; Foran, S. E.; Marchand, J. E.; Lipkowski, A. W.; Carr, D. B. Spinal antinociceptive effects of AA501, a novel chimeric peptide with opioid receptor agonist and tachykinin receptor antagonist moieties. Eur. J. Pharmacol. 2004, 488 (1-3), 91-99.
    • (2004) Eur. J. Pharmacol , vol.488 , Issue.1-3 , pp. 91-99
    • Bonney, I.M.1    Foran, S.E.2    Marchand, J.E.3    Lipkowski, A.W.4    Carr, D.B.5
  • 19
    • 27144449695 scopus 로고    scopus 로고
    • Designed multiple ligands. An emerging drug discovery paradigm
    • Morphy, R.; Rankovic, Z. Designed multiple ligands. An emerging drug discovery paradigm. J. Med. Chem. 2005, 48 (21), 6523-6543.
    • (2005) J. Med. Chem , vol.48 , Issue.21 , pp. 6523-6543
    • Morphy, R.1    Rankovic, Z.2
  • 20
    • 33644863475 scopus 로고    scopus 로고
    • Design and synthesis of novel hydrazide-linked bifunctional peptides as delta/mu opioid receptor agonists and CCK-1/CCK-2 receptor antagonists
    • Lee, Y. S.; Agnes, R. S.; Badghisi, H.; Davis, P.; Ma, S. W.; Lai, J.; Porreca, F.; Hruby, V. J. Design and synthesis of novel hydrazide-linked bifunctional peptides as delta/mu opioid receptor agonists and CCK-1/CCK-2 receptor antagonists. J. Med. Chem. 2006, 49 (5), 1773-1780.
    • (2006) J. Med. Chem , vol.49 , Issue.5 , pp. 1773-1780
    • Lee, Y.S.1    Agnes, R.S.2    Badghisi, H.3    Davis, P.4    Ma, S.W.5    Lai, J.6    Porreca, F.7    Hruby, V.J.8
  • 21
    • 33646722004 scopus 로고    scopus 로고
    • Structure-activity relationships of bifunctional peptides based on overlapping pharmacophores at opioid and cholecystokinin receptors
    • Agnes, R. S.; Lee, Y. S.; Davis, P.; Ma, S. W.; Badghisi, H.; Porreca, F.; Lai, J.; Hruby, V. J. Structure-activity relationships of bifunctional peptides based on overlapping pharmacophores at opioid and cholecystokinin receptors. J. Med. Chem. 2006, 49 (10), 2868-2875.
    • (2006) J. Med. Chem , vol.49 , Issue.10 , pp. 2868-2875
    • Agnes, R.S.1    Lee, Y.S.2    Davis, P.3    Ma, S.W.4    Badghisi, H.5    Porreca, F.6    Lai, J.7    Hruby, V.J.8
  • 22
    • 0037498433 scopus 로고    scopus 로고
    • Design of novel peptide ligands which have opioid agonist activity and CCK antagonist activity for the treatment of pain
    • Hruby, V. J.; Agnes, R. S.; Davis, P.; Ma, S. W.; Lee, Y. S.; Vanderah, T.W.; Lai, J.; Porreca, F. Design of novel peptide ligands which have opioid agonist activity and CCK antagonist activity for the treatment of pain. Life Sci. 2003, 73 (6), 699-704.
    • (2003) Life Sci , vol.73 , Issue.6 , pp. 699-704
    • Hruby, V.J.1    Agnes, R.S.2    Davis, P.3    Ma, S.W.4    Lee, Y.S.5    Vanderah, T.W.6    Lai, J.7    Porreca, F.8
  • 24
    • 2142658722 scopus 로고    scopus 로고
    • New Torends in the Development of Opioid Peptide Analogues as Advanced Remedies for pain Relief
    • Gentilucci, L. New Torends in the Development of Opioid Peptide Analogues as Advanced Remedies for pain Relief. Curr. Top. Med. Chem. 2004, 4, 19-38.
    • (2004) Curr. Top. Med. Chem , vol.4 , pp. 19-38
    • Gentilucci, L.1
  • 29
    • 9344228432 scopus 로고    scopus 로고
    • General Inverse Solid Phase Synthesis Method for C-Terminally Modified Peptide Mimetics
    • Sasubilli, R.; Gutheil, W. General Inverse Solid Phase Synthesis Method for C-Terminally Modified Peptide Mimetics. J. Comb. Chem. 2004, 6, 911-915.
    • (2004) J. Comb. Chem , vol.6 , pp. 911-915
    • Sasubilli, R.1    Gutheil, W.2
  • 30
    • 0141670577 scopus 로고    scopus 로고
    • Solid-phase synthesis of C-terminal modified peptides
    • Aisina, J.; Albercio, F. Solid-phase synthesis of C-terminal modified peptides. Biopolymres 2003, 71, 454-477.
    • (2003) Biopolymres , vol.71 , pp. 454-477
    • Aisina, J.1    Albercio, F.2
  • 33
    • 0032587925 scopus 로고    scopus 로고
    • The tachykinin NK1 receptor in the brain: Pharmacology and putative functions
    • and references therein
    • Saria, A. The tachykinin NK1 receptor in the brain: pharmacology and putative functions. Eur. J. Pharmacol. 1999, 375 (1-3), 5160. and references therein.
    • (1999) Eur. J. Pharmacol , vol.375 , Issue.1-3 , pp. 5160
    • Saria, A.1
  • 34
    • 20344398411 scopus 로고    scopus 로고
    • The effects of haloperidol treatment on the distribution of NK1 receptor immunoreactive neurons in guinea-pig brain
    • Tooneya, P. A.; Andersona, W. B.; Lynch-Frameb, A.; Chahla, L. A. The effects of haloperidol treatment on the distribution of NK1 receptor immunoreactive neurons in guinea-pig brain. Neurosci. Lett. 2005, 383 (1-2), 155-159.
    • (2005) Neurosci. Lett , vol.383 , Issue.1-2 , pp. 155-159
    • Tooneya, P.A.1    Andersona, W.B.2    Lynch-Frameb, A.3    Chahla, L.A.4
  • 35
    • 0031836220 scopus 로고    scopus 로고
    • Involvement of the central tachykinin NK1 receptor during maintenance of mechanical hypersensitivity induced by diabetes in the rat
    • Field, M. J.; McCleary, S.; Boden, P.; Suman-Chauhan, N.; Hughes, J.; Singh, L. Involvement of the central tachykinin NK1 receptor during maintenance of mechanical hypersensitivity induced by diabetes in the rat. J. Pharmacol. Exp. Ther. 1998, 285 (3), 1226-1232.
    • (1998) J. Pharmacol. Exp. Ther , vol.285 , Issue.3 , pp. 1226-1232
    • Field, M.J.1    McCleary, S.2    Boden, P.3    Suman-Chauhan, N.4    Hughes, J.5    Singh, L.6
  • 36
    • 0027464327 scopus 로고
    • Non-peptide antagonists, CP-96,345 and RP 67580, distinguish species variants in tachykinin NK1 receptors
    • Barr, A. J.; Watson, S. P. Non-peptide antagonists, CP-96,345 and RP 67580, distinguish species variants in tachykinin NK1 receptors. Br. J. Pharmacol. 1993, 108 (1), 223-227.
    • (1993) Br. J. Pharmacol , vol.108 , Issue.1 , pp. 223-227
    • Barr, A.J.1    Watson, S.P.2
  • 38
    • 0344448273 scopus 로고
    • Coherence transfer by isotropic mixing: Application to proton correlation spectroscopy
    • Braunschweiler, L.; Ernst, R. R. Coherence transfer by isotropic mixing: Application to proton correlation spectroscopy. J. Magn. Reson. 1983, 53, 521-528.
    • (1983) J. Magn. Reson , vol.53 , pp. 521-528
    • Braunschweiler, L.1    Ernst, R.R.2
  • 39
    • 33845378943 scopus 로고
    • Assignment of complex 1H-NMR spectra via two-dimensional homonuclear Hartmann-Hahn spectroscopy
    • Davis, D. G.; Bax, A. Assignment of complex 1H-NMR spectra via two-dimensional homonuclear Hartmann-Hahn spectroscopy. J. Am. Chem. Soc. 1985, 107, 2820-2821.
    • (1985) J. Am. Chem. Soc , vol.107 , pp. 2820-2821
    • Davis, D.G.1    Bax, A.2
  • 40
    • 45949124222 scopus 로고
    • Generation of pure phase NMR subspectra for measurement of homonuclear coupling constants
    • Subramanian, S.; Bax, A. Generation of pure phase NMR subspectra for measurement of homonuclear coupling constants. J. Magn. Reson. 1987, 71, 325-330.
    • (1987) J. Magn. Reson , vol.71 , pp. 325-330
    • Subramanian, S.1    Bax, A.2
  • 41
    • 45949117739 scopus 로고
    • Improved techniques for homonuclear rotating-frame and isotropic mixing experiments
    • Ranee, M. Improved techniques for homonuclear rotating-frame and isotropic mixing experiments. J. Magn. Reson. 1987, 74, 557-564.
    • (1987) J. Magn. Reson , vol.74 , pp. 557-564
    • Ranee, M.1
  • 42
    • 5144233105 scopus 로고
    • MLEV-17-based two-dimensional homonuclear magnetization transfer spectroscopy
    • Bax, A.; Davis, D. G. MLEV-17-based two-dimensional homonuclear magnetization transfer spectroscopy. J. Magn. Reson. 1985, 65, 355-360.
    • (1985) J. Magn. Reson , vol.65 , pp. 355-360
    • Bax, A.1    Davis, D.G.2
  • 43
    • 0021114895 scopus 로고
    • Application of phase sensitive two-dimensional correlated spectroscopy (COSY) for measurements of 1H-1H spin-spin coupling constants in proteins
    • Marion, D.; Wüthrich, K. Application of phase sensitive two-dimensional correlated spectroscopy (COSY) for measurements of 1H-1H spin-spin coupling constants in proteins. Biochem. Biophys. Res. Commun. 1983, 113, 967-974.
    • (1983) Biochem. Biophys. Res. Commun , vol.113 , pp. 967-974
    • Marion, D.1    Wüthrich, K.2
  • 44
    • 0344448273 scopus 로고
    • Coherence transfer by isotropic mixing: Application to proton correlation spectroscopy
    • Braunschweiler, L.; Ernst, R. R. Coherence transfer by isotropic mixing: Application to proton correlation spectroscopy. J. Magn. Reson. 1983, 53, 521-528.
    • (1983) J. Magn. Reson , vol.53 , pp. 521-528
    • Braunschweiler, L.1    Ernst, R.R.2
  • 45
    • 0030069077 scopus 로고    scopus 로고
    • The peptide binding site of the substance P (NK-1) receptor localized by a photoreactive analogue of substance P: Presence of a disulfide bond
    • Boyd, N. D.; Kage, R.; Dumas, J. J.; Krause, J. E.; Leeman, S. E. The peptide binding site of the substance P (NK-1) receptor localized by a photoreactive analogue of substance P: presence of a disulfide bond. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 433-437.
    • (1996) Proc. Natl. Acad. Sci. U.S.A , vol.93 , pp. 433-437
    • Boyd, N.D.1    Kage, R.2    Dumas, J.J.3    Krause, J.E.4    Leeman, S.E.5
  • 47
    • 0020608003 scopus 로고
    • Affinity of normorphine for its pharmacologic receptor in the naive and morphine-tolerant guinea-pig isolated ileum
    • Porreca, F.; Burks, T. F. Affinity of normorphine for its pharmacologic receptor in the naive and morphine-tolerant guinea-pig isolated ileum. J. Pharmacol. Exp. Ther 1983, 225 (3), 688-693.
    • (1983) J. Pharmacol. Exp. Ther , vol.225 , Issue.3 , pp. 688-693
    • Porreca, F.1    Burks, T.F.2
  • 48
    • 0025344555 scopus 로고
    • Opioid agonist affinity in the guinea-pig ileum and mouse vas deferens
    • Porreca, F.; LoPresti, D.; Ward, S. J. Opioid agonist affinity in the guinea-pig ileum and mouse vas deferens. Eur. J. Pharmacol. 1990, 179 (1-2), 129-139.
    • (1990) Eur. J. Pharmacol , vol.179 , Issue.1-2 , pp. 129-139
    • Porreca, F.1    LoPresti, D.2    Ward, S.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.