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Volumn 29, Issue 8, 2008, Pages 1413-1423

Structure-activity relationships of bifunctional cyclic disulfide peptides based on overlapping pharmacophores at opioid and cholecystokinin receptors

Author keywords

Bifunctional peptides; G Protein coupled receptors; Multivalent ligands; NMR conformation; Overlapping pharmacophores; Pain; Tolerance

Indexed keywords

CHOLECYSTOKININ A RECEPTOR; CHOLECYSTOKININ B RECEPTOR; CHOLECYSTOKININ RECEPTOR; CYCLOPEPTIDE; DELTA OPIATE RECEPTOR; MU OPIATE RECEPTOR; RECEPTOR BLOCKING AGENT;

EID: 47649130291     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.peptides.2008.03.022     Document Type: Article
Times cited : (20)

References (51)
  • 1
    • 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., et al. Structure-activity relationships of bifunctional peptides based on overlapping pharmacophores at opioid and cholecystokinin receptors. J Med Chem 49 (2006) 2868-2875
    • (2006) J Med Chem , vol.49 , pp. 2868-2875
    • Agnes, R.S.1    Lee, Y.S.2    Davis, P.3    Ma, S.-W.4    Badghisi, H.5    Porreca, F.6
  • 3
    • 0037075065 scopus 로고    scopus 로고
    • Environmental mimic of receptor interaction: conformational analysis of CCK-15 in solution
    • Albrizio S., Carotenuto A., Fattorusso C., Moroder L., Picone D., Temussi P.A., et al. Environmental mimic of receptor interaction: conformational analysis of CCK-15 in solution. J Med Chem 45 (2002) 762-769
    • (2002) J Med Chem , vol.45 , pp. 762-769
    • Albrizio, S.1    Carotenuto, A.2    Fattorusso, C.3    Moroder, L.4    Picone, D.5    Temussi, P.A.6
  • 4
    • 0036830576 scopus 로고    scopus 로고
    • Practical protocols for stepwise solid-phase synthesis of cysteine-containing peptides
    • Angell Y.M., Alsina J., Albericio F., and Barany G. Practical protocols for stepwise solid-phase synthesis of cysteine-containing peptides. J Pept Res 60 (2002) 292-299
    • (2002) J Pept Res , vol.60 , pp. 292-299
    • Angell, Y.M.1    Alsina, J.2    Albericio, F.3    Barany, G.4
  • 5
    • 0032934351 scopus 로고    scopus 로고
    • Cyclic enkephalin analogs that are hybrids of DPDPE-related peptides and metenkephalin-Arg-Gly-Leu: prohormone analogs that retain good potency and selectivity for delta opioid receptors
    • Bartosz-Bechowski H., Davis P., Slaninova J., Malatynska E., Stropova D., Porreca F., et al. Cyclic enkephalin analogs that are hybrids of DPDPE-related peptides and metenkephalin-Arg-Gly-Leu: prohormone analogs that retain good potency and selectivity for delta opioid receptors. J Pept Res 53 (1999) 329-336
    • (1999) J Pept Res , vol.53 , pp. 329-336
    • Bartosz-Bechowski, H.1    Davis, P.2    Slaninova, J.3    Malatynska, E.4    Stropova, D.5    Porreca, F.6
  • 6
    • 5144233105 scopus 로고
    • MLEV-17-based two-dimensional homonuclear magnetization transfer spectroscopy
    • Bax A., and Davis D.G. MLEV-17-based two-dimensional homonuclear magnetization transfer spectroscopy. J Magn Reson 65 (1985) 355-360
    • (1985) J Magn Reson , vol.65 , pp. 355-360
    • Bax, A.1    Davis, D.G.2
  • 9
    • 0024345741 scopus 로고
    • Synthesis and binding affinities of cyclic and related linear analogs of CCK8 selective for central receptors
    • Charpentier B., Dor A., Roy P., England P., Pham H., Durieux C., et al. Synthesis and binding affinities of cyclic and related linear analogs of CCK8 selective for central receptors. J Med Chem 32 (1989) 1184-1190
    • (1989) J Med Chem , vol.32 , pp. 1184-1190
    • Charpentier, B.1    Dor, A.2    Roy, P.3    England, P.4    Pham, H.5    Durieux, C.6
  • 13
    • 0020170261 scopus 로고
    • Component vicinal coupling constants for calculating side-chain conformations in amino acids
    • De Leeuw F.A., and Altona C. Component vicinal coupling constants for calculating side-chain conformations in amino acids. Int J Pept Protein Res 20 (1982) 120-125
    • (1982) Int J Pept Protein Res , vol.20 , pp. 120-125
    • De Leeuw, F.A.1    Altona, C.2
  • 14
    • 0020681585 scopus 로고
    • Evidence for the neuropeptide cholecystokinin as an antagonist of opiate analgesia
    • Faris P.L., Komisaruk B.R., Watkins L.R., and Mayer D.J. Evidence for the neuropeptide cholecystokinin as an antagonist of opiate analgesia. Science 219 (1983) 310-312
    • (1983) Science , vol.219 , pp. 310-312
    • Faris, P.L.1    Komisaruk, B.R.2    Watkins, L.R.3    Mayer, D.J.4
  • 16
    • 12644261424 scopus 로고    scopus 로고
    • Enkephalin analog prodrugs: assessment of in vitro conversion, enzyme cleavage characterization and blood-brain barrier permeability
    • Greene D.L., Hau V.S., Abbruscato T.J., Bartosz H., Misicka A., Lipkowski A.W., et al. Enkephalin analog prodrugs: assessment of in vitro conversion, enzyme cleavage characterization and blood-brain barrier permeability. J Pharmacol Exp Therap 277 (1996) 1366-1375
    • (1996) J Pharmacol Exp Therap , vol.277 , pp. 1366-1375
    • Greene, D.L.1    Hau, V.S.2    Abbruscato, T.J.3    Bartosz, H.4    Misicka, A.5    Lipkowski, A.W.6
  • 17
    • 4444328321 scopus 로고    scopus 로고
    • Neural basis for the hyperalgesic action of cholecystokinin in the rostral ventromedial medulla
    • Heinricher M.M., and Neubert M.J. Neural basis for the hyperalgesic action of cholecystokinin in the rostral ventromedial medulla. J Neurophysiol 92 (2004) 1982-1989
    • (2004) J Neurophysiol , vol.92 , pp. 1982-1989
    • Heinricher, M.M.1    Neubert, M.J.2
  • 18
    • 0033495881 scopus 로고    scopus 로고
    • Conformation-activity relationships of opioid peptides with selective activities at opioid receptors
    • Hruby V.J., and Agnes R.S. Conformation-activity relationships of opioid peptides with selective activities at opioid receptors. Biopolymers 51 (1999) 391-410
    • (1999) Biopolymers , vol.51 , pp. 391-410
    • Hruby, V.J.1    Agnes, R.S.2
  • 19
    • 0030773558 scopus 로고    scopus 로고
    • Cyclic enkephalin analogues with exceptional potency and selectivity for delta-opioid receptors
    • Hruby V.J., Bartosz-Bechowski H., Davis P., Slaninova J., Zalewska T., Stropova D., et al. Cyclic enkephalin analogues with exceptional potency and selectivity for delta-opioid receptors. J Med Chem 40 (1997) 3957-3962
    • (1997) J Med Chem , vol.40 , pp. 3957-3962
    • Hruby, V.J.1    Bartosz-Bechowski, H.2    Davis, P.3    Slaninova, J.4    Zalewska, T.5    Stropova, D.6
  • 21
    • 0023883819 scopus 로고
    • The conformational properties of the delta opioid peptide cyclic [d-Pen2,d-Pen5]enkephalin in aqueous solution determined by NMR and energy minimization calculations
    • Hruby V.J., Kao L.-F., Pettitt M.B., and Karplus M. The conformational properties of the delta opioid peptide cyclic [d-Pen2,d-Pen5]enkephalin in aqueous solution determined by NMR and energy minimization calculations. J Am Chem Soc (1988) 3351-3359
    • (1988) J Am Chem Soc , pp. 3351-3359
    • Hruby, V.J.1    Kao, L.-F.2    Pettitt, M.B.3    Karplus, M.4
  • 23
    • 0343359244 scopus 로고
    • Investigation of exchange processes by two-dimensional NMR spectroscopy
    • Jeener J., Meyer B.H., Bachman P., and Ernst R.R. Investigation of exchange processes by two-dimensional NMR spectroscopy. J Chem Phys 71 (1979) 4546-4553
    • (1979) J Chem Phys , vol.71 , pp. 4546-4553
    • Jeener, J.1    Meyer, B.H.2    Bachman, P.3    Ernst, R.R.4
  • 24
    • 0001112916 scopus 로고
    • 13C-NMR chemical shifts with the side-chain stereochemistry of these amino acid residues
    • 13C-NMR chemical shifts with the side-chain stereochemistry of these amino acid residues. J Org Chem 59 (1994) 991-998
    • (1994) J Org Chem , vol.59 , pp. 991-998
    • Kövér, K.E.1    Jiao, D.2    Fang, S.3    Hruby, V.J.4
  • 25
    • 0001534216 scopus 로고
    • Conformational analysis of four beta-methlphenylalanine stereoisomers in a bioactive peptide by z-filtered relay NMR spectroscopy
    • Kövér K.E., Jiao D., Fang S., and Hruby V.J. Conformational analysis of four beta-methlphenylalanine stereoisomers in a bioactive peptide by z-filtered relay NMR spectroscopy. Mag Reson Chem 31 (1993) 1072-1076
    • (1993) Mag Reson Chem , vol.31 , pp. 1072-1076
    • Kövér, K.E.1    Jiao, D.2    Fang, S.3    Hruby, V.J.4
  • 26
    • 0025117443 scopus 로고
    • Enkephalin analogs containing beta-naphthylalanine at the fourth position
    • Mierke D.F., Said-Nejad O.E., Schiller P.W., and Goodman M. Enkephalin analogs containing beta-naphthylalanine at the fourth position. Biopolymers 29 (1990) 179-196
    • (1990) Biopolymers , vol.29 , pp. 179-196
    • Mierke, D.F.1    Said-Nejad, O.E.2    Schiller, P.W.3    Goodman, M.4
  • 27
    • 0013579630 scopus 로고
    • Optimization of disulfide bond formation
    • Misicka A., and Hruby V.J. Optimization of disulfide bond formation. Pol J Chem 68 (1994) 893-899
    • (1994) Pol J Chem , vol.68 , pp. 893-899
    • Misicka, A.1    Hruby, V.J.2
  • 29
    • 0020628905 scopus 로고
    • Conformationally constrained cyclic enkephalin analogs with pronounced delta opioid receptor agonist selectivity
    • Mosberg H.I., Hurst R., Hruby V.J., Galligan J.J., Burks T.F., Gee K., et al. Conformationally constrained cyclic enkephalin analogs with pronounced delta opioid receptor agonist selectivity. Life Sci 32 (1983) 2565-2569
    • (1983) Life Sci , vol.32 , pp. 2565-2569
    • Mosberg, H.I.1    Hurst, R.2    Hruby, V.J.3    Galligan, J.J.4    Burks, T.F.5    Gee, K.6
  • 30
    • 0000440578 scopus 로고
    • Bis-penicillamine enkephalins possess highly improved specificity toward delta opioid receptors
    • Mosberg H.I., Hurst R., Hruby V.J., Gee K., Yamamura H.I., Galligan J.J., et al. Bis-penicillamine enkephalins possess highly improved specificity toward delta opioid receptors. Proc Natl Acad Sci USA 80 (1983) 5871-5874
    • (1983) Proc Natl Acad Sci USA , vol.80 , pp. 5871-5874
    • Mosberg, H.I.1    Hurst, R.2    Hruby, V.J.3    Gee, K.4    Yamamura, H.I.5    Galligan, J.J.6
  • 31
    • 0021287878 scopus 로고
    • 1H NMR investigation of conformational features of cyclic enkephalinamide analogs
    • 1H NMR investigation of conformational features of cyclic enkephalinamide analogs. Int J Pept Protein Res 23 (1984) 462-466
    • (1984) Int J Pept Protein Res , vol.23 , pp. 462-466
    • Mosberg, H.I.1    Schiller, P.W.2
  • 33
    • 0027294038 scopus 로고
    • Models for the A- and B-receptor-bound conformations of CCK-8
    • Nikiforovich G.V., and Hruby V.J. Models for the A- and B-receptor-bound conformations of CCK-8. Biochem Biophys Res Commun 194 (1993) 9-16
    • (1993) Biochem Biophys Res Commun , vol.194 , pp. 9-16
    • Nikiforovich, G.V.1    Hruby, V.J.2
  • 34
    • 0032919177 scopus 로고    scopus 로고
    • CCK-B receptor: chemistry, molecular biology, biochemistry and pharmacology
    • Noble F., and Roques B.P. CCK-B receptor: chemistry, molecular biology, biochemistry and pharmacology. Prog Neurobiol 58 (1999) 349-379
    • (1999) Prog Neurobiol , vol.58 , pp. 349-379
    • Noble, F.1    Roques, B.P.2
  • 35
    • 0032708056 scopus 로고    scopus 로고
    • International union of pharmacology. XXI: Structure, distribution, and functions of cholecystokinin receptors
    • Noble F., Wank S.A., Crawley J.N., Bradwejn J., Seroogy K.B., Hamon M., et al. International union of pharmacology. XXI: Structure, distribution, and functions of cholecystokinin receptors. Pharmacol Rev 51 (1999) 745-781
    • (1999) Pharmacol Rev , vol.51 , pp. 745-781
    • Noble, F.1    Wank, S.A.2    Crawley, J.N.3    Bradwejn, J.4    Seroogy, K.B.5    Hamon, M.6
  • 36
    • 25844510218 scopus 로고    scopus 로고
    • Challenges in the development of novel treatment strategies for neuropathic pain
    • Ossipov M.H., and Porreca F. Challenges in the development of novel treatment strategies for neuropathic pain. NeuroRx 2 (2005) 650-661
    • (2005) NeuroRx , vol.2 , pp. 650-661
    • Ossipov, M.H.1    Porreca, F.2
  • 37
    • 49749206569 scopus 로고
    • Nuclear magnetic resonance (NMR) study of some a-amino acids. I: Coupling constants in alkaline and acidic medium
    • Pachler K.G.R. Nuclear magnetic resonance (NMR) study of some a-amino acids. I: Coupling constants in alkaline and acidic medium. Spectrochim Acta 19 (1963) 2085-2092
    • (1963) Spectrochim Acta , vol.19 , pp. 2085-2092
    • Pachler, K.G.R.1
  • 38
    • 4243567363 scopus 로고
    • Nuclear magnetic resonance study of some a-amino acids. II: Rotational isomerism
    • Pachler K.G.R. Nuclear magnetic resonance study of some a-amino acids. II: Rotational isomerism. Spectrochim Acta 20 (1964) 581-587
    • (1964) Spectrochim Acta , vol.20 , pp. 581-587
    • Pachler, K.G.R.1
  • 39
    • 0030817709 scopus 로고    scopus 로고
    • Conformational studies of RS-66271, an analog of parathyroid hormone-related protein with pronounced bone anabolic activity
    • Pellegrini M., Bisello A., Rosenblatt M., Chorev M., and Mierke D.F. Conformational studies of RS-66271, an analog of parathyroid hormone-related protein with pronounced bone anabolic activity. J Med Chem 40 (1997) 3025-3031
    • (1997) J Med Chem , vol.40 , pp. 3025-3031
    • Pellegrini, M.1    Bisello, A.2    Rosenblatt, M.3    Chorev, M.4    Mierke, D.F.5
  • 40
    • 0033539640 scopus 로고    scopus 로고
    • Molecular complex of cholecystokinin-8 and N-terminus of the cholecystokinin A receptor by NMR spectroscopy
    • Pellegrini M., and Mierke D.F. Molecular complex of cholecystokinin-8 and N-terminus of the cholecystokinin A receptor by NMR spectroscopy. Biochemistry 38 (1999) 14775-14783
    • (1999) Biochemistry , vol.38 , pp. 14775-14783
    • Pellegrini, M.1    Mierke, D.F.2
  • 41
    • 0029740203 scopus 로고    scopus 로고
    • Probing the stereochemical requirements for receptor recognition of opioid agonists through topographic modifications in position 1
    • Qian X., Shenderovich M.D., Kövér K.E., Davis P., Horváth R., Zalewska T., et al. Probing the stereochemical requirements for receptor recognition of opioid agonists through topographic modifications in position 1. J Am Chem Soc 118 (1996) 7280-7289
    • (1996) J Am Chem Soc , vol.118 , pp. 7280-7289
    • Qian, X.1    Shenderovich, M.D.2    Kövér, K.E.3    Davis, P.4    Horváth, R.5    Zalewska, T.6
  • 43
    • 0018170065 scopus 로고
    • Determination of the intramolecular tyrosine-tryptophan distance in a 7-peptide related to the C-terminal sequence of cholecystokinin
    • Schiller P.W., Natarajan S., and Bodanszky M. Determination of the intramolecular tyrosine-tryptophan distance in a 7-peptide related to the C-terminal sequence of cholecystokinin. Int J Pept Protein Res 12 (1978) 139-142
    • (1978) Int J Pept Protein Res , vol.12 , pp. 139-142
    • Schiller, P.W.1    Natarajan, S.2    Bodanszky, M.3
  • 44
    • 0023024852 scopus 로고
    • Molecular mechanism of opioid receptor selection
    • Schwyzer R. Molecular mechanism of opioid receptor selection. Biochemistry 25 (1986) 6335-6342
    • (1986) Biochemistry , vol.25 , pp. 6335-6342
    • Schwyzer, R.1
  • 47
    • 0035063380 scopus 로고    scopus 로고
    • Mechanisms of opioid-induced pain and antinociceptive tolerance: descending facilitation and spinal dynorphin
    • Vanderah T.W., Ossipov M.H., Lai J., Malan Jr. T.P., and Porreca F. Mechanisms of opioid-induced pain and antinociceptive tolerance: descending facilitation and spinal dynorphin. Pain 92 (2001) 5-9
    • (2001) Pain , vol.92 , pp. 5-9
    • Vanderah, T.W.1    Ossipov, M.H.2    Lai, J.3    Malan Jr., T.P.4    Porreca, F.5
  • 48
    • 0021965655 scopus 로고
    • Cholecystokinin antagonists selectively potentiate analgesia induced by endogenous opiates
    • Watkins L.R., Kinscheck I.B., Kaufman E.F., Miller J., Frenk H., and Mayer D.J. Cholecystokinin antagonists selectively potentiate analgesia induced by endogenous opiates. Brain Res 327 (1985) 181-190
    • (1985) Brain Res , vol.327 , pp. 181-190
    • Watkins, L.R.1    Kinscheck, I.B.2    Kaufman, E.F.3    Miller, J.4    Frenk, H.5    Mayer, D.J.6
  • 50
    • 0030603863 scopus 로고    scopus 로고
    • The role of cholecystokinin in nociception, neuropathic pain and opiate tolerance
    • Wiesenfeld-Hallin Z., and Xu X.J. The role of cholecystokinin in nociception, neuropathic pain and opiate tolerance. Regul Pept 65 (1996) 23-28
    • (1996) Regul Pept , vol.65 , pp. 23-28
    • Wiesenfeld-Hallin, Z.1    Xu, X.J.2
  • 51
    • 0036967449 scopus 로고    scopus 로고
    • The role of spinal cholecystokinin in chronic pain states
    • Wiesenfeld-Hallin Z., Xu X.J., and Hokfelt T. The role of spinal cholecystokinin in chronic pain states. Pharmacol Toxicol 91 (2002) 398-403
    • (2002) Pharmacol Toxicol , vol.91 , pp. 398-403
    • Wiesenfeld-Hallin, Z.1    Xu, X.J.2    Hokfelt, T.3


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