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Volumn 9, Issue 10, 2003, Pages 649-657

Potent side-chain to side-chain cyclized dermorphin analogues containing a carbonyl bridge

Author keywords

Conformation; Cyclic opioid peptides; EDMC; NMR; Side chain to side chain cyclization; Solid phase synthesis; Structure activity relationship

Indexed keywords

BRIDGED COMPOUND; CARBONYL DERIVATIVE; DELTORPHIN; DELTORPHIN DERIVATIVE; DERMORPHIN; DERMORPHIN DERIVATIVE; ENKEPHALIN DERIVATIVE; LYSINE; OPIATE PEPTIDE; PHENYLALANINE; TYROSINE; UNCLASSIFIED DRUG;

EID: 0242363134     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/psc.510     Document Type: Article
Times cited : (20)

References (38)
  • 1
    • 0000447708 scopus 로고
    • Undenfriend S, Meienhofer J (eds). Academic Press: Orlando, FL
    • Schiller PW. In The Peptides: Analysis, Synthesis, Biology, Vol. 6, Undenfriend S, Meienhofer J (eds). Academic Press: Orlando, FL 1984; 219-268.
    • (1984) The Peptides: Analysis, Synthesis, Biology , vol.6 , pp. 219-268
    • Schiller, P.W.1
  • 5
    • 0010642390 scopus 로고
    • A cyclic enkephalin analog with high in vitro opiate activity
    • DiMaio J, Schiller PW. A cyclic enkephalin analog with high in vitro opiate activity. Proc. Natl Acad. Sci. USA 1980; 77: 7162-7166.
    • (1980) Proc. Natl. Acad. Sci. USA , vol.77 , pp. 7162-7166
    • DiMaio, J.1    Schiller, P.W.2
  • 6
    • 0020446397 scopus 로고
    • Synthesis and pharmacological characterization in vitro of cyclic enkephalin analogs: Effect of conformational constraints on opiate receptor selectivity
    • DiMaio J, Nguyen TM-D, Lemieux C, Schiller PW. Synthesis and pharmacological characterization in vitro of cyclic enkephalin analogs: effect of conformational constraints on opiate receptor selectivity. J. Med. Chem. 1982; 25: 1432-1438.
    • (1982) J. Med. Chem. , vol.25 , pp. 1432-1438
    • DiMaio, J.1    Nguyen, T.M.-D.2    Lemieux, C.3    Schiller, P.W.4
  • 7
    • 85004775289 scopus 로고
    • Synthesis of side-chain to side-chain cyclized peptide analogs on solid supports
    • Schiller PW, Nguyen TM-D, Miller. Synthesis of side-chain to side-chain cyclized peptide analogs on solid supports. Int. J. Peptide Protein Res. 1985; 25: 171-177.
    • (1985) Int. J. Peptide Protein Res. , vol.25 , pp. 171-177
    • Schiller, P.W.1    Nguyen, T.M.-D.2    Miller, A.3
  • 8
    • 0031179212 scopus 로고    scopus 로고
    • Synthesis of a novel side-chain to side-chain cyclized enkephalin analogue containing a carbonyl bridge
    • Pawlak D, Chung NN, Schiller PW, Izdebski J. Synthesis of a novel side-chain to side-chain cyclized enkephalin analogue containing a carbonyl bridge. J. Peptide. Sci. 1997; 3: 277-281.
    • (1997) J. Peptide. Sci. , vol.3 , pp. 277-281
    • Pawlak, D.1    Chung, N.N.2    Schiller, P.W.3    Izdebski, J.4
  • 9
    • 0035060228 scopus 로고    scopus 로고
    • Highly potent side-chain to side-chain cyclized enkephalin analogues containing a carbonyl bridge: Synthesis, biology and conformation
    • Pawlak D, Oleszczuk M, Wójcik J, Pachulska M, Chung NN, Schiller PW, Izdebski J. Highly potent side-chain to side-chain cyclized enkephalin analogues containing a carbonyl bridge: synthesis, biology and conformation. J. Peptide Sci. 2001; 7: 128-140.
    • (2001) J. Peptide Sci. , vol.7 , pp. 128-140
    • Pawlak, D.1    Oleszczuk, M.2    Wójcik, J.3    Pachulska, M.4    Chung, N.N.5    Schiller, P.W.6    Izdebski, J.7
  • 10
    • 0028034675 scopus 로고
    • N-cyclohexyl-N′-isopropylcarbodiimide: A hybrid that combines the structural features of DCC and DIC
    • Izdebski J, Pachulska M, Orłowska A. N-cyclohexyl-N′-isopropylcarbodiimide: a hybrid that combines the structural features of DCC and DIC. Int. J. Peptide Protein Res. 1994; 44: 414-419.
    • (1994) Int. J. Peptide Protein Res. , vol.44 , pp. 414-419
    • Izdebski, J.1    Pachulska, M.2    Orłowska, A.3
  • 11
    • 84916149980 scopus 로고
    • The action of morphine and related substances on contraction and on acetylcholine output of coaxially stimulated guinea pig ileum
    • Paton WDM. The action of morphine and related substances on contraction and on acetylcholine output of coaxially stimulated guinea pig ileum. Br. J. Pharmacol. 1957; 12: 119-127.
    • (1957) Br. J. Pharmacol. , vol.12 , pp. 119-127
    • Paton, W.D.M.1
  • 12
    • 0015455807 scopus 로고
    • A new example of a morphine sensitive neuroeffector junction
    • Henderson G, Hughes J, Kosterlitz H. A new example of a morphine sensitive neuroeffector junction. Br. J. Pharmacol. 1972; 46: 764-766.
    • (1972) Br. J. Pharmacol. , vol.46 , pp. 764-766
    • Henderson, G.1    Hughes, J.2    Kosterlitz, H.3
  • 13
  • 14
    • 0010642390 scopus 로고
    • A cyclic enkephalin analog with high in vitro opiate activity
    • DiMaio J, Schiller PW. A cyclic enkephalin analog with high in vitro opiate activity. Proc. Natl Acad. Sci. USA. 1980; 77: 7162-7166.
    • (1980) Proc. Natl. Acad. Sci. USA. , vol.77 , pp. 7162-7166
    • DiMaio, J.1    Schiller, P.W.2
  • 16
    • 0006393051 scopus 로고
    • Two-dimensional spectroscopy. Application to nuclear magnetic resonance
    • Aue WP, Bartholdi E, Ernst RR. Two-dimensional spectroscopy. Application to nuclear magnetic resonance. J. Chem. Phys. 1976; 64: 2229-2246.
    • (1976) J. Chem. Phys. , vol.64 , pp. 2229-2246
    • Aue, W.P.1    Bartholdi, E.2    Ernst, R.R.3
  • 17
    • 0000161163 scopus 로고
    • Enhanced NMR resolution by restricting the effective sample volume
    • Bax A, Freeman R. Enhanced NMR resolution by restricting the effective sample volume. J. Magn. Reson. 1985; 65: 355-360.
    • (1985) J. Magn. Reson. , vol.65 , pp. 355-360
    • Bax, A.1    Freeman, R.2
  • 18
    • 0344448273 scopus 로고
    • Coherence transfer by isotropic mixing; application to proton correlation spectroscopy
    • Braunschweiler L, Ernst RR. 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
  • 19
    • 0011491177 scopus 로고
    • Structure determination of a tetrasaccharide: Transient nuclear Overhauser effects in the rotating frame
    • Bothner-By AA, Stephens RL, Lee J-M, Warren CD, Jeanloz RW. Structure determination of a tetrasaccharide: Transient nuclear Overhauser effects in the rotating frame. J. Am. Chem. Soc. 1984; 106: 811-813.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 811-813
    • Bothner-By, A.A.1    Stephens, R.L.2    Lee, J.-M.3    Warren, C.D.4    Jeanloz, R.W.5
  • 20
    • 5144229966 scopus 로고
    • Practical aspects of two-dimensional transverse NOE spectroscopy
    • Bax A, Davis DG. Practical aspects of two-dimensional transverse NOE spectroscopy. J. Magn. Reson. 1985; 63: 207-213.
    • (1985) J. Magn. Reson. , vol.63 , pp. 207-213
    • Bax, A.1    Davis, D.G.2
  • 21
    • 0033252424 scopus 로고    scopus 로고
    • Conformational analysis of a novel cyclic enkephalin analogue using NMR and EDMC calculations
    • Sidor M, Wójcik J, Pawlak D, Izdebski J. Conformational analysis of a novel cyclic enkephalin analogue using NMR and EDMC calculations. Acta Biochim. Polon. 1999; 46: 641-650.
    • (1999) Acta Biochim. Polon. , vol.46 , pp. 641-650
    • Sidor, M.1    Wójcik, J.2    Pawlak, D.3    Izdebski, J.4
  • 22
    • 84889582115 scopus 로고    scopus 로고
    • NMR chemical shifts of common laboratory solvents as trace impurities
    • Gottlieb HE, Kotlyar V, Nudelman A. NMR chemical shifts of common laboratory solvents as trace impurities. J. Org. Chem. 1997; 62: 7512-7515.
    • (1997) J. Org. Chem. , vol.62 , pp. 7512-7515
    • Gottlieb, H.E.1    Kotlyar, V.2    Nudelman, A.3
  • 24
    • 0024066560 scopus 로고
    • On the multiple-minima problem in the conformational analysis of polypeptides. II. An electrostatically driven Monte Carlo method - Tests on poly(L-alanine)
    • Ripoll D, Scheraga HA. On the multiple-minima problem in the conformational analysis of polypeptides. II. An electrostatically driven Monte Carlo method - tests on poly(L-alanine). Biopolymers 1988; 27: 1283-1303.
    • (1988) Biopolymers , vol.27 , pp. 1283-1303
    • Ripoll, D.1    Scheraga, H.A.2
  • 25
    • 0025045674 scopus 로고
    • On the multiple-minima problem in the conformational analysis of polypeptides. IV. Application of the electrostatically driven Monte Carlo method to the 20-residue membrane-bound portion of melittin
    • Ripoll D, Scheraga HA. On the multiple-minima problem in the conformational analysis of polypeptides. IV. Application of the electrostatically driven Monte Carlo method to the 20-residue membrane-bound portion of melittin. Biopolymers 1990; 30: 165-176.
    • (1990) Biopolymers , vol.30 , pp. 165-176
    • Ripoll, D.1    Scheraga, H.A.2
  • 26
    • 0001731773 scopus 로고
    • Energy parameters in polypeptides. 10. Improved geometrical parameters and nonbonded interactions for use in the ECEPP/3 algorithm, with application to proline-containing peptides
    • Nemethy G, Gibson KD, Palmer KA, Yoon ChN, Paterlini G, Zagari A, Rumsey S, Scheraga HA. Energy parameters in polypeptides. 10. Improved geometrical parameters and nonbonded interactions for use in the ECEPP/3 algorithm, with application to proline-containing peptides. J. Phys. Chem. 1992; 96: 6472-6484.
    • (1992) J. Phys. Chem. , vol.96 , pp. 6472-6484
    • Nemethy, G.1    Gibson, K.D.2    Palmer, K.A.3    Yoon, Ch.N.4    Paterlini, G.5    Zagari, A.6    Rumsey, S.7    Scheraga, H.A.8
  • 27
    • 0026076082 scopus 로고
    • Empirical solvation models can be used to differentiate native from near-native conformations of bovine pancreatic trypsin inhibitor
    • Vila J, Williams RI, Vasquez M, Scheraga HA. Empirical solvation models can be used to differentiate native from near-native conformations of bovine pancreatic trypsin inhibitor. Proteins: Struct. Fun. Gen. 1991; 10: 199-218.
    • (1991) Proteins: Struct. Fun. Gen. , vol.10 , pp. 199-218
    • Vila, J.1    Williams, R.I.2    Vasquez, M.3    Scheraga, H.A.4
  • 28
    • 0023430366 scopus 로고
    • Monte Carlo-minimization approach to the multiple-minima problem in protein folding
    • Li Z, Scheraga HA. Monte Carlo-minimization approach to the multiple-minima problem in protein folding. Proc. Natl Acad. Sci. USA 1987; 84: 6611-6615.
    • (1987) Proc. Natl. Acad. Sci. USA , vol.84 , pp. 6611-6615
    • Li, Z.1    Scheraga, H.A.2
  • 29
    • 0002164256 scopus 로고
    • On the multiple-minima problem in the conformational analysis of polypeptides. I. Backbone degrees of freedom for a perturbed α-helix
    • Piela L, Scheraga HA. On the multiple-minima problem in the conformational analysis of polypeptides. I. Backbone degrees of freedom for a perturbed α-helix. Biopolymers 1987; 26: S33-S58.
    • (1987) Biopolymers , vol.26
    • Piela, L.1    Scheraga, H.A.2
  • 33
    • 0000455182 scopus 로고
    • On the evaluation of interproton distances for three-dimensional structure by NMR using a relaxation rate matrix analysis
    • Post CB, Meadows RP, Gorenstein DG. On the evaluation of interproton distances for three-dimensional structure by NMR using a relaxation rate matrix analysis. J. Am. Chem. Soc. 1990; 112: 6796-6803.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6796-6803
    • Post, C.B.1    Meadows, R.P.2    Gorenstein, D.G.3
  • 34
    • 0000169232 scopus 로고
    • An algorithm for least-squares estimation of nonlinear parameters
    • Marquardt DW. An algorithm for least-squares estimation of nonlinear parameters. J. Soc. Indust. Appl. Math. 1963; 11: 431-441.
    • (1963) J. Soc. Indust. Appl. Math. , vol.11 , pp. 431-441
    • Marquardt, D.W.1
  • 35
    • 0030065629 scopus 로고    scopus 로고
    • Opioid infidelity: Novel opioid peptides with dual high affinity for δ- and μ-receptors
    • Lazarus LH, Bryant SD, Salvadori S, Attila M, Jones LS. Opioid infidelity: novel opioid peptides with dual high affinity for δ- and μ-receptors. Trends Neurosci. 1996; 19: 31-35.
    • (1996) Trends Neurosci. , vol.19 , pp. 31-35
    • Lazarus, L.H.1    Bryant, S.D.2    Salvadori, S.3    Attila, M.4    Jones, L.S.5
  • 36
    • 0022353005 scopus 로고
    • Synthesis and activity of novel cyclic opioid peptide monomers and dimers
    • Schiller PW, Nguyen TM-D, Lemieux C, Maziak LA. Synthesis and activity of novel cyclic opioid peptide monomers and dimers. J. Med. Chem. 1985; 28: 1766-1771.
    • (1985) J. Med. Chem. , vol.28 , pp. 1766-1771
    • Schiller, P.W.1    Nguyen, T.M.-D.2    Lemieux, C.3    Maziak, L.A.4
  • 37
    • 0025987566 scopus 로고
    • Conformational restriction of the phenylalanine residue in a cyclic opioid peptide analogue: Effects on receptor selectivity and stereospecificity
    • Schiller PW, Weltrowska G, Nguyen TM-D, Lemieux C, Chung NN, Marsden BJ, Wilkes BC. Conformational restriction of the phenylalanine residue in a cyclic opioid peptide analogue: effects on receptor selectivity and stereospecificity. J. Med. Chem. 1991; 34: 3125-3132.
    • (1991) J. Med. Chem. , vol.34 , pp. 3125-3132
    • Schiller, P.W.1    Weltrowska, G.2    Nguyen, T.M.-D.3    Lemieux, C.4    Chung, N.N.5    Marsden, B.J.6    Wilkes, B.C.7
  • 38
    • 0029881007 scopus 로고    scopus 로고
    • MOLMOL: A program for display and analysis of macromolecular structures
    • Koradi R, Billeter M, Wüthrich K. MOLMOL: a program for display and analysis of macromolecular structures. J. Mol. Graphics 1996; 14: 52-55.
    • (1996) J. Mol. Graphics , vol.14 , pp. 52-55
    • Koradi, R.1    Billeter, M.2    Wüthrich, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.