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Volumn 40, Issue 14, 1997, Pages 2228-2240

Design of a potent combined pseudopeptide endothelin-a/endothelin-b receptor antagonist, ac-dBhg16-Leu-Asp-IIe-[NMe]IIe-Trp21 (PD 156252): Examination of its pharmacokinetic and spectral properties

Author keywords

[No Author keywords available]

Indexed keywords

ENDOTHELIN A RECEPTOR ANTAGONIST; ENDOTHELIN B RECEPTOR ANTAGONIST; N ACETYL 10,11 DIHYDRO 5H DIBENZO[A,D]CYCLOHEPTEN 5 YLGLYCYLLEUCYLASPARTYLISOLEUCYLISOLEUCYLTRYPTOPHAN; N ACETYL 3,3 DIPHENYL DEXTRO ALANYLLEUCYLASPARTYLISOLEUCYLISOLEUCYLTRYPTOPHAN; PD 156252; UNCLASSIFIED DRUG;

EID: 0030746698     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970161m     Document Type: Article
Times cited : (102)

References (72)
  • 1
    • 0022067275 scopus 로고
    • Characterization of a coronary vasoconstrictor produced by endothelial cells in culture
    • Hickey, K. A.; Rubanyi, G.; Paul, R. J.; Highsmith, R. F. Characterization of a coronary vasoconstrictor produced by endothelial cells in culture. Am. J. Physiol. 1985, 248, C550-C556.
    • (1985) Am. J. Physiol. , vol.248
    • Hickey, K.A.1    Rubanyi, G.2    Paul, R.J.3    Highsmith, R.F.4
  • 4
    • 0013543367 scopus 로고
    • The human endothelin family: Three structurally and pharmacologically distinct isopeptides predicted by three separate genes
    • Inoue, A.; Yanagisawa, M.; Kimura, S.; Kasuya, Y.; Miyauchi, T.; Goto, K.; Masaki, T. The human endothelin family: Three structurally and pharmacologically distinct isopeptides predicted by three separate genes. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 2863-2867.
    • (1989) Proc. Natl. Acad. Sci. U.S.A. , vol.86 , pp. 2863-2867
    • Inoue, A.1    Yanagisawa, M.2    Kimura, S.3    Kasuya, Y.4    Miyauchi, T.5    Goto, K.6    Masaki, T.7
  • 5
    • 0024433980 scopus 로고
    • A novel peptide, vasoactive intestinal contractor, of a new (endothelin) peptide family. Molecular cloning, expression and biological activity
    • Saida, K.; Mitsui, Y.; Ishida, N. A novel peptide, vasoactive intestinal contractor, of a new (endothelin) peptide family. Molecular cloning, expression and biological activity. J. Biol. Chem. 1989, 264, 14613-14616.
    • (1989) J. Biol. Chem. , vol.264 , pp. 14613-14616
    • Saida, K.1    Mitsui, Y.2    Ishida, N.3
  • 6
    • 0024286312 scopus 로고
    • Sarafotoxin, a novel vasoconstrictor peptide: Phosphoinositide hydrolysis in rat heart and brain
    • Kloog, T.; Ambar, I.; Sokolovsky, M.; Kochva, E.; Wolberg, Z.; Bdolah, A. Sarafotoxin, a novel vasoconstrictor peptide: Phosphoinositide hydrolysis in rat heart and brain. Science 1988, 242, 268-270.
    • (1988) Science , vol.242 , pp. 268-270
    • Kloog, T.1    Ambar, I.2    Sokolovsky, M.3    Kochva, E.4    Wolberg, Z.5    Bdolah, A.6
  • 7
    • 0024467196 scopus 로고
    • SRTX-d, a new native peptide of the endothelin/sarafotoxin family
    • Bdolah, A.; Wolberg, Z.; Fleminger, G.; Kochva, E. SRTX-d, a new native peptide of the endothelin/sarafotoxin family. FEBS Lett. 1989, 251, 1-3.
    • (1989) FEBS Lett. , vol.251 , pp. 1-3
    • Bdolah, A.1    Wolberg, Z.2    Fleminger, G.3    Kochva, E.4
  • 8
    • 0027391870 scopus 로고
    • Bibrotoxin, a novel member of the endothelin/ sarafotoxin peptide family, from the venom of the burrowing asp, Atractaspis bibroni
    • Becker, A.; Dowdle, E. B.; Hechler, U.; Kauser, K.; Donner, P.; Schleuning, W. D. Bibrotoxin, a novel member of the endothelin/ sarafotoxin peptide family, from the venom of the burrowing asp, Atractaspis bibroni. FEBS Lett. 1993, 315, 100-103.
    • (1993) FEBS Lett. , vol.315 , pp. 100-103
    • Becker, A.1    Dowdle, E.B.2    Hechler, U.3    Kauser, K.4    Donner, P.5    Schleuning, W.D.6
  • 9
    • 0026764585 scopus 로고
    • Endothelin: A new challenge
    • Doherty, A. M. Endothelin: A new challenge. J. Med. Chem. 1992, 35, 1493-1508.
    • (1992) J. Med. Chem. , vol.35 , pp. 1493-1508
    • Doherty, A.M.1
  • 10
    • 0027424285 scopus 로고
    • The structure and specificity of endothelin receptors: Their importance in physiology and medicine
    • Huggins, J. P.; Pelton, J. T.; Miller, R. C. The structure and specificity of endothelin receptors: Their importance in physiology and medicine. Pharmacol. Ther. 1993, 59, 55-123.
    • (1993) Pharmacol. Ther. , vol.59 , pp. 55-123
    • Huggins, J.P.1    Pelton, J.T.2    Miller, R.C.3
  • 11
    • 0028311861 scopus 로고
    • Development of agents to modulate the effects of endothelin
    • Cheng, X. M.; Nikam, S. S.; Doherty, A. M. Development of agents to modulate the effects of endothelin. Cur. Med. Chem. 1995, 1, 271-312.
    • (1995) Cur. Med. Chem. , vol.1 , pp. 271-312
    • Cheng, X.M.1    Nikam, S.S.2    Doherty, A.M.3
  • 12
    • 0028940659 scopus 로고
    • Development of agents to modulate the effects of endothelin
    • Cody, W. L.; Doherty, A. M. Development of agents to modulate the effects of endothelin. Biopolymers (Pept. Sci.) 1995, 37, 89-104.
    • (1995) Biopolymers (Pept. Sci.) , vol.37 , pp. 89-104
    • Cody, W.L.1    Doherty, A.M.2
  • 13
    • 0025605345 scopus 로고
    • Cloning and expression of a cDNA encoding an endothelin receptor
    • Arai, H.; Hori, T.; Aramori, I.; Ohkubo, H.; Nakanishi, S. Cloning and expression of a cDNA encoding an endothelin receptor. Nature (London) 1990, 348, 730-732.
    • (1990) Nature (London) , vol.348 , pp. 730-732
    • Arai, H.1    Hori, T.2    Aramori, I.3    Ohkubo, H.4    Nakanishi, S.5
  • 18
    • 0025854756 scopus 로고
    • Presence of non-selective type of endothelin receptor on vascular endothelium and its linkage to vasodilation
    • Takayanagi, R.; Kitazumi, K.; Takasaki, C.; Ohnaka, K.; Aimoto, S.; Tasaka, K.; Ohashi, M.; Nawata, H. Presence of non-selective type of endothelin receptor on vascular endothelium and its linkage to vasodilation. FEBS. Lett. 1991, 282, 103-106.
    • (1991) FEBS. Lett. , vol.282 , pp. 103-106
    • Takayanagi, R.1    Kitazumi, K.2    Takasaki, C.3    Ohnaka, K.4    Aimoto, S.5    Tasaka, K.6    Ohashi, M.7    Nawata, H.8
  • 21
    • 0027300076 scopus 로고
    • A novel type of endothelin B receptor mediating contraction in swine pulmonary vein
    • Sudjarwo, S. A.; Hori, M.; Takai, M.; Urade, Y.; Okada, T.; Karaki, H. A novel type of endothelin B receptor mediating contraction in swine pulmonary vein. Life Sci. 1993, 53, 431-437.
    • (1993) Life Sci. , vol.53 , pp. 431-437
    • Sudjarwo, S.A.1    Hori, M.2    Takai, M.3    Urade, Y.4    Okada, T.5    Karaki, H.6
  • 22
    • 0027185110 scopus 로고
    • Use of the endothelin antagonists BQ-123 and PD 142893 to reveal three endothelin receptors mediating smooth muscle contraction and the release of EDRF
    • Warner, T. D.; Allcock, G. H.; Corder, R.; Vane, J. R. Use of the endothelin antagonists BQ-123 and PD 142893 to reveal three endothelin receptors mediating smooth muscle contraction and the release of EDRF. Br. J. Pharmacol. 1993, 110, 777-782.
    • (1993) Br. J. Pharmacol. , vol.110 , pp. 777-782
    • Warner, T.D.1    Allcock, G.H.2    Corder, R.3    Vane, J.R.4
  • 35
    • 0008560922 scopus 로고    scopus 로고
    • Conformational analysis of peptides: Application to drug design
    • Craik, D. J., Ed.; CRC Press: Boca Raton, FL
    • Kessler, H.; Knot, R. K.; Schmitt, W. Conformational analysis of peptides: Application to drug design. In NMR Drug Design; Craik, D. J., Ed.; CRC Press: Boca Raton, FL, 1996; pp 215-244.
    • (1996) NMR Drug Design , pp. 215-244
    • Kessler, H.1    Knot, R.K.2    Schmitt, W.3
  • 36
    • 0025054575 scopus 로고
    • Reinvestigation of the conformation of cyclosporin A in chloroform
    • Kessler, H.; Köck, M.; Wein, T.; Gehrke, M. Reinvestigation of the conformation of cyclosporin A in chloroform. Helv. Chim. Acta 1990, 73, 1818-1832.
    • (1990) Helv. Chim. Acta , vol.73 , pp. 1818-1832
    • Kessler, H.1    Köck, M.2    Wein, T.3    Gehrke, M.4
  • 37
    • 0027446409 scopus 로고
    • Structure of rapamycin: An NMR and molecular-dynamics investigation
    • Kessler, H.; Haessner, R.; Schüler, W. Structure of rapamycin: An NMR and molecular-dynamics investigation. Helv. Chim. Acta 1993, 76, 117-130.
    • (1993) Helv. Chim. Acta , vol.76 , pp. 117-130
    • Kessler, H.1    Haessner, R.2    Schüler, W.3
  • 39
    • 0028100316 scopus 로고
    • 5]enkephalin, a highly potent, δ-opioid receptor selective compound: Comparisons with proposed solution conformations
    • 5]enkephalin, a highly potent, δ-opioid receptor selective compound: Comparisons with proposed solution conformations. J. Am. Chem. Soc. 1994, 116, 7523-7531
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 7523-7531
    • Flippen-Anderson, J.L.1    Hruby, V.J.2    Collins, N.3    George, C.4    Cudney, B.5
  • 40
    • 0031028837 scopus 로고    scopus 로고
    • Multiconformational NMR analysis of sandostatin (octreotide): Equilibrium between β-sheet and helical structures
    • Melacini, G.; Zhu, Q.; Goodman, M. Multiconformational NMR analysis of sandostatin (octreotide): Equilibrium between β-sheet and helical structures. Biochemistry 1997. 36, 1233-1241.
    • (1997) Biochemistry , vol.36 , pp. 1233-1241
    • Melacini, G.1    Zhu, Q.2    Goodman, M.3
  • 42
    • 0001006731 scopus 로고
    • Structure-induced carbon-13 chemical shifts: A sensitive measure of transient localized secondary structure in peptides
    • Reily, M. D.; Thanabal, V.; Omecinsky, D. O. Structure-induced carbon-13 chemical shifts: A sensitive measure of transient localized secondary structure in peptides. J. Am. Chem. Soc. 1992, 114, 6251-6252.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 6251-6252
    • Reily, M.D.1    Thanabal, V.2    Omecinsky, D.O.3
  • 45
    • 0017303940 scopus 로고
    • Tert-butoxycarbonylaminoacyl-4-(oxymethyl)-phenylacetamidomethyl-resin, a more acid-resistant support for solide-phase peptide synthesis
    • Mitchell, A. R.; Erickson, B. W.; Ryabtsev, M. N.; Hodges, R. S.; Merrifield, R. B. Tert-butoxycarbonylaminoacyl-4-(oxymethyl)-phenylacetamidomethyl-resin, a more acid-resistant support for solide-phase peptide synthesis. J. Am. Chem. Soc. 1976, 98, 7357-7562.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 7357-7562
    • Mitchell, A.R.1    Erickson, B.W.2    Ryabtsev, M.N.3    Hodges, R.S.4    Merrifield, R.B.5
  • 46
    • 0026753844 scopus 로고
    • Chiral synthesis of D- And L-3,3-diphenylalanine (DIP), unusual I-amino acids for peptides of biological interest
    • Chen, H. G.; Beylin, V. G.; Leja, B.; Goel, O. P. Chiral synthesis of D-and L-3,3-diphenylalanine (DIP), unusual I-amino acids for peptides of biological interest. Tetrahedron Lett. 1992, 33, 3293-3296.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3293-3296
    • Chen, H.G.1    Beylin, V.G.2    Leja, B.3    Goel, O.P.4
  • 47
    • 0027413331 scopus 로고
    • Cyclic derivatives of 3,3-diphenylalanine (Dip). II. Novel I-amino acids for peptides of biological interest
    • Beylin, V. G.; Chen, H. G.; Dunbar, J. B.; Goel, O. P.; Harter, W.; Marlett, M.; Topliss, J. G. Cyclic derivatives of 3,3-diphenylalanine (Dip). II. Novel I-amino acids for peptides of biological interest. Tetrahedron Lett. 1992, 34, 953-956.
    • (1992) Tetrahedron Lett. , vol.34 , pp. 953-956
    • Beylin, V.G.1    Chen, H.G.2    Dunbar, J.B.3    Goel, O.P.4    Harter, W.5    Marlett, M.6    Topliss, J.G.7
  • 48
    • 0025449863 scopus 로고
    • Synthesis and resolution of novel 3′-substituted phenylalanine amides
    • Knittel, J. J.; He, J. X. Synthesis and resolution of novel 3′-substituted phenylalanine amides. Pept. Res. 1990, 3, 176-181.
    • (1990) Pept. Res. , vol.3 , pp. 176-181
    • Knittel, J.J.1    He, J.X.2
  • 49
    • 0023150034 scopus 로고
    • 2NH peptide bond isostere
    • 2NH peptide bond isostere. Peptides 1987, 8, 119-121.
    • (1987) Peptides , vol.8 , pp. 119-121
    • Sasaki, Y.1    Coy, D.H.2
  • 51
    • 85004872164 scopus 로고
    • An efficient synthesis of optically active α-(t-butoxycarbonylamino)-aldehydes from α-amino acids
    • Fehrentz, J. A.; Castro, B. An efficient synthesis of optically active α-(t-butoxycarbonylamino)-aldehydes from α-amino acids. Synthesis 1983, 676-678.
    • (1983) Synthesis , pp. 676-678
    • Fehrentz, J.A.1    Castro, B.2
  • 52
    • 0027261275 scopus 로고
    • New method for the synthesis of N-methyl amino acids containing peptides by reductive methylation of amino groups on the solid phase
    • Kaljuste, K.; Unden, A. New method for the synthesis of N-methyl amino acids containing peptides by reductive methylation of amino groups on the solid phase. Int. J. Pept. Protein Res. 1993, 42, 118-124.
    • (1993) Int. J. Pept. Protein Res. , vol.42 , pp. 118-124
    • Kaljuste, K.1    Unden, A.2
  • 53
    • 0002840747 scopus 로고
    • Synthesis of 9-fluorenylmethyloxycarbonyl-protected N-alkyl amino acids by reduction of oxazolidinones
    • Freidinger, R. M.; Hinkle, J. S.; Perlow, D. S. Synthesis of 9-fluorenylmethyloxycarbonyl-protected N-alkyl amino acids by reduction of oxazolidinones. J. Org. Chem. 1983, 48, 77-81.
    • (1983) J. Org. Chem. , vol.48 , pp. 77-81
    • Freidinger, R.M.1    Hinkle, J.S.2    Perlow, D.S.3
  • 54
    • 0014772602 scopus 로고
    • Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides
    • Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 1970, 34, 595-598.
    • (1970) Anal. Biochem. , vol.34 , pp. 595-598
    • Kaiser, E.1    Colescott, R.L.2    Bossinger, C.D.3    Cook, P.I.4
  • 55
    • 0028657017 scopus 로고
    • Enzymic barriers for GI peptide and protein delivery
    • Woodley, J. F. Enzymic barriers for GI peptide and protein delivery. Crit. Rev. Ther. Drug Carrier Syst. 1994, 11, 61-95.
    • (1994) Crit. Rev. Ther. Drug Carrier Syst. , vol.11 , pp. 61-95
    • Woodley, J.F.1
  • 56
    • 85069107554 scopus 로고    scopus 로고
    • Parke-Davis Pharmaceutical Research, Division of Warner-Lambert Co., unpublished results
    • Cody, W. L.; He, J. X.; Flynn, M. A.; Welch, K. M.; Reynolds, E. E.; Doherty, A. M. Parke-Davis Pharmaceutical Research, Division of Warner-Lambert Co., unpublished results.
    • Cody, W.L.1    He, J.X.2    Flynn, M.A.3    Welch, K.M.4    Reynolds, E.E.5    Doherty, A.M.6
  • 57
    • 85069097456 scopus 로고
    • In vitro assessment of oral delivery for hexapeptide endothelin antagonists using stability in intestinal perfusate and Caco-2 permeability
    • Stewart, B. H.; Reyner, E. L.; Tse, E.; Hayes, R. N.; Cody, W. L.; Doherty, A. M. In vitro assessment of oral delivery for hexapeptide endothelin antagonists using stability in intestinal perfusate and Caco-2 permeability. Pharm. Res. 1994, 11, S-257.
    • (1994) Pharm. Res. , vol.11
    • Stewart, B.H.1    Reyner, E.L.2    Tse, E.3    Hayes, R.N.4    Cody, W.L.5    Doherty, A.M.6
  • 58
    • 0025804183 scopus 로고
    • Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells
    • Artursson, P.; Karlsson, J. Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem. Biophys. Res. Commun. 1991, 175, 880-885.
    • (1991) Biochem. Biophys. Res. Commun. , vol.175 , pp. 880-885
    • Artursson, P.1    Karlsson, J.2
  • 59
    • 0024593744 scopus 로고
    • Characterization of the human colon carcinoma cell line (Caco-2) as a model system for intestinal epithelial permeability
    • Hidalgo, I. J.; Raub, R. J.; Borchardt, R. T. Characterization of the human colon carcinoma cell line (Caco-2) as a model system for intestinal epithelial permeability. Gastroenterology 1989, 96, 736-749.
    • (1989) Gastroenterology , vol.96 , pp. 736-749
    • Hidalgo, I.J.1    Raub, R.J.2    Borchardt, R.T.3
  • 63
    • 0029181728 scopus 로고
    • 15N Random coil NMR chemical shifts of the common amino acids. I. Investigations of nearest neighbor effects
    • 15N Random coil NMR chemical shifts of the common amino acids. I. Investigations of nearest neighbor effects. J. Biomol. NMR 1995, 5, 67-81.
    • (1995) J. Biomol. NMR , vol.5 , pp. 67-81
    • Wishart, D.S.1    Bigam, C.G.2    Holm, A.3    Hodges, R.S.4    Sykes, B.D.5
  • 64
    • 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
  • 67
    • 5144233105 scopus 로고
    • Practical aspects of two-dimensional transverse NOE spectroscopy
    • Bax, A.; Davis, D. G. Practical aspects of two-dimensional transverse NOE spectroscopy. J. Magn. Reson. 1985, 65, 355-360.
    • (1985) J. Magn. Reson. , vol.65 , pp. 355-360
    • Bax, A.1    Davis, D.G.2
  • 68
    • 0019327003 scopus 로고
    • A two-dimensional nuclear Overhauser enhancement (2D NOE) experiment for the elucidation of complete proton-proton cross-relaxation networks in biological macromolecules
    • Kumar, A.; Ernst, R. R.; Wüthrich, K. A two-dimensional nuclear Overhauser enhancement (2D NOE) experiment for the elucidation of complete proton-proton cross-relaxation networks in biological macromolecules. Biochem. Biophys. Res. Commun. 1980, 95, 1-6.
    • (1980) Biochem. Biophys. Res. Commun. , vol.95 , pp. 1-6
    • Kumar, A.1    Ernst, R.R.2    Wüthrich, K.3
  • 69
    • 0021114895 scopus 로고
    • Application of phase sensitive two-dimensional correlated spectroscopy (COSY) for measurements of proton-proton spin-spin coupling constants in proteins
    • Marion, D.; Wüthrich, K. Application of phase sensitive two-dimensional correlated spectroscopy (COSY) for measurements of proton-proton 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
  • 70
    • 0029243371 scopus 로고
    • The solution structure of ω-Aga-IVB, a P-type calcium channel antagonist from venom of the funnel web spider, Agelenopsis aperta
    • Reily, M. D.; Thanabal, V.; Adams, M. E. The solution structure of ω-Aga-IVB, a P-type calcium channel antagonist from venom of the funnel web spider, Agelenopsis aperta. J. Biomol. NMR 1995, 5, 122-132.
    • (1995) J. Biomol. NMR , vol.5 , pp. 122-132
    • Reily, M.D.1    Thanabal, V.2    Adams, M.E.3
  • 71
    • 0027928701 scopus 로고
    • 13C chemical shifts of amino acids in aqueous solution containing organic solvents: Application to the secondary struture characterization of peptides in aqueous trifluoroethanol solution
    • 13C chemical shifts of amino acids in aqueous solution containing organic solvents: Application to the secondary struture characterization of peptides in aqueous trifluoroethanol solution. J. Biomol. NMR 1994, 4, 47-59.
    • (1994) J. Biomol. NMR , vol.4 , pp. 47-59
    • Thanabal, V.1    Omecinsky, D.O.2    Reily, M.D.3    Cody, W.L.4


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