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Volumn 55, Issue 14, 2012, Pages 6502-6511

Azapeptide analogues of the growth hormone releasing peptide 6 as cluster of differentiation 36 receptor ligands with reduced affinity for the growth hormone secretagogue receptor 1a

Author keywords

[No Author keywords available]

Indexed keywords

CD36 ANTIGEN; EP 80317; GHRELIN RECEPTOR; HEXARELIN; HISTIDYL DEXTRO TRYPTOPHYLALANYLTRYPTOPHYL DEXTRO PHENYLALANYLLYSINAMIDE; HISTIDYL DEXTRO TRYPTOPHYLALANYLTRYPTOPHYL DEXTRO PHENYLALANYLLYSINAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84864186354     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300557t     Document Type: Article
Times cited : (33)

References (48)
  • 1
    • 0021368643 scopus 로고
    • Conformational Energy Studies and in Vitro and in Vivo Activity Data on Growth Hormone-Releasing Peptides
    • Momany, F.; Bowers, C. Y.; Reynolds, G. A.; Hong, A.; Newlander, K. Conformational Energy Studies and in Vitro and in Vivo Activity Data on Growth Hormone-Releasing Peptides Endocrinology 1984, 114 (5) 1531-1536
    • (1984) Endocrinology , vol.114 , Issue.5 , pp. 1531-1536
    • Momany, F.1    Bowers, C.Y.2    Reynolds, G.A.3    Hong, A.4    Newlander, K.5
  • 2
    • 0028968462 scopus 로고
    • Blocked Growth Hormone-Releasing Peptide (GHRP-6)-Induced GH Secretion and Absence of the Synergic Action of GHRP-6 Plus GH-Releasing Hormone in Patients with Hypothalamopituitary Disconnection: Evidence That GHRP-6 Main Action Is Exerted at the Hypothalamic Level
    • Popovic, V.; Damjanovic, S.; Micic, D.; Djurovic, M.; Dieguez, C.; Casanueva, F. F. Blocked Growth Hormone-Releasing Peptide (GHRP-6)-Induced GH Secretion and Absence of the Synergic Action of GHRP-6 Plus GH-Releasing Hormone in Patients with Hypothalamopituitary Disconnection: Evidence That GHRP-6 Main Action Is Exerted at the Hypothalamic Level J. Clin. Endocrinol. Metab. 1995, 80 (3) 942-947
    • (1995) J. Clin. Endocrinol. Metab. , vol.80 , Issue.3 , pp. 942-947
    • Popovic, V.1    Damjanovic, S.2    Micic, D.3    Djurovic, M.4    Dieguez, C.5    Casanueva, F.F.6
  • 3
    • 0028265587 scopus 로고
    • Growth Hormone-Releasing Activity of Hexarelin, a New Synthetic Hexapeptide, after Intravenous, Subcutaneous, Intranasal, and Oral Administration in Man
    • Ghigo, E.; Arvat, E.; Gianotti, L.; Imbimbo, B. P.; Lenaerts, V.; Deghenghi, R.; Camanni, F. Growth Hormone-Releasing Activity of Hexarelin, a New Synthetic Hexapeptide, after Intravenous, Subcutaneous, Intranasal, and Oral Administration in Man J. Clin. Endocrinol. Metab. 1994, 78 (3) 693-698
    • (1994) J. Clin. Endocrinol. Metab. , vol.78 , Issue.3 , pp. 693-698
    • Ghigo, E.1    Arvat, E.2    Gianotti, L.3    Imbimbo, B.P.4    Lenaerts, V.5    Deghenghi, R.6    Camanni, F.7
  • 5
    • 0027419864 scopus 로고
    • Massive growth hormone (GH) discharge in obese subjects after the combined administration of GH-releasing hormone and GHRP-6: Evidence for a marked somatotroph secretory capability in obesity
    • Cordido, F.; Peñalva, A.; Dieguez, C.; Casanueva, F. F. Massive growth hormone (GH) discharge in obese subjects after the combined administration of GH-releasing hormone and GHRP-6: evidence for a marked somatotroph secretory capability in obesity J. Clin. Endocrinol. Metab. 1993, 76, 819-23
    • (1993) J. Clin. Endocrinol. Metab. , vol.76 , pp. 819-823
    • Cordido, F.1    Peñalva, A.2    Dieguez, C.3    Casanueva, F.F.4
  • 10
    • 0034101821 scopus 로고    scopus 로고
    • Targeted disruption of the class B scavenger receptor CD36 protects against atherosclerotic lesion development in mice
    • Febbraio, M.; Podrez, E. A.; Smith, J. D.; Hajjar, D. P.; Hazen, S. T.; Hoff, H. F.; Sharma, K.; Silverstein1, R. L Targeted disruption of the class B scavenger receptor CD36 protects against atherosclerotic lesion development in mice J. Clin. Invest. 2000, 105, 1049-1056
    • (2000) J. Clin. Invest. , vol.105 , pp. 1049-1056
    • Febbraio, M.1    Podrez, E.A.2    Smith, J.D.3    Hajjar, D.P.4    Hazen, S.T.5    Hoff, H.F.6    Sharma, K.7    Silverstein, R.L.8
  • 11
    • 4544363024 scopus 로고    scopus 로고
    • Identification of the growth hormone-releasing peptide binding site in CD36: A photoaffinity cross-linking study
    • Demers, A.; McNicoll, N.; Febbraio, M.; Servant, M.; Marleau, S.; Silverstein, R.; Ong, H. Identification of the growth hormone-releasing peptide binding site in CD36: a photoaffinity cross-linking study Biochem. J. 2004, 382, 417-424
    • (2004) Biochem. J. , vol.382 , pp. 417-424
    • Demers, A.1    McNicoll, N.2    Febbraio, M.3    Servant, M.4    Marleau, S.5    Silverstein, R.6    Ong, H.7
  • 12
    • 34548482011 scopus 로고    scopus 로고
    • CD36: Implications in Cardiovascular Disease
    • Febbraio, M.; Silverstein, R. L. CD36: Implications in Cardiovascular Disease Int. J. Biochem. Cell Biol. 2007, 39 (11) 2012-2030
    • (2007) Int. J. Biochem. Cell Biol. , vol.39 , Issue.11 , pp. 2012-2030
    • Febbraio, M.1    Silverstein, R.L.2
  • 16
    • 0029902950 scopus 로고    scopus 로고
    • Theoretical study of the structure and rotational flexibility of diacylhydrazines: Implications for the structure of nonsteroidal ecdysone agonists and azapeptides
    • Reynolds, C. H.; Hormann, R. E. Theoretical study of the structure and rotational flexibility of diacylhydrazines: implications for the structure of nonsteroidal ecdysone agonists and azapeptides J. Am. Chem. Soc. 1996, 118, 9395-9401
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9395-9401
    • Reynolds, C.H.1    Hormann, R.E.2
  • 17
    • 0037048621 scopus 로고    scopus 로고
    • A theoretical study of conformational properties of N -methyl azapeptide derivatives
    • Lee, H.-J.; Song, J.-W.; Choi, Y.-S.; Park, H.-M.; Lee, K.-B. A theoretical study of conformational properties of N -methyl azapeptide derivatives J. Am. Chem. Soc. 2002, 124, 11881-11893
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 11881-11893
    • Lee, H.-J.1    Song, J.-W.2    Choi, Y.-S.3    Park, H.-M.4    Lee, K.-B.5
  • 18
    • 0030739480 scopus 로고    scopus 로고
    • Aza-peptides., I. I. X-Ray structures of aza-alanine and aza-asparagine-containing peptides
    • André, F.; Boussard, G.; Bayeul, D.; Didierjean, C.; Aubry, A.; Marraud, M.; Aza-peptides., I. I. X-Ray structures of aza-alanine and aza-asparagine-containing peptides J. Peptide Res. 1997, 49, 556-562
    • (1997) J. Peptide Res. , vol.49 , pp. 556-562
    • André, F.1    Boussard, G.2    Bayeul, D.3    Didierjean, C.4    Aubry, A.5    Marraud, M.6
  • 19
    • 0030773550 scopus 로고    scopus 로고
    • Aza-peptides. III. Experimental structural analysis of aza-alanine and aza-asparagine-containing peptides
    • André, F.; Vicherat, A.; Boussard, G.; Aubry, A.; Marraud, M. Aza-peptides. III. Experimental structural analysis of aza-alanine and aza-asparagine-containing peptides J. Peptide Res. 1997, 50, 372-381
    • (1997) J. Peptide Res. , vol.50 , pp. 372-381
    • André, F.1    Vicherat, A.2    Boussard, G.3    Aubry, A.4    Marraud, M.5
  • 20
    • 0030572484 scopus 로고    scopus 로고
    • An active-site titrant for chymotrypsin, and evidence that azapeptide esters are less susceptible to nucleophilic attack than ordinary esters
    • Gassman, J. M.; Magrath, J. An active-site titrant for chymotrypsin, and evidence that azapeptide esters are less susceptible to nucleophilic attack than ordinary esters Bioorg. Med. Chem. Lett. 1996, 6 (15) 1771-1774
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , Issue.15 , pp. 1771-1774
    • Gassman, J.M.1    Magrath, J.2
  • 21
    • 28244437082 scopus 로고    scopus 로고
    • Aza-amino acid scanning of secondary structure suited for solid-phase peptide synthesis with Fmoc chemistry and aza-amino acids with heteroatomic side chains
    • Boeglin, D.; Lubell, W. D. Aza-amino acid scanning of secondary structure suited for solid-phase peptide synthesis with Fmoc chemistry and aza-amino acids with heteroatomic side chains J. Comb. Chem. 2005, 7, 864-878
    • (2005) J. Comb. Chem. , vol.7 , pp. 864-878
    • Boeglin, D.1    Lubell, W.D.2
  • 22
    • 0018132888 scopus 로고
    • Synthesis and biological activity of highly active α-aza analogues of luliberin
    • Dutta, A. S.; Furr, B. J. A.; Giles, M. B.; Valcaccia, B. Synthesis and biological activity of highly active α-aza analogues of luliberin J. Med. Chem. 1978, 21 (10) 1018-1024
    • (1978) J. Med. Chem. , vol.21 , Issue.10 , pp. 1018-1024
    • Dutta, A.S.1    Furr, B.J.A.2    Giles, M.B.3    Valcaccia, B.4
  • 24
    • 0029665670 scopus 로고    scopus 로고
    • From Poor Substrates to Good Inhibitors: Design of Inhibitors for Serine and Thiol Proteases
    • Baggio, R.; Shi, Y.-Q.; Wu, Y.-Q.; Abeles, R. H. From Poor Substrates to Good Inhibitors: Design of Inhibitors for Serine and Thiol Proteases Biochemistry 1996, 35 (11) 3351-3353
    • (1996) Biochemistry , vol.35 , Issue.11 , pp. 3351-3353
    • Baggio, R.1    Shi, Y.-Q.2    Wu, Y.-Q.3    Abeles, R.H.4
  • 25
    • 0026494941 scopus 로고
    • Cysteine Protease Inhibition by Azapeptide Esters
    • Magrath, J.; Abeles, R. H. Cysteine Protease Inhibition by Azapeptide Esters J. Med. Chem. 1992, 35, 4279-4283
    • (1992) J. Med. Chem. , vol.35 , pp. 4279-4283
    • Magrath, J.1    Abeles, R.H.2
  • 26
    • 33947674064 scopus 로고    scopus 로고
    • Calcitonin gene-related peptide analogues with aza and indolizidinone amino acid residues reveal conformational requirements for antagonist activity at the human calcitonin gene-related peptide 1 receptor
    • Boeglin, D.; Hamdan, F. F.; Melendez, R. E.; Cluzeau, J.; Laperriere, A.; Héroux, M.; Bouvier, M.; Lubell, W. D. Calcitonin gene-related peptide analogues with aza and indolizidinone amino acid residues reveal conformational requirements for antagonist activity at the human calcitonin gene-related peptide 1 receptor J. Med. Chem. 2007, 50, 1401-1408
    • (2007) J. Med. Chem. , vol.50 , pp. 1401-1408
    • Boeglin, D.1    Hamdan, F.F.2    Melendez, R.E.3    Cluzeau, J.4    Laperriere, A.5    Héroux, M.6    Bouvier, M.7    Lubell, W.D.8
  • 29
    • 80051580579 scopus 로고    scopus 로고
    • Structure-Activity Relationships of GHRP-6 Azapeptide Ligands of the CD36 Scavenger Receptor by Solid-Phase Submonomer Azapeptide Synthesis
    • Sabatino, D.; Proulx, C.; Pohankova, P.; Ong, H.; Lubell, W. D. Structure-Activity Relationships of GHRP-6 Azapeptide Ligands of the CD36 Scavenger Receptor by Solid-Phase Submonomer Azapeptide Synthesis J. Am. Chem. Soc. 2011, 133, 12493-12506
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 12493-12506
    • Sabatino, D.1    Proulx, C.2    Pohankova, P.3    Ong, H.4    Lubell, W.D.5
  • 30
    • 0032421379 scopus 로고    scopus 로고
    • A Quantitative Assay for Angiogenesis of Cultured Choroidal Tissues in Streptozotocin-Diabetic Wistar and Spontaneously Diabetic GK Rats
    • Kobayashi, S.; Fukuta, M.; Kontani, H.; Yanagita, S.; Kimura, I. A Quantitative Assay for Angiogenesis of Cultured Choroidal Tissues in Streptozotocin-Diabetic Wistar and Spontaneously Diabetic GK Rats Jpn. J. Pharmacol. 1998, 78, 471-478
    • (1998) Jpn. J. Pharmacol. , vol.78 , pp. 471-478
    • Kobayashi, S.1    Fukuta, M.2    Kontani, H.3    Yanagita, S.4    Kimura, I.5
  • 33
    • 79955564633 scopus 로고    scopus 로고
    • Microwave-Assisted Solid-Phase Aza-peptide Synthesis: Aza Scan of a PKB/Akt Inhibitor Using Aza-arginine and Aza-proline Precursors
    • Freeman, N. S.; Tal-Gan, Y.; Klein, S.; Levitzki, A.; Gilon, C. Microwave-Assisted Solid-Phase Aza-peptide Synthesis: Aza Scan of a PKB/Akt Inhibitor Using Aza-arginine and Aza-proline Precursors J. Org. Chem. 2011, 76, 3078-3085
    • (2011) J. Org. Chem. , vol.76 , pp. 3078-3085
    • Freeman, N.S.1    Tal-Gan, Y.2    Klein, S.3    Levitzki, A.4    Gilon, C.5
  • 41
    • 0027624391 scopus 로고
    • Crystal state conformation of three azapeptides containing the azaproline residue, a β-turn regulator
    • Lecoq, A.; Boussard, G.; Marraud, M.; Aubry, A. Crystal state conformation of three azapeptides containing the azaproline residue, a β-turn regulator Biopolymers 1993, 33, 1051-1059
    • (1993) Biopolymers , vol.33 , pp. 1051-1059
    • Lecoq, A.1    Boussard, G.2    Marraud, M.3    Aubry, A.4
  • 42
    • 0026806775 scopus 로고
    • The couple Pro/AzaPro: A means of β-turn formation control synthesis and conformation of two aza-pro-containing dipeptides
    • Lecoq, A.; Boussard, G.; Marraud, M. The couple Pro/AzaPro: a means of β-turn formation control synthesis and conformation of two aza-pro-containing dipeptides Tetrahedron Lett. 1992, 33 (36) 5209-5212
    • (1992) Tetrahedron Lett. , vol.33 , Issue.36 , pp. 5209-5212
    • Lecoq, A.1    Boussard, G.2    Marraud, M.3
  • 44
    • 0018267874 scopus 로고
    • Circular dichroism of β turns in peptides and proteins
    • Bush, C. A.; Sarkar, S. K.; Kopple, K. D. Circular dichroism of β turns in peptides and proteins Biochemistry 1978, 17, 4951-4954
    • (1978) Biochemistry , vol.17 , pp. 4951-4954
    • Bush, C.A.1    Sarkar, S.K.2    Kopple, K.D.3
  • 45
    • 0033214140 scopus 로고    scopus 로고
    • Novel solid-phase synthesis of azapeptides and azapeptoides via Fmoc-strategy and its application in the synthesis of RGD-mimetics
    • Gibson, C.; Goodman, S. L.; Hahn, D.; Hölzemann, G.; Kessler, H. Novel solid-phase synthesis of azapeptides and azapeptoides via Fmoc-strategy and its application in the synthesis of RGD-mimetics J. Org. Chem. 1999, 64, 7388-7394
    • (1999) J. Org. Chem. , vol.64 , pp. 7388-7394
    • Gibson, C.1    Goodman, S.L.2    Hahn, D.3    Hölzemann, G.4    Kessler, H.5
  • 46
    • 33947091567 scopus 로고
    • The 9-Fluorenylmethoxycarbonyl Amino-Protecting Group
    • Carpino, L. A.; Han, J. Y. The 9-Fluorenylmethoxycarbonyl Amino-Protecting Group J. Org. Chem. 1972, 37, 3404-3409
    • (1972) J. Org. Chem. , vol.37 , pp. 3404-3409
    • Carpino, L.A.1    Han, J.Y.2
  • 47
    • 0037419780 scopus 로고    scopus 로고
    • Impact of Azaproline on Amide Cis-Trans Isomerism: Conformational Analyses and NMR Studies of Model Peptides Including TRH Analogues
    • Zhang, W.-J.; Berglund, A.; Kao, J. L.-F.; Couty, J.-P.; Gershengorn, M. C.; Marshall, G. R. Impact of Azaproline on Amide Cis-Trans Isomerism: Conformational Analyses and NMR Studies of Model Peptides Including TRH Analogues J. Am. Chem. Soc. 2003, 125, 1221-1235
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 1221-1235
    • Zhang, W.-J.1    Berglund, A.2    Kao, J.L.-F.3    Couty, J.-P.4    Gershengorn, M.C.5    Marshall, G.R.6
  • 48
    • 0014643560 scopus 로고
    • Rate of calcium binding and uptake in normal animal and failing human cardiac muscle: Membrane vesicles (relaxing system) and mitochondria
    • Harigaya, S.; Schwartz, A. Rate of calcium binding and uptake in normal animal and failing human cardiac muscle: membrane vesicles (relaxing system) and mitochondria Circ. Res. 1969, 25, 781-794
    • (1969) Circ. Res. , vol.25 , pp. 781-794
    • Harigaya, S.1    Schwartz, A.2


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