메뉴 건너뛰기




Volumn 63, Issue 3, 2004, Pages 270-278

Synthesis and activity of the melanocortin Xaa-D-Phe-Arg-Trp-NH2 tetrapeptides with amide bond modifications

Author keywords

Agouti; Melanotropin; N methylation; Obesity; Reduction

Indexed keywords

AMIDE; HISTIDYL DEXTRO PHENYLALANYLARGINYLTRYPTOPHANAMIDE; HORMONE RECEPTOR AFFECTING AGENT; MELANOCORTIN; MELANOCORTIN 1 RECEPTOR; MELANOCORTIN 3 RECEPTOR; MELANOCORTIN 4 RECEPTOR; MELANOCORTIN 5 RECEPTOR; MELANOCORTIN RECEPTOR BLOCKING AGENT; MELANOCORTIN RECEPTOR STIMULATING AGENT; PHENYLALANYL DEXTRO PHENYLALANYLARGINYLTRYPTOPHANAMIDE; TETRAPEPTIDE; UNCLASSIFIED DRUG;

EID: 1942438119     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.2004.00137.x     Document Type: Article
Times cited : (18)

References (49)
  • 1
    • 0026800892 scopus 로고
    • The cloning of a family of genes that encode the melanocortin receptors
    • Mountjoy, K.G., Robbins, L.S., Mortrud, M.T. & Cone, R.D. (1992) The cloning of a family of genes that encode the melanocortin receptors. Science 257, 1248-1251.
    • (1992) Science , vol.257 , pp. 1248-1251
    • Mountjoy, K.G.1    Robbins, L.S.2    Mortrud, M.T.3    Cone, R.D.4
  • 7
    • 0026731363 scopus 로고
    • Molecular cloning and expression of the human melanocyte stimulating hormone receptor cDNA
    • Chhajlani, V. & Wikberg, J.E.S. (1992) Molecular cloning and expression of the human melanocyte stimulating hormone receptor cDNA. FEBS Lett. 309, 417-420.
    • (1992) FEBS Lett. , vol.309 , pp. 417-420
    • Chhajlani, V.1    Wikberg, J.E.S.2
  • 9
    • 0019268826 scopus 로고
    • Structure and biosynthesis of pro-ACTH/endorphin and related peptides
    • Eipper, B.A. & Mains, R.E. (1980) Structure and biosynthesis of pro-ACTH/endorphin and related peptides. Endocrin. Rev. 1, 1-26.
    • (1980) Endocrin. Rev. , vol.1 , pp. 1-26
    • Eipper, B.A.1    Mains, R.E.2
  • 10
    • 0023959725 scopus 로고
    • Proopiomelanocortin processing in the pituitary, central nervous system and peripheral tissues
    • Smith, A.I. & Funder, J.W. (1988) Proopiomelanocortin processing in the pituitary, central nervous system and peripheral tissues. Endocrin. Rev. 9, 159-179.
    • (1988) Endocrin. Rev. , vol.9 , pp. 159-179
    • Smith, A.I.1    Funder, J.W.2
  • 17
    • 0037294189 scopus 로고    scopus 로고
    • Structure-activity relationship of linear peptide Bu-His(6)-D-Phe(7)- Arg(8)-Trp(9)-Gly(10)-NH(2) at the human melanocortin-1 and -4 receptors: D-Phe(7) and Trp(9) substitution
    • Danho, W., Swistok, J., Wai-Hing Cheung, A., Kurylko, G., Franco, L., Chu, X.J., Chen, L. & Yagaloff, K. (2003) Structure-activity relationship of linear peptide Bu-His(6)-D-Phe(7)-Arg(8)-Trp(9)-Gly(10)-NH(2) at the human melanocortin-1 and -4 receptors: D-Phe(7) and Trp(9) substitution. Bioorg. Med. Chem. Lett. 13, 649-652.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 649-652
    • Danho, W.1    Swistok, J.2    Wai-Hing Cheung, A.3    Kurylko, G.4    Franco, L.5    Chu, X.J.6    Chen, L.7    Yagaloff, K.8
  • 18
    • 17444451027 scopus 로고    scopus 로고
    • Structure-activity relationship of linear peptide Bu-His-D-Phe-Arg-Trp- Gly-NH(2) at the human melanocortin-1 and -4 receptors: Histidine substitution
    • Cheung, A.W., Danho, W., Swistok, J., Qi, L., Kurylko, G., Rowan, K., Yeon, M., Franco, L., Chu, X.J., Chen, L. & Yagaloff, K. (2003) Structure-activity relationship of linear peptide Bu-His-D-Phe-Arg-Trp-Gly-NH(2) at the human melanocortin-1 and -4 receptors: histidine substitution. Bioorg. Med. Chem. Lett. 13, 133-137.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 133-137
    • Cheung, A.W.1    Danho, W.2    Swistok, J.3    Qi, L.4    Kurylko, G.5    Rowan, K.6    Yeon, M.7    Franco, L.8    Chu, X.J.9    Chen, L.10    Yagaloff, K.11
  • 19
    • 0037009186 scopus 로고    scopus 로고
    • Structure-activity relationship of linear peptide Bu-His-D-Phe-Arg-Trp- Gly-NH(2) at the human melanocortin-1 and -4 receptors: Arginine substitution
    • Cheung, A., Danho, W., Swistok, J., Qi, L., Kurylko, G., Franco, L., Yagaloff, K. & Chen, L. (2002) Structure-activity relationship of linear peptide Bu-His-D-Phe-Arg-Trp-Gly-NH(2) at the human melanocortin-1 and -4 receptors: arginine substitution. Bioorg. Med. Chem. Lett. 12, 2407-2410.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 2407-2410
    • Cheung, A.1    Danho, W.2    Swistok, J.3    Qi, L.4    Kurylko, G.5    Franco, L.6    Yagaloff, K.7    Chen, L.8
  • 20
    • 0037811382 scopus 로고    scopus 로고
    • Subnanomolar hMCiR agonists by end-capping of the melanocortin tetrapeptide His-D-Phe-Arg-Trp-NH(2)
    • Koikov, L.N., Ebetino, F.H., Solinsky, M.G., Cross-Doersen, D. & Knittel, J.J. (2003) Subnanomolar hMCiR agonists by end-capping of the melanocortin tetrapeptide His-D-Phe-Arg-Trp-NH(2). Bioorg. Med. Chem. Lett. 13, 2647-2650.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 2647-2650
    • Koikov, L.N.1    Ebetino, F.H.2    Solinsky, M.G.3    Cross-Doersen, D.4    Knittel, J.J.5
  • 21
    • 0000788606 scopus 로고
    • Peptide backbone modifications: A structure-activity analysis of peptides containing amide bond surrogates
    • Spatola, A.F. (1983) Peptide backbone modifications: a structure-activity analysis of peptides containing amide bond surrogates. Chem. Biochem. Amino Acids Pept. Proteins 267-357.
    • (1983) Chem. Biochem. Amino Acids Pept. Proteins , pp. 267-357
    • Spatola, A.F.1
  • 22
    • 33947091567 scopus 로고
    • The 9-fluorenylmethyloxycarbonyl amino-protecting group
    • Carpino, L.A. & Han, G.Y. (1972) The 9-fluorenylmethyloxycarbonyl amino-protecting group. J. Org. Chem. 37, 3404-3409.
    • (1972) J. Org. Chem. , vol.37 , pp. 3404-3409
    • Carpino, L.A.1    Han, G.Y.2
  • 23
    • 0018085515 scopus 로고
    • Solid-phase peptide synthesis using mild base cleavage of Na-fluorenylmethyloxycarbonyl amino acids, exemplified by a synthesis of dihydrosomatostatin
    • Chang, C. & Meienhofer, J. (1978) Solid-phase peptide synthesis using mild base cleavage of Na-fluorenylmethyloxycarbonyl amino acids, exemplified by a synthesis of dihydrosomatostatin. Int. J. Pept. Protein Res. 11, 246-249.
    • (1978) Int. J. Pept. Protein Res. , vol.11 , pp. 246-249
    • Chang, C.1    Meienhofer, J.2
  • 24
    • 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. (1970) Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 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
  • 25
    • 0030936620 scopus 로고    scopus 로고
    • Site-selective N-methylation of peptides on solid support
    • Miller, S.C. & Scanlan, T.S. (1997) Site-selective N-methylation of peptides on solid support. J. Am. Chem. Soc. 119, 2301-2302.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 2301-2302
    • Miller, S.C.1    Scanlan, T.S.2
  • 26
    • 0032565117 scopus 로고    scopus 로고
    • oNBS-SPPS: A new method for solid-phase peptide synthesis
    • Miller, S.C. & Scanlan, T.S. (1998) oNBS-SPPS: a new method for solid-phase peptide synthesis. J. Am. Chem. Soc. 120, 2690-2691.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 2690-2691
    • Miller, S.C.1    Scanlan, T.S.2
  • 27
    • 0033525195 scopus 로고    scopus 로고
    • Mild oxidative cleavage of borane-amine adducts from amide reductions: Efficient solution- and solid-phase synthesis of N-alkyl amino acids and chiral oligoamines
    • Hall, D.G., Laplante, C., Manku, S. & Nagendran, J. (1999) Mild oxidative cleavage of borane-amine adducts from amide reductions: efficient solution-and solid-phase synthesis of N-alkyl amino acids and chiral oligoamines. J. Org. Chem. 64, 698-699.
    • (1999) J. Org. Chem. , vol.64 , pp. 698-699
    • Hall, D.G.1    Laplante, C.2    Manku, S.3    Nagendran, J.4
  • 28
    • 0035830582 scopus 로고    scopus 로고
    • A mild and general solid-phase method for the synthesis of chiral polyamines. Solution studies on the cleavage of borane-amine intermediates from the reduction of secondary amides
    • Manku, S., Laplante, C., Kopac, D., Chan, T. & Hall, D.G. (2001) A mild and general solid-phase method for the synthesis of chiral polyamines. Solution studies on the cleavage of borane-amine intermediates from the reduction of secondary amides. J. Org. Chem. 66, 874-885.
    • (2001) J. Org. Chem. , vol.66 , pp. 874-885
    • Manku, S.1    Laplante, C.2    Kopac, D.3    Chan, T.4    Hall, D.G.5
  • 29
    • 0031767227 scopus 로고    scopus 로고
    • Solid-phase synthesis of trisubstituted bicyclic guanidines via cyclization of reduced N-acylated dipeptides
    • Ostresh, J.M., Schoner, C.C., Hamashin, V.T., Nefzi, A., Meyer, J.P. & Houghten, R.A. (1998) Solid-phase synthesis of trisubstituted bicyclic guanidines via cyclization of reduced N-acylated dipeptides. J. Org. Chem. 63, 8622-8613.
    • (1998) J. Org. Chem. , vol.63 , pp. 8622-18613
    • Ostresh, J.M.1    Schoner, C.C.2    Hamashin, V.T.3    Nefzi, A.4    Meyer, J.P.5    Houghten, R.A.6
  • 30
    • 0028947365 scopus 로고
    • A colorimetric assay for measuring activation of Gs- and Gq-coupled signaling pathways
    • Chen, W., Shields, T.S., Stork, P.J.S. & Cone, R.D. (1995) A colorimetric assay for measuring activation of Gs-and Gq-coupled signaling pathways. Anal. Biochem. 116, 349-354.
    • (1995) Anal. Biochem. , vol.116 , pp. 349-354
    • Chen, W.1    Shields, T.S.2    Stork, P.J.S.3    Cone, R.D.4
  • 31
    • 0035927436 scopus 로고    scopus 로고
    • Characterization of melanocortin NDP-MSH agonist peptide fragments at the mouse central and peripheral melanocortin receptors
    • Haskell-Luevano, C., Holder, J.R., Monck, E.K. & Bauzo, R.M. (2001) Characterization of melanocortin NDP-MSH agonist peptide fragments at the mouse central and peripheral melanocortin receptors. J. Med. Chem. 44, 2247-2252.
    • (2001) J. Med. Chem. , vol.44 , pp. 2247-2252
    • Haskell-Luevano, C.1    Holder, J.R.2    Monck, E.K.3    Bauzo, R.M.4
  • 32
    • 0342993927 scopus 로고    scopus 로고
    • A reductive alkylation procedure applicable to both solution- and solid-phase syntheses of secondary amines
    • Szardenings, A.K., Burkoth, T.S., Look, G.C. & Campbell, D.A. (1996) A reductive alkylation procedure applicable to both solution-and solid-phase syntheses of secondary amines. J. Org. Chem. 61, 6720-6722.
    • (1996) J. Org. Chem. , vol.61 , pp. 6720-6722
    • Szardenings, A.K.1    Burkoth, T.S.2    Look, G.C.3    Campbell, D.A.4
  • 33
    • 0000844109 scopus 로고    scopus 로고
    • Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures(1)
    • Abdel-Magid, A.F., Carson, K.G., Harris, B.D., Maryanoff, C.A. & Shah, R.D. (1996) Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures(1). J. Org. Chem. 61, 3849-3862.
    • (1996) J. Org. Chem. , vol.61 , pp. 3849-3862
    • Abdel-Magid, A.F.1    Carson, K.G.2    Harris, B.D.3    Maryanoff, C.A.4    Shah, R.D.5
  • 34
    • 0000878731 scopus 로고
    • N-methylamino acids in peptide-synthesis. 7. Studies on enantiomeric purity of N-methylamino acids prepared by various procedures
    • Cheung, S.T. & Benoiton, N.L. (1977) N-methylamino acids in peptide-synthesis. 7. Studies on enantiomeric purity of N-methylamino acids prepared by various procedures. Can. J. Chem.-Rev. Can. Chim. 55, 916-921.
    • (1977) Can. J. Chem.-Rev. Can. Chim. , vol.55 , pp. 916-921
    • Cheung, S.T.1    Benoiton, N.L.2
  • 35
    • 0001023731 scopus 로고
    • N-methylamino acids in peptide synthesis. 2. New synthesis of N-benzyloxycarbonyl,N-methylamino acids
    • McDermot JR & Benoiton, N.L. (1973) N-methylamino acids in peptide synthesis. 2. New synthesis of N-benzyloxycarbonyl,N-methylamino acids. Can. J. Chem.-Rev. Can. Chim. 51, 1915-1919.
    • (1973) Can. J. Chem.-Rev. Can. Chim. , vol.51 , pp. 1915-1919
    • McDermot, J.R.1    Benoiton, N.L.2
  • 36
    • 0032485334 scopus 로고    scopus 로고
    • Site-specific N-alkylation of peptides on the solid phase
    • Reichwein, J.F. & Liskamp, R.M.J. (1998) Site-specific N-alkylation of peptides on the solid phase. Tetrahedron Lett. 39, 1243-1246.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1243-1246
    • Reichwein, J.F.1    Liskamp, R.M.J.2
  • 37
    • 0035902222 scopus 로고    scopus 로고
    • Direct mono-N-methylation of solid-supported amino acids: A useful application of the Matteson rearrangement of α-aminoalkylboronic esters
    • Laplante, C. & Hall, D.G. (2001) Direct mono-N-methylation of solid-supported amino acids: a useful application of the Matteson rearrangement of α-aminoalkylboronic esters. Org. Lett. 3, 1487-1490.
    • (2001) Org. Lett. , vol.3 , pp. 1487-1490
    • Laplante, C.1    Hall, D.G.2
  • 38
    • 0035842504 scopus 로고    scopus 로고
    • Solid-phase synthesis of bis-cyclic guanidines from tripeptides
    • Acharya, A.N., Ostresh, J.M. & Houghten, R.A. (2001) Solid-phase synthesis of bis-cyclic guanidines from tripeptides. Tetrahedron 57, 9911-9914.
    • (2001) Tetrahedron , vol.57 , pp. 9911-9914
    • Acharya, A.N.1    Ostresh, J.M.2    Houghten, R.A.3
  • 39
    • 0032497397 scopus 로고    scopus 로고
    • Combinatorial chemistry: From peptides and peptidomimetics to small organic and heterocyclic compounds
    • Nefzi, A., Dooley, C., Ostresh, J.M. & Houghten, R.A. (1998) Combinatorial chemistry: from peptides and peptidomimetics to small organic and heterocyclic compounds. Bioorg. Med. Chem. Lett. 8, 2273-2278.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 2273-2278
    • Nefzi, A.1    Dooley, C.2    Ostresh, J.M.3    Houghten, R.A.4
  • 40
    • 0035682508 scopus 로고    scopus 로고
    • Solid phase synthesis of mixture-based acyclic and heterocyclic small molecule combinatorial libraries from resin-bound polyamides
    • Nefzi, A., Ostresh, J.M. & Houghten, R.A. (2001) Solid phase synthesis of mixture-based acyclic and heterocyclic small molecule combinatorial libraries from resin-bound polyamides. Biopolymers 60, 212-219.
    • (2001) Biopolymers , vol.60 , pp. 212-219
    • Nefzi, A.1    Ostresh, J.M.2    Houghten, R.A.3
  • 41
    • 0001262709 scopus 로고    scopus 로고
    • Palladium and Raney nickel catalyzed methanolic cleavage of stable borane-amine complexes
    • Couturier, M., Tucker, J.L., Andresen, B.M., Dube, P. & Negri, J.T. (2001) Palladium and Raney nickel catalyzed methanolic cleavage of stable borane-amine complexes. Org. Lett. 3, 465-467.
    • (2001) Org. Lett. , vol.3 , pp. 465-467
    • Couturier, M.1    Tucker, J.L.2    Andresen, B.M.3    Dube, P.4    Negri, J.T.5
  • 42
    • 0033576637 scopus 로고    scopus 로고
    • Rolling loop scan: An approach featuring ring-closing metathesis for generating libraries of peptides with molecular shapes mimicking bioactive conformations or local folding of peptides and proteins
    • Reichwein, J.F., Wels, B., Kruijtzer, J.A.W., Versluis, C. & Liskamp, R.M.J. (1999) Rolling loop scan: an approach featuring ring-closing metathesis for generating libraries of peptides with molecular shapes mimicking bioactive conformations or local folding of peptides and proteins. Angew. Chem. Int. Ed. 38, 3684-3687.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 3684-3687
    • Reichwein, J.F.1    Wels, B.2    Kruijtzer, J.A.W.3    Versluis, C.4    Liskamp, R.M.J.5
  • 43
    • 0024551431 scopus 로고
    • Design of a new class of superpotent cyclic α-melanotropins based on quenched dynamic stimulations
    • Al-Obeidi, F., Hadley, M.E., Pettitt, B.M. & Hruby, V.J. (1989) Design of a new class of superpotent cyclic α-melanotropins based on quenched dynamic stimulations. J. Am. Chem. Soc. 111, 3413-3416.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 3413-3416
    • Al-Obeidi, F.1    Hadley, M.E.2    Pettitt, B.M.3    Hruby, V.J.4
  • 45
    • 0023934137 scopus 로고
    • Probing peptide backbone function in bombesin - A reduced peptide-bond analog with potent and specific receptor antagonist activity
    • Coy, D.H., Heinzerian, P., Jiang, N.Y., Sasaki, Y., Taylor, J., Moreau, J.P., Wolfrey, W.T., Gardner, J.D. & Jensen, R.T. (1988) Probing peptide backbone function in bombesin - a reduced peptide-bond analog with potent and specific receptor antagonist activity. J. Biol. Chem. 163, 5056-5060.
    • (1988) J. Biol. Chem. , vol.163 , pp. 5056-5060
    • Coy, D.H.1    Heinzerian, P.2    Jiang, N.Y.3    Sasaki, Y.4    Taylor, J.5    Moreau, J.P.6    Wolfrey, W.T.7    Gardner, J.D.8    Jensen, R.T.9
  • 46
    • 0024440710 scopus 로고
    • Reduced peptide-bond pseudopeptide analogs of substance-P - A new class of substance-P receptor antagonists with enhanced specificity
    • Qian, J.M., Coy, D.H., Jiang, N.Y., Gardner, J.D. & Jensen, R.T. (1989) Reduced peptide-bond pseudopeptide analogs of substance-P - a new class of substance-P receptor antagonists with enhanced specificity. J. Biol. Chem. 164, 16667-16671.
    • (1989) J. Biol. Chem. , vol.164 , pp. 16667-16671
    • Qian, J.M.1    Coy, D.H.2    Jiang, N.Y.3    Gardner, J.D.4    Jensen, R.T.5
  • 47
    • 0025960524 scopus 로고
    • Reduced peptide-bond pseudopeptide analogs of secretin - A new class of secretin receptor antagonists
    • Haffar, B.M., Hocart, S.J., Coy, D.H., Mantey, S., Chiang, H.C.V. & Jensen, R.T. (1991) Reduced peptide-bond pseudopeptide analogs of secretin - a new class of secretin receptor antagonists. J. Biol. Chem. 266, 316-322.
    • (1991) J. Biol. Chem. , vol.266 , pp. 316-322
    • Haffar, B.M.1    Hocart, S.J.2    Coy, D.H.3    Mantey, S.4    Chiang, H.C.V.5    Jensen, R.T.6
  • 48
    • 0037041182 scopus 로고    scopus 로고
    • Reductive amination products containing naphthalene and indole moieties bind to melanocortin receptors
    • Mutulis, F., Mutule, I., Lapins, M. & Wikberg, J.E. (2002) Reductive amination products containing naphthalene and indole moieties bind to melanocortin receptors. Bioorg. Med. Chem. Lett. 12, 1035-1038.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 1035-1038
    • Mutulis, F.1    Mutule, I.2    Lapins, M.3    Wikberg, J.E.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.