Structure-activity relationships (SAR) of melanocortin and agouti-related (AGRP) peptides

Advances in Experimental Medicine and Biology

Volumn 681, Issue , 2010, Pages 1-18

  Singh, Anamika ^b   Haslach, Erica M ^b   Haskell Luevano, Carrie ^a  

^a UNIVERSITY OF FLORIDA   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

AGOUTI RELATED PROTEIN; ALPHA INTERMEDIN; AMINO TERMINAL TELOPEPTIDE; BETA INTERMEDIN; CHIMERIC PROTEIN; CORTICOTROPIN; CYCLOPEPTIDE; GAMMA INTERMEDIN; GUANIDINE DERIVATIVE; MELANOCORTIN; MELANOCORTIN 1 RECEPTOR; MELANOCORTIN 2 RECEPTOR; MELANOCORTIN 3 RECEPTOR; MELANOCORTIN 4 RECEPTOR; MELANOCORTIN 4 RECEPTOR AGONIST; MELANOCORTIN 5 RECEPTOR; MELANOCORTIN RECEPTOR AGONIST; N ACETYL ALPHA INTERMEDIN[4-10]CYCLO[4 NORLEUCINE 5 ASPARTIC ACID 7 [3 (2 NAPHTHYL)ALANINE] 10 LYSINAMIDE]; TETRAPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ENZYME ACTIVITY; HUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION; PROTEIN INTERACTION; PROTEIN METHYLATION; PROTEIN STRUCTURE; STRUCTURE ACTIVITY RELATION;

AGOUTI-RELATED PROTEIN; AMINO ACID SEQUENCE; ANIMALS; DRUG DISCOVERY; HUMANS; MELANOCORTINS; MOLECULAR SEQUENCE DATA; PEPTIDE FRAGMENTS; STRUCTURE-ACTIVITY RELATIONSHIP;

AGOUTI;

EID: 79959564021     PISSN: 00652598     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-4419-6354-3_1     Document Type: Article

References (95)

1. Chhajlani V, Wikberg JES. Molecular cloning and expression of the human melanocyte stimulating hormone receptor cDNA. FEBS Lett 1992; 309(3):417-420.
2. Mountjoy KG, Robbins LS, Mortrud MT et al. The cloning of a family of genes that encode the melanocortin receptors. Science 1992; 257:1248-1251.
3. Roselli-Rehfuss L, Mountjoy KG, Robbins LS et al. Identification of a receptor for g melanotropin and other proopiomelanocortin peptides in the hypothalamus and limbic system. Proc Natl Acad Sci USA 1993; 90:8856-8860. (Pubitemid 23306409)
4. Mountjoy KG, Mortrud MT, Low MJ et al. Localization of the melanocortin-4 receptor (MC4-R) in neuroendocrine and autonomic control circuits in the brain. Mol Endo 1994; 8:1298-1308. (Pubitemid 24335073)
5. Gantz I, Konda Y, Tashiro T et al. Molecular cloning of a novel melanocortin receptor. J Biol Chem 1993; 268(11):8246-8250. (Pubitemid 23120413)
6. Gantz I, Miwa H, Konda Y et al. Molecular cloning, expression and gene localization of a fourth melanocortin receptor. J Biol Chem 1993; 268(20):15174-15179. (Pubitemid 23206671)
7. Gantz I, Shimoto Y, Konda Y et al. Molecular cloning, expression and characterization of a fifth melanocortin receptor. Biochem Biophys Res Commun 1994; 200(3):1214-1220. (Pubitemid 24181781)
8. Eipper BA, Mains RE. Structure and biosynthesis of Pro-ACTH/Endorphin and related peptides. Endocrin Rev 1980; 1:1-26.
9. Hruby VJ, Wilkes BC, Cody WL et al. Melanotropins: Structural, conformational and biological considerations in the development of superpotent and superprolonged analogs. Peptide Protein Rev 1984; 3:1-64.
10. Haskell-Luevano C, Sawyer TK, Hendrata S et al. Truncation studies of a-melanotropin peptides identifies tripeptide analogues exhibiting prolonged agonist bioactivity. Peptides 1996; 17:995-1002. (Pubitemid 26355326)
11. Lu D, Willard D, Patel IR et al. Agouti protein is an antagonist of the melanocyte-stimulating-hormone receptor. Nature 1994; 371(6500):799-802. (Pubitemid 24333868)
12. Ollmann MM, Wilson BD, Yang Y-K et al. Antagonism of central melanocortin receptors in vitro and in vivo by agouti-related protein. Science 1997; 278:135-138. (Pubitemid 27446294)
13. Chen AS, Marsh DJ, Trumbauer ME et al. Inactivation of the mouse melanocortin-3 receptor results in increased fat mass and reduced lean body mass. Nat Genet 2000; 26(1):97-102.
14. Butler AA, Kesterson RA, Khong K et al. A unique metabolic syndrome causes obesity in the melanocortin- 3 receptor-deficient mouse. Endocrinology 2000; 141(9):3518-3521. (Pubitemid 32269044)
15. Huszar D, Lynch CA, Fairchild-Huntress V et al. Targeted disruption of the melanocortin-4 receptor results in obesity in mice. Cell 1997; 88:131-141. (Pubitemid 27180337)
16. Chen W, Kelly MA, Opitz-Araya X et al. Exocrine gland dysfunction in MC5-R deficient mice: Evidence for coordinated regulation of exocrine gland functions by melanocortin peptides. Cell 1997; 91:789-798. (Pubitemid 28007735)
17. Harrold JA, Widdowson PS, Williams G. b-MSH: A functional ligand that regulated energy homeostasis via hypothalamic MC4-R? Peptides 2003; 24(3):397-405. (Pubitemid 36561211)
18. Eberle AN. The melanotropins: Chemistry, physiology and mechanisms of action. Basel: Karger; 1988.
19. Holder JR, Haskell-Luevano C. Melanocortin Ligands: 30 Years of structure-activity relationship (SAR) studies. Med Res Rev 2004; 24(3):325-356. (Pubitemid 38490035)
20. Irani BG, Holder JR, Todorovic A et al. Progress in the development of melanocortin receptor selective ligands. Curr Pharm Des 2004; 10(28):3443-3479. (Pubitemid 39378328)
21. Sawyer TK, Sanfillippo PJ, Hruby VJ et al. 4-Norleucine, 7-D-Phenylalanine-a-melanocyte-stimulating hormone: A highly potent a-melanotropin with ultra long biological activity. Proc Natl Acad Sci USA 1980; 77:5754-5758. (Pubitemid 11206397)
22. Hruby VJ, Wilkes BC, Hadley ME et al. a-Melanotropin: The minimal active sequence in the frog skin bioassay. J Med Chem 1987; 30:2126-2130. (Pubitemid 18046075)
23. Castrucci AML, Hadley ME, Sawyer TK et al. a-Melanotropin: The minimal active sequence in the lizard skin bioassay. Gen Comp Endocrinol 1989; 73:157-163. (Pubitemid 19032221)
24. Haslach EM, Schaub JW, Haskell-Luevano C. b-Turn secondary structure and melanocortin ligands. Bioorg Med Chem 2009; 17:952-958.
25. Haskell-Luevano C, Rosenquist A, Souers A et al. Compounds that activate the mouse melanocortin-1 receptor identified by screening a small molecule library based upon the b-turn. J Med Chem 1999; 42:4380-4387. (Pubitemid 29504141)
26. Haskell-Luevano C, Holder JR, Monck EK et al. Characterization of melanocortin ndp-msh agonist peptide fragments at the mouse central and peripheral melanocortin receptors. J Med Chem 2001; 44:2247-2252. (Pubitemid 32861783)
27. Sahm UG, Olivier GWJ, Branch SK et al. Synthesis and biological evaluation of a-MSH analogs substituted with alanine. Peptides 1994; 15(7):1297-1302. (Pubitemid 24337087)
28. 2 at the mouse melanocortin receptors: I modifications at the his position. J Med Chem 2002; 45:2801-2810. (Pubitemid 34627650)
29. 2 at the mouse melanocortin receptors: Part 3 modifications at the Arg position. Peptides 2003; 24:73-82. (Pubitemid 36165177)
30. 2 at the mouse melanocortin receptors: Part 4 modifications at the Trp position. J Med Chem 2002; 45:5736-5744. (Pubitemid 35453766)
31. 2 at the mouse melanocortin receptors: Part 2 modifications at the Phe position. J Med Chem 2002; 45:3073-3081. (Pubitemid 34721529)
32. 2 modified at the para position of the benzyl side chain (DPhe): Importance for mouse melanocortin-3 receptor agonist versus antagonist activity. J Med Chem 2008; 51(18):5585-5593.
33. 2 at the arginine side chain with ureas and thioureas. J Pept Res 2005; 66(5):297-307. (Pubitemid 41564317)
34. Danho W, Swistok J, Wai-Hing Cheung A et al. Structure-activity relationship of linear peptide Bu-His(6)-DPhe(7)-Arg(8)-Trp(9)-Gly(10)-NH(2) at the human melanocortin-1 and -4 receptors: DPhe(7) and Trp(9) substitution. Bioorg Med Chem Lett 2003; 13(4):649-652. (Pubitemid 36298460)
35. Cheung AW, Danho W, Swistok J et al. Structure-activity relationship of linear peptide Bu-His-DPhe-Arg-Trp-Gly-NH(2) at the human melanocortin-1 and -4 receptors: Histidine substitution. Bioorg Med Chem Lett 2003; 13(1):133-137. (Pubitemid 35447700)
36. Cheung A, Danho W, Swistok J et al. Structure-activity relationship of linear peptide Bu-His-DPhe-Arg-Trp-Gly-NH(2) at the human melanocortin-1 and -4 receptors: Arginine substitution. Bioorg Med Chem Lett 2002; 12(17):2407-2410. (Pubitemid 34879877)
37. Al-Obeidi F, Castrucci AM, Hadley ME et al. Potent and prolonged acting cyclic lactam analogues of a-melanotropin: Design based on molecular dynamics. J Med Chem 1989; 32:2555-2561. (Pubitemid 20002805)
38. 2 with bulky aromatic amino acids at position 7 show high antagonist potency and selectivity at specific melanocortin receptors. J Med Chem 1995; 38:3454-3461.
39. Al-Obeidi F, Hruby VJ, Yaghoubi N et al. Synthesis and biological activities of fatty acid conjugates of a cyclic lactam a-melanotropin. J Med Chem 1992; 35:118-123.
40. 2 tetrapeptides: Influence of fatty acid chain length on potency and selectivity at the mouse melanocortin receptors and human melanocytes. J Med Chem 2005; 48(9):3328-3336. (Pubitemid 40628051)
41. Chaturvedi DN, Knittel JJ, Hruby VJ et al. Synthesis and biological actions of highly potent and prolonged acting biotin-labeled melanotropins. J Med Chem 1984; 27:1406-1410. (Pubitemid 15200560)
42. 7]-a-MSH. J of Pharmaceutical Sciences 1985; 74:237-240. (Pubitemid 15105908)
43. Bowen M, Monguchi Y, Sankaranarayanan R et al. Design, synthesis and validation of a branched flexible linker for bioactive peptides. J Org Chem 2007; 72:1675-1680. (Pubitemid 46355465)
44. 2 melanocortin tetrapeptides at the melanocortin receptors. Eur J Pharmacol 2003; 462:41-52. (Pubitemid 36183733)
45. Koikov LN, Ebetino FH, Solinsky MG et al. Sub-nanomolar hMC1R agonists by end-capping of the melanocortin tetrapeptide His-D-Phe-Arg-Trp-NH(2). Bioorg Med Chem Lett 2003; 13(16):2647-2650. (Pubitemid 36851541)
46. 2 as a route to hMC4R agonists. Bioorg Med Chem Lett 2004; 14(19):4839-4842. (Pubitemid 39165578)
47. 2]. An additional binding site within the human melanocortin receptor 1? Bioorg Med Chem Lett 2004; 14(15):3997-4000. (Pubitemid 38844412)
48. Haskell-Luevano C, Sawyer TK, Trumpp-Kallmeyer S et al. Three-dimensional molecular models of the hMC1R melanocortin receptor: Complexes with melanotropin peptide agonists. Drug Design and Discovery 1996; 14:197-211.
49. Haskell-Luevano C, Cone RD, Monck EK et al. Structure activity studies of the melanocortin-4 receptor by in vitro mutagenesis: Identification of agouti-related protein (AGRP), melanocortin agonist and synthetic peptide antagonist interaction determinants. Biochemistry 2001; 40(20):6164-6179. (Pubitemid 32466321)
50. Sargent DF, Schwyzer R. Membrane lipid phase as catalyst for peptide-receptor interactions. Proc Natl Acad Sci USA 1986; 83:5774-5778. (Pubitemid 16000594)
51. Yan LZ, Hsiung HM, Heiman M. Structure-activity relationships of α-MSH derived melanocortin-4 receptor peptide agonists. Current Topics in Med Chem 2007; 7:1052-1067. (Pubitemid 47040514)
52. Balse-Srinivasan P, Grieco P, Cai M et al. Structure-activity relationships of novel cyclic α-MSH/ α-MSH hybrid analogues that lead to potent and selective ligands for the human MC3R and human MC5R. J Med Chem 2003; 46(17):3728-3733. (Pubitemid 36992207)
53. Grieco P, Balse-Srinivasan P, Han G et al. Synthesis and biological evaluation on hMC3, hMC4 and hMC5 receptors of g-MSH analogs substituted with L-Alanine. J Pept Res 2002; 59(5):203-210. (Pubitemid 34429933)
54. Grieco P, Balse PM, Weinberg D et al. D-Amino acid scan of g-Melanocyte-stimulating hormone: Importance of Trp(8) on human MC3 receptor selectivity. J Med Chem 2000; 43(26):4998-5002. (Pubitemid 32040975)
55. Balse-Srinivasan P, Grieco P, Cai M et al. Structure-activity relationships of g-MSH analogues at the human melanocortin MC3, MC4 and MC5 receptors. Discovery of highly selective hMC3R, hMC4R and hMC5R analogues. J Med Chem 2003; 46(23):4965-4973. (Pubitemid 37352035)
56. Oosterom J, Burbach JP, Gispen WH et al. Asp10 in Lys-Gamma2-MSH fetermines delective activation of the melanocortin MC3 receptor. Eur J Pharmacol 1998; 354(1):R9-11.
57. Schwyzer R. ACTH: A short introductory review. Ann N Y Acad Sci 1977; 297:3-26. (Pubitemid 8222793)
58. Blake J, Wang KT, Li CH. Adrenocorticotropin. Solid-phase synthesis of 1-19 -adrenocorticotropic hormone, Alanyl- 1-19 -adrenocorticotropic hormone and Prolyl- 1-19 -adrenocorticotropic hormone and their adrenocorticotropic activity. Biochemistry 1972; 11:438-442.
59. Li CH, Hemmasi B. Adrenocorticotropin. 40. The Synthesis of a protected nonapeptide and of a biologically active nonadecapeptide related to adrenocorticotropic hormone. (5-glutamine) adrenocorticotropin-(1-19). J Med Chem 1972; 15:217-219.
60. Ramachandran J, Chung D, Li CH. Adrenocorticotropins. Xxxiv. Aspects of structure-activity relationships of the ACTH molecule. Synthesis of a heptadecapeptide amide, an octadecapeptide amide and a nonadecapeptide amide possessing high biological activities. J Am Chem Soc 1965; 87:2696-2708.
61. Haskell-Luevano C, Todorovic A, Gridley K et al. The melanocortin pathway: Effects of voluntary exercise on melanocortin-4 receptor knockout mice and ACTH(1-24) ligand structure activity relationships at the melanocortin-2 receptor. Endocrine Res 2004; 30:591-597. (Pubitemid 40070136)
62. Seelig S, Sayers G, Schwyzer R et al. Isolated adrenal cells: ACTH(11-24), a competitive antagonist of ACTH(1-39) and ACTH(1-10). FEBS Lett 1971; 19(3):232-234.
63. Engel MH, Sawyer TK, Hadley ME et al. Quantitative determination of amino acid racemization in Heat-Alkali-Treated melanotropins: Implications for peptide hormone strucute-function studies. Anal Biochem 1981; 116:303-311. (Pubitemid 12221200)
64. Bednarek M, MacNeil T, Tang R et al. Analogs of a-melanocyte stimulating hormone with high agonist potency and selectivity at human melanocortin receptor 1b: The role of Trp9 in molecular recognition. Biopolymers 2007; 89:401-408.
65. Bednarek M, MacNeil T, Tang R et al. Potent and selective agonists of α-melanotropin (αMSH) action at human melanocortin receptor 5; linear analogs of α-melanotropin. Peptides 2007; 28:1020-1028. (Pubitemid 46654443)
66. Hruby VJ, Mosberg HI. Conformational and dynamic considerations in peptide structure-function studies. Peptides 1982; 3(3):329-336. (Pubitemid 12022678)
67. Hruby V. Designing peptide receptor agonists and antagonists. Nat Rev Drug Discov 2002; 1:847-858. (Pubitemid 37361580)
68. 10]-a-Melanocyte-stimulating hormone: A cyclic a-melanotropin exhibiting superagonist biological activity. Proc Natl Acad Sci USA 1982; 79:1751-1755. (Pubitemid 12088505)
69. 7] substituted MSH analogues for the melanocortin receptor subtypes. Peptides 1997; 18(7):1009-1013. (Pubitemid 27489377)
70. Schioth HB, Mutulis F, Muceniece R et al. Discovery of novel melanocortin4 receptor selective MSH analogues. Br J Pharmacol 1998; 124(1):75-82. (Pubitemid 28210046)
71. Skuladottir GV, Jonsson L, Skarphedinsson JO et al. Long term orexigenic effect of a novel melanocortin 4 receptor selective antagonist. Br J Pharmacol 1999; 126(1):27-34. (Pubitemid 29041740)
72. Al-Obeidi F, Hruby VJ, Castrucci AM et al. Design of potent linear a-Melanotropin 4-10 analogues modified in positions 5 and 10. J Med Chem 1989; 32(1):174-179. (Pubitemid 19025307)
73. Fan W, Boston BA, Kesterson RA et al. Role of melanocortinergic neurons in feeding and the agouti obesity syndrome. Nature 1997; 385:165-168. (Pubitemid 27034218)
74. Hess S, Linde Y, Ovadia O et al. Backbone cyclic peptidomimetic melanocortin-4 receptor agonist as a novel orally administrated drug lead for treating obesity. J Med Chem 2008; 51(4):1026-1034. (Pubitemid 351304710)
75. Linde Y, Ovadia O, Safrai E et al. Structure-activity relationship and metabolic stability studies of backbone cyclization and N-methylation of melanocortin peptides. Biopolymers 2008; 90:671-690.
76. 2 tetrapeptides with amide bond modifications. J Pept Res 2004; 63(3):270-278. (Pubitemid 38496679)
77. McNulty JC, Jackson PJ, Thompson DA et al. Structures of the agouti signaling protein. J Mol Biol 2005; 346(4):1059-1070. (Pubitemid 40215530)
78. Shutter JR, Graham M, Kinsey AC et al. Hypothalamic expression of ART, a novel gene related to agouti, is up-regulated in obese and diabetic mutant mice. Genes and Development 1997; 11(5):593-602. (Pubitemid 27133379)
79. Haskell-Luevano C, Monck EK. Agouti-related protein (AGRP) functions as an inverse agonist at a constitutively active brain melanocortin-4 receptor. Regulatory Peptides 2001; 99:1-7. (Pubitemid 32232121)
80. Nijenhuis WA, Oosterom J, Adan RA. AGRP(83-132) Acts as an inverse agonist on the human-melanocortin-4 receptor. Mol Endocrinol 2001; 15(1):164-171. (Pubitemid 32156049)
81. McNulty JC, Thompson DA, Bolin KA et al. High-resolution NMR structure of the chemically-synthesized melanocortin receptor binding domain AGRP(87-132) of the agouti-related protein. Biochemistry 2001; 40:15520-15527. (Pubitemid 34015179)
82. Tota MR, Smith TS, Mao C et al. Molecular interaction of agouti protein and agouti-related protein with human melanocortin receptors. Biochemistry 1999; 38(3):897-904.
83. Haskell-Luevano C, Monck EK, Wan YP et al. The agouti-related protein decapeptide (Yc[CRFFNAFC] Y) possesses agonist activity at the murine melanocortin-1 receptor. Peptides 2000; 21(5):683-689. (Pubitemid 30392398)
84. Thirumoorthy R, Holder JR, Bauzo RM et al. Novel agouti-related protein (AGRP) based melanocortin-1 receptor antagonist. J Med Chem 2001; 44:4114-4124. (Pubitemid 33095319)
85. Jarosinski MA, Dodson SW, Harding BJ et al. Design and synthesis of simplified AGRP(65-112) analogues: Protein-mimetics with affinity at the melanocortin receptors. 2nd International and 17th American Peptide Symposium. San Diego, CA; 2001:Poster #322.
86. Joseph CG, Bauzo RM, Xiang Z et al. Elongation studies of the human agouti-related protein (AGRP) core decapeptide (Yc[CRFFNAFC]Y) results in antagonism at the mouse melanocortin-3 receptor. Peptides 2003; 27:263-270. (Pubitemid 36369346)
87. Jackson PJ, McNulty JC, Yang YK et al. Design, pharmacology and NMR structure of a minimized cystine knot with agouti-related protein activity. Biochemistry 2002; 41(24):7565-7572. (Pubitemid 34627783)
88. Joseph CG, Wang XS, Scott JW et al. Stereochemical studies of the monocyclic agouti-related protein (103-122) Arg-Phe-Phe residues: Conversion of a melanocortin-4 receptor antagonist into an agonist and results in the discovery of a potent and selective melanocortin-1 agonist. J Med Chem 2004; 47(27):6702-6710. (Pubitemid 40053759)
89. Wilczynski A, Wang XS, Joseph CG et al. Identification of putative agouti-related protein(87-132)-Melanocortin-4 receptor interactions by homology molecular modeling and validation using chimeric peptide ligands. J Med Chem 2004; 47(9):2194-2207. (Pubitemid 38478843)
90. 101-Cys119, Cys110-Cys117) bicyclic agouti-related protein (AGRP) melanocortin receptor antagonist. J Med Chem 2004; 47:5662-5673. (Pubitemid 39447263)
91. Han G, Quillan J, Carlson K et al. Design of novel vhimeric melanotropin-deltorphin analogues. Discovery of the first potent human melanocortin 1 receptor antagonist. J Med Chem 2003; 46:810-819. (Pubitemid 36258871)
92. Joseph CG, Wilczynski AM, Holder JR et al. Chimeric NDP-MSH and MTII melanocortin peptides with agouti-related protein (AGRP) Arg-Phe-Phe amino acids possess agonist melanocortin receptor activity. Peptides 2003; 24:1899-1908. (Pubitemid 38177625)
93. 2 peptide template. J Med Chem 2005; 48(8):3060-3075. (Pubitemid 40548118)
94. Jackson PJ, Yu B, Hunrichs B et al. Chimeras of the agouti-related protein: Insights into agonist and antagonist selectivity of melanocortin receptors. Peptides 2005; 26(10):1978-1987. (Pubitemid 41354557)
95. Bures, EJ, Hui, JO; Young, Y et al. Determination of disulfide structure in agouti-related protein (AGRP) by stepwise reduction and alkylation. Biochemistry 1998; 37:12172-12177. (Pubitemid 28411302)