Identification of a stable chemerin analog with potent activity toward ChemR23

Peptides

Volumn 30, Issue 8, 2009, Pages 1529-1538

  Shimamura, Ken ^a   Matsuda, Masao ^a   Miyamoto, Yasuhisa ^a   Yoshimoto, Ryo ^a   Seo, Toru ^a   Tokita, Shigeru ^a  

^a BANYU PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Adipokine; Chemerin; Peptide tool

Indexed keywords

ADIPOCYTOKINE; CHEMERIN DERIVATIVE; CHEMOKINE LIKE RECEPTOR 1; FATTY ACID; G PROTEIN COUPLED RECEPTOR; UNCLASSIFIED DRUG;

ADIPOCYTE; ADIPOGENESIS; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; ASTHMA; CONTROLLED STUDY; DIABETES MELLITUS; DIET RESTRICTION; DRUG HALF LIFE; DRUG METABOLISM; DRUG POTENCY; DRUG STABILITY; DRUG SYNTHESIS; FEMALE; IMMUNOREGULATION; LIPOLYSIS; MALE; METABOLIC DISORDER; MOUSE; NONHUMAN; NUCLEOTIDE SEQUENCE; OBESITY; PRIORITY JOURNAL;

3T3 CELLS; ADIPOCYTES; AMINO ACID SEQUENCE; ANIMALS; CHEMOTACTIC FACTORS; CHO CELLS; CRICETINAE; CRICETULUS; INTERCELLULAR SIGNALING PEPTIDES AND PROTEINS; MASS SPECTROMETRY; MICE; MOLECULAR SEQUENCE DATA; PEPTIDES; RECEPTORS, CHEMOKINE;

MUS;

EID: 67650484719     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.peptides.2009.05.030     Document Type: Article

References (37)

1. Arita M., Bianchini F., Aliberti J., Sher A., Chiang N., Hong S., Yang R., Petasis N.A., and Serhan C.N. Stereochemical assignment, anti-inflammatory properties, and receptor for the omega-3 lipid mediator resolvin E1. J Med Chem 201 (2005) 713-722
2. Aubry A., Ghermani N., and Marraud M. Backbone side chain interactions in peptides. I. Crystal structures of model dipeptides with the Pro-Ser sequence. Int J Pept Protein Res 23 (1984) 113-122
3. Barnea G., Strapps W., Herrada G., Bergman Y., Ong J., Kloss B., et al. The genetic design of signaling cascade to record receptor activation. Proc Natl Acad Sci USA 105 (2008) 64-69
4. Bozaoglu K., Bolton K., McMillan J., Zimmet P., Jowett J., Collier G., et al. Chemerin is a novel adipokine associated with obesity and metabolic syndrome. Endocrinology 148 (2007) 4687-4694
5. Budesinsky M., Sebestik J., Bednarova L., Baumruk V., Safarik M., and Bour P. Conformational properties of the Pro-Gly motif in the d-Ala-l-Pro-Gly-d-Ala model peptide explored by a statistical analysis of the NMR, Raman, and Raman optical activity spectra. J Org Chem 73 (2008) 1481-1489
6. Cash J.L., Hart R., Russ A., Dixon J.P.C., Colledge W.H., Doran J., et al. Synthetic chemerin-derived peptides suppress inflammation through ChemR23. J Exp Med 205 (2008) 767-775
7. Deacon C.F., Knudsen L.B., Madsen K., Wiberg F.C., Jacobsen O., and Holst J.J. Dipeptidyl peptidase IV resistant analogues of glucagon-like peptide-1 which have extended metabolic stability and improved biological activity. Diabetologia 41 (1998) 271-278
8. Falcomer C.M., Meinwald Y.C., Choudhary I., Talluri S., Milburn P.J., Clardy J., et al. Chain reversals in model peptides: studies of cystine-containing cyclic peptides. 3. Conformational free energies of cyclization of tetrapeptides of sequence Ac-Cys-Pro-X-Cys-NHMe. J Am Chem Soc 114 (1992) 4036-4042
9. Gonzalez-Periz A., Horrillo R., Ferre N., Gronert K., Dong B., Moran-Salvador E., et al. Obesity-induced insulin resistance and hepatic steatosis are alleviated by w-3 fatty acids: a role for resolvins and protectins. FASEB J (2009) 10.1096/fj.08-125674
10. Goralski K.B., McCarthy T.C., Hanniman E.A., Zabel B.A., Butcher E.C., Parlee S.D., et al. Chemerin, a novel adipokine that regulates adipogenesis and adipocyte metabolism. J Biol Chem 282 (2007) 28175-28188
11. Green B.D., Gault V.A., O'harte F.P., and Flatt P.R. Structurally modified analogues of glucagon-like peptide-1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP) as future antidiabetic agents. Curr Pharm Des 10 (2004) 3651-3662
12. Guillabert A., Wittamer V., Bondue B., Godot V., Imbault V., Parmentier M., et al. Role of neutrophil proteinase 3 and mast cell chymase in chemerin proteolytic regulation. J Leukoc Biol 84 (2008) 1530-1538
13. Haworth O., Cernadas M., Yang R., Serhan N.C., and Levy B.D. Resolvin E1 regulates interleukin 23, interferon-g and lipoxin A4 to promote the resolution of allergic airway inflammation. Nat Immunol 9 (2008) 873-879
14. Heveker N., Montes M., Germeroth L., Amara A., Trautmann A., Alizon M., et al. Dissociation of the signalling and antiviral properties of SDF-1-derived small peptides. Curr Biol 8 (1998) 369-376
15. John H., Hierer J., Haas O., and Forssmann W.G. Quantification of angiotensin-converting-enzyme-mediated degradation of human chemerin 145-154 in plasma by matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry. Anal Biochem 362 (2007) 117-125
16. Libert F., Parmentier M., Lefort A., Dinsart C., Van Sande J., Maenhaut C., et al. Selective amplification and cloning of four new members of the G protein-coupled receptor family. Science 244 (1989) 569-572
17. Loetscher P., Gong J.H., Dewald B., Baggiolini M., and Clark-Lewis I. N-terminal peptides of stromal cell-derived factor-1 with CXC chemokine receptor 4 agonist and antagonist activities. J Biol Chem 273 (1998) 22279-22283
18. Marks N., Stern F., and Benuck M. Correlation between biological potency and biodegradation of a somatostatin analogue. Nature 261 (1976) 511-512
19. Marraud M., and Aubry A. Backbone side chain interactions in peptides. II. Solution study of serine-containing model dipeptides. Int J Pept Protein Res 23 (1984) 123-133
20. Meder W., Wendland M., Busmann A., Kutzleb C., Spodsberg N., John H., et al. Characterization of human circulating TIG2 as a ligand for the orphan receptor ChemR23. FEBS Lett 555 (2003) 495-499
21. Methner A., Hermey G., Schinke B., and Hermans-Borgmeyer I. A novel G protein-coupled receptor with homology to neuropeptide and chemoattractant receptors expressed during bone development. Biochem Biophys Res Commun 233 (1997) 336-342
22. Mussig K., Saiger H., Machicao F., Thamer C., Machann J., Schick F., et al. RARRES2, encoding the novel adipokines chemerin, is a genetic determinant of disproportional regional body fat distribution: a comparative magnetic resonance imaging study. Metabol Clin Exp 58 (2009) 519-524
23. Nagpal S., Patel S., Jacobe H., DiSepio D., Ghosn C., Malhotra M., et al. Tazarotene-induced gene 2 (TIG2), a novel retinoid-responsive gene in skin. J Invest Dermatol 109 (1997) 91-95
24. Nock B.A., Nikolopoulou A., Reubi J.C., Maes V., Conrath P., Tourwe D., et al. Toward stable N4-modified neurotensins for NTS1-receptor-targeted tumor imaging with 99mTc. J Med Chem 49 (2006) 4767-4776
25. Parolini S., Santoro A., Marcenaro E., Luini W., Massardi L., Facchetti F., et al. The role of chemerin in the colocalization of NK and dendritic cell subsets into inflamed tissues. Blood 109 (2007) 3625-3632
26. Roh S.G., Song S.H., Choi K.C., Katoh K., Wittamer V., Parmentier M., et al. Chemerin-a new adipokine that modulates adipogenesis via its own receptor. Biochem Biophys Res Commun 362 (2007) 1013-1018
27. Samson M., Edinger A.L., Stordeur P., Rucker J., Verhasselt V., Sharron M., et al. ChemR23, a putative chemoattractant receptor, is expressed in monocyte-derived dendritic cells and macrophages and is a coreceptor for SIV and some primary HIV-1 strains. Eur J Immunol 28 (1998) 1689-1700
28. Schiller P.W., Weltrowska G., Nguyen T.M., Wilkes B.C., Chung N.N., and Lemieux C. TIPP[psi]: a highly potent and stable pseudopeptide delta opioid receptor antagonist with extraordinary delta selectivity. J Med Chem 36 (1993) 3182-3187
29. Takahashi M., Takahashi Y., Takahashi K., Zolotaryov F.N., Hong K.S., Kitazawa R., et al. Chemerin enhances insulin signaling and potentiates insulin-stimulated glucose uptake in 3T3-L1 adipocytes. FEBS Lett 582 (2008) 573-578
30. Wittamer V., Bondue B., Guillabert A., Vassart G., Parmentier M., and Communi D. Neutrophil-mediated maturation of chemerin: a link between innate and adaptive immunity. J Immunol 175 (2005) 487-493
31. Wittamer V., Franssen J.D., Vulcano M., Mirjolet J.F., Le Poul E., Migeotte I., et al. Specific recruitment of antigen-presenting cells by chemerin, a novel processed ligand from human inflammatory fluids. J Exp Med 198 (2003) 977-985
32. Wittamer V., Gregoire F., Robberecht P., Vassart G., Communi D., and Parmentier M. The C-terminal nonapeptide of mature chemerin activates the chemerin receptor with low nanomolar potency. J Biol Chem 279 (2004) 9956-9962
33. Zabel B.A., Allen S.J., Kulig P., Allen J.A., Cichy J., Handel T.M., et al. Chemerin activation by serine proteases of the coagulation, fibrinolytic, and inflammatory cascades. J Biol Chem 280 (2005) 34661-34666
34. Zabel B.A., Nakae S., Zuniga L., Kim J.-Y., Ohyama T., Alt C., et al. Mast cell-expressed orphan receptor CCRL2 binds chemerin and is required for optimal induction of IgE-mediated passive cutaneous anaphylaxis. J Exp Med 205 (2008) 2207-2220
35. Zabel B.A., Ohyama T., Zuniga L., Kim J.Y., Johnston B., Allen S.J., et al. Chemokine-like receptor 1 expression by macrophages in vivo: regulation by TGF-beta and TLR ligands. Exp Hematol 34 (2006) 1106-1114
36. Zabel B.A., Silverio A.M., and Butcher E.C. Chemokine-like receptor 1 expression and chemerin-directed chemotaxis distinguish plasmacytoid from myeloid dendritic cells in human blood. J Immunol 174 (2005) 244-251
37. Zabel B.A., Zuniga L., Ohyama T., Allen S.J., Cichy J., Handel T.M., et al. Chemoattractants, extracellular proteases, and the integrated host defense response. Exp Hematol 34 (2006) 1021-1032