Internalization of CCR4 and inhibition of chemotaxis by K777, a potent and selective CCR4 antagonist

Pharmacology

Volumn 91, Issue 5-6, 2013, Pages 305-313

  Sato, Takashi ^a,b   Iwase, Miho ^a   Miyama, Motoki ^a   Komai, Masato ^a   Ohshima, Etsuo ^a   Asai, Akira ^b   Yano, Hiroshi ^a   Miki, Ichiro ^a  

^a KYOWA HAKKO KOGYO CO LTD   (Japan)

^b UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

Anti asthmatic drugs; Chemotaxis; Receptor antagonists

Indexed keywords

CALCIUM ION; CHEMOKINE RECEPTOR ANTAGONIST; CHEMOKINE RECEPTOR CCR4; CHEMOKINE RECEPTOR CXCR4; CHEMOTAXIS INHIBITOR; K 777; THYMUS AND ACTIVATION REGULATED CHEMOKINE; UNCLASSIFIED DRUG; CCL1 CHEMOKINE; [1 [1 [4 (2,4 DIFLUOROBENZYLAMINO) 5 (2,4 DIFLUOROPHENYL)PYRIMIDIN 2 YL]PIPERIDIN 4 YL] 1 METHYLPIPERIDIN 1 IUM IODIDE];

ARTICLE; BINDING ASSAY; CALCIUM MOBILIZATION; CELL CULTURE; CELL SURFACE; CHEMOTAXIS; CONCENTRATION RESPONSE; DRUG BINDING SITE; DRUG STRUCTURE; FLOW CYTOMETRY; HUMAN; HUMAN CELL; IC 50; INTERNALIZATION; PRIORITY JOURNAL; SCATCHARD PLOT; ANTIGEN BINDING; CALCIUM MOBILIZATION ASSAY; CHEMOTAXIS ASSAY; CONFOCAL MICROSCOPY; CONTROLLED STUDY; DRUG SELECTIVITY; IC50; IMMUNOFLUORESCENCE;

EID: 84878693497     PISSN: 00317012     EISSN: 14230313     Source Type: Journal    
DOI: 10.1159/000350390     Document Type: Article

References (42)

1. Insel PA, Snead A, Murray F, Zhang L, Yokouchi H, Katakia T, et al: GPCR expression in tissues and cells: Are the optimal receptors being used as drug targets? Br J Pharmacol 2012; 165: 1613-1616.
2. Feldman RD, Gros R: New insights into the regulation of cAMP synthesis beyond GPCR/G protein activation: Implications in cardiovascular regulation. Life Sci 2007; 81: 267-271.
3. Tyndall JD, Sandilya R: GPCR agonists and antagonists in the clinic. Med Chem 2005; 1: 405-421.
4. Swinney DC: Biochemical mechanisms of drug action: What does it take for success? Nat Rev Drug Discov 2004; 3: 801-808.
5. Gether U: Uncovering molecular mechanisms involved in activation of G protein-coupled receptors. Endocr Rev 2000; 21: 90-113.
6. Wyllie DJA, Chen PE: Taking the time to study competitive antagonism. Br J Pharmacol 2007; 150: 541-551.
7. Knoflach F, Mutel V, Jolidon S, Kew JN, Malherbe P, Vieira E, et al: Positive allosteric modulators of metabotropic glutamate 1 receptor: Characterization, mechanism of action, and binding site. Proc Natl Acad Sci USA 2001; 98: 13402-13407.
8. May LT, Avlani VA, Sexton PM, Christopoulos A: Allosteric modulation of G proteincoupled receptors. Curr Pharm Des 2004; 10: 2003-2013.
9. Luster AD: Chemokines - chemotactic cytokines that mediate inflammation. N Engl J Med 1998; 338: 436-445.
10. Kaplan A: Chemokines, chemokine receptors and allergy. Int Arch Allergy Immunol 2001; 124: 423-431.
11. Lichtman AH, Abbas AK: T-cell subsets: Recruiting the right kind of help. Curr Biol 1997; 7:R242-R244.
12. Crump MP, Gong JH, Loetscher P, Rajarathnam K, Amara A, Arenzana-Seisdedos F, et al: Solution structure and basis for functional activity of stromal cell-derived factor-1; dissociation of CXCR4 activation from binding and inhibition of HIV-1. EMBO J 1997; 16: 6996-7007.
13. Loetscher P, Gong JH, Dewald B, Baggiolini M, Clark-Lewis I: N-terminal peptides of stromal cell-derived factor-1 with CXC chemokine receptor 4 agonist and antagonist activities. J Biol Chem 1998; 273: 22279-22283.
14. Asojo OA, Boulègue C, Hoover DM, Lu W, Lubkowskia J: Structures of thymus and activation-regulated chemokine (TARC). Acta Crystallogr D Biol Crystallogr 2003; 59: 1165-1173.
15. Clark-Lewis I, Kim K, Rajarathnam K, Gong JH, Dewald B, Moser B, et al: Structure-activity relationship of chemokines. J Leukoc Biol 1995; 57: 703-711.
16. Imai T, Baba M, Nishimura M, Kakizaki M, Takagi S, Yoshie O: The T cell-directed CC chemokine TARC is a highly specific biological ligand for CC chemokine receptor 4. J Biol Chem 1997; 272: 15036-15042.
17. Imai T, Chantry D, Raport CJ, Wood CL, Nishimura M, Godiska R, et al: Macrophagederived chemokine is a functional ligand for the CC chemokine receptor 4. J Biol Chem 1998; 273: 1764-1768.
18. Imai T, Nagira M, Takagi S, Kakizaki M, Nishimura M, Wang J, et al: Selective recruitment of CCR4-bearing Th2 cells toward antigen-presenting cells by the CC chemokines thymus and activation-regulated chemokine and macrophage-derived chemokine. Int Immunol 1999; 11: 81-88.
19. Iellema A, Mariania M, Langa R, Recaldeb H, Panina-Bordignona P, Sinigagliaa F, et al: Unique chemotactic response profile and specific expression of chemokine receptors CCR4 and CCR8 by CD4+CD25+ regulatory T cells. J Exp Med 2001; 194: 847-854.
20. Faustino L, Mucida D, Keller AC, Demengeot J, Bortoluci K, Sardinha LR, et al: Regulatory T cells accumulate in the lung allergic inflammation and efficiently suppress T-cell proliferation but not Th2 cytokine production. Clin Dev Immunol 2012;2012:721817.
21. Saito K, Torii M, Ma N, Tsuchiya T, Wang L, Hori T, et al: Differential regulatory function of resting and preactivated allergen-specific CD4+CD25+ regulatory T cells in Th2-type airway inflammation. J Immunol 2008; 181: 6889-6897.
22. Sekiya T, Miyamasu M, Imanishi M, Yamada H, Nakajima T, Yamaguchi M, et al: Inducible expression of a Th2-type CC chemokine thymus-and activation-regulated chemokine by human bronchial epithelial cells. J Immunol 2000; 165: 2205-2213.
23. Panina-Cordignon P, Papi A, Mariani M, Lucia PD, Casoni G, Bellettato C, et al: The C-C chemokine receptors CCR4 and CCR8 identify airway T cells of allergen-challenged atopic asthmatics. J Clin Invest 2001; 107: 1357-1364.
24. Terada N, Nomura T, Kim WJ, Otsuka Y, Takahashi R, Kishi H, et al: Expression of C-C chemokine TARC in human nasal mucosa and its regulation by cytokines. Clin Exp Allergy 2001; 31: 1923-1931.
25. Zheng X, Nakamura K, Furukawa H, Nishibu A, Takahashi M, Tojo M, et al: Demonstration of TARC and CCR4 mRNA expression and distribution using in situ RT-PCR in the regional skin of atopic dermatitis. J Dermatol 2003; 30: 26-32.
26. Nouri-Aria KT, Wilson D, Francis JN, Jopling LA, Jacobson MR, Hodge MR, et al: CCR4 in human allergen-induced late responses in the skin and lung. Eur J Immunol 2002; 32: 1933-1938.
27. Pease JE, Horuk R: Chemokine receptor antagonists: Part 1. Expert Opin Ther Pat 2009; 19: 39-58.
28. Wang X, Xu F, Xu Q, Mahmud H, Houze J, Zhu L, et al: Optimization of 2-aminothiazole derivatives as CCR4 antagonists. Bioorg Med Chem Lett 2006; 16: 2800-2803.
29. Allen S, Newhouse B, Anderson AS, Fauber B, Allen A, Chantry D, et al: Discovery and SAR of trisubstituted thiazolidinones as CCR4 antagonists. Bioorg Med Chem Lett 2004; 14: 1619-1624.
30. Kuhn CF, Bazin M, Philippe L, Zhang J, Tylaska L, Miret J, Bauer PH: Bipiperidinyl carboxylic acid amides as potent, selective, and functionally active CCR4 antagonists. Chem Biol Drug Des 2007; 70: 268-272.
31. Yokoyama K, Ishikawa N, Igarashi S, Kawano N, Hattori K, Miyazaki T, et al: Discovery of potent CCR4 antagonists: Synthesis and structure-activity relationship study of 2,4-diaminoquinazolines. Bioorg Med Chem Lett 2008; 16: 7021-7032.
32. Purandare AV, Gao A, Wan H, Somerville J, Burke C, Seachord C, et al: Identification of chemokine receptor CCR4 antagonist. Bioorg Med Chem Lett 2005; 15: 2669-2672.
33. Purandare AV, Wan H, Gao A, Somerville J, Burke C, Vaccaro W, et al: Optimization of CCR4 antagonists: Side-chain exploration. Bioorg Med Chem Lett 2006; 16: 204-207.
34. Purandare AV, Wana H, Somervillea JE, Burkea C, Vaccaroa W, Yanga X, et al: Core exploration in optimization of chemokine receptor CCR4 antagonists. Bioorg Med Chem 2007; 17: 679-682.
35. Sato T, Komai M, Iwase M, Kobayashi K, Tahara H, Ohshima E, et al: Inhibitory effect of the new orally active CCR4 antagonist K327 on CCR4+CD4+ T cell migration into the lung of mice with ovalbumin-induced lung allergic inflammation. Pharmacology 2009; 84: 171-182.
36. Gootenberg JE, Ruscetti FW, Mier JW, Gazdar A, Gallo RC: Human cutaneous T cell lymphoma and leukemia cell lines produce and respond to T cell growth factor. J Exp Med 1981; 154: 1403-1418.
37. Ravid Z, Goldblum N, Zaizov R, Schlesinger M, Kertes T, Minowada J, et al: Establishment and characterization of a new leukemic T-cell line (PEER) with an unusual phenotype. Int J Cancer 1980; 25: 705-710.
38. Matsumoto Y, Funahashi J, Mori K, Hayashi K, Yano H: The noncompetitive antagonism of histamine H1 receptor expressed in Chinese hamster ovary cells by olopatadine hydrochloride: Its potency and molecular mechanism. Pharmacology 2007; 81: 266-274.
39. Mariani M, Lang R, Binda E, Panina-Bordignon P, D'Ambrosio D: Dominance of CCL22 over CCL17 in induction of chemokine receptor CCR4 desensitization and internalization on human Th2 cells. Eur J Immunol 2004; 34: 231-240.
40. Urban JD, Clarke WP, von Zastrow M, Nichols DE, Kobilka B, Weinstein, H, et al: Functional selectivity and classical concepts of quantitative pharmacology. J Pharmacol Exp Ther 2007; 320: 1-13.
41. Howard OMZ, Korte T, Tarasova NI, Grimm M, Turpin JA, Rice WG, et al: Small molecule inhibitor of HIV-1 cell fusion blocks chemokine receptor-mediated function. J Leukoc Biol 1998; 64: 6-13.
42. Robinson CR: Reduce, reuse, and recycle. Nat Biotechnol 2002; 20: 879-880.