Isolation and structures of novel fungal metabolites as chemokine receptor (CCR2) antagonists

Journal of Antibiotics

Volumn 58, Issue 11, 2005, Pages 686-694

  Herath, Kithsiri B ^a   Jayasuriya, Hiranthi ^a   Ondeyka, John G ^a   Polishook, Jon D ^a   Bills, Gerald F ^b   Dombrowski, Anne W ^a   Cabello, Angeles ^b   Vicario, Pasquale P ^a   Zweerink, Hans ^a   Guan, Ziqiang ^a   Singh, Sheo B ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b Medical affairs Merck sharp and Dohme ltd   (Spain)

Author keywords

bis thioketopiperazines; CCR2 antagonists; Microbial products; Natural products

Indexed keywords

BIS THIODIKETOPIPERAZINE DERIVATIVE; CHAETOMIN; CHEMOKINE RECEPTOR CCR2; CHEMOKINE RECEPTOR CCR2 ANTAGONIST; CYTOCHALASIN A; CYTOCHALASIN B; CYTOCHALASIN DERIVATIVE; EMESTRIN; EMESTRIN DERIVATIVE; MONOCYTE CHEMOTACTIC PROTEIN 1; NATURAL PRODUCT; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; ATHEROSCLEROSIS; BIOASSAY; CITHAREXYLUM MACREDENIUM; CONTROLLED STUDY; CYTOKINE PRODUCTION; DRUG ISOLATION; DRUG STRUCTURE; FUNGAL METABOLISM; IC 50; INFLAMMATION; MACROPHAGE; MEMORY T LYMPHOCYTE; MONOCYTE; MULTIPLE SCLEROSIS; MYCELIUM; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN EXPRESSION; RHEUMATOID ARTHRITIS;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CELL MEMBRANE; CELLS, CULTURED; CHEMOKINE CCL2; CYTOCHALASINS; DISULFIDES; FUNGI; HUMANS; INDOLE ALKALOIDS; MOLECULAR STRUCTURE; MONOCYTES; PEPTIDE FRAGMENTS; PIPERAZINES; RECEPTORS, CHEMOKINE;

ANIMALIA; CITHAREXYLUM; RODENTIA;

EID: 29344467621     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2005.94     Document Type: Article

References (22)

1. Ley K. Arrest, migration, survival, and proliferation of leukocytes and vascular cells: The many faces of chemokine biology. Microcirculation 10: 245-246 (2003)
2. Daly C, Rollins BJ. Monocyte chemoattractant protein-1 (CCL2) in inflammatory disease and adaptive immunity: Therapeutic opportunities and controversies. Micro-circulation 10: 247-257 (2003)
3. Charo IF, Peters W. Chemokine receptor 2 (CCR2) in atherosclerosis, infectious diseases, and regulation of T-cell proliferation. Microcirculation 10: 259-264 (2003)
4. Rose CE, Jr, Sung SSJ, Fu SM. Significant involvement of CCL2 (MCP1) in inflammatory disorders of the lung. Microcirculation 10: 273-288 (2003)
5. Cascieri MA, Springer MS. The chemokine/chemokine-receptor family: Potential and progress for therapeutic intervention. Curr Opin Chem Biol 4: 420-427 (2000)
6. Gong JH, Ratkay LG, Waterfield JD, Clark-Lewis I. An antagonist of monocyte chemoattractant protein 1 (MCP-1) inhibits arthritis in the MRL-lpr mouse model. J Exp Med 186: 131-137 (1997)
7. Brodmerkel CM, Collins R, Hall L, Hertel D, Stewart R, Wang A, Xue CB, Diamond S, Friedman S, Vaddi K. In 68th Annual Meeting of American College of Rheumatology, San Antonio, Texas, 2004
8. Seya H, Nozawa K, Nakajima S, Kawai K, Udagawa S. Studies on fungal products. Part 8. Isolation of structure of emestrin, a novel antifungal macrocyclic epithiodioxopiperazine from Emericella striata. X-ray molecular structure of emestrin. J Chem Soc Perkin Trans 1 1986: 109-116 (1986)
9. Ooike M, Nozawa K, Kawai KI. An epitetrathiodioxopiperazine related to emestrin from Emericella foveolata. Phytochemistry 46: 123-126 (1997)
10. Nozawa K, Udagawa S, Nakajima S, Kawai K. Studies on fungal products. XIV Emestrin B, a new epithrithiodioxopiperazine, from Emericella striata. Chem Pharm Bull 35: 3460-3463 (1987)
11. Onodera H, Hasegawa A, Tsumagari N, Nakai R, Ogawa T, Kanda Y. MPC1001 and its analogues: New antitumor agents from fungus Cladorrhinum species. Org Lett 6: 4101-4104 (2004)
12. Cole RJ, Cox RH. Handbook of Toxic Fungal Metabolites. Academic Press, New York, 1981.
13. Ueno Y, Umemori K, Nimi E, Tanuma S, Nagata S, Sugamata M, Ihara T, Sekijima M, Kawai K, Ueno I. Induction of apoptosis by T-2 toxin and other natural toxins in HL-60 humna promyelotic leukemia cells. Nat Toxins 3: 129-137 (1995)
14. Terao K, Ito E, Kawai K, Nozawa K, Udagawa S. Experimental acute poisoning in mice induced by emestrin, a new mycotoxin isolated from Emericella species. Mycopathologia 112: 71-79 (1990)
15. Ishikawa J, Okano J, Ohki K, Amagai A, Maeda Y, Miyata H. Phagocytosis of Dictyostelium discoideum studied by the particle-tracking method. Exp Cell Res 288: 268-276 (2003)
16. von-Wolff M, Ursel S, Hahn U, Steldinger R, Strowitzki T. Glucose transporter protiens (GLUT) in human endometrium: Expression, regulation, and function throughout the menstrual cycle and in early pregnancy. J Clin Endocrinol Metabol 88: 3885-3892 (2003)
17. Wndhaber RAJ, Wilkins RJ, Meredith D. Functional characterization of glucose transport in bovine articular chondrocytes. Pflügers Archiv Eur J Physiol 446: 572-577 (2003)
18. Hagglund CL, Gottschalk I, Lundahl P. Cytochalasin B-binding and transport properties of the Glut1 human red cell glucose transporter. Recent Res Dev Bioenerget 1: 117-129 (2000)
19. Ondeyka J, Hensens OD, Zink D, Ball R, Lingham RB, Bills G, Dombrowski A, Goetz M. L-696,474, a novel cytochalasin as an inhibitor of HIV-1 protease II. Isolation and structure. J Antibiot 45: 679-685 (1992)
20. Mack M, Kleinschmidt A, Bruhl H, Klier C, Nelson PJ, Cihak J, Plachw J, Stangassinger M, Erfle V, Schlondorff D. Transfer of the chemokine receptor CCR5 between cells by membrane-derived microparticles: A mechanism for cellular human immunodeficiency virus 1 infection. Nat Med 6: 769-775 (2000)
21. Gribble AD, Forbes IT, Witherington J. Preparation of 3-subsituted indoles or fused pyrroles as antagonists of the chemokine MCP-1 (CCR2B) receptor. GlaxoSmithKline, 2002, WO 2002079151 A1.
22. Yang L, Butora G, Parsons WH. Preparation of N-cyclopentylpiperidines as modulators of chemokine receptor activity. Merck & Co., Inc., 2002, WO 2002013824 A1.