FR235222, a Fungal Metabolite, is a Novel Immunosuppressant that Inhibits Mammalian Histone Deacetylase (HDAC)

FR258900 is a novel glycogen synthesis activator produced by Fungus No. 138354. This compound was isolated from the culture broth by solvent extraction and reverse-phase column chromatography. FR258900 stimulated glycogen synthesis and glycogen synthase activity in primary rat hepatocytes. FR258900 exhibited a potent inhibitory effect on the activity of liver glycogen phosphorylase, suggesting that this compound may activate hepatic glycogen synthesis via glycogen phosphorylase inhibition. Thus, this glycogen phosphorylase inhibitor may be useful in the treatment of postprandial hyperglycemia in type 2 diabetes.

[1]  G. Suske,et al.  Transcription factor Sp3 is regulated by acetylation. , 2001, Nucleic acids research.

[2]  M. Gómez-Lechón,et al.  A microassay for measuring glycogen in 96-well-cultured cells. , 1996, Analytical biochemistry.

[3]  H. Gritsch,et al.  Renal transplantation at the University of Pittsburgh: the impact of FK506. , 1994, Clinical transplants.

[4]  D M Schmatz,et al.  Apicidin: a novel antiprotozoal agent that inhibits parasite histone deacetylase. , 1996, Proceedings of the National Academy of Sciences of the United States of America.

[5]  J. Kirby,et al.  TGF-beta expression in renal transplant biopsies: a comparative study between cyclosporin-A and tacrolimus. , 2000, Transplantation.

[6]  K. Harada,et al.  A Nonempirical Method Using LC/MS for Determination of the Absolute Configuration of Constituent Amino Acids in a Peptide: Combination of Marfey's Method with Mass Spectrometry and Its Practical Application , 1997 .

[7]  W. Wilson,et al.  Inhibitor of histone deacetylation, depsipeptide (FR901228), in the treatment of peripheral and cutaneous T-cell lymphoma: a case report. , 2001, Blood.

[8]  M. Mochizuki,et al.  Effects of a new immunosuppressive agent, FK506, on experimental autoimmune uveoretinitis in rats. , 1988, Investigative ophthalmology & visual science.

[9]  H. Hausen,et al.  Inhibitors of histone deacetylase arrest cell cycle and induce apoptosis in cervical carcinoma cells circumventing human papillomavirus oncogene expression , 2001, Oncogene.

[10]  R. Nussenblatt,et al.  TREATMENT OF INTRAOCULAR INFLAMMATORY DISEASE WITH CYCLOSPORIN A , 1983, The Lancet.

[11]  T. Tsuruo,et al.  A synthetic inhibitor of histone deacetylase, MS-27-275, with marked in vivo antitumor activity against human tumors. , 1999, Proceedings of the National Academy of Sciences of the United States of America.

[12]  T. Kusumi,et al.  High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids , 1991 .

[13]  G. Bishop,et al.  Vascular endothelial growth factor expression in human chronic renal allograft rejection. , 1999, Transplantation.

[14]  F. Sakai,et al.  FR235222, a fungal metabolite, is a novel immunosuppressant that inhibits mammalian histone deacetylase (HDAC) II. Biological activities in animal models. , 2003, The Journal of antibiotics.

[15]  C. Van Lint,et al.  The expression of a small fraction of cellular genes is changed in response to histone hyperacetylation. , 1996, Gene expression.

[16]  F. Capani,et al.  Predominant Role of Gluconeogenesis in Increased Hepatic Glucose Production in NIDDM , 1989, Diabetes.

[17]  B. Ryffel,et al.  Nephrotoxicity of cyclosporin A and FK506: inhibition of calcineurin phosphatase. , 1995, Renal physiology and biochemistry.

[18]  Michel Goedert,et al.  GSK3 inhibitors: development and therapeutic potential , 2004, Nature Reviews Drug Discovery.

[19]  J. Baldwin,et al.  Stereospecific Synthesis of Chlamydocin , 1993 .

[20]  M. Yoshida,et al.  Potent histone deacetylase inhibitors built from trichostatin A and cyclic tetrapeptide antibiotics including trapoxin. , 2001, Proceedings of the National Academy of Sciences of the United States of America.

[21]  D. Lavelle,et al.  Histone deacetylase inhibitors increase p21WAF1 and induce apoptosis of human myeloma cell lines independent of decreased IL‐6 receptor expression , 2001, American journal of hematology.

[22]  M. Yoshida,et al.  Trapoxin, an antitumor cyclic tetrapeptide, is an irreversible inhibitor of mammalian histone deacetylase. , 1993, The Journal of biological chemistry.

[23]  K. Walsh,et al.  Cyclosporine downregulates Fas ligand expression on vascular endothelial cells: implication for accelerated vasculopathy by immunosuppressive therapy. , 1999, Biochemical and biophysical research communications.

[24]  N. Rosen,et al.  The histone deacetylase inhibitor suberoylanilide hydroxamic acid induces differentiation of human breast cancer cells. , 2001, Cancer research.

[25]  D. Schuppan,et al.  A histone deacetylase inhibitor, trichostatin A, suppresses myofibroblastic differentiation of rat hepatic stellate cells in primary culture , 1999, Hepatology.

[26]  R. DeFronzo,et al.  Pathogenesis of NIDDM: A Balanced Overview , 1992, Diabetes Care.

[27]  G. Kammer,et al.  Trichostatin A reverses skewed expression of CD154, interleukin-10, and interferon-γ gene and protein expression in lupus T cells , 2001, Proceedings of the National Academy of Sciences of the United States of America.

[28]  S. Tannenbaum,et al.  Analysis of nitrate, nitrite, and [15N]nitrate in biological fluids. , 1982, Analytical biochemistry.

[29]  D. Rich,et al.  The structure and conformation of HC-toxin. , 1983, Biochemical and biophysical research communications.

[30]  L. Devy,et al.  Histone deacetylases inhibitors as anti-angiogenic agents altering vascular endothelial growth factor signaling , 2002, Oncogene.

[31]  T. Kinoshita,et al.  FR235222, a fungal metabolite, is a novel immunosuppressant that inhibits mammalian histone deacetylase III. Structure determination. , 2003, The Journal of antibiotics.

[32]  J. Till,et al.  Characterization of the factor in L‐cell conditioned medium capable of stimulating colony formation by mouse marrow cells in culture , 1971, Journal of cellular physiology.

[33]  R. Huguenin,et al.  Isolierung und Strukturaufklärung von Chlamydocin , 1974 .

[34]  P. Marks,et al.  Histone deacetylase inhibitors: inducers of differentiation or apoptosis of transformed cells. , 2000, Journal of the National Cancer Institute.

[35]  Tetsuo Yoshida,et al.  Selective inhibition of IL-2 gene expression by trichostatin A, a potent inhibitor of mammalian histone deacetylase. , 1996, The Journal of antibiotics.

[36]  M. Yoshida,et al.  Mechanism of cell cycle arrest caused by histone deacetylase inhibitors in human carcinoma cells. , 2000, The Journal of antibiotics.

[37]  D. Faller,et al.  Butyrate in the treatment of sickle cell disease and &bgr;-thalassemia , 1995, Current opinion in hematology.

[38]  K. Sakamoto,et al.  FR235222, a fungal metabolite, is a novel immunosuppressant that inhibits mammalian histone deacetylase (HDAC). I. Taxonomy, fermentation, isolation and biological activities. , 2003, The Journal of antibiotics.

[39]  E. Bradbury,et al.  Butyrate suppression of histone deacetylation leads to accumulation of multiacetylated forms of histones H3 and H4 and increased DNase I sensitivity of the associated DNA sequences. , 1978, Proceedings of the National Academy of Sciences of the United States of America.

[40]  R. Macdermott,et al.  Molecular Medicine © 1999 The Picower Institute Press Butyrate Switches the Pattern of Chemokine Secretion by Intestinal Epithelial Cells through , 2022 .

[41]  S. Schreiber,et al.  Depudecin induces morphological reversion of transformed fibroblasts via the inhibition of histone deacetylase. , 1998, Proceedings of the National Academy of Sciences of the United States of America.

[42]  P. Linsley,et al.  Long-term acceptance of skin and cardiac allografts after blocking CD40 and CD28 pathways , 1996, Nature.

[43]  T. Sakai,et al.  Histone deacetylase inhibitor activates the WAF1/Cip1 gene promoter through the Sp1 sites. , 1997, Biochemical and biophysical research communications.

[44]  K. Nakahara,et al.  Immunosuppressive effect of FK506 on collagen-induced arthritis in rats. , 1988, Clinical immunology and immunopathology.

[45]  H. W. Lee,et al.  Apicidin, a histone deacetylase inhibitor, inhibits proliferation of tumor cells via induction of p21WAF1/Cip1 and gelsolin. , 2000, Cancer research.

[46]  J W Yates,et al.  Selective small molecule inhibitors of glycogen synthase kinase-3 modulate glycogen metabolism and gene transcription. , 2000, Chemistry & biology.

[47]  H. Itazaki,et al.  Isolation and structural elucidation of new cyclotetrapeptides, trapoxins A and B, having detransformation activities as antitumor agents. , 1990, The Journal of antibiotics.

[48]  A. Laupacis,et al.  Effects of cyclosporine immunosuppression in insulin-dependent diabetes mellitus of recent onset. , 1984, Science.

[49]  D. Danley,et al.  Discovery of a human liver glycogen phosphorylase inhibitor that lowers blood glucose in vivo. , 1998, Proceedings of the National Academy of Sciences of the United States of America.

[50]  S. Tamura,et al.  Mass spectrometric determination of amino acid sequence in Cyl-2, a novel cyclotetrapeptide from Cylindrocladium scoparium. , 2005, Biomedical mass spectrometry.

[51]  M. Su,et al.  Induction of γ-Globin by Histone Deacetylase Inhibitors , 1997 .

[52]  M. Weinblatt,et al.  Cyclosporin A treatment of refractory rheumatoid arthritis. , 1987, Arthritis and rheumatism.

[53]  Yufang Shi,et al.  Fungal metabolite FR901228 inhibits c-Myc and Fas ligand expression , 1998, Oncogene.

[54]  R. Busuttil,et al.  A COMPARISON OF RENAL FUNCTION IN CYCLOSPORINE- AND FK‐506-TREATED PATIENTS AFTER PRIMARY ORTHOTOPIC LIVER TRANSPLANTATION , 1993, Transplantation.

[55]  W. Bechstein,et al.  Neurotoxicity of calcineurin inhibitors: impact and clinical management , 2000, Transplant international : official journal of the European Society for Organ Transplantation.

[56]  T. Strom,et al.  Blocking both signal 1 and signal 2 of T-cell activation prevents apoptosis of alloreactive T cells and induction of peripheral allograft tolerance , 1999, Nature Medicine.

[57]  V. Allfrey,et al.  Studies of acetylation and deacetylation in high mobility group proteins. Identification of the sites of acetylation in high mobility group proteins 14 and 17. , 1981, The Journal of biological chemistry.

[58]  Eun-Joung Moon,et al.  Histone deacetylases induce angiogenesis by negative regulation of tumor suppressor genes , 2001, Nature Medicine.

[59]  B. Kennedy,et al.  Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene. , 1999, Science.

[60]  T. Naoe,et al.  Apoptotic Cytotoxic Effects of a Histone Deacetylase Inhibitor, FK228, on Malignant Lymphoid Cells , 2000, Japanese journal of cancer research : Gann.

[61]  Ricky W. Johnstone,et al.  Histone-deacetylase inhibitors: novel drugs for the treatment of cancer , 2002, Nature Reviews Drug Discovery.

[62]  M. Bollen,et al.  Specific features of glycogen metabolism in the liver. , 1998, The Biochemical journal.

[63]  J. Katz,et al.  Inhibition of IL-8 gene expression in Caco-2 cells by compounds which induce histone hyperacetylation. , 1997, Cytokine.

[64]  K. Nakahara,et al.  Studies on WF-3161, a new antitumor antibiotic. , 1983, The Journal of antibiotics.

[65]  K. Gilbert,et al.  Induction of Anergy in Th1 Cells Associated with Increased Levels of Cyclin-Dependent Kinase Inhibitors p21Cip1 and p27Kip1 1 , 2001, The Journal of Immunology.

[66]  M. Woolfson,et al.  Direct‐space methods in phase extension and phase determination. I. Low‐density elimination , 1992 .

[67]  P. Seglen.  Preparation of isolated rat liver cells. , 1976, Methods in cell biology.

[68]  W. Zhang,et al.  Acetylation and modulation of erythroid Krüppel-like factor (EKLF) activity by interaction with histone acetyltransferases. , 1998, Proceedings of the National Academy of Sciences of the United States of America.

[69]  K. Fosgerau,et al.  Kinetic and functional characterization of 1,4-dideoxy-1, 4-imino-d-arabinitol: a potent inhibitor of glycogen phosphorylase with anti-hyperglyceamic effect in ob/ob mice. , 2000, Archives of biochemistry and biophysics.

[70]  Wei Gu,et al.  Activation of p53 Sequence-Specific DNA Binding by Acetylation of the p53 C-Terminal Domain , 1997, Cell.

[71]  R. Fletterick,et al.  An engineered liver glycogen phosphorylase with AMP allosteric activation. , 1991, The Journal of biological chemistry.

[72]  J. Radziuk,et al.  Hepatic glucose uptake, gluconeogenesis and the regulation of glycogen synthesis , 2001, Diabetes/metabolism research and reviews.