lyngbya toxins

Summary

Summary: Toxins isolated from any species of the seaweed Lyngbya or similar chemicals from other sources, including mollusks and micro-organisms. These have been found to be potent tumor promoters. They are biosynthesized from TRYPTOPHAN; VALINE; and METHIONINE nonribosomally (PEPTIDE BIOSYNTHESIS, NUCLEIC ACID-INDEPENDENT).

Top Publications

  1. Williams P, Luesch H, Yoshida W, Moore R, Paul V. Continuing studies on the cyanobacterium Lyngbya sp.: isolation and structure determination of 15-norlyngbyapeptin A and lyngbyabellin D. J Nat Prod. 2003;66:595-8 pubmed
    ..Lyngbyabellin D (3) displayed an IC(50) value of 0.1 microM against the KB cell line. ..
  2. Kaneko Y, Tsukamoto A, Kurokawa K. Involvement of down-regulation-resistant protein kinase C in teleocidin inhibition of cell proliferation and calcium mobilization induced by epidermal growth factor and vasopressin in human hepatoma cells. Cancer Lett. 1993;71:103-8 pubmed
    ..This down-regulation-resistant PKC is suggested to be responsible for the inhibitory effect of teleocidin on cell proliferation and calcium mobilization induced by epidermal growth factor and vasopressin. ..
  3. Williams P, Yoshida W, Quon M, Moore R, Paul V. The structure of Palau'amide, a potent cytotoxin from a species of the marine cyanobacterium Lyngbya. J Nat Prod. 2003;66:1545-9 pubmed
    ..The assignment of S rather than R stereochemistry at C-37 is discussed in detail. ..
  4. Edwards D, Gerwick W. Lyngbyatoxin biosynthesis: sequence of biosynthetic gene cluster and identification of a novel aromatic prenyltransferase. J Am Chem Soc. 2004;126:11432-3 pubmed
    ..LtxC was heterologously produced and purified from E. coli and shown to catalyze the transfer of a geranyl group to (-)-indolactam V as the final step in the biosynthesis of lyngbyatoxin A. ..
  5. An T, Kumar T, Wang M, Liu L, Lay J, Liyanage R, et al. Structures of pahayokolides A and B, cyclic peptides from a Lyngbya sp. J Nat Prod. 2007;70:730-5 pubmed
    ..These peptides were purified from a new species of cyanobacteria of the genus Lyngbya, which was isolated from a periphyton mat from the Florida Everglades. ..
  6. Matthew S, Schupp P, Luesch H. Apratoxin E, a cytotoxic peptolide from a guamanian collection of the marine cyanobacterium Lyngbya bouillonii. J Nat Prod. 2008;71:1113-6 pubmed publisher
    ..The 5- to 15-fold reduced activity compared with apratoxin A (2) is attributed to the dehydration in the long-chain polyketide unit, which could affect the conformation of the molecule. ..
  7. Han B, Gross H, Goeger D, Mooberry S, Gerwick W. Aurilides B and C, cancer cell toxins from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula. J Nat Prod. 2006;69:572-5 pubmed
  8. Osborne N, Shaw G, Webb P. Health effects of recreational exposure to Moreton Bay, Australia waters during a Lyngbya majuscula bloom. Environ Int. 2007;33:309-14 pubmed
    ..In conclusion, high numbers of participants reported symptoms after exposure to waters subject to L. majuscula blooms but only a small number appeared to be serious in nature suggesting limited exposure to toxins. ..
  9. Osborne N, Webb P, Shaw G. The toxins of Lyngbya majuscula and their human and ecological health effects. Environ Int. 2001;27:381-92 pubmed
    ..The potential exists for toxins from Lyngbya majuscula affecting ecological health and in particular marine reptiles. ..

More Information

Publications91

  1. Gutierrez M, Suyama T, Engene N, Wingerd J, Matainaho T, Gerwick W. Apratoxin D, a potent cytotoxic cyclodepsipeptide from papua new guinea collections of the marine cyanobacteria Lyngbya majuscula and Lyngbya sordida. J Nat Prod. 2008;71:1099-103 pubmed publisher
    ..Apratoxin D (1) showed potent in vitro cytotoxicity against H-460 human lung cancer cells with an IC 50 value of 2.6 nM. ..
  2. Teruya T, Sasaki H, Fukazawa H, Suenaga K. Bisebromoamide, a potent cytotoxic peptide from the marine cyanobacterium Lyngbya sp.: isolation, stereostructure, and biological activity. Org Lett. 2009;11:5062-5 pubmed publisher
    ..Bisebromoamide (1) exhibited potent protein kinase inhibition: the phosphorylation of ERK in NRK cells by PDGF-stimulation was selectively inhibited by treatment with 10-0.1 microM of 1. ..
  3. Balunas M, Linington R, Tidgewell K, Fenner A, Ureña L, Togna G, et al. Dragonamide E, a modified linear lipopeptide from Lyngbya majuscula with antileishmanial activity. J Nat Prod. 2010;73:60-6 pubmed publisher
    ..Biosynthetic differences among marine compounds with a terminal free amide are also discussed. ..
  4. Onodera H, Satake M, Oshima Y, Yasumoto T, Carmichael W. New saxitoxin analogues from the freshwater filamentous cyanobacterium Lyngbya wollei. Nat Toxins. 1997;5:146-51 pubmed
    ..The presence of acetate in the side chain resulted in a sevenfold to 17-fold times decrease in mouse toxicity compared to their carbamoyl counterparts, while the reduction at C-12 resulted in a complete loss of mouse toxicity. ..
  5. Carmichael W, Evans W, Yin Q, Bell P, Moczydlowski E. Evidence for paralytic shellfish poisons in the freshwater cyanobacterium Lyngbya wollei (Farlow ex Gomont) comb. nov. Appl Environ Microbiol. 1997;63:3104-10 pubmed
    ..Fifty field samples were placed in unialgal culture and grown under defined culture conditions. Toxicity and signs of poisoning for these laboratory-grown strains of L. wollei were similar to those of the field collection samples. ..
  6. Isakov N, Gopas J, Priel E, Segal S, Altman A. Effect of protein kinase C activating tumor promoters on metastases formation by fibrosarcoma cells. Invasion Metastasis. 1991;11:14-24 pubmed
  7. Yamamoto S, Gotoh H, Aizu E, Sasakawa N, Hiai H, Kato R. Differential effects of diacylglycerols and 12-O-tetradecanoylphorbol-13-acetate on protein phosphorylation and cell proliferation of tumor promoter-dependent leukemia cell line A65T. Carcinogenesis. 1988;9:1857-62 pubmed
  8. Vital P, Tanner D. Efficient and highly enantioselective formation of the all-carbon quaternary stereocentre of lyngbyatoxin A. Org Biomol Chem. 2006;4:4292-8 pubmed
  9. Nishio K, Sugimoto Y, Nakagawa K, Niimi S, Fujiwara Y, Bungo M, et al. Cross-resistance to tumour promoters in human cancer cell lines resistant to adriamycin or cisplatin. Br J Cancer. 1990;62:415-9 pubmed
    ..These results suggest the presence of another common mechanism for resistance to ADM and CDDP as well as to TPA- or non-TPA-type tumour promoters. ..
  10. Irie K, Okuno S, Koshimizu K, Tokuda H, Nishino H, Iwashima A. Biological activities and cellular uptake studies of fluorescent derivatives of indole alkaloid tumor promoter teleocidin. Int J Cancer. 1989;43:513-9 pubmed
    ..This suggested that hydrophobicity rather than biological activity determines the cellular uptake of these fluorescent probes. ..
  11. Kong F, Kishi Y, Perez Sala D, Rando R. The pharmacophore of debromoaplysiatoxin responsible for protein kinase C activation. Proc Natl Acad Sci U S A. 1991;88:1973-6 pubmed
    ..These findings provide strong experimental support for our structural model of protein kinase C activation. ..
  12. Milligan K, Marquez B, Williamson R, Gerwick W. Lyngbyabellin B, a toxic and antifungal secondary metabolite from the marine cyanobacterium Lyngbya majuscula. J Nat Prod. 2000;63:1440-3 pubmed
    ..The planar structure was deduced using 1D and 2D NMR spectroscopic methods, and the stereochemistry is proposed through a combination of NMR and chiral GC/MS analysis. ..
  13. Uhl J, Newton R, Gross J, Rommi W, Mochan E. Modulation of synovial fibroblast plasminogen activator and plasminogen activator inhibitor production by protein kinase C. Biochim Biophys Acta. 1991;1097:283-8 pubmed
    ..These results suggest that activation of PKC may play an important role in regulating increased PA production associated with joint destruction in rheumatoid arthritis (RA). ..
  14. Pereira A, McCue C, Gerwick W. Cyanolide A, a glycosidic macrolide with potent Molluscicidal activity from the Papua New Guinea cyanobacterium Lyngbya bouillonii. J Nat Prod. 2010;73:217-20 pubmed publisher
    ..2 microM). The structure of cyanolide A (2) was elucidated through extensive NMR spectroscopic analyses, yielding a symmetrical dimer that represents the newest addition to the family of glycosidic macrolides from cyanobacteria. ..
  15. Meickle T, Matthew S, Ross C, Luesch H, Paul V. Bioassay-guided isolation and identification of desacetylmicrocolin B from Lyngbya cf. polychroa. Planta Med. 2009;75:1427-30 pubmed publisher
    ..Compounds 1, 2, and 3 were obtained by reverse-phase chromatography and their structures were determined by NMR and MS. In this paper we report the isolation, identification, and biological activity of 1. ..
  16. van Apeldoorn M, van Egmond H, Speijers G, Bakker G. Toxins of cyanobacteria. Mol Nutr Food Res. 2007;51:7-60 pubmed
    ..Official regulations for other cyanotoxins have not been established, although some (provisional) guideline values have been derived for microcystins in drinking water by WHO and several countries. ..
  17. Dangel B, Godula K, Youn S, Sezen B, Sames D. C-C bond formation via C-H bond activation: synthesis of the core of teleocidin B4. J Am Chem Soc. 2002;124:11856-7 pubmed
    ..Noteworthy is the fact that steps 1 and 3 critically depended on the directing role of the aniline nitrogen (directed C-H bond functionalization). ..
  18. Budunova I, Mittelman L, Belitsky G. Identification of tumor promoters by their inhibitory effect on intercellular transfer of lucifer yellow. Cell Biol Toxicol. 1989;5:77-89 pubmed
    ..All the promoters investigated had a reversible effect on the dye transfer. The value of the dye transfer method for promoter screening is discussed. ..
  19. Capper A, Tibbetts I, O Neil J, Shaw G. The fate of Lyngbya majuscula toxins in three potential consumers. J Chem Ecol. 2005;31:1595-606 pubmed
    ..The high levels of secondary metabolites observed in both the anaspidean and the cephalapsidean species suggest that these toxins may bioaccumulate through marine food chains. ..
  20. Kinoshita T, Takahashi I, Kobayashi E, Tamaoki T, Irie K, Koshimizu K, et al. Suppression by protein kinase C inhibitors of tumor promoter enhancement of Epstein-Barr virus-induced growth transformation. Anticancer Res. 1990;10:1051-4 pubmed
    ..All these events were suppressed by exposure to 10-100 nM UCN-01 or to calphostin C. Our findings suggest that the tumor promoter enhancement of EBV growth transformation is probably mediated by PKC. ..
  21. Teshima S, Shimosato Y, Kodama T, Koide T, Suganuma M, Fujiki H. Resistance of human bronchial epithelial cells to teleocidin in a two-stage carcinogenesis experiment. Acta Pathol Jpn. 1987;37:1859-65 pubmed
    ..Thus, teleocidin had an effect on mouse tissues, but seemed to have no effect on human bronchial cells, although it is uncertain whether the grafted human bronchi were initiated by DMBA. ..
  22. Fukasawa H, Yamaguchi M, Hashimoto Y, Endo Y, Shudo K. Enhancing effect of tumor promoters, phorbol esters and teleocidins on nuclear receptor-mediated transcription. Biol Pharm Bull. 2000;23:1414-7 pubmed
    ..These results suggest this reporter system is useful for the evaluation of effects on the gene expression of various tumor promoters, including non-TPA type. ..
  23. Graf K, Tabor M, Brown M, Paige M. Synthesis of (S)-jamaicamide C carboxylic acid. Org Lett. 2009;11:5382-5 pubmed publisher
    ..The methyl stereocenter was installed using Evans' oxazolidinone methodology, and the trisubstituted chloroolefin was set by silylstannylation of a triple bond. ..
  24. Liu L, Bearden D, Rein K. Biosynthetic origin of the 3-amino-2,5,7,8-tetrahydroxy-10-methylundecanoic acid moiety and absolute configuration of pahayokolides A and B. J Nat Prod. 2011;74:1535-8 pubmed publisher
    ..Incorporation of labeled leucine and acetate precursors into the pahayokolides has established that Athmu is derived from a leucine or ?-keto isocaproic acid starter unit, which is further extended with three acetate units. ..
  25. Kikumori M, Yanagita R, Tokuda H, Suenaga K, Nagai H, Irie K. Structural optimization of 10-methyl-aplog-1, a simplified analog of debromoaplysiatoxin, as an anticancer lead. Biosci Biotechnol Biochem. 2016;80:221-31 pubmed publisher
    ..Compound 2 would be the optimized seed for anticancer drugs among the simplified analogs of DAT. ..
  26. Willey J, Moser C, Harris C. Effects of aplysiatoxin and debromoaplysiatoxin on growth and differentiation of normal human bronchial epithelial cells. Cell Biol Toxicol. 1984;1:145-54 pubmed
  27. Fujiki H, Suganuma M, Suguri H, Takagi K, Yoshizawa S, Ootsuyama A, et al. New antitumor promoters: (-)-epigallocatechin gallate and sarcophytols A and B. Basic Life Sci. 1990;52:205-12 pubmed
    ..EGCG and sarcophytols showed inhibition of tumor development by chemical carcinogenesis. A possibility of developing these compounds as cancer chemopreventives for human beings is discussed. ..
  28. Apte R, Keisari Y. Differential stimulation of mononuclear phagocyte IL 1 production and oxidative burst by tumor-promoting and non-tumor-promoting agents. Immunobiology. 1987;175:470-81 pubmed
    ..The afore-described findings lend support to the idea that chronic inflammatory phagocytes might play a role in the tumor promoting process by furnishing both carcinogenic and growth factors at the site of tumor origin. ..
  29. Imamoto A, Wang X, Fujiki H, Walker S, Beltrán L, DiGiovanni J. Comparison of 12-O-tetradecanoylphorbol-13-acetate and teleocidin for induction of epidermal hyperplasia, activation of epidermal PKC isozymes and skin tumor promotion in SENCAR and C57BL/6 mice. Carcinogenesis. 1993;14:719-24 pubmed
    ..Taken together, the current data suggest that factors in addition to the induction of sustained epidermal hyperplasia, control responsiveness of C57BL/6 mice to skin tumor promotion by diverse promoting stimuli. ..
  30. Rando R, Kishi Y. Structural basis of protein kinase C activation by diacylglycerols and tumor promoters. Biochemistry. 1992;31:2211-8 pubmed
    ..The overall model presented is consistent with published structure-activity studies on the tumor promoters and makes testable predictions that have proven to be correct thus far. ..
  31. Takagi K, Suganuma M, Kagechika H, Shudo K, Ninomiya M, Muto Y, et al. Inhibition of ornithine decarboxylase induction by retinobenzoic acids in relation to their binding affinities to cellular retinoid-binding proteins. J Cancer Res Clin Oncol. 1988;114:221-4 pubmed
    ..These results suggest that the inhibition of ODC induction can be mediated by pathways that do not involve CRABP or the cellular retinol-binding protein. ..
  32. Thomson C, Wilkie J. The conformations and electrostatic potential maps of phorbol esters, teleocidins and ingenols. Carcinogenesis. 1989;10:531-40 pubmed
    ..Electrostatic potentials were calculated and displayed using an in-house program 3D2, while superpositions of molecules were carried out using CHEM-X. ..
  33. Endo Y, Ohno M, Hirano M, Fujiwara T, Sato A, Hinuma Y, et al. Teleocidins and benzolactams inhibit cell killing by human immunodeficiency virus type 1 (HIV-1). Biol Pharm Bull. 1994;17:1147-9 pubmed
    ..Teleocidin B-4 and structurally related synthetic benzolactams were found to be potent inhibitors of cell killing by HIV-1. One of the benzolactams, (-)-BL-V8-310, showed a high selectivity index. ..
  34. Watanabe M, Kawase Y, Tanabe J, Min K, Mue S, Ohuchi K. Suppression of interleukin-1 alpha production by protein kinase C activators in human vascular endothelial cells. J Pharmacol Exp Ther. 1995;272:808-14 pubmed
    ..The present work indicates that the production of cell-associated IL-1 alpha stimulated by TNF-alpha, IL-1 beta or lipopolysaccharide is inhibited by treatment with TPA, aplysiatoxin or teleocidin.(ABSTRACT TRUNCATED AT 250 WORDS) ..
  35. Itai A, Kato Y, Tomioka N, Iitaka Y, Endo Y, Hasegawa M, et al. A receptor model for tumor promoters: rational superposition of teleocidins and phorbol esters. Proc Natl Acad Sci U S A. 1988;85:3688-92 pubmed
    ..Their mutual spatial arrangements are most important for biological activity. ..
  36. Ma D, Zhang T, Wang G, Kozikowski A, Lewin N, Blumberg P. Synthesis of 7,8-disubstituted benzolactam-V8 and its binding to protein kinase C. Bioorg Med Chem Lett. 2001;11:99-101 pubmed
    ..6, 91.1, and 121.3 nM to PKCalpha, delta, and epsilon, respectively), indicating that introduction of a suitable substituent at the 7-position of 8-decynyl-benzolactam-V8 only slightly reduces the PKC binding affinity. ..
  37. Bjare U, Lundblad G, Ivhed I, Nilsson K. Patterns of glycosidases in the histiocytic cell line U-937. Effects of agents inducing cell differentiation. Int J Biochem. 1988;20:1291-8 pubmed
    ..5. Alterations have been monitored as relative effects upon the absolute glycosidase activities and as effects upon selected ratios of different glycosidases. 6. The separate inducing agents show distinct enzyme patterns. ..
  38. Clark B, Engene N, Teasdale M, Rowley D, Matainaho T, Valeriote F, et al. Natural products chemistry and taxonomy of the marine cyanobacterium Blennothrix cantharidosmum. J Nat Prod. 2008;71:1530-7 pubmed publisher
    ..Nevertheless, these are the first natural products to be reported from this genus, and this inspired a detailed morphologic and 16S rDNA-based phylogenetic analysis of the producing organism. ..
  39. Shudo K. [From cancer prevention to cancer treatment]. Yakugaku Zasshi. 2000;120:987-95 pubmed
    ..Further retinoid research yielded retinoids antagonists, and then RXR(retinoic acid-X-receptor)-agonists and RXR-antagonists. These ligands have a big potential in the therapy of diabetes and obesity. ..
  40. Ito E, Nagai H. Bleeding from the small intestine caused by aplysiatoxin, the causative agent of the red alga Gracilaria coronopifolia poisoning. Toxicon. 2000;38:123-32 pubmed
    ..Then, in the small intestine, similar changes appeared to have occurred, and bleeding was induced in two characteristic ways, one through deposition of fibrin in the lumen and the other via distension of the capillary wall. ..
  41. Mihali T, Carmichael W, Neilan B. A putative gene cluster from a Lyngbya wollei bloom that encodes paralytic shellfish toxin biosynthesis. PLoS ONE. 2011;6:e14657 pubmed publisher
  42. Thornburg C, Cowley E, Sikorska J, Shaala L, Ishmael J, Youssef D, et al. Apratoxin H and apratoxin A sulfoxide from the Red Sea cyanobacterium Moorea producens. J Nat Prod. 2013;76:1781-8 pubmed publisher
  43. Grove D, Mastro A. Differential activation and inhibition of lymphocyte proliferation by phorbol esters, mezerein, teleocidin, and okadaic acid. Cancer Res. 1991;51:82-8 pubmed
    ..In no case was the modulation of protein kinase C separated from the effects on IL-2 production and proliferation. ..
  44. Komori A, Yatsunami J, Okabe S, Abe S, Hara K, Suganuma M, et al. Anticarcinogenic activity of green tea polyphenols. Jpn J Clin Oncol. 1993;23:186-90 pubmed
    ..The sealing effect would account for reversible growth arrest, and may be induced by various kinds of compound. ..
  45. Tsukamoto A, Kaneko Y, Kurokawa K. Novobiocin modulates cytokeratin assembly and differentiation of human hepatoma cells induced by butyrate and teleocidin. Cancer Lett. 1991;60:51-7 pubmed
    ..These results suggest that butyrate and teleocidin induce cell differentiation via distinct signaling pathway and that novobiocin and butyrate can be used as subsidiary drugs in preventing the growth of hepatoma. ..
  46. Liu L, Rein K. New peptides isolated from Lyngbya species: a review. Mar Drugs. 2010;8:1817-37 pubmed publisher
    ..This review covers peptides and hybrid polyketide-non-ribosomal peptides isolated from Lyngbya species. The structures and bioactivities of 50 Lyngbya peptides which were reported since 2007 are presented. ..
  47. Yoshizawa S, Fujiki H, Suguri H, Suganuma M, Nakayasu M, Matsushima R, et al. Tumor-promoting activity of staurosporine, a protein kinase inhibitor on mouse skin. Cancer Res. 1990;50:4974-8 pubmed
    ..These results demonstrated that staurosporine is a weak tumor promoter of mouse skin compared with teleocidin, but staurosporine has some potency to inhibit tumor promotion by teleocidin. ..
  48. Kikumori M, Yanagita R, Tokuda H, Suzuki N, Nagai H, Suenaga K, et al. Structure-activity studies on the spiroketal moiety of a simplified analogue of debromoaplysiatoxin with antiproliferative activity. J Med Chem. 2012;55:5614-26 pubmed publisher
    ..These results suggest that 5 is a potent PKC ligand without tumor-promoting activity and could be a therapeutic lead for the treatment of cancer, like bryostatins. ..
  49. Benjamin D, Hooker S, Miller J. Differential effects of teleocidin on TNF alpha receptor regulation in human B cell lines: relationship to coexpression of IL-2 and IL-1 receptors and to lymphokine secretion. Cell Immunol. 1990;125:480-97 pubmed
  50. Huynh M, Elston M, Hernandez N, Ball D, Kajiyama S, Irie K, et al. Enzymatic production of (-)-indolactam V by LtxB, a cytochrome P450 monooxygenase. J Nat Prod. 2010;73:71-4 pubmed publisher
    ..The relaxed substrate specificity of LtxB, along with the relaxed specificity of the prenyltransferase, LtxC, allowed for the enzymatic production of a series of (-)-indolactam V and lyngbyatoxin analogues. ..
  51. Mullin J, McGinn M, Snock K, Imaizumi S. The effects of teleocidin and aplysiatoxin tumor promoters on epithelial tight junctions and transepithelial permeability: comparison to phorbol esters. Carcinogenesis. 1990;11:377-85 pubmed
    ..These four tumor promoters, TPA, PDBU, teleocidin and aplysiatoxin, are all known protein kinase C activators, and support the case for protein-kinase-C-mediated control of tight junctional permeability. ..
  52. Levine L, Fujiki H, Sakai S, Gjika H, Van Vunakis H. A radioimmunoassay for the teleocidins using 26 (2'-aminoethylthio)-tetrahydroteleocidin A-2 as hapten. Carcinogenesis. 1988;9:1629-33 pubmed
    ..3 pmol) greater than (-)-indolactam-V (3.7 nmol) greater than teleocidin B-4 (13 nmol). Maitotoxin, aplysiatoxin, palytoxin, mezerein, okadaic acid and 12-O-tetradecanoylphorbol-13-acetate did not inhibit at the levels tested. ..
  53. Yadav J, Rajendar G, Rao R, Pabbaraja S. Total synthesis of nhatrangin A. J Org Chem. 2013;78:8524-30 pubmed publisher
    ..Synthesis of nhatrangin A was accomplished by coupling of dihydroxy acid 12 with ?-hydroxyallyl ester (obtained from 11) under Yamaguchi reaction conditions followed by a one-pot deprotection of all protecting groups. ..
  54. Marquez B, Watts K, Yokochi A, Roberts M, Verdier Pinard P, Jimenez J, et al. Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly. J Nat Prod. 2002;65:866-71 pubmed
    ..Structurally, hectochlorin resembles dolabellin and the recently reported lyngbyabellin class of compounds. ..
  55. Issinger O, Martin T, Richter W, Olson M, Fujiki H. Hyperphosphorylation of N-60, a protein structurally and immunologically related to nucleolin after tumour-promoter treatment. EMBO J. 1988;7:1621-6 pubmed
    ..Hyperphosphorylation of the nucleolin fragment (N-60) was suppressed by anti-tumour promoter retinoic acid. ..
  56. Levine L. Amplification of arachidonic acid metabolism in rat liver cells (the C-9 cell-line) by tosyl-L-phenylalanine chloromethyl ketone and phenylmethyl-sulfonyl fluoride. Prostaglandins. 1995;50:89-101 pubmed
    ..While phenylmethyl-sulfonyl fluoride's amplification of PGI2 production by cells treated with TPA was blocked by prior incubation with TPA for 20 h, a similar block of amplification in EGF-treated cells was not observed. ..
  57. Barak D, Shibata M, Rein R. Structural investigation of protein kinase C inhibitors. J Mol Struct. 1991;230:419-29 pubmed
    ..The model shows two sites of hydrophobic interaction and enables the inhibitory activity of gossypol to be accounted for. ..
  58. Meseguer B, Alonso Díaz D, Griebenow N, Herget T, Waldmann H. Solid-phase synthesis and biological evaluation of a teleocidin library--discovery of a selective PKCdelta down regulator. Chemistry. 2000;6:3943-57 pubmed
  59. Ito E, Nagai H. Morphological observations of diarrhea in mice caused by aplysiatoxin, the causative agent of the red alga Gracilaria coronopifolia poisoning in Hawaii. Toxicon. 1998;36:1913-20 pubmed
    ..The cecum was the main target of the diarrhea. After the diarrhea ended, the number of goblet cells was increased remarkably and many fine cracks were left on the surface of the epithelium. ..
  60. Sueoka N, Sueoka E, Okabe S, Fujiki H. Anti-cancer effects of morphine through inhibition of tumour necrosis factor-alpha release and mRNA expression. Carcinogenesis. 1996;17:2337-41 pubmed
    ..The high dosage of morphine required to induce anticarcinogenic effects is also discussed. ..
  61. Hewitt S, Duffy P, Orton T, Garner R. Effect of tumour promoters and non-genotoxic carcinogens on terminal differentiation and proliferation in mouse teratoma XB2 cells cultured in low calcium medium. Carcinogenesis. 1990;11:371-5 pubmed
    ..We suggest that this culture system may provide a useful model for studies of the mechanism of promotion and non-genotoxic carcinogenesis in epithelial tissues. ..
  62. Sims J, Brock J, Fujioka R, Killion L, Nakagawa L, Greco S. Vibrio in stinging seaweed: potential infection. Hawaii Med J. 1993;52:274-5 pubmed
    ..Lymphadenopathy, pustular folliculitus, and local infections have been reported in some persons. ..
  63. Suganuma M, Yatsunami J, Yoshizawa S, Okabe S, Fujiki H. Absence of synergistic effects on tumor promotion in CD-1 mouse skin by simultaneous applications of two different types of tumor promoters, okadaic acid and teleocidin. Cancer Res. 1993;53:1012-6 pubmed
    ..The effect of cotreatment of okadaic acid and teleocidin is discussed at the molecular level. ..
  64. Tsukamoto A, Kaneko Y, Kurokawa K. Thapsigargin, an inhibitor of endoplasmic reticulum Ca(2+)-ATPase, enhances c-fos expression but antagonizes vacuole formation of human hepatoma cells induced by teleocidin. Biochim Biophys Acta. 1993;1177:31-6 pubmed
    ..From these results it was speculated that the Ca2+ leak from the endoplasmic reticulum rather than the elevation of cytosolic Ca2+ appeared to be responsible for the specific inhibition of vacuole formation by thapsigargin. ..
  65. Suzuki K, Mizuno R, Suenaga K, Teruya T, Tanaka N, Kosaka T, et al. Bisebromoamide, an extract from Lyngbya species, induces apoptosis through ERK and mTOR inhibitions in renal cancer cells. Cancer Med. 2013;2:32-9 pubmed publisher
    ..Similar effects were demonstrated for phosphorylation of mTOR and p70 S6. Bisebromoamide is a promising potential agent against RCC due to its ability to inhibit both the Raf/MEK/ERK and PI3K/Akt/mTOR pathways. ..
  66. Nagai H, Yasumoto T, Hokama Y. Aplysiatoxin and debromoaplysiatoxin as the causative agents of a red alga Gracilaria coronopifolia poisoning in Hawaii. Toxicon. 1996;34:753-61 pubmed
    ..Furthermore, we observed blue-green algal parasitism on the surface of the toxic G. coronopifolia. Therefore, epiphytic organisms such as blue-green algae might be the true origin of the toxins in G. coronopifolia. ..
  67. Kikuchi H, Ohtsuki T, Koyano T, Kowithayakorn T, Sakai T, Ishibashi M. Activity of mangosteen xanthones and teleocidin a-2 in death receptor expression enhancement and tumor necrosis factor related apoptosis-inducing ligand assays. J Nat Prod. 2010;73:452-5 pubmed publisher
    ..Thus, the present results suggested that 5 has the ability to overcome TRAIL resistance via the up-regulation of DR5 and may be an effective sensitizer of TRAIL-resistant cells. ..
  68. Carter L, Blakeslee J. The effects of tumor promoters on HTLV-1 expression in a low-virus producer and a non-virus producer cell line. Cancer Lett. 1988;39:329-38 pubmed
    ..Chemicals did not induce HTLV-I antigen expression in the C63/CI(II-2) cell line. No enhancement of reverse transcriptase activity or alteration of proviral organization was observed after chemical treatment of MT-1 cells. ..
  69. Nam K, Kimura S, Fujiki H, Imanishi Y. Effects of phorbol ester and teleocidin on Ca2+-induced fusion of liposomes. Biochem Biophys Res Commun. 1989;165:1256-61 pubmed
    ..Thus, Ca2+-induced fusion of PS vesicles was shown to be sensitive to defects of the membrane surface, but insensitive to defects of the hydrophobic core of the lipid membrane. ..
  70. Gaveriaux C, Fehr T, Montecino Rodriguez E, Sanglier J, Loor F. Protein kinase C activators of the teleocidin family decrease the IgE-binding capacity of rat basophilic leukemia cells. Int Arch Allergy Appl Immunol. 1988;86:465-71 pubmed
    ..It is suggested that the down-regulation of IgE receptor expression by these tumor promoters is mediated through protein kinase C activation and phosphorylation of the Fc epsilon R. ..
  71. Knust H, Hoffmann R. A case study in conformation design: learning by doing. Chem Rec. 2002;2:405-18 pubmed
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