Ranopterins-amphibia skin pteridines displaying hematopoietic, immunomodulatory, and macrophageal proliferative biological activities

Pteridines

Volumn 10, Issue 4, 1999, Pages 178-189

  Zvetkova, Elissaveta ^a  

^a Institute of Experimental Morphology and Anthropology Bulgarian Academy of Sciences   (Bulgaria)

Author keywords

[No Author keywords available]

Indexed keywords

ISOXANTHOPTERIN; LEUKOPTERIN; NEOPTERIN; PIGMENT; PTERIDINE DERIVATIVE; PTERIN DERIVATIVE; RANOPTERIN; UNCLASSIFIED DRUG; XANTHOPTERIN;

AMPHIBIA; ARTICLE; AUTORADIOGRAPHY; CANCER CELL; CELL PROLIFERATION; CELL ULTRASTRUCTURE; CHROMATOPHORE; EXTRACTION; FLUORESCENCE; IMMUNOMODULATION; MACROPHAGE; PIGMENT CELL; PRIORITY JOURNAL; PURIFICATION; SKIN PIGMENTATION;

AMPHIBIA;

EID: 0033506304     PISSN: 09334807     EISSN: 21954720     Source Type: Journal    
DOI: 10.1515/pteridines.1999.10.4.178     Document Type: Article

References (99)

1. Hopkins F. G. Note on a yellow pigment in butterflies. Nature 1889; 40: 335.
2. Purrmann R. Konstitution und Synthese des sogenannten Anhydroleukopterins. Justus Liebigs Ann Chem 1941; 548: 284-292.
3. Rembold H., Buschmann L. Struktur und Synthese des Neopterins. Chem Ber 1963; 96: 1406-1410.
4. Rembold H., Buschmann L. Untersuchungen über die Pteridine der Bienenpuppe (Apis mellifica). Justus Liebigs Ann Chem 1963; 662: 72-82.
5. Blakley R. L. Natural occurrence of pterins and folate derivatives. In: The Biochemistry of Folic Acid and Related Pteridines (Pfleiderer W, Taylor E. C., eds.), North-Holland Publications, Amsterdam, 1969, pp 8-57.
6. Forrest H., Van Baalen C. Microbiology of unconjugated pteridines. Annu Rev Microbiol 1970; 24: 91-108.
7. Ziegler I., Harmsen R. The biology of pteridines in insects. Adv Insect Physiol 1969; 6: 139-62.
8. Hadjioloff A. I. Phenomenes de fluorescence determines par la lumiere de Wood au niveau de la peau de la grenouille. Bull Histol Appl 1929; 6: 37-47.
9. Hadjioloff A. I. Les chromatophores bleus dans la peau de la grenouille. Compt Rend Soc Biol, Paris, 1929; 100: 669-673.
10. Hadjioloff A. I. A propos des phenomenes de fluorescence determines par la lumiere de Wood au niveau des organes de l'homme et des animaux, a l'etal frais, apres autolyse et putrefication et apres calcination. Compt Rend Soc Biol, Paris, 1929; 102: 779.
11. Hadjioloff A. I. La methode luminoscopique dans la biologie et la medecine. (Conference tenue a Warsovie, le 27 avril, 1937). Folia morphologica (Warszawa) 1937; 7: 192-208.
12. Hadjioloff A. I., Krestev T. Phenomeries de fluorescence determines par la lumiere de Wood au niveau de la peau des poissons. Bull Histol appl 1932; 12: 153-158.
13. Hüttel R., Sprengling G. Über Ichthyopterin, einen blaufluoreszirenden Stoff aus Fischhaut. Annalen der Chemie 1943; 554: 69-82.
14. Hama, T. Substances fluorescentes de type pterinique dans la peau ou les yeux de la grenouille (Rana nigromaculata) et leurs transformations photochimiques. Experimentia 1953; 9: 299-300.
15. Günder, J. Über den papierchromatographischen und fluorestenzmikroskopischen Nachweis von Pterin und Riboflavin bei Amphibien und Reptilien. Naturwissenschaften 1953; 40: 20-21.
16. Günder, J. Nachweis und Lokalisation von Pterin und Riboflavin in der Haut von Amphibien und Reptilien. Z Vergl Physiol 1954; 36: 78-114.
17. Goto, T. Isolation and characterization of some fluorescent substances in the skin of the frog, Rana nigromaculata. Dobutsugaku Sassahi 1959; 68: 286-280.
18. Goto, T Über einen blaufluoreszierenden Stoff "Buffochrom", seine Isolierung aus der Haut einer Krote Bufo vulgaris und sein Verhalten in den Entwicklungestadien. Japanese J Zool 1963; 14: 83-90.
19. Goto, T. Fluoreszierender Stoff aus Bufo vulgaris: Konstitutionsaulklärung des Pteridins "Buffochrom". Japanese J Zool 1963; 14: 91-95.
20. Hadjioloff A. I., S. Atzev:Sur la luminescence propre des cellules et des tissus chez les vertebres inferieurs en rapport avec les pterines. C R Assoc Anat 1955; 42: 639-652
21. Atsev, S., A. I. Hadjioloff. On the biological action of pterins from the skin of Rana ridibunda. Bull Inst Morphol 1968;13:89-99.
22. Hadjioloff A. I, E. Zvetkova. Contribution a la fluorescence propre de la peau des amphibiens (Bombina variegata et Rana esculenta). Bull Assoc Anat Paris, 1970; 148: 384-387.
23. Hadjioloff A. I., E. Zvetkova. Layers with proper fluorescence in the derma of Amphibia.-Compt Rend Acad Bulg Sci 1978; 3: 481-484.
24. Hadjioloff A. I., E. Zvetkova. Intravital fluorochromation of proper fluorescentdermal layers in Amphibia by alisarine red and tetracycline. Compt Rend Acad Bulg Sci 1978; 31:603-606.
25. Hadjioloff A. I., E. Zvetkova. On the histochemistry of the proper fluorescent structures in the derma of Amphibia. Compt Rend Acad Bulg Sci 1978; 31: 759-762.
26. Hadjioloff A. I., Shivatcheva T. M., Veltcheva M. S., Dikov A. L. On the biological action of ranopterines. Compt Rend Acad Bulg Sci 1981; 34: 229-232.
27. Hadjiolov, A.I., E. Zvetkova. Fluorescent Properties of Cell and in Vertebrates and Humans. Publ House Bulg Acad Set Sofia, 1989, pp.1-195.
28. Bagnara, J. T. Chromatotropic hormone, pteridines and amphibian pigmentation. Gen Comp Endocrinol 1961; 1: 124-133.
29. Bagnara, J. T. Cytology and cytophysiology of non-melanophore pigment cells. Int Rev Cytol 1966; 20: 173-205.
30. Hama T., M. Obika. On the nature of some fluorescent substances of pterin type in the adult skin of toad, Bufo vulgaris formosus. Experientia 1958; 14: 182-184.
31. Hama, T., M. Obika. Histological distribution of pterins in the skin of bullfrog. Anat Res 1959; 134: 25-36.
32. Hama, T. The relation between the chromatophores and pterin compounds. Ann N Y Acad Sci 1963; 100: 977-982.
33. Obika, M. Association of pteridines with amphibian larval pigmentation and their biosynthesis in developing chromatophores. Develop Biol 1963; 6: 99-112.
34. Obika, M., J. T. Bagnara. Pteridines as pigments in amphibia. Science 1964; 143: 485-495.
35. Obika, M. Morphology and biochemistry of pterinosomes in lower vertebrates. In: Chemistry and biology of pteridines. (ed. W Pfleiderer). International Academic Printing Co, Tokyo, 1970, 413-423.
36. Bagnara, J. T, M. Obica. Comparative aspects of inegumental pteridine distribution among amphibians. Comp Biochem Physiol 1965; 15: 33-49.
37. Matsumoto, J. Studies on fine structure and cytochemical properties of erythrophores in Xiphophorus helleri, with special reference to their pigment granules. J Cell Biol 1965; 27: 493-504.
38. Matsumoto, J. Role of pteridines in the pigmentation of chromatophores in cypridin fish. Japan J Zool 1965; 14: 45.
39. Matsumoto, J., M. Obika. Morphological and biochemical characterization of goldfish erythrophores and their pterinosomes. J Cell Biol 1968; 39: 233-250.
40. Hadjioloff A. I., A. Manina, E. Zvetkova, A. Boyadjieva-Michailova, Z. Barbolova. Ultrastructural investigations on the dermal chromatophores in Amphibia. Compt Rend Acad Bulg Sci 1977; 30: 1507-1510.
41. Bagnara, J. T. Pigment cells. In: Biology of the Integument. 2. Vertebrates Bereiter-Hahn H., A.G. Matoltsy, S. Richards, Eds.) 1986, Springer-Verlag, Heidelberg, pp. 136-148.
42. Hadjioloff, A.I., E. Zvetkova, L. Kancheva, S. Yanev, Y. Martinova, M. Veltcheva. Incorporation of labelled biogenic amines and their precursors in the skin of amphibia-pigment cells. Compt Rend Acad Bulg Sci 1980; 33: 1123-1126.
43. Hadjioloff, A. I., L. Kancheva, Y. Martinova, E. Zvetkova, M. Veltcheva. Autoradiographic study of catecholamine metabolism in amphibian dermis. Folia Morphologica 1981; 29: 56-58.
44. Hadjioloff A. I., M. S. Veltscheva, Y. S. Martinova, E. Zvetkova, L. S. Kancheva, S. G. Yanev. Recherches autoradiographiques sur la synthese du melanine dans la peau et dans le foie d'Amphibia. Arch Union Med Balk Bukarest) 1983; 21: 90-93.
45. Zvetkova E., A. I. Hadjioloff, M. Anastassova-Kristeva, L. Kancheva. Uptake of P in autofluorescent calcified structures of amphibian dermis. Compt Rend Acad Bulg Sci 1979; 30: 1351.
46. Werner-Felmayer, G., E.R. Werner, D. Fuchs, A. Hausen, G. Reibnegger, H. Wachter. Tumour necrosis factor-a and lipopolysaccharide enhance interferon-induced tryptophan degradation and pteridine synthesis in human cells. Biol Chem Hoppe-Seyler 1989; 370: 1063-1069.
47. Shivatcheva, T., A. I. Hadjioloff, A. Dikov. In vitro blast transformation of lymphocytes under the action of ranopterines. Compt Rend Acad Bull Sci 1982; 35: 1439-1442.
48. Tschesche R., Korte F. Die Konstitution des Ichthyopterins. Chem Berichte 1951; 84: 801-809.
49. Zvetkova E., E. Janeva, E. Nikolova, et al. Hemopoietic colony-stimulating activity of ranopterines in murine bone marrow agar cultures. Compt Rend Acad Bulg Sci 1991; 44: 91-94.
50. Zvetkova E., E. Ianeva, A. Dikov, A. I. Hadjioloff. Ranopterine with MG-CSF-like activity in murine bone marrow agar cultures. Cell Prolif 1992; 25: 498.
51. Zvetkova E., I. Tsenov, E. Katzarova, et al. In vitro proliferation of mouse bone marrow lymphocytes and stromal macrophages under the biological action of ranoptarin (neopterin). Compt Rend Acad Bulg Sci 1995; 48: 81-84.
52. Zvetkova, E., E. Katzarova, I. Chowdhury, et al. Activation and NO secretion pattern of murine macrophage subpopulations after in vivo administration of ranopterin neopterin. Comp Rend Acad Bulg Sci 1996; 49: 113-116.
53. Zvetkova, E., R. Toschkova, K. Kovatcheva, et al. Lymphoproliferation and immune response induced by ranopterin neopterin in mice. Compt Rend Acad Bulg Sci 1996; 49: 117-120.
54. Zvetkova E., E. Katzarova, E. Ianeva, et al. CSA production in murine long term bone marrow cultures after in vitro treatment with ranopterines. Acta Morphologica et Anthropologica 1997; 4: 59-61.
55. Zvetkova E., R. Toshkova, V. Ralchevsky, et al. Protective effect of ranopterin neopterin on experimentally induced Graffi tumours in hamsters. Pteridines 1998; 9: 196-200.
56. Zvetkova E., Jelinek J. Methylene blue-fast green staining of hemopoietic colonies in agar cultures. Gegenbaurs Morphol Jahrb 1989; 135: 779-793.
57. Schoedon, G., J. Troppmair, A. Fontana, C. Huber, H.C. Curtius, A. Niederwieser. Biosynthesis and metabolism of pterins in peripheral blood mononuclear cells andleukemia lines of man and mouse. Eur J Biochem 1987; 166: 303-310.
58. Milstein S., S. Kaufman, K. Tanaka. In: Chemistry and Biochemistry of Pteridines (Eds. H.-C. Curtius, S. Ghisla, N. Blau), Walter de Gruyter, Berlin-New York, 1990, pp. 505-510.
59. Jacobson W., D. Simpson. The fluorescence spectra of pterins and their possible use in the elucidation of the antipemicious anaemia factor. Biochem J 1946; 40: 9-14.
60. Benabdallah K., Boivin P., Dhermy D. The synthesis and accumulation of membrane protein 4.1 in Friend erythroleukaemia cells. Biol Cell 1991; 71: 273-280.
61. Taraboletti, G., P. Borsotti, R. Chirivi, et al. Effect of all trans-retinoid acid (ATRA) on the adhesive and motility properties of acute promyelocytic leukemia cells. Int J Cancer 1997; 70: 72-77.
62. Zimmerman G.A., S.M. Prescott, T.M. McIntyre. Endothelial cell interactions with granulocytes: lethering and signaling molecules. Immunol Today 1992; 13: 93-99.
63. Fuchs, D., A. Hausen, G. Reibnegger, E.R. Werner, M.P. Dierich, H. Wachter. Neopterin as marker for activated cell-mediated immunity:application in HIV infection. Immunol Today 1988; 9: 150-155.
64. Luna-Casado L., A. Diez-Ruiz, F. Gutierrez-Gea, et al. Increased mononuclear cells expression of adhesion molecules in alcoholic cirrhosis:its relation to immune activation. J Hepatology 1997; 27: 477-483.
65. Tilz G., A. Diez-Ruiz, G. Baier-Bitterlich, U. Demel, H. Wachter, D. Fuchs. Soluble receptors for tumor necrosis factor and neopterin as parameters of cell-mediated immune activation. Hematology 1996; 1: 141-154.
66. Hoffmann G., S. Frede, S. Kenn, et al. Neopterin-induced Tumor Necrosis Factor-a synthesis in vascular smooth muscle cells in vitro. Int Arch Allergy Immunol 1998; 116: 240-245.
67. Zangerle R., S. Steinhuber, M. Sarcletti, et al. Serum HIV-1 RNA levels compared to soluble markers of immune activation to predict disease progression in HIV-1-infected individuals. Int Arch Allergy Immunol 1998; 116: 228-239.
68. Denefle J. P., Q. L. Zhu, J. P. Lechaire. Dermal tracts in frog skin: fibronectin pathways for cell migration. Biology of the Cell 1987; 59: 219-226.
69. Iwata, A., M. Iwata, E. Nakano. Fibronectin-induced migration of melanophores in vitro in skales of medaka Oryzias latipes. Cell Tissue Res 1984; 238: 509-513.
70. Rieder, J., W.Schobersberger, D.Fuchs, et al. Neopterin induces intercellular adhesion molecule-1 expression in rat alveolar epithelial cells L2. Pteridines, in press.
71. Busnel, R., P. Chauchard, H. Mazone, et al. Action de la fluorescence et de lacide isoxanthopterine carboxylique sur les test d,avitaminose B1 du pigeon et du flagelle Polytomella caeca. C R Acad Sci 1944; 218: 609-610.
72. Huber C., R. Batchelor, D. Fuchs, et al. Immune response associated production of neopterin: Release from macrophages primarily under control of interferon-gamma. J Exp Med 1984; 165: 310-316.
73. Wachter, H., D. Fuchs, A. Hausen, G. Reibnegger, G. Weiss, E. R. Werner, G. Werner-Felmayer. Neopterin: Biochemistry, methods, clinical application. Berlin-New York, Walter de Gruyter, 1992, pp. 1-294.
74. Fuchs D., T. Spira, A. Hausen, et al. Neopterin as a predictive marker for disease progression in human immunodeficiency virus type I infection. Clin Chem 1989;35:1746-1749.
75. Fuchs D., G. Weiss, G. Reibnegger, et al. The role of neopterin as a. monitor of cellular immune activation in transplantation, inflammatory, infectious and malignant diseases. Crit Rev Clin Lab Sci 1992; 29: 307-341.
76. Reibnegger, G., D. Fuchs, D. Fuith, et al. Neopterin as a marker for activated cell-mediated immunity: application in malignant disease. Cancer Detect Prevent 1991; 15: 483-490.
77. Tilz G., A. Diez-Ruiz, G. Baier-Bitterlich, et al. Soluble receptors for tumor necrosis factor and neopterin as parameters of cellmediated immune activation. ACI International 1997; 9: 110-118.
78. Baier-Bitterlich, G., D. Fuchs, R. Zangerle, et al. trans-Activation of the HIV type 1 promoter by 7,8-dihydroneopterin in vitro. AIDS Res Human Retroviruses 1997; 13: 173-178.
79. Baier-Bitterlich G., D. Fuchs, H. Wachter. Chronic immune stimulation, oxidative stress, and apoptosis in HIV infection. Biochem Pharmacol 1997; 53: 755-763.
80. Spring M., Ch. Stahl-Hennig, Th. Nisslein, et al. Suppression of viral replication in a long-term nonprogressing Rhesus Macaque experimentally infected with pathogenic Simian Immunodeficiency Virus (SIV). Clin Immunol Immunopathol 1998; 87: 101-105.
81. Wachter, H., D. Fuchs, A. Hausen, et al. Neopterin as marker for activation of cellular immunity: Immunologic basis and clinical application. Adv Clin Chem 1989; 27: 81-141.
82. Blau N., D. Schoedon, H. C. Curtius. Biosynthesis and significance of neopterin in the immune system. Europ J Cancer Clin Oncol 1989; 25: 603-605.
83. Bitterlich G., G. Szabo, E.R. Werner, et al. Selective induction of mononuclear phagocytes to produce neopterin by interferons. Immunobiology 1988;176:228-235.
84. Werner E.R., G. Werner-Felmayer, D. Fuchs, et al. Parallel induction of tetrahydrobiopterin biosynthesis and and indoleamine 2,3-dioxygenase activity in human cells and cell lines by interferon-g. Biochem J 1989; 262: 861-866.
85. Werner E. R., G. Werner-Felmayer, D. Fuchs, et al. Tetrahydrobiopterin biosynthetic activities in human macrophages, fibroblastsTHP-1 and T-24 cells. J Biol Chem 1990; 265: 3189-3192.
86. Altindag Z., G. Werner-Felmayer, G. Sahin, H.Wachter, D. Fuchs. Colchicine derivatives inhibit neopterin production in human peripheral blood mononuclear cells (HBMC). Clin Exp Immunol 1997; 107: 574-577.
87. Schobersberger, W., G. Hoffmann, J. Grote, H. Wachter, D. Fuchs. Induction of inducible nitric oxide synthase expression by neopterin in vascular smooth muscle cells. FEBS Lett 1995; 377: 461-464.
88. Hoffmann G., W. Schobersberger, S. Frede, et al. Neopterin activates transcription factor nuclear factor-kB in vascular smooth muscle cells. FEBS Lett 1996; 391: 181-184.
89. Wirleitner, B., G. Baier-Bitterlich, G. Hoffmann, et al. Neopterin derivatives to activate NF-kB. Free Radical Biol Med 1997; 23: 177-178.
90. Kojima, S., T. Icho, H. Mori, T. Arai. Enhancing potency of neopterin toward B-16 melanoma cell damage induced by UV-A irradiation and its possible applications for skin tumor treatment. Anticancer Res 1995; 15: 1975-1980.
91. Fuchs, D., G. Baier-Bitterlich, I. Wede, H. Wachter. Reactive oxygen and apoptosis. In: Oxidative Stress and the Molecular Biology of Antioxidant Defenses. Cold Spring Harbor Laboratory Press, 1997, 139-167.
92. Albina, J. E., S. Cui, R. B. Mateo, J. S. Reichner. Nitric oxide-mediated apoptosis in murine peritoneal macrophages. J Immunol 1993; 150: 5080-5085.
93. Schobersberger, W., G. Hoffmann, P. Hobisch-Hagen, et al. Neopterin and 7,8-dihydroneopterin induce apoptosis in the rat alveolar epithelial cell line L2. FEBS Lett 1996; 397: 263-268.
94. Hoffmann G., S. Kenn, B. Wirleitner, et al. Neopterin induces nitric oxide-dependent apoptosis in rat vascular smooth muscle cells. Immunobiology 1998; 199: 63-73.
95. Baier-Bitterlich, G., D. Fuchs, C. Murr, et al. Effect of neopterin and 7,8-dihydroneopterin on tumor necrosis factor-a induced programmed cell death. FEBS Lett 1995; 364: 234-238.
96. Diez-Ruiz, A., G.P. Tilz, R. Zangerle, G. Baier-Bitterlich, H. Wachter, D. Fuchs. Soluble receptors for tumor necrosis factor in clinical laboratory diagnosis. Eur J Haematol 1995; 54: 1-8.
97. Zvetkova E., S. Koshucharov, A. I. Hadjioloff. Cytochemistry of nucleoproteins (RNP and DNP) and some cationic proteins in the peripheral blood leukocytes of patients with lung cancer. Folia Haematol 1979; 106: 205-223.
98. Zvetkova E., G. Kostov, A. I. Hadjioloff, I. Zvetkov. Sur la cytochimie des leucocytes chez les cancereux et les precancereux. Arch Union Med Balk 1984; 22: 140-142.
99. Zvetkova E., I. Zvetkov. A cytological method for the simultaneous staining of nucleoproteins and some cationic proteins. Acte Histochem 1976; 57: 1-13.