Abstract
Malignant melanomas are tumours in which one metabolic pathway — such as that used for the formation of a pigment — is conspicuously accentuated in comparison with normal homologous tissues. This accentuation has been investigated by many authors who studied mainly the relation to the final product — melanin — and to the main catalyst of its formation — tyrosinase. However, it is surprising that little attention has been devoted to the actual course of the reaction and to the formation of the intermediates in vivo. Almost all the existing conclusions in this direction were in fact based only on analogies with model reactions in vitro. Nevertheless, already in the past century the socalled melanogens — precursors of melanin — or their metabolites were described in the malignant melanoma in urine 1). There is no doubt that the elucidation of the chemical structure, biogenesis and metabolism of these compounds can contribute substantially to the more detailed knowledge of melanogenesis in vivo and thus to a better knowledge of the biochemistry of malignant melanoma in general.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Andén, N.-E., B.-E. Ross, and B. Werdinius: On the occurence of homovanillic acid in brain and cerebrospinal fluid and its determination by a fluorometric method. Life Sci. 448–458 (1963).
Anderson, A. B.: Urinary melanogens. Biochem. J. 83, 10 P (1962).
Atkinson, M. R.: Isomeric methoxyindolyl glucosiduronic acids in melanotic urine. Biochim. Biophys. Acta 74, 154–155 (1963).
Axelrod, J., and A. B. Lerner: 0-Methylation in the conversion of tyrosine to melanin. Biochim. Biophys. Acta 71, 650–655 (1963).
Buns, M. S., and R. F. Kallman: The incorporation of C14 from 3,4-dihydroxyphenylalanine-2’-14C into the melanin of mouse melanoma. Cancer Res. 24, 863–868 (1964).
Bouchilloux, S., and A. Kodja: Oxydation chimique ou enzymatique de la 3,4-dihydroxy-L-phénylalanine, de l’hydroxytyramine et de la noradrénaline étudiée par chromatographie et électrophorèse sur papier. Bull. Soc. Chim. Biol. 42, 65–82 (1960).
Ducholâ J.: Tyrosine metabolism in melanoma. Nature 194: 976 (1962).
Ducholâ J., and V. Gregora: Homovanillic acid in its relation to tyrosine metabolism in melanoma. Clin. Chim. Acta 7, 443–446 (1962).
Ducholâ J., and Z. Pechan: The biochemical and clinical significance of melanogenuria. In The Pigment Cell. Ann. N. Y. Acad. Sci. 100, 1048–1068 (1963).
Ducholâ J., and Z. Pechan: The chemical nature of some DOPA metabolites in melanoma. Sixth International Congress of Biochemistry, New York 1964. Abstracts V-A-5, p. 390.
Ducholâ J., and Z. Pechan: Biochemie melaninii a melanogenese. Praha: Stâtni zdravotnické nakladatelstvi 1964.
Duliére, W. L., and H. S. Raper: The tyrosinase-tyrosine reaction. VII. The action of tyrosinase on certain substances related to tyrosine. Biochem. J. 24, 239–245 (1930).
Hempel, K., und M. Deimel: Untersuchungen zur gezielten Strahlentherapie des Melanoms und des chromaffinen Systems durch selektive H-3-Inkorporation nach Gabe von H-3-markiertem DOPA. Strahlentherapie 121, 22–45 (1963).
Jepson, J. B.: Indoles and related Ehrlich reactors. In Chromatographic and Electrophoretic Techniques (Ed. Smith, I.) Vol. I, p. 183–211. London: W. Heinemann 1960.
Leonhard, G.: Zum Mechanismus der Thormählenschen Reaktion. Naturwissenschaften 40, 621–622 (1953).
Leonhard, G.: Papierchromatographische Trennung von Harnmelanogenen. Naturwissenschaften 41, 141 (1954).
Leonhard, G.: Zur Charakterisierung der Harnmelanogene. Naturwissenschaften 41, 305–306 (1954).
Leonhard, G.: Ober Struktur und Lichtabsorption der Harnmelanogene. Naturwissenschaften 42, 17–18 (1955).
Leonhard, G.: Zur Biochemie der Melanogenese beim malignen Melanom. Med. Fak. Univ. Frankfurt a. M.: Habilitationsschrift 1954.
Linnell, L., and H. S. Raper: The chromogen of melanuria. Biochem. J. 29, 76–85 (1935).
Nicolaus, R. A., M. Piattelli, and E. Fattorusso: The structure of melanins and melanogenesis. IV. On some natural melanins. Tetrahedron 20, 1163–1172 (1964).
Pechan, Z.: Isolate a charakterisace indolvÿch melanogend z moue. Oncolog. Res. Inst. Brno: Dissertation 1963.
Pechan, Z., and J. Duchon: Occurrence, isolation and metabolic relations of urinary melanogens in patients affected by melanoma. Acta Unio Internat. contra Cancrum 20, 1081–1084 (1964).
Raper, H. S.: The tyrosinase-tyrosine reaction. VI. Production from tyrosine of 5,6-dihydroxyindole and 5,6-dihydroxyindole-2-carboxylic acid — the precursors of melanin. Biochem. J. 21, 89–96 (1927).
Scott, J. A.: 3,4-dihydroxyphenylalanine (DOPA) excretion in patients with malignant melanoma. Lancet 861–862 (1962).
Shaw, K. N. F., A. Mcmillan, and M. D. Armstrong: The metabolism of 3,4-dihydroxyphenylalanine. J. Biol. Chem. 226, 255–266 (1957).
Srunnitz, W. v.: Ober die Ausscheidung der 3-Methoxy-4-hydroxyphenylessigsäure (Homovanillinsäure)beim Neuroblastom und anderen neuralen Tumoren. Klin. Wochenschrift 40, 163–167 (1962).
Srunnitz, W. v.: Occurrence, isolation and identification of 3-methoxy-4-hydroxyphenylalanine. Clin. Chim. Acta 6, 526–530 (1961).
Swan, G. A.: Chemical structure of melanins. In The Pigment Cell. Ann. N. Y. Acad. Sci. 100, 1005–1019 (1963).
Swan, G. A.: Some studies on the formation and structure of melanins. Rend. Accad. Sci. Fis. Mat. Soc. Naz. Sci. Let. Arti, Napoli. Serie 4, Vol. XXXI, p. 1–20, 1964.
Tannhauser, S. J., und S. Weiss: Ober das Melanogen bei melanotischen Tumoren und seinen Zusammenhang mit der normalen Pigmentbildung. Verhandl. d. Deutsch. Gesell. f. inn. Med.Kongr. 34, 156–160, 1922.
Williams, C. M.: Gas chromatography of urinary aromatic acids. Analyt. Biochem. 4, 423–431 (1962).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1966 Springer-Verlag Berlin · Heidelberg
About this paper
Cite this paper
Duchoň, J., Matouš, B., Pechan, Z. (1966). On the Chemical Nature of Urinary Melanogens. In: Porta, G.D., Mühlbock, O. (eds) Structure and Control of the Melanocyte. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-99906-2_20
Download citation
DOI: https://doi.org/10.1007/978-3-642-99906-2_20
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-99908-6
Online ISBN: 978-3-642-99906-2
eBook Packages: Springer Book Archive