Τόμος 3 (1989) – Τεύχος 1 – Άρθρο 2 – Επιθεώρηση Κλινικής Φαρμακολογίας και Φαρμακοκινητικής-Διεθνής Έκδοση – Volume 3 (1989) – Issue 1 – Article 2 – Epitheorese Klinikes Farmakologias και Farmakokinetikes-International Edition

Title On the action of lucanthone and its analogue hycanthone
Author Maria Pelecanou and Panayotis Catsoulacos

Laboratory of Pharmaceutical Chemistry, University of Patras, Greece

Citation Pelecanou, M., Catsoulacos, P.: On the action of lucanthone and its analogue hycanthone, Epitheorese Klin. Farmakol. Farmakokinet. 3(1): 13-21 (1989)
Publication Date 1989-07
Full Text Language English
Order – Buy Ηλεκτρονική Μορφή: pdf (10 €)Digital Type: pdf (10 €)

pharmakonpress[at]pharmakonpress[.]gr

Keywords Lucanthone, hycanthone, metabolism, Schistosoma mansoni, Schistosoma haematobium, DNA, carcinostatic effectiveness.
Other Terms review article
Summary Lucanthone, the 1 -[2- (diethyfamino) ethylamino]-4- methyl-10-thioxanthenone, was the first non-antimoniaf drug active against Schistosoma mansoni and Schistosoma haematobium. Lucanthone is not effective per se, but is metabofically converted by the host into its 4-hydroxymethyi analogue, hycanthone, which is considered the therapeutically active substance. Studies on the pharmacological properties of lucanthone and hycanthone have revealed a variety of effects on muscular activity and neurotransmitter systems of schistosomes as well as on nucleic acid and protein biosynthesis. Both drugs are capable of binding to DNA in organisms and animal cells in vitro. Lucanthone and hycanthone have also shown carcinostatic effectiveness against a variety of mouse tumors and exhibited mutagenic activity in bacterial and mammalian cell systems. Lucanthone has proven to be a potent teratogen in mice and rabbits. This article comprises the basic references on the action of lucanthone and hycanthone.
References 1.         Woolhouse, N.M.: Biochemical and pharmacological effects in relation to the mode of action of antischistosomal drugs. Biochem. Pharmacol. 28: 2413 (1979)

2.         Kikuth, W., Gonnert, R.: Experimental studies on the therapy of schistosomiasis. Ann. Trop. Med. Parasitoi 42: 256 (1948)

3.         Archer, S.: The chemotherapy of schistosomiasis. Ann. Rev. Pharmacol. Toxicol. 25: 485 (1895)

4.         Rosi, D., Peruzzoti, G., Dennis, E.W., Berberian, D.A., Freele, H., Archer, S.: A new active metabolite of “Miracil D”. Nature 208: 1005 (1965)

5.         Rosi, D., Peruzzoti, G., Dennis, E.W., Berberian, D.A., Freele, H., Tullar, B.F., Archer, S.: Hycanthone, a new active metabolite of lucanthone. J. Med. Chem. 10: 867 (1967)

6.         Pica-Mattoccia, L, Lelli, A., Cioli, D.: Sex and drugs in Schistosoma mansoni. J. Parasitoi. 68: 347 (1982)

7.         Yarinsky, A., Hernandez, P., Ferrari, R.A., Freele, H.W.: Effects of hycanthone against two strains of S. japonicum in mice. Jap. J. Parasitoi. 21: 101 (1972)

8.         Hirschberg, E.: Thioxanthenones: Miracil D and hycanthone. In: Mechanism of Action of Antimicrobial and Antitumor Agents (J.W. Corcoran and F.E. Hahn, eds), p. 274. Springer-Verlag, Berlin, Heidelberg, 1975

9.         Hartman, P.E., Levine, E., Hartman, Z., Berger, H.: Hycanthone a frameshift mutagen. Science 172: 1058 (1971)

10.       Moore, J.A.: Teratogenicity of hycanthone in mice. Nature 107: 239 (1972)

11.       Sieber, S.M., Adamson, R.H.: Evaluation of the teratogenic activity of hycanthone in mice and rabbits. J. Toxicol. Environ. Health 1: 309 (1975)

12.       Haese, W.H., Smith, D.L., Bueding, E.: Hycanthone-in- duced hepatic changes in mice infected with Schistosoma mansoni. J. Pharmacol. Exp. Ther. 186: 430 (1973)

13.       Yarinsky, A., Drobeck, H.P., Freele, H., Wiland, J., Gumaer, K.L.: An 18-month study of parasitologenic and tumorigenic effects of hycanthone in Schistosoma mansoni-infected and non-infected mice. Toxicol. Appi Pharmacol. 27: 169 (1974)

14.       Neidle, S.: Nucleic acid binding drugs: The structure of Miracil D, a DNA binding drug. Biochim. Biophys. Acta 454: 207 (1976)

15.       Mauss, H.: Ober basisch substituierte Xanthon- und Thioxanthon- Abkommlinge; Miracil, ein neues Chemotherapeuticum. Chem. Ber. 81: 19 (1948)

16.       Archer, S., Suter, C.M.: The preparation of some 1-alkylamino- and dialkylaminoalkylaminothioxanthones. J. Am. Chem. Soc. 74: 4296 (1952)

17.       Cioli, D., Knopf, P.M.: A study of the mode of action of hycanthone against Schistosoma mansoni in vivo and in vitro. Am. J. Trop. Med. Hyg. 29: 220 (1980)

18.       Gonnert, R.: The structure-activity relationship in several schistosomicidal compounds. Bull. Wld Hlth Org. 25: 702 (1961)

19.       Yarinsky, A., Hernandez, P., Dennis, E.W.: The uptake of tritiated hycanthone by male and female Schistosoma mansoni worms and distribution of the drug in plasma and whole blood of mice following a single intramuscular injection. Bull. Wld Hlth Org. 42: 445 (1970)

20.       Hernandez, P., Dennis, E.W., Farah, A.: Metabolism of the schistosomicidal agent hycanthone by rats and rhesus monkeys. Bull. Wld Hlth Org. 45: 27 (1971)

21.       Tomosky-Sykes, T.K., Budeing, E.: Effects of hycanthone on neuromuscular systems of Schistosoma mansoni. J. Parasitol. 63: 259 (1977)

22.       Hillman, G.R„ Senft, A.W.: Anticholinergic properties of the antischistosomal drug hycanthone. Am. J. Trop. Med. Hyg. 24: 827 (1975)

23.       Hillman, G.R., Gibler, W.B.: Acetylcholine receptors in Schistosoma mansoni: Visualization and blockade by hycanthone. Biochem. Pharmacol. -24: 1911 (1975)

24.       Senft, A.W., Hillman, G.R.: Hycanthone effects on schistosomes and its likely mode of action. In; Biochemistry of Parasites and Host-parasite Relationships (H. Van den Bossche, ed.), p. 619, Elsevier/North-Holland, Amsterdam, 1976

25.       Pica-Mattpccia, L., Cioli, D.: Lack of correlation between schistosomicidal and anticholinergic properties of hycanthone and related drugs. J. Parasitol. 72: 531 (1976)

26.       Kim, R.A., Lukacs, J., Tanaka, R.D., Macinnis, A.J.: Effects of hycanthone and praziquantel on monoamine oxidase and cholinesterases in Schistosoma mansoni. J. Parasitol. 67: 20 (1981)

27.       Cioli, D., Pica-Mattoccia, L., Rosenberg, S., Archer, S.: Evidence for the mode of antischistosomal action of hycanthone. Life Sci. 37: 161 (1985)

28.       Pica-Mattoccia, L., Cioli, D., Archer, S.: Schistosomicides and DNA functioning. Biochem. Soc. Trans. 15: 70 (1987)

29.       Cioti, D., Pica-Mattoccia, L.: Genetic analysis of hycanthone-resistance in Schistosoma mansoni. Am. J. Trop. Med. Hyg. 33: 80 (1984)

30.       Carchman, R., Hirschberg, E., Weinstein, B.I., Miracil D.: Effect on the viscocity of DNA. Biochem. Biophys. Acta 179: 158 (1969)

31.       Hirschberg, E., Weinstein, I.B., Gersten, N., Marner, E., Finkelstein, T., Carchman, R.: Structure-activity studies on the mechanism of action of Miracil D. Cancer Res. 28: 60 (1968)

32.       Weinstein, I B. Chernoff, R., Finkelstein, I., Hirschberg. E.: An inhibitor of ribonucleic acid synthesis in Bacillus Subtilis. Mot. Pharmacol. 1: 297 (1965)

33.       Weinstein, I.B., Carchman, R. (Marner, E., Hirschberg, E., Miracil D.: Effects on nucleic acid synthesis, protein synthesis and enzyme induction in Escherichia coli. Biochim. Biophys. Acta 142: 440 (1967)

34.       Bases, R., Mendez, F.: Reversible inhibition of ribosomal RNA synthesis in HeLa by lucanthone with continued synthesis of DNA-like RNA. J. Cell. Physiol. 74: 283 (1969)

35.       Wittner, M., Tanowitz, H., Rosenbaum, M.: Studies with the schistosomicide hycanthone. Inhibition of macromolecular synthesis and its .reversal. Exp. Mot. Pathol. 14: 124 (1971)

36.       Obe, G.: Distribution of miracil-D-induced achromatic lesions and chromatid breaks on the chromosomes of human leukocytes. Z. Naturforsch. 25: 115 (1970)

37.       Simoni, I.C., Mello, M.L.S.: Investigation of hycanthone binding to DNA in chromatin with different supra-organization, composition and function. Acta Histochem. 79: 97 (1986)

38.       Waring, M.: Binding of drugs to supercoiled circular DNA; Evidence for and against intercalation. In: Progress in Molecular and Sucellular Biology (F.E. Hahn, ed.), Vol. 2, p. 216, Springer-Verlag, New York, 1971

39.       Sarma, M.H., Mitra, C.K., Sarma, R.H., Miller, K.J., Archer, S.: Interaction between double stranded poly(dA- df).poly(dA-dT) and lucanthone. Biochem. Biophys. Res. Comm. 94: 1285 (1980)

40.       Hartman, P.E., Hulbert, P.B.: Genetic activity spectra of some antischistosomal compounds with particular emphasis of thioxanthenones and benzothiopyranoindazoles. J. Toxicol. Environ. Health 2: 243 (1975)

41.       Hirschberg, E., Gellhorn, A., Murray M.R., Elslager, E.F.: Effects of Miracil D, Amodiaquin and a series of other 10-thiaxanthenones and 4-aminoquinolines| against a variety of experimental tumors in vitro and in vivo. J. Natl. Cancer Inst. 22: 567 (1959)

42.       Blanz, E.J. Jr., French, F.A.: A systematic investigation of thiaxanthen-9-ones and analogs as potential antitumor agents. J. Med, Chem. 6: 185 (1963)

43.       Reztsova, V.V., Goryukhina, T.A., Seits, I.F.: Molecular mechanism of the antitumor effects of lucanthone. Vopr. Onkol. 24: 91 (1978)

44.       Oswald, H., Youssef, M.: Overadditive synergism between the intercalators mitoxanthrone and lucanthone in advanced L1210 and P388 leukemia. J. Cancer Res. Clin. Oncol. 111: 137 (1986)

45.       Hischberg, E., Brindle, S.D., Semente, G.: Development and properties of mouse leukemia LI 210 resistant to Miracil D. Cancer Res. 24: 1733 (1964)

46.       Hirschberg, E.: In: Antibiotics (J.W. Corcoran and F.E. Hahn, eds). Vol. Ill, p. 274, Springer-Verlag, Berlin and Heidelberg, 1974

47.       Archer, S., Miller, K.J., Rej, R., Periana, C., Fricker, L: Ring-hydroxylated analogues of lucanthone as antitumor agents. J. Med. Chem. 25: 220 (1982)

48.       Archer, S., Zayed, A.-H., Rej, R., Rugino, T.A.: Analogues of hycanthone and lucanthone as antitumor agents. J. Med. Chem. 26: 1240 (1983)

49.       Archer, S., Pica-Mattoccia, L., Cioli, D., Seyed-Mozaffari, A., Zayed, A.-H.: Preparation and antischistosomal and antitumor activity of hycanthone and some of its congeners. Evidence for the mode of action of hycanthone. J. Med Chem. 31: 254 (1988)

50.       Clive, D., Flamm, W.G., Machesko, M.R.: Mutat. Res. 14: 262 (1972)

51.       Kramers, P.G.N.: Mutagenicity of hycanthone in Drosophila: Additional results and a comparison with some analogs. Mutat. Res. 82: 111 (1981)

52.       Hulbert, P.B., Bueding, E. (Hartman, P.E.: Hycanthone analogs: dissociation of mutagenic effects from antischistosomal effects. Science 186: 647 (1974)

 

Relative Papers

Online ISSN 1011-6575

Άρθρα Δημοσιευμένα σε αυτό το Περιοδικό Καταχωρούνται στα:

Articles published in this Journal are Indexed or Abstracted in: • Chemical Abstracts • Elsevier’s Bibliographic Databases: Scopus, EMBASE, EMBiology, Elsevier BIOBASE SCImago Journal and Country Rank Factor

Τι είναι η Επιθεώρηση Κλινικής Φαρμακολογίας και Φαρμακοκινητικής-Διεθνής Έκδοση-Οδηγίες προς τους Συγγραφείς –
What is Epitheorese Klinikes Farmakologias
και Farmakokinetikes-International Edition-Instrunctions to Authors

Άρθρα Δημοσιευμένα στην Επιθεώρηση Κλινικής Φαρμακολογίας και Φαρμακοκινητικής-Διεθνής Έκδοση –
Articles Published in Epitheorese Klinikes Farmakologias
και Farmakokinetikes-International Edition

Συντακτικη Επιτροπή-Editorial Board

ΕΤΗΣΙΑ ΣΥΝΔΡΟΜΗ 1989 – ANNUAL SUBSCRIPTION 1989
Γλώσσα Πλήρους Κειμένου – Full Text Language Αγγλικά, Γαλλικά – English, French
Παραγγελία – Αγορά – Order – Buy Ηλεκτρονική Μορφή: pdf (70 €) – Digital Type: pdf (70 €)

pharmakonpress[at]pharmakonpress[.]gr

Έντυπη Μορφή (70 € + έξοδα αποστολής) – Printed Type (70 € + shipping)

pharmakonpress[at]pharmakonpress[.]gr

 

 

Bookmark the permalink.

Comments are closed.