7
Views
40
CrossRef citations to date
0
Altmetric
Original Articles

Genetic activity spectra of some antischistosomal compounds, with particular emphasis on thioxanthenones and benzothiopyranoindazoles

&
Pages 243-270 | Received 15 Jan 1975, Accepted 25 Apr 1975, Published online: 20 Oct 2009

References

  • Ames , B. N. 1971 . “ The detection of chemical mutagens with enteric bacteria ” . In Chemical mutagens: Principles and methods for their detection , Edited by: Hollaender , A. vol. 1 , 267 – 282 . New York : Plenum Press .
  • Ames , B. N. 1973 . Carcinogens are mutagens: Their detection and classification . Environ. Health Perspect. , : 115 – 118 .
  • Ames , B. N. Carcinogens are mutagens: A simple method for detection . Proc. XIth Int. Cancer Congress . October , Florence/Perugia.
  • Ames , B. N. and Whitfield , H. J. Jr. 1966 . Frameshift mutagenesis in Salmonella . Cold Spring Harbor Symp. Quant Biol. , 31 : 221 – 225 .
  • Ames , B. N. , Hartman , P. E. and Jacob , F. 1963 . Chromosomal alterations affecting the regulation of histidine biosynthetic enzymes in . Salmonella. J. Mol. Biol. , 7 : 23 – 42 .
  • Ames , B. N. , Gurney , E. G. , Miller , J. A. and Bartsch , H. 1972a . Carcinogens as frameshift mutagens: Metabolites and derivatives of 2‐acetyl‐aminofluorene and other aromatic amine carcinogens . Proc Nat. Acad. Sci. U.S. , 69 : 3128 – 3132 .
  • Ames , B. N. , Sims , P. and Grover , P. L. 1972b . Epoxides of polycyclic hydrocarbons are frameshift mutagens . Science , 176 : 47 – 49 .
  • Ames , B. N. , Durston , W. E. , Yamasaki , E. and Lee , F. D. 1973a . Carcinogens are mutagens: A simple test system combining liver homogenates for activation and bacteria for detection . Proc. Nat. Acad. Sci. U.S. , 70 : 2281 – 2285 .
  • Ames , B. N. , Lee , F. D. and Durston , W. E. 1973b . An improved bacterial test system for the detection and classification of mutagens and carcinogens . Proc. Nat. Acad. Sci. U.S. , 70 : 782 – 786 .
  • Bases , R. 1970 . Enhancement of X‐ray damage in HeLa cells by exposure to lucanthone (Miracil D) following radiation . Cancer Res. , 30 : 2007 – 2011 .
  • Bateman , A. J. and Epstein , S. S. 1971 . “ Dominant lethal mutations in mammals ” . In Chemical mutagens: Principles and methods for their detection , Edited by: Hollaender , A. vol. 2 , 541 – 568 . New York : Plenum Press .
  • Berberian , D. A. , Freele , H. , Rosi , D. , Dennis , E. W. and Archer , S. 1967 . Schistosomicidal activity of lucanthone hydrochloride, hycanthone and their metabolites in mice and hamsters . J. Parasitol. , 53 : 306 – 311 .
  • Berman , C. 1958 . Primary carcinoma of the liver . Adv. Cancer Res. , 5 : 55 – 96 .
  • Bicker , U. and Fischer , W. 1974 . Enzymatic aziridine synthesis from β‐aminoalcohols–A new example of endogenous carcinogen formation . Nature , 249 : 344 – 345 .
  • Borchert , P. , Miller , J. A. , Miller , E. C. and Shires , T. K. 1973a . 1'‐Hydroxysafrole, a proximate carcinogenic metabolite of safrole in the rat and mouse . Cancer Res. , 33 : 590 – 600 .
  • Borchert , P. , Wislocki , P. G. , Miller , J. A. and Miller , E. C. 1973b . The metabolism of the naturally occurring hepatocarcinogen safrole to 1'‐hydroxysafrole and the electrophilic reactivity of 1'‐acetoxysafrole . Cancer Res. , 33 : 575 – 589 .
  • Boyland , E. 1971 . “ Mercapturic acid conjugation ” . In Handbook of experimental pharmacology , Edited by: Brodie , B. B. and Gillette , J. R. vol. 28 , 585 New York : Springer‐Verlag . part 2
  • Brusick , D. J. and Zeiger , E. 1972 . A comparison of chemically induced reversion patterns of Salmonella typhimurium Saccharomyces cerevisiae mutants, using in vitro plate tests . Mutation Res. , 14 : 271 – 275 .
  • Bueding , E. , Fisher , J. and Bruce , J. 1973 . The antischistosomal activity of a chloroindazole analog of hycanthone in mice infected with Schistosoma mansoni . J. Pharmacol. Exp. Ther. , 186 : 402 – 407 .
  • Campbell , T. C. and Stoloff , L. 1974 . Implications of mycotoxins for human health . J. Agr. Food Chem. , 22 : 1006 – 1015 .
  • Cattanach , B. M. 1971 . “ Specific locus mutation in mice ” . In Chemical mutagens: Principles and methods for their detection , Edited by: Hollaender , A. vol. 2 , 535 – 539 . New York : Plenum Press .
  • Cavalli‐Sforza , L. L. and Bodmer , W. F. 1971 . The genetics of human populations , San Francisco : W. H. Freeman . chapter 3
  • Clive , D. 1973 . Recent developments with the L5178Y TK heterozygote mutagen assay system . Environ. Health Perspect. , : 119 – 125 .
  • Clive , D. 1974 . Mutagenicity of thioxanthenes (hycanthone, lucanthone and four indazole derivatives) at the TK locus in cultured mammalian cells . Mutation Res. , 26 : 307 – 318 .
  • Clive , D. , Flamm , W. G. and Machesko , M. R. 1972 . Mutagenicity of hycanthone in mammalian cells . Mutation Res. , 14 : 262 – 264 .
  • Clive , D. , Flamm , W. G. and Patterson , J. B. 1973 . “ Specific‐locus mutational assay systems for mouse lymphoma cells ” . In Chemical mutagens: Principles and methods for their detection , Edited by: Hollaender , A. vol. 3 , 79 – 103 . New York : Plenum Press .
  • Cohen , S. S. 1971 . Introduction to the polyamines , Englewood Cliffs, N.J. : Prentice‐Hall .
  • Conner , T. , Stoeckel , M. and Legator , M. S. 1974 . Niridazole, a direct acting frameshift mutagen, not affected by microsomal enzyme preparation which can be detected in the host‐mediated assay . Mutation Res. , 26 : 456 (abstract)
  • Cook , T. M. and Goldman , C. K. 1975 . Hycanthone and its congeners as bacterial mutagens . J. Bacteriol. , 122 (2)
  • Corbin , K. W. and Uzzell , T. 1970 . Natural selection and mutation rates in mammals . Amer. Nat. , 104 : 37 – 53 .
  • Creech , H. J. , Preston , R. K. , Peck , R. M. , O'Connell , A. P. and Ames , B. N. 1972 . Antitumor and mutagenic properties of a variety of heterocyclic nitrogen and sulfur mustards . J. Med. Chem. , 15 : 739 – 746 .
  • Culvenor , C. C. J. , Downing , D.T. , Edgar , J. A. and Jago , M. V. 1969 . Pyrrolizidine alkaloids as alkylating and antimitotic agents . Ann. N. Y. Acad. Sci. , 163 : 837 – 847 .
  • DeBaun , J. R. , Miller , E. C. and Miller , J.A. 1970a . N‐Hydroxy‐2‐acetylaminofluorene sulfotransferase: Its probable role in carcinogenesis and in protein‐(methion‐S‐yl) binding in rat liver . Cancer Res. , 30 : 577 – 595 .
  • DeBaun , J. R. , Smith , J. Y. R. , Miller , E. C. and Miller , J.A. 1970b . Reactivity in vivo of the carcinogen N‐hydroxy‐2‐acetylaminofluorene: Increase by sulfate ion . Science , 167 : 184 – 186 .
  • Domingo , E. O. , Warren , K. S. and Stenger , R. J. 1967 . Increased incidence of hepatoma in mice with chronic schistosomiasis mansoni treated with a carcinogen . Amer. J. Pathol. , 51 : 307 – 321 .
  • Drake , J. W. 1970 . The molecular basis of mutation , 145 San Francisco : Holden‐Day .
  • Drake , J. W. 1975 . Environmental mutagenic hazards . Science , 187 : 504 – 514 .
  • Dreyfuss , J. and Monty , K. J. 1963 . Coincident repression of the reduction of 3'‐phosphoadenosine 5'‐phosphate, sulfite, and thiosulfate in the cysteine pathway of Salmonella typhimurium . J. Biol. Chem. , 238 : 3781 – 3783 .
  • Durston , W. E. and Ames , B. N. 1974 . A simple method for the detection of mutagens in urine: Studies with the carcinogen 2‐acetylaminofluorene . Proc. Nat. Acad. Sci. U.S. , 71 : 737 – 741 .
  • Ehling , U. H. 1970 . “ The multiple loci method ” . In Chemical mutagenesis in mammals and man , Edited by: Vogel , F. and Röhrborn , G. 156 – 161 . New York : Springer‐Verlag .
  • Enomoto , M. and Saito , M. 1972 . Carcinogens produced by fungi . Ann. Rev. Microbiology , 26 : 279 – 312 .
  • Fahmy , O. G. and Fahmy , M. J. 1972 . Mutagenic selectivity for the RNA‐forming genes in relation to the carcinogenicity of alkylating agents and polycyclic aromatics . Cancer Res. , 32 : 550
  • Flamm , W. G. 1973 . The role of repair in environmental mutagenesis . Environ. Health Perspect. , : 215 – 220 .
  • Friebel , H. 1973 . Drug safety in theory and practice . WHO Chronicle , 27 : 59 – 65 .
  • Generoso , W. M. and Cosgrove , G. E. 1973 . “ Total reproductive capacity in female mice: Chemical effects and their analysis ” . In Chemical mutagens: Principles and methods for their detection , Edited by: Hollaender , A. vol. 3 , 241 – 258 . New York : Plenum Press .
  • Gerchman , L. L. and Ludlum , D. B. 1973 . The properties of O6‐methylguanine in templates for RNA polymerase . Biochim. Biophys. Acta , 308 : 310 – 316 .
  • Gillham , B. 1971 . The reaction of aralkyl sulfate esters with glutathione catalysed by rat liver preparations . Biochem. J. , 121 : 667 – 672 .
  • Green , S. , Carr , J. V. , Sauro , F. M. and Legator , M. 1973a . Effects of hycanthone on spermatogonial cells, DNA synthesis in bone marrow and dominant lethality in rats . J. Pharmacol. Exp. Ther. , 187 : 437 – 443 .
  • Green , S. , Sauro , F. M. and Legator , M. S. 1973b . Cytogenic effects of hycanthone in the rat . Mutation Res. , 17 : 239 – 244 .
  • Gutman , H. R. , Malejka‐Giganti , D. , Barry , E. J. and Rydell , R. E. 1972 . On the correlation between the hepatocarcinogenicity of the carcinogen, N‐2‐fluorenylacetamide, and its metabolic activation by the rat . Cancer Res. , 32 : 1554 – 1561 .
  • Haese , W. H. , Smith , D. L. and Bueding , E. 1973 . Hycanthone‐induced hepatic changes in mice infected with Schistosoma mansoni . J. Pharmacol. Exp. Ther. , 186 : 430 – 440 .
  • Hansch , C. and Clayton , J. M. 1973 . Lipophilic character and biological activity of drugs. II: The parabolic case . J. Pharm. Sci. , 62 : 1 – 21 .
  • Hansch , C. and Dunn , W. J. 1972 . Linear relationships between lipophilic character and the biological activity of drugs . J. Pharm. Sci. , 61 : 1 – 19 .
  • Hartman , P. E. , Hartman , Z. , Stahl , R. C. and Ames , B. N. 1971a . Classification and mapping of spontaneous and induced mutations in the mutations in the histidine operon of Salmonella . Advan. Genet. , 16 : 1 – 34 .
  • Hartman , P. E. , Levine , K. , Hartman , Z. and Berger , H. 1971b . Hycanthone: A frameshift mutagen . Science , 172 : 1058 – 1060 .
  • Hartman , P. E. , Berger , H. and Hartman , Z. 1973 . Comparison of hycanthone (“Etrenol”), some hycanthone analogs, Myxin, and 4‐nitroquinoline‐1‐oxide as frameshift mutagens . J. Pharmacol. Exp. Ther. , 186 : 390 – 398 .
  • Hartman , P. E. , Hulbert , P. B. , Bueding , E. and Taylor , D. 1975 . Microsomal activation to mutagens of antischistosomal methyl thioxanthenes and initial tests on a possibly non‐mutagenic analogue . Mutation Res. , 31 : 87 – 95 .
  • Heidelberger , C. 1973 . Current trends in chemical carcinogenesis . Fed. Proc. , 32 : 2154 – 2161 .
  • Heinemann , B. 1971 . “ Prophage induction in lysogenic bacteria as a method of detecting potential mutagenic, carcinogenic, carcinostatic, and teratogenic agents ” . In Chemical mutagens: Principles and methods for their detection , Edited by: Hollaender , A. vol. 1 , 235 – 266 . New York : Plenum Press .
  • Heller , M. J. , Tu , A. T. and Maciel , G. E. 1974 . Interaction of Miracil D with double‐stranded poly (adenylic acid)‐poly (uridylic acid) . Biochemistry , 13 : 1623 – 1631 .
  • Hetrick , F. M. and Kos , W. L. 1973 . Transformation of Rauscher virus‐infected cell cultures after treatment with hycanthone and lucanthone . J. Pharmacol. Exp. Ther. , 186 : 425 – 429 .
  • Higginson , J. 1963 . The geographical pathology of primary liver cancer . Cancer Res. , 23 : 1624 – 1633 .
  • Hirschberg , E. , Brindle , S. D. and Semente , G. 1964 . Development and properties of mouse leukemia L1210 resistant to Miracil D . Cancer Res. , 24 : 1733 – 1737 .
  • Hirschberg , E. , Weinstein , I. B. , Gersten , N. , Marner , E. , Finkelstein , T. and Carchman , R. 1968 . Structure‐activity studies on the mechanism of action of Miracil D . Cancer Res. , 28 : 601 – 607 .
  • Howard‐Flanders , P. 1973 . DNA repair and recombination . British Med. Bull. , 29 : 226 – 235 .
  • Howe , R. 1965 . Carcinogenicity of “alderlin” (pronethalol) in mice . Nature , 207 : 594 – 595 .
  • Hulbert , P. B. , Bueding , E. and Robinson , C. H. 1973 . Structure and antischistosomal activity in the nitrofuran series. Requirement for a 5‐nitro‐2‐furyl‐vinyl moiety based on comparison of 3‐(5‐nitro‐2‐furyl)‐substituted propionic, acrylic and propiolic acid derivatives . J. Med. Chem. , 16 : 72 – 78 .
  • Hulbert , P. B. , Bueding , E. and Hartman , P. E. 1974 . Hycanthone analogs: Dissociation of mutagenic from antischistosomal effects . Science , 186 : 647 – 648 .
  • Isono , K. and Yourno , J. 1974 . Chemical carcinogens as frameshift mutagens: Salmonella DNA sequence sensitive to mutagenesis by polycyclic carcinogens . Proc. Nat. Acad. Sci. U.S. , 71 : 1612 – 1617 .
  • Jansma , W. B. , Hulbert , P. B. and Bueding , E. 1974 . Induction of hycanthone resistance in Schistosoma mansoni . Fed. Proc. , 33 ( 556 ) (Abstract)
  • Joshi , S. R. , Bishop , Y. and Epstein , S. S. 1973 . Reduced fertility in male mice following treatment with Niridazole . Experientia , 29 : 1253 – 1255 .
  • Kanazir , D. T. , Hartman , P. E. and Savic , D. 1970 . Ultraviolet‐induced reversions of Salmonella his frameshift mutations . J. Bacteriol. , 101 : 649 – 651 .
  • King , C. M. and Phillips , B. 1968 . Enzyme‐catalyzed reactions of the carcinogen N‐hydroxy‐2‐fluorenylacetamide with nucleic acid . Science , 159 : 1351 – 1353 .
  • Kirtikar , D. M. and Goldthwait , D. A. 1974 . The enzymatic release of O'‐methylguanine and 3‐methyladenine from DNA reacted with the carcinogen N‐methyl‐N‐nitrosourea . Proc Nat. Acad. Sci. U.S. , 71 : 2022 – 2026 .
  • Knaap , A. G. A. C. and Kramers , P. G. N. 1974 . Mutagenicity of hycanthone in Drosophlla melanogaster . Mutation Res. , 22 : 55 – 62 .
  • Knudson , A. G. Jr. , Strong , L. C. and Anderson , D. E. 1973 . Heredity and cancer in man . Prog. Med. Genetics , 9 : 113 – 158 .
  • Kohn , H. I. and Melvold , R. W. Temporal variations in spontaneous mutation‐rate of the histocompatibility loci of the mouse . Paper presented at the 5th Annual Meeting Environ. Mut. Soc. March 8–11 .
  • Lawley , P. D. 1974 . “ Alkylation of nucleic acids and mutagenesis ” . In Molecular and environmental aspects of mutagenesis , Edited by: Prakash , L. 17 – 31 . Springfield, Ill. : Charles C Thomas .
  • Lawley , P. D. and Shah , S. A. 1972 . Methylation of ribonucleic acid by the carcinogens dimethyl sulfate, N‐methyl‐N‐nitrosourea and N‐methyl‐N'‐nitroguanidine . Biochem. J. , 128 : 117 – 132 .
  • Lawley , P. D. and Thatcher , C. J. 1970 . Methylation of deoxyribonucleic acid in cultured mammalian cells by N‐methyl‐N'‐nitro‐N‐nitrosoguanidine . Biochem. J. , 116 : 693 – 707 .
  • Lea , M. A. , Miller , S. , Macauf , I. , Hirschberg , E. and Morris , H. P. 1972 . Action of Miracil D and related compounds on DNA and RNA synthesis in regenerating liver and hepatomas . Int. J. Cancer , 9 : 484 – 489 .
  • Lee , S. Y. 1973 . Current status of the host‐mediated L5178Y system for detecting chemical mutagens . Environ. Health Perspect. , : 145 – 149 .
  • Legator , M. S. , Conner , T. H. and Stoeckel , M. 1975 . Detection of mutagenic activity of metronidazole and niridazole in body fluids of humans and mice . Science , 188 : 1118 – 1119 .
  • Loveless , A. 1969 . Possible relevance of 0–6 alkylation of deoxyguanosine to the mutagenicity and carcinogenicity of nitrosamines and nitrosamides . Nature , 223 : 206 – 207 .
  • Lucier , G. W. , McDaniel , O. S. , Bend , J. R. and Faeder , E. 1973 . Effects of hycanthone and two of its chlorinated analogs on hepatic microsomes . J. Pharmacol. Exp. Ther. , 186 : 416 – 424 .
  • Lüers , H. 1955 . Biologisch‐genetische Untersuchungen über die Wirkung eines Thioxanthon‐derivates an Drosophila melanogaster . Zeitsch. Vererbungsl. , 87 : 93 – 96 .
  • Mattocks , A. R. 1968 . Toxicity of pyrrolizidine alkaloids . Nature , 217 : 723 – 728 .
  • Mattocks , A. R. 1971 . Synthetic compounds with toxic properties similar to those of pyrrolizidine alkaloids and their pyrrolic metabolites . Nature , 232 : 476 – 477 .
  • Maugh , T. H. II . 1974 . Chemical carcinogenesis: A long‐neglected field blossoms. Can potential carcinogens be detected more quickly? . Science , 183 : 940 – 944 .
  • McCalla , D. R. and Voutsinos , D. 1974 . On the mutagenicity of nitrofurans . Mutation Res. , 26 : 3 – 16 .
  • McCann , J. , Spingarn , N. E. , Kobori , J. and Ames , B. N. 1975 . Detection of carcinogens as mutagens: Bacterial tester strains with R factor plasm ids . Proc Nat. Acad. Sci. U.S. , 72 : 979 – 983 .
  • McLean , E. K. 1970 . The toxic actions of pyrrolizidine (senecio) alkaloids . Pharmacol. Revs. , 22 : 429 – 483 .
  • Meadows , M. G. 1973 . Mutagenic action of two indazole analogs on Saccharomyces cerevisiae , Department of Genetics, University of Alberta . M.S. thesis
  • Meadows , M. G. , Quah , S.‐K. and von Borstel , R. C. 1973 . Mutagenic action of hycanthone and of IA‐4 on yeast . J. Pharmacol. Exp. Ther. , 187 : 444 – 450 .
  • Miller , E. C. and Miller , J. A. 1971 . “ The mutagenicity of chemical carcinogens: Correlations, problems, and interpretations ” . In Chemical mutagens: Principles and methods for their detection , Edited by: Hollaender , A. vol. 1 , 83 – 119 . New York : Plenum Press .
  • Mizobuchi , K. , Demerec , M. and Gillespie , D. H. 1962 . Cysteine mutants of Salmonella typhimurium . Genetics , 47 : 1617 – 1627 .
  • Moore , J. A. 1972 . Teratogenicity of hycanthone in mice . Nature (London) , 239 : 107 – 109 .
  • Muller , H. J. 1950 . Our load of mutations . Amer. J. Human Genetics , 2 : 111 – 176 .
  • Mustacchi , P. 1973 . “ The etiology of cancer: Parasites ” . In Cancer medicine , Edited by: Holland , J. F. and Frei , E. III . 106 – 112 . Philadelphia : Lea and Febiger .
  • Newton , A. , Masys , D. , Leonardi , E. and Wygal , D. 1972 . Association of induced frameshift mutagenesis and DN A replication in Escherichia coli . Nature New Biology , 236 : 19 – 22 .
  • Oakberg , E. F. 1974 . “ Response of spermatogonia of the mouse to hycanthone: A comparison with the effect of gamma rays ” . In Physiology and genetics of reproduction, Part A , Edited by: Coutinho , E. M. and Fuchs , F. 197 – 207 . New York : Plenum Press .
  • Obe , G. 1969 . Zur Wirkung von Miracil auf menschliche Leukozytenchromosomen in vitro . Molec. Gen. Genetics , 103 : 326 – 328 .
  • Obe , G. 1970 . Die Verteilung Miracil D‐induzierter achromatischer Läsionen und Chromatidbrüche auf den Chromosomen menschlicher Leukozyten . Z. Naturforsch. , 25b : 115 – 116 .
  • Obe , G. 1973 . Action of hycanthone on human chromosomes in leukocyte cultures . Mutation Res. , 21 : 287 – 288 .
  • Oeschger , N. S. and Hartman , P. E. 1970 . ICR‐induced frameshift mutations in the histidine operon of Salmonella . J. Bacteriol. , 101 : 490 – 504 .
  • Ong , T. Mutagenicity of nitrofuran derivatives in Neurospora crassa . Paper presented at 5th Annual Meeting, Environ. Mutagen. Soc. March 8–11 .
  • Prates , M. D. and Gillman , J. 1959 . Carcinoma of the urinary bladder in the Portuguese East African with special reference to bilharzial cystitis and preneoplastic reactions . So. Afr. J. Med. Sci. , 24 : 13 – 40 .
  • Radman , M. 1974 . “ Phenomenology of an inducible mutagenic DNA repair pathway in Escherichia coli: SOS repair hypothesis ” . In Molecular and environmental aspects of mutagenesis , Edited by: Prakash , L. 128 – 140 . Springfield, Ill. : Charles C Thomas .
  • Radman , M. , Cordone , L. , Krsmanovic‐Simic , D. and Errera , M. 1970 . Complementary action of recombination and excision in the repair of ultraviolet irradiation damage to DNA . J. Mol. Biol. , 49 : 203 – 212 .
  • Regan , J. D. and Setlow , R. B. 1973 . “ Repair of chemical damage to human DNA ” . In Chemical mutagens: Principles and methods for their detection , Edited by: Hollaender , A. vol. 3 , 151 – 170 . New York : Plenum Press .
  • Riddle , D. L. and Roth , J. R. 1970 . Suppressors of frameshift mutations in Salmonella typhimurium . J. Mol. Biol. , 54 : 131 – 144 .
  • Rogers , S. H. and Bueding , E. 1971 . Hycanthone resistance: Development in Schistosoma mansoni . Science , 172 : 1057 – 1058 .
  • Rohrback , M. S. , Humphries , B. A. , Yost , F. J. , Rhodes , W. G. , Boatman , S. , Hiskey , R. G. and Harrison , J. H. 1973 . The reaction of 4,4'‐bis‐dimethylaminodiphenylcarbinol with the sulfhydryl group: A new reagent for sulfhydryl analysis . Anal. Biochem. , 52 : 127 – 142 .
  • Rosi , D. , Peruzzotti , G. , Dennis , E. W. , Berberian , D. A. , Freele , H. and Archer , S. 1965 . A new active metabolite of “Miracil D” . Nature (London) , 208 : 1005 – 1006 .
  • Rosi , D. , Merola , A. J. and Archer , S. 1967a . A possible metabolic basis for the schistosomicidal activity of Mirasan and N‐(3‐chloro‐4‐methylphenyl)‐piperazine . Life Sci. , 6 : 1433 – 1437 .
  • Rosi , D. , Peruzzotti , G. , Dennis , E. W. , Berberian , D. A. , Freele , H. , Tullar , B. F. and Archer , S. 1967b . Hycanthone, a new active metabolite of lucanthone . J. Med. Chem. , 10 : 867 – 876 .
  • Russell , W. L. and Kelly , E. M. 1973 . Ineffectiveness of hycanthone in inducing specific‐locus mutations in mice . Mutation Res. , 21 : 14 (Abstract)
  • Rustia , M. and Shubik , P. 1972 . Induction of lung tumors and malignant lymphomas in mice with metroniridazole . J. Nat Cancer Inst. , 48 : 721 – 729 .
  • Sauro , F. M. and Green , S. 1973 . In vivo evaluation of chloroindazole thioxanthene IA‐4 (a hycanthone analog) and Niridazole in rat bone marrow . J. Pharmacol. Exp. Ther. , 186 : 399 – 401 .
  • Shahin , M. M. and deSerres , F. J. 1973 . The effect of pH on hycanthone methanesulphonate induced inactivation and mitotic recombination in D5a new diploid strain of Saccharomyces cerevisiae . Mutation Res. , 21 : 234
  • Shahin , M. M. and deSerres , F. J. 1974 . The effect of pH on hycanthone methanesulfonate induced inactivation and mitotic recombination in Saccharomyces . Mutation Res. , 26 : 377 – 384 .
  • Shahin , M. M. and Kilbey , B. J. 1974 . Genetic activity of the anti‐schistosomal agent SQ 18506 in yeast . Mutation Res. , 26 : 193 – 198 .
  • Shungu , D. L. and Cook , T. M. 1974 . Induction of P22 prophage in Salmonella typhimurium by hycanthone . J. Virol. , 13 : 1153 – 1154 .
  • Sieber , S. M. , Whang‐Peng , J. and Adamson , R. H. 1972 . Evaluation of hycanthone for potential cytotoxic, chromosomal, embryotoxic and antitumor effects . Fed. Proc. , 31 : 554 (Abstract)
  • Sieber , S. M. , Whang‐Peng , J. , Johns , D. G. and Adamson , R. H. 1973 . Effects of hycanthone on rapidly proliferating cells . Biochem. Pharmacol. , 22 : 1253 – 1262 .
  • Smith , R. H. 1973 . Lack of mutagenicity of hycanthone in Habrobracon serinopae females . Mutation Res. , 21 : 279 – 281 .
  • Smith , R. H. and von Borstel , R. C. 1971 . “ Inducing mutations with chemicals in Habrobracon ” . In Chemical mutagens: Principles and methods for their detection , Edited by: Hollaender , A. vol. 2 , 445 – 460 . New York : Plenum Press .
  • St. Pierre , M. L. 1968 . Mutations creating a new initiation point for expression of the histidine operon in Salmonella typhimurium . J. Mol. Biol. , 35 : 71 – 82 .
  • Straus , D. S. 1974 . Induction by mutagens of tandem gene duplications in the glyS region of the Escherichia coli chromosome . Genetics , 78 : 823 – 830 .
  • Straus , D. S. , Hartman , P. E. and Hartman , Z. 1974 . “ Actions of mutagens in Salmonella: Molecular mutagenesis ” . In Molecular and environmental aspects of mutagenesis , Edited by: Prakash , L. 73 – 88 . Springfield, Ill. : Charles C Thomas .
  • Tabor , H. and Tabor , C. W. 1972 . Biosynthesis and metabolism of 1,4‐diaminobutane, spermidine, spermine, and related amines . Adv. Enzymol. , 36 : 203 – 268 .
  • U , R. 1972 . Enhancing effect of lucanthone (Miracil D) on the frequency of X‐ray‐induced chromosome loss in Drosophilagerm cells . Mutation Res. , 14 : 315 – 324 .
  • Voogd , C. E. , van der Stel , J. J. and Jacobs , J. J. J. A. A. 1974 . The mutagenic action of nitroimidazoles. I. Metronidazole, nimorazole, dimetridazole and ronidazole . Mutation Res. , 26 : 483 – 490 .
  • Waring , M. J. 1973 . Interaction of indazole analogs of Miracil D and hycanthone with closed circular duplex deoxyribonucleic acid . J. Pharmacol. Exp. Ther. , 186 : 385 – 389 .
  • Weinstein , I. B. and Hirschberg , E. 1971 . Mode of action of Miracil D . Progr. Molecular Subcellular Biol. , 2 : 232 – 246 .
  • Weinstein , I. B. , Carchman , R. , Marner , E. and Hirschberg , E. 1967 . Miracil D: Effects on nucleic acid synthesis, protein synthesis, and enzyme induction in . Escherichia coli. Biochim. Biophys. Acta , 142 : 440 – 449 .
  • Weisburger , J. H. , Yamamoto , R. S. , Williams , G. M. , Grantham , P. H. , Matsushima , T. and Weisburger , E. K. 1972 . On the sulfate ester of N‐hydroxy‐N‐2‐fluorenylacetamide as a key ultimate hepatocarcinogen in the rat . Cancer Res. , 32 : 491 – 500 .
  • Witkin , E. M. 1974 . Thermal enhancement of ultraviolet mutability in a tif‐1 uvrA derivative of Escherichia coli B/r: Evidence that ultraviolet mutagenesis depends upon an inducible function . Proc. Nat. Acad. Sci. U.S. , 71 : 1930 – 1934 .
  • Yamamoto , N. , Fukuda , S. and Takebe , H. 1970 . Effect of a potent carcinogen, 4‐nitroquiniline 1‐oxide, and its reduced form, 4‐hydroxylaminoquinoline 1‐oxide, on bacterial and bacteriophage genomes . Cancer Res. , 30 : 2532 – 2537 .
  • Zilversmit , R. 1970 . Thioxanthenones: Structural differences between lucanthone and its N‐methyl derivative . Mol. Pharmacol. , 6 : 172 – 177 .
  • Zilversmit , R. 1971 . Thioxanthones: Studies on the hydrogen‐bonding capacity of lucanthone . Mol. Pharmacol. , 7 : 674 – 678 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.