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Comparison of Some Carcinogenic, Mutagenic, and Biochemical Properties of S-Vinylhomocysteine and Ethionine1

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Comparison of Some Carcinogenic, Mutagenic, and Biochemical Properties of S-Vinylhomocysteine and Ethionine1 [CANCER RESEARCH 42, 4364-4374, November 1982] 0008-5472/82/0042-OOOOS02.00 Comparison of Some Carcinogenic, Mutagenic, and Biochemical Properties of S-Vinylhomocysteine and Ethionine1 Wilbur R. Leopold,2 James A. Miller,3 and Elizabeth C. Miller McArdle Laboratory for Cancer Research, University of Wisconsin Center for Health Sciences, Madison, Wisconsin 53706 ABSTRACT than the very low levels reported for L-[ef/7y/-3H or ef/7y/-14C] ethionine. Some carcinogenic, mutagenic, and biochemical properties of DL-ethionine and S-vinyl-DL-homocysteine (vinthionine) were INTRODUCTION compared to examine a possible role of vinthionine as a prox imate carcinogenic metabolite of ethionine. Both DL-amino Ethionine, the S-ethyl analog of methionine, is carcinogenic acids induced hepatic carcinomas in essentially all of the male for rat liver (15, 16) and mutagenic for some fungi (25, 32, 63), Fischer rats fed these structurally similar compounds for 16 to but not for Salmonella typhimurium mutants (35, 39). Radio 20 months as 0.1% of a 16% casein, choline-supplemented activity from [ethyl-ì4C or efrjy/-3H]ethionine is incorporated diet; the tumors appeared sooner in the rats fed ethionine than into protein, into RNA, and, at a very low level, into DNA of rat in those fed vinthionine. Administration in a methyl-deficient liver (18, 40-42, 50, 60). A hydrolysis product of DNA from diet facilitated DL-ethionine-induced carcinogenesis more than the livers of ethionine-treated rats cochromatographed with DL-vinthionine-induced carcinogenesis. Multiple i.p. injections synthetic A/-7-ethylguanine (60), and several ethylated bases over a 12-week period of DL-vinthionine (total dose, 7 mmol/ cochromatographed with radioactive peaks from the hepatic kg body weight) induced hepatocellular carcinomas in 9 of 28 tRNA (42). By analogy with S-adenosylmethionine-mediated and 6 of 28 male Fischer rats, respectively, that were or were methyl group transfer, S-adenosylethionine, a major metabolite not subsequently treated with phénobarbital until the termina of ethionine in rats and mice (8, 16, 20, 56, 58), was proposed tion of the experiment at 25 months. Dt-Ethionine had only as a critical intermediate for the presumed ethylation of cellular marginal carcinogenic activity under these conditions. Approx macromolecules and as an ultimate carcinogenic form of ethi imately 50% of female CD-1 mice fed 0.1 % of DL-vinthionine or onine (16-19, 58). However, the time course of ethylation of DL-ethionine in the 16% casein, choline-supplemented diet tRNA in rat liver after administration of ethionine does not developed hepatomas by 18 months; male CD-1 mice were correlate with that for the accumulation of liver S-adenosyle less susceptible. thionine (42). Likewise, compounds that inhibit the accumula L- or DL-vinthionine, but not L-, D-, or DL-ethionine, was tion of S-adenosylethionine in rat liver in vivo do not block the a strong direct mutagen for Salmonella typhimurium strain labeling of liver tRNA by ethyl-radiolabeled ethionine to a TA100. L-Vinthionine (16 revertants/nmol) was about 30% similar extent (41). Further, several chemicals that inhibit ethi more mutagenic than the DL mixture was. DL-Vinthionine onine carcinogenesis in the rat have quite different effects on sulfoxide and W-acetyl-DL-vinthionine methyl ester were only liver S-adenosylethionine levels (5-7). Thus, the role of S- weakly mutagenic. Of several compounds that interfere with adenosylethionine as an ultimate carcinogenic form of ethio the metabolism of ethionine or its carcinogenic activity, only nine in the rat is not established. L-methionine (1000 nmol/plate) completely protected strain The finding that aflatoxin B2 is enzymatically dehydrogenated TA100 against the mutagenic activity of L-vinthionine (60 nmol/ to aflatoxin B, in its activation for hepatocarcinogenicity (48, plate). 62) and the evidence that vinyl carbamate is a proximate Administration of a single i.p. dose of DL-vinthionine (1 g/kg carcinogenic metabolite of ethyl carbamate (10, 11, 45, 49) body weight) to rats caused a reduction in the hepatic level of suggest S-vinylhomocysteine (vinthionine), the S-vinyl analog adenosine triphosphate, but DL-vinthionine was less effective of ethionine, as a candidate proximate carcinogenic metabolite than DL-ethionine. However, attempts to demonstrate the ac of ethionine (31 ). In contrast to ethionine, vinthionine proved to cumulation of S-adenosylvinthionine in the livers of vinthionine- be a potent mutagen for S. typhimurium TA100 (31). This treated rats or mice or as a product of L-vinthionine with an mutagenic activity and the strong qualitative correlation be adenosine triphosphate-supplemented yeast extract capable tween mutagenicity and carcmogenicity for many, but not all, of converting either DL-methionine or DL-ethionine to their S- groups of chemicals (35, 46, 59) encouraged us to compare adenosyl derivatives were unsuccessful. After a single i.p. injection, 14Cfrom L-[wny/-14C]vinthionine further the mutagenic, carcinogenic, and biochemical proper ties of ethionine and vinthionine. was bound to rat liver DNA, RNA, and protein. The magnitude of the binding to DMA (110 pmol/mg DMA 18 hr after a single i.p. injection of 31 mg/kg body weight) was of the order of that MATERIALS AND METHODS observed for strong hepatic carcinogens and much greater Instrumentation ' This work was supported by Grants CA-07175, CA-09135. and CA-22484 UV spectra were recorded with a Series EU-700 double-beam spec- from the National Cancer Institute, USPHS. trophotometer equipped with a Model EU-205-11 recorder (GCA/ 2 Present address: Warner-Lambert, 2800 Plymouth Road, Ann Arbor, Mich. 48105. McPherson Instruments, Acton, Mass.). IR spectra of compounds in 3 To whom requests for reprints should be addressed. KBr pellets were obtained with a Beckman IR-10 instrument. "*C was Received April 26, 1982; accepted July 15, 1982. determined with an lsocap/300 scintillation spectrometer (Nuclear 4364 CANCER RESEARCH VOL. 42 Downloaded from cancerres.aacrjournals.org on September 29, 2021. © 1982 American Association for Cancer Research. Carcinogenicity of S-Vinylhomocysteine and Ethionine Chicago, Inc., Chicago, III.). External standardization was used to (12:3:5) (Rf 0.65). The radiochemical purity was confirmed by analysis convert the data to dpm. Elemental analyses were performed by of 1-ml fractions collected from an automated Beckman Model 120C Huffman Laboratories, Wheat Ridge, Colo. HPLC" utilized an ALC 201 amino acid analyzer; a single radioactive peak which also contained liquid Chromatograph equipped with a Model U6K injector system, a ninhydrin-reactive material (27) was found. Ninhydrin analyses of the Model 660 solvent programmer (all products of Waters Associates, eluants from the thin-layer chromatograms and the amino acid analyzer Milford, Mass.), and a Houston Instruments Omniscribe Recorder. indicated that the chemical purity of the [MC]vinthionine was >97%. A stock solution of the [14C]vinthionine (5 mg/ml) in 30% aqueous di Chemicals methyl sulfoxide was sealed under argon and stored in the dark at -20°. Periodic analyses by thin-layer chromatography with Systems L- and DL-homocystine; D- and L-ethionine; D-, L-, and DL-methionine; A and C showed no decomposition of the labeled material for at least O-acetyl-L-serine; S-adenosyl-L-ethionine iodide; S-adenosyl-L-methi- 4 months; however, most of it decomposed to unidentified poorly water- onine iodide; DL-methionine sulfoxide; DL-methionine sulfone; choline soluble ninhydrin-positive products between 4 and 7 months. For dihydrogen citrate; S-methyl-L-methionine iodide; azetidine-2-carbox- studies of the binding of vinthionine or its metabolites to rat liver ylic acid; S-methyl-L-cysteine; S-ethyl-L-cysteine; 1-aminocyclopro- macromolecules, the aqueous dimethyl sulfoxide solution of [MC]vin- pane carboxylic acid, a-amylase (1100 units/mg); and Escherichia coli thionine was diluted at least 5-fold with nonradioactive L-vinthionine. alkaline phosphatase were purchased from Sigma Chemical Co., St. L-Vinthionine Sulfoxide. L-Vinthionine sulfoxide was prepared from Louis, Mo. DL-Ethionine, 1,10-phenanthroline, 1-aminocyclopentane L-vinthionine by the general method of Leonard and Johnson (28) for carboxylic acid, and vinyl sulfone were products of Aldrich Chemical the oxidation of sulfides to sulfoxides. L-Vinthionine (5 g) was added to Co., Milwaukee, Wis. N-Crotylglycine was from Nutritional Biochemi- 6.8 g of sodium metaperiodate in 200 ml of distilled water and stirred cals, ICN, Cleveland, Ohio; diethyl sulfone was from ICN/K and K for 3 hr at 0°. At this time, thin-layer chromatography on cellulose Laboratories, Plainview, N. Y.; ethyl vinyl sulfone was obtained from MN300 plates with 1-butanol:acetic acid:water (12:3:5) showed a Polysciences, Inc., Warrington, Pa.; ethyl vinyl sulfide was from Fair- major ninhydrin-positive spot at R, 0.54 (L-vinthionine, Rt 0.72). Silver field Chemical Co., Blythewood, S. C.; and [8-MC]GMP (495 mCi/mol) nitrate (5.35 g) was added, and the resulting precipitate of silver iodate was from ICN Pharmaceuticals, Irvine, Calif.). 3-Methylthiopropionate, was removed. The brown residue obtained on lyophilization of the 3-ethylthiopropionate, 2-methylthioacetate, 2-ethylthioacetate, and 3- supernatant was dissolved in methanol (20 ml), and L-vinthionine mercaptopropionic acid were the generous gifts of Dr. Norlin Benev- sulfoxide was precipitated with 2 volumes of acetone. The crude enga. Department of Meat and Animal Science of this university. S- product (500 mg), dissolved in 4 ml of distilled water, was dried under (frans-1,2-Dicnlorovinyl)-i_-cysteine was kindly provided by Professor reduced pressure onto 5 g of Silica Gel 60 (EM Laboratories, Inc., Max O. Schultze prior to his retirement from the Department of Bio Elmsford, N. Y.) and layered on top of a 3- x 54-cm dry column of the chemistry, College of Biological Sciences, University of Minnesota, St.
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