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Studies on the Metabolism of Thioacetamide-S35 in the Intact Rat*

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Studies on the Metabolism of Thioacetamide-S35 in the Intact Rat* Studies on the Metabolism of Thioacetamide-S35 in the Intact Rat* ODDVARNYGAARD,LORENTZELDJARN,ANDKARLFORDNAKKEN (Norsk Hydro's Institute for Cancer Research, Norwegian Radium Hospital, Oslo, Norway) Through the work of Fitzhugh and Nielson (5) ing of TAA with radioactive sulfur on a micro and Ambrose et al. (1), it has been established that scale were studied, and the procedure finally thioacetamide (TAA) in moderate doses (25 worked out was as follows : mg/kg/day) induces liver cirrhosis in rats, when One hundred mg. of barium sulfate-S35 was re administered over a period of several months. Ac duced with carbon monoxide to barium sulfide, as cording to Rather (7), the earliest morphological described elsewhere (3). The barium sulfide was effect is an increase in the size of the nucleoli and transferred to the centrally suspended cup A of the nuclei of the parenchymal cells. These changes the diffusion apparatus shown in Chart 1. In the are well developed within a few days and are outer compartment was placed 200 mg. of un- largely reversible. labeled TAA dissolved in 9.5 ml. of "super dry" From measurements of nuclear volume and ethyl alcohol1 and 0.5 ml. of 0.05 N sodium alco analyses of desoxyribonucleic acid (DNA), Carnes hólate in absolute alcohol. The apparatus was and co-workers (2) have found a proportionality flushed with dry oxygen-free nitrogen and stop between nuclear volume and DNA content in the pered, leaving a gas phase of approximately 20 ml. hepatic cells of TAA-treated rats. However, Through the greased rubber stopper was intro Laird (6) and Thomson et al. (8) have failed to find duced a hypodermic needle, and the barium sul an increase in the average content of DNA per fide was acidified with 1.5 ml. of 75 per cent nucleus after administration of TAA, although phosphoric acid by means of a syringe. The needle they observed the morphological changes de was carefully withdrawn to avoid loss of hydrogen scribed by Rather. On the other hand, Laird found sulfide. The vessel was kept in the dark at room a considerable increase in nuclear protein and temperature and with magnetic stirring in the pentosenucleic acid (PNA) which reached a maxi outer compartment for 4-7 days. After this time mum after 7-11 days. The liver is the only organ two hypodermic needles were introduced through that appears to be affected by the administration the stopper. Hydrogen chloride in absolute ethyl of TAA (1,5,7). alcohol was added in an amount sufficient to To study the metabolism of TAA, the com neutralize the sodium alcohólate. The hydrogen pound was labeled with S35.In this paper we shall sulfide was flushed out with nitrogen and trapped present some data on the gross metabolism of in sodium hydroxide. The TAA solution was TAA and on the distribution of TAA and total evaporated to dryness under reduced pressure and sulfur radioactivity in various tissues after sub the TAA recovered and purified by recrystalliza- cutaneous injection of the labeled compound into tions from benzene. The recovery of pure TAA rats. (m.p. 107.5°-108.5°C.)was 50-60 per cent of the EXPERIMENTAL amount initially added. The compound traveled as a single spot in two different paper chromato- The synthesis of thioacetamide-S36.—The ex graph systems.2 change reaction At equilibrium the radioactive sulfur will be CH3CSNH2 + SH- ^ CH3CSNH2 + SH~ distributed between the TAA and the hydrogen 1According to Lund and Bjerrum. See A. I. Vogel, A which we found to take place in absolute ethyl Textbook of Practical Organic Chemistry, 2d ed., p. 166. alcohol was used because of its simplicity and London: Longmans, Green & Co., 1951. relatively high yield. The conditions for the label- 1The chromatograms were run on Whatman No. 1, grade 1 * This project was supported in part by a grant from paper, in one system with isopropanol:ethanol:N HC1 (3:3:1) Landsforeningen mot Kreft, Oslo, Norway. on untreated paper, and in the other with isopropano] :ethanol: water (2:2:1) on paper pretreated with 0.05 M phosphate Received for publication April 1, 1954. buffer at pH 7.5 in 0.5 MKC1. 625 Downloaded from cancerres.aacrjournals.org on September 30, 2021. © 1954 American Association for Cancer Research. 626 Cancer Research sulfide according to their absolute sulfur contents, TAA, evaporation of the solution to dryness under and the maximum obtainable specific activity can reduced pressure, and extraction of the residue be calculated accordingly. In Chart 2 is shown the with hot benzene. The isolated TAA was recrystal- percentage of maximum specific activity obtained lized from hot benzene several times after the cor in TAA after various equilibration times. After 4 rect melting point was obtained. Since wet oxida days 80 per cent of the maximum activity was tion with copper nitrate and sodium perchlorate reached. With the amounts of TAA and barium gave low recoveries of TAA sulfur as sulfate, the sulfide used the over-all yield of radioactive sulfur samples for TAA and total sulfur were oxidized as TAA was about 40 per cent. When the reaction by fusion with sodium peroxide in a steel bomb. The aliquots for the determination of total sulfur were evaporated to dryness under reduced pres sure, after the addition of a known amount of sucrose to provide bulk for the residue. A weighed amount of the total residue was transferred to the bomb and oxidized. All samples were assayed for radioactivity as previously described (4). Distribution of injected thioacetamide in various rat tissues.—A male rat, weighing 260 gm., was given a subcutaneous injection of 6.5 mg. (ap proximately 50 /ic.) of labeled TAA. The animal was killed after 85 minutes by a blow on the head, and oxalated blood was immediately collected by «50 80 60 Chart 1.—Sectionthrough diffusion apparatus. A.—Central cup, suspended by thin steel wires. 20 it.—Magnet stirring bar. O S.—Greased rubber stopper with injection needle insert ed. The stopper is kept firmly clamped during the Õ equilibration phase to prevent leakage of hydrogen 123*5 sulfide. DAYS OF EQUILIBRATION CHART2.—Production of TAA-S" from exchange of sulfur mixture was exposed to light, the solution became between unlabeled TAA and radioactive HiS under the condi turbid, and the recovery of TAA was lower. The tions described. The solid line represents the theoretical curve omission of sodium alcohólate decreased the re for a first-order reaction. action rate considerably. High sodium alcohólate concentrations also greatly lowered the recovery of heart puncture. The tissues listed in Table 1, TAA. Experiment 1, were removed, washed quickly with Gross metabolism of tkioacetamide in the rat.— cold physiological saline, blotted with a filter Four male rats, weighing 200-235 gm., were each paper, and weighed. The larger tissue samples were given a subcutaneous injection of 6 mg. of labeled forced through a tissue press, and suitable aliquots TAA in 1 ml. of physiological saline. The animals were homogenized with physiological saline in a were kept in metabolism cages, and the urine was glass "Potter-Elvehjem" homogenizer. The collected after 1, 2, 3, 4, and 8 days. Care was smaller organs were homogenized directly. For the taken to avoid contamination with feces. The emulsification of fat tissue, the addition of 0.1 gm. urine samples were analyzed for total sulfur, total of a detergent ("Teepol") proved advantageous. sulfate, free sulfate, and TAA radioactivity. The TAA was isolated from aliquots of the homoge- methods for the analysis of free and total sulfate nates after the addition of carrier TAA and are described elsewhere (4). TAA-S36 was isolated analyzed as described for the urine. For the de from the acidified urine by the addition of carrier termination of total sulfur radioactivity, other Downloaded from cancerres.aacrjournals.org on September 30, 2021. © 1954 American Association for Cancer Research. NYGAARDet al.—Metabolism of Thioacetamide-S^ 627 aliquots were dried at 40°-60°C.to minimize losses frequent or continuous administration appears due to sublimation of TAA. The residues were preferable when the effect of prolonged treatment finely ground in an agate mortar and oxidized by is to be studied. Addition of TAA to the diet, as sodium peroxide fusion. The radioactivity of the originally used by other workers (1, 2, 5, 7), thus barium sulfate recovered was determined as de seems advantageous. scribed for urine. In Table 1 are recorded the data obtained for A second male rat, weighing 260 gm., was the distribution of TAA and the total sulfur radio given a subcutaneous injection on 7 consecutive activity in various tissues. Experiment 1 shows days of a total of 40.7 mg. (approximately 350 nc.) that, 85 minutes after injection of TAA, the com of radioactive TAA. The animal was sacrificed 2 pound was highly concentrated in the bone mar days after the last injection. The tissues listed in row, the thyroid, and the adrenals. The liver, on TABLE1 DISTRIBUTIONOFS»INRATAFTERSUBCUTANEOUSINJECTIONOFTAA-S» 1TAA-S"counts/min/gmof2Tot»l S»counta/min/gmof S«'counts oforgan(gm.)0.0370.0450.500.600.711.171.732.6S7.041.74EXPERIMENTorgan(gm.)0.0270.0360.850.701.181.522.418.771.45Total/min/gmof TISSUEBone tissue69,00044,00032,0007,7005,7003,7002,7502,6602,1402,0302,0101,7601,5101,130EXPEBIUENTtissue*55,0004,3008,1004,2008,7004,5009,2003,0001,0704,500Wt.oftissue1,5703,1002,1209706101,7903001,4001,000710650 marrowThyroid glandAdrenalsSpleenEpididymisHeart muscleLungsStriated muscleKidneysBlood serumTestesBlood corpusclesLiverBrainWt. Experiment 1.—SÕmin. after the injection of a single dose of TAA-S»corresponding to 0.87 X 10* counts/min.
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