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In In! and RADIOPHARMACEUTICAL.S in_In! AND RADIOPHARMACEUTICAL.S Evaluation of Formamidine Sulfinic Acid and Other Reducing Agents For Use in The Preparation of Tc-99m Labeled Radiopharmaceuticals A. R. Fritzberg,* D. M. Lyster,and D. H. Dolphin Vancouver General Hospital, Vancouver, British Columbia, Canada Various reducing agents have been evaluated for their potential useful ness in the preparation of esmTc labeled radiopharmaceuticals for use in nuclear medicine. Adequate labeling of various radiopharmaceuticals was accomplished using formamidine sulfinic acid. Nitrogen-purging of solu Lions is not required, which is an advantage for in-house preparation. Tag ging requires heating, however, so heat-labile material cannot be used. Various compounds that could not be labeled when stannous chloride was used, could be tagged with “mTcwhen formamidine sulfinic acid was used as the reducing agent. JNuciMed18: 553—557,1977 Technetium-99m as pertechnetate requires reduc ganicreducingagents.For example,the useof thiols tion as part of the process of binding the Tc-99m to often results in stable complexes that prevent forma various carriers in radiopharmaceuticals. Stannous tion of the desired complex ( I 1). chloride (SnCl2) (1 ), the most commonly used re Therefore, the followingstudy was undertaken in ducing agent, is rapid and effective at room tempera an attempt to find a reducing agent that was not ture. However, it is easily oxidized to stannic ion influenced by these shortcomings. Using either nitri by oxygen and is rapidly hydrolyzed to a colloidal olotris(methylene)-triphosphonic acid or phenyl stannous hydroxide which effectively binds Tc-99m. phosphonic acid, various reducing agents were evalu In addition, residual stannous salts in the body may ated in terms of their potential for promoting binding cause localization of pertechnetate in subsequent between technetium and these ligands. brain scans (2—4). These considerations have encouraged attempts MATERIALSAND METHODS to find improved alternatives. Electrolytic reductions Preparative procedures. Reducing agent trials. So using tin electrodes (5) and zirconium electrodes lutions of the ligands, phenylphosphonic acid, or (6) have been reported, but each involves an inter nitrilotris(methylene)-triphosphonicacid,werepre mediate reducing agent. Other metal reducing agents pared at 30—SOmg/ml and adjusted to pH 7.4—7.8. used include ferric chloride coupled with ascorbic Then the reducing agent was added and the effect of acid (7), copper salts (8), and chromous salts (9). various parameters (such as concentration, time and In addition, the use of stannous pyrophosphate as an temperature) on ligand binding to Tc-99m were example of a stable stannous complex has been sug studied. gested (10). These alternatives, however, offer only Preparations with formamidine sulfinic acid limited solutions. Since the ligand requirements of (FSA).* A solution was prepared in a solvent sys technetium and other metals used as reducing agents Received May 24, 1976; revision accepted Jan. 7, 1977. are likely to be different, the use of such metallic For reprints contact: D. M. Lyster, Div. of Nuclear Mcdi reducing agents will limit the choice of ligands to cinc, Vancouver General Hospital, Vancouver, British Co those that effectively bind both the technetium and lumbia, Canada, V5Z lM9. C Presently at the University of Colorado, Denver, Cob the other metal. Complications also arise with or rado. Volume 18, Number 6 553 FRITZBERG, LYSTER, AND DOLPHIN tem suitable for injection as required by the ligand 42% bound technetium and 13% hydrolyzed or as and then an aliquot from a stock solution of FSA Tc02. Increasing the temperature to 60°Cincreased ( 10—20mg/mI, pH adjusted to 7.8—8.0)was added the TcO2 to 82%. to give a final concentration of 0.75—1.25 mg/ml. (b) Sodium bisulfite: At S mg/mi reducing agent After mixing, the preparation was heated in a water and pH 7.5, no binding was observed at room tem bath at 60°for 30—45mm, or for 10—15mm in a perature. After 30 mm at 60°Cthere was 8.2% boiling water bath. Since concentrated stock FSA TcO2 15.5% free pertechnetate, and 76.3% bound solutions were slightly turbid, those used in prepa technetium. rations for injections into animals were Millipore (c) Sodium thiosulfate: At 5 mg/ml reducing filtered (0.22@z). agent and pH 7.5, less than 1% binding was ob Rate studies using HEDP as the ligand were served after 15 mm at room temperature. done in a constant-temperature shaker bath at 49°C 3. Hydrazines. ( ±0.75°Cvariation observed) . Samples were equili (a) Hydrazine: At 2 mg/mI reducing agent and brated for 4 mm before Tc-99m as pertechnetate was pH 7.5, there was 1.4% bound after 30 mm at room added. Aliquots were removed at stated intervals temperature and a mixture of 32.0% bound, 5.2% and the percentage bound was immediately deter TcO2, and 62.8% free after 30 mm at 95°C. mined by thin-layer chromatography. (b) Benzoylhydrazine: No binding was observed Analysis. The complexes were chromatographed up to95°for30 mm at30 mg/ml. on silica gel impregnated glass fiber strips (Gelman (c) Hydralazine (1-hydrazinophthalazine) : At 30 ITLC) in the solvents saline, 1-butanol, and others mg/mi and pH 7.5, there was 1 % bound Tc after as required. After developing in the appropriate 30 mm at room temperature and I 2.7% bouna after solvent, the strips were cut into 1-cm sections and 30 mm at 95°C.Tc02 formation was negligible. counted in a well scintillation counter. 4. Miscellaneous. A variety of miscellaneous re Clinically used radiopharmaceuticals such as ducing agents were also evaluated with the results DTPA, HEDP and pyrophosphate were prepared summarized in Table 1. Only dithiothreitol gave sig with FSA and injected ( I mCi) intravenously into nificant binding, and it was also accompanied by the 2.5- to 4.0-kg white New Zealand rabbits for com formation of TcO2. parison with stannous preparations. Scans were per 5. Sulfinic acids. Formamadine sulfinic acid (A), formed on a scintillation camera at appropriate p-N-acetylphenylsulfinicacid (B), andsodiumform intervals. aldehyde sulfoxylate (C) were studied. No Tc bind Toxicity. The toxicity of FSA was determined by ing resulted from the p-N-acetylphenylsulfinic acid injection of a 30 mg/mi solution (pH 7.5) into the after 30 mm at 95°C. However, binding was ob tail veins of mice. A minimum of six mice were used served with sodium formaldehyde sulfoxylate, but for each level studied. The volume of injection was only after heatingto 95°C,in which casea mixture varied from 0. 1 to 0.5 ml and the animals were of 31% bound and 53 % TcO2 resulted. FSA gave observed for one week following the injection. satisfactory results using the trial ligands, with little unbound pertechnetate or Tc02. RESULTS + Since many different reducing agents were inves H2N 0 ,@‘ II tigated, it was convenient to group them by classes ,F—so@cH3—c— H0—CH2—S0@No in order to summarize the results. The agent of HN choice, FSA, and other sulfinates are covered last A B C in a more detailed study. 1. Stannous salts. Several stannous salts were In view of the encouraging preliminary results studied to find one that would be effective at reduc with FSA, and its suitability for use with current tion, but stable to hydrolysis. Despite encouraging DamTc radiopharmaceuticals, its potential for general reports, stannous acetate ( 12 ) and stannous formate applicability was studied. ( 13 ) hydrolyzed easily at neutral pH to form a Various radiopharmaceuticals, currently prepared stannous colloid. In addition, the same behavior was with stannous chloride, were prepared with FSA and observed for the oxalate and tartrate. These stan their propertiescompared. nous salts provided no advantage over stannous Ethane-1-hydroxy-1 , 1-diphosphonic acid, diso chloride. dium salt (HEDSPA) (14) . The complex was pre 2. Sulfur oxygen radicals. pared by heating a mixture of HEDSPA at 31.3 (a) Sodium dithionite: At room temperature, pH mg/ml and 1.2 mg/mi FSA at pH 7.4 for 1 hr. The 7.5, and 5 mg/ml of reducing agent, the results were results were 1.2% free pertechnetate, 0.2% TcO2, 554 JOURNAL OF NUCLEAR MEDICINE RADIOCHEMISTRYAND RADIOPHARMACEUTICALS TABLE 1. RESULTSOF REACTIONS BETWEEN TABLE 3. CONCENTRATION-DEPENDENCEOF D9mTcO—AND VARIOUS REDUCING AGENTS THE STABILITYOF Tc-99m DTPA PREPARED IN THE PRESENCEOF PHENYLPHOSPHONATE WITH FSA* OR NITRIOLOTRIS(METHYLENE)-TRIPHOSPHATE mg/mITime DTPA = 6.0 ,6%%Reducing Tc0(hr)t% Tc04 % TcO,% bound agent 1°C boundTcO,TcO, 0.3 Sodiumborohydride25503515Cyonoborohydride9500100Sodum 3.25 0.5 0.2 99.3 10.0 2.1 0.0 97.9 nitrite250.3099JSodium 22.00.3 25.874.1DTPA [email protected] amalgam257.02.091.0Dithiothreitol5884.013.52.5Propionaldehyde2541 = 9.0 mg/mI .01 .557.5 0 0.9 0.2 98.9 3.25 0.3 0.2 99.5 10.0 0.3 0.1 99.6 22.0 7.2 0.2 92.6 and 98.6% bound Tc, and were identical after 30 @ mm and 24 hr. S Complexes were prepared with 1 .0 mg/mI FSA at pH 7.5 and heated at 58° for 20 mm. Scans of a rabbit injected with the preparation in t Delay in analysisafter preparation of the complex. dicate good bone uptake. The rate of reduction and binding was slow enough at 49—50°Cto permit convenient monitoring of the progress of the reaction. The results are shown Rabbit scans and renograms compared favorably in Table 2 for HEDP as ligand and 1.0 mg/ml with thoseusingtheCaDTPA/SnC12kit asprepared FSA. Nearly complete binding is observed after 30 for clinical use. mm. When the reaction is carried out at 95°C,bind Several other complexes of Tc-99m have been pre ing is 99% in less than 5 mm.
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