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Radioiodination Via Isotope Exchange in Pivalic Acid

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Radioiodination Via Isotope Exchange in Pivalic Acid AppL Radiat. 1sot. Vol. 37, No. 8, pp. 907-913, 1986 0883-2889•86 $3.00 + 0.00 Int. J. Radiat. AppL lnstrum, Part A Pergamon Journals Ltd Printed in Great Britain Radioiodination via Isotope Exchange in Pivalic Acid JAMEY P. WEICHERT, MARCIAN E, VAN DORT, MICHAEL P. GROZIAK, and RAYMOND E. COUNSELL* Departments of Medicinal Chemistry and Pharmacology, The University of Michigan, Ann Arbor, MI 48109, U.S.A. A variety of benzoic and aryl aliphatic mono and polyiodinated acids and esters (sterol, triglyceride) were radioiodinated in 55-99% radiochemical yield by isotope exchange with Naf25I in a melt of pivalic acid. In general, the reaction was complete in 1 h at 155°C with little or no substrate decompostion. High specific activity studies afforded 125I-labelediopanoic acid with a specific activity of over 700 Ci/mmol. Introduction Although isotope exchange of aliphatic iodides introduction of radioiodine into organic molecules is usually conducted in a refluxing solvent such as ~:an be accomplished by a variety of techniques acetone, methyl ethyl ketone (MEK), water, or depending on the structure of the compound to be ethanol, °) unactivated aryl iodides generally require labeled. Excellent reviews of radioiodination methods higher reaction temperatures to effect the exchange. I~ave recentlybeen reported/~'2~ Aromatic compounds Accordingly, high boiling solvents such as propylene possessing electron donating groups (e.g. phenols glycol have been utilized with some success. °~) In ~nd anilines) are easily radiolabeled by electrophilic another method, the. substrate and radioiodide are iodination in the presence of radioiodine, iodine reacted at elevated temperatures (100--200°C) in a raonochloride, chloramine-T, iodogen, etc/~) A "melt" fashion. The molten reaction medium must x ariety of methods also exist for radioiodination possess a sufficiently high dielectric constant to solu- cf unactivated aromatic rings and, in general, the bilize both the substrate and radioiodide. Examples ~lethod of choice is dependent on the degree of of such media include benzoic acid02) (m.p. 122°C, sraecific activity sought. If high specific activity (Ci/ b.p. 249°C) and acetamide (m.p. 82°C, b.p. 221°C). nlmol) is desired, one approach involves exchange The latter has been used with some success by several of an appropriate leaving group with radioiodide groups, <t3"~4) but only with limited success in our aad subsequent separation of the substrate from the laboratory3 ts) Another method, which employs ntdioiodinated product. Leaving groups recently ammonium sulfate, is conducted below the melting employed in this manner include aryl boronic point of both the exchange medium and the sub- a~:ids,t3~ aryl thallium trifluoroacetates,~4) triazenes, t5'6) strate. Employing ammonium sulfate in this manner and metallated arenes (tin, germanium, silicon)/7~ also has a catalytic effect on the exchange, ttr'~7) which, Although very high specific activities (2000 Ci/mmol) according to the authors, is attributed to a gradual c~n be achieved, radiochemical yields are typically increase in the acidity of the medium as a result of le,~s than 30%. Direct electrophilic radioiodination in situ decomposition of ammonium sulfate with of the phenyl ring also affords high specific activity concomitant loss of ammonia, tts) Copper sulfate has p~oducts, but in this case, isomeric mixtures also been used in a similar manner3 ~s'~% frequently result which are usually difficult to We have examined the acetamide melt procedure se~arate3S-~0~ quite extensively in studies with radioiodinated sterol If high specific activity is not required, iodine ex- esters. <~5'2°~ The method generally afforded sufficient, change of aryl iodides with radioiodide represents a albeit low, yields of labeled product. Utilization of viable alternative. Advantages of the method include ammonium sulfate also afforded low yields of radio- ease of synthesis, characterization, and handling of iodinated products. This was due in part, to the th,.' stable substrate, and that no complex separation formation of large amounts of volatile iodine upon techniques are necessary since the substrate and addition of ammonium sulfate to the substrate/ radioiodinated product are chemically identical. radioiodide mixture. Based on these results and the finding that acidic conditions facilitate the exchange (vide infra), we * Author to whom correspondence should be addressed. Current address: Department of Pharmacology, 6322 Medi- sought a new exchange medium. In fulfilling the cal Sciences Building I, University of Michigan Medical desired requirements, it was necessary that the School, Ann Arbor, MI 48109-0010, U.S.A. medium possess sufficient acidity, appropriate melt- 907 908 JAMEY P. WEICI.-[ERTet al. ing and boiling points, and relative chemical inert- Radioiodine exchange in pivalic acid. General ness. Although acetic acid seemed to qualify, and has procedure indeed been utilized as an exchange medium, its The compound to be radioiodinated (1-5 mg) was chemical inertness in the presence of esters was placed in a 2-mL serum vial which was then sealed dubious. A homolog of acetic acid, pivalic acid with a Teflon-lined rubber septum and aluminum (trimethylacetic acid), more closely fits the desired cap. Freshly distilled THF (100-200 mL) and aque- physical properties (m,p. 33°C, b.p. 164°C). More- ous Na125I (10-50/~L were added in succession via a over, the steric hindrance associated with this acid microliter syringe and the vial was gently swirled to also decreased the likelihood of it becoming a reac- dissolve the contents and ensure homogeneity. Inlet tant or promoter of side reactions under conditions and outlet cannuli were inserted and a gentle stream of the exchange reaction. Initial studies with pivalic of nitrogen applied to evaporate the solvents. When acid as the exchange medium were promising and in the residue appeared dry, the seal was removed and fact afforded [~5I]cholesteryl iopanoate (Sb) in over solid pivalic acid (5-20 mg, dried by azeotrope with 90% radiochemical yield with little or no ester hydro- toluene and distilled under nitrogen) was added. The lysis. Subsequent studies with og-(3-amino-2,4,6-tri- vial was resealed as previously described and partially iodophenyl)-alkanoate triacylglycerols and free acids immersed in a preheated (155-160°C) oil bath. When were also successful. Based on these favorable results, ~he isotope-exchange reaction was essentially com- we continued to study the scope of pivalic acid as plete (usually 1-2 h), the reaction vial was allowed an exchange medium with a variety of different to cool, dry THF (200/zL) was added with a glass substrates as shown in Tables 1-5. syringe and the vial swirled gently. A TLC sample (1-2 #L) was removed with a 10/~L syringe and the remaining contents were transferred to the top of a silica gel-60 column (1 x 10cm) and subsequently Materials and Methods eluted with the appropriate solvent system. If neces- sary, especially when labeling polar compounds, ex- The 125I used was a no-carrier-added solution of cess pivalic acid can be removed prior to chromatog- Na~25I (5 mCi/0.1 mL) in reductant-free 0.1 N NaOH raphy by inserting a disposable syringe containing obtained from New England Nuclear. Radioactivity granulated charcoal as a trap into the reaction vial was quantified with a Searle 1185 y-counter. Tetra- while heating and allowing the pivalic acid to distill hydrofuran (THF) was distilled from LiA1H4 under into the trap. When eluting the column, a survey argon immediately prior to use. All radioiodination meter probe was placed at the outlet of the column reactions were conducted inside a plexiglass glove to serve as a radiodetector. Fractions were collected box vented with a model RIT-140 radioiodine trap and the radiochemical purity of each was monitored (Hi Q Filter Products, La Jolla, California). Thin by TLC using u.v. and radioactivity detection. The layer chromatography (TLC) analyses were per- appropriate fractions were combined and the solvents formed on Merck silica gel-60F254 polyethylene- removed with a gentle stream of nitrogen. HPLC backed plates. The plates were analyzed by u.v. analysis of the final compound confirmed both chem- and scanned for radioactivity on a Vangard 930 ical (u.v.) and radiochemical (radioactivity) purity, autoscanner immediately after development and and because u.v. and radioactivity were plotted drying. Radiochemical yield was then determined by simultaneously with a two-pen strip chart recorder, integration of the chromatogram peaks (by cut and calculation of specific activity was also possible by weigh) and calculated as the ratio of radioactivity of comparison of u.v. and radioactivity peak areas to exchanged product to the total radioactivity on the preconstructed standard calibration curves. Reaction plate. In general, two solvent systems were used times and radiochemical yields are included in (hexane/ethyl acetate, 5:2 for esters and THF/ Tables 1-5. Actual isolated yields were generally hexane, 6:4 for acids). In both systems, the Rr of 5-20% lower than shown depending on the extent of Na~ZSI was from 0 to 0.05. Column chromatography purification necessary or desired. In all cases, radio- was performed on Merck silica gel-60 (230-400 mesh) chemical purity of final compounds exceeded 95%. eluted in the same two solvent systems. The HPLC system used to confirm radiochemical purity and determine specific activity of some of the compounds, consisted of an Altex l l0A
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