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The Effectof Stwcturalmodificationson the Adrenaluptakeof Steroidslabeled in the Sidechainwith Tellurium-123M

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The Effectof Stwcturalmodificationson the Adrenaluptakeof Steroidslabeled in the Sidechainwith Tellurium-123M TheEffectof StwcturalModificationson the AdrenalUptakeof SteroidsLabeled in the SideChainwithTellurium-123m FurnF.Knapp,Jr., KathleenP.Ambrose,andAlvinP.Callahan Oak Ridge National Laboratory, Oak Ridge, Tennessee A seriesof structurallymodifiedsteroidslabeledinthe sidechainwithTe-123m have been preparedandtested in ratsto determinethe criticalstructuralfeatures required for maximal adrenal uptake of this new class of potential adrenal-imaging agents.The Te-123m steroidsinvestigatedcontainedstructuralmodificationsof both the nucleus and side chain. Tissue distribution experiments and rectilinear scansindicatedthat 23-(isopropylteliuro)-24-nor-5a-choian-3@9-oI(saturatednu cleus), and 24-(isopropylteIIuro)-chol-5-en-3@9-ol(nuclear doublebond)showed pronouncedadrenaluptake after 1 day, with adrenal-to-liverratiosof 41 and 27, respectively.Theseresultsindicatethat a combinationof structuralfeaturesis re quiredfor significantadrenaluptakeof steroidslabeledin the sidechainwfthTe 123m.Thestructuralrequirementsincludea transringstructure,an equatorialC-S hydroxylgroup,anda 17$ sidechainof moderatelength. J Nuci Med 21:258—263, 1980 The pioneering studies of Beierwaltes and coworkers use (2,13,14). have demonstrated that steroids labeled with gamma From an analysis of structure-activity data, however, emitting nuclides can be used to image the adrenal it is difficult to predict the effect of steroid structure on glands (1,2). Iodine-l3l-labeled 19-iodocholesterol was the relative tissue distribution and potential adrenal the first agent available for the clinical detection and uptake of such compounds. Adrenal uptake often de diagnosis of human adrenal disorders by nuclear-medi pends on the general structural similarity between the cine techniques, and this agent has been used successfully radiolabeled steroid and cholesterol, and is also affected for the preoperative location of adrenal adenornas (3). by a complex combination of structural and physical A variety of radiolabeled steroids have subsequently been features that include size (steric requirements) and po investigated by various workers as potential adrenal larity (dipole moment). imaging agents. These agents include radiolabeled ste We have recently reported the preparation and pre roids substituted at C-19 with iodine (5—7) or a clinical testing of Te-1 23m-labeled 23-(isopropyl tel methyl-seleno moiety (8), phytosterols iodinated at the luro)-24-nor-5a-cholan-3/3-ol (Te- 123m 23-ITC), a C-19-methyl group (9,10), and steroids in which the steroid that shows pronounced adrenal uptake in rats C-3-hydroxyl group has been replaced with a halogen (15). Thissteroidisthefirstmemberofa newclassof (2,11,12). Biological studies with these agents have met radiopharmaceuticals labeled with the Te-123m emitter. with varying degrees of success and the radioiodinated The strategy that was developed for the synthesis of 6/3-iodomethyl- 19-nor-cholest-5( I0)-en-3/.3-ol (NP-59) Te-1 23m 23-ITC is a general approach that can be used appears the most promising agent for broader clinical to prepare various steroids (16), fatty acids (17), amino acids (18—20),and other Ic-I 23m labeled agents. The purpose of the present study is to investigate systemati Received July 12, 1979; revision accepted Dec. 14, 1979. For reprintscontact:F. F. Knapp,Jr., Nuclear MedicineTechnology cally the effect of steroid structure on the adrenal uptake Group, Health and Safety Research Div., Oak Ridge National Lab of a series of structurally modified steroids labeled in the oratory, Oak Ridge,TN 37830. side chain with Te-1 23m. 258 THE JOURNAL OF NUCLEAR MEDICINE BASICSCIENCES RADIOCHEMISTRYAND RADIOPHARMACEUTICALS EXPERIMENTAL 5-en-3f3-ol (IV, nuclear double bond) was prepared by coupling sodium isopropyl tellurol with 3f3-acetoxy General. The Te- 123m was produced by neutron ir 24-bromo-chol-5-ene. Reaction of sodium isopropyl radiation of 94.7 1% enriched Te- 122 as described earlier (15). Radioactivesampleswerecountedusinganauto tellurol with 3/3-methoxy-24-bromo-chol-5-ene gave 3/.3-methoxy-24-(isopropyl telluro)-chol-5-ene (V, hy matic gamma counter. Chromatographic analyses by drophobic C-3 substituent). The telluro steroid with the thin-layer and by silicic acid column were performed as short side chain, I 7f3-[(isopropyl telluro)methyl]-an described earlier (15). The brominated steroid substrates were prepared (16,21 ) from commercially available bile drost-5-en-3f3-ol (VI), was prepared by reaction of so acids.* All other solvents, chemicals and reagents were dium isopropyl tellurol with 3/3-acetoxy-l 7/3-(bro analytical grade unless otherwise stated. momethyl)-androst- 5-ene. The bromi nated steroid Steroidsyntheses,generalfeatures.A total of six, substrates used in these reactions were prepared by well structurally modified steroids substituted in the side established procedures. The 3/3-acetoxy-23-bromo chain with alkyl-telluro moieties (Fig. I ) were synthe 24-nor-5a-cholane and 3a-acetoxy-23-bromo-24-nor sized by the general procedure outlined below. 5/3-cholane were prepared by modified Hunsdiecker degradation of allisolithocholic acid and lithocholic acid NH3 NH3 acetates, respectively, as described earlier (21 ). The Te + Na )@Na2Te2 + RX > R2Te2 Step I Step 2 3/3-acetoxy-24-bromo-chol- 5-ene was prepared by the NaBH4 MeOH following route: methyl-3/3-hydroxy-chol-5-en-24- @ NaTe-R + steroid —Br steroid-Te-R oate —*methyl-3f3-methoxy-chol-5-en-24-oate Step 3 Step 4 313-methoxy-24-hydroxy-chol-5-ene —@3f.@-methoxy The various structural modifications that were chosen 24-bromo-chol-5-ene —@3/3-acetoxy-24-bromo-chol-5- involved both the side chain and nuclear regions of the ene. In a similar manner, 3/3-acetoxy- 17fl-(bromom steroid framework and we did not attempt to optimize ethyl)-androst-5-ene was prepared as follows: methyl the chemical yields of either the brominated steroid androst-5-en-l 7/3-carboxylate -÷methyl-3/3-methoxy substrates or the alkyl-telluro substituted steroids. The 17/3-carboxy-androst-5-en-20-oate —÷3f3-methoxy synthetic procedure was adapted for the preparation of I 7f3-(hydroxymethyl)-androst-5-ene —k3f3-methoxy each compound using the appropriate alkyl halide in 1713-(bromomethyl)-androst-5-ene —÷3f3-acetoxy Step 2 and the requisite brominated steroid in Step 4. I7f3-(bromomethyl)-androst-5-ene. The synthetic ste The 23-(isopropyl telluro)-24-nor-5a-cholane-3f3-ol (I, roids were homogeneous by both silicic acid column and saturated nucleus, trans A/B ring juncture) and 23- thin layer chromatography, and their behavior under (isopropyl telluro)-24-nor-5/3-cholan-3a-ol (II, saturated infrared spectroscopy, low- and high-resolution mass nucleus, cis A/B ringjuncture) were prepared by reac spectrometry, and proton nuclear magnetic resonance tion of sodium isopropyl tellurol with 3/3-acetoxy-23- was consistent with the proposed structures. Details of bromo-24-nor-5a-cholane and 3a-acetoxy-23-bromo the synthesis and physical properties of the brominated 24-nor-5f3-cholane, respectively. Reaction of sodium steroid substrates and the unlabeled telluro steroids octyl tellurol with 3f3-acetoxy-23-bromo-24-nor-5a- (I)—(VI) will be described in a subsequent report. cholane gave 23-(octyl telluro)-24-nor-5a-cholan-3/3-ol The synthesis and purification of the labeled steroids (III, long side chain) and 24-(isopropyl telluro)-chol Te-123m-(II) through Te-l23m-(VI) (see Fig. 1) were Te@.( H II III Te@'L HO@ Te y @ Me0 Te IV V VI FIG. 1. Structuresof telluro-steroids. Volume 21, Number 3 259 KNAPP, AMBROSE, AND CALLAHAN performed in the same manner as that described earlier 5@-cholan-3a-ol. lsopropyl Te- I23m tellurol (10.2 mCi) (15) for Te-l 23m-23-ITC, now referred to as Te was prepared as described earlier (16) and was reacted I 23m-(l), namely, 23-(isopropyl [123mTe]telluro)-24- with 3ct-acetoxy-23-bromo-24-nor-5f3-cholane (98 mg, nor-5a-cholan-3/3-ol. The labeled steroids were prepared 0.215 millimol) to give a crude product that, after by reacting an excess of the sodium alkyl [I23mTe] tel chromatography, gave 2.3 mCi of Te-l23m-(Il) lurols to ensure complete consumption of the brominated (chemical yield, 38%; radiochemical yield, I3%), with steroid substrates (Step 4). The Te- I 23m was combined specific activity 10 mCi/millimol. with unlabeled tellurium in order to obtain a convenient Te- I 23m-(III), 23-(octyl[ l23mTe]telluro)_24.nor. amount of material (1 millimol) with which to prepare 5a-cholan-3f3-ol. Diooctyl Te- I 23m ditelluride (25.3 the radiolabeled steroids, although products having mCi) was prepared by octyl iodide alkylation of sodium maximum specific activities of about 250 mCi/millimol Te-123 ditelluride (39.2 mCi). After reduction, the re can easily be prepared by these methods. The radiola suIting solution ofsodium octyl Te-123m tellurol was beled steroids were purified by silicic acid column reacted with 3/@-acetoxy-23-bromo-24-nor-5a-cholane chromatography of extracts from the crude reaction (45 mg, 0.084 millimol) and the crude product chro mixtures. Figure 2 illustrates a typical chromatographic matographed on silicic acid togive Te-123m-(Ill), 3.17 column profile for Te- I23m-(lV). The initial peak eluted mCi (chemical yield, 54%; radiochemical yield, 8%), from the column represents the Te- I 23m-diisopropyl with specific activity 39 mCi/millimol. ditelluride formed by facile atmospheric oxidation of the Te- I 23m-(IV), 24-(isopropyl@ l23mTeltelluro)chol.. excess radiolabeled tellurol used in the coupling step [email protected] (9.43 mCi, (Step 4), while the second peak represents Te- I 23m- 37%) was generated by reaction of isopropyl iodide with labeled (IV). sodium Te-123m detelluride (25.3 mCi). Reduction with The labeled steroids, Te-l23m-(I) through Te sodium borohydride gave a colorless solution of sodium l23m-(lV) were analyzed by thin layer radiochroma isopropyl Te- I 23m tellurol, which was reacted with tography using two solvent systems: chloroform, and 10% 3f3-acetoxy-24-bromo-chol-5-cne (45 mg, 0.096 milli ether in chloroform.
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