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United States Patent (19) 11 Patent Number: 4,707,352 Stavrianpoulos 45 Date of Patent: Nov

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United States Patent (19) 11 Patent Number: 4,707,352 Stavrianpoulos 45 Date of Patent: Nov United States Patent (19) 11 Patent Number: 4,707,352 Stavrianpoulos 45 Date of Patent: Nov. 17, 1987 (54) METHOD OF RADIOACTIVELY LABELNG OTHER PUBLICATIONS DAGNOSTIC AND THERAPEUTICAGENTS CONTAINING ACHELATING GROUP Meares et al., Proc. Nat. Acad. Sci. USA, 69, 3718-3722 (1972). 75 Inventor: Jannis G. Stavrianpoulos, New York, DeRiemer et al., J. Med. Chem., 22, 1019-1023 (1979). N.Y. Primary Examiner-Christine M. Nucker Attorney, Agent, or Firm-James F. Haley, Jr. (73) Assignee: Enzo Biochem, Inc., New York, N.Y. 57 ABSTRACT A method of forming a therapeutic or diagnostic agent 21 Appl. No.: 575,397 labeled with a radioactive metal ion, which comprises: contacting an unlabeled therapeutic or diagnostic agent, 22) Filed: Jan. 30, 1984 consisting of a substantially non-metal chelating portion and a chelating portion capable of chelating with the (51) Int, C. ...................... A61K 43/00; A61K 49/02 radioactive metal ion, with an ion transfer material (52) U.S. Cl. ......................................... 424/1.1; 424/9; having the radioactive metal ion bound thereto and 424/85; 424/88; 424/89; 424/92; 530/350; having a binding affinity for the radioactive metal less 530/402; 530/403; 530/405; 530/406; 536/1.1; than the binding affinity of the chelating portion for the 536/26; 536/27; 536/28 radioactive metal ion, wherein prior to contacting the (58) Field of Search ........................ 424/1.1, 9, 85, 88, chelating portion is unchelated or is chelated with a 424/89, 92; 530/350, 402, 403, 405, 406; second metal having a binding affinity with the chelat 536/26-28, 1.1 ing portion less than the binding affinity of the radioac tive metal ion, whereby a radiolabeled therapeutic or (56) References Cited diagnostic agent is formed by the contacting, and sepa U.S. PATENT DOCUMENTS rating the radiolabeled therapeutic or diagnostic agent from the ion transfer material, is disclosed along with 3,936,440 2/1976 Nath ...................................... 536/25 various components and kits useful in practicing this 4,043,998 8/1977 260/501.1 4,057,615 11/1977 Bardy et al. ...... ... 424/1.1 method and several variations thereof. 4,272,503 6/1981 Camin et al. ... 424/1.1 4,305,922 12/1981 Rhodes ................................. 424/1.1 17 Claims, No Drawings 4,707,352 1. 2 materials and, when imaging agents are involved, METHOD OF RADIOACTIVELY LABELING greatly increased the amount of background radiation DAGNOSTIC AND THERAPEUTICAGENTS present. Furthermore, health hazards to the technicians handling these materials and hazards associated with CONTAINING ACHELATING GROUP disposing of the associated waste generated at various BACKGROUND OF THE INVENTION steps of synthesizing labeled compounds made the han 1. Field of the Invention dling of radioactively labeled compounds difficult. The present invention relates to methods of radioac Typically, as disclosed by Scheinberg and Strand in tively labeling diagnostic and therapeutic agents and is the article cited above, a bifunctional chelate was cou particularly related to systems in which a metal ion is 10 pled to a target molecule, after which any metal ions bound to the labeled molecule through a chelating present were removed by dialysis, typically against a group. solution containing low molecular weight chelating 2. Description of the Prior Art molecules such as EDTA. The chelate-conjugated mol The use of radioactively labeled diagnostic and thera ecules were then labeled with a radioactive metal solu peutic agents has become routine practice in clinical 15 tion, after which free metal was removed, for example, and analytical laboratories throughout the world. Such by ion-exchange chromatrography. The resulting la radioactively labeled compounds are used both in vitro beled product was then stored and later used in the (for example, in radioimmunoassay systems) and in vivo diagnostic or therapeutic process. Using such proce (for example, both in diagnostic imaging techniques and dures, considerable handling of the radioactive material in radiation therapy techniques). 20 and generation of radioactive waste occurred, a disad Initially, the number of radioisotopes that could be vantage not overcome by any teachings of the prior art. firmly attached to the typical organic molecules used as diagnostic and therapeutic agents was limited. The diffi SUMMARY OF THE INVENTION culty in forming stable carbon-metal bonds prevented The present invention provides a universal method the early utilization of many radioactive metals and 25 which can be used to radioactively label any diagnostic typically limited radioisotopes used to label organic or therapeutic agent having a ligand portion thereof molecules to isotopes of phosphorus, carbon, hydrogen, which is capable of binding with a radioactive metal and iodine. ion. The labeling occurs immediately prior to the utili Recently, a new approach has enabled the labeling of 30 zation of the agent and produces little or no radioactive such agents with metal ions. In this approach, a chelat Waste. ing moiety is covalently attached to the molecules of The invention provides a method of radioactively interest, and a radioactive ion is then chelated by the labeling a diagnostic or therapeutic molecule with a sequestering groups of the chelator. The chelating moi radioactive metal ion, which comprises: eties which have generally been used for this purpose in (A) contacting the prior art have been analogues or derivatives of eth 35 (1) an unlabeled therapeutic or diagnostic agent com ylenediaminetetraacetic acid (EDTA), although many prising variations have also occurred. For example, in 1968, W. (a) a substantially non-metal chelating portion at F. Benisek and F. M. Richards suggested the covalent tached to bonding of chelating groups based on methylpicotinimi (b) a chelating portion capable of substantially date to the amino function of a protein molecule in 40 order to facilitate crystallographic investigation of pro chelating with said radioactive metal ion, with tein structure by binding a metal to the chelating site on (2) an ion transfer material having said radioactive . the protein J. Biol. Chem..., 2434267-4271 (1968)). Like metalion bound thereto and having a binding affin wise, in U.S. Pat. No. 4,043,998, the compound 1-(p- ity of said chelating portion for said radioactive benzenediazonium)ethylenediaminetetraacetic acid, 45 metal ion, said to be a powerful chelating agent which can be wherein prior to said contacting said chelating por bonded strongly to proteins through its diazonium tion is unchelated or is chelated with a second metal group, was disclosed. In Science, 209, 295-297 (1980), B. ion having a binding affinity with said chelating por A. Khaw et al. disclosed the use ofa bifunctional chelat tion less than the binding affinity of said radioactive ing agent, diethylenetriaminepentaacetic acid (DTPA) 50 metal ion, whereby a radiolabeled therapeutic or to label an antibody with a radioactive isotope and the diagnostic agent is produced by said contacting; and subsequent use of that labeled antibody to image experi (B) separating said radiolabeled therapeutic or diagnos mental myocardial infarctions in dogs. The metal bind tic agent from said ion transfer material. ing efficiencies of the resulting compounds were low, Additionally, the labeling method described above however, since attachment occurred through one of the 55 can be used as the first step of a diagnostic or therapeu carboxylate groups which would normally have partici tic process, after which the normal steps of the process pated in binding to the metal ion. Similarly, D. A. are carried out in their usual fashion. Typical of such Scheinberg and O. A. Gansow taught in Science, 215 processes are radioimmunoassay and in vivo diagnostic 1511-1513 (1982), the use of DTPA and EDTA analogs and therapeutic techniques. covalently bonded to antibodies to image mouse ery 60 The invention provides, in addition to the aforemen throid tumors. tioned process, various elements and components to be Unfortunately, the radioactively labeled materials used therein in the form of kits comprising these compo previously available suffered from several disadvan nents and other components used in the various pro tages. This was particularly true for imaging agents and CSSS. other molecules labeled with an isotope of high specific 65 In essence, the invention is based on the discovery activity. The short half-lives of the radioactive isotopes that, if conditions are properly selected, hazards involv used and the radiation-induced degradation of the la ing radioactive waste and radioactive products can be beled molecules greatly reduced the shelf-lives of these ameliorated by utilizing an ion transfer process as the 4,707,352 3 4. last step prior to the ultimate use of a therapeutic or occurring compound), to be recognized by its corre diagnostic molecule having a radiolabel. Thus, the ne sponding monoclonal or polyclonal antibody; an anti cessity of handling radioactive material during the prep body portion, to be recognized by its corresponding aration of a diagnostic or therapeutic molecule is antigen; a lectin portion, to be recognized by its sugar; avoided and no waste radioactivity is generated in the 5 a sugar portion, to be recognized by its lectin; a hor clinical or analytical laboratory environment. Uses for mone portion, to be recognized by its receptor; a recep the process, system, and components of the present tor portion, to be recognized by its hormone; an inhibi invention are unlimited and include all of the uses to tor portion, to be recognized by its enzyme; an enzyme which prior art techniques involving radiolabeled diag portion, to be recognized by its inhibitor; a cofactor nostic and therapeutic molecules have been put as well O portion, to be recognized by a cofactor enzyme binding as other uses disclosed herein. site; a cofactor enzyme binding site portion, to be recog nized by its cofactor; a binding ligand, to be recognized DESCRIPTION OF THE PREFERRED by its substrate and vice versa (e.g., biotin-avidin); or EMBODIMENTS any permutation or combination thereof.
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