KR20170037727A - Bone Metastasis radioactive diagnostic kit and manufacturing method thereof - Google Patents
Bone Metastasis radioactive diagnostic kit and manufacturing method thereof Download PDFInfo
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Abstract
Description
The present invention relates to a radioactive label kit for diagnosing bone cancer and a method for producing the same.
It is known that bone cancer is caused by metastasis from prostate cancer, breast cancer, lung cancer and the like, and its mortality rate is high. For this reason, there is a great expectation for the development of diagnosis and treatment methods of bone cancer in the field of radioactive nuclear medicine.
In general, bone cancer can be diagnosed by using phosphonate compounds such as MDP (Methyl diphosphate) labeled with Tc-99m or Ethylenediamine-N (N, N ', N'-tetrakisethylenephosphate) A single-photon emission computed tomography (SPECT) imaging technique is used.
Recently, the development of PET imaging technology has increased the resolution and sensitivity of imaging, and the development of F-18-fluoride-based bone imaging imaging method, which is a commercial imaging diagnostic tool, is proceeding rapidly. However, since F-18-fluoride has a disadvantage of lacking specificity for bone cancer, a more specific imaging agent is required. In addition, since the production of F-18 requires expensive cyclotron, Ga-68 can be produced in an inexpensive and highly portable generator, and thus it is expected to develop a PET imaging agent using Ga-68.
DOTMP (1,4,7,10-tetraazacyclodecane-1,4) for use as a therapeutic agent for bone cancer together with therapeutic radioisotopes samarium (Sm-153), holmium (Ho-166), and lutein , 7,10-tetramethylenephosphonicacid) have been developed. However, there is no study on the bonding with Ga-68.
The present invention provides a process for preparing a polyazamacrocyclic phosphonate compound, comprising: (a) preparing a composition comprising a polyazamacrocyclic phosphonate compound; (b) eluting the Ga-68 solution from the Ge-68 / Ga-68 generator; And (c) mixing the composition prepared in step (a) with the Ga-68 solution eluted in step (b), followed by heating, to provide a method for manufacturing a radiological marker kit for bone cancer diagnosis .
However, the technical problem to be solved by the present invention is not limited to the above-mentioned problems, and other matters not mentioned can be clearly understood by those skilled in the art from the following description.
The present invention provides a process for preparing a polyazamacrocyclic phosphonate compound, comprising: (a) preparing a composition comprising a polyazamacrocyclic phosphonate compound; (b) eluting the Ga-68 solution from the Ge-68 / Ga-68 generator; And (c) mixing the composition prepared in step (a) with the Ga-68 solution eluted in step (b), followed by heating.
In one embodiment of the present invention, there is provided a radioactive label kit for bone cancer diagnosis wherein a polyazamacrocyclic phosphonate compound is labeled with Ga-68.
The present invention relates to a kit for quantitatively optimizing a radiological marker kit for bone cancer diagnosed in which a polyazamacrocyclic phosphonate compound is labeled with Ga-68, which can increase the yield of marking of bone cancer without further purification, It is possible to lower the possibility of inducing side effects due to the administration, and to secure excellent radiochemical stability and to be used as a PET imaging agent and the like.
1 shows a method of manufacturing a radiological marker kit for bone cancer diagnosis according to an embodiment of the present invention.
Figure 2 is a photograph showing the DOTMP composition prepared in vial form.
3 is a graph showing the results of thin layer chromatography (TLC) measurement of (A) Ga-68 solution and (B) Ga-68 labeled DOTMP.
4 is a graph showing the result of (A) measurement of thin layer chromatography (TLC) of Ga-68 labeled DOTMP and (B) evaluation of radiochemical stability of Ga-68 labeled DOTMP.
5 is a graph showing the yield of radioactive labeling according to the content of DOTMP when the radioactive level of Ga-68 for labeling is 1 MBq.
The present inventors have made quantitative optimization of bone cancer detection radioactive labeling kit labeled with Ga-68 in a polyazamacrocyclic phosphonate compound for use as a imaging agent for PET (Positron Emission Tomography) and the like, Accuracy and yield can be improved, and the present invention has been completed.
Since the Ga-68 labeled polyazamacrocyclic phosphonate compound prepared by the method according to the present invention has a stronger bond than the conventional EDTMP, it is used as an imaging agent for PET (Positron Emission Tomography) It is unlikely to be dismantled. Therefore, the yield of marking of bone cancer is high, and there is an advantage that the possibility of causing side effects in the body can be lowered.
The present invention provides a process for preparing a polyazamacrocyclic phosphonate compound, comprising: (a) preparing a composition comprising a polyazamacrocyclic phosphonate compound; (b) eluting the Ga-68 solution from the Ge-68 / Ga-68 generator; And (c) mixing the composition prepared in step (a) with the Ga-68 solution eluted in step (b), followed by heating.
1 shows a method of manufacturing a radiological marker kit for bone cancer diagnosis according to an embodiment of the present invention.
As shown in FIG. 1, a radioactive labeling kit for bone cancer diagnosis according to an embodiment of the present invention comprises a composition comprising DOTMP, which is a kind of polyazamacrocyclic phosphonate compound (S1). The Ga-68 solution is eluted and purified from the Ge-68 / Ga-68 generator (S2). Thereafter, distilled water is added to the DOTMP composition (S3), followed by mixing with a Ga-68 solution and heating (S4).
Each step will be described in detail below.
First, a method for producing a radioactive label kit for bone cancer diagnosis according to the present invention comprises the steps of (a) preparing a composition comprising a polyazamacrocyclic phosphonate compound.
Specifically, the preparation of the composition comprising the polyazamacrocyclic phosphonate-based compound is carried out by using a polyazamacrocyclic phosphonate-based compound; a buffer solution having a pH ranging from 3 to 5; And ascorbic acid can be purified and dried.
The polyazamacrocyclic phosphonate-based compound is a DOTA derivative chelate compound to be described later, and has a stable chelate with Ga-68 as compared with the conventional EDTMP, and thus has a long storage time and excellent chemical stability, as a target compound.
As used herein, "DOTA" refers to 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraazacyclododecane-1,4,7,10- tetraacetic acid) and is a metal-compatible ligand compound. These compounds are metal-compatible ligand compounds that are used in PET imaging, and include radioactive metals such as Cu-64, Cu-67, Ga-68, Zr-89, Y-86, Y-90, Lu- 111, and has an advantage of being able to reduce the cytotoxicity caused by the radioactive material because it acts to remove the radioactive substance from the body.
The polyazamacrocyclic phosphonate-based compound is a DOTA derivative chelate compound, and 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetramethylenephosphonic acid (1,4,7 , 10-tetraazacyclododecane-1,4,7,10-tetramethylene phosphonic acid (DOTMP) and 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid- 4-amino-1-hydroxybutylidene-1,1-bisphosphonate; DOTA-HBP ) And 4-bisphosphonomethylcarbamoylmethyl-7,10-biscarboxymethyl-1,4,7,10-tetraazacyclododec-1-yl acetic acid (4 - {[ methylbenzyl) methyl] -7,10-bis (carboxymethyl) -1,4,7,10-tetraaza cyclododec-1-yl acetic acid, BPAMD), more preferably at least one selected from the group consisting of 1 , 4,7,10-tetraazacyclododecane-1,4,7,10-tetramethylene < / RTI > (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetramethylene phosphonic acid (DOTMP)), but it is not limited thereto.
The buffer solution has a pH ranging from
The ascorbic acid is used as a stabilizer, and the storage stability of the mixed solution can be enhanced. The molar concentration of ascorbic acid may be 0.1 M to 0.5 M, preferably 0.2 M to 0.25 M, but is not limited thereto.
At this time, the volume ratio of the buffer solution and the ascorbic acid is preferably 10: 1 (v / v) to 1: 1 (v / v), more preferably 1: 1 (v / v) It does not.
The content of the polyazamacrocyclic phosphonate compound per radioactive level of Ga-68 for labeling is preferably 0.2 쨉 g / MBq to 1 / / MBq, more preferably 0.6 / / MBq to 1 / / MBq And most preferably 0.8 μg / MBq to 1 μg / MBq, but is not limited thereto.
Generally, targeting compounds that do not bind to radioactive isotopes cause a shielding effect on the target disease site, thereby preventing the compounds exhibiting pharmacological action from accumulating on the disease site. Therefore, it is necessary to optimize the content of the polyazamacrocyclic phosphonate compound per radioactive level of Ga-68 for labeling.
In the case of conventional EDTMP, the optimum content of EDTMP for labeling Ga-68 having a radioactivity level of 1 MBq is determined from 120 내지 to 189 ㎍. In the present invention, a polyazamacrocyclic phosphonate compound such as DOTMP is used The amount of the target compound to be used can be remarkably reduced, and the possibility of causing an adverse reaction in the body can be greatly reduced by an excess amount of the target compound.
The prepared composition may be formed as an empty white layer located on the inner wall of the vial.
(B) eluting the Ga-68 solution from the Ge-68 / Ga-68 generator. The method for preparing a radioactive label kit for bone cancer diagnosis according to the present invention comprises the steps of:
The Ge-68 / Ga-68 generator may be a Ge-68 / Ga-68 isotope generator.
The Ge-68 / Ga-68 generator is easy to produce Ga-68 on demand in the field according to demand, it is easy to supply and supply raw materials, and has a short half-life.
When the eluted Ga-68 solution is of low purity, it can be further purified using a cation exchange resin. In the present invention, an SCX (Si-CH 2 CH 2 CH 2 SO 3 H) cation exchange cartridge was used as the cation exchange resin.
Through the above purification, the Ga-68 may be contained in an amount of 95 to 99 wt% based on the total weight of the Ga-68 solution.
Next, the method for preparing a radiological marker kit for diagnosing bone cancer according to the present invention comprises mixing a Ga-68 solution eluted in the step (b) and heating the composition prepared in the step (a).
Prior to the mixing, distilled water may be further added to the composition prepared in the step (a). At this time, the addition can be performed by various known methods, but in the present invention, distilled water is injected using a syringe made of a plastic needle. The distilled water may be third distilled water, and the volume of the distilled water may be 0.1-1 ml.
Specifically, the composition prepared in the step (a) may be prepared into a vial by mixing the Ga-68 solution eluted in the step (b), and then heated at a temperature of 80 to 110 ° C for 7 to 10 minutes Lt; / RTI >
That is, the heating temperature is preferably 80 ° C to 110 ° C, more preferably 90 ° C to 110 ° C, but is not limited thereto. At this time, if the heating temperature is lower than the above range, the polyazamacrocyclic phosphonate compound and Ga-68 are not sufficiently bonded, resulting in a lower yield of marking of bone cancer, Problems may arise. Further, when the heating temperature exceeds the above range, there is a problem that the mixed solution in the vial is boiled.
On the other hand, the heating time may be varied to control the total heating amount depending on the temperature range.
The present invention also provides a radioactive label kit for diagnosing bone cancer, wherein Ga-68 is labeled on a polyazamacrocyclic phosphonate compound.
The radioactive label kit for diagnosing bone cancer is prepared according to the above method. As described above, the polyazamacrocyclic phosphonate compound is a 1,4,7,10-tetraazacyclododecane-1,4 Tetraazacyclododecane-1,4,7,10-tetramethylene phosphonic acid (DOTMP) and 1,4,7,10-tetraazacyclododecane-1 , 4,7,10-tetraacetic acid-4-amino-1-hydroxybutylidene-1,1-bisphosphonate (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid- 4-amino-1-hydroxybutylidene-1,1-bisphosphonate DOTA-HBP) and 4-bisphosphonomethylcarbamoylmethyl-7,10-biscarboxymethyl-1,4,7,10-tetraazacyclododi Bis (carboxymethyl) -1,4,7,10-tetraaza cyclododec-1-yl acetic acid) in the presence of a base such as < RTI ID = acetic acid, BPAMD), and more preferably at least one selected from the group consisting of And 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetramethylene phosphonic acid ; DOTMP), but is not limited thereto.
The radiological marker kit for diagnosing bone cancer can be used as a PET imaging agent and the like, and a method for diagnosing osteoma can be provided.
Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are provided only for the purpose of easier understanding of the present invention, and the present invention is not limited by the following examples.
Example
A mixed solution was prepared by mixing 0.25 ml of 1 M ammonium acetate and 0.25 ml of 0.4 M acrobic acid as a buffer solution having a DOTMP of 400 μg and a pH of 4.5 and filtering paper (Millipore®, 0.2 쨉 m), and 0.5 ml of the solution was dispensed into glass vials. The resulting solution was rapidly frozen at -53 캜 and vacuum-dried to prepare a DOTMP composition.
FIG. 2 is a photograph showing a DOTMP composition prepared in the form of a vial. The DOTMP composition was found to be an empty white layer on the inner bottom wall of the vial, and it was confirmed that it was formed by freeze-drying.
The Ga-68 solution was eluted from the Ge-68 / Ga-68 isotope generator (ITG, Germany) and purified using SCX cation exchange resin.
At this time, the radioactivity level of Ga-68 was measured with a Wallac 1470 automatic gamma meter (PerkinElmer Life Science, Massachusetts, USA) and an ionization chamber (
To the DOTMP composition, 0.5 ml of tertiary distilled water contained in a glass vial was added using a syringe and then mixed with the purified Ga-68 solution, and the mixture was heated in a glass vial at 100 ° C for 7 minutes to obtain Ga-68 Labeled DOTMP was finally prepared.
At this time, in order to measure the radiochemical purity and label yield of Ga-68 labeled DOTMP, the development ratio which can confirm the separation between the components was firstly measured by thin layer chromatography (TLC).
Specifically, 0.5 M sodium citrate (Na 2 HC 6 H 5 O 7 ) buffer solution of pH 4.5 was used as a developing solvent, and 2 to 4 μl of a Ga-68 labeled DOTMP And the development rate was analyzed by a thin layer chromatography linear analyzer (TLC-linear analyzer).
The term " rate of flow (Rf) "in the present specification is a qualitative analytical indicator for confirming the degree of separation between components contained in a solution. The rate of flow depends on the moving speed of the substance corresponding to the solute in the developing solvent, Relatively heavier materials have a lower developmental rate than light ones. Generally, the expansion rate is defined as the ratio of the straight line distance from the origin of the linear distance from the origin to the final detection position of the developing solvent to the final detection position of the substance corresponding to the solute, it means.
3 is a graph showing the results of thin layer chromatography (TLC) measurement of (A) Ga-68 solution and (B) Ga-68 labeled DOTMP.
As shown in FIG. 3, it was confirmed that the Ga-68 solution removed the impurities having a development ratio of 0.03 ± 0.01 and the expansion ratio of Ga-68 was 0.99 ± 0.01. The expansion ratio of the Ga-68 labeled DOTMP was 0.82 ± 0.01, respectively.
On the other hand, the radiochemical purity and the labeling yield value were obtained from the value obtained by dividing the radioactivity measured at the final detection point of the Ga-68 labeled DOTMP indicated in the silica gel detection report by the total radioactivity to be described later. The total radioactivity is the sum of the final detection point of the impurity indicated on the silica gel detection paper, the final detection point of Ga-68 and the final detection point of the Ga-68 labeled DOTMP.
4 is a graph showing the result of (A) measurement of thin layer chromatography (TLC) of Ga-68 labeled DOTMP and (B) evaluation of radiochemical stability of Ga-68 labeled DOTMP.
As shown in Fig. 4, the initial radiochemical purity of the Ga-68 labeled DOTMP is 98% or more, and the radiochemical purity change rate is at least ± 4 hours after preparation, which corresponds to a time much longer than the half- 1.0% or less, it was confirmed that there was no decrease in the radiochemical purity, and it was evaluated that the radiochemical stability was excellent.
5 is a graph showing the yield of labeling according to the content of DOTMP when the radioactive level of Ga-68 for labeling is 1 MBq.
As shown in FIG. 5, in order to determine the threshold value for the content of DOTMP for labeling Ga-68 having a radiation level of 1 MBq, the label yield of Ga-68 labeled DOTMP containing 0 to 1.0 μg of DOTMP was measured As a result, it was confirmed that the label yield increased to 80% or more when DOTMP contained 0.2 ㎍ or more. Also, it was confirmed that the increase rate of label yield was decreased when DOTMP was contained more than 0.8 ㎍.
Therefore, it was confirmed that the optimal content of DOTMP for labeling Ga-68 having a radioactivity level of 1 MBq was determined at 0.8 μg, which can significantly reduce the amount of use compared to the conventional EDTMP.
It will be understood by those skilled in the art that the foregoing description of the present invention is for illustrative purposes only and that those of ordinary skill in the art can readily understand that various changes and modifications may be made without departing from the spirit or essential characteristics of the present invention. will be. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.
Claims (10)
(b) eluting the Ga-68 solution from the Ge-68 / Ga-68 generator; And
(c) mixing the Ga-68 solution eluted in the step (b) into the composition prepared in the step (a) and then heating
METHOD FOR PRODUCING RADIOLOGICAL LABELING KIT FOR BONE TISSUE DIAGNOSIS.
In the step (a), the polyazamacrocyclic phosphonate-based compound is 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetramethylenephosphonic acid (1,4,7, Tetraazacyclododecane-1,4,7,10-tetramethylenephosphonic acid (DOTMP) and 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid-4-amino- Tetraazacyclododecane-1,4,7,10-tetraacetic acid-4-amino-1-hydroxybutylidene-1,1-bisphosphonate (DOTA-HBP) and 4 Bisphosphonemethylcarbamoylmethyl-7,10-biscarboxymethyl-1,4,7,10-tetraazacyclododec-1-yl acetic acid (4 - {[(bis (phosphono methyl) carbamoyl] methyl} -7,10-bis (carboxymethyl) -1,4,7,10-tetraaza cyclododec-1-yl acetic acid, BPAMD)
METHOD FOR PRODUCING RADIOLOGICAL LABELING KIT FOR BONE TISSUE DIAGNOSIS.
In the step (a), the polyazamacrocyclic phosphonate compound; a buffer solution having a pH ranging from 3 to 5; And ascorbic acid are purified and dried.
METHOD FOR PRODUCING RADIOLOGICAL LABELING KIT FOR BONE TISSUE DIAGNOSIS.
Wherein the molar concentration of the buffer solution is 0.1 M to 0.4 M, the molar concentration of the ascorbic acid is 0.1 M to 0.5 M, the volume ratio of the buffer solution and the ascorbic acid is 10: 1 (v / v) to 1: (v / v) phosphorus
METHOD FOR PRODUCING RADIOLOGICAL LABELING KIT FOR BONE TISSUE DIAGNOSIS.
The content of the polyazamacrocyclic phosphonate compound per gram of radioactive level of Ga-68 to be labeled in the step (a) is 0.2 / / MBq to 1 / / MBq
METHOD FOR PRODUCING RADIOLOGICAL LABELING KIT FOR BONE TISSUE DIAGNOSIS.
After elution in the step (b), purification using a cation exchange resin
METHOD FOR PRODUCING RADIOLOGICAL LABELING KIT FOR BONE TISSUE DIAGNOSIS.
The Ga-68 is contained in an amount of 95 to 99 wt% based on the total weight of the Ga-68 solution
METHOD FOR PRODUCING RADIOLOGICAL LABELING KIT FOR BONE TISSUE DIAGNOSIS.
In step (c), distilled water is further added to the composition prepared in step (a) before mixing
METHOD FOR PRODUCING RADIOLOGICAL LABELING KIT FOR BONE TISSUE DIAGNOSIS.
In the step (c), the heating is carried out at a temperature of 80 ° C to 110 ° C for 7 minutes to 10 minutes
METHOD FOR PRODUCING RADIOLOGICAL LABELING KIT FOR BONE TISSUE DIAGNOSIS.
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