CN101575355B - <99m>Tc marked daunorubicin dithiocarbamate composition and preparation method and applications thereof - Google Patents
<99m>Tc marked daunorubicin dithiocarbamate composition and preparation method and applications thereof Download PDFInfo
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Abstract
The invention discloses a <99m>Tc labelled daunorubicin dithiocarbamate complexes, including a complex consisting of <99m>TcN-DAUDTC and <99m>TcO-DAUDTC, and a preparation method and applications thereof. The complexes uses a (<99m>Tc-N)<2+> nucleus or a (<99m>TcO)<3> nucleus as a central nucleus, and has a geometrical configuration of irregular square pyramid, and four sulphur atoms provided by two DAUDTC ligand molecules are positioned at four points of the bottom of the irregular square pyramid. The complexes are high in radiochemical purity, and good in stability. The complexes of <99m>TcN-DAUDTC and <99m>TcO-DAUDTC have higher uptake value of tumors and good retention in tumors, and good target-to-nontarget organ ratio of the tumor/muscle and so on. Therefore, the complexes are a new developer of tumors, with popularization and application values.
Description
Affiliated technical field
The present invention relates to
99mTc mark radiopharmaceutical chemistry and clinical nuclear medicine technical field relate to a kind of specifically
99mTc mark daunorubicin dithiocarbamate complexes and preparation method and application.
Background technology
Malignant tumour has become one of maximum arch-criminal of serious harm human health.A large amount of experiments show that in the tumor treatment process, the early diagnosis of tumour is most important.
99mTc becomes one of radionuclide that present nuclear medicine is the most frequently used in checking, prospect is the most wide because of its good nulcear properties and advantage such as cheap and easy to get, therefore when the PET medicine becomes the research focus, use
99mThe radiopharmaceutic research of the novel tumor of Tc mark causes that still people show great attention to.
99mIn the development of Tc tumor developer, an interesting phenomenon is arranged is exactly the medicine that is commonly used for myocardial perfusion imaging clinically as
99mTc-MIBI,
99mTc-tetrofosmin,
99mCationic complexes such as Tc-Q12 all can be used as close tumor positive imaging agent, especially
99mTc-MIBI is clinical as close tumor developer widespread use.But
99mAlso there are some shortcomings in Tc-MIBI as tumor developer, and its picked-up in liver is high to influence its imaging results at abdominal tumor, so is necessary to develop the tumor developer of better effects if.
In addition, chemotherapy failure phenomenon takes place in regular meeting in the clinical treatment tumour process, and the multidrug resistance that this is main and tumour cell (as breast cancer cell, lung carcinoma cell and soft tissue neoplasm cell etc.) produces (multidrug resistance, MDR) relevant.The factor that influences tumour MDR is a lot, and wherein the overexpression of the P-glycoprotein (P-gp) of MDR genes encoding causes the important factor of MDR often, and the tumour cell of P-gp overexpression can be discharged the extracellular with chemotherapeutics, thereby causes the chemotherapy of tumors failure.At present, the method for detection P-gp has immunohistochemistry technique, polymerase chain reaction,PCR, flow cytometer, Western Blot method, radioautograph etc.These technology all need examination of living tissue, carry out external qualitative and quantitative analysis, have traumaticly, are difficult for generation, the development of dynamic monitoring MDR, and the tolerance range of being tested, the differences between samples of tumour and the susceptibility and the specific restriction of various technology.If can before oncotherapy, estimate to MDR, in chemotherapy process and after the chemotherapy, the change of dynamic monitoring MDR, help cancer therapy drug selection, chemotherapy regimen formulation and curative effect estimated, so the method for monitoring and evaluation tumour cell MDR has important clinical application value in the development body.Transhipment substrate with the P-gp of radioisotope labeling carries out the P-gp functional image as the Geigers probe, and the expression level of P-gp is estimated on non-invasive ground in vivo, has great importance.
Up to now, the P-gp functional image agent of the more 99mTc mark of research mainly contains
99mTc-MIBI,
99mTc-tetrofosmin and
99mTc-Q class etc.+1 valency cationic complexes and novel technetium carbonyl isocyanide complex
99mTc-CO-MIBI, wherein
99mTc-MIBI is the most frequently used clinically P-gp functional image agent.Because the transhipment substrate of P-gp can be micromolecular lipotropy ion, therefore
99mTc-MIBI also can be transported by P-gp.Again because of
99mThe Tc-MIBI plasma clearance is too fast so that can not obtain best picked-up in tumor tissues, and higher at the radioactive uptake of tissues such as liver kidney, makes the video picture of abdomen tumor of pelvic cavity fuzzy, and the P-gp that has limited abdominal tumor detects.So ideal
99mThe P-gp functional image agent of Tc mark still remains to be explored.
Also be an important directions of development tumor developer in recent years with the radioisotope labeling antitumor drug.Positron radionuclide as
11The antitumor drug of regarded as the P-gp of C mark transhipment substrate as
11C-colchicine (Colchicine),
11C-daunorubicin (Daunorubicin) and
11C-verapamil (Verapamil) etc. can be used as P-gp function PET video picture research, in addition
18The F mark
18F-idarubicin also has relevant report as the PET tracer agent of potential monitoring MDR.But since positron radionuclide as
11C,
18F etc. are cost an arm and a leg by accelerator production, are difficult for applying.Therefore research
99mThe antitumor drug such as the daunorubicin of regarded as the P-gp transhipment substrate of Tc mark have important practical significance as the agent of P-gp functional image.
Summary of the invention
The purpose of this invention is to provide a kind of radiochemical purity height, good stability, prepare easyly, be applied in the especially multidrug resistance video picture of tumor imaging field
99mTc mark daunorubicin dithiocarbamate complexes (Daunorubicindithiocarbamate) is called for short
99mThe Tc-DAUDTC title complex; The preparation method of its title complex also is provided simultaneously.
In order to achieve the above object, the present invention by the following technical solutions: a kind of
99mTc mark daunorubicin dithiocarbamate complexes (
99mThe Tc-DAUDTC title complex), comprise
99mTcN-DAUDTC and
99mThe TcO-DAUDTC title complex,
Wherein:
99mIts structural formula of TcN-DAUDTC is:
This title complex with [
99mTc ≡ N]
2+Nuclear has a PYR geometric configuration of irregular pros for centronucleus, and wherein the N atom in the Tc ≡ N triple bond is positioned at vertex position, and four sulphur atoms that two DAUDTC ligand moleculars provide are positioned at four points of bottom surface.
And
99mThe TcO-DAUDTC title complex, its structural formula is:
This title complex with [
99mTc (V) O]
3+Be centronucleus, have a PYR geometric configuration of irregular pros, wherein the O atom in the Tc=O key is positioned at vertex position, and four sulphur atoms that two DAUDTC ligand moleculars provide are positioned at four points of bottom surface.
99mTc mark daunorubicin dithiocarbamate complexes (
99mTc-DAUDTC) preparation method is as follows:
A. part DAUDTC's is synthetic:
The daunomycin hydrochloride of 0.01mol is added in the reaction vessel, in reaction vessel, add the NaOH methanol solution, slowly drip CS then
2, stirring 2h-3h, the entire reaction course temperature will be controlled at below 10 ℃, and suction filtration gets red solid then, uses recrystallizing methanol, and get red powder and be DAUDTC,
Its synthetic route is:
B.
99mThe preparation of TcN-DAUDTC:
With 37～370MBq's
99mTcO
4 -Leacheate 1-5mL joins in the SDH froze-dried kit, fully shakes up, and after solid dissolved fully, room temperature (20～30 ℃) reaction down obtained in 15～30 minutes
99mThe TcN midbody solution.With 1mL concentration is that the ethanolic soln of the part of 1g/L joins above-mentioned
99mIn the TcN midbody solution, in boiling water bath, reacted 15 minutes behind the mixing, obtain
99mThe TcN-DAUDTC title complex;
99mLigand exchange reaction is adopted in the preparation of TcN-DAUDTC, and its reaction scheme is as follows:
99mTcO
4 -+SDH+SnCl
2·2H
2O+PDTA→[
99mTcN]
int 2+[
99mTcN]
int 2++DAUDTC→
99mTcN-DAUDTC
C.
99mThe preparation of TcO-DAUDTC:
With 37～370MBq's
99mTcO
4 -Leacheate 1-5mL joins in the GH froze-dried kit, fully shakes up, and after solid dissolved fully, 20～30 ℃ of following reactions obtained in 15～30 minutes
99mThe TcO-GH midbody solution; With 1mL concentration is that the ethanolic soln of the part of 1g/L joins above-mentioned
99mIn the TcO-GH midbody solution, in boiling water bath, placed 60 minutes behind the mixing, promptly obtain
99mThe TcO-DAUDTC title complex;
99mLigand exchange reaction is adopted in the preparation of TcO-DAUDTC, and its reaction scheme is as follows:
99mTcO
4 -+SnCl
2·2H
2O+GH→
99mTcO-GH
99mTcO-GH+DAUDTC→
99mTcO-DAUDTC
Above-mentioned title complex is novel
99mThe Tc tumor developer, wherein
99mTcN-DAUDTC with [
99mTc ≡ N]
2+Nuclear is centronucleus,
99mTcO-DAUDTC with [
99mTc (V) O]
3+Nuclear is centronucleus, radiochemical purity height, good stability.By aforesaid method synthetic title complex, its radiochemical purity is all greater than 90%.
The bio distribution experimental result shows in the tumor-bearing mice body
99mTcN-DAUDTC and
99mThe TcO-DAUDTC title complex has higher picked-up and is detained preferably in tumour, the ratio of target/non-target organ that tumour/muscle etc. are important is also better, novel tumor developer be can become, especially further investigation and popularization are worth as the tumor multi-medicine drug-resistant developer.
Will
99mTcN-DAUDTC,
99mTcO-DAUDTC the intravital bio distribution data of tumor-bearing mice with clinically as the tumor multi-medicine drug-resistant developer
99mTc-MIBI compares, and the results are shown in Table 1.
Table 1
99mTcN-DAUDTC,
99mTcO-DAUDTC with
99mThe biological data contrast (x ± s, ID%/g, 4h p.i.) of Tc-MIBI
From the result of table 1 as can be seen, two kinds of title complex picked-ups in tumour all than
99mThe Tc-MIBI height, and the picked-up in muscle is starkly lower than
99mTc-MIBI, still
99mThe picked-up of Tc-MIBI in blood is low.So the knurl of two kinds of title complexs/meat ratio will much larger than
99mTc-MIBI, but knurl/blood ratio much smaller than
99mTc-MIBI.By with
99mThe comprehensive contrast of the biological experimental data of Tc-MIBI illustrates that two kinds of title complexs can be used as novel tumor multi-medicine drug-resistant developer,
Above-mentioned described chemosynthesis reagent all is commercial goods, and wide material sources obtain easily.
Experiment shows,
99mTcN-DAUDTC,
99mThe performance of TcO-DAUDTC title complex is as follows:
1.
99mTcN-DAUDTC,
99mThe chromatography of TcO-DAUDTC title complex is identified:
Thin-layer chromatography chromatogram (TLC) is identified: as support, make developping agent with physiological saline with polyamide layer, the tomographic results of mensuration sees Table 2 and table 3.
Tomographic results (the R of each component of table 2
fValue)
Identify that by above-mentioned chromatography the radiochemical purity of measured marker is greater than 90%.
High performance liquid chromatography (HPLC) is identified:
99mTcN-DAUDTC title complex HPLC identifies: Shimadzu SCL-10AVP type high pressure liquid chromatograph, (25cm * 4.6mm), Packard liquid dodges analyser to Kromasil 100-5C18 reversed-phase column.Moving phase is pure water and acetonitrile, and A is pure water mutually, and B is acetonitrile mutually, and gradient is that 0.01-30minB is 100-5% mutually, and sample size 5 μ L, flow are 1mL/min.The retention time (Rt) of each component of measuring is respectively:
99mTcO
4 -: 1.8min; [
99mTcN]
Int 2+: 126min;
99mTcN-DAUDTC:2.9min, the chromatogram result of gained show,
99mThe radiochemical purity of TcN-DAUDTC title complex is greater than 95%.
99mTcO-DAUDTC title complex HPLC identifies: Shimadzu SCL-10AVP type high pressure liquid chromatograph, (25cm * 4.6mm), Packard liquid dodges analyser to Kromasil 100-5C18 reversed-phase column.Moving phase is pure water and methyl alcohol, and A is pure water mutually, and B is methyl alcohol mutually, and gradient is that 0.01-2min B is 5% mutually, and 2-30min B becomes 100% by 5%, sample size 5 μ L, and flow is 1mL/min.The retention time (Rt) of each component of measuring is respectively:
99mTcO
4 -: 2.7min;
99mTcO-GH:2.4min;
99mTcO-DAUDTC:22.10min, the chromatogram result of gained show,
99mThe radiochemical purity of TcO-DAUDTC title complex is greater than 95%.
2.
99mTcN-DAUDTC,
99mThe mensuration of the lipid of TcO-DAUDTC title complex:
(0.025mol/L) phosphate buffered saline buffer of getting 0.9mLpH7.4 adds 1.0mL n-Octanol and 0.1mL mark complex solution in centrifuge tube in the 10mL centrifuge tube, cover stopper, fully shakes up centrifugal 5min (4000r/min).Take out 0.1mL from organic phase and aqueous phase respectively then, measure the radiocounting of two-phase, and calculate its lipid P (radioactive activity of the radioactive activity/water of P=organic phase).The result shows
99mThe logP of TcN-DAUDTC is-1.11, illustrates that it is a water-soluble substances, and
99mThe logP of TcO-DAUDTC is 1.37, illustrates that it is a lipid-soluble substance.
3.
99mTcN-DAUDTC,
99mThe stability of TcO-DAUDTC title complex is measured:
The title complex that mark is good is at room temperature placed different time (1,2,3,4,5,6 hour) back and is measured its radiochemical purity, and experimental result shows
99mTcN-DAUDTC,
99mRadiochemical purity is greater than 90% after placing 6 hours for the TcO-DAUDTC title complex, and title complex is described, and at room temperature vitro stability is good, is suitable for the needs of clinical application.
4.
99mTcN-DAUDTC,
99mThe bio distribution experiment of TcO-DAUDTC in bearing mouse model:
Tail vein injection 0.10mL mark complex solution (about 7.4 * 10 from lotus S180 sarcoma model mice
5Bq), injection back 0.5h, 2h, 4h sacrificed by decapitation small white mouse.Get related organization and organs such as its blood, the heart, liver, lung, kidney, brain, tumour, muscle, bone, weigh after cleaning, and on FM-2000 type technetium analyser, survey its radiocounting, each the time item the small white mouse number be 5.Calculate every gram percentage injected dose (%ID/g) of each tissue, the results are shown in Table 4 and table 5.
Table 4
99mTcN-DAUDTC in lotus S180 sarcoma model mice body the bio distribution result (x ± s, n=5)
Table 5
99mTcO-DAUDTC in lotus S180 sarcoma model mice body the bio distribution result (x ± s, n=5)
Embodiment
Below by embodiment in detail the present invention is described in detail:
A kind of
99mTc mark daunorubicin dithiocarbamate (
99mTc-DAUDTC) title complex comprises
99mTcN-DAUDTC and
99mThe TcO-DAUDTC title complex, its preparation method is as follows:
A. part DAUDTC's is synthetic:
0.01mol daunomycin hydrochloride (analytical pure) is joined in the 50mL there-necked flask, in reaction vessel, add NaOH (analytical pure, the Beijing Chemical Plant produces) methanol solution of 4mL 5mol/L, stir in the ice-water bath, slowly drip 0.01molCS then
2(analytical pure, Shantou Xilong Chemical Factory, Guangdong) stirs 2h～3h, and the entire reaction course temperature is controlled at below 10 ℃.Suction filtration gets red solid then, uses recrystallizing methanol, gets red powder and is DAUDTC.
Infrared spectra: v (IR)/cm -1 : 34463 (OH), 29248 (CH 3 ), 2844.3 (CH 2 ), 1015.8 (C=S).Proton nmr spectra: 1 H NMR (CDCl 3 , 500MHz) δ ppm14.00 (H, s), 13.31 (H, s), 8.05 (H, d, J=7.50Hz), 7.81 (H, M), 7.42 (H, d, J=8.35Hz), 5.60 (H, m), 5.34 (H, s), 4.86 (H, d, J=9.60Hz), 4.58 (H, d, J=9.65Hz), 4.15 (H, d, J=6.65Hz), 4.11 (3H, s), 3.24 (H, d, J=18.65), 2.99 (H, dd, J 1 =18.85, J 2 =6.45Hz), 2.66 (H, s), 2.53 (H, d, J=18.50Hz), 2.44 (3H, s), 2.20 (H, s), 2.13 (H, d, J=11.5Hz), 1.46 (H, d, J=6.40Hz), 1.42 (H, d, J=6.40Hz), 1.38 (H, d, J=7.05Hz), 1.28 (3H, s).
Mass spectrum: MS (ESI): m/z 602, [M-23]
B. title complex
99mThe preparation of TcN-DAUDTC
Preparation SDH froze-dried kit: by with SDH, PDTA, SnCl
2.2H
2O is dissolved in an amount of secondary water by the weight ratio of 1-20: 1-20: 0.005-0.5, fully is sub-packed in the clean penicillin bottle, through freeze-dried back after the dissolving.
With 37～370MBq's
99mTcO
4 -Leacheate 1-5mL joins in the SDH froze-dried kit, fully shakes up, and after solid dissolved fully, room temperature (20～30 ℃) reaction down obtained in 15～30 minutes
99mThe TcN midbody solution.With 1mL concentration is that the ethanolic soln of the part of 1g/L joins above-mentioned
99mIn the TcN midbody solution, reacted 30 minutes down at boiling water bath (80～100 ℃) behind the mixing, promptly obtain described
99mThe TcN-DAUDTC title complex.
C. title complex
99mThe preparation of TcO-DAUDTC
Preparation GH froze-dried kit: by with GH, SnCl
2.2H
2O is dissolved in an amount of secondary water by 200: 1 weight ratio, fully is sub-packed in the clean penicillin bottle, through freeze-dried back after the dissolving.
With 37～370MBq's
99mTcO
4 -Leacheate 1-5mL joins in the GH froze-dried kit, fully shakes up, and after solid dissolved fully, room temperature (20～30 ℃) reaction down obtained in 20～30 minutes
99mTcO-GH solution.With 1mL concentration is that the ethanolic soln of the part of 1g/L joins above-mentioned
99mIn the TcO-GH solution, shake up, 100 ℃ of following reactions promptly obtained described in 60 minutes
99mThe TcO-DAUDTC title complex.
Claims (4)
1. one kind
99mTc mark daunorubicin dithiocarbamate complexes comprises
99mTcN-DAUDTC and
99mThe TcO-DAUDTC title complex,
Wherein:
99mThe structural formula of TcN-DAUDTC is:
This title complex with [
99mTc ≡ N]
2+Nuclear has a PYR geometric configuration of irregular pros for centronucleus, and wherein the N atom in the Tc ≡ N triple bond is positioned at vertex position, and four sulphur atoms that two DAUDTC ligand moleculars provide are positioned at four points of bottom surface;
And
99mThe TcO-DAUDTC title complex, its structural formula is:
This title complex with [
99mTc (V) O]
3+Be centronucleus, have a PYR geometric configuration of irregular pros, wherein the O atom in the Tc=O key is positioned at vertex position, and four sulphur atoms that two DAUDTC ligand moleculars provide are positioned at four points of bottom surface.
2. one kind prepares according to claim 1
99mThe method of Tc mark daunorubicin dithiocarbamate complexes, its preparation process is as follows:
A. part DAUDTC's is synthetic:
The daunomycin hydrochloride of 0.01mol is added in the reaction vessel, in reaction vessel, add the NaOH methanol solution, slowly drip CS then
2, stirring 2h-3h, the entire reaction course temperature will be controlled at below 10 ℃, and suction filtration gets red solid then, uses recrystallizing methanol, gets red powder and is DAUDTC, and its synthetic route is:
B.
99mThe preparation of TcN-DAUDTC:
With 37～370MBq's
99mTcO
4 -Leacheate 1-5mL joins in the SDH froze-dried kit, fully shakes up, and after solid dissolved fully, 20～30 ℃ of following reactions obtained in 15～30 minutes
99mThe TcN midbody solution is that the ethanolic soln of the part of 1g/L joins above-mentioned with 1mL concentration
99mIn the TcN midbody solution, in boiling water bath, reacted 15 minutes behind the mixing, obtain
99mThe TcN-DAUDTC title complex;
99mLigand exchange reaction is adopted in the preparation of TcN-DAUDTC, and its reaction scheme is as follows:
99mTcO
4 -+SDH+SnCl
2·2H
2O+PDTA→[
99mTcN]
int 2+
[
99mTcN]
int 2++DAUDTC→
99mTcN-DAUDTC
C.
99mThe preparation of TcO-DAUDTC:
With 37～370MBq's
99mTcO
4 -Leacheate 1-5mL joins in the GH froze-dried kit, fully shakes up, and after solid dissolved fully, 20～30 ℃ of following reactions obtained in 15～30 minutes
99mThe TcO-GH midbody solution; With 1mL concentration is that the ethanolic soln of the part of 1g/L joins above-mentioned
99mIn the TcO-GH midbody solution, in boiling water bath, placed 60 minutes behind the mixing, promptly obtain
99mThe TcO-DAUDTC title complex;
99mLigand exchange reaction is adopted in the preparation of TcO-DAUDTC, and its reaction scheme is as follows:
99mTcO
4 -+SnCl
2·2H
2O+GH→
99mTcO-GH
99mTcO-GH+DAUDTC→
99mTcO-DAUDTC。
3. as claimed in claim 1
99mTc mark daunorubicin dithiocarbamate complexes prepares application in the tumor developer at the field of nuclear medicine.
4. as the application in the preparation tumor developer as described in the claim 3, wherein tumor developer is the tumor multi-medicine drug-resistant developer.
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