CN102977174A - 99mTc(CO)3 nuclear-labeled macrocyclic polyamine triazole ring glucose-based complex as well as preparation and application of complex - Google Patents
99mTc(CO)3 nuclear-labeled macrocyclic polyamine triazole ring glucose-based complex as well as preparation and application of complex Download PDFInfo
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Abstract
The invention discloses a 99mTc(CO)3 nuclear-labeled macrocyclic polyamine triazole ring type glucose-based complex as well as a preparation and an application of the complex. The complex is 99mTc(CO)3-[12]N3-G for short and is formed by taking a 99mTc(CO)3 nuclear as a centronucleus and using three nitrogen atoms in a [12]N3-G ligand molecule to replace 3 H2O molecules on a (99mTc(CO)3(H2O)3)+ intermediate. The complex is prepared by two process steps, namely the synthesis of [12] N3-G and the preparation of a 99mTc(CO)3-[12]N3-G complex. The complex disclosed by the invention has the advantages of high radiochemical purity, good stability, high tumor intake, good tumor/muscle ratio and the like, and is a novel tumor imaging agent with excellent performances.
Description
Technical field
The present invention relates to
99mTc (CO)
3Radiopharmaceutical chemistry and the clinical nuclear medicine technical field of nuclear mark relate to a kind of specifically
99mTc (CO)
3Macrocyclic polyamine triazole lopps glucosyl group title complex and the preparation method and application of nuclear mark.
Background technology
The malignant cell metabolism is vigorous, and the demand of glucose far above normal cell, is expressed a large amount of glucose transporter on the tumor cell membrane.D-Glucose analogue structure and D-Glucose are similar, also can be transported by glucose transporter, by the vigorous tumour cell picked-up of metabolism.Its by radioisotope labeling after, carry out external detection by PET, SPECT, be used for diagnosing tumor, by stages, treatment and therapeutic evaluation.
18The F-fluorodeoxyglucose ([
18F] FDG) be the most widely tumor developer of present clinical application, enjoy the good reputation of " battle steed ".Because [
18F] FDG is a kind of pet imaging agent, positron radionuclide [
18F] need to produce by accelerator, expensive, hindered to a certain extent its widespread use in clinical diagnosis, especially in countries and regions underdeveloped.In view of the foregoing, be necessary to develop a kind of easy and cheap novel tumor developer for preparing.
99mTc is as the medical science tracer agent, compares with other nucleic to have very large superiority: suitable transformation period (T
1/2=6.02h), the moderate single photon γ of energy (E γ=140kev) emission, decay daughter radiation dose are low etc., and
99Mo-
99mThe Tc producer succeed in developing so that
99mBut the simple medicine box of Tc radiopharmaceuticals preparation, cheap and easy to get, reliable in quality.Therefore, research
99mTc labelled glucose class tumor developer also is a general orientation and the focus of current radiopharmaceuticals development.
Up to now,
99mTc-ethylenedicysteine-deoxyglucose (is called for short
99mTc-ECDG) be uniquely to enter the clinical study stage
99mTc labelled glucose class tumor developer, but there is the shortcomings such as tumor uptake value and tumour/blood is on the low side, therefore desirable
99mThe glucose tumour metabolize imaging agent of Tc mark still remains to be explored.The technetium carbonyl compound has that volume is little, kinetic inertness and the good advantages such as vitro stability, and three carbonyls (CO) part of this class complex compound has very high stability, and the easy replaced or mark of covalency water molecules.Especially in recent years successfully preparation under normal pressure [
99mTc (CO
3(H
2O
3]
+Method make a breakthrough, make the research of technetium carbonyl-complexes also become one of the study hotspot in radiopharmaceutical chemistry field.The research of Macrocyclic polyamine and metal complexes thereof plays a part more and more important in synthetic chemistry, life science.The title complex of some metal of Macrocyclic polyamine shows good stability under physiological condition, therefore at aspects such as nuclear magnetic resonance diagnosis (human body visualization), x X-ray diagnosis X, ultrasonic diagnosis, radiodiagnosis and radiation treatments potential application prospect is arranged.Especially Isosorbide-5-Nitrae, the 7-7-triazacyclononane (is called for short: [9] N
3) and 1,5,9-triazododecane (abbreviation: [12] N
3) etc. macrocyclic polyamine compound as the less tridentate ligand of volume can with [
99mTc (CO)
3(H
2O)
3]
+The caryogamy position generates good stability
99mTc (CO)
3-[9] N
3With
99mTc (CO)
3-[12] N
3Title complex.The present invention in conjunction with the study hotspot of modern chemistry and
99mThe Click chemistry is used in the new development of Tc marking method, is nitrine sugar with conversion of glucose, with the triazole lopps glycosyl part that contains the generation of the efficient fast selective of Macrocyclic polyamine alkine compounds ground and contain Macrocyclic polyamine (referred to as [12] N
3-G), then utilize in the Macrocyclic polyamine nitrogen-atoms with
99mTc (CO)
3The caryogamy position forms stable
99mTc (CO)
3The Seleroglucar analogue is sought the novel tumor developer, has very important scientific research and application and development and is worth.
Summary of the invention
Purpose of the present invention provides that a kind of radiochemical purity is high, good stability, is applied in the tumor imaging field
99mTc (CO)
3Nuclear mark Macrocyclic polyamine triazole lopps glucosyl group title complex also provides its preparation method simultaneously.
In order to narrate conveniently, hereinafter will
99mTc (CO)
3Nuclear mark Macrocyclic polyamine triazole lopps glucosyl group title complex referred to as:
99mTc (CO)
3-[12] N
3-G.
In order to achieve the above object, the present invention by the following technical solutions: a kind of
99mTc (CO)
3-[12] N
3-G title complex, its structural formula is:
In this structural formula: with
99mTc (CO)
3Examine [12] N centered by the nuclear
33 nitrogen-atoms replacements the in-G ligand molecular [
99mTc (CO)
3(H
2O)
3]
+3 H on the intermediate
2Generate behind the O molecule
99mTc (CO)
3-[12] N
3-G title complex.
99mTc (CO)
3-[12] N
3The preparation method of-G title complex is as follows:
A: part [12] N
3-G's is synthetic:
Take by weighing an amount of 1-nitrine-1-deoxidation-β-D-glucopyranoside, Boc-[12] aneN
3In two mouthfuls of flasks of 50mL, add the tetrahydrofuran (THF) dissolving, add again a small amount of aqueous solution that is dissolved with cupric sulfate pentahydrate, add at last sodium ascorbate, stir, reaction is spent the night under the argon shield condition; Rotary evaporation obtains faint yellow solid, adds a small amount of water dissolution, uses ethyl acetate extraction 3 times, collects ethyl acetate layer, and concentrated, column chromatography method carries out purifying and obtains Aoc-G-Boc-[12] N3; At Aoc-G-Boc-[12] add an amount of anhydrous methanol among the N3, then add a small amount of sodium methylate, room temperature reaction 6h, concentrated, add a small amount of water, concentrated, add again a small amount of ethanol, suction filtration, concentrated filtrate, vacuum-drying gets white solid, adds salt acid for adjusting pH value 3-4 in product, boiling water bath heating 1h, regulate pH7-8 with the methanol solution of NaOH again, the adularescent solid produces, and filters, concentrated filtrate, 45 ℃ of dried overnight of vacuum obtain brown color solid [12] N
3-G;
Synthetic route:
B:
99mTc (CO)
3-[12] N
3The preparation of-G title complex:
In the penicillin bottle, add 5mg Na
2CO
3, 10mg NaBH
4, the 15mg Seignette salt, add shake up dissolving under the physiological saline room temperature after, passed into CO gas 15 minutes, add Na
99mTcO
4Fresh leacheate, shake up rear 75-80 ℃ of lower reaction namely obtained in 30 minutes [
99mTc (CO)
3(H
2O)
3]
+Intermediate; Take by weighing 2mg[12] N
3-G part, add above-mentioned [
99mTc (CO)
3(H
2O)
3]
+In the intermediate, regulator solution pH value is 8-9, and boiling water bath heating 30 minutes namely obtains of the present invention
99mTc (CO)
3-[12] N
3-G title complex.
Prepare by aforesaid method
99mTc (CO)
3-[12] N
3-G title complex vitro stability at room temperature is good, and its radiochemical purity is greater than 90%.
Will
99mTc (CO)
3-[12] N
3-G with
99mTc-ECDG and [
18F] FDG bio distribution data (David J.et al.Imaging with in the tumor-bearing mice body
99mTc-ECDG Targeted at the Multifunctional Glucose Transport System:Feasibility Study with Rodents[J] .Radiology, 2003,226 (2): 465-473) relatively, the results are shown in Table 1.
Table 1
99mTc (CO)
3-[12] N
3-G,
99mTc-ECDG, [
18F] FDG bio distribution data comparisons (%ID/g, n=3) in the tumor-bearing mice body behind injection 2h
Can find out from the result of above contrast,
99mTc (CO)
3-[12] N
3Tumor uptake value and the tumour/muscle ratio of-G all are higher than
99mTc-ECDG and [
18F] FDG, can be used as a kind of novel tumor developer.
Experiment detects and shows,
99mTc (CO)
3-[12] N
3The performance of-G title complex is as follows:
1.
99mTc (CO)
3-[12] N
3The high performance liquid chromatography of-G (HPLC) is identified
High pressure liquid chromatography (HPLC) is identified: Shimadzu SCL-10AVP type high pressure liquid chromatograph, (25cm * 4.6mm), Packard liquid dodges analyser to Kromasil 100-5C18 reversed-phase column.Drip washing condition of gradient elution (A is the water that contains 0.1% TFA, and B is the acetonitrile that contains 0.1% TFA) sees Table 2, and flow velocity is 1.0ml/min, and the retention time of each component of mensuration (Rt) is respectively: [
99mTc (CO)
3(H
2O)
3]
+: 18.1min;
99mTc (CO)
3-[12] N
3-G:4.2min, the chromatogram result of gained show that (t=4.2min has single radioactivity main peak) shows generation
99mTc (CO)
3-[12] N
3The radiochemical purity of-G title complex is greater than 90%.
The condition of gradient elution of table 2 title complex
2.
99mTc (CO)
3-[12] N
3The mensuration of the lipid of-G title complex
Get the phosphate buffered saline buffer (0.025mol/L) of 0.99mLpH7.4 in the 10mL centrifuge tube, in centrifuge tube, add 1.0mL n-Octanol and 0.01mL
99mTc (CO)
3-[12] N
3-G solution covers stopper, vortex, centrifugal 5min (5000r/min).Then take out 0.1mL from organic phase and aqueous phase respectively, measure the radiocounting of two-phase, and calculate its partition ratio P (radioactive activity of the radioactive activity/water of P=organic phase), record log P=-1.22 ± 0.01, explanation
99mTc (CO)
3-[12] N
3-G is a kind of water-soluble substances.
3.
99mTc (CO)
3-[12] N
3The Stability Determination of-G title complex
Mark is good
99mTc (CO)
3-[12] N
3-G title complex is at room temperature placed and is measured its radiochemical purity after 6 hours, and experimental result shows
99mTc (CO)
3-[12] N
3-G title complex after placing 6 hours radiochemical purity greater than 90%, explanation
99mTc (CO)
3-[12] N
3-G title complex at room temperature vitro stability is good, is suitable for the needs of clinical application.
4.
99mTc (CO)
3-[12] N
3The bio distribution experiment of-G title complex in the mice with tumor model
Tail vein injection 0.10mL from the kunming mice (female, the about 18-20g of body weight) of lotus S-180 sarcoma model
99mTc (CO)
3-[12] N
3-G complex solution (about 7.4 * 10
5Bq), after the injection respectively with 0.5h, 2h, 4h sacrificed by decapitation.Get related organization and the organs such as its heart, liver, lung, kidney, spleen, bone, intestines, muscle, blood, tumour, weigh after cleaning, and survey its radiocounting with the technetium analyser, each the time phase the tumor-bearing mice number be 3.Calculate every gram percentage injected dose (%ID/g) of each tissue.The results are shown in Table 3.
Table 3
99mTc (CO)
3-[12] N
3The bio distribution (x ± s, n=3, %ID/g) of-G title complex in the mice with tumor model
The body embodiment:
Below by embodiment in detail the present invention is described in detail: a kind of
99mTc (CO)
3-[12] N
3-G title complex, its structural formula is:
In this structural formula: with
99mTc (CO)
3Examine [12] N centered by the nuclear
33 nitrogen-atoms replacements the in-G ligand molecular [
99mTc (CO)
3(H
2O)
3]
+3 H on the intermediate
2Generate behind the O molecule
99mTc (CO)
3-[12] N
3-G title complex.
99mTc (CO)
3-[12] N
3The preparation method of-G title complex is as follows:
(1) part [12] N
3-G's is synthetic
The first step:
Take by weighing 1-nitrine-1-deoxidation-β-D-glucopyranoside 186.66mg, Boc-[12] aneN
3204.5mg in two mouthfuls of flasks of 50mL, add the dissolving of 10mL tetrahydrofuran (THF), add again a small amount of aqueous solution that is dissolved with the 12.484mg cupric sulfate pentahydrate, add at last the sodium ascorbate of 39.6mg, stir, reaction is spent the night under the argon shield condition.Rotary evaporation obtains faint yellow solid, adds a small amount of water dissolution, uses ethyl acetate extraction 3 times, collects ethyl acetate layer, and concentrated, column chromatography method carries out purifying and obtains 353.0mg Aoc-G-Boc-[12] N3.
1HNMR(500MHz，CDCl3)：δ(ppm)7.62(s，1H)，5.88-5.86(q，1H)，5.46-5.40(m，2H)，5.28-5.23(m，1H)，4.35-4.30(q，1H)，4.14-4.17(d，1H)，4.03-3.99(m，1H)，3.79(s，2H)，3.35-3.33(d，8H)，2.43-2.42(d，4H)，2.09-2.07(d，6H)，2.03(s，3H)，1.86(s，9H)，1.45(s，18H).
13CNMR(500MHz，CDCl3)：δ(ppm)170.46，169.85，169.36，168.77(C＝O-OCH
3)，156.30(C＝O-O(CH
3)
3)，144.48(C-N＝N)，120.60，120.57(C-N-N)，85.80，75.18，72.60，70.28，67.79，61.56(glucose)，79.24(C(CH
3)
3)，49.72，45.46，43.73，27.05，26.23([12]N3)，46.55(CH
2-[12]N3)，28.51(CH
3-C-O-C＝O-[12]N3)，20.52，20.48，20.11，20.08(CH
3-O-C＝O-glucose).HRMS(ESI)：C
18H
35N
6O
5(MH
+)，783.4140.
Second step:
Take by weighing 40mg Aoc-G-Boc-[12] N3, add the 20mL anhydrous methanol, add a small amount of sodium methylate, room temperature reaction 6h, concentrated, add a small amount of water, concentrated, add again a small amount of ethanol, suction filtration, concentrated filtrate, vacuum-drying gets white solid 25mg, adds salt acid for adjusting pH value 3-4 in product, boiling water bath heating 1h, regulate pH7-8 with the methanol solution of NaOH again, the adularescent solid produces, and filters, concentrated filtrate, 45 ℃ of dried overnight of vacuum obtain 12mg brown color solid [12] N
3-G.
1HNMR(500MHz，CDCl3)：δ(ppm)8.79(s，1H)，6.22-6.20(d，1H)，4.38-4.33(t，1H)，4.25-4.21(d，1H)，4.-5-4.10(m，4H)，4.02-3.97(t，1H)，3.73-3.68(d，10H)，3.65(s，2H)，2.63-2.49(d，8H).
13CNMR(500MHz，CDCl3)：δ(ppm)139.40(C-N＝N)，130.33(C-N-N)，90.46，90.26，，81.7578.57，78.39，75.06，71.89，63.49(glucose)，51.86(CH
2-[12]N3)，50.34，45.00，44.13，23.11，20.81([12]N3).HRMS(ESI)：C
18H
35N
6O
5(MH
+)，415.2669.
(2)
99mTc (CO)
3-[12] N
3The preparation of-G title complex
In the penicillin bottle, add 5mg Na
2CO
3, 10mg NaBH
4, the 15mg Seignette salt, add shake up dissolving under the physiological saline room temperature after, passed into CO gas 15 minutes, add Na
99mTcO
4Fresh leacheate, shake up rear 75-80 ℃ of lower reaction namely obtained in 30 minutes [
99mTc (CO)
3(H
2O)
3]
+Intermediate.Take by weighing 2mg[12] N
3-G part, add above-mentioned [
99mTc (CO)
3(H
2O)
3]
+In the intermediate, regulator solution pH value is 8-9, and boiling water bath heating 30 minutes namely obtains of the present invention
99mTc (CO)
3-[12] N
3-G title complex.
By the detection digital proof to above embodiment
99mTc (CO)
3-[12] N
3-G title complex can be used as a kind of novel tumor developer and applies.
Claims (3)
1. one kind
99mTc (CO)
3-[12] N
3-G title complex is characterized in that: its representative structure formula is as follows:
In structural formula: with
99mTc (CO)
3Examine [12] N centered by the nuclear
33 nitrogen-atoms replacements the in-G ligand molecular [
99mTc (CO)
3(H
2O)
3]
+3 H on the intermediate
2Generate behind the O molecule
99mTc (CO)
3-[12] N
3-G title complex.
2. preparation as claimed in claim 1
99mTc (CO)
3-[12] N
3The preparation method of-G title complex, its processing step is as follows:
A: part [12] N
3-G's is synthetic:
Take by weighing an amount of 1-nitrine-1-deoxidation-β-D-glucopyranoside, Boc-[12] aneN
3In two mouthfuls of flasks of 50mL, add the tetrahydrofuran (THF) dissolving, add again a small amount of aqueous solution that is dissolved with cupric sulfate pentahydrate, add at last sodium ascorbate, stir, reaction is spent the night under the argon shield condition; Rotary evaporation obtains faint yellow solid, adds a small amount of water dissolution, uses ethyl acetate extraction 3 times, collects ethyl acetate layer, and concentrated, column chromatography method carries out purifying and obtains Aoc-G-Boc-[12] N3; At Aoc-G-Boc-[12] add an amount of anhydrous methanol among the N3, then add a small amount of sodium methylate, room temperature reaction 6h, concentrated, add a small amount of water, concentrated, add again a small amount of ethanol, suction filtration, concentrated filtrate, vacuum-drying gets white solid, adds salt acid for adjusting pH value 3-4 in product, boiling water bath heating 1h, regulate pH7-8 with the methanol solution of NaOH again, the adularescent solid produces, and filters, concentrated filtrate, 45 ℃ of dried overnight of vacuum obtain brown color solid [12] N
3-G;
B:
99mTc (CO)
3-[12] N
3The preparation of-G title complex:
In the penicillin bottle, add 5mg Na
2CO
3, 10mg NaBH
4, the 15mg Seignette salt, add again shake up dissolving under the physiological saline room temperature after, passed into CO gas 15 minutes, add Na
99mTcO
4Fresh leacheate, shake up rear 75-80 ℃ of lower reaction namely obtained in 30 minutes [
99mTc (CO)
3(H
2O)
3]
+Intermediate; Take by weighing 2mg[12] N
3-G part, add above-mentioned [
99mTc (CO)
3(H
2O)
3]
+In the intermediate, regulator solution pH value is 8-9, and boiling water bath heating 30 minutes namely obtains of the present invention
99mTc (CO)
3-[12] N
3-G title complex.
3. as claimed in claim 1
99mTc (CO)
3-[12] N
3-G title complex prepares the purposes in the tumor developer in the radiopharmaceutical chemistry field.
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| CN105524113A (en) * | 2016-03-04 | 2016-04-27 | 北京师范大学 | 99mTcN nucleus-marked glucose dithiocarbamate complex containing triazole ring and preparation method and application of glucose dithiocarbamate complex |
| CN105541799A (en) * | 2015-12-10 | 2016-05-04 | 北京师范大学 | [12] aneN3 cationic lipid containing targeted group and fluorescent group, transgenic vector, and preparation methods of cationic lipid and transgenic vector |
| CN106806908A (en) * | 2015-11-30 | 2017-06-09 | 天津朋德药业有限公司 | A kind of glucose metabolism imageable agents box |
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| Publication number | Publication date |
|---|---|
| CN102977174B (en) | 2015-04-22 |
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