CN106806908A - A kind of glucose metabolism imageable agents box - Google Patents
A kind of glucose metabolism imageable agents box Download PDFInfo
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- CN106806908A CN106806908A CN201510859356.5A CN201510859356A CN106806908A CN 106806908 A CN106806908 A CN 106806908A CN 201510859356 A CN201510859356 A CN 201510859356A CN 106806908 A CN106806908 A CN 106806908A
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Abstract
The invention discloses a kind of glucose metabolism imageable agents box, including A group reagents, B group reagents and C agent;The A group reagents are made of following raw materials:2,3,4,6- tetra--O- acetyl -1- (1 '-nitrine acetamide)-β-D-Glucose 5.0-50.0 weight portions, urea 20-200 weight portions;The B group reagents are made of following raw materials:The mercaptan 0.5-5.0 weight portions of dibenzo cyclooctyne-monoamine monoamide two, glucoheptose 0.5-5.0 weight portions, stannous chloride dihydrate 0.001-0.2 weight portions, urea 20-200 weight portions;The C reagents are:99mTcO4 -Solution, radioactive activity is 3.7 × 107Bq-3.7×109Bq.Test result indicate that, the kit has as the potentiality of glucose metabolism developer.
Description
Technical field
Radiopharmaceuticals product technique field the invention belongs to contain radioactive substance, images more particularly to a kind of glucose metabolism and tries
Agent box.
Background technology
18F-FDG is the most pet imaging agent of current clinical practice, has been largely used to:1st, the diagnosis of the nervous system disease:It is insane
Epilepsy, brain tumor, dementia and Parkinson's etc.:2nd, myocardial ischemia is detected, myocardial viability is determined:3rd, the diagnosis of tumour, by stages,
Curative effect monitoring and Index for diagnosis;4th, brain function research [Basu S.et al.Ann.NY.Acad.Sci.2011.1228 (1) .1-18;
Almuhaideb A.et al.Ann.Saudi.Med.2011.31(1).3-13;Vallabhajosula S.et al.Semin.Nucl.Med.
2011.41(4).246-264].The abnormality proliferation of malignant cell needs excessive use [the Warburg O.Science. of glucose
1956.123 (3191) .309-314.], the vigorous position of glucose metabolism that is to say potential tumor focus.Therefore, glucose generation
The clinical meaning for thanking to imaging is great.
18The clinical practice of F-FDG needs to be equipped with very expensive Positron emission computed tomography instrument (PET-CT) and medical
Accelerator, only large hospital carries out Clinical practice at home, and diagnosis is costly, and18Half-life period shorter (the T of F1/2=109.7min),
Still cannot be popularized and be promoted in clinic.
Radionuclide99mTc has good nulcear properties, half-life period T1/2It is 6h, emitted energy is the gamma-rays of 140keV, non-
Often suitable SPECT imagings, it is cheap and be easily obtained by molybdenum PertechnetateSodium Iniection, it is preferably to be used for disease and tumour
The radionuclide of diagnostic imaging, at home hospital's nuclear medicine widely use.Domestic and international research institution's nearly more than ten years concentrate research and
New convenient, the cheap and imaging results of preparation of exploitation are good99mTc- glucose metabolism imageable agents boxes.
Reporting with99mThe direct labelled glucose derivatives of Tc such as 5-Thioglucose [Ozker K.et al.Nucl.Med.
Commun.1999.20.1055-1058. the internal behavior] with glucose is different, it is impossible to be transported albumen identification;Then carry out
With containing N2S2Part [Yang D J.et al.Radiology.2003.226.465-473.] or matching somebody with somebody with diethyl pentetic acid
After the coupling of body [Chen Y.et al.Appl.Radiat.Isot.2006.64.342-347.] and glucose molecule and99mWhat Tc was marked
Compound cannot quickly be discharged cell by intracellular hexokinase phosphorylation;Bayly et al. [Bayly S R.et al.
Bioconjugate.Chem.2004.15.923-926.] using Tc (CO)3A sugar derivatives containing phenolic group and secondary amine is marked,
But the complexes stability is bad;Ferreira et al. [Ferreira C L.et al.Bioconjugate.Chem.2006.17.
1321-1329] five kinds of bidentate ligands are prepared for, and carried out Tc (CO)3Marker research, it is found that stability is enhanced,
But these complexs can not suppress hexokinase, can not be phosphorylated;Schibli et al. [Dumas C.et al.Bioconjugate.
Chem.2005.16.421-428;Dumas C.et al.J.Org.Chem.2003.68.512-518;Schibli R.et al.
Bioconjugate.Chem.2005.16.105-112] investigate some tridentate ligands and Tc (CO)3The complex of formation, these are matched somebody with somebody
Compound is unrelated with Glut-1 glucose transporters;[the Mikata Y.et al.Inorg.Chem.2004.43.4778-4780. such as Mikata
Storr T.et al.Inorg.Chem.2005.44.2698-2705;Storr T.et al.Dalton Trans.2005.654-655.] prepare
Sugar derivatives part include two pyridine amine and a tertiary amine, can preferably with Tc (CO)3The complex of stabilization is formed, but
These complexs can neither be by cellular uptake, can not be by hexokinase phosphorylation.These99mTc labelled glucose metabolic imaging agent
All it is bulky complex, this bulky radionuclide and organic ligand have a significant impact to glucose group,
It is also the main cause for causing its biological assessment effect on driving birds is not good.
[3+2] cycloaddition reaction without copper click chemistry, i.e. cyclooctyne Yu nitrine, occur soon, without side reaction with reaction speed etc.
Advantage [Sletten E.M.et al.Accounts.Chem.Res.2011.44.666-676;Science,2008,320,664-667].
But not yet have to utilize at present and be applied to without copper click chemistry99mThe report of the glucose metabolism developer of Tc marks.
The content of the invention
The purpose of the present invention is to overcome the deficiencies in the prior art, there is provided a kind of glucose metabolism imaging examination for being obviously improved imaging quality
Agent box.
Technical scheme is summarized as follows:
A kind of glucose metabolism imageable agents box, including A group reagents, B group reagents and C agent;
The A group reagents are made of following raw materials:2,3,4,6- tetra--O- acetyl -1- (1 '-nitrine acetamide)-β-D-Glucose
[N3- DG-2, is shown in structure formula (I)] 5.0-50.0 weight portions, urea 20-200 weight portions;
The B group reagents are made of following raw materials:[ADIBO-MAMA is shown in knot to dibenzo cyclooctyne-mercaptan of monoamine monoamide two
Structure formula (II)] 0.5-5.0 weight portions, glucoheptose 0.5-5.0 weight portions, stannous chloride dihydrate 0.001-0.2 weight portions, urea
20-200 weight portions;
The C reagents are:99mTcO4 -Solution, radioactive activity is 3.7 × 107Bq-3.7×109Bq。
Preferably:A group reagents are made of following raw materials:2,3,4,6- tetra--O- acetyl -1- (1 '-nitrine acetamide)-β-D-Glucose 30.0
Weight portion, the weight portion of urea 20;
Preferably:B group reagents are made of following raw materials:Dibenzo cyclooctyne-weight portion of two mercaptan of monoamine monoamide 1.0, glucoheptose
2.0 weight portions, the weight portion of stannous chloride dihydrate 0.005, the weight portion of urea 20.
A group reagents are made of following methods:By 2,3,4,6- tetra--O- acetyl -1- (1 '-nitrine acetamide)-β-D-Glucose 5.0-50.0
Weight portion, urea 20-200 weight portions are dissolved in 1000-10000 weight portion water;It is above-mentioned molten with 0.22 micron of aseptic filtration membrane filtration
Liquid, is dispensed into cillin bottle with 1.0-2.0mL/ bottles;Freeze-drying 24-48 hours, nitrogen is filled with, gland takes out.
B group reagents are made of following methods:
(1) by the mercaptan 0.5-5.0 weight portions of dibenzo cyclooctyne-monoamine monoamide two, glucoheptose 0.5-5.0 weight portions, urea
20-200 weight portions are dissolved in 100-1000 weight portion water, obtain solution one;
(2) by stannous chloride dihydrate 0.001-0.2 weight portions, it is dissolved in 100-1000 weight portion 0.01-1.0M HCl/water solution
In solution two;
(3) solution two is added in solution one, is mixed, adjust pH=5-7, added water to 1000-10000 weight portions and obtain solution
Three;By solution three with 0.22 micron of aseptic filtration membrane filtration, it is dispensed into cillin bottle with 1.0-2.0mL/ bottles, freeze-drying 24-48
Hour, nitrogen is filled with, gland takes out.
C reagents are made of following methods:It is 3.7 × 10 by radioactive activity7Bq-3.7×109Bq99mTcO4 -Leacheate, uses aseptic life
Reason salt solution is diluted to 3-5mL.
Advantages of the present invention:
Test result indicate that, glucose metabolism imageable agents box of the invention has tumor/blood ratio and tumour/muscle ratio higher,
With more the potentiality as glucose metabolism developer.
Brief description of the drawings
Fig. 1 be in test example 1 radioactivity-high performance liquid chromatograph determine gained chromatogram (ordinate is radioactive activity in figure,
Unit:cpm;Abscissa is time, unit:min).
Specific embodiment
With reference to specific embodiment, the present invention is further illustrated.
Embodiment 1
A kind of glucose metabolism imageable agents box, including A group reagents, B group reagents and C reagents;
The A group reagents are made of following raw materials:2,3,4,6- tetra--O- acetyl -1- (1 '-nitrine acetamide) weight of-β-D-Glucose 30.0
Amount part, the weight portion of urea 20.0;
The B group reagents are made of following raw materials:Dibenzo cyclooctyne-weight portion of two mercaptan of monoamine monoamide 1.0, glucoheptose 2.0
Weight portion, the weight portion of urea 20, the weight portion of stannous chloride dihydrate 0.005;
The C reagents are:99mTcO4 -Solution, radioactive activity is 3.7 × 108Bq。
Embodiment 2
A kind of glucose metabolism imageable agents box, including A group reagents, B group reagents and C reagents;
The A group reagents are made of following raw materials:2,3,4,6- tetra--O- acetyl -1- (1 '-nitrine acetamide) weight of-β-D-Glucose 5.0
Amount part, the weight portion of urea 20;
The B group reagents are made of following raw materials:Dibenzo cyclooctyne-weight portion of two mercaptan of monoamine monoamide 0.5, glucoheptose 0.5
Weight portion, the weight portion of urea 20, the weight portion of stannous chloride dihydrate 0.001;
The C reagents are:99mTcO4 -Solution, radioactive activity is 3.7 × 107Bq。
Embodiment 3
A kind of glucose metabolism imageable agents box, including A group reagents, B group reagents and C reagents;
The A group reagents are made of following raw materials:2,3,4,6- tetra--O- acetyl -1- (1 '-nitrine acetamide) weight of-β-D-Glucose 50.0
Amount part, the weight portion of urea 200;
The B group reagents are made of following raw materials:Dibenzo cyclooctyne-weight portion of two mercaptan of monoamine monoamide 5.0, glucoheptose 5.0
Weight portion, the weight portion of urea 200, the weight portion of stannous chloride dihydrate 0.2;
The C reagents are:99mTcO4 -Solution, radioactive activity is 3.7 × 109Bq。
Embodiment 4
A kind of glucose metabolism imageable agents box, including A group reagents, B group reagents and C reagents;
A group reagents are made of following methods:By 2,3,4,6- tetra--O- acetyl -1- (1 '-nitrine acetamide) weight of-β-D-Glucose 30.0
Part, the weight portion of urea 20 is dissolved in 5000 weight portion water;With 0.22 micron of aseptic filtration membrane filtration, west is dispensed into 1.5mL/ bottles
In woods bottle;Freeze-drying 36 hours, is filled with nitrogen, and gland takes out.
B group reagents are made of following methods:
(1) by dibenzo cyclooctyne-weight portion of two mercaptan of monoamine monoamide 1.0, the weight portion of glucoheptose 2.0, the weight portion of urea 20
It is dissolved in 500 weight portion water, obtains solution one;
(2) by the weight portion of stannous chloride dihydrate 0.005, it is dissolved in 500 weight portion 0.1M HCl/water solution obtaining solution two;
(3) solution two is added in solution one, is mixed, adjust pH=6, added water to 5000 weight portions and obtain solution three;Will be molten
Liquid three is dispensed into cillin bottle with 0.22 micron of aseptic filtration membrane filtration with 1.5mL/ bottles, freeze-drying 36 hours, is filled with nitrogen,
Gland takes out.
C reagents are made of following methods:The 3.7 × 10 of quality standard will be met8Bq99mTcO4 -Leacheate, will with SPSS
It is diluted to 4mL.
Embodiment 5
A kind of glucose metabolism imageable agents box, including A group reagents, B group reagents and C reagents;
A group reagents are made of following methods:By 2,3,4,6- tetra--O- acetyl -1- (1 '-nitrine acetamide) weight of-β-D-Glucose 5.0
Part, the weight portion of urea 20 is dissolved in 1000 weight portion water;With 0.22 micron of aseptic filtration membrane filtration, west is dispensed into 1.0mL/ bottles
In woods bottle;Freeze-drying 24 hours, is filled with nitrogen, and gland takes out.
B group reagents are made of following methods:
(1) by dibenzo cyclooctyne-weight portion of two mercaptan of monoamine monoamide 0.5, the weight portion of glucoheptose 0.5, the weight of urea 20
Part is dissolved in 100 weight portion water, obtains solution one;
(2) by the weight portion of stannous chloride dihydrate 0.001, it is dissolved in 100 weight portion 0.01M HCl/water solution obtaining solution two;
(3) solution two is added in solution one, is mixed, adjust pH=7, added water to 1000 weight portions and obtain solution three;Will be molten
Liquid three is dispensed into cillin bottle with 0.22 micron of aseptic filtration membrane filtration with 1.0mL/ bottles, freeze-drying 24 hours, is filled with nitrogen,
Gland takes out.
C reagents are made of following methods:By 3.7 × 109Bq99mTcO4 -Leacheate, 3mL is diluted to SPSS.
Embodiment 6
A kind of glucose metabolism imageable agents box, including A group reagents, B group reagents and C reagents;
A group reagents are made of following methods:By 2,3,4,6- tetra--O- acetyl -1- nitrine-β-weight portion of D-Glucose 50.0, urea 200
Weight portion is dissolved in 10000 weight portion water;With 0.22 micron of aseptic filtration membrane filtration, it is dispensed into cillin bottle with 2.0mL/ bottles;It is cold
It is lyophilized dry 48 hours, nitrogen is filled with, gland takes out.
B group reagents are made of following methods:
(1) by dibenzo cyclooctyne-weight portion of two mercaptan of monoamine monoamide 5.0, the weight portion of glucoheptose 5.0, the weight portion of urea 200
It is dissolved in 1000 weight portion water, obtains solution one;
(2) by the weight portion of stannous chloride dihydrate 0.2, it is dissolved in 1000 weight portion 1.0M HCl/water solution obtaining solution two;
(3) solution two is added in solution one, is mixed, adjust pH=5, added water to 10000 weight portions and obtain solution three;Will be molten
Liquid three is dispensed into cillin bottle with 0.22 micron of aseptic filtration membrane filtration with 2.0mL/ bottles, freeze-drying 48 hours, is filled with nitrogen,
Gland takes out.
C reagents are made of following methods:By 3.7 × 109Bq99mTcO4 -Leacheate, 5mL is diluted to SPSS.
Test example 1
This test example is that the dibenzo ring in B group reagents is marked with C reagents in radioactivity-high performance liquid chromatograph measure embodiment 5
Tc-99m mark dibenzo cyclooctyne-mercaptan of monoamine monoamide two obtained by the mercaptan of octyne-monoamine monoamide two
(99mTc-ADIBO-MAMA mark rate).Its computing formula is as follows:
Condition determination:Radioactivity-high performance liquid chromatograph analysis use Agilent HC-C18 posts (5 μm of 4.6 × 150mm, size),
2487 dual wavelength ultraviolets of Waters-visible spectrophotometer (Waters 600E series) and radiometer amount detector (Packard 500TR
Series) system is completed.A solvents are mutually 0.1M ammonium acetate aqueous solutions, and B solvents are mutually acetonitrile.Drip washing gradient is:0-2min 90%
A;2-5min 90%-30%A;5-35min 30%-0A;35-37min 0-90%A, flow velocity is 1.0mL/min.
Measuring method:
The C reagent sample introductions of 3-4MBq are taken with microsyringe, is analyzed according to said determination condition, in acquisition HPLC Fig. 1
(a);
3-4MBq is taken with microsyringe99mTc-GH solution, is analyzed according to said determination condition, obtains99mTc-GH's
(b) in HPLC Fig. 1;
99mThe preparation of Tc-GH Solutions Solutions:
(1) weight portion of glucoheptose 0.5 is dissolved in 100 weight portion water, obtains the ' of solution one;
(2) by the weight portion of stannous chloride dihydrate 0.001, it is dissolved in 100 weight portion 0.01M HCl/water solution obtaining the ' of solution two;
(3) ' of solution two is added in the ' of solution one, is mixed, adjust pH=7, added water to 1000 weight portions and obtain the ' of solution three;
By solution three with 0.22 micron of aseptic filtration membrane filtration, filtrate is obtained;
(4) gained filtrate is added in C reagents in taking 1mL (3), after vibration, static 10min.
1-2MBq is taken with microsyringe99mTc-ADIBO-MAMA solution, is analyzed according to said determination condition, obtains
The HPLC of label, (c) seen in Fig. 1.
99mThe preparation of Tc-ADIBO-MAMA Solutions Solutions:C reagents are added in one bottle of B group reagent, vibration is mixed, 100 DEG C
Heating response 5min in water-bath.
As can be seen from Figure 1:99mTcO4 -Retention time be 3.3min,99mThe retention time of Tc-GH is 1.9min, and is marked
Product99mTc-ADIBO-MAMA retention times are 7.7min, it is possible to achieve separated well;It is not found raw material from (c)99mTcO4 -And intermediate product99mThe chromatographic peak of Tc-GH, illustrates that reaction is complete, and mark rate is close to 100%.
Test example 2
First (contain N to A group reagents in lotus S180 mice with tumor internal injections embodiment 53- DG-2), then by C reagents mark in embodiment 5
Note B group reagents obtain Tc-99m marks dibenzo cyclooctyne-mercaptan of monoamine monoamide two (99mTc-ADIBO-MAMA lotus) is injected
In S180 mice with tumor bodies, the two bio distribution in lotus S180 mice with tumor bodies is determined.
S180 sarcoma model can be by the way that in male mouse of kunming, (prosperity experimental animal cultivates factory, 20-22 for Haidian District, Beijing City
G) the fresh S180 cell liquid (bio tech ltd of Nanjing section one hundred of left front leg oxter hypodermic injection;Cell line:CCRF S-180
II, mouse muscle;Concentration is 107~108/ mL) set up;After 7~10 days, tumour grows to diameter about 10~15mm, can be used for reality
Test.
40 good tumor-bearing mices of neoplastic conditions are selected, experimental group 20 is divided into four groups, 1h, 2h, 4h and 8 are corresponded to respectively
H groups, every group 5, control group 20 is divided into four groups, and 1h, 2h, 4h and 8h group, every group 5 are corresponded to respectively.Experimental group is small
Mouse more than fasting 16h before experiment, tail vein injection 0.1mL A group reagents (contain N within 2 hours in advance3- DG-2) solution (uses
When dissolve 1 bottle of A group reagent with 5mL medical salines), then tail vein injection 0.1mL 5 × 104Bq99m(3mL reagent Cs dissolve 1 bottle of B group reagent to the marked product of Tc-ADIBO-MAMA, and vibration is mixed, under the conditions of 100 DEG C
Heating response 5min);Control group, more than experiment mice fasting 16h, tail vein injection 0.1mL 5 × 10 before experiment4Bq99m(3mL reagent Cs dissolve 1 bottle of B group reagent to the marked product of Tc-ADIBO-MAMA, and vibration is mixed, under the conditions of 100 DEG C
Heating response 5min);
Different time points after injection take correspondence group mouse its eye socket is taken into blood, then break neck put to death, take out brain, muscle,
Bone, tumour, the heart, stomach, intestines, kidney, spleen, lung, liver, are rinsed well with water, exclude content and wipe it is dry after weigh, use
Automatic gamma counter surveys its radioactive intensity respectively, and (%ID/g is averaged with result in group to calculate the intake of each organ
Value, is represented with mean+SD), while calculating the knurl blood ratio and knurl meat ratio of Each point in time, experimental result is shown in Table 1.
The control group of table 1 and bio distribution of the experimental group in lotus S180 mice with tumor bodies,
During experiment using control group as control (being represented with mean+SD)
From the data of table 1:The liver intake of experimental group is higher, because fat-soluble big compound is mainly metabolized by liver and gall;
The heart, lung, stomach and muscle are removed beginning with a small amount of intake quickly, then almost without intake in brain;Experimental group is over time
Extension, knurl blood than with knurl meat than the trend being gradually increasing is presented.Compared with control group, experimental group is substantially few by intake in liver
A lot, and removing of the experimental group in liver is faster than control group;Experimental group is clear in the organs such as the heart, stomach, spleen, lung, kidney
Except being significantly faster than that control group;The tumor/blood and tumour/muscle ratio of experimental group are bigger than control group.
The imaging results of glucose metabolism imageable agents box are preferable as can be seen here, with the potentiality as glucose metabolism developer.
It is demonstrated experimentally that embodiment 4, the testing result of embodiment 6 are similar to Example 5.
Claims (6)
1. a kind of glucose metabolism imageable agents box, it is characterised in that including A group reagents, B group reagents and C agent;
The A group reagents are made of following raw materials:2,3,4,6- tetra--O- acetyl -1- (1 '-nitrine acetamide)-β-D-Glucose 5.0-50.0 weight portions, urea 20-200 weight portions;
The B group reagents are made of following raw materials:The mercaptan 0.5-5.0 weight portions of dibenzo cyclooctyne-monoamine monoamide two, glucoheptose 0.5-5.0 weight portions, stannous chloride dihydrate 0.001-0.2 weight portions, urea 20-200 weight portions;
The C reagents are:99mTcO4 -Solution, radioactive activity is 3.7 × 107Bq-3.7×109Bq。
2. a kind of glucose metabolism imageable agents box according to claim 1, it is characterized in that the A group reagents are made of following raw materials:2,3,4,6- tetra--O- acetyl -1- (1 '-nitrine acetamide) weight portion of-β-D-Glucose 30.0, the weight portion of urea 20.
3. a kind of glucose metabolism imageable agents box according to claim 1, it is characterized in that the B group reagents are made of following raw materials:Dibenzo cyclooctyne-the weight portion of two mercaptan of monoamine monoamide 1.0, the weight portion of glucoheptose 2.0, the weight portion of stannous chloride dihydrate 0.005, the weight portion of urea 20.
4. a kind of glucose metabolism imageable agents box according to claim 1, it is characterized in that the A group reagents are made of following methods:By 2,3,4,6- tetra--O- acetyl -1- (1 '-nitrine acetamide)-β-D-Glucose 5.0-50.0 weight portions, urea 20-200 weight portions are dissolved in 1000-10000 weight portion water;With 0.22 micron of above-mentioned solution of aseptic filtration membrane filtration, it is dispensed into cillin bottle with 1.0-2.0mL/ bottles;Freeze-drying 24-48 hours, nitrogen is filled with, gland takes out.
5. a kind of glucose metabolism imageable agents box according to claim 1, it is characterized in that the B group reagents are made of following methods:
(1) by the mercaptan 0.5-5.0 weight portions of dibenzo cyclooctyne-monoamine monoamide two, glucoheptose 0.5-5.0 weight portions, urea 20-200 weight portions are dissolved in 100-1000 weight portion water, obtain solution one;
(2) by stannous chloride dihydrate 0.001-0.2 weight portions, it is dissolved in 100-1000 weight portion 0.01-1.0M HCl/water solution obtaining solution two;
(3) solution two is added in solution one, is mixed, adjust pH=5-7, added water to 1000-10000 weight portions and obtain solution three;By solution three with 0.22 micron of aseptic filtration membrane filtration, it is dispensed into cillin bottle with 1.0-2.0mL/ bottles, freeze-drying 24-48 hours, is filled with nitrogen, gland takes out.
6. a kind of glucose metabolism imageable agents box according to claim 1, it is characterized in that the C reagents are made of following methods:It is 3.7 × 10 by radioactive activity7Bq-3.7×109Bq 99mTcO4 -Leacheate, 3-5mL is diluted to SPSS.
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