CN103341185A - Application of radioisotope-labeled meso-position dianthrone compound in preparation of drug for detecting myocardial activity - Google Patents
Application of radioisotope-labeled meso-position dianthrone compound in preparation of drug for detecting myocardial activity Download PDFInfo
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Abstract
The invention relates to the drug field, in particular relates to the application field of a meso-position dianthrone compound, and more specifically relates to application of a radioisotope-labeled meso-position dianthrone compound in preparation of a drug for detecting myocardial activity. The specific bonding force of the radioisotope-labeled meso-position dianthrone compound is utilized to the myocardial necrotic cells, and a radiation source generated by radioisotope is utilized, and a detector is used in a combined manner for achieving the purpose of effectively detecting the myocardial necrotic cells.
Description
Technical field
The present invention relates to drug world, particularly relate to the application of meta dianthrone compounds, more specifically relate to the application of meta dianthrone compounds in the medicine active for the preparation of the detection cardiac muscle of labelled with radioisotope.
Background technology
Myocardial infarction is sickness rate in the cardiovascular disease, the mortality rate disease with high.Cell meeting degeneration necrosis behind the myocardial infarction in the infarcted region forms slough, and is non-renewable.The area of slough is the most important diagnosis index of acute myocardial infarction.The infarcted region of acute myocardial infarction probably exists 40% survival myocardium, may rebuild the back at blood flow and recover or spontaneous recovery myocardial viability.Whether reversible selection to therapeutic scheme has conclusive effect to accurate recognition myocardial infarction patient ischemic myocardium.May existing simultaneously on the heart of myocardial infarction times presses down cardiac muscle, hibernating myocardium and necrotic myocardium, and the above two belong to survival myocardium.If the patient has formed large-area irreversible myocardial infarction survival myocardium seldom, the therapeutic scheme that should select is heart transplantation or symptomatic treatment and should not accept the reconstructive vascular operation treatment.Therefore the accurate diagnosis of myocardial infarction has decisive meaning for cardiopathic treatment.
Mainly contain nuclear magnetic resonance (MRI) for detection of the method for survival myocardium clinically now, positron emission computerized tomography (PET) and single photon emission tomoscan (SPECT), nuclear imaging, by detecting the contractile function of myocardial cell, cell metabolism and myocardial fibrosis are estimated myocardium survival condition.But because all there is limitation in every kind of method, therefore can not judge the state of heart cell exactly, cause the mistake of Therapeutic Method to use delay treatment.
Summary of the invention
The present invention is directed to the limitation of present myocardial cell activity detection method, disclose the application of meta dianthrone compounds in the medicine active for the preparation of the detection cardiac muscle of labelled with radioisotope.
Particularly, the application of the meta dianthrone compounds of labelled with radioisotope in the developing agent active for the preparation of the detection cardiac muscle.
Further say, labelled with radioisotope be meta dianthrone compounds for the preparation of the application in the myocardial infarction developing agent.
Further, described radiosiotope is iodo-123, iodine-125, iodo-124 technetiums-99m, ytterbium-111 or ytterbium-113m.
Especially, described meta dianthrone compounds is any one or a few the mixture among reidin A, reidin B, sorrel dianthrone A or the sorrel dianthrone B.
By research, we find that the meta dianthrone compounds of labelled with radioisotope and the non-viable non-apoptotic cell in the cardiac muscle have very strong affinity, especially, are to have very strong affinity for the myocardial necrosis cell that heart infarction causes.Therefore, we have done a large amount of demonstration tests based on this theory, the meta dianthrone compounds that shows labelled with radioisotope has the specificity adhesion for the myocardial necrosis cell, can accumulate on the necrotic myocardium cell in a large number, utilize radioisotopic labelling, can produce radiographic source, reach the purpose of effective detection myocardial necrosis cell by being used in combination of detector.Because the spatial configuration of different meta dianthrone compounds itself there are differences, and the difference on these configurations can influence the meta dianthrone of meta dianthrone or labelled with radioisotope for the targeting affinity of necrotic myocardium cell.Therefore our preferred chemical compound of reidin A, reidin B, sorrel dianthrone A or these four kinds of structures of sorrel dianthrone B, itself and the non-viable non-apoptotic cell affinity height of cardiac muscle, the targeting height, it is more accurate to detect effect.
Description of drawings
Fig. 1 is that iodine-131 labelling sorrel dianthrone A is at the TTC of Rat of Myocardial Infarction model colored graph;
Fig. 2 is that iodine-131 labelling sorrel dianthrone A is at the autoradiograph of Rat of Myocardial Infarction model;
Fig. 3 is that iodine-131 labelling sorrel dianthrone B is at the TTC of Rat of Myocardial Infarction model colored graph;
Fig. 4 is that iodine-131 labelling sorrel dianthrone B is at the autoradiograph of Rat of Myocardial Infarction model;
Fig. 5 is that iodine-131 labelling reidin A is at the SPECT-CT of Rat of Myocardial Infarction model video picture figure
The specific embodiment
The material of selecting for use in following examples is as follows:
Male SD rat (purchase), reidin A (self-control), reidin B (self-control), sorrel dianthrone A (self-control), sorrel dianthrone B (self-control), activity meter, DMSO analytical pure (rich Dihua, Tianjin worker's company limited), Iodogen reagent (U.S. sigma company), concentrated hydrochloric acid analytical pure (Nanjing Chemistry Reagent Co., Ltd.), Na iodine-131 solution (Beijing Atom High Tech Co., Ltd.), Na iodine-125 solution (Beijing Atom High Tech Co., Ltd.), 2,3,5-triphenyltetrazolium chloride (TTC, Shanghai Ling Jin Fine Chemical Co., Ltd), all the other reagent are analytical pure, RM-905a activity meter (China National Measuring Science Research Inst.'s development), SN-697 gamma counter (Shanghai nuclear institute day ring photoelectric instrument company limited), toy respirator (Shanghai Alcott bio tech ltd), cyclone plus phosphorus screen scanner (Perkin Elmer company).
More than NM material, unless special declaration among the embodiment otherwise is common commercially available prod.
Embodiment 1 Rat of Myocardial Infarction Preparation of model
SD rat body weight 200-300g, the chloral hydrate of lumbar injection 10% (0.3mL/100g).Anesthesia back rat faces upward and is fixed on the Mus platform, and oral trachea cannula connects toy respirator, respiratory frequency 60-80 time/minute, respiratory quotient 1/1, tidal volume 4mL/100g.Behind the povidone iodine skin degerming, open breast along left border of sternum 3,4 intercostals, expose heart, peel off pericardium, at interventricular groove place left auricle parallel beneath threading, ligation ramus descendens anterior arteriae coronariae sinistrae.After the ligation, extract the thoracic cavity air out, recover intrathoracic negative pressure, sew up the thoracic cavity fast, withdraw from tracheal intubation, intramuscular injection penicillin 160,000 U/ only.
The preparation of embodiment 2 iodine-131 labelling sorrel dianthrone A
Take by weighing 13mg sorrel dianthrone A (powder), be dissolved among the 1.0mlDMSO, vibration shakes up, and gets 1.3mg/ml sorrel dianthrone ADMSO solution.The sorrel dianthrone A solution of getting the 1.3mg/ml of 200 μ l adds the DMSO solution of 800 μ l again, and vibration shakes up, and namely gets the sorrel dianthrone A solution of 0.26mg/ml.Be that the sorrel dianthrone ADMSO solution 400 μ l of 0.26mg/ml join that to prepare Iodogen content be being coated with in the pipe of 400 μ g with concentration, the 200 μ Ci Na iodine-131 solution that add 100 μ l, vibration shakes up 45 ℃ of heating in the water-bath, about reaction 90min, after the cessation reaction, measure mark rate with the TLC method, Whatman filter paper is as carrier, and 0.1mol/LHCl launches as mobile phase.
Embodiment 3 distributions of iodine-131 labelling sorrel dianthrone A on the Rat of Myocardial Infarction model
The iodine-131 labelling sorrel dianthrone A solution for preparing among the embodiment 2 is added PEG400, propylene glycol (1: 1) dilution.6 of the flesh infarction of coring rat models, every intravenous injection iodine-131 labelling sorrel dianthrone A solution 100 μ Ci (radiochemical purity is 90%).Behind the 24h, peaceful and comfortable execution rat model, get each internal organs (thyroid, kidney, liver, spleen, lung, normal myocardium, infarcted myocardium, small intestinal, stomach, muscle and fur etc.), weigh respectively and measure radioactivity with gamma counter, behind decay correction, the radioactive uptake that the result is expressed as every gram internal organs or tissue accounts for the percent (%ID/g) of total injected dose.
Behind the iodine-131 labelling sorrel dianthrone A24h, be 1.137%ID/g at necrotic myocardium distribution numerical value, normal myocardium is 0.113%ID/g, and the distribution ratio of necrotic myocardium and normal myocardium is 10.06 times.It is 0.081%ID/g seldom that blood distributes, and does not have the specificity picked-up in the thyroid, and more except the kidney distribution, the distribution in other internal organs is all less.
Table 1
| Tissue or organ | ％ID/g±SD |
| Blood | 0.081±0.013 |
| Lung | 0.041±0.013 |
| Necrotic myocardium | 1.137±0.165 |
| Normal myocardium | 0113±0035 |
| Liver | 0.431±0.062 |
| Stomach | 0.152±0.031 |
| Spleen | 0142±0023 |
| Pancreas | 0091±0042 |
| Small intestinal | 0110±±0.051 |
| Large intestine | 0.090±0021 |
| Kidney | 0820±0131 |
| Bladder | 0160±0.021 |
| Skin | 0.103±0014 |
| Thyroid | 0.101±0.013 |
| Muscle | 0.031±0.007 |
| Necrotic myocardium/normal myocardium | 10.06 |
Embodiment 4 is in the TTC of Rat of Myocardial Infarction model dyeing and iodine-131 labelling sorrel dianthrone A autoradiography contrast
Get isolated heart and make the 2mm slab, under the lucifuge condition with 2% 2,3,5-triphenyltetrazolium chloride (TTC) solution is hatched 15min for 37 ℃.Get the heart section after the dyeing, act on high-resolution sensitization phosphorus screen exposure 1h under 4 ℃ in the darkroom, behind the end exposure with the video picture of phosphorus screen scanner scanning.
Heart shows as brick-red through 2%TTC dyeing back normal myocardium, and necrotic myocardium does not have the painted white that is shown as, position shown in the arrow among Fig. 1.Can observe directly necrotic myocardium zone and the normal myocardium zone of heart.
Adopt the iodine-131 labelling sorrel dianthrone A for preparing among the embodiment 2 to carry out autoradiography, image shows the increased radioactivity of heart zones of different, be the distribution of iodine-131 labelling sorrel dianthrone A on heart, both contrast and find that iodine-131 labelling sorrel dianthrone A can be optionally at the myocardial infarction region clustering, in infarction and normal myocardium intersection distribution is arranged also, and the normal myocardium zone does not distribute almost.
The preparation of embodiment 5 iodine-131 labelling sorrel dianthrone B
Take by weighing 1.3mg sorrel dianthrone B (powder), be dissolved among the 1.0ml DMSO, vibration shakes up, and gets 1.3mg/ml sorrel dianthrone BDMSO solution.The sorrel dianthrone B that gets the 1.3mg/ml of 200 μ l adds the DMSO solution of 800 μ l again, and vibration shakes up, and namely gets the sorrel dianthrone B solution of 0.26mg/ml.Be that the sorrel dianthrone B DMSO solution 400 μ l of 0.26mg/ml join that to prepare Iodogen content be being coated with in the pipe of 400 μ g with concentration, the 200 μ Ci Na iodine-131 solution that add 100 μ l, vibration shakes up 45 ℃ of heating in the water-bath, about reaction 90min, after the cessation reaction, measure mark rate with the TLC method, Whatman filter paper is as carrier, and 0.1mol/LHCl launches as mobile phase.
Embodiment 6 distributions of iodine-131 labelling sorrel dianthrone B on Rat of Myocardial Infarction
The iodine-131 labelling sorrel dianthrone B solution for preparing among the embodiment 5 is added PEG400, propylene glycol (1: 1) dilution.6 of the flesh infarction of coring rat models, every intravenous injection iodine-131 labelling sorrel dianthrone B solution 100 μ Ci (radiochemical purity is 90%).Behind the 24h, peaceful and comfortable execution rat model, get each internal organs (thyroid, kidney, liver, spleen, lung, normal myocardium, infarcted myocardium, small intestinal, stomach, muscle and fur etc.), weigh respectively and measure radioactivity with gamma counter, behind decay correction, the radioactive uptake that the result is expressed as every gram internal organs or tissue accounts for the percent (%ID/g) of total injected dose.
The distribution results of iodine-131 labelling sorrel dianthrone B on Rat of Myocardial Infarction sees Table 2.Behind the iodine-131 labelling sorrel dianthrone B24h, be 1.341%ID/g at necrotic myocardium distribution numerical value, normal myocardium is 0.214%ID/g, and the distribution ratio of necrotic myocardium and normal myocardium is 6.3 times.It is 0.163%ID/g seldom that blood distributes, and does not have the specificity picked-up in the thyroid, and more except the kidney distribution, the distribution in other internal organs is all less.
Table 2
| Tissue or organ | ％ID/g±SD |
| Blood | 0.163±0.031 |
| Lung | 0.090±0.031 |
| Necrotic myocardium | 1.341±0.131 |
| Normal myocardium | 0.214±0.023 |
| Liver | 0.513±0.051 |
| Stomach | 0.193±0.062 |
| Spleen | 0.251±0023 |
| Pancreas | 0.003±0.021 |
| Small intestinal | 0.095±0.031 |
| Large intestine | 0.103±0.037 |
| Kidney | 0.223±0.037 |
| Bladder | 0.161±0.027 |
| Skin | 0.125±0.031 |
| Thyroid | 0.043±0.016 |
| Muscle | 0.037±0.008 |
| Necrotic myocardium/normal myocardium | 6.3 |
Embodiment 7TTC dyeing and iodine-131 labelling sorrel dianthrone B autoradiography
Get isolated heart and make the 2mm slab, under the lucifuge condition with 2% 2,3,5-triphenyltetrazolium chloride (TTC) solution is hatched 15min for 37 ℃.Get the heart section after the dyeing, act on high-resolution sensitization phosphorus screen exposure 1h under 4 ℃ in the darkroom, behind the end exposure with the video picture of phosphorus screen scanner scanning.
Heart shows as brick-red through 2%TTC dyeing back normal myocardium, and necrotic myocardium does not have the painted white that is shown as, and position shown in the arrow among Fig. 1 can observe directly necrotic myocardium zone and the normal myocardium zone of heart.What autoradiographic image showed is the increased radioactivity of zones of different on the heart, be the distribution of iodine-131 labelling sorrel dianthrone B on heart, both contrast and find that iodine-131 labelling sorrel dianthrone B can be optionally at the myocardial infarction region clustering, in infarction and normal myocardium intersection distribution is arranged also, and the normal myocardium zone does not distribute almost.
The preparation of embodiment 8 iodine-131 labelling reidin A
Take by weighing 1.3mg reidin A (powder), be dissolved among the 1.0ml DMSO, vibration shakes up, and gets 1.3mg/ml reidin A DMSO solution.The reidin A solution of getting the 1.3mg/ml of 200 μ l adds the DMSO solution of 800 μ l again, and vibration shakes up, and namely gets the reidin A solution of 0.26mg/ml.Be that the reidin A DMSO solution 400 μ l of 0.26mg/ml join that to prepare Iodogen content be being coated with in the pipe of 400 μ g with concentration, the 200 μ Ci Na iodine-131 solution that add 100 μ l, vibration shakes up 45 ℃ of heating in the water-bath, about reaction 90min, after the cessation reaction, measure mark rate with the TLC method, Whatman filter paper is as carrier, and 0.1mol/L HCl launches as mobile phase.
Embodiment 9 distributions of iodine-131 labelling reidin A on Rat of Myocardial Infarction
The iodine-131 labelling reidin A solution for preparing among the embodiment 8 is added PEG400, propylene glycol (1: 1) dilution.6 of the flesh infarction of coring rat models, every intravenous injection iodine-131 labelling reidin A solution 100 μ Ci (radiochemical purity is 90%).Scan SPECT-CT behind the 24h, the peaceful and comfortable execution rat model in scanning back, get each internal organs (thyroid, kidney, liver, spleen, lung, normal myocardium, infarcted myocardium, small intestinal, stomach, muscle and fur etc.), weigh respectively and measure radioactivity with gamma counter, behind decay correction, the radioactive uptake that the result is expressed as every gram internal organs or tissue accounts for the percent (%ID/g) of total injected dose.
The distribution results of iodine-131 labelling reidin A on Rat of Myocardial Infarction sees Table 3.Behind the iodine-131 labelling reidin A24h, be 2.14%ID/g at necrotic myocardium distribution numerical value, normal myocardium is 0.327%ID/g, and the distribution ratio of necrotic myocardium and normal myocardium is 6.54 times.It is 0.131%ID/g seldom that blood distributes, and does not have the specificity picked-up in the thyroid, and more except the kidney distribution, the distribution in other internal organs is all less.
Table 3
| Tissue or organ | ％ID/g±SD |
| Blood | 0.131±0.021 |
| Lung | 0.103±0.013 |
| Necrotic myocardium | 2.14±0.026 |
| Normal myocardium | 0.327±0.009 |
| Liver | 0.610±0.032 |
| Stomach | 0.125±0.053 |
| Spleen | 0.293±0.056 |
| Pancreas | 0.138±0.061 |
| Small intestinal | 0.137±0.054 |
| Large intestine | 0.128±0.036 |
| Kidney | 0.183±0.062 |
| Bladder | 0.152±0.023 |
| Skin | 0.123±0.020 |
| Thyroid | 0.136±0.024 |
| Muscle | 0.034±0.003 |
| Necrotic myocardium/normal myocardium | 6.54 |
The embodiment 10 video picture results of iodine-131 labelling reidin A on Rat of Myocardial Infarction
Behind the injection iodine-131 labelling reidin A24h, the SPECT-CT video picture of Rat of Myocardial Infarction the results are shown in shown in Figure 5.As seen from Figure 5: 24h after the injection, cardia have tangible radioactivity to concentrate, specifically referring to position shown in the arrow among Fig. 5.In other major organs and soft tissue, do not see obviously and concentrate, illustrate that its removing speed in vivo is very fast, embody distribution and pharmacokinetic property in the good body of iodine-131 labelling reidin A diagnostic medicine.
The preparation of embodiment 11 iodine-125 labelling reidin B
Take by weighing 1.3mg reidin B (powder), be dissolved among the 1.0ml DMSO, vibration shakes up, and gets 1.3mg/ml reidin B DMSO solution.The reidin B solution of getting the 1.3mg/ml of 200 μ l adds the DMSO solution of 800 μ l again, and vibration shakes up, and namely gets the reidin B solution of 0.26mg/ml.Be that the reidin B DMSO solution 400 μ l of 0.26mg/ml join that to prepare Iodogen content be being coated with in the pipe of 400 μ g with concentration, the 200 μ Ci Na iodine-125 solution that add 100 μ l, vibration shakes up 45 ℃ of heating in the water-bath, about reaction 90min, after the cessation reaction, measure mark rate with the TLC method, Whatman filter paper is as carrier, and 0.1mol/L HCl launches as mobile phase.
Embodiment 12 distributions of iodine-125 labelling reidin B on Rat of Myocardial Infarction
The iodine-125 labelling reidin B solution for preparing among the embodiment 11 is added PEG400, propylene glycol (1: 1) dilution.6 of the flesh infarction of coring rat models, every intravenous injection iodine-125 labelling reidin B solution 100 μ Ci (radiochemical purity is 90%).Behind the 24h, peaceful and comfortable execution rat model, get each internal organs (thyroid, kidney, liver, spleen, lung, normal myocardium, infarcted myocardium, small intestinal, stomach, muscle and fur etc.), weigh respectively and measure radioactivity with gamma counter, behind decay correction, the radioactive uptake that the result is expressed as every gram internal organs or tissue accounts for the percent (%ID/g) of total injected dose.
The distribution results of iodine-125 labelling reidin B on Rat of Myocardial Infarction sees Table 4.Behind the iodine-125 labelling reidin B24h, be 1.642%ID/g at necrotic myocardium distribution numerical value, normal myocardium is 0.187%ID/g, and the distribution ratio of necrotic myocardium and normal myocardium is 8.78 times.It is 0.131%ID/g seldom that blood distributes, and does not have the specificity picked-up in the thyroid, and more except the kidney distribution, the distribution in other internal organs is all less.
Table 4
| Tissue or organ | ％ID/g±SD |
| Blood | 0.131±0.021 |
| Lung | 0.103±0.013 |
| Necrotic myocardium | 1.642±0.058 |
| Normal myocardium | 0.187±0.043 |
| Liver | 0.610±0.032 |
| Stomach | 0.125±0.053 |
| Spleen | 0.293±0.056 |
| Pancreas | 0.138±0.061 |
| Small intestinal | 0.137±0.054 |
| Large intestine | 0.128±0.036 |
| Kidney | 0.183±0.062 |
| Bladder | 0.152±0.023 |
| Skin | 0.123±0.020 |
| Thyroid | 0.136±0.024 |
| Muscle | 0.034±0.003 |
| Necrotic myocardium/normal myocardium | 8.78 |
According to the mode among the embodiment 1 to 12, respectively the meta dianthrone compounds of technetium-99m, ytterbium-111, ytterbium-113m, iodine-125 and iodine 124 labellings is carried out targeting and assembles experiment, find its have with embodiment in essentially identical targeting.Therefore, equally can be for the preparation of the medicine for detection of the cardiac muscle activity.
Claims (5)
1. the application of the meta dianthrone compounds of labelled with radioisotope in the medicine active for the preparation of the detection cardiac muscle.
2. application according to claim 1 is characterized in that: the application of the meta dianthrone compounds of labelled with radioisotope in the developing agent active for the preparation of the detection cardiac muscle.
3. application according to claim 2 is characterized in that: the meta dianthrone compounds of labelled with radioisotope is for the preparation of the application in the myocardial infarction developing agent.
4. according in claim 1 or 2 or the application described in 3, it is characterized in that: described radiosiotope is iodo-123, iodo-124, iodine-125, iodine-131, technetium-99m, ytterbium-111 or ytterbium-113m.
5. according to any described application in claim 1 or 2 or 3, it is characterized in that described meta dianthrone is any one or a few the mixture among reidin A, reidin B, sorrel dianthrone A or the sorrel dianthrone B.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104491889A (en) * | 2014-12-05 | 2015-04-08 | 江苏省中医药研究院 | Application of radiolabelled monoanthracene nucleus anthraquinone compound in preparation of medicine used for detecting myocardial viability |
| CN108743981A (en) * | 2018-06-22 | 2018-11-06 | 中国药科大学 | Application of the serotonin and 5HTP of labelled with radioisotope in necrotic myocardium imaging |
-
2013
- 2013-07-23 CN CN2013103087765A patent/CN103341185A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| 王俊虎等: "131Ｉ标记番泻苷Ａ在正常小鼠体内分布和评价心肌活性研究", 《同位素》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104491889A (en) * | 2014-12-05 | 2015-04-08 | 江苏省中医药研究院 | Application of radiolabelled monoanthracene nucleus anthraquinone compound in preparation of medicine used for detecting myocardial viability |
| CN104491889B (en) * | 2014-12-05 | 2017-05-24 | 江苏省中医药研究院 | Application of radiolabelled monoanthracene nucleus anthraquinone compound in preparation of medicine used for detecting myocardial viability |
| CN108743981A (en) * | 2018-06-22 | 2018-11-06 | 中国药科大学 | Application of the serotonin and 5HTP of labelled with radioisotope in necrotic myocardium imaging |
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