CN102070747A - Polymer for fluorescein angiogram and isotope angiogram - Google Patents

Polymer for fluorescein angiogram and isotope angiogram Download PDF

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CN102070747A
CN102070747A CN 201010602881 CN201010602881A CN102070747A CN 102070747 A CN102070747 A CN 102070747A CN 201010602881 CN201010602881 CN 201010602881 CN 201010602881 A CN201010602881 A CN 201010602881A CN 102070747 A CN102070747 A CN 102070747A
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polymer
hydrogen
rhodamine
angiogram
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路建美
戚裕
李娜君
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Suzhou University
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Abstract

The invention belongs to the field of polymer synthesis, and particularly relates to a polymer for fluorescein angiogram and isotope angiogram and a synthesis method of the polymer. The synthesis method mainly comprises the following steps: (1) reacting a hydroxyl-containing olefine acid ester substance with rhodamine, which contains a carboxyl group at the 3<-> position and is subjected to acyl chlorination to form a monomer containing a rhodamine group; (2) reacting tyrosine ester hydrochloride after deacidification with acrylic anhydride to obtain a monomer containing a tyrosine group; and (3) copolymerizing the two monomers and the hydroxyl-containing olefine acid ester substance to obtain a polymer contrast agent precursor. The polymer has strong red fluorescence of rhodamine substances and can lab radioisotopes; and the polymer can rapidly enter living cells, and can be enriched in not only cytoplasm but also in vivo tumour tissues.

Description

A kind of polymer that can be used for fluoroscopic visualization and isotropic substance radiography
Technical field
The invention belongs to the Polymer Synthesizing field, be specifically related to a kind of polymer and synthetic method that can be used for fluoroscopic visualization and isotropic substance radiography.
Background technology
Some biological medical polymer materials such as polyoxyethylene glycol (PEG), polyacrylic acid (PAA), polymine (PEI), daiamid (PAMAM) etc. have caused concern widely in lesion detection and treatment field.The polymer of these synthetic easily obtains some important performances, turns usefulness into as strengthening infiltration and stick effect (EPR effect) and film instability.Wherein, the EPR effect makes polymer and entrained material thereof can reach most of tumor locus target.The film instability turns into then making polymer pass some plasma membranes easily, reaches to escape out endosome before the lysosome and enter tenuigenin in cell, avoids being degraded or decomposing.And in practical study and in using, these macromolecular materials need be traceable.
A kind of method commonly used is that fluorescence dye is connected with polymer, and the cell or tissue that this polymer is entered can be launched stronger fluorescent signal.Detection method based on fluorescence imaging has advantages such as susceptibility height, the contrast medium consumption is few, radiation quantity is little, and the focus that therefore becomes research in recent years also begins in clinical application.As two-dimentional fluorescence dioptric imaging technology (Two-dimensional fluorescence reflectance imaging, FRI) and the Fluobeam system and the FLARE system that develop based on this image-forming principle be applied to preclinical diagnosis.But the angiographic method that is based on fluoroscopic examination is used fashion and is had defective in live body, especially detects some and darker will face problems when light is had the internal organs of certain absorption such as lung, spleen and liver.
On the other hand, having obtained deep research and application based on the diagnosing tumor and the treatment means of radio isotope signal detection, is a kind of technology of comparative maturity, more is close to practical application at present.Seeking suitable part or group, to carry out isotopic labeling be a committed step.The tyrosine group can be used to mark 18F, 123I, 125I, 131I etc. are to be used for positron emission tomography art (PET), SPECT (single photon emission computed tomography) (SPECT), the automatic ray imaging of high resolving power.These halogens are generally better with the compound stability after tyrosine combines by covalent linkage.And tyrosine has excellent biological compatibility as a seed amino acid.Therefore, tyrosine is incorporated into can be on the basis that keeps high molecular functional in the polymer, and the many-side that is implemented in radioactive rays detection and treatment field is used; Different with fluorescent contrast agent, radio-labeling is after buying raw material (as chloramine-T etc.) by market, own when needed synthesizing.Synthetic good radiocontrast medium can not be sold in market.
Summary of the invention
The object of the invention provides a kind of polymer that not only can be used for fluoroscopic visualization but also can be used for the isotropic substance radiography.
For achieving the above object, basic ideas of the present invention are:
Figure 2010106028816100002DEST_PATH_IMAGE002
With after the carboxylic rhodamine chloride in 3-position and the olefin(e) acid Ester reaction that contains hydroxyl form the monomer that contains the rhodamine group;
Figure 2010106028816100002DEST_PATH_IMAGE004
To react the monomer that obtains containing the tyrosine group with acrylic anhydride after the depickling of tyrosine ester hydrochloride;
Figure 2010106028816100002DEST_PATH_IMAGE006
Again by the synthetic polymeric contrast agent precursor that obtains of above-mentioned two kinds of monomers and the olefin(e) acid Ester copolymerization that contains hydroxyl.
The concrete technical scheme of the present invention is synthetic a kind of polymer that can be used for fluoroscopic visualization and isotropic substance radiography, and its structural formula is as follows:
Figure 2010106028816100002DEST_PATH_IMAGE008
，
In the formula, R 1, R 2, R 3, R 4Be selected from a kind of in hydrogen, the replacement that does not contain reactive hydrogen or unsubstituted alkyl or the aryl separately; R 5, R 6, R 7, R 8Be selected from a kind of in hydrogen, alkoxyl group, halogen, amino, the replacement that does not contain reactive hydrogen or unsubstituted alkyl or the aryl separately; R 9, R 10, R 11, R 13Be selected from a kind of in hydrogen, the replacement that does not contain active H or the unsubstituted alkyl separately; R 12Be selected from a kind of in the replacement that do not contain reactive hydrogen or the unsubstituted alkyl;
N, x, y, z are natural number, wherein 1≤n≤3,1≤x≤5,1≤y≤10,200≤z≤400; An -Be arbitrarily negatively charged ion stable in the aqueous solution, be selected from a kind of among chlorion, bromide anion, sulfate radical or the perchlorate.
In the optimized technical scheme, in the above-mentioned high molecular structural formula that can be used for fluoroscopic visualization and isotropic substance radiography, R 1, R 2, R 3, R 4Be selected from hydrogen, C separately 1～C 3Alkyl or aryl in a kind of; R 5, R 6, R 7, R 8Be selected from hydrogen, C separately 1～C 3Alkyl, aryl, halogen or amino in a kind of; R 9, R 10, R 11, R 13Be selected from hydrogen, C separately 1～C 3Alkyl in a kind of; R 12Be selected from C 1～C 3Alkyl in a kind of.
In the most preferred technical scheme, in the above-mentioned high molecular structural formula that can be used for fluoroscopic visualization and isotropic substance radiography, R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10And R 11Be hydrogen; R 12And R 13Be methyl; An -Be chlorion.
The above-mentioned high molecular preparation method who can be used for fluoroscopic visualization and isotropic substance radiography may further comprise the steps:
⑴ have the rhodamine chloride of carboxyl with the 3-bit strip, promptly obtains the thick product of rhodamine acyl chlorides; Add organic solvent A, stir and make the dissolving of rhodamine acyl chlorides fully, at room temperature slowly add the olefin(e) acid Ester that contains hydroxyl, solution stirring is more than 15 hours, obtain containing the rhodamine group monomer (
Figure 2010106028816100002DEST_PATH_IMAGE010
), its structural formula is as follows:
Figure 2010106028816100002DEST_PATH_IMAGE012
；
Described organic solvent A is selected from a kind of in acetonitrile or the methylene dichloride; The olefin(e) acid Ester of described hydroxyl is a Hydroxyethyl acrylate; Described 3-bit strip has the rhodamine of carboxyl to be selected from but is not limited to rhodamine B;
⑵ with the hydrochloride depickling of tyrosine ester, and promptly obtains tyrosine ester with dichloromethane extraction; Tyrosine ester is dissolved in the methylene dichloride, reacts more than 20 hours with acrylic anhydride at 0 ℃ of ice bath with under stirring; Obtain after the purification containing the tyrosine group monomer (
Figure 900143DEST_PATH_IMAGE010
I), its structural formula is as follows:
Figure 2010106028816100002DEST_PATH_IMAGE014
；
The hydrochloride of described tyrosine ester is selected from but is not limited to the tyrosine ethyl ester hydrochloride;
With step ⑴ gained monomer (
Figure 941917DEST_PATH_IMAGE010
), the olefin(e) acid Ester and the Diisopropyl azodicarboxylate of step ⑵ gained monomer (II), hydroxyl be dissolved in the organic solvent B, under rare gas element C protection,, can be used for the polymer of fluoroscopic visualization and isotropic substance radiography through precipitating, dry acquisition in 60～70 ℃ of isothermal reactions 10～14 hours;
Described organic solvent B is selected from pimelinketone or N, a kind of in the dinethylformamide; Described rare gas element C is selected from a kind of in nitrogen, helium, neon, argon gas or the krypton gas.
Because the technique scheme utilization, the present invention compared with prior art has following advantage:
1. synthetic polymer of the present invention can enter viable cell rapidly, enrichment in tenuigenin, and the also interior enrichment of tumor tissues in vivo.
2. synthetic polymer of the present invention has the intensive red fluorescence of rhodamine class material, and its red fluorescence can significantly reduce the interference of background fluorescence, and fluorescence intensity is stable, and fast light bleaching is higher.Use this fluorescence polymer to obtain fluorescence imaging figure clearly by shootings such as fluorescent microscope, Laser Scanning Confocal Microscopes.
3. contain the tyrosine group in the synthetic polymer of the present invention, can be used for mark 18F, 123I, 125I, 131Radio isotope such as I; After isotopic labeling, this polymer can be used for the isotropic substance radiography.
4. the complete synthetic of synthetic polymer of the present invention, do not contain any biological characteristic group, its easier modification, its physical and chemical performance more easy to control, and cost is generally lower, by further connect other functional groups on macromolecular chain, this polymer also can be considered as a kind of bio-carrier that can integrate multiple function and be applied to biology, each field of medicine and pharmacology.
Description of drawings
Fig. 1 is a synthetic described high molecular process synoptic diagram among the embodiment one;
Fig. 2 is the fluorescence excitation spectrum of the polymer PRTH1 aqueous solution among the embodiment two;
Fig. 3 is the fluorescence emission spectrum of the polymer PRTH1 aqueous solution among the embodiment two;
Fig. 4 be among the embodiment three polymer PRTH1 to the fluorescent microscopic imaging figure of human liver cancer cell (7402).Wherein, A figure is the natural light image, and B figure is fluorescence imaging figure;
Fig. 5 is a polymer PRTH1 process radio isotope among the embodiment three 125Behind the I mark, by SPECT (single photon emission computed tomography) (SPECT) at the intravital image of HepA liver cancer model nude mice.
Embodiment
Below in conjunction with drawings and Examples the present invention is further described.
Embodiment one: with reference to the accompanying drawing 1 synthetic polymer that can be used for fluoroscopic visualization and isotropic substance radiography, concrete steps are as follows:
Figure 637883DEST_PATH_IMAGE002
Contain the synthetic of rhodamine B group monomer:
(2.1mmol) is dissolved in 1 with the 1g rhodamine B, in the 2-ethylene dichloride, at room temperature slowly splashes into thionyl chloride 0.9ml.Reaction system is stirred and refluxed 6 hours, removal of solvent under reduced pressure after reaction is finished promptly obtains the thick product of rhodamine B acyl chlorides.Add methylene dichloride, stir and make the dissolving of rhodamine B acyl chlorides fully.At room temperature slowly splash into Hydroxyethyl acrylate 1.0ml (9.6mmol), solution stirring 24 hours.React the back removal of solvent under reduced pressure that finishes, obtain containing the monomer crude product of rhodamine B group.With silica gel column chromatography separate contain the rhodamine B group the monomer straight product (
Figure 501934DEST_PATH_IMAGE010
), this monomer is a green powder, its structure is as follows:
Figure 2010106028816100002DEST_PATH_IMAGE016
Nuclear magnetic resonance measuring: 1H NMR (CDCl 3): δ 8.32 (d, 1H), 7.85 (t, 1H), 7.76 (T, 1H), 7.33 (d, 1H), 7.07 (d, 2H), 6.94 (d, 2H), 6.81 (s, 2H), 6.36 (m, 1H), 6.05 (m, 1H). 5.88 (m, 1H), 4.30 (m, 2H), 4.18 (m, 2H), 3.66 (m, 8H), 1.34 (t, 12H); From the magnetic resonance detection structure as can be known, the gained compound is the purpose compound.
Figure 378623DEST_PATH_IMAGE004
Contain the synthetic of tyrosine group monomer:
With 5g NaHCO 3(2.1mmol) be dissolved in the 75ml water, slowly add methylene dichloride 50mL.Add L-tyrosine ethyl ester hydrochloride 2.8g (2.1mmol) in batches, slowly stirred 4 hours.Behind the separatory,, obtain crude product, obtain the tyrosine ethyl ester faint yellow solid with a small amount of ether washing with the methylene dichloride evaporate to dryness.1.5g tyrosine ethyl ester (2.1mmol) and 0.8g triethylamine (2.1mmol) are dissolved in the 40ml methylene dichloride, under 0 ℃ of ice bath and stirring, slowly splash into the dichloromethane solution 40ml of 1.2g acrylic anhydride, reacted 24 hours.Use the NaHCO of 0.06 g/ml respectively 3The NaH of solution and 0.06 g/ml 2PO 4The solution washing reaction solution, the methylene dichloride phase is collected in extraction.The pressure reducing and steaming methylene dichloride obtains oily liquids.With after the tetrahydrofuran (THF) dissolving, splash in the big water gaging, separate out the monomer straight product that contains the tyrosine group (
Figure 794561DEST_PATH_IMAGE010
I), this monomer is a weak yellow liquid.Its structure is as follows:
Figure 2010106028816100002DEST_PATH_IMAGE018
；
Nuclear magnetic resonance measuring: (CDCl 3): δ 9.24 (m, 1H), 8.19 (d, 1H), 7.02 (m, 1H), 6.64 (m, 1H), 5.63 (m, 1H), 5.35 (m, 1H), 4.36 (dd, 1H), 4.05 (m, 1H), 2.90 (m, 1H), 1.79 (m, 1H), 1.12 (t, 1H)); From the magnetic resonance detection structure as can be known, the gained compound is the purpose compound.
Figure 123911DEST_PATH_IMAGE006
With 1.73g contain the rhodamine B group monomer (
Figure 791653DEST_PATH_IMAGE010
) (3mmol), 1.39g contains the monomer (I of tyrosine group
Figure 555472DEST_PATH_IMAGE010
) (5mmol), 11.6g Hydroxyethyl acrylate (100mmol), 164mg Diisopropyl azodicarboxylate (1mmol) be dissolved in the pimelinketone.Under nitrogen protection in 60 ℃ of isothermal reactions 12 hours.With the solution cooling, splash in the methylene dichloride after having reacted, separate out polymer.This macromolecule dissolution in ethanol, is repeated precipitating 3 times again.Promptly obtain containing the polymer PRTH1 of rhodamine B group and tyrosine group at last through vacuum-drying.
⑷ according to step
Figure 17677DEST_PATH_IMAGE006
Method prepare PRTH2 and PRTH3, wherein for PRTH2 and PRTH3, the charging capacity of Diisopropyl azodicarboxylate is respectively 328mg and 820mg.
For PRTH1, PRTH2 and PRTH3, measure number-average molecular weight through GPC and be respectively 25100,38800,31300.Measure through uv analysis method: x, y, z mean value are respectively 1,2,213 among the PRTH1; X, y, z mean value are respectively 2,6,326 among the PRTH2; X, y, z mean value are respectively 1,4,265 among the PRTH3.Its structural formula is as follows:
Figure DEST_PATH_IMAGE020
。
Embodiment two
Figure 834324DEST_PATH_IMAGE002
The fluorescence excitation spectrum of the 0.25mg/ml aqueous solution of the polymer PRTH1 of drafting embodiment one gained, X-coordinate is wavelength (nm), ordinate zou is a fluorescence intensity, gets Fig. 2;
This high molecular maximum excitation peak position is similar with rhodamine B as we know from the figure, between 550-570nm.
Figure 164811DEST_PATH_IMAGE004
The fluorescence emission spectrum of the 0.25mg/ml aqueous solution of the polymer PRTH1 of drafting embodiment one gained gets Fig. 3, and X-coordinate is wavelength (nm), and ordinate zou is a fluorescence intensity.
This high molecular fluorescent emission peak position is also similar with rhodamine B as we know from the figure, between 580-600nm.
Embodiment three
Utilize the polymer PRTH1 that can be used for fluoroscopic visualization and isotropic substance radiography of embodiment one gained that human liver cancer cell (7402) is carried out fluorescent microscopic imaging, the fluorescence behind bright field photo and the polymer mark of the present invention according to (Fig. 4).7402 cells are taken fluorescence photo after incubation time is 30 minutes in containing the RPMI-1640 nutrient solution of fluorescence polymer, and culture temperature is 25 ℃;
The result shows: occur red fluorescence in the cell, its fluorescence intensity is significantly higher than background.As seen, polymer PRTH can enter cell more significantly and be enriched in the tenuigenin, forms fluoroscopic image comparatively clearly.
Embodiment four
The polymer PRTH1 mark that can be used for fluoroscopic visualization and isotropic substance radiography with embodiment one gained 125With the physiological saline wiring solution-forming, be injected in the HepA liver cancer model nude mice tail vein behind the I, the image by SPECT obtains different time gets Fig. 5.
The result shows: as time passes, strengthen gradually in time at the tumor region radiated signal, the signal in the common internal organs then weakens gradually.The signal intensity rate I of the strength of signal of its common internal organs and tumor region A/ I BFrom 2.0 to 0.5 variation tendency can illustrate that PRTH1 can be accumulated in the tumor tissues significantly by certain hour, makes tumor tissues become the strongest position of body radioactivity signal.Therefore, PRTH1 has the target to the HepA tumor tissues, and can be used in the SPECT imaging.

Claims (3)

1. a polymer that can be used for fluoroscopic visualization and isotropic substance radiography is characterized in that, the described high molecular structural formula that can be used for fluoroscopic visualization and isotropic substance radiography is as follows:
Figure 2010106028816100001DEST_PATH_IMAGE002
，
In the formula, R 1, R 2, R 3, R 4Be selected from a kind of in hydrogen, the replacement that does not contain reactive hydrogen or unsubstituted alkyl or the aryl separately; R 5, R 6, R 7, R 8Be selected from a kind of in hydrogen, alkoxyl group, halogen, amino, the replacement that does not contain reactive hydrogen or unsubstituted alkyl or the aryl separately; R 9, R 10, R 11, R 13Be selected from a kind of in hydrogen, the replacement that does not contain active H or the unsubstituted alkyl separately; R 12Be selected from a kind of in the replacement that do not contain reactive hydrogen or the unsubstituted alkyl;
N, x, y, z are natural number, wherein 1≤n≤3,1≤x≤5,1≤y≤10,200≤z≤400; An -Be arbitrarily negatively charged ion stable in the aqueous solution, be selected from a kind of among chlorion, bromide anion, sulfate radical or the perchlorate.
2. polymer according to claim 1 is characterized in that R 1, R 2, R 3, R 4Be selected from hydrogen, C separately 1～C 3Alkyl or aryl in a kind of; R 5, R 6, R 7, R 8Be selected from hydrogen, C separately 1～C 3Alkyl, aryl, halogen or amino in a kind of; R 9, R 10, R 11, R 13Be selected from hydrogen, C separately 1～C 3Alkyl in a kind of; R 12Be selected from C 1～C 3Alkyl in a kind of.
3. polymer according to claim 1 is characterized in that R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10And R 11Be hydrogen; R 12And R 13Be methyl; An -Be chlorion.
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102942918A (en) * 2012-11-08 2013-02-27 中国科学院化学研究所 Polybetaine fluorescent labeling agent and preparation method thereof
CN104511030A (en) * 2013-09-29 2015-04-15 复旦大学 Dual-modal nano imaging drug Dex-Rho-99mTc based on glucan
CN104817662A (en) * 2015-04-09 2015-08-05 清华大学 Iodine and fluoramino phosphate-containing high-molecular contrast agent capable of simultaneously using for CT and NMR imaging, preparation method and application thereof
CN107118198A (en) * 2017-06-08 2017-09-01 福州大学 Have rhodamine B derivative of antitumaous effect and fluorescence property and preparation method thereof concurrently
WO2018159028A1 (en) * 2017-03-01 2018-09-07 株式会社エーピーアイ コーポレーション N-benzyl-2-bromo-3-methoxypropionamide and method for producing intermediate thereof

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Publication number Priority date Publication date Assignee Title
CN101418215A (en) * 2008-12-15 2009-04-29 苏州大学 High molecule fluorescent detecting probe containing rhodamine gene and synthetic method

Patent Citations (1)

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Publication number Priority date Publication date Assignee Title
CN101418215A (en) * 2008-12-15 2009-04-29 苏州大学 High molecule fluorescent detecting probe containing rhodamine gene and synthetic method

Non-Patent Citations (1)

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Title
《Reactive & Functional Polymers》 20101221 Yu Qi，et al A cancer-targetable copolymer containing tyrosine segments for labeling radioactive halogens 390-394 1-3 第71卷, 2 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102942918A (en) * 2012-11-08 2013-02-27 中国科学院化学研究所 Polybetaine fluorescent labeling agent and preparation method thereof
CN104511030A (en) * 2013-09-29 2015-04-15 复旦大学 Dual-modal nano imaging drug Dex-Rho-99mTc based on glucan
CN104817662A (en) * 2015-04-09 2015-08-05 清华大学 Iodine and fluoramino phosphate-containing high-molecular contrast agent capable of simultaneously using for CT and NMR imaging, preparation method and application thereof
CN104817662B (en) * 2015-04-09 2017-07-14 清华大学 Simultaneously for CT and NMR imaging containing iodine, fluorine-containing phosphoramidate family macromolecule contrast agent and preparation method and application
WO2018159028A1 (en) * 2017-03-01 2018-09-07 株式会社エーピーアイ コーポレーション N-benzyl-2-bromo-3-methoxypropionamide and method for producing intermediate thereof
US11136287B2 (en) 2017-03-01 2021-10-05 Api Corporation Method for producing n-benzyl-2-bromo-3-methoxypropionamide and intermediates thereof
CN107118198A (en) * 2017-06-08 2017-09-01 福州大学 Have rhodamine B derivative of antitumaous effect and fluorescence property and preparation method thereof concurrently
CN107118198B (en) * 2017-06-08 2019-07-09 福州大学 Have the rhodamine B derivative and preparation method thereof of antitumaous effect and fluorescence property concurrently

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