CN105001406B - The new method of selenocysteine in a kind of detection live body - Google Patents
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- CN105001406B CN105001406B CN201510332431.2A CN201510332431A CN105001406B CN 105001406 B CN105001406 B CN 105001406B CN 201510332431 A CN201510332431 A CN 201510332431A CN 105001406 B CN105001406 B CN 105001406B
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Abstract
It is of the invention reasonably to design and be prepared for a kind of carbonate polymer PMPC Dns of new 2,4 dinitrobenzenesulfonyls modification to detect selenocysteine in live body.The compound can wrap up fluorescent drug adriamycin (DOX), and optionally respond Sec and selenol compound, and from the interference of biological thiol, amine, alcohols.The insoluble drug release that our formation to micella, the response of Sec, the cytotoxicity of probe and Sec are responded is studied.PMPC Dns micella probes can be applied to be imaged the endogenous Sec in cervical cancer tissues and HeLa cell living in physiological conditions, and PMPC Dns micellas probe can be imaged and discharge the medicine being wrapped in inside it at the same time.This work is understands that effects of the Sec in physiology, pathology system and Tumor Xenograft Models system opens a road, and also the controlled release for the hydrophobic molecule in target molecule in biomedical applications provides a method that.
Description
【Technical field】
The invention belongs to organic synthesis and detection field, relates in particular to a kind of giving birth to for dinitrobenzenesulfonyl modification
The synthetic method of the makrolon micella of thing degraded and its detection to the selenocysteine in tissue.Using makrolon as
Hydrophobic chain, using the ring-opening polymerisation (ROP) of cyclic carbonate it is easy synthesized amphipathic polymer.Then nitrine and alkynes are in copper
The lower coupling reaction that Huisgen 1,3- dipole-diople interactions occur of catalysis forms the makrolon micella to Sec responses.
【Background technology】
In 1969, the anti-cancer ability of Se was found in the U.S., and find selenium intake also always with many diseases
It is related.The selenium compound of low molecular weight, if methyl-hydroselenide and selenocysteine (Sec) they are crucial metabolins, and it was found that its
It is critically important in terms of cancer prevention.Particularly selenocysteine, it is that a kind of the important of low molecular weight contains selenoaminoacid, and
Encoded positioned at the avtive spot of selenoprotein, and by eryphysine adenosine (UGA) terminator codon.In addition, Sec can enter selenium egg
White active site, and the function of selenoprotein is extensive, including from redox signal function, anti-inflammatory effect to active thyroid gland
The secretion of hormone.Sec controls the multiple functions of various selenium-containing compounds in species body and is also played in treatment of cancer
Important effect.Up to the present, the fluorescence probe of few document report detection Sec or selenoprotein.In 2006, Maeda
Etc. reporting a kind of fluorescence probe BESThio for distinguishing Sec and Cys in selenol, which can make Sec with more reactivity,
And it is ionized form during ph values 5.8.Reported at 2014 etc. under the physiological condition of pH value 7.4, according to identical
Mechanismic design, synthesized a series of potential Sec probes and carried out BIOLOGICAL EVALUATIONIn to it.In 2015, Kong etc. developed one
The fluorescent method of Sec obtains the physiological function of Sec in kind of detection living cells, while have studied suppression machines of the Se to tumour cell
System.But (require potential destructive load technology or high dye due to lacking cell permeability and being detained (EPR) effect
Colour saturation), anti-light bleaching and biocompatibility still limit biomedical extensive use.Inspired by such precedent, I
Construct the Sec detecting systems for including chemical reaction and biodegradable polymer micella herein.Micella can be in life
Endogenous Sec is imaged under the conditions of reason, this shows that in cervical cancer tissues living and HeLa cells PMPC-Dns micellas probe can be with
Imaging, while discharge the medicine of parcel.
At present, the conjunction for the biodegradable makrolon micella do not modified both at home and abroad on dinitrobenzenesulfonyl also
Into and its in tissue selenocysteine detection open source literature and patent application.
【The content of the invention】
It is an object of the invention to provide a kind of biodegradable makrolon micella of dinitrobenzenesulfonyl modification
To detect the method for the selenocysteine in tissue.The PMPC-Dns for being wrapped in fluorescent drug DOX can be in physiological condition
Under (pH value 7.4) optionally respond Sec and other selenols, and very little is disturbed to other biological mercaptan, amine or alcohol.PMPC-Dns
Micella probe can also be applied to the endogenous Sec in imaging Hela cells, and the cervical cancer tissues of work in physiological conditions
In, PMPC-Dns micellas probe, which can be imaged and discharge at the same time, is wrapped in medicine therein.To achieve the above object of the invention, it is of the invention
It is proposed following technical solution：
The hydrophobic side of the recognition site 2,4- dinitrobenzenesulfonyls of Sec and polycarbonate backbone is copolymerized.When
PMPC-Dns copolymers and adriamycin (DOX) are placed in aqueous solution, and self assembly occurs for micella, and hydrophobic adriamycin is wrapped
In micella.When there is Sec, recognition site reacts with Sec causes 2,4- dinitrobenzenesulfonyls to be broken, and hydrophobic side becomes
Micella is dissociated for hydrophilic hydroxyl terminal.The dissociation of micella discharges the adriamycin of parcel, so that micellar fluorescence intensity increases
Achieve the purpose that detection by force.
In above-mentioned detection method, polymer has been formulated for substrate with 2,4- dinitrobenzenesulfonyls and polycarbonate backbone
Synthetic route.
In above-mentioned detection method, micella is prepared with polymer.
In above-mentioned detection method, the concentration (CMC) of critical micell is determined with fluorescence detection.
In above-mentioned detection method, with the toxicity of MTT colorimetric determination cells.
In above-mentioned detection method, determine the PMPC-Dns micellas to the Sec operation principles detected and feasibility with fluorescence method.
In above-mentioned detection method, the sensitivity of Sec and selectivity are detected with fluorescence method.
In above-mentioned detection method, with PMPC-Dns micellas come detect cell and tissue in Sec.
PMPC-Dns micellas provided by the present invention, are the micellas with stimuli responsive, its main feature is that stablizing, being simple, spirit
It is quick, cost is low, it is light and easily storage.PMPC-Dns micellas are first selective micella probes that can be used for Sec inductions.
【Brief description of the drawings】
It is the biodegradable makrolon glue of synthesis dinitrobenzenesulfonyl modification provided by the invention shown in attached drawing
The path profile of fasciculation compound.
【Embodiment】
The biodegradable makrolon micella compound of synthesis dinitrobenzenesulfonyl modification provided by the present invention
Reaction scheme, refer to attached drawing.
With reference to specific preparation example, the present invention will be further described：
PMPC-Dns micellas synthesize
The synthesis of 3- nitrine -1- propyl alcohol
Into 50mL reaction tubes, 1.02g 3- bromopropyl alcohols are added, 0.95g Sodium azides, add 10mL distilled water, in 80 DEG C
Lower reaction 18h, stops heating, is cooled to room temperature, adds ethyl acetate to extract, take upper liquid, then with aqueous salt solu-tion, anhydrous sulphur
Sour magnesium drying, filtering, filtrate are collected, and are removed solvent and are obtained colourless 3- nitrine -1- propyl alcohol, yield 76.5%.
Synthesis (the Dns-N of 2,4- dinitrobenzene sulfonic acid propyl ester3)
Into 50mL round-bottomed flasks, 0.57g 3- nitrine propyl alcohol is added, 1.56mL triethylamines, add the anhydrous dichloros of 10mL
Methane, is slowly added to 2, the 4- dinitrophenyl chlorides of anhydrous methylene chloride dissolving, stirring, reacts 18h, add water to extract at 0 DEG C
Take, take upper liquid, anhydrous magnesium sulfate drying, filtering, filtrate collection, removes solvent and obtain crude product, cross post separation (PE:EA=5：
1) product, yield 72%, are obtained.
The synthesis (2) of 2,2- dihydromethyl propionic acid propynyl esters
Into 50mL round-bottomed flasks, 2.24g 2 is added, 2- dihydromethyl propionic acids, 1.01g potassium hydroxide, adds 20mL
DMF, reacts 2h at 100 DEG C, then 2.13g propargyl bromides are added dropwise, and half an hour drop finishes, and reacts 72h, stops reaction, filtering, subtracts
Pressure is spin-dried for solvent, adds CH2Cl2Dissolving, the saline solution extraction (20mL × 3) of saturation, collects organic phase and obtains crude product, cross column point
From (PE:EA=5：1) product, yield 45.14%, are obtained.
The synthesis of MPC
Into two mouthfuls of round-bottomed flasks of 50mL, 1.18g compounds 2 are added, 1.48g ethyl chloroformates, add 20mL DMF,
1h is stirred under ice bath under nitrogen protection, then 1.39g triethylamines are added dropwise, half an hour drop finishes, and 3h is after mistake at room temperature for reaction
Night reacts, and filtering, decompression is spin-dried for solvent, crude product ethyl acetate：Ether=1:1 recrystallization, obtains white crystalline product, produces
Rate 91.05%.
The synthesis of PEG-b-poly (MPC)
The ring-opening polymerisation of MPC is the Xi Laike technologies using standard, is carried out under nitrogen protection.To 50mL Schlenk
In bottle, 0.594g MPC, 0.601g PEG are added5k, 0.055g TU, 0.005g DBU, add 10mL CH2Cl2, rubber stopper
Sealing, then it is that solid-state-vacuumizing-is thawed and circulated three times to pass through freezing, and 7h is stirred at room temperature, ether on the rocks separates out precipitation, and centrifugation divides
From filtering, is spin-dried for solvent, obtains white powder product, yield 92.0%.
Click chemistry synthesizes PMPC-Dns
Into Schlenk bottles of 50mL, 302.9mg PEG-b-poly (MPC), 245.06mg Dns-N are added3, 17.1mg
Sodium ascorbate, adds 4mL DMF, rubber stopper sealing, then by freezing be after solid-state-vacuumizing-is thawed and circulated three times, to add
Enter the 10.55mg copper sulphate of DMF dissolvings, reaction 24h is stirred at room temperature, with deionized water 3 days (bag filter 3500MWCO) of dialysis, ice
Jelly method obtains product, yield 75.60%.
Detection of the PMPC-Dns micellas to Sec
It is prepared by micella
The micella of PEG-b-poly (MPC) and PMPC-Dns is prepared by dialysis.25.0mg copolymers are taken to be dissolved in four
In hydrogen furans, 10mL deionized waters are slowly added under stirring.2h is stirred at room temperature, micella is made, then with deionized water dialysis 24h
DMF (MWCO 1000Da) is removed, then it is 0.5mg mL to add deionized water to adjust final polymer concentration-1。
The measure (CMC) of critical micelle concentration
The critical micelle concentration of MPC polymer and PMPC-Dns amphipathic polymers (CMC) is to be used as spy using Nile red (NR)
Pin molecule is measured by dye solubilization method.Nile red (the 0.1mg mL that will be dissolved in microsyringe in THF-1,30
μ L) inject in a vial, THF is evaporated, adds the micellar solution of 2mL, stirs 5h, the concentration of micellar solution is 0.1
~5 × 10-4mg mL-1.Fluoroscopic examination is carried out under the excitation wavelength of 550nm, obtains the transmitted wave of 570nm to 750nm.
The detection of cytotoxicity
Assessment of the micella to the cytotoxicity of the HeLa cell as model has used the cytoactive detection method of standard i.e.
MTT colorimetric method for determining.Hela cell inoculations are 5 × 10 in 96 orifice plates, and in concentration3100 μ containing 10% hyclone of cell
In L MEM culture mediums, when hatching 24 is small in 5% carbon dioxide, 95% air and at 37 DEG C.Then, by culture medium with 200 μ
L polymer micelles substitute.It is prepared for the total concentration of each formula respectively with DMEM media dilution methods.The culture medium of cell culture
For control.Cell is washed three times with PBS, then by 100 μ L MTT solution (in 0.5mg mL-1In PBS) it is added in each aperture.
After adding DMSO (150 μ L/well), detection plate is shaken 10 minutes at room temperature.The experiment is parallel to be done three times.Surveyed based on 570nm
Determine ultraviolet-ray visible absorbing, and cell survival rate, OD are calculated using the following formula570Represent optical density.
Cell viability=[OD570(sample)-OD570(blank)]/[OD570(control)-OD570
(blank)]
PMPC-Dns micellas are to the Sec operation principles detected and feasibility
The recognition site 2,4- dinitrobenzenesulfonyls of Sec and the hydrophobic side of polycarbonate backbone are copolymerized.Work as PMPC-
Dns copolymers and adriamycin (DOX) are placed in aqueous solution, and self assembly occurs for micella, and hydrophobic adriamycin is wrapped in glue
Shu Zhong.When not having Sec, the recognition site of Sec is stable in physiological conditions, this make it that micella is also stable.On the contrary,
When there is Sec, recognition site reacts with Sec causes 2,4- dinitrobenzenesulfonyls to be broken, and hydrophobic side is changed into hydrophily
Hydroxyl terminal dissociate micella.The dissociation of micella discharges the adriamycin of parcel, so that micellar fluorescence intensity enhancing.Therefore,
The concentration of Sec can be represented with the enhancing degree of fluorescence intensity.
In order to verify feasibility that copolymeric micelles detect Sec, the PMPC-Dns glue of the Sec responses of parcel Dox is prepared for
Beam.It has detected whether PMPC-Dns micellas have fluorescence reaction to Sec.As expected, when in micellar solution (0.5mg
mL-1) in add Sec, doxorubicin fluorescence intensity ratio does not have to enhance during Sec at 590nm.At 590nm, due to adding Sec
The value that (1 μM) makes micellar fluorescence intensity ratio original adds 2.78 times.In order to further assess its feasibility, examined at 590nm
The fluorescence for having surveyed micella when adduction does not add Sec changes with time.When there is no Sec, in 10 minutes it was observed that at 590nm
Non-blooming change, this shows that micella is stabilization and will not discharge DOX in physiological conditions.On the contrary, in the presence of Sec, Ah
The fluorescence intensity of mycin is remarkably reinforced, and is reached highest after 1.6h and shown that it is all discharged.These experiments clearly show, successful
Ground has synthesized the PMPC-Dns micellas that can respond Sec.
Sec sensitivitys and selective enumeration method
In order to verify the applicability to Sec quantitative detecting methods proposed, we measure a series of molten in PBS bufferings
The fluorescence spectrum of PMPC-Dns micellas containing different Sec concentration in liquid.The concentration of increase Sec causes more 2,4- dinitro benzenes
Sulfonyl generation cracking is unstable with micella, so as to improve the cracking of micella and discharge DOX, this is glimmering compared with being not added with Sec
Luminous intensity significantly strengthens.With the increase of Sec concentration, fluorescence intensity substantially increases, and is in concentration dependent.Its range of linearity
Between 0-25 μM.With the further increase of Sec concentration, micella has cracked and fluorescence reaches a peak.Based on 3 σ
Rule, its detection are limited to 0.05 μM.
Because prior document is described to have high selection on 2,4- dinitrobenzenesulfonyls to Sec recognition sites
Property, so detection of the PMPC-Dns micellas to Sec also has high selectivity.Then we with regard to PMPC-Dns to the selectivity of Sec into
Go and determined.In the presence of various high concentration reducing agents, including mercaptan, beta -mercaptoethanol, thioredoxin reductase
(TrxR), dithiothreitol (DTT) (DTT), N-acetylcystein (NAC), vitamin C, hydrogen sulfide (H2S), sodium selenite and sub- selenium
The mixture of sour sodium, detects Cys and GSH, and the go back original reagent containing sulfydryl and inorganic sulphide becomes without obvious fluorescence
Change shows that it does not respond to probe.Vitamin C is also not responding to probe.The possible original that micella does not respond to TrxR
Because being that the Sec residues in SePs are difficult to close to its recognition site due to space steric effect.Since Sec is by (Sec)2
Made from DTT, singly there is DTT (50 μM) not respond under the same conditions.This shows that micella does not ring above-mentioned reducing agent
Should.Wherein dithiothreitol (DTT) (DTT), N-acetylcystein (NAC), vitamin C, Cys and GSH structural formulas difference are as follows:
PMPC-Dns micellas detect the Sec in cell and tissue
For biologic applications, the long-term cytotoxicity of PEG-b-poly (MPC) and PMPC-Dns micellas to Hela cells
It is to be measured by the mtt assay of a standard.When the concentration of micella is 1mg mL-1When, cell survival rate remains at 93% or so, table
Reveal relatively low cytotoxicity.This result has good biocompatibility mainly due to PEG and PC.In addition, highly concentrated
Under the conditions of the hyclone (FBS) of degree, the stability of PMPC-Dns micellas is also extremely important, particularly the detection to tissue.This
It is to be studied by detecting its fluorescence spectrum in different storage times.The result shows that under biotic factor, PMPC-Dns
Micella can long-time stable presence.These results indicate that quantitative detection of the PMPC-Dns micellas to Sec is with selective and sensitive
Property, and Sec can be used for the targeting target of the delivery system for the treatment of cancer.
Living cells imaging is carried out in Hela cells.Due to low physiological concentrations of the Sec in cell, so we are true first
Determine whether PMPC-Dns micellas can respond exogenous Sec.Sec is added in the Hela cells in vitro culture from 2 to 12h
In, a bright red fluorescent occurs, but without obvious Fluorescence Increasing.This breathtaking discovery promotes me
Further probe into endogenic Sec in cell.Sodium selenite is the precursor of Sec biosynthesis, and sodium selenite is to cell
Supplement can significantly improve the content of Sec in cell.After cell is subject to sodium selenite to stimulate 12h, there is significant fluorescence.
During the stimulation of 2h short time, signal that is weak but being remarkably reinforced is also given.These results indicate that micella be can in living cells into
As Sec.
Further to inquire into response of the PMPC-Dns micellas under biotic factor, cervix neoplasms tissue also be used to be imaged.
After Sec 12h are incubated to cervix neoplasms histotomy, it is observed that strong fluorescence signal, and it is incubated uterine neck with sodium selenite
Histotomy same time has obtained hypofluorescence signal.Moreover, Sec or Na ought not be incubated to cervix neoplasms histotomy2SeO3
When, just without obvious Fluorescence Increasing.It is interesting that this result is consistent completely with Hela cell imagings.Co-focusing imaging
Result clearly illustrate that PMPC-Dns micellas can detect the Sec in cervical carcinoma under biotic factor.
Embodiment described above only expresses the several embodiments of the present invention, its description is more specific and detailed, but simultaneously
Therefore the limitation to the scope of the claims of the present invention cannot be interpreted as.It should be pointed out that for those of ordinary skill in the art
For, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to the guarantor of the present invention
Protect scope.Therefore, the protection domain of patent of the present invention should be determined by the appended claims.
Claims (4)
- A kind of 1. method for detecting selenocysteine in live body, it is characterised in that PMPC-Dns optionally responds Sec and selenium Alcoholic compound, and from the interference of biological thiol, amine, alcohols；And PMPC-Dns micella probe applications are in physiological conditions Endogenous Sec in imaging cervical cancer tissues living and HeLa cell, while release is wrapped in the drug adriamycin DOX inside it； The structural formula difference of wherein described PMPC-Dns, Sec and DOX are as follows：
- 2. a kind of method for detecting selenocysteine in live body according to claim 1, it is characterised in that use makrolon As hydrophobic chain, amphipathic polymer has been synthesized using cyclic carbonate ring-opening polymerisation；Nitrine occurs with alkynes under copper catalysis The coupling reaction of Huisgen 1,3- dipole-diople interaction, has obtained the makrolon micella based on hydrophobic Sec responses.
- 3. a kind of method for detecting selenocysteine in live body according to claim 1, it is characterised in that amphipathic common Polymers PMPC-Dns is self-assembled into the micella using hydrophobic side as one hydrophilic outer shell of core encapsulation.
- A kind of 4. method for detecting selenocysteine in live body according to claim 1, it is characterised in that physiological condition I.e. pH value is 7.4.
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| CN1274007A (en) * | 1999-05-13 | 2000-11-22 | 中国科学院长春应用化学研究所 | Process for preparing Se-contained humanized abzyme |
| CN1307042A (en) * | 2000-01-28 | 2001-08-08 | 上海博道基因技术有限公司 | Polypeptide-human selenocysteine tRNA specific related protein SECp 43, 32 and polynucleotide for coding said polypeptide |
| WO2004052376A1 (en) * | 2002-12-10 | 2004-06-24 | Health Research, Inc. | Method of reducing toxicity of anticancer agents |
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2015
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| CN1274007A (en) * | 1999-05-13 | 2000-11-22 | 中国科学院长春应用化学研究所 | Process for preparing Se-contained humanized abzyme |
| CN1307042A (en) * | 2000-01-28 | 2001-08-08 | 上海博道基因技术有限公司 | Polypeptide-human selenocysteine tRNA specific related protein SECp 43, 32 and polynucleotide for coding said polypeptide |
| WO2004052376A1 (en) * | 2002-12-10 | 2004-06-24 | Health Research, Inc. | Method of reducing toxicity of anticancer agents |
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| Organocatalytic synthesis and post-polymerization functionalization of propargyl-functional poly(carbonate)s;Tempelaar, Sarah;《Polymer Chemistry》;20120917(第4期);174-183 * |
| Photo-responsive reversible micelles based on azobenzene-modified poly(carbonate)s via azide-alkyne click chemistry;Hu, Ding;《Royal Society of Chemistry》;20140905;第89卷(第4期);47929-47936 * |
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