CN101260219A - Method for preparing triblock copolymer micelle system used for realizing reversible fluorescence regulation and control - Google Patents
Method for preparing triblock copolymer micelle system used for realizing reversible fluorescence regulation and control Download PDFInfo
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- CN101260219A CN101260219A CNA2008100276637A CN200810027663A CN101260219A CN 101260219 A CN101260219 A CN 101260219A CN A2008100276637 A CNA2008100276637 A CN A2008100276637A CN 200810027663 A CN200810027663 A CN 200810027663A CN 101260219 A CN101260219 A CN 101260219A
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Abstract
The invention discloses a preparation method for a triblock copolymer micelle system used to realize reversible fluorescent adjustment. The preparation method comprises the following steps: (1) hydrophilic macromolecular initiator, hydrophobic monomer and monomer containing optical active group are synthesized into triblock copolymer containing a hydrophilic segmer, a hydrophobic segmer and an optical active dye segmer through adopting a method of atom transfer and free radical polymerization; (2) after the triblock copolymer is dissolved by low-boiling point organic solvent, deionized water is added so as to obtain triblock copolymer nano micelle after rotary evaporation; (3) after hydrophobic fluorescent dye is prepared into solution by low-boiling point organic solvent, the low-boiling point organic solvent is dried and then micelle solution is added and stirred; thus, the mixture is cooled down to room temperature and is stirred over night so as to obtain a nano micelle system loaded with the hydrophobic fluorescent dye. Due to having excellent biocompatibility and innocuity, the hydrophilic polyethylene glycol and the polyethylene imine segmer of the invention, which are formed into the shell of the nano micelle, can increase the biocompatibility of the nano micelle.
Description
Technical field
The present invention relates to a kind of preparation method who is used to realize the triblock copolymer micelle system of reversible fluorescence regulation and control.
Background technology
Material with optics regulation and control performance has received increasing concern in biotechnology and optical material field.Wherein, in many Application Areass such as biological detection, sensing, radiography, the fluorescent mark technology has obtained significant progress, and become a kind of topmost technique means that realizes above-mentioned functions, and also be important development trend at present to the Modulatory character of fluorescence, for example, the fluorescent mark with the adjustable sky of fluorescence can be used to pair cell or the other biological tissue optionally improves brightness.
Traditional regulation and control to fluorescent signal adopt the framework of two colour solids (dyad) or three colour solids (triad) to be realized usually.The fluorescent emission that this framework can utilize the structural changes of acceptor to modulate donor by energy transfer or transfer transport.Organic molecule structure with dyad or triad structure is clear and definite, and the length that can utilize spacer in the structure is accurately regulated, and energy shifts or the efficient of transfer transport, but it is complicated that shortcoming is the organic synthesis process, be easy to self aggregation in water, and generally lack biocompatibility, it is used at aqueous phase be subjected to restriction to a certain degree.The correlative study of fluorescent nano particles has received the concern of Chinese scholars just gradually under this background, and has obtained fast development in recent years.Fluorescent nano particles is groups such as fluorophore, probe to be connected by embedding, covalent linkage and mode such as supramolecule assembling is introduced in quantum dot, the organic or inorganic nanoparticle, and allows nanoparticle bear the functions such as detection, mark of organic molecule fluorescence dye.Compare with traditional fluorescence dye, fluorescent nano particles has higher brightness and light stability, also can realize water dispersible and biocompatibility more easily.In addition, along with the further raising of nanometer technology of preparing, to the accurate control of the yardstick of nanoparticle and to the becoming better and approaching perfection day by day of particle functionalization means, this makes fluorescent nano particles satisfy the requirement in fields such as chemical sensor, bioprobe to a great extent.Chinese patent CN101125968 is by coating the composite silicon dioxide nano particle that organic luminescent dye obtains, improved the luminous intensity height of nanoparticle, in biological imaging, can improve the sensitivity of detection, but its biocompatibility is very poor, and need use precious metals such as gold and silver, cost is very high.Chinese patent CN101109708 adopts 2, and 6-phenylbenzene-4-benzo 15 hat 5-pyridine compounds can be applicable to biology and ion detection field, but need to detect in the perchloric acid acidic solution as magnesium ion fluorescent probe, have limited its purposes.United States Patent (USP) 5403928 is connected to phthalein cyanogen dyestuff on end methoxyl group-polyoxyethylene glycol (PEG), improving its solvability and biocompatibility in water, but its easy reunion, stability is bad.
Summary of the invention
The present invention is directed to problems such as the fluorescence Modulatory character that traditional fluorescence dye exists is undesirable, biocompatibility is not good and be difficult for disperseing in water, a kind of method of utilizing triblock copolymer to realize reversible fluorescence regulation and control and biocompatibility is provided.
The present invention can be achieved by the following technical programs:
(1) utilize atom transfer radical polymerization method with wetting ability macromole evocating agent, hydrophobic monomer with contain synthetic a kind of hydrophilic segment, hydrophobic segment and the photolytic activity dyestuff segmental triblock copolymer of containing of monomer of optical active group;
(2) with adding deionized water behind the low boiling point organic solvent dissolving triblock copolymer, after 20-35 ℃ of rotary evaporation 2-3 hour, obtain the triblock copolymer nano-micelle;
(3) with low boiling point organic solvent the hydrophobicity fluorescence dye is mixed with behind the solution the low boiling point organic solvent drying, add micellar solution again and stirred the companion 5-6 hour at 45-60 ℃, cool to room temperature stirs the companion and spends the night, and has obtained loading the nano-micelle system of hydrophobicity fluorescence dye.
Compared with prior art, the present invention has the following advantages:
(1), the present invention adopts atom transfer radical polymerization (ATRP) method, it is clear and definite to have obtained structure, molecular weight is controlled, the triblock copolymer of narrow molecular weight distribution.
(2), institute of the present invention synthetic triblock copolymer is amphipathic, can form with hydrophobic polymethylmethacrylate or polystyrene in water be nuclear, hydrophilic polyoxyethylene glycol or polymine are the stable nanometer micelle that contains the photolytic activity spiropyran compounds in the stratum nucleare of shell, absorption of nuclear/shell interfacial energy and spiro-pyrans generation energy shift the hydrophobicity fluorescence dye of energy level coupling, make and high efficiency energy takes place between donor groups (hydrophobicity fluorescence dye) under the excited state and acceptor groups (photolytic activity dye groups) shift, can realize the stable reversible fluorescence regulation and control performance of micellar system.
(3), hydrophilic polyoxyethylene glycol of the present invention and polymine segment have good biocompatibility, nontoxic, it has constituted the shell of nano-micelle, has so just improved the biocompatibility of nano-micelle.
In general, utilize triblock copolymer to realize reversible fluorescence regulation and control and biocompatibility.
Embodiment
Embodiment 1
In the single port flask of magnetic stir bar is housed, add polyoxyethylene glycol (PEO) 60g, 4-Dimethylamino pyridine 1.96g and triethylamine 1.3g, the 120mL methylene dichloride, and, lead to nitrogen protection with cryosel bath cooling.Alpha-brominated isobutyl acylbromide 5.84g is dissolved in the 40mL methylene dichloride, joins in the above-mentioned reaction mixture, stirring at room reaction 24 hours.Reaction after finishing is fallen the methylene dichloride rotary evaporation, adds the benzene lysate, filters, and filtrate concentrates, the anhydrous diethyl ether precipitation, and vacuum-drying obtains flaxen PEO-Br macromole evocating agent.With the PEO-Br macromole evocating agent is initiator, and methyl methacrylate (MMA) is a monomer, and CuCl/PMDETA is a catalyst system, and dimethylbenzene is solvent, with the synthetic PEO-b-PMMA di-block copolymer of atom transfer radical polymerization (ATRP) method.Be initiator again with PEO-b-PMMA, equally with the synthetic PEO-b-PMMA-b-PSPMA triblock copolymer of ATRP method.
In the single necked round bottom flask of 50mL, with the tetrahydrofuran (THF) of 1.5mL dissolving 0.03g triblock copolymer, treat dissolving fully after, add the deionized water of 15mL.At 20-35 ℃ of following rotary evaporation 2-3 hour, solution dilution promptly obtained the triblock copolymer nano-micelle to 1.0g/L.Measurement through atomic force microscope (AFM) and dynamic light scattering (DLS) has confirmed gained triblock copolymer nano-micelle for spherical, and median size is 20～40nm.
With methylene dichloride lipotropy carbonyl cyanine dye Dil is mixed with 1 * 10
-3The solution of mol/L adds 0.8mL solution in the brown volumetric flask of 10mL.Behind the methylene dichloride complete drying, add the micellar solution 10mL of 1g/L, stirred 5 hours at 45 ℃, cool to room temperature stirs and spends the night then, has promptly obtained loading the nano-micelle system of hydrophobicity fluorescence dye.
Shine the nano-micelle system of gained respectively with UV-light and visible light, measure the fluorescent emission intensity of nanoparticle system under this two states, be respectively 86 and 1965 at the 330nm place, and carry out repeatedly irradiation and measurement, the nano-micelle diagram of system has revealed the fluorescent switch effect and the good reversibility of high-contrast, has gratifying reversible fluorescence regulation and control performance.
Embodiment 2
In the single port flask of magnetic stir bar is housed, add polymine (PEI) 60g, 4-Dimethylamino pyridine 1.96g and triethylamine 1.3g, the 120mL methylene dichloride, and, lead to nitrogen protection with cryosel bath cooling.Alpha-brominated isobutyl acylbromide 5.84g is dissolved in the 40mL methylene dichloride, joins in the above-mentioned reaction mixture, stirring at room reaction 24 hours.Reaction after finishing is fallen the methylene dichloride rotary evaporation, adds the benzene lysate, filters, and filtrate concentrates, the anhydrous diethyl ether precipitation, and vacuum-drying obtains flaxen PEI-Br macromole evocating agent.In having the round-bottomed flask of magnetic stir bar, add PEI-Br macromole evocating agent 3g, vinylbenzene 16.52g, CuCl 0.059g, N, N, N ', N ", N " pentamethyl-diethylenetriamine (PMDETA) 0.0311g and 20.0g dimethylbenzene thaw reaction solution after the stirring and dissolving by liquid nitrogen freezing-vacuumize-applying argon gas, three deoxygenations that circulate, vacuum-sealing.Reaction solution adds tetrahydrofuran (THF) dilution after being reacted to preset time under 110 ℃, by short neutral alumina post, rotary evaporation falls most tetrahydrofuran (THF) more then, petroleum ether precipitation, vacuum-drying is to constant weight, get final product the PEI-b-PS di-block copolymer.With PEI-b-PS is initiator, equally with the synthetic PEI-b-PS-b-PMAPO triblock copolymer of ATRP method.
In the single necked round bottom flask of 50ml, with the acetone solution 0.03g triblock copolymer of 1.5mL, treat dissolving fully after, add the deionized water of 15mL.At 20-35 ℃, rotary evaporation 2-3 hour, solution dilution promptly obtained the triblock copolymer nano-micelle to 1.0g/L.Measurement through atomic force microscope (AFM) and dynamic light scattering (DLS) has confirmed gained triblock copolymer nano-micelle for spherical, and median size is 20～40nm.
With ethanol tonka bean camphor 153 is mixed with 1 * 10
-3The solution of mol/L adds 0.8mL solution in the brown volumetric flask of 10mL.Behind the ethanol complete drying, add the micellar solution 10mL of 1g/L, stirred 5.5 hours at 50 ℃, cool to room temperature stirs and spends the night then, has promptly obtained loading the nano-micelle system of hydrophobicity fluorescence dye.
Shine the nano-micelle system of gained respectively with UV-light and visible light, measure the fluorescent emission intensity of nanoparticle system under this two states, be respectively 87 and 1876 at the 330nm place, and carry out repeatedly irradiation and measurement, the nano-micelle diagram of system has revealed the fluorescent switch effect and the good reversibility of high-contrast, has gratifying reversible fluorescence regulation and control performance.
Embodiment 3
With methylene dichloride ceramide NBD-C8 is mixed with 1 * 10
-3The solution of mol/L adds 0.8mL solution in the brown volumetric flask of 10mL.Behind the methylene dichloride complete drying, add the micellar solution 10mL of 1g/L, stirred 6 hours at 60 ℃, cool to room temperature stirs and spends the night then, has promptly obtained loading the nano-micelle system of hydrophobicity fluorescence dye.
Shine the nano-micelle system of gained respectively with UV-light and visible light, measure the fluorescent emission intensity of nanoparticle system under this two states, be respectively 86 and 1792 at the 330nm place, and carry out repeatedly irradiation and measurement, the nano-micelle diagram of system has revealed the fluorescent switch effect and the good reversibility of high-contrast, has gratifying reversible fluorescence regulation and control performance.
Claims (7)
1, a kind of preparation method who is used to realize the triblock copolymer micelle system of reversible fluorescence regulation and control is characterized in that may further comprise the steps:
(1) utilize atom transfer radical polymerization method with wetting ability macromole evocating agent, hydrophobic monomer with contain synthetic a kind of hydrophilic segment, hydrophobic segment and the photolytic activity dyestuff segmental triblock copolymer of containing of monomer of optical active group;
(2) with adding deionized water behind the low boiling point organic solvent dissolving triblock copolymer, after 20-35 ℃ of rotary evaporation 2-3 hour, obtain the triblock copolymer nano-micelle;
(3) with low boiling point organic solvent the hydrophobicity fluorescence dye is mixed with behind the solution the low boiling point organic solvent drying, add micellar solution again and stirred the companion 5-6 hour at 45-60 ℃, cool to room temperature stirs the companion and spends the night, and has obtained loading the nano-micelle system of hydrophobicity fluorescence dye.
2, preparation method according to claim 1 is characterized in that the described wetting ability macromole evocating agent of step (1) is polyoxyethylene glycol or polymine.
3, preparation method according to claim 2 is characterized in that the described hydrophobic monomer of step (1) is methyl methacrylate or vinylbenzene.
4, preparation method according to claim 3 is characterized in that the described photolytic activity dye groups of step (1) is spiropyran groups or azobenzene group.
5, preparation method according to claim 4 is characterized in that the described low boiling point organic solvent of step (2) is tetrahydrofuran (THF) or acetone.
6, preparation method according to claim 5 is characterized in that the described low boiling point organic solvent of step (3) is methylene dichloride or ethanol.
7, preparation method according to claim 6 is characterized in that the described hydrophobicity fluorescence dye of step (3) is a kind of among lipotropy carbonyl cyanine dye Dil, tonka bean camphor 153 and the ceramide NBD-C8.
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