CN103908682A - Application of poly-dopamine nano-particles - Google Patents
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Abstract
The invention provides an application of poly-dopamine nano-particles. By researches, the inventor discovers that the poly-dopamine nano-particles have strong absorbability in the near-infrared area, and have an excellent imaging effect when being used as a photoacoustic imaging contrast agent. Experiment results indicate that the poly-dopamine nano-particles have strong photoacoustic signals, high photoacoustic imaging contrast degree and clear images.
Description
Technical field
The present invention relates to photoacoustic imaging contrast agent field, relate in particular to the application of poly-dopamine nanoparticle.
Background technology
Photoacoustic imaging is the harmless medical imaging means of one that grow up recent years, it is the mixed model formation method of setting up based on optoacoustic effect, combine the high-contrast of pure optical imagery and the high-penetrability of pure ultra sonic imaging, by photoacoustic imaging, can obtain the imaging of tissue of high-resolution and high-contrast.Recent studies confirm that, photoacoustic imaging can be used for many life and the medical domains such as tumor neovasculature detection, blood oxygen saturation scanning, brain function imaging and cutaneous melanoma detection.
At present, in imaging field, photoacoustic imaging is applied is thermal-elastic expansion mechanism.Photoacoustic imaging process based on thermoelasticity mechanism refers to: by a branch of short pulse (ns magnitude) laser irradiation biological tissue, after thering is the absorbent body light energy of strong optical absorption characteristic in biological tissue, light energy causes that absorber rises mild inflation, thereby the expansion of absorber volume can be pushed absorber, tissue around produces local pressure ripple, the difference of absorbent body character, the for example size of hemoglobin concentration, the height of tissue oxygenation saturation, all can affect the light absorpting ability of absorber, thereby change the intensity of ultrasonic signal, by the spatial distribution of detector detecting ultrasonic signal intensity, thereby reflect the pathology information of imaging object.
DIC material of the prior art, as Graphene, CNT etc., owing to having very large specific surface area, is widely used as bio-carrier and carries out biological detection, drug conveying etc.In addition, it also has optics and magnetic property, is also used as nuclear magnetic resonance and photoacoustic imaging, but its during as photoacoustic imaging contrast agent a little less than the absorption of near infrared region, be difficult to obtain good imaging effect.
Summary of the invention
In view of this, the object of the present invention is to provide the application of poly-dopamine nanoparticle.Poly-dopamine nanoparticle provided by the invention is stronger in the absorption of near infrared region during as photoacoustic imaging contrast agent, has good imaging effect.
The invention provides the application of a kind of poly-dopamine nanoparticle as photoacoustic imaging contrast agent.
Preferably, the particle diameter of described poly-dopamine nanoparticle is 20nm～230nm.
Preferably, the particle diameter of described poly-dopamine nanoparticle is 50nm～200nm.
Preferably, described in, be applied as:
Described poly-dopamine nanoparticle is as photoacoustic imaging contrast agent, the photoacoustic imaging at and intestinal position subcutaneous for head.
Preferably, the preparation method of described poly-dopamine nanoparticle comprises the following steps:
Dopamine hydrochloride is carried out in mixed solvent to oxidative polymerization, obtain poly-dopamine nanoparticle;
Described mixed solvent comprises water, alcohol compound and ammonia.
Preferably, the mass fraction of described ammonia is 25%～28%.
Preferably, the quality of described dopamine hydrochloride and the volume ratio of ammonia are (30～300) mg:1mL.
Preferably, the volume ratio of described water, alcohol compound and ammonia is (15～25): (40～50): (1～5).
Preferably, the temperature of described oxidative polymerization is 15 ℃～35 ℃.
Preferably, the time of described oxidative polymerization is 12h～72h.
The invention provides the application of poly-dopamine nanoparticle.The inventor studies discovery, and poly-dopamine nanoparticle has stronger absorption near infrared region, sets it as photoacoustic imaging contrast agent, has good imaging effect.Experimental result shows: the photoacoustic signal of poly-dopamine nanoparticle is strong, and photoacoustic imaging contrast is high, clear picture.
Accompanying drawing explanation
Fig. 1 is the transmission electron microscope picture of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 1;
Fig. 2 is the dynamic light scattering figure of the poly-dopamine nanoparticle of the embodiment of the present invention 1 preparation;
Fig. 3 is the uv absorption spectra of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 1;
Fig. 4 is the photoacoustic signal figure of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 1;
Fig. 5 is photoacoustce signal intensity-nanoparticle concentration results figure of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 1;
Fig. 6 is the photoacoustce signal intensity-time diagram of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 1;
Fig. 7 is the subcutaneous optoacoustic radiography design sketch of the head Balb/C nude mice of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 1;
Fig. 8 is the bowel radiography design sketch Balb/C nude mice of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 1;
Fig. 9 is the transmission electron microscope picture of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 2;
Figure 10 is the dynamic light scattering figure of the poly-dopamine nanoparticle of the embodiment of the present invention 2 preparation;
Figure 11 is the uv absorption spectra of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 2;
Figure 12 is the photoacoustic signal figure of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 2;
Figure 13 is the photoacoustce signal intensity-concentration map of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 2;
Figure 14 is the transmission electron microscope picture of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 3;
Figure 15 is the dynamic light scattering figure of the poly-dopamine nanoparticle of the embodiment of the present invention 3 preparation;
Figure 16 is the uv absorption spectra of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 3;
Figure 17 is the photoacoustic signal figure of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 3;
Figure 18 is the photoacoustce signal intensity-concentration map of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 3;
Figure 19 is the transmission electron microscope picture of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 4;
Figure 20 is the dynamic light scattering figure of the poly-dopamine nanoparticle of the embodiment of the present invention 4 preparation;
Figure 21 is the uv absorption spectra of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 4;
Figure 22 is the photoacoustic signal figure of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 4;
Figure 23 is the photoacoustce signal intensity-concentration map of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 4;
Figure 24 is the transmission electron microscope picture of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 5;
Figure 25 is the uv absorption spectra of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 5;
Figure 26 is the transmission electron microscope picture of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 6;
Figure 27 is the uv absorption spectra of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 6;
Figure 28 is the cytotoxicity test pattern of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 1, embodiment 2, embodiment 3 and embodiment 4 to L929 cell;
Figure 29 is that poly-dopamine nanoparticle prepared by the injection embodiment of the present invention 1, embodiment 2, embodiment 3 and embodiment 4 affects figure to the body weight of Balb/C Mus;
The ultra-violet absorption spectrum comparison diagram of poly-dopamine nanoparticle prepared by the graphene oxide of Figure 30 comparative example and embodiment 4.
The specific embodiment
The invention provides the application of poly-dopamine nanoparticle as photoacoustic imaging contrast agent.
The inventor studies discovery, and poly-dopamine has stronger absorption near infrared region, sets it as photoacoustic imaging contrast agent, has good imaging effect.Experimental result shows: the photoacoustic signal of poly-dopamine nanoparticle is strong, and photoacoustic imaging contrast is high, clear picture.
In the present invention, the particle diameter of described poly-dopamine nanoparticle is preferably 20nm～230nm, more preferably 50nm～200nm; Described poly-dopamine nanoparticle is as optoacoustic contrast agent, is preferably applied to the photoacoustic imaging at the subcutaneous and intestinal position of head.
The present invention does not have special restriction to the source of described poly-dopamine nanoparticle, adopt poly-dopamine nanoparticle well known to those skilled in the art, as adopted commercial goods, also can adopt the technical scheme of the poly-dopamine nanoparticle of preparation well known to those skilled in the art to prepare voluntarily.Concrete, in the present invention, the preparation method of described poly-dopamine nanoparticle, preferably includes following steps:
Dopamine hydrochloride is carried out in mixed solvent to oxidative polymerization, obtain poly-dopamine nanoparticle;
Described mixed solvent comprises water, alcohol compound and ammonia.
The present invention does not have special restriction to the order of described dopamine hydrochloride and mixed solvent mixing, preferably dopamine hydrochloride is joined in mixed solvent.The present invention is preferably soluble in water by dopamine hydrochloride, obtains dopamine hydrochloride solution, and dopamine hydrochloride solution is mixed with mixed solvent again.In the present invention, the concentration of described dopamine hydrochloride solution is preferably (20～80) mg/mL, more preferably (40～60) mg/mL
The present invention does not have special restriction to the source of described dopamine hydrochloride, adopt dopamine hydrochloride well known to those skilled in the art, as adopted the commercial goods of dopamine hydrochloride, also can adopt the technical scheme of preparing dopamine hydrochloride well known to those skilled in the art to prepare voluntarily.
In the present invention, described mixed solvent comprises water, alcohol compound and ammonia; Described alcohol compound preferably includes one or more in ethanol, propanol and glycerol, more preferably ethanol; Described water preferably includes one or more in distilled water, deionized water and tap water, more preferably comprises deionized water; The mass fraction of described ammonia is preferably 25%～28%, and more preferably 26%～27%.The present invention is preferably by regulating the mol ratio control of ammonia and dopamine hydrochloride to gather the particle diameter of dopamine nanoparticle; Concrete, in embodiments of the present invention, when the quality of dopamine hydrochloride and the volume ratio of ammonia are 250mg:1mL, the particle diameter of poly-dopamine nanoparticle is 160nm～230nm; When the quality of dopamine hydrochloride and the volume ratio of ammonia are 170mg:1mL, the particle diameter of poly-dopamine nanoparticle is 85nm～150nm; When the quality of dopamine hydrochloride and the volume ratio of ammonia are 125mg:1mL, the particle diameter of poly-dopamine nanoparticle is 50nm～90nm; When the quality of dopamine hydrochloride and the volume ratio of ammonia are 100mg:1mL, the particle diameter of poly-dopamine nanoparticle is 20nm～70nm.
The present invention preferably, under the condition stirring, is mixed to get mixed solvent by water, alcohol compound and ammonia; The temperature of described stirring is preferably 25 ℃～35 ℃, more preferably 28 ℃～32 ℃; The time of described stirring is preferably 25min～35min, more preferably 30min
In the present invention, the volume ratio of water, alcohol compound and ammonia in described mixed solvent is preferably (15～25): (40～50): (1～5), more preferably (18～22): (42～48): (1.5～4.5), most preferably are (19～21): (44～46): (2.0～4); The quality of described dopamine hydrochloride and the volume ratio of ammonia are preferably (30～300) mg:1mL, more preferably (100～250) mg:1mL.
The present invention preferably, under the condition of lucifuge, carries out oxidative polymerization by dopamine hydrochloride, obtains poly-dopamine nanoparticle.The present invention preferably carries out oxidative polymerization under the condition stirring.In the present invention, the temperature of described oxidative polymerization is preferably 15 ℃～35 ℃, more preferably 18 ℃～33 ℃, most preferably is 20 ℃～30 ℃; The time of described oxidative polymerization is preferably 12h～72h, and more preferably 15h～70h, most preferably is 20h～60h.
Complete after the oxidative polymerization of dopamine hydrochloride, the present invention preferably dialyses the product obtaining, centrifugal and washing, obtains poly-dopamine nanoparticle.The present invention does not have special restriction to the method for described dialysis, adopts dialysis scheme well known to those skilled in the art.In the present invention, the solvent of described dialysis is preferably deionized water; The molecular weight that the dialyzer that described dialysis adopts is held back is preferably 3500～15000Da, more preferably 7000～10000Da; The temperature of described dialysis is preferably 15 ℃～40 ℃, more preferably 20 ℃～35 ℃, most preferably is 25 ℃～30 ℃; The time of described dialysis is preferably 2.5 days～and 3.5 days, more preferably 3 days.
The present invention does not have special restriction to described method centrifugal and washing, adopts the centrifugal technical scheme with washing well known to those skilled in the art.In the present invention, described centrifugal rotating speed is preferably 10000rpm～20000rpm, and more preferably 12000rpm～18000rpm, most preferably is 15000rpm～16000rpm; The described centrifugal time is preferably 10min～60min, more preferably 20min～40min.In the present invention, the solvent of described washing is preferably deionized water; The number of times of described washing is preferably 3 times～5 times.
Obtain after the product of washing, the present invention is preferably dried the product of described washing.In the present invention, described dry preferably adopt vacuum drying or lyophilization.
The preserving type of the poly-dopamine nanoparticle that the present invention obtains does not have special restriction, can be dispersed in aqueous medium, preserves with liquid form; Described aqueous medium comprises that described aqueous medium is one or more in distilled water, normal saline, buffer solution, tissue culture medium and body fluid; The quality of described poly-dopamine nanoparticle and the volume of solvent are preferably (20～2000) μ g:1mL;
The poly-dopamine nanoparticle that the present invention obtains also can be preserved with solid form.
The particle diameter of the poly-dopamine nanoparticle that the present invention obtains is 20nm～230nm.
In an embodiment of the present invention, can, by the head subcutaneous location of the poly-dopamine nanoparticle injection experiments animal obtaining, observe the photoacoustic imaging effect of the poly-dopamine nanoparticle of preparation; Also the poly-dopamine nanoparticle obtaining can be entered in experimental animals by oral way, observe the photoacoustic imaging effect of dopamine nanoparticle at laboratory animal intestinal position.
The present invention carries out ultraviolet-visible spectrum test to the poly-dopamine nanoparticle obtaining.The method that the present invention carries out ultraviolet-visible spectrum test to described poly-dopamine nanoparticle does not have special restriction, adopts the technical scheme of ultraviolet-visible spectrum test well known to those skilled in the art.
Test result shows: the poly-dopamine nanoparticle that the present invention obtains has absorption within the scope of 600nm～900nm.
The present invention carries out transmission electron microscope analysis to the poly-dopamine nanoparticle obtaining.Analysis result shows: spherical in shape being uniformly distributed of poly-dopamine nanoparticle that the present invention obtains, the diameter of poly-dopamine nanoparticle is 20nm～230nm.
The present invention carries out the test of photoacoustic signal spectrum to the poly-dopamine nanoparticle obtaining, and detailed process is as follows:
To gather dopamine nanoparticle and inject agar prosthese, the agar prosthese that contains poly-dopamine nanoparticle is placed in to the thermostatic water tank of 34 ℃, choosing wavelength is 680nm～900nm, and wavelength interval is that 5nm carries out photoacoustic signal test.
Test result shows: the poly-dopamine nanoparticle that the present invention obtains has photoacoustic signal near infrared region, can be used as photoacoustic imaging contrast agent for photoacoustic imaging analysis.
The present invention tests the poly-concentration of dopamine nanoparticle and the relation of photoacoustce signal intensity, and detailed process is as follows:
The poly-dopamine nano-particle solution of series concentration is injected into respectively in agar prosthese, the agar prosthese of the poly-dopamine nanoparticle that contains variable concentrations obtaining is placed in to the constant water bath box of 34 ℃, uses multispectral photoacoustic imaging system to test its corresponding photoacoustce signal intensity.
Test result shows: photoacoustce signal intensity and the concentration of the poly-dopamine nanoparticle that the present invention obtains all have good linear relationship, can carry out the quantitative analysis of photoacoustic imaging according to its optoacoustic intensity.
The present invention tests the photoacoustic imaging radiography effect of the poly-dopamine nanoparticle obtaining, and detailed process is as follows:
The poly-dopamine nanoparticle of 0.1mL100 μ g/mL is injected under the scalp of male Balb/C nude mice, then nude mice is coated with transparent plastic film in the constant water bath box that is placed on 34 ℃, the mist maintenance laboratory animal that continues to pass into isoflurane and air, in narcotism, is used multispectral photoacoustic imaging system to carry out multispectral tomoscan;
The present invention is injected in the poly-dopamine nanoparticle of 0.2mL100 μ g/mL in the male Balb/C nude mouse of breaking off diet 12h with gavage pin, then nude mice is coated with transparent plastic film in the constant water bath box that is placed on 34 ℃, the mist maintenance laboratory animal that continues to pass into isoflurane and air, in narcotism, is used multispectral photoacoustic imaging system to carry out multispectral tomoscan.
Test result shows: the poly-dopamine nanoparticle that the present invention obtains has good radiography effect, clear picture, and contrast is high, is suitable for very much photoacoustic imaging visualization.
The invention provides the application of a kind of poly-dopamine nanoparticle as photoacoustic imaging contrast agent.Poly-dopamine has stronger absorption as photoacoustic imaging contrast agent near infrared region, has good imaging effect.Experimental result shows: the photoacoustic signal of poly-dopamine nanoparticle is strong, and photoacoustic imaging contrast is high, clear picture.
In order to further illustrate the present invention, below in conjunction with embodiment, the application of poly-dopamine nanoparticle provided by the invention is described in detail, but they can not be interpreted as to limiting the scope of the present invention.
Embodiment 1
The ammonia that is 25% by 20mL ethanol, 45mL deionized water and 1mL mass fraction is placed in 100mL reaction bulb, at 30 ℃, stirs 30min, obtains mixed solvent;
0.2528g dopamine hydrochloride is dissolved in 5mL deionized water, then the aqueous solution of dopamine hydrochloride is added in above-mentioned mixed solvent, lucifuge, at 30 ℃, stir, carry out oxidative polymerization 24h, reaction system, by the colourless light brown that gradually becomes, finally becomes black, products therefrom, through high speed centrifugation, deionized water wash three times, obtains poly-dopamine nanoparticle.
The present invention carries out transmission electron microscope analysis to the poly-dopamine nanoparticle obtaining, and as shown in Figure 1, Fig. 1 is the transmission electron microscope picture of the poly-dopamine nanoparticle that obtains of the embodiment of the present invention 1 to result.As seen from Figure 1, spherical in shape being uniformly distributed of poly-dopamine nanoparticle that the embodiment of the present invention 1 prepares, diameter is between 160nm～230nm.
The present invention carries out dynamic light scattering analysis to the poly-dopamine nanoparticle obtaining, and measures its hydrodynamic radius, and as shown in Figure 2, Fig. 2 is the hydrodynamic radius scattergram of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 1 to result.The hydrodynamic radius of the poly-dopamine nanoparticle that as seen from Figure 1, the embodiment of the present invention 1 obtains is between 80nm～180nm.
Can be found out by Fig. 1 and Fig. 2 contrast, the result of the transmission electron microscope gained size of poly-dopamine nanoparticle is slightly less than light scattering result, this is mainly because dynamic light scattering is more responsive for bulky grain, the gathering of a small amount of nanoparticle, or the existence of a small amount of dust all can make test result bigger than normal.
The poly-dopamine nanoparticle that the present invention obtains carries out ultraviolet-visible spectrum test, and as shown in Figure 3, Fig. 3 is the uv absorption spectra of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 1 to its uv absorption spectra.As seen from Figure 3, the poly-dopamine nanoparticle that the embodiment of the present invention 1 obtains has absorption within the scope of 600nm～900nm.
The present invention carries out photoacoustic signal spectrum test according to technique scheme to the poly-dopamine nanoparticle of preparation, and as shown in Figure 4, Fig. 4 is the photoacoustic signal figure of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 1 to test result.As shown in Figure 4, poly-dopamine nanoparticle prepared by the embodiment of the present invention 1 has photoacoustic signal near infrared region, can be used as photoacoustic imaging contrast agent for photoacoustic imaging analysis.
The poly-dopamine nanoparticle of 50 μ g/mL, 75 μ g/mL, 100 μ g/mL, 150 μ g/mL, 200 μ g/mL and 250 μ g/mL is injected respectively to different agar prostheses, according to technique scheme, the agar prosthese that contains poly-dopamine nanoparticle is carried out to photoacoustce signal intensity test test result as shown in Figure 5, Fig. 5 is photoacoustce signal intensity-concentration relationship figure of the poly-dopamine nanoparticle that obtains of the embodiment of the present invention 1.As seen from Figure 5, photoacoustce signal intensity and the concentration of the poly-dopamine nanoparticle of different-grain diameter all have good linear relationship, and linear equation is y=111.76x+3765.59, R
2=0.9999.Therefore,, according to the optoacoustic intensity of poly-dopamine nanoparticle, can carry out the quantitative analysis of photoacoustic imaging.
Poly-dopamine nanoparticle prepared by embodiment 1 injects agar prosthese, be placed in the constant water bath box of 34 ℃, use multispectral photoacoustic imaging system to carry out multispectral scanner, scanning in every 5 seconds 1 time, continue scanning 30min, as shown in Figure 6, Fig. 6 is the photoacoustic signal-time variation diagram of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 1 to test result.As shown in Figure 6, poly-dopamine nanoparticle prepared by embodiment 1 has stable photoacoustic signal, almost there is no the decay of photoacoustic signal within 30min.Generally all there is photobleaching problem in common near-infrared fluorescent molecule, Iimaging Stability is poor, and by comparison, poly-dopamine nanoparticle prepared by the present invention has more stable and excellent imaging effect.
The present invention carries out optoacoustic radiography measure of merit by the poly-dopamine nanoparticle obtaining according to technique scheme, test result as shown in Figure 7, Fig. 7 is that the poly-dopamine nanoparticle prepared of the embodiment of the present invention 1 is at the subcutaneous optoacoustic radiography design sketch of the head of male Balb/C nude mice, the tomoscan profile that wherein solid line is animal, the inner photoacoustic imaging radiography figure for poly-dopamine nanoparticle of dotted line.As seen from Figure 7, poly-dopamine nanoparticle has good radiography effect, clear picture, and contrast is high, is suitable for very much photoacoustic imaging visualization.
The present invention carries out optoacoustic radiography measure of merit by the poly-dopamine nanoparticle obtaining according to technique scheme, test result as shown in Figure 8, Fig. 8 is the optoacoustic radiography design sketch of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 1 at the intestinal of male Balb/C nude mice, wherein, solid line is the tomoscan profile of nude mice intestinal, and dotted line is inner for poly-dopamine nanoparticle is at the photoacoustic imaging radiography figure at mouse intestinal position.As seen from Figure 8, poly-dopamine nanoparticle has good radiography effect to digestion stage property, clear picture, and contrast is high, is suitable for very much photoacoustic imaging visualization.
Embodiment 2
The ammonia that is 28% by 20mL ethanol, 45mL deionized water and 1.5mL mass fraction is placed in 100mL reaction bulb, at 30 ℃, stirs 30min, obtains mixed solvent;
0.2510g dopamine hydrochloride is dissolved in 5mL deionized water, then the aqueous solution of dopamine hydrochloride is added in above-mentioned mixed solvent, lucifuge, at 30 ℃, stir, carry out oxidative polymerization 24h, reaction system, by the colourless light brown that gradually becomes, finally becomes black, and products therefrom obtains poly-dopamine nanoparticle after high speed centrifugation, deionized water wash three times.
The present invention carries out transmission electron microscope observing to poly-dopamine nanoparticle, and as shown in Figure 9, Fig. 9 is the transmission electron microscope picture of the poly-dopamine nanoparticle for preparing of the embodiment of the present invention 2 to observed result.As seen from Figure 9, poly-dopamine nanoparticle is spherical in shape is uniformly distributed, and diameter is between 85nm～150nm.
The present invention carries out dynamic light scattering analysis to poly-dopamine nanoparticle, measures its hydrodynamic radius, and as shown in figure 10, Figure 10 is the dynamic light scattering figure of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 2 to result.As seen from Figure 10, the hydrodynamic radius of poly-dopamine nanoparticle is between 50nm～130nm.
Can be found out by Fig. 9 and Figure 10, the result of the transmission electron microscope gained size of poly-dopamine nanoparticle is slightly less than light scattering result, this is mainly because dynamic light scattering is more responsive for bulky grain, the gathering of a small amount of nanoparticle, or the existence of a small amount of dust all can make test result bigger than normal.
The present invention carries out ultraviolet-visible spectrum test to poly-dopamine nanoparticle, test result as shown in figure 11, Figure 11 is the uv absorption spectra of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 2, as seen from Figure 11, poly-dopamine nanoparticle has absorption within the scope of 600nm～900nm.
The present invention carries out photoacoustic signal spectrum test according to technique scheme to the poly-dopamine nanoparticle of preparation, and as shown in figure 12, Figure 12 is the photoacoustic signal spectrogram of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 2 to test result.As shown in Figure 12, poly-dopamine nanoparticle prepared by the embodiment of the present invention 2 has photoacoustic signal near infrared region, can be used as photoacoustic imaging contrast agent for photoacoustic imaging analysis.
Poly-to 50 μ g/mL, 75 μ g/mL, 100 μ g/mL, 150 μ g/mL, 200 μ g/mL and 250 μ g/mL dopamine nanoparticle is injected respectively to different agar prostheses, according to technique scheme, the agar prosthese that contains poly-dopamine nanoparticle is carried out to photoacoustce signal intensity test test result as shown in figure 13, Figure 13 is the photoacoustce signal intensity-concentration map of the poly-dopamine nanoparticle that obtains of the embodiment of the present invention 2.As seen from Figure 13, photoacoustce signal intensity and the concentration of the poly-dopamine nanoparticle of different-grain diameter all have good linear relationship, and linear equation is y=90.77x+2814.41, R
2=0.9994.Therefore,, according to the optoacoustic intensity of poly-dopamine nanoparticle, can carry out the quantitative analysis of photoacoustic imaging.
Embodiment 3
The ammonia that is 27% by 20mL ethanol, 45mL deionized water and 2.0mL mass fraction is placed in 100mL reaction bulb, at 30 ℃, stirs 30min, obtains mixed solvent;
0.2517g dopamine hydrochloride is dissolved in to 5mL deionized water, then the aqueous solution of dopamine hydrochloride is added in above-mentioned mixed solvent, lucifuge, at 30 ℃, stir, carry out oxidative polymerization 24h, reaction system, by the colourless light brown that gradually becomes, finally becomes black, and products therefrom obtains poly-dopamine nanoparticle after high speed centrifugation, deionized water wash three times.
The present invention carries out transmission electron microscope analysis to the poly-dopamine nanoparticle obtaining, and as shown in figure 14, Figure 14 is the transmission electron microscope picture of the poly-dopamine nanoparticle that obtains of the embodiment of the present invention 3 to result.As seen from Figure 14, spherical in shape being uniformly distributed of poly-dopamine nanoparticle that the embodiment of the present invention 3 prepares, diameter is between 50nm～90nm.
The present invention carries out dynamic light scattering analysis to the poly-dopamine nanoparticle obtaining, and measures its hydrodynamic radius, and as shown in figure 15, Figure 15 is the hydrodynamic radius scattergram of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 3 to result.The hydrodynamic radius of the poly-dopamine nanoparticle that as seen from Figure 15, the embodiment of the present invention 3 obtains is between 30nm～70nm.
Can be found out by Figure 14 and Figure 15, the result of the transmission electron microscope gained size of poly-dopamine nanoparticle is slightly less than light scattering result, this is mainly because dynamic light scattering is more responsive for bulky grain, the gathering of a small amount of nanoparticle, or the existence of a small amount of dust all can make test result bigger than normal.
The poly-dopamine nanoparticle that the present invention obtains carries out ultraviolet-visible spectrum test, and as shown in figure 16, Figure 16 is the uv absorption spectra of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 3 to its uv absorption spectra.As seen from Figure 16, the poly-dopamine nanoparticle that the embodiment of the present invention 3 obtains has absorption within the scope of 600nm～900nm.
The present invention carries out photoacoustic signal spectrum test according to technique scheme to the poly-dopamine nanoparticle of preparation, and as shown in figure 17, Figure 17 is the photoacoustic signal spectrogram of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 3 to test result.As shown in Figure 17, poly-dopamine nanoparticle prepared by the embodiment of the present invention 3 has photoacoustic signal near infrared region, can be used as photoacoustic imaging contrast agent for photoacoustic imaging analysis.
Poly-to 100 μ g/mL, 200 μ g/mL, 300 μ g/mL, 400 μ g/mL, 500 μ g/mL, 600 μ g/mL and 720 μ g/mL dopamine nanoparticle is injected respectively to different agar prostheses, according to technique scheme, the agar prosthese that contains poly-dopamine nanoparticle is carried out to photoacoustce signal intensity test test result as shown in figure 18, Figure 18 is the photoacoustce signal intensity-concentration map of the poly-dopamine nanoparticle that obtains of the embodiment of the present invention 3.As seen from Figure 18, photoacoustce signal intensity and the concentration of the poly-dopamine nanoparticle of different-grain diameter all have good linear relationship, and linear equation is y=30.33x+4631.41, R
2=0.9994.Therefore,, according to the optoacoustic intensity of poly-dopamine nanoparticle, can carry out the quantitative analysis of photoacoustic imaging.
Embodiment 4
The ammonia that the present invention is 26% by 20mL ethanol, 45mL deionized water and 2.5mL mass fraction is placed in 100mL reaction bulb, at 30 ℃, stirs 30min, obtains mixed solvent;
0.2520g dopamine hydrochloride is dissolved in 5mL deionized water, then the aqueous solution of dopamine hydrochloride is added in above-mentioned mixed solvent, lucifuge, at 30 ℃, stir, carry out oxidative polymerization 24h, reaction system, by the colourless light brown that gradually becomes, finally becomes black, and products therefrom obtains poly-dopamine nanoparticle after high speed centrifugation, deionized water wash three times.
The present invention carries out transmission electron microscope analysis to the poly-dopamine nanoparticle obtaining, and as shown in figure 19, Figure 19 is the transmission electron microscope picture of the poly-dopamine nanoparticle that obtains of the embodiment of the present invention 4 to result.As seen from Figure 19, spherical in shape being uniformly distributed of poly-dopamine nanoparticle that the embodiment of the present invention 4 prepares, diameter is between 20nm～70nm.
The present invention carries out dynamic light scattering analysis to the poly-dopamine nanoparticle obtaining, and measures its hydrodynamic radius, and as shown in figure 20, Figure 20 is the hydrodynamic radius scattergram of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 4 to result.As seen from Figure 20, the hydrodynamic radius of poly-dopamine nanoparticle is between 10nm～50nm.
Can be found out by Figure 19 and Figure 20, the poly-transmission electron microscope of dopamine nanoparticle and the result of light scattering, the result of projection Electronic Speculum gained size is slightly less than light scattering result, this is mainly because dynamic light scattering is more responsive for bulky grain, the gathering of a small amount of nanoparticle, or the existence of a small amount of dust all can make test result bigger than normal.
The poly-dopamine nanoparticle that the present invention obtains carries out ultraviolet-visible spectrum test, and as shown in figure 21, Figure 21 is the uv absorption spectra of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 4 to its uv absorption spectra.As seen from Figure 21, the poly-dopamine nanoparticle that the embodiment of the present invention 4 obtains has absorption within the scope of 600nm～900nm.
The present invention carries out photoacoustic signal spectrum test according to technique scheme to the poly-dopamine nanoparticle of preparation, and as shown in figure 22, Figure 22 is the photoacoustic signal spectrogram of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 4 to test result.As shown in Figure 22, poly-dopamine nanoparticle prepared by the embodiment of the present invention 4 has photoacoustic signal near infrared region, can be used as photoacoustic imaging contrast agent for photoacoustic imaging analysis.
Poly-to 250 μ g/mL, 500 μ g/mL, 750 μ g/mL, 1000 μ g/mL, 1250 μ g/mL, 1500 μ g/mL, 1750 μ g/mL, 2000 μ g/mL and 4000 μ g/mL dopamine nanoparticle is injected respectively to different agar prostheses, according to technique scheme, the agar prosthese that contains poly-dopamine nanoparticle is carried out to photoacoustce signal intensity test test result as shown in figure 23, Figure 23 is the photoacoustce signal intensity-concentration map of the poly-dopamine nanoparticle that obtains of the embodiment of the present invention 4.As seen from Figure 23, photoacoustce signal intensity and the concentration of the poly-dopamine nanoparticle of different-grain diameter all have good linear relationship, and linear equation is y=19.76x+15076.17, R
2=0.9935.Therefore,, according to the optoacoustic intensity of poly-dopamine nanoparticle, can carry out the quantitative analysis of photoacoustic imaging.
Embodiment 5
The ammonia that the present invention is 28% by 20mL ethanol, 45mL deionized water and 3.0mL mass fraction is placed in 100mL reaction bulb, at 30 ℃, stirs 30min, obtains mixed solvent;
0.2516g dopamine hydrochloride is dissolved in 5mL deionized water, then the aqueous solution of dopamine hydrochloride is added in above-mentioned mixed solvent, lucifuge, at 30 ℃, stir, carry out oxidative polymerization 24h, reaction system, by the colourless light brown that gradually becomes, finally becomes black, and products therefrom obtains poly-dopamine nanoparticle through deionized water dialysis after three days.
The present invention carries out transmission electron microscope analysis to the poly-dopamine nanoparticle obtaining, and as shown in figure 24, Figure 24 is the transmission electron microscope picture of the poly-dopamine nanoparticle that obtains of the embodiment of the present invention 5 to result.As seen from Figure 24, spherical in shape being uniformly distributed of poly-dopamine nanoparticle that the embodiment of the present invention 5 prepares.
The poly-dopamine nanoparticle that the present invention obtains carries out ultraviolet-visible spectrum test, and as shown in figure 25, Figure 25 is the uv absorption spectra of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 5 to its uv absorption spectra.As seen from Figure 25, the poly-dopamine nanoparticle that the embodiment of the present invention 5 obtains has absorption within the scope of 600nm～900nm.
Embodiment 6
The ammonia that the present invention is 25% by 20mL ethanol, 45mL deionized water and 5.0mL mass fraction is placed in 100mL reaction bulb, at 30 ℃, stirs 30min, obtains mixed solvent;
0.2508g dopamine hydrochloride is dissolved in 5mL deionized water, then the aqueous solution of dopamine hydrochloride is added in above-mentioned mixed solvent, lucifuge, at 30 ℃, stir, carry out oxidative polymerization 24h, reaction system, by the colourless light brown that gradually becomes, finally becomes black, and products therefrom obtains poly-dopamine nanoparticle through deionized water dialysis after three days.
The present invention carries out transmission electron microscope analysis to the poly-dopamine nanoparticle obtaining, and as shown in figure 26, Figure 26 is the transmission electron microscope picture of the poly-dopamine nanoparticle that obtains of the embodiment of the present invention 6 to result.As seen from Figure 26, spherical in shape being uniformly distributed of poly-dopamine nanoparticle that the embodiment of the present invention 6 prepares.
The poly-dopamine nanoparticle that the present invention obtains carries out ultraviolet-visible spectrum test, and as shown in figure 27, Figure 27 is the uv absorption spectra of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 6 to its uv absorption spectra.As seen from Figure 27, the poly-dopamine nanoparticle that the embodiment of the present invention 6 obtains has absorption within the scope of 600nm～900nm.
Embodiment 7
The present invention collects logarithmic (log) phase L929 cell, adjusts cell concentration, inoculates in 96 orifice plates, contains 100 μ L (approximately 104) cell in every hole, after 37 ℃ of cultivation 24h, removes culture fluid;
It is 200mgL that the poly-dopamine nanoparticle of by culture medium being prepared by embodiment 1, embodiment 2, embodiment 3 and embodiment 4 dilutes respectively
-1, 100mgL
-1, 50mgL
-1, 25mgL
-1, 12.5mgL
-1, 6.25mgL
-1the sample of 6 concentration;
Each sample is added to 96 orifice plates, and every hole adds 200 μ L, 6 multiple holes of every kind of concentration;
In 37 ℃, saturated humidity, 5%CO2 cell culture incubator, cultivate 24h;
After 24h, every hole adds the tetrazolium bromide that 20 μ L mass concentrations are 5mg/mL, continues to cultivate 4h;
Stop cultivating, suck culture fluid hole in, every hole adds 150 μ L dimethyl sulfoxide, and low-speed oscillation 10min detects the absorption value of each hole at 492nm place by microplate reader, and conversion obtains the cell survival rate of each concentration.
The relatively cell compatibility of above-mentioned material, result is referring to Figure 28, Figure 28 is the Toxicity test result figure of the poly-dopamine nanoparticle prepared of the embodiment of the present invention 1, embodiment 2, embodiment 3 and embodiment 4 to L929 cell, wherein, A, B, C, D are followed successively by material prepared by embodiment 1, embodiment 2, embodiment 3, embodiment 4 cytotoxicity of L929 cell are investigated to result.As shown in Figure 28, polycaprolactam polyamine nanoparticle has good biocompatibility to cell, can be used as a kind of safe photoacoustic imaging contrast agent.
Embodiment 8
50 of normal male Balb/C mouses (body weight 18g～20g) of raising, be divided at random 5 groups, every group 10, be respectively poly-dopamine nanoparticle prepared by poly-dopamine nanoparticle prepared by poly-dopamine nanoparticle, embodiment 3 prepared by poly-dopamine nanoparticle, embodiment 2 prepared by intravenous injection normal saline, embodiment 1 and embodiment 4, take rabbit body weight as benchmark, injection volume is 5mgkg
-1, the body weight of continuous 10 days monitoring laboratory animals.
The results show: in 10 days without dead mouse; After 10 days, choose at random 3 pathology slice analysis that carry out the heart, liver, spleen, lung, kidney for every group, result proves: compared with matched group (injecting normal saline), the organ of not observing the mouse of poly-dopamine nanoparticle prepared by injection embodiment 1, embodiment 2, embodiment 3 and embodiment 4 has obvious pathology infringement.
Figure 29 is that the body weight of the mouse of the poly-dopamine nanoparticle of injection embodiment 1～4 preparation is schemed over time.In Figure 29, A, B, C, D, E are followed successively by the body weight change of the mouse of poly-dopamine nanoparticle prepared by injecting normal saline, embodiment 1, embodiment 2, embodiment 3, embodiment 4.As shown in Figure 29, all experimental grouies are all without obvious body weight change, and above-mentioned poly-dopamine nanoparticle has good biocompatibility to laboratory animal, can be used as a kind of safe photoacoustic imaging contrast agent.
Comparative example
The present invention adopts 10ugmL
-1graphene oxide carries out ultra-violet absorption spectrum test, and test result is shown in Figure 30, the ultra-violet absorption spectrum comparison diagram of poly-dopamine nanoparticle prepared by the graphene oxide that Figure 30 is comparative example and embodiment 4, and wherein, curve A is 10ugmL
-1the uv absorption spectra of poly-dopamine nanoparticle prepared by embodiment 4, the uv absorption spectra of the graphene oxide that curve B is comparative example.
As seen from Figure 30, the poly-dopamine nanoparticle that prepared by the present invention has stronger uv absorption.
As seen from the above embodiment, the invention provides the application of poly-dopamine nanoparticle.The inventor studies discovery, and poly-dopamine has stronger absorption near infrared region, sets it as photoacoustic imaging contrast agent, has good imaging effect.Experimental result shows: the photoacoustic signal of poly-dopamine nanoparticle is strong, and photoacoustic imaging contrast is high, clear picture.
The above is only the preferred embodiment of the present invention; it should be pointed out that for those skilled in the art, under the premise without departing from the principles of the invention; can also make some improvements and modifications, these improvements and modifications also should be considered as protection scope of the present invention.
Claims (10)
1. poly-dopamine nanoparticle is as the application of photoacoustic imaging contrast agent.
2. application according to claim 1, is characterized in that, the particle diameter of described poly-dopamine nanoparticle is 20nm～230nm.
3. application according to claim 1, is characterized in that, the particle diameter of described poly-dopamine nanoparticle is 50nm～200nm.
4. application according to claim 1, is characterized in that, described in be applied as:
Described poly-dopamine nanoparticle is as photoacoustic imaging contrast agent, the photoacoustic imaging at and intestinal position subcutaneous for head.
5. application according to claim 1, is characterized in that, the preparation method of described poly-dopamine nanoparticle comprises the following steps:
Dopamine hydrochloride is carried out in mixed solvent to oxidative polymerization, obtain poly-dopamine nanoparticle;
Described mixed solvent comprises water, alcohol compound and ammonia.
6. application according to claim 5, is characterized in that, the mass fraction of described ammonia is 25%～28%.
7. application according to claim 5, is characterized in that, the quality of described dopamine hydrochloride and the volume ratio of ammonia are (30～300) mg:1mL.
8. application according to claim 5, is characterized in that, the volume ratio of described water, alcohol compound and ammonia is (15～25): (40～50): (1～5).
9. application according to claim 5, is characterized in that, the temperature of described oxidative polymerization is 15 ℃～35 ℃.
10. application according to claim 5, is characterized in that, the time of described oxidative polymerization is 12h～72h.
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