CN102284063A - Application of carbon nanotube-chitosan-phycocyanin compound in preparing antineoplastic drugs - Google Patents
Application of carbon nanotube-chitosan-phycocyanin compound in preparing antineoplastic drugs Download PDFInfo
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- CN102284063A CN102284063A CN 201110234942 CN201110234942A CN102284063A CN 102284063 A CN102284063 A CN 102284063A CN 201110234942 CN201110234942 CN 201110234942 CN 201110234942 A CN201110234942 A CN 201110234942A CN 102284063 A CN102284063 A CN 102284063A
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Abstract
The invention provides application of a carbon nanotube-chitosan-phycocyanin compound in preparing antineoplastic drugs. The carbon nanotube-chitosan-phycocyanin compound is formed by combining multiwall carbon nanotubes, water-soluble chitosan and spirulina phycocyanin in a non-covalent way. The carbon nanotube-chitosan-phycocyanin compound has favorable functions of inhibiting growth of mammary cancer MCF-7 cells and liver cancer HepG2 cells, and especially has stronger functions of inhibiting tumor cells and killing tumor cells under the irradiation of near-infrared light and visible light. The carbon nanotube-chitosan-phycocyanin compound provided by the invention has wide prospects in photodynamic treatment and photo-thermal treatment of tumor cells when being used as an anti-tumor biomedical material.
Description
Technical field
The present invention relates to the application of phycocyanin complex, be specifically related to the application of CNT-chitosan-phycocyanin complex in the preparation antitumor drug.
Background technology
In the cyanophyceae cell, (Phycocyanin is the ubiquitous biliproteins of a class PC) to phycocyanin, is a kind of special chromoprotein.Studies show that phycocyanin has notable antitumor activity, have the raising lymphocyte activity, the diseases prevention of enhancing body, resistance against diseases.Phycocyanin has characteristic absorption peak at wavelength 280nm, 360nm and 620nm place.Can produce lethal effect outside the light kinetoplast to human cancer cell external.
(carbon nanotube CNT) has unique nido assize China ink alkene structure to CNT, and diameter changes to the hundreds of nanometer from several nanometers, and length also can change to several microns from several nanometers.CNT can discharge a large amount of vibrational energies after the near infrared spectrum radiation.Because these energy that discharged can make tissue produce amount of localized heat, thereby make CNT have the potentiality that possibility is applied to treatment of cancer.Because of body tissue lacks the chromophore that absorbs near infrared spectrum, so near infrared light can penetrate body tissue, and the influence small to its generation.With SWCN (singlewalled carbon nanotube, SWNT) compare, multi-walled carbon nano-tubes (multi-wall carbon nanotube, MWCNT) can absorb more near infrared light, have more effective electrons because MWNT unit absorbs microgranule, and the CNT of unit mass has more metal catheter.The bunchy but CNT is reunited easily, water dispersible and biocompatibility are relatively poor. chitosan (chitosan, CS) be to obtain through deacetylation by the chitin (chitin) that nature extensively exists, chemical name is polydextrose amine (1-4)-2-amino-B-D glucose. chitosan can be generated natural metabolite by biological intravital lysozyme degraded, have characteristics nontoxic, that can be absorbed fully by organism, therefore have bigger superiority as pharmaceutical carrier with it.Water-soluble chitosan is to make through the carboxylation modification from chitosan, and is soluble in water, stable in properties, and the chitosan-modified CNT with having good biocompatibility can improve CNT water dispersible and biocompatibility.
(Photodynamic Therapy PDT) is a kind of new technique of treatment tumor to optical dynamic therapy.Its process is, at first the tumor tissues selectivity absorbs photosensitizer, and be stored in it, after suitable wavelength light local irradiation, photosensitizer is activated subsequently, and the photosensitizer of excited state is given oxygen on every side energy delivery, generate active very strong singlet oxygen, singlet oxygen and adjacent biomacromolecule generation oxidation reaction produce cytotoxic effect, and then cause cell impaired and even dead.(Photothermal Therapy PTT) is to use and has the good laser of penetrance (using infrared light usually) and optionally shine tumor tissues photo-thermal therapy, makes tissue produce photo-thermal, and temperature raises, and causes cell death.Therefore, new and effective existing optical dynamic therapy has the biomedical material of photo-thermal therapy prospect significant in oncotherapy again.
Summary of the invention
Be defective and the deficiency that overcomes above-mentioned correlation technique, the application of expanding phycocyanin simultaneously the invention provides the application of CNT-chitosan-phycocyanin complex in the preparation antitumor drug.
CNT-chitosan of the present invention-phycocyanin complex (MWCNT-CS-PC) is by the carboxylation CNT, by water-soluble chitosan non-covalent modification CNT, prepare water miscible multi-walled carbon nano-tubes-chitosan (MWCNT-CS) nanoparticle, and on this basis complex is obtained with highly purified Spirulina phycocyanin coupling again, its concrete preparation technology is as follows:
(1) carboxylated multi-walled carbon nano-tubes is dispersed in the phosphate buffer, after 30 minutes～90 minutes, adds water-soluble chitosan through sonic oscillation again, sonic oscillation also stirs, and gets mixed solution; Standing demix then, with the upper strata liquid centrifugalize after the layering, the upper strata liquid that obtains is chitosan-modified water-soluble multi-wall carbon nanotube solution; The mass ratio of described carboxylated multi-walled carbon nano-tubes and water-soluble chitosan is 1:1～1:10;
(2) in the water-soluble multi-wall carbon nanotube solution that step (1) obtains, add carbodiimide hydrochloride that is equivalent to 1～5 times of carboxylated multi-walled carbon nano-tubes quality and the N-hydroxy-succinamide that is equivalent to 1～6 times of carboxylated multi-walled carbon nano-tubes quality, under the lucifuge condition, add the phycocyanin powder, in 10 ℃～25 ℃ constant temperature vibrations 8 hours～15 hours; The back solution that will vibrate filters, and the gained filter cake is CNT-chitosan-phycocyanin complex; The mass ratio of described phycocyanin powder and carboxylated multi-walled carbon nano-tubes is 1:1～1:10.
The described carboxylated multi-walled carbon nano-tubes purity of step (1) is 90% ~ 99%, and diameter is 10 nm～20nm, and length is 0.5 μ m～2 μ m, carboxylation rate: 1wt%～10 wt%(weight percents).
The carboxylation degree of above-mentioned water-soluble chitosan is 0.1%～1%, and molecular weight is 500～10000.
Above-mentioned phycocyanin purity is 4.0～6.0 (A620/A280 is at the ratios of wavelength 620nm with the absorbance of 280nm).
Above-mentioned phosphate buffer is sodium phosphate buffer or 2mM～5mM(mM) kaliumphosphate buffer.
After the vibration that step (2) obtains mixed liquor to adopt molecular weight be 10kD～100kD(kilodalton) the ultrafiltration of ultrafiltration pipe.
The optical dynamic therapy potentiality that both had phycocyanin by the stable CNT-chitosan of above-mentioned prepared-phycocyanin complex, the photo-thermal therapy potentiality that have CNT again, and modify by introducing water-soluble chitosan, increased the biocompatibility of this complex.
The present invention tests by in vitro study, and the application of CNT-chitosan-phycocyanin complex in the preparation antitumor drug is provided.
The computing formula of cell inhibitory rate and cell survival rate is as follows:
Cell inhibitory rate (%)=(1-test group OD490 value/matched group OD570 value) * 100% (1)
Test group OD490
Cell survival rate (%)=------* 100% (2)
Matched group OD490
In vitro study of the present invention comprises that growth of tumour cell suppresses two parts under growth of tumour cell inhibition and the laser irradiation.It is with the tumor cell cultivation of going down to posterity in containing the DMEM complete culture solution of hyclone that growth of tumour cell suppresses, and then be inoculated in the cultivation of 96 well culture plates to remove original culture medium, and then adding does not contain the high sugared DMEM complete medium of calf serum, add CNT-chitosan-phycocyanin complex then, regulate the concentration of the complex that adds, as negative control group, calculate cell inhibitory rate and cell survival rate with the cultivation group that do not add this complex according to above-mentioned two formula.
To suppress be with the tumor cell cultivation of going down to posterity in containing the DMEM complete culture solution of hyclone to growth of tumour cell under the laser irradiation, and then be inoculated in the cultivation of 96 well culture plates to remove original culture medium, add the fresh high sugared DMEM complete medium that does not contain calf serum again, add above-mentioned complex then, with the liquid medium hole that do not add described complex as negative control group, after cultivating certain hour respectively, liquid medium washs with PBS, in remaining liquid medium, add fresh low sugar DMEM complete medium, adopt 808nm or 532nm laser irradiation culture hole, remove irradiation bomb and continue to cultivate certain hour afterwards.Carry out the calculating of cell inhibitory rate and survival rate according to above-mentioned formula equally.
Results of in vitro studies shows, this complex has good growth inhibited effect to the breast carcinoma MCF-7 cell and the hepatocarcinoma HepG2 cell of In vitro culture, especially under near infrared light and visible light radiation, inhibitory action is further strengthened, all present the feature of killing tumor cell, CNT-chitosan provided by the invention-phycocyanin complex can be used as the preparation anti-tumor drug.
The invention has the advantages that:
(1) the carbon nano-tube modified water-soluble and the biocompatibility that will improve complex of water-soluble chitosan and phycocyanin;
(2) CNT-chitosan-phycocyanin complex all has the feature of killing tumor cell under near infrared light and visible light radiation.
Description of drawings
Fig. 1 is prepared meso sample MWCNT-CS of multi-walled carbon nano-tubes MWCNT and embodiment 1 and the infrared spectrum of product MWCNT-CS-PC.
The specific embodiment
The present invention is described in further detail below in conjunction with the specific embodiment, but the specific embodiment to should not be construed as be qualification to protection domain of the present invention.
Breast carcinoma MCF-7 cell that each embodiment adopted and hepatocarcinoma HepG2 cell derive from Zhongshan University medical college experimental center.
Embodiment 1The preparation of CNT-chitosan-phycocyanin complex (MWCNT-CS-PC)
(1) takes by weighing the carboxylic carbon nano-tube powder that the 40mg diameter is 10nm (the carboxylation rate is 1wt%), add in the 150ml 5mM PBS solution, ultra-sonic dispersion 60 minutes adds 170mg water-soluble chitosan CS then, continued sonic oscillation 60 minutes, ultrasonic back was to mixed solution magnetic agitation 1 hour.Behind the standing demix 6 hours, get supernatant liquid high speed centrifugation under the rotating speed of 10000r/min, the upper strata liquid after centrifugal is meso sample: chitosan-modified water-soluble multi-wall carbon nanotube uniform solution (MWCNT-CS).Adopt the ultrafiltration pipe ultrafiltration of 30kD to remove CS more than needed among the MWCNT-CS, with the lyophilization of gained filter cake, as the sample of phenetic analysis;
(2) under stirring condition, in the water-soluble multi-wall carbon nanotube solution that makes, add 70mg carbodiimide hydrochloride (EDC-HCl) and 160mgN-N-Hydroxysuccinimide (NHS), lucifuge continues to stir 30 minutes, under the lucifuge condition, add 35mg high-purity PC powder, in 20 ℃ of constant temperature vibration 15h.Vibration back solution adopts the ultrafiltration pipe ultrafiltration of 80kD to remove unnecessary PC, EDC-HCl and NHS.The gained filter cake is CNT-chitosan-phycocyanin composite sample (MWCNT-CS-PC), and the sample lyophilization is used for phenetic analysis.
The sample of step (1) and (2) gained carries out infrared spectrum (FTIR) analysis, adopt the Nexus670 type Fourier transform infrared spectroscopy scanner of U.S. Thermo Nicolet company, powder sample grinds compacting in flakes with potassium bromide after intensive drying, then made sheet is carried out sweep test in instrument is put in baking under the infrared lamp after 30 minutes sample room.As shown in Figure 1.MWCNT is at 1712cm
-1, 3461cm
-1Absworption peak appears in the place, corresponds respectively to carboxyl and hydroxyl, shows that the carboxylation carbon nano tube surface of being bought has carboxylic acid (COOH) and carboxylate radical (COO-) group.These active groups all are hydrophilic radicals, help MWCNT to be dispersed in the aqueous solution, and these functional groups will provide the microenvironment of a static reaction for CS non-covalent modification MWNT simultaneously.
CS is the product of chitin behind deacetylation, and the amino of a high reaction activity is arranged on its construction unit, can introduce other functional groups easily.In the infrared spectrum of MWCNT-CS, the characteristic absorption peak of visible CS.Be positioned at 1650cm
-1The peak be the C=O vibration absorption peak; Be positioned at 1080cm
-1The peak be bridged ring C-O-C vibration absorption peak, 1520cm
-1The peak be N-H degeneration vibration peak; Be positioned at 1126cm
-1The peak be the eigen vibration peak of glycosidic bond.Be positioned at 3460cm
-1The peak be the O-H stretching vibration peak, peak intensity is apparently higher than MWCNT herein; The infrared spectrum of MWCNT-CS and MWCNT is compared, finds that the absworption peak of MWCNT among the MWCNT-CS has part to disappear totally, this main because INFRARED ABSORPTION of MWCNT relatively a little less than, be absorbed stronger CS absorb cover.What this showed the CS success is wrapped in the MWCNT surface.
Phycocyanin C-PC is at 533cm
-1, 1654cm
-1, 3441cm
-1Near bigger infrared absorption peak is arranged, the infrared spectrum of MWCNT-CS-PC shows, at 533cm
-1, 1654cm
-1, 3441cm
-1Near significantly absworption peak is also arranged, have MWCNT, CS and PC characteristic of correspondence ultrared spectrum peak separately as can be seen in the phycocyanin complex of this preparation.Experimental result shows and has finally prepared the multi-walled carbon nano-tubes that is loaded with phycocyanin, i.e. MWCNT-CS-PC.
Embodiment 2
(1) growth of tumour cell suppresses
Analyze the growth inhibited effect of complex by the MTT colorimetry to tumor cell.
The breast carcinoma MCF-7 cell and the hepatocarcinoma HepG2 cell strain of recovery are placed the DMEM complete culture solution that contains 10% hyclone, in 37 ℃, 5%CO
2The cultivation of going down to posterity under incubator, the saturated humidity condition.Respectively with cell concentration 3 * 10
3/ 100 μ L are inoculated in 96 well culture plates with 2 kinds of cancerous cell, every hole 200 μ l.In 37 ℃, 5% CO
2Leave standstill in the incubator and cultivate 24h to remove original culture medium, add the fresh high sugared DMEM complete medium that does not contain calf serum of 100 μ L again, add the prepared MWCNT-CS-PC of embodiment 1 again, its concentration is respectively 30,60,90,120,150(μ g/mL), with the liquid medium hole that do not add MWCNT-CS-PC as negative control group, after cultivating 24 hours respectively, all use phosphate buffer (PBS) washed twice; Add 20 μ L5mg.mL again
-1MTT liquid, continue to cultivate 4h, obtain the bluish violet crystallization; And then adding 100uL dimethyl sulfoxide (DMSO), 10 min that vibrate fully dissolve the bluish violet crystallization.
Different MWCNT-CS-PC concentration (abbreviating drug level as) to the tumor cell survival rate to influence data as shown in table 1.As can be seen from Table 1, the MWCNT-CS-PC concentration of being added is big more, and its influence to the tumor cell survival rate is big more, and the tumor cell survival rate is low more.
Table 1
Annotate: * p＜0.05, * * p＜0.01 (t check).
(2) growth of tumour cell suppresses under the laser irradiation
Press cell concentration 3 * 10 respectively
3/ 100 μ L are inoculated in 96 well culture plates with above-mentioned 2 kinds of cancerous cell, every hole 200 μ l.In 37 ℃, 5%CO
2Leave standstill in the incubator and cultivate 24h to remove original culture medium, add the fresh high sugared DMEM complete medium that does not contain calf serum of 100 μ L again, add the prepared MWCNT-CS-PC of embodiment 1 again, its concentration is 60 μ g/mL, with the liquid medium hole that do not add MWCNT-CS-PC as negative control group, after cultivating 12 hours respectively, use the PBS washed twice; Add again and add fresh low sugar DMEM complete medium in the cultivation group of complex and the negative control group group, adopt 808nm or 532nm laser irradiation culture hole after 60 seconds, 120 seconds, 180 seconds, 240 seconds, 300 seconds, continue again to cultivate 12 hours, add 20 μ L5mg.L then
-1MTT liquid, continue to cultivate 4h, obtain the bluish violet crystallization, and then add 100uL DMSO, vibration 10min fully dissolves the bluish violet crystallization.
Measure optical density value with enzyme-linked immunosorbent assay instrument, above-mentioned two formula of cell inhibitory rate and survival rate calculate.
The cultivation group that is added with MWCNT-CS-PC is under 808nm laser irradiation, and different exposure times are as shown in table 2 to the influence of tumor cell survival rate, and exposure time is long more, and the tumor cell survival rate is low more, and especially the MCF-7 cell survival rate is more lower.Further experiment is found, if only with 808nm laser irradiation negative control group, the MCF-7 cell survival rate is 93%, the HepG-2 cell survival rate is 95%, cell survival rate does not have obvious influence, cell survival rate result when the no laser irradiation is approaching with the cultivation group that is added with MWCNT-CS-PC, illustrate added MWCNT-CS-PC (60 μ g/mL) the cultivation group under laser irradiation to the influence of tumor cell survival owing to MWCNT-CS-PC causes, rather than cause by laser irradiation.
Table 2
Annotate: * p＜0.05, * * p＜0.01 (t check).
The cultivation group that is added with MWCNT-CS-PC is under 532nm laser irradiation, and different exposure times are as shown in table 3 to the influence of tumor cell survival rate.Further experiment is found, if with 532nm laser irradiation negative control group, the MCF-7 cell survival rate is 93%, the HepG-2 cell survival rate is 95%, cell survival rate does not have significant change, cell survival rate result when the no laser irradiation is approaching with the cultivation group that is added with MWCNT-CS-PC, the cultivation group that same explanation has added MWCNT-CS-PC (60 μ g/mL) under laser irradiation to the influence of tumor cell survival owing to MWCNT-CS-PC causes, rather than cause by laser irradiation.
Table 3
Annotate: * p＜0.0, * * p＜0.01 (t check).
Claims (1)
1. the application of CNT-chitosan-phycocyanin complex in the preparation antitumor drug.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102846553A (en) * | 2012-08-31 | 2013-01-02 | 华南理工大学 | Preparation method for chlorella polypeptide-chitosan nanoparticle |
| CN104667289A (en) * | 2014-01-28 | 2015-06-03 | 暨南大学 | Antitumor drug carrier and application method thereof |
| CN107261142A (en) * | 2017-06-05 | 2017-10-20 | 东华大学 | It is a kind of for porous filamentous nanocarbon base load medicine photothermal reagent of oncotherapy and preparation method thereof |
| CN107892290A (en) * | 2017-12-13 | 2018-04-10 | 西安医学院 | A kind of preparation method and applications of PEOz modifications single-walled carbon nanotube |
| CN108096578A (en) * | 2017-12-30 | 2018-06-01 | 广西师范大学 | The preparation method and applications of carbon nanohorn/phycocyanin nano-complex |
| CN113797356A (en) * | 2020-06-17 | 2021-12-17 | 广东量子墨滴生物科技有限公司 | Carbon nano composite biological preparation, preparation method and application |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102274510A (en) * | 2011-07-15 | 2011-12-14 | 华南理工大学 | Preparation method of carbon nanotube-chitosan-phycocyanin nanoparticles |
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| CN102274510A (en) * | 2011-07-15 | 2011-12-14 | 华南理工大学 | Preparation method of carbon nanotube-chitosan-phycocyanin nanoparticles |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102846553A (en) * | 2012-08-31 | 2013-01-02 | 华南理工大学 | Preparation method for chlorella polypeptide-chitosan nanoparticle |
| CN102846553B (en) * | 2012-08-31 | 2014-04-02 | 华南理工大学 | Preparation method for chlorella polypeptide-chitosan nanoparticle |
| CN104667289A (en) * | 2014-01-28 | 2015-06-03 | 暨南大学 | Antitumor drug carrier and application method thereof |
| CN107261142A (en) * | 2017-06-05 | 2017-10-20 | 东华大学 | It is a kind of for porous filamentous nanocarbon base load medicine photothermal reagent of oncotherapy and preparation method thereof |
| CN107261142B (en) * | 2017-06-05 | 2021-06-04 | 东华大学 | Porous carbon nanofiber-based drug-loaded photothermal reagent for tumor treatment and preparation method thereof |
| CN107892290A (en) * | 2017-12-13 | 2018-04-10 | 西安医学院 | A kind of preparation method and applications of PEOz modifications single-walled carbon nanotube |
| CN107892290B (en) * | 2017-12-13 | 2020-09-22 | 西安医学院 | Preparation method and application of PEOz modified single-walled carbon nanotube |
| CN108096578A (en) * | 2017-12-30 | 2018-06-01 | 广西师范大学 | The preparation method and applications of carbon nanohorn/phycocyanin nano-complex |
| CN113797356A (en) * | 2020-06-17 | 2021-12-17 | 广东量子墨滴生物科技有限公司 | Carbon nano composite biological preparation, preparation method and application |
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