CN103877574B - Dual phototherapy water-soluble carbon nano composite material and preparation method thereof and application - Google Patents
Dual phototherapy water-soluble carbon nano composite material and preparation method thereof and application Download PDFInfo
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- CN103877574B CN103877574B CN201410066365.4A CN201410066365A CN103877574B CN 103877574 B CN103877574 B CN 103877574B CN 201410066365 A CN201410066365 A CN 201410066365A CN 103877574 B CN103877574 B CN 103877574B
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Abstract
Dual phototherapy water-soluble carbon nano composite material is the π-π planar conjugate complex be made up of without curling Graphene and water soluble metal phthalocyanine single angle or monolayer.Its preparation method comprises, and (1) dissolves water soluble metal phthalocyanine with intermediate water, and being mixed with mass concentration is 10% ~ 15%, adds single angle or monolayer without curling Graphene by 45 ~ 65% of water soluble metal phthalocyanine quality, by Ultrasound Instrument ultrasonic 30 ~ 180 minutes; (2) by centrifugal for above-mentioned obtained dispersion liquid, sucking filtration, washing, drying, to obtain final product.This composite has photo-thermal and OPK double treatment effect under infrared light supply effect, strengthens the killing-efficiency to cancerous cell; Preparation method is easy, a step ultrasonic method had just both solved single angle or the monolayer water solublity without curling Graphene, optical dynamic therapy agent in load again, and uses non-covalent modification, does not destroy the surface characteristic of carbon nano-composite material.
Description
Technical field
The present invention relates to biology medical material technical field, specifically phototherapy agent, more specifically dual phototherapy water-soluble carbon nano composite material and preparation method thereof and application.
Background technology
Phototherapy is a kind of non-invasive therapy technology utilizing visible ray or near infrared light, has the particular advantages such as the high and systemic toxicity of remote-controllable, selectivity is low, is with a wide range of applications in treating malignant tumor.Photo-thermal therapy and optical dynamic therapy are currently widely used in the multi-form phototherapy method of two kinds of oncotherapy.Photo-thermal therapy utilizes photothermal reagent to absorb the light of specific wavelength, is that thermal conductance causes local ambient temperature and raises and irreversibly damage sick cell by non-radiative decay by the Conversion of energy of absorption.Photo-thermal therapy can be improved the hot polymerization collection in photothermal processes and optionally heat the cell of intralesional, thus improves accuracy and the controllability of photo-thermal therapy, can more effectively realize sick cell selective killing.Photodynamic therapy utilizes light-sensitive material to be excited under the illumination of specific wavelength is penetrated, further oxygen molecule in the energy delivery feed solution of photon is produced singlet oxygen, superoxide radical, hydrogen peroxide, and hydroxyl radical free radical isoreactivity oxygenate kind (reactiveoxygenspecies, ROS).ROS produces oxygen pressure to sick cell, thus kills tumor cell, has the specific selectivity be suitable for for diseased region.
Single angle (single-walledcarbonnanohorns, SWCNHs) is the c-based nanomaterial that a class is new, is normally 2 ~ 5nm by diameter, long 30 ~ 50nm, one end open, the pipe composition that the other end is closed with pyramid.Except pattern, size are different from SWCN, single angle does not need to adopt metal as catalyst in preparation, do not have metal residual, therefore bio-toxicity is low.Single angle has near infrared region and absorbs more by force, can absorb photons change into heat by non-radiative decay, and form local light heat effect, killing sick cell, is comparatively ideal photo-thermal therapy agent.But similar to other c-based nanomaterial, carbon nanohorn is water insoluble, is also insoluble to organic solvent.Single angle is applied to biomedical sector, need first solves its water solublity, common way carries out functionalization to its surface.
At present, carbon nanohorn is carried out to the method for functionalization, mainly realized by the method for covalent bond coupling and non-co-bond valence π-π planar conjugate.The method of covalent bond coupling, need to destroy carbon nanohorn original C – C key, the mode adopting covalent bond to combine on this basis, connects functional molecular, reaches the object increasing dissolubility and practical function application.By contrast, non-covalent approach does not need to destroy original structure, utilizes carbon nanohorn existing C – C conjugated structure, selects the molecule having planar conjugate structure, increases water miscible object by π-pi-conjugated functionalization of carrying out to reach.((1)S.Zhu,G.Xu,
Nanoscale,
2010,
2,2538–2549;(2)G.Pagona,A.S.D.Sandanayaka,Y.Araki,JingFan,N.Tagmatarchis,M.Yudasaka,S.Iijima,andO.Ito,
J.Phys.Chem.B,
2006,
110,20729-20732)。
Phthalocyanine is that structure is similar to porphyrin, is the photosensitizer that the second filial generation is applied clinically after porphyrin.Due to optical physics and the spectrochemical property of its excellence, in recent years, phthalocyanine is subject to extensive concern ((1) M.Zhang, T.Murakami in the application of field of photodynamic, K.Ajima, K.Tsuchida, A.S.D.Sandanayaka, O.Ito, S.Iijima, M.Yudasaka
pNAS,
2008,
39, 14773-14778; (2) N.B.R.Vittar, C.G.Prucca, C.Strassert, J.Awruch, V.A.Rivarola,
int.J.Biochem.CellBiol.,
2008,
40, 2192-2205).Phthalocyanine has strong absorption at red light district (650 ~ 770nm), and passes through the life of the metal ion excited triplet state of center coordination, and singlet oxygen productive rate increases.But in aqueous, phthalocyanine is easy to self aggregation and forms dimer, and this greatly reduces its photosensitising efficiency.In use, need suitable carrier, to avoid phthalocyanine self aggregation.At present, the carbonyl reagent that simultaneously can realize the double treatment of photo-thermal therapy and photodynamic therapy is not also had clinically.The work of MinfangZhang etc.: " FabricationofZnPc/proteinnanohornsfordoublephotodynamica ndhyperthermiccancerphototherapy " (M.Zhang, T.Murakami, K.Ajima, K.Tsuchida, A.S.D.Sandanayaka, O.Ito, S.Iijima, M.Yudasaka
pNAS,
2008,
39, 14773-14778; ), be the research work that photo-thermal therapy and photodynamic therapy are combined reported at present.Comprise a few step: (1) initial oxidation carbon nanohorn, destroys its surface characteristic and integrity; (2) logical snperoxiaized hole, loads in nanometer angle by phthalocyanine; (3) carry serum albumin on carbon nanohorn surface, strengthen its water solublity.But preparation method is too complicated, in addition, phthalocyanine is loaded carbon nanohorn inside, do not give full play to the heliosensitivity of phthalocyanine.
Summary of the invention
First object of the present invention is to provide a kind of dual phototherapy water-soluble carbon nano composite material.
Dual phototherapy water-soluble carbon nano composite material of the present invention is the π-π planar conjugate complex be made up of single angle and water soluble metal phthalocyanine, or the π-π planar conjugate complex be made up of without curling Graphene and water soluble metal phthalocyanine monolayer.
Described water soluble metal phthalocyanine is selected from the water-soluble phthalocyanine compound formed by copper, zinc, aluminum or silicon.The phthalocyanine compound of the tetramino preferably formed by copper, zinc, aluminum or silicon or tetrasulfonic acid base.
Another object of the present invention is the defect overcoming prior art, provides a kind of preparation method of simple, easy dual phototherapy water-soluble carbon nano composite material.
The method comprises the steps:
(1) dissolve water soluble metal phthalocyanine with intermediate water, be mixed with the aqueous solution that mass concentration is 10% ~ 15%, add single angle or monolayer without curling Graphene by 45 ~ 65% of water soluble metal phthalocyanine quality, by Ultrasound Instrument ultrasonic 30 ~ 180 minutes;
(2) by centrifugal for above-mentioned obtained dispersion liquid, sucking filtration, washing, drying, dual phototherapy water soluble compound is obtained.
Preferably, step (1), the single angle added or monolayer are 50% of water soluble metal phthalocyanine quality without curling Graphene, and Ultrasound Instrument power is 50 ~ 300W, ultrasonic 60 ~ 120 minutes.
In step (2), during sucking filtration, aperture is adopted to be 180 ~ 250nm microporous filter membrane, colourless to filtrate with intermediate water washing.
In the present invention, its construction unit for single angle (SWNH) or monolayer without curling Graphene for carrier, take water soluble metal phthalocyanine as solubilizing agent, being interacted by π-π between component units forms compound carbon nano-composite material.
The present invention also provides a kind of pharmaceutical composition, and this pharmaceutical composition comprises the pharmaceutically acceptable carrier of at least one and dual phototherapy water-soluble carbon nano composite material of the present invention.
The present invention also provides described dual phototherapy water-soluble carbon nano composite material and aforesaid pharmaceutical composition to treat the application of antitumor drug in preparation.
Here, tumor comprises: cervical cancer, human mouth epidermal carcinoma, breast carcinoma, nasopharyngeal carcinoma, glioblastoma and fibroblastic tumor.
Especially, the present invention is to provide described dual phototherapy water-soluble carbon nano composite material and aforesaid pharmaceutical composition in the application preparing the treatment antitumor drug told under infrared light supply effect.
Dual phototherapy water-soluble carbon nano composite material of the present invention, as photo-thermal and the dual phototherapy agent of optical dynamic therapy, under iraser (650nm ~ 808nm) irradiates, can kill cancerous cell.
Phthalocyanine contains large aromatic conjugated plane, can with π-π effect be firmly adsorbed on there is π system equally single angle or monolayer without on curling Graphene, obtain single angle or the monolayer complex systems without curling Graphene and phthalocyanine.In this compound system, single angle or monolayer not only can stop phthalocyanine self aggregation as carrier without curling Graphene, improve phthalocyanine optical dynamic therapy effect, himself also can be used as the treatment of photo-thermal therapy agent involved in diseases, phthalocyanine then both can improve single angle or the monolayer dissolubility without curling Graphene, himself also has optical dynamic therapy effect, forms effective multifunctional treating system.The multifunctional treating system that this different Therapeutic mode is mutually worked in coordination with or combined, in treatment of diseases, particularly in treatment of cancer, not only can improve therapeutic efficiency, and can reduce bad systemic toxicity and side effect.Therefore, the multifunctional treating system that such photo-thermal is combined with photodynamics is applicable to the Therapeutic Method of light disease therapy by likely becoming a kind of effective cancer etc.
Advantage of the present invention is:
(1) carbon nano-composite material of gained has photo-thermal and OPK double treatment effect simultaneously, strengthens the killing-efficiency to cancerous cell.
(2) preparation method is easy, a step ultrasonic method had just both solved single angle or the monolayer water solublity without curling Graphene, optical dynamic therapy agent in load again, and uses non-covalent modification, does not destroy the surface characteristic of carbon nano-composite material.
Accompanying drawing explanation
Fig. 1 is UV, visible light (UV-Vis) abosrption spectrogram of single angle-phthalocyanine (SWNHs-TSCuPc) complex of preparing of the present invention and free phthalocyanine (TSCuPc).
Detailed description of the invention
preparation embodiment 1
The preparation of water-soluble mono wall carbon nano-tube angle-phthalocyanine complex, as follows:
(1) dissolve tetrasulfonic acid base C.I. Pigment Blue 15 with intermediate water, be mixed with the aqueous solution that mass concentration is 10%, add single angle in the ratio of tetrasulfonic acid base C.I. Pigment Blue 15 and single angle mass ratio 1:0.5, by Ultrasound Instrument ultrasonic 60 minutes.
(2) by centrifugal for above-mentioned obtained mass colour dispersion liquid, to remove bulky grain aggregation, gained liquid aperture 220nm filtering with microporous membrane, and with intermediate water cleaning, until filtrate is colourless, to remove free phthalocyanine.Gained mass colour solid is dispersed in water again, i.e. obtained single angle-phthalocyanine complex, and total concentration is 1.4mg/mL, and wherein, phthalocyanine is 0.49mg/mL, and single angle is 0.91mg/mL.
Gained single angle-phthalocyanine complex can in aqueous systems dispersed and stable existence more than at least 3 months.
preparation embodiment 2
The preparation of water-soluble mono wall carbon nano-tube angle-phthalocyanine complex, as follows:
(1) dissolve tetrasulfonic acid base aluminum phthalocyanine with intermediate water, be mixed with the aqueous solution that mass concentration is 12%, add single angle in the ratio of tetrasulfonic acid base aluminum phthalocyanine and single angle mass ratio 1:0.5, by Ultrasound Instrument ultrasonic 60 minutes.
(2) by centrifugal for above-mentioned obtained dispersion liquid, to remove bulky grain aggregation, gained liquid aperture 220nm filtering with microporous membrane, and with intermediate water cleaning, until filtrate is colourless, to remove free phthalocyanine.Drying i.e. obtained single angle-phthalocyanine complex.
preparation embodiment 3
Water solublity monolayer without the preparation of curling Graphene-phthalocyanine complex, as follows:
(1) dissolve tetrasulfonic acid base C.I. Pigment Blue 15 with intermediate water, be mixed with the aqueous solution that mass concentration is 15%, add monolayer without curling Graphene in tetrasulfonic acid base C.I. Pigment Blue 15 and monolayer without the ratio of curling Graphene mass ratio 1:0.5, by Ultrasound Instrument ultrasonic 60 minutes.
(2) by centrifugal for above-mentioned obtained dispersion liquid, to remove bulky grain aggregation, gained liquid aperture 200nm filtering with microporous membrane, and with intermediate water cleaning, until filtrate is colourless, to remove free phthalocyanine.Drying i.e. obtained monolayer is without curling Graphene-phthalocyanine complex.
preparation embodiment 4
The preparation of water-soluble mono wall carbon nano-tube angle-phthalocyanine complex, as follows:
(1) dissolve tetramino silicon phthalocyanine with intermediate water, be mixed with the aqueous solution that mass concentration is 14%, add single angle in the ratio of tetramino silicon phthalocyanine and single angle mass ratio 1:0.5, by Ultrasound Instrument ultrasonic 160 minutes.
(2) by centrifugal for above-mentioned obtained dispersion liquid, gained liquid aperture 220nm filtering with microporous membrane, and with intermediate water cleaning, until filtrate is colourless, to remove free phthalocyanine.Drying i.e. obtained single angle-phthalocyanine complex.
testing example 1
Experimental technique is as follows:
(1) the single angle-phthalocyanine composite solution intermediate water of preparation embodiment 1 gained being prepared phthalocyanine concentration is 10 μ g/mL, gets 1 milliliter in Specimen bottle, at 650nm laser (3Wcm
-2) under irradiation, change by the color of thermal imaging system recording solution, the also variations in temperature of ie in solution.
Along with the increase of light application time, the temperature of single angle-phthalocyanine complex solution also significantly raises, and increases 33 DEG C in 6 minutes.Confirm that single angle-phthalocyanine complex solution has good photo-thermal effect.
(2) with 5, it is trapping agent that 5-dimethyl-1-is oxidized pyrrolin solution (DMPO), prepares the single angle-phthalocyanine complex solution of embodiment 1 gained at 650nm laser (3Wcm by electron paramagnetic resonance (EPR) technology for detection
-2) irradiate the lower Free Radical Signal produced.
At 650nm laser (3Wcm
-2) under irradiation, hydroxy radical signal detected, confirm that single angle-phthalocyanine complex has photodynamic effect.
In addition, the phthalocyanine of Fig. 1 instruction book wall carbon nano-tube angle-phthalocyanine complex specific ionization has larger absorption value under UV, visible light (UV-Vis).
application Example 1
Single angle-phthalocyanine complex prepared by preparation embodiment 1 is as photo-thermal and optical dynamic therapy agent, and its cell in vitro method of testing is as follows:
Configuration concentration is 50,100 respectively, the single angle-phthalocyanine complex solution of 150 μ g/mL.Human cervical carcinoma cell (HeLa cell) is in 96 orifice plates (every hole 10
4individual cell) in cultivate after 24 hours, add the single angle-phthalocyanine complex solution of prepared series concentration, cultivate 24 hours, with 650nm laser (3W/cm
2) irradiate 3 ~ 8min, then cultivate 24 hours, survey cell survival rate with MTT method.
At 650nm laser (3W/cm
2) under illuminate condition, can 70% ~ 85% be reached to the kill ratio of cell.Confirm that single angle-phthalocyanine complex is this and combine photo-thermal and OPK multifunctional treating system has good kill ratio to human cervical carcinoma cell.
application Example 2
Single angle-phthalocyanine complex prepared by preparation embodiment 1 is as photo-thermal and optical dynamic therapy agent, and in its body, nude mice method of testing is as follows:
Human mouth epidermal carcinoma cell subcutaneous transplantation in nude mouse, cultivate 6 ~ 7 days.Intravenous injection 200 μ L single angle-phthalocyanine complex solution is in nude mouse, and every day is with 650nm laser (3W/cm subsequently
2) irradiate tumor locus 10 minutes, prolonged exposure 10 days.
Laser irradiates the growth of obvious inhibition tumor cell, and gross tumor volume is reducing with macroscopic speed.Prolonged exposure is after 10 days, tumor disappearance.Confirm that single angle-phthalocyanine complex effectively can kill human mouth epidermal carcinoma tumor cell in body.
application Example 3
The method of Application Example 1,2 is applied to breast carcinoma, nasopharyngeal carcinoma, glioblastoma, fibroblastic tumor, and the effect of testing under the same terms is also close.Under Application Example 1 condition, be 70% ~ 90% to cell kill ratio; Under Application Example 2 condition, tumor disappearance.
application Example 4
Adopt the method for Application Example 1,2,3, adopt other wavelength to be greater than the infrared of 650nm and near infrared laser (650nm ~ 808nm), in this wave-length coverage, when other are consistent, experiment effect is also close.Under Application Example 1 condition, be 60% ~ 90% to cell kill ratio; Under Application Example 2 condition, tumor disappearance.
The present invention confirms, in preparation method, all water soluble metal phthalocyanines are all applicable, and to all water soluble metal phthalocyanines, preparation method is the same.In application, if metal phthalocyanine, be then that the phthalocyanine active oxygen productive rate under suitable central metal (as copper, zinc, aluminum, silicon etc.) exists is high, be applicable to optical dynamic therapy.Centered by zinc, aluminum, silicon, the phthalocyanine of atom is all well for the photosensitizer of optical dynamic therapy.The generation of central metal element to active oxygen has certain influence.
Claims (9)
1. dual phototherapy water-soluble carbon nano composite material, it is characterized in that: be the π-π planar conjugate complex be made up of single angle and water soluble metal phthalocyanine, or the π-π planar conjugate complex be made up of without curling Graphene and water soluble metal phthalocyanine monolayer;
Described water soluble metal phthalocyanine is selected from the water-soluble phthalocyanine compound formed by copper, zinc, aluminum or silicon.
2. dual phototherapy water-soluble carbon nano composite material according to claim 1, is characterized in that: described water soluble metal phthalocyanine is selected from the phthalocyanine compound of tetramino or the tetrasulfonic acid base formed by copper, zinc, aluminum or silicon.
3. the preparation method of dual phototherapy water-soluble carbon nano composite material as claimed in claim 1, is characterized in that: comprise the steps:
(1) dissolve water soluble metal phthalocyanine with intermediate water, be mixed with the aqueous solution that mass concentration is 10% ~ 15%, add single angle or monolayer without curling Graphene by 45 ~ 65% of water soluble metal phthalocyanine quality, by Ultrasound Instrument ultrasonic 30 ~ 180 minutes;
(2) by centrifugal for above-mentioned obtained dispersion liquid, sucking filtration, washing, drying, dual phototherapy water soluble compound is obtained.
4. preparation method as claimed in claim 3, is characterized in that: in step (1), and the single angle added or monolayer are 50% of water soluble metal phthalocyanine quality without curling Graphene, and Ultrasound Instrument power is 50 ~ 300W, ultrasonic 60 ~ 120 minutes.
5. preparation method as claimed in claim 3, is characterized in that: in step (2), adopts aperture to be 180 ~ 250nm microporous filter membrane during sucking filtration, colourless to filtrate with intermediate water washing.
6. a pharmaceutical composition, comprises the pharmaceutically acceptable carrier of at least one and dual phototherapy water-soluble carbon nano composite material as claimed in claim 1.
7. dual phototherapy water-soluble carbon nano composite material as claimed in claim 1 or pharmaceutical composition according to claim 6 treat the application of antitumor drug in preparation.
8. apply as claimed in claim 7, it is characterized in that: tumor comprises: cervical cancer, human mouth epidermal carcinoma, breast carcinoma, nasopharyngeal carcinoma, glioblastoma and fibroblastic tumor.
9. apply as claimed in claim 7, it is characterized in that: preparing the application of the treatment antitumor drug told under infrared light supply effect.
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| CN105968118B (en) * | 2016-05-23 | 2018-03-30 | 上海师范大学 | A kind of phthalocyanine complex of iridium and its preparation method and application |
| US10852264B2 (en) | 2017-07-18 | 2020-12-01 | Boston Scientific Scimed, Inc. | Systems and methods for analyte sensing in physiological gas samples |
| 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 |
| US11079371B2 (en) | 2018-02-20 | 2021-08-03 | Boston Scientific Scimed, Inc. | Chemical sensors with non-covalent surface modification of graphene |
| CN112041672B (en) | 2018-04-25 | 2024-02-27 | 明尼苏达大学董事会 | Graphene non-covalent and electrostatic surface modified chemical varactor-based sensor |
| CN109232906A (en) * | 2018-09-20 | 2019-01-18 | 福建师范大学 | Polyfluoroalkyl axial substituted silicon (IV) phthalocyanine-carbon nanotube supramolecular system and the preparation method and application thereof |
| WO2020112825A1 (en) | 2018-11-27 | 2020-06-04 | Boston Scientific Scimed, Inc. | Systems and methods for detecting a health condition |
| WO2020131567A1 (en) | 2018-12-18 | 2020-06-25 | Boston Scientific Scimed, Inc. | Systems and methods for measuring kinetic response of chemical sensor elements |
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