CN103536918A - Phthalocyanine-quantum dot novel photosensitizer and preparation method thereof - Google Patents
Phthalocyanine-quantum dot novel photosensitizer and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a phthalocyanine-quantum dot novel photosensitizer and a preparation method thereof. The phthalocyanine-quantum dot novel photosensitizer is a system composed of a phthalocyanine solution and a CdTe quantum dot solution. Under the condition of two-photon excitation, the phthalocyanine-quantum dot novel photosensitizer has fluorescence resonance energy transfer properties, and has the optimal compounding concentration, the optimal excitation power and the optimal fluorescence resonance energy transfer efficiency. The phthalocyanine-quantum dot novel photosensitizer has a certain practical significance in the bioscience field and especially in two-photon photodynamic therapy use.
Description
Technical field
The present invention relates to the interdisciplinary fields such as chemistry, physics and material science, more specifically relate to a kind of phthalocyanine-quantum dot novel photosensitive agent and preparation method thereof.
Background technology
Development along with modern science and technology, at high-technology field, the demand of Functional dye is strengthened day by day, the application of phthalocyanine and compound thereof has not only been confined to the aspects such as pigment, ink and catalyst, phthalocyanine-like compound, with special natures such as its unique photochemistry, optical physics, nonlinear opticses, is developed rapidly and become " Functional dye ".The kind of phthalocyanine and compound thereof has a lot, as ZnPc, iron-phthalocyanine, magnesium phthalocyanine, C.I. Pigment Blue 15 etc.Phthalocyanines dye is also widely used in cell marking, but its fluorescence lifetime is short, and photobleaching easily occurs.
Since 20th century the eighties be applied to for the first time clinically, photodynamic therapy (PDT) becomes a kind of novel therapies after chemotherapy, surgical operation and radiation therapy.It is a kind of Photosensitive reaction of following biological effect being participated in by oxygen molecule.Its process is, the photosensitizer that the laser irradiation of specific wavelength absorbs pathological tissues selectivity is excited, and the photosensitizer of excited state is given oxygen around 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.Due to molecular biology and laser technology and the development that utilizes fiber-optic transfer signalling technique, photodynamic therapy has been widely used in the disease that clinical treatment kinds of tumors, ophthalmology and skin are relevant.The advantage of photodynamic therapy is: toxicity is little, produce effects fast, repeated application can not produce drug resistance.Selectivity to tumor is high, does not jeopardize normal structure when killing tumor.
Fig. 1 has shown PDT treatment principle process.The existence of three kinds of materials of this process need: photosensitizer, light and oxygen, wherein the most key is the selection of photosensitizer, it is the core substance of optical dynamic therapy.First photosensitizer is imported in live body or tumor tissues, through after a period of time, photosensitizer selective aggregation is in tumor tissues, and concentration is higher; And photosensitizer in normal structure is by metabolism or discharge, concentration is very low; Then, with the light of certain wavelength, tumor locus is carried out to elective irradiation, in the presence of oxygen, by a series of optical physicss, photochemistry and molecular biology process, the active oxygen that generation is harmful to target cell, makes the biomolecule oxygen inactivation in tumor tissues, damage tumor cell.
The photosensitizer of preparing for traditional one-photon excitation, the FRET (fluorescence resonance energy transfer) exciting light of one-photon excitation mostly is ultraviolet-visible waveband, because the light of ultraviolet-visible waveband can only the several mm depths of transdermal, this has just limited with the local lesion in PDT treatment human body.Adsorption frequency corresponding to PDT based on two-photon absorption process is at 700-1100nm wave band, and the light of this wave band has better permeability to tissue, can carry out imaging and treatment to darker focus; On the other hand, two-photon absorption frequency is directly proportional to the quadratic power of light intensity, so this process is concentrated near volume less focus, thereby can effectively improve spatial resolution, avoids damaging normal cell tissue.
Although infrared light can reduce absorption and the scattering effect of biological tissue, the development of the photosensitizer of efficient absorption infrared light (for example two-photon is photosensitive dose) remains a challenge.
Summary of the invention
Technical problem to be solved by this invention is that a kind of phthalocyanine-quantum dot novel photosensitive agent providing for above-mentioned deficiency of the prior art and preparation method thereof is provided, photosensitive dose of described phthalocyanine-quantum dot is photosensitive dose of two-photon, can under infrared light, excite, FRET (fluorescence resonance energy transfer) is high.
The present invention solves the problems of the technologies described above adopted technical scheme:
-quantum dot novel photosensitive agent, the system that it is comprised of phthalocyanine solution and CdTe quantum dot solution.
Press such scheme, described phthalocyanine solution is dissolved in phthalocyanine powder in deionized water and makes, and phthalocyanine molar concentration is
4.5×10
-5-1.5×10
-4mol/L。
Press such scheme, described CdTe quantum dot solution is that solid CdTe is dissolved in deionized water and is made, and the molar concentration of CdTe quantum dot is 6.0 * 10
-6-9.0 * 10
-6mol/L.
Press such scheme, the volume ratio of described phthalocyanine solution and CdTe quantum dot solution is (25-150): 1.
The preparation method of above-mentioned phthalocyanine-quantum dot novel photosensitive agent, comprises the following steps:
(1) phthalocyanine powder is dissolved in deionized water, phthalocyanine molar concentration is 4.5 * 10
-5-1.5 * 10
-4mol/L, makes phthalocyanine solution;
(2) solid CdTe is dissolved in deionized water, the molar concentration of CdTe quantum dot is 6.0 * 10
-6-9.0 * 10
-6mol/L, makes CdTe quantum dot solution;
(3) by phthalocyanine solution and CdTe quantum dot solution according to volume ratio (25-150): 1 fully mixes, supersonic oscillations 20-30min under 20-27 ℃ of condition, resulting solution system, i.e. described phthalocyanine-quantum dot novel photosensitive agent.
Press such scheme, described phthalocyanine is C.I. Pigment Blue 15, and being is provided by Shanghai Pin Ao company limited; Described CdTe quantum dot is by the Chinese patent (patent No.: method CN 102634342A) providing makes.
Above-mentioned phthalocyanine-quantum dot novel photosensitive agent can be applied as a kind of optical dynamic therapy medicine.
Photosensitive dose of the phthalocyanine-quantum dot of optical dynamic therapy provided by the present invention, its preparation process as shown in Figure 2.
Structure of the present invention is on the basis of Spherical Quantum Dots, wraps up in attached phthalocyanine around form novel photosensitive agent at quantum dot.CdTe quantum dot has absorbing light spectrum width, the characteristic that emission spectra is narrow and symmetrical, the overlapping degree of fluorescence emission spectrum and acceptor molecule absorption spectrum can regulate according to quantum dot size size, its fluorescence quantum yield is higher, and fluorescence lifetime is long, can not bleach, so the present invention selects CdTe quantum dot as the energy donor of complex photosensitizer under two-photon excitation; C.I. Pigment Blue 15 has stronger absworption peak at 650-800nm wave band, so the present invention selects C.I. Pigment Blue 15 to be used as the energy acceptor under two-photon excitation.Photosensitive dose of character with FRET (fluorescence resonance energy transfer) of phthalocyanine-quantum dot of the present invention, and there is the double properties of organic dyestuff and quantum dot, for photosensitizer, in the practical application of life science, there is certain meaning.
Compared with prior art, beneficial effect of the present invention is as follows:
First, photosensitive dose of phthalocyanine-quantum dot of the present invention, C.I. Pigment Blue 15 has very strong absworption peak at 600-800nm wave band, and the fluorescence emission peak of CdTe quantum dot is at 650nm, be positioned at the absorption bands of phthalocyanine, therefore photosensitive dose of phthalocyanine-quantum dot of the present invention both can have been realized the broad excitation source range of choice, can utilize absorption cross-section that quantum dot is larger to improve the launching efficiency of phthalocyanine simultaneously, fully realize targeting and the therapeutic of phthalocyanine dye and quantum dot, can realize accurate identification and locate and treat cancerous cell.
The second, photosensitive dose of phthalocyanine-quantum dot of the present invention is photosensitive dose of two-photon, in excitation wavelength, is 780nm, phthalocyanine concentration 1.5 * 10
-4under mol/L, excitation light power 200mW condition, the transferring efficiency of fluorescence resonance energy that phthalocyanine-quantum dot of forming is photosensitive dose can reach 43.8%.Photosensitive dose of phthalocyanine-quantum dot of the present invention can interact with near-infrared laser, and tissue is had to better permeability, can carry out imaging and treatment to darker focus; And two-photon absorption efficiency is directly proportional to the quadratic power of light intensity, so this process is concentrated near volume less focus, can effectively improve spatial resolution, avoids damaging normal cell tissue.
The 3rd, photosensitive dose of light stability of phthalocyanine-quantum dot of the present invention is strong, the loss of effectively avoiding therapeutic process Chinese medicine to cause because of photobleaching, and preparation method is simple, easy to operate, stability is high and with low cost.
accompanying drawing explanation
Fig. 1 is PDT treatment principle flow chart.
Fig. 2 is the basic schematic diagram of process that the present invention prepares photosensitive dose of phthalocyanine-quantum dot.
Fig. 3 is the absorption spectra of C.I. Pigment Blue 15 and the emission spectra of CdTe quantum dot.
Fig. 4 is the fluorescence spectrum that embodiment 1-4 prepares photosensitive dose of phthalocyanine-quantum dot and comparative example.
Fig. 5 is under 780nm two-photon excitation, photosensitive dose of phthalocyanine-quantum dot that embodiment 1-4 is prepared and the fluorescence decay curve of comparative example.
Fig. 6 is under 780nm two-photon excitation, and embodiment 1 prepares the fluorescence decay curve of photosensitive dose of phthalocyanine-quantum dot and comparative example.
Fig. 7 is that concentration is 1.5 * 10
-4mol/L phthalocyanine solution, concentration are 6.0 * 10
-6mol/L CdTe quantum dot solution and embodiment 5 prepare the fluorescence spectrum of photosensitive dose of phthalocyanine-quantum dot.
In accompanying drawing, all with " CdTe+CuPc ", represent and in the present invention, prepare phthalocyanine-quantum photosensitizer.
The specific embodiment
Below in conjunction with the specific embodiment, describe the present invention, described embodiment contributes to understanding of the present invention and enforcement, is not construed as limiting the invention.In following examples, the Preparation and characterization of phthalocyanine-quantum dot novel photosensitive agent of the present invention is made to detailed description.
C.I. Pigment Blue 15 powder described in following embodiment is to be provided by Shanghai Pin Ao company limited; CdTe quantum dot described in following embodiment is by the Chinese patent (patent No.: method CN 102634342A) providing makes.
In embodiment phthalocyanine for solution ultraviolet-visible spectrophotometer (HITACHI U-3310, Japan) observe its absorption spectrum; CdTe for quantum dot solution fluorescence spectrophotometer (Jasco FP-6500, Japan) observe its emission spectra; The femto-second laser that two-photon excitation light source is 780nm with wavelength (Mira 900, Coherent, 76 MHz, 130 fs) excites; Fluorescence lifetime is measured with the single photon counter of time correlation.
the preparation method of the phthalocyanine solution in following embodiment is as follows:get C.I. Pigment Blue 15 powder 2.833g and be dissolved in 25mL deionized water, can obtain C.I. Pigment Blue 15 master grind, its concentration is 4.56279 * 10
-4mol/L, dilutes phthalocyanine mill base with deionized water, and the concentration that obtains phthalocyanine is 4.5 * 10
-5mol/L, 7.5 * 10
-5mol/L, 1.0 * 10
-4mol/L and 1.5 * 10
-4mol/L.
the preparation method of the CdTe quantum dot solution in following embodiment is as follows:get solid CdTe 9.14 * 10
-3mg is dissolved in 10mL deionized water, can obtain CdTe quantum dot solution, and its concentration is 3.807 * 10
-5mol/L.Get 20uL CdTe quantum dot, take deionized water as solvent, QDs is carried out to 5 times of dilutions, the concentration that obtains CdTe quantum dot is 7.61 * 10
-6mol/L.
As shown in Figure 3: C.I. Pigment Blue 15 has two absworption peaks, absworption peak lays respectively at 615nm and 714nm place, the emission spectra of the absorption spectra of C.I. Pigment Blue 15 and CdTe quantum dot has to a certain degree overlapping within the scope of 550-675nm, thereby this phthalocyanine-quantum dot mixed system (being photosensitizer solution) can produce power shift.
-quantum dot novel photosensitive agent, the system that it is comprised of phthalocyanine solution and CdTe quantum dot solution, phthalocyanine molar concentration is 1.5 * 10
-4mol/L, volume is 3mL, CdTe quantum dot solution concentration is 7.61 * 10
-6mol/L, volume is 20 uL.
The preparation method of above-mentioned phthalocyanine-quantum dot novel photosensitive agent, comprises the steps:
(1) phthalocyanine powder is dissolved in deionized water, phthalocyanine molar concentration is 1.5 * 10
-4mol/L, makes phthalocyanine solution;
(2) solid CdTe is dissolved in to deionized water, CdTe quantum dot solution concentration is 7.61 * 10
-6mol/L;
(3) phthalocyanine solution and CdTe quantum dot solution are fully mixed to supersonic oscillations 30min under 27 ℃ of conditions, resulting solution system, i.e. described phthalocyanine-quantum dot novel photosensitive agent according to volume ratio 150:1.
-quantum dot novel photosensitive agent, the system that it is comprised of phthalocyanine solution and CdTe quantum dot solution, phthalocyanine molar concentration is 1.0 * 10
-4mol/L, volume is 3mL, CdTe quantum dot solution concentration is 7.61 * 10
-6mol/L, volume is 20 uL.
-quantum dot novel photosensitive agent, the system that it is comprised of phthalocyanine solution and CdTe quantum dot solution, phthalocyanine molar concentration is 7.5 * 10
-5mol/L, volume is 3mL, CdTe quantum dot solution concentration is 7.61 * 10
-6mol/L, volume is 20 uL.
-quantum dot novel photosensitive agent, the system that it is comprised of phthalocyanine solution and CdTe quantum dot solution, phthalocyanine molar concentration is 4.5 * 10
-5mol/L, volume is 3mL, CdTe quantum dot solution concentration is 7.61 * 10
-6mol/L, volume is 20 uL.
comparative example
CdTe quantum dot solution, described CdTe quantum dot solution concentration is 7.61 * 10
-6mol/L.
data test (one)
In this data test, embodiment 1-4 prepares quantum dot solution described in photosensitive dose of phthalocyanine-quantum dot and comparative example, by fluorescence spectrophotometer (wavelength 550nm) observation fluorescence spectrum, as shown in Figure 4, and with femtosecond laser (wavelength 780nm) as two-photon excitation light source, excitation light power 500mW and the fluorescence lifetime of measuring CdTe QDs with the sub-enumerator of time correlative (detecting wavelength 650nm), as shown in Figure 5.Transferring efficiency of fluorescence resonance energy (
) according to following Equation for Calculating.
Table 1 has provided the phthalocyanine of preparing in embodiment 1-4--the energy transfer efficiency that CdTe quantum dot is photosensitive dose.
As shown in Figure 4: 650nm place is CdTe quantum dot emission peak, and 828nm place is C.I. Pigment Blue 15 emission peak.Along with the increase of phthalocyanine solution concentration, CdTe quantum dot significantly reduces in the emission peak light intensity at 650nm place, and the emission peak light intensity of phthalocyanine at 828nm place enlarges markedly.Therefore, the energy of CdTe quantum dot is transferred to C.I. Pigment Blue 15 by radiationless form, and FRET (fluorescence resonance energy transfer) has occurred.
As shown in Figure 5: in embodiment 1, in photosensitive dose of phthalocyanine-quantum dot, the fluorescence lifetime of CdTe QDs is 4.25ns; In embodiment 2, in photosensitive dose of phthalocyanine-quantum dot, the fluorescence lifetime of CdTe QDs is 4.38ns; In embodiment 3, in photosensitive dose of phthalocyanine-quantum dot, the fluorescence lifetime of CdTe QDs is 4.43ns; In embodiment 4, in photosensitive dose of phthalocyanine-quantum dot, the fluorescence lifetime of CdTe QDs is 4.56ns; And in comparative example, while there is not the energy acceptor phthalocyanine as the FRET (fluorescence resonance energy transfer) under two-photon excitation condition, the fluorescence lifetime of CdTe QDs is 5.26ns.
Upper table 1 shows: along with the increase of solution concentration, transferring efficiency of fluorescence resonance energy also increases accordingly, when phthalocyanine concentration is 1.5 * 10
-4during mol/L, the photosensitive dose of energy transfer efficiency maximum of phthalocyanine-quantum dot forming.
As shown in Figure 6: the CdTe quantum dot fluorescence life-span is 5.37ns, and in CdTe quantum dot/C.I. Pigment Blue 15 photosensitizer the CdTe quantum dot fluorescence life-span be 4.80ns, the CdTe quantum dot lost of life, shows that QDs has been transferred to C.I. Pigment Blue 15 by energy, and FRET (fluorescence resonance energy transfer) has occurred.
data test (two)
In this data test, with femtosecond laser (wavelength 780nm) as two-photon excitation light source, time correlation quantum number system (detect wavelength 650nm) detects described in photosensitive dose of phthalocyanine-quantum dot described in embodiment 1 and comparative example in quantum dot solution, the fluorescence lifetime of CdTe quantum dot, but described in to excite the excitation light power of the femtosecond laser of photosensitive dose of phthalocyanine-quantum dot be 200mW, 500mW, 850mW.
Table 2 is the fluorescence lifetime of quantum dot solution in comparative example, table 3 be in photosensitive dose of the phthalocyanine-quantum dot described in embodiment 1 in the fluorescence lifetime of CdTe quantum dot; Table 4 is under different excitation light powers, the transferring efficiency of fluorescence resonance energy that phthalocyanine quantum dot described in embodiment 1 is photosensitive dose.
Upper table 2, table 3 show: along with the increase of excitation light power, in photosensitizer and comparative example solution, the fluorescence lifetime of CdTe quantum dot obviously increases described in embodiment 1.
Upper table 4 shows: along with the increase of excitation light power, under two-photon excitation, transferring efficiency of fluorescence resonance energy constantly reduces.In phthalocyanine concentration 1.5 * 10
-4under mol/L, excitation light power 200mW condition, the transferring efficiency of fluorescence resonance energy that phthalocyanine-quantum dot of forming is photosensitive dose is the highest, can reach 43.8%.
Applicant finds by research, in a certain amount of QDs solution, change the concentration of phthalocyanine solution, can there is corresponding change in the fluorescence lifetime of quantum dot, by comparing with not adding the fluorescence lifetime of the equivalent QDs solution of phthalocyanine, can calculate the transferring efficiency of fluorescence resonance energy under different phthalocyanine concentration, thereby obtain preparing the best phthalocyanine concentration of photosensitive dose of new phthalocyanine-quantum dot.
-quantum dot novel photosensitive agent, the system that it is comprised of phthalocyanine solution and CdTe quantum dot solution, phthalocyanine molar concentration is 1.5 * 10
-4mol/L, volume is 2.5mL, CdTe quantum dot solution concentration is 6.0 * 10
-6mol/L, volume is 100 uL.Two kinds of solution are fully mixed to supersonic oscillations 20min under 20 ℃ of conditions, resulting solution system, i.e. described phthalocyanine-quantum dot novel photosensitive agent according to volume ratio 25::1.
-quantum dot novel photosensitive agent, the system that it is comprised of phthalocyanine solution and CdTe quantum dot solution, phthalocyanine molar concentration is 1.5 * 10
-4mol/L, volume is 2.5mL, CdTe quantum dot solution concentration is 9.0 * 10
-6mol/L, volume is 100 uL.Two kinds of solution are fully mixed to supersonic oscillations 20min under 20 ℃ of conditions, resulting solution system, i.e. described phthalocyanine-quantum dot novel photosensitive agent according to volume ratio 25:1.
data test (three)
In this data test, embodiment 5 prepares the photosensitive agent solution of phthalocyanine-quantum dot, by fluorescence spectrophotometer (wavelength 550nm) observation fluorescence spectrum, normalized curve as shown in Figure 7, known: photosensitive dose of intensity at 650nm place of phthalocyanine-quantum dot is lower than the intensity of pure quantum dot, intensity in the intensity at 760nm place higher than pure phthalocyanine, illustrates in this process, and the energy of CdTe quantum dot is shifted and passed to phthalocyanine by radiationless form energy.
Claims (5)
1. phthalocyanine-quantum dot novel photosensitive agent, is characterized in that the system that it is comprised of phthalocyanine solution and CdTe quantum dot solution.
2. a kind of phthalocyanine-quantum dot novel photosensitive agent according to claim 1, is characterized in that described phthalocyanine solution is dissolved in phthalocyanine powder in deionized water and makes, and the molar concentration of phthalocyanine is 4.5 * 10
-5-1.5 * 10
-4mol/L.
3. a kind of phthalocyanine-quantum dot novel photosensitive agent according to claim 1, is characterized in that described CdTe quantum dot solution is that solid CdTe is dissolved in deionized water and is made, and the molar concentration of CdTe quantum dot is 6.0 * 10
-6-9.0 * 10
-6mol/L.
4. according to a kind of phthalocyanine-quantum dot novel photosensitive agent described in claim 1 or 2 or 3, the volume ratio that it is characterized in that described phthalocyanine solution and CdTe quantum dot solution is (25-150): 1.
5. the preparation method of phthalocyanine-quantum dot novel photosensitive agent claimed in claim 1, is characterized in that it comprises the following steps:
(1) phthalocyanine powder is dissolved in deionized water, phthalocyanine molar concentration is 4.5 * 10
-5-1.5 * 10
-4mol/L, makes phthalocyanine solution;
(2) solid CdTe is dissolved in deionized water, the molar concentration of CdTe quantum dot is 6.0 * 10
-6-9.0 * 10
-6mol/L, makes CdTe quantum dot solution;
(3) by phthalocyanine solution and CdTe quantum dot solution according to volume ratio (25-150): 1 fully mixes, supersonic oscillations 20-30min under 20-27 ℃ of condition, resulting solution system, i.e. described phthalocyanine-quantum dot novel photosensitive agent.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102869983A (en) * | 2010-03-26 | 2013-01-09 | 巴斯德研究所 | Method to increase the number of detectable photons during the imaging of a biological marker |
| CN104916781A (en) * | 2015-05-18 | 2015-09-16 | 中国华能集团清洁能源技术研究院有限公司 | Wideband solar cell adopting resonance energy transfer layer |
| CN107033886A (en) * | 2017-04-25 | 2017-08-11 | 安徽师范大学 | With being catalyzed and indicate difunctional fluorescent carbon point and its preparation method and application |
-
2013
- 2013-10-12 CN CN201310475425.3A patent/CN103536918B/en not_active Expired - Fee Related
Non-Patent Citations (2)
| Title |
|---|
| DUYGU AYDIN TEKDAS ET AL.: "Photodynamic therapy potential of thiol-stabilized CdTe quantum dot-group 3A phthalocyanine conjugates (QD-Pc)", 《SPECTROCHIMICA ACTA PART A》 * |
| LEI LI ET AL.: "Quantum dot-aluminum phthalocyanine conjugates perform photodynamic reactions to kill cancer cells via fluorescence resonance energy transfer", 《NANOSCALE RESEARCH LETTERS》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102869983A (en) * | 2010-03-26 | 2013-01-09 | 巴斯德研究所 | Method to increase the number of detectable photons during the imaging of a biological marker |
| CN104916781A (en) * | 2015-05-18 | 2015-09-16 | 中国华能集团清洁能源技术研究院有限公司 | Wideband solar cell adopting resonance energy transfer layer |
| CN107033886A (en) * | 2017-04-25 | 2017-08-11 | 安徽师范大学 | With being catalyzed and indicate difunctional fluorescent carbon point and its preparation method and application |
| CN107033886B (en) * | 2017-04-25 | 2019-06-25 | 安徽师范大学 | With being catalyzed and indicate difunctional fluorescent carbon point and its preparation method and application |
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