CN110859970B - Cyanine dye FD-1080J-aggregate and preparation method and application thereof - Google Patents
Cyanine dye FD-1080J-aggregate and preparation method and application thereof Download PDFInfo
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- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 239000000975 dye Substances 0.000 claims abstract description 51
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000010521 absorption reaction Methods 0.000 claims abstract description 10
- 210000004204 blood vessel Anatomy 0.000 claims abstract description 10
- 238000003384 imaging method Methods 0.000 claims abstract description 10
- 238000000799 fluorescence microscopy Methods 0.000 claims abstract description 8
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 7
- 230000005284 excitation Effects 0.000 claims abstract description 5
- GDIYMWAMJKRXRE-UHFFFAOYSA-N (2z)-2-[(2e)-2-[2-chloro-3-[(z)-2-(1,3,3-trimethylindol-1-ium-2-yl)ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-1,3,3-trimethylindole Chemical compound CC1(C)C2=CC=CC=C2N(C)C1=CC=C1C(Cl)=C(C=CC=2C(C3=CC=CC=C3[N+]=2C)(C)C)CCC1 GDIYMWAMJKRXRE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000036571 hydration Effects 0.000 claims abstract description 3
- 238000006703 hydration reaction Methods 0.000 claims abstract description 3
- 239000010409 thin film Substances 0.000 claims abstract description 3
- 230000002792 vascular Effects 0.000 claims abstract 2
- 239000000523 sample Substances 0.000 claims description 10
- 238000009210 therapy by ultrasound Methods 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 6
- 239000008055 phosphate buffer solution Substances 0.000 claims description 5
- 239000002504 physiological saline solution Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000002105 nanoparticle Substances 0.000 claims description 4
- 239000008367 deionised water Substances 0.000 claims description 2
- 229910021641 deionized water Inorganic materials 0.000 claims description 2
- 239000012528 membrane Substances 0.000 claims description 2
- 239000002872 contrast media Substances 0.000 claims 1
- 238000000108 ultra-filtration Methods 0.000 claims 1
- 210000004556 brain Anatomy 0.000 abstract description 6
- 239000000178 monomer Substances 0.000 abstract description 3
- 239000012620 biological material Substances 0.000 abstract description 2
- 210000001715 carotid artery Anatomy 0.000 abstract description 2
- 206010020772 Hypertension Diseases 0.000 abstract 1
- 230000001631 hypertensive effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 241000699666 Mus <mouse, genus> Species 0.000 description 8
- 239000011550 stock solution Substances 0.000 description 8
- CITHEXJVPOWHKC-UUWRZZSWSA-N 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC CITHEXJVPOWHKC-UUWRZZSWSA-N 0.000 description 6
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 description 6
- 229960003724 dimyristoylphosphatidylcholine Drugs 0.000 description 6
- 230000035515 penetration Effects 0.000 description 4
- 238000005086 pumping Methods 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000635 electron micrograph Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011503 in vivo imaging Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
- A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
- A61K49/0032—Methine dyes, e.g. cyanine dyes
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
The invention belongs to the technical field of biological materials, and particularly relates to a cyanine dye FD-1080J-aggregate, a preparation method and biological application thereof. The preparation method comprises the step of self-assembling the cyanine dye and the phospholipid by a thin film hydration method to form an aggregate solution, wherein the cyanine dye is an organic micromolecule heptamethine cyanine fluorescent dye and is marked as a fluorescent probe FD-1080. The maximum absorption and emission peak of the prepared J-aggregate are both larger than 1300 nm, and the red shift is more than 300 nm compared with the monomer; the J-aggregate has uniform size, good water solubility and biocompatibility; under the excitation of a 1064 nm laser, the non-invasive brain and leg vascular fluorescence imaging above 1500 nm can be realized, and the spatial resolution and the signal-to-noise ratio are higher. The J aggregate can realize real-time dynamic blood vessel imaging of carotid artery of hypertensive rat, and can quickly evaluate hypotensor in clinical application.
Description
Technical Field
The invention belongs to the technical field of biological materials, and particularly relates to a cyanine dye FD-1080J-aggregate, a preparation method and biological application thereof.
Background
Accurate biomedical imaging methods are critical to the diagnosis and prognosis of disease. Among them, fluorescence imaging shows superior performance in terms of high sensitivity, high time resolution, and fast feedback, but is limited to a lower tissue penetration depth. In recent years, the second near infrared window (1000-1700 nm) has attracted the attention of researchers because of its lower light scattering, smaller absorption and auto-fluorescence of the biological tissue compared with the first near infrared window (700-900 nm). Especially over 1500 nm, greatly improves the imaging quality and penetration depth due to the weak absorption and scattering of the biological tissue itself. Therefore, the 1500-. However, probes in this range are currently inorganic nanoparticles. Clinical transformation due to unknown long-term cytotoxicity of inorganic nanoparticles in vivo. Therefore, there is an urgent need to design organic probes with long wavelengths.
In recent years, organic fluorescent dyes have attracted much attention as compared to inorganic materials, because organic dyes have a relatively small molecular weight, are easily metabolized, and can also realize emission in the near-infrared second window region. For example, the Zhang project group prepared the pentamethine cyanine fluorescent and heptamethine cyanine fluorescent dyes of the second near-infrared window, and the Dynagen project group prepared the donor-acceptor-donor (D-A-D) structure that can be used in the two-region window. However, the two-region window dyes prolong the emission peak by modifying the molecular structure of the dyes, have the disadvantages of complex preparation process and low yield, are mostly hydrophobic dyes, and can be used for in vivo imaging only by further modification. Therefore, it is urgently required to design a simple method for extending the maximum absorption and emission wavelengths of the organic dye.
For this purpose, the present invention prepares cyanine dye FD-1080J-aggregate, whose maximum absorption and emission peaks are 1360 nm and 1370 nm, respectively. To date, J-aggregates with maximum absorption and emission wavelengths above 1300 nm have not been reported and have been used to image non-invasive blood vessels in the legs and brain of mice and to evaluate the efficacy of hypotensive drugs by altering the carotid blood vessels.
Disclosure of Invention
The invention aims to provide a cyanine dye aggregate which has the advantages of simple preparation process, good water solubility, good biocompatibility, high light stability and maximum absorption and emission wavelengths above 1300 nm, and a preparation method and application thereof.
In the invention, the cyanine dye is an organic micromolecule heptamethine cyanine fluorescent dye which is marked as a fluorescent probe FD-1080.
The preparation method of the cyanine dye aggregate provided by the invention comprises the following specific steps:
the cyanine dye and the phospholipid are self-assembled by a thin film hydration method to form an aggregate solution. Adding cyanine dye and phospholipid according to a certain proportion, carrying out spin drying by a rotary evaporator, and adding aqueous solution under an ultrasonic state to obtain an aggregate, which is marked as cyanine dye FD-1080J-aggregate.
In order to ensure the formation of FD-1080J-aggregates, the preferable technical scheme is that the concentration of the cyanine dye is 1 mu M-2 mM. The molar ratio of the cyanine dye to the phospholipid is 1:2000-1:1 (namely 1 (2000-1)), the ultrasonic time is 10 s-30 min, and the ultrasonic temperature is 0-100 ℃.
In the present invention, the phospholipid includes phospholipid glyceride and sphingomyelin. The aqueous solution includes phosphate buffer solution, physiological saline, distilled water, etc. The ultrasonic device has an ultrasonic cleaning pan and a probe type ultrasonic device.
In order to facilitate storage, the obtained cyanine dye FD-1080J-aggregate solution is freeze-dried by using a freeze dryer, so that the powdered cyanine dye FD-1080J-aggregate is obtained. Or, the obtained FD-1080J-aggregate solution is ultrafiltered and concentrated, and is filtered by a needle type filter membrane to obtain uniform nano particles. The J-aggregate has good water solubility and biocompatibility and can be repeatedly frozen and thawed. It can be dissolved in phosphate buffer solution, normal saline, and distilled water.
After the cyanine dye FD-1080 forms a J-aggregate, the maximum absorption peak and the maximum emission peak are above 1300 nm (the maximum absorption peak is red-shifted from 1012 nm to 1360 nm, and the maximum emission peak is red-shifted from 1052 nm to 1370 nm), namely, the cyanine dye has a near-infrared second window excitation function. Compared with FD-1080 monomers, the J aggregate can realize fluorescence imaging of more than 1500 nm (under the excitation of a 1064 nm laser), and has deeper penetration depth and higher spatial resolution.
The cyanine dye FD-1080J-aggregate prepared by the invention can be used as a near-infrared second window imaging probe and is applied to dynamic blood vessel imaging and the like.
For example, the cyanine dye FD-1080J-aggregate can be used as an angiographic agent to perform noninvasive fluorescence imaging on blood vessels of the brain and the legs of a mouse and perform dynamic blood vessel imaging on the carotid artery of a rat, and further, the change of the width of the blood vessel is utilized to evaluate the curative effect of the antihypertensive drug.
In conclusion, the invention provides a cyanine dye FD-1080J-aggregate, a preparation method and biological application thereof, wherein the J-aggregate has deeper penetration depth and excellent spatial resolution as a near-infrared second window fluorescence imaging probe, and the J-aggregate has the characteristics of simple preparation method, excellent water solubility, biocompatibility and the like.
Drawings
FIG. 1 shows the absorption and emission spectra of FD-1080 monomers and J-aggregates of cyanine dye.
FIG. 2 is an electron micrograph of an aggregate of cyanine dye FD-1080J.
FIG. 3 is a graph of the absorption spectrum of cyanine dye FD-1080J-aggregate in phosphate buffer solution for different days.
FIG. 4 is a graph showing the absorption spectra of cyanine dye FD-1080J-aggregate in physiological saline for different days.
FIG. 5 is an image of cyanine dye FD-1080J-aggregate on mouse leg vessels.
FIG. 6 shows imaging of cyanine dye FD-1080J-aggregate pairs on mouse brain blood vessels.
Detailed Description
Example 1:
FD-1080 (1.13 mg, 1.5 μmol) was weighed and dissolved in 1mL of methanol, and 25 mg of dimyristoyl phosphatidylcholine (DMPC) was dissolved in 1mL of chloroform. Adding 20 mu L of FD-1080 stock solution and 407 mu L of DMPC stock solution into a 25 mL round-bottom flask, enabling the molar ratio of dye to phospholipid to be 1:500, performing spin-drying on a rotary evaporator, pumping for 2 hours in a vacuum drying oven, adding 2 mL of phosphate buffer solution into a 50 ℃ water bath, performing ultrasonic treatment for 10 minutes, and transferring to probe type ultrasonic treatment for 15 minutes.
Example 2:
FD-1080 (1.13 mg, 1.5 mu mol) was weighed and dissolved in 1mL of methanol, dimyristoyl phosphatidylcholine (DMPC) 25 mg was dissolved in 1mL of chloroform, phospholipid polyethylene glycol 2000 (DSPE-PEG)2000) 25 mg was dissolved in 1mL of chloroform. Adding 200 mu L FD-1080 stock solution, 155 mu L DMPC stock solution and 30 mu L DSPE-PEG into a 25 mL round bottom flask2000And (3) storing the solution, wherein the molar ratio of the dye to the phospholipid is 1:20, performing spin drying on a rotary evaporator, pumping in a vacuum drying oven for 2 hours, adding 2 mL of physiological saline into a 50 ℃ water bath kettle, performing ultrasonic treatment for 10 minutes, and transferring to a probe type ultrasonic treatment for 15 minutes.
Example 3:
FD-1080 (1.13 mg, 1.5 μmol) was weighed and dissolved in 1mL of methanol, and 25 mg of Dipalmitoylphosphatidylcholine (DPPC) was dissolved in 1mL of chloroform. Adding 20 mu L FD-1080 stock solution and 82 mu L DPPC stock solution into a 25 mL round bottom flask, enabling the molar ratio of dye to phospholipid to be 1:100, performing spin-drying on a rotary evaporator, pumping for 2 hours in a vacuum drying oven, adding 2 mL deionized water into a 50 ℃ water bath, performing ultrasonic treatment for 5 minutes, and transferring to probe ultrasonic treatment for 10 minutes.
Example 4:
FD-1080 (1.13 mg, 1.5 μmol) was weighed and dissolved in 1mL of methanol, and 25 mg of Dipalmitoylphosphatidylcholine (DPPC) was dissolved in 1mL of chloroform. Adding 200 mu L FD-1080 stock solution and 54 mu L DPPC stock solution into a 25 mL round-bottom flask, enabling the molar ratio of dye to phospholipid to be 1:6.67, performing spin-drying on a rotary evaporator, pumping for 2 hours in a vacuum drying oven, adding 2 mL physiological saline into a 50 ℃ water bath kettle, performing ultrasonic treatment for 2 minutes, and transferring to probe ultrasonic treatment for 15 minutes.
Application example:
1. cyanine dye FD-1080J-aggregate was imaged on mouse leg vessels. The method comprises the following specific steps:
injecting 200 μ L cyanine dye FD-1080J-aggregate with concentration of 200 μ M into tail vein of anesthetized mouse, irradiating left leg of mouse with 1064 nm external laser with power density of 250 mW/cm2A 1500 nm filter can be used for leg imaging (see fig. 5).
2. The cyanine dye FD-1080 and phospholipid form J-aggregate to image the brain blood vessels of the mice. The method comprises the following specific steps:
injecting 200 μ L of the compound with a concentration of 200 μ M into tail vein of anesthetized mouse, irradiating the brain of the mouse with 1064 nm external laser with a power density of 250 mW/cm2Brain fluorescence imaging was performed with 1500 nm filters (see figure 6).
The above description is only an embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of changes and substitutions within the technical scope of the present invention, and the present invention shall be covered thereby.
Claims (7)
1. The preparation method of the cyanine dye FD-1080J-aggregate is characterized by comprising the following specific steps: self-assembling cyanine dyes and phospholipids by a thin film hydration method to form an aggregate solution, specifically adding the cyanine dyes and the phospholipids according to a certain proportion, carrying out spin-drying by a rotary evaporator, and adding an aqueous solution under an ultrasonic state to obtain an aggregate; the cyanine dye is an organic micromolecule heptamethine cyanine fluorescent dye and is marked as a fluorescent probe FD-1080, and the obtained aggregate is marked as a cyanine dye FD-1080J-aggregate.
2. The preparation method according to claim 1, wherein the concentration of the cyanine dye solution is 1 μ M to 2 mM; the mole ratio of the cyanine dye to the phospholipid is 1:2000-1: 1; the ultrasonic treatment time is 10 s-30 min, and the ultrasonic treatment temperature is 0-100 ℃.
3. The process according to claim 1 or 2, wherein the phospholipid is selected from the group consisting of a phospholipid glyceride, a sphingomyelin; the aqueous solution is selected from phosphate buffer solution, physiological saline and deionized water.
4. The preparation method according to claim 3, characterized in that the obtained cyanine dye FD-1080J-aggregate solution is lyophilized by a lyophilizer to obtain powdered cyanine dye FD-1080J-aggregate; or the obtained FD-1080J-aggregate solution is subjected to ultrafiltration concentration and is filtered by a needle type filter membrane to obtain uniform nano particles.
5. The cyanine dye FD-1080J-aggregate obtained by the preparation method of any one of claims 1-4, which has a maximum absorption peak and a maximum emission peak above 1300 nm, i.e. has near-infrared second window excitation and emission functions, and can realize fluorescence imaging above 1500 nm under the excitation of a 1064 nm laser.
6. Use of the cyanine dye FD-1080J-aggregate of claim 5 in the preparation of a near-infrared second window imaging probe for dynamic vascular imaging.
7. Use of the cyanine dye FD-1080J-aggregate as claimed in claim 5 for the preparation of an angiographic contrast agent for non-invasive fluorescence imaging of blood vessels.
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