CN116637209B - Fluorescent dye compound and preparation method thereof - Google Patents
Fluorescent dye compound and preparation method thereof Download PDFInfo
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- CN116637209B CN116637209B CN202310560069.9A CN202310560069A CN116637209B CN 116637209 B CN116637209 B CN 116637209B CN 202310560069 A CN202310560069 A CN 202310560069A CN 116637209 B CN116637209 B CN 116637209B
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- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 71
- 150000001875 compounds Chemical class 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 43
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 43
- 239000001007 phthalocyanine dye Substances 0.000 claims abstract description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000013329 compounding Methods 0.000 claims abstract description 8
- 239000002131 composite material Substances 0.000 claims description 49
- 239000007788 liquid Substances 0.000 claims description 38
- 238000003756 stirring Methods 0.000 claims description 21
- 238000002156 mixing Methods 0.000 claims description 14
- 238000000265 homogenisation Methods 0.000 claims description 12
- 238000001694 spray drying Methods 0.000 claims description 11
- 108010038807 Oligopeptides Proteins 0.000 claims description 10
- 102000015636 Oligopeptides Human genes 0.000 claims description 10
- 238000009210 therapy by ultrasound Methods 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 7
- 239000008367 deionised water Substances 0.000 claims description 7
- 229910021641 deionized water Inorganic materials 0.000 claims description 7
- 238000002390 rotary evaporation Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- MVORZMQFXBLMHM-QWRGUYRKSA-N Gly-His-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@@H](NC(=O)CN)CC1=CN=CN1 MVORZMQFXBLMHM-QWRGUYRKSA-N 0.000 claims description 2
- 108010038983 glycyl-histidyl-lysine Proteins 0.000 claims description 2
- 238000000527 sonication Methods 0.000 claims description 2
- 239000002245 particle Substances 0.000 abstract description 17
- 230000004071 biological effect Effects 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 25
- 238000000034 method Methods 0.000 description 8
- 238000004090 dissolution Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000011161 development Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical class O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000008685 targeting Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
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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
- A61K49/0036—Porphyrins
-
- 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
- A61K49/005—Fluorescence in vivo characterised by the carrier molecule carrying the fluorescent agent
- A61K49/0054—Macromolecular compounds, i.e. oligomers, polymers, dendrimers
-
- 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
- A61K49/005—Fluorescence in vivo characterised by the carrier molecule carrying the fluorescent agent
- A61K49/0056—Peptides, proteins, polyamino acids
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
The invention discloses a fluorescent dye compound and a preparation method thereof, wherein the fluorescent dye compound is formed by compounding phthalocyanine dye, polyethylene glycol and oligopeptide-1. The invention has good hydrophilicity and biological property, improves the dispersibility and stability in water, has simple preparation method, and adapts to corresponding technological parameters, so that the particle size of the fluorescent dye compound is uniform, and the fluorescent dye compound has good dispersibility.
Description
Technical Field
The invention relates to a fluorescent dye compound and a preparation method thereof, belonging to the technical field of fluorescent materials.
Background
Fluorescent dyes are increasingly attracting attention of industry and widely used in fields of biological medicine, chemical industry, electrochemistry and the like as functional materials. The phthalocyanine dye is near infrared micromolecule fluorescent dye, the fluorescence spectrum of the phthalocyanine dye is 600-700 nm, the phthalocyanine dye is a hydrophobic fluorescent dye which needs to use organic solvents such as dimethyl sulfoxide and the like, but the organic solvents have toxicity to human bodies and do not accord with the concept of health and environmental protection; water is used as a solvent, but phthalocyanine dye is easy to aggregate in aqueous solution, so that stability and biocompatibility are poor, and further development and application of the phthalocyanine dye in fluorescent marking and imaging are limited.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides the fluorescent dye compound which has good hydrophilicity and biological property, improves the dispersibility and stability in water, has a simple preparation method, is suitable for corresponding technological parameters, ensures that the particle size of the fluorescent dye compound is uniform, and has good dispersibility.
In order to achieve the above purpose, the present invention adopts the following technical scheme: a fluorescent dye compound is formed by compounding phthalocyanine dye, polyethylene glycol and oligopeptide-1.
Preferably, the mass ratio of the phthalocyanine dye to the polyethylene glycol to the oligopeptide is 1:1.6-1.9:0.6, and the average molecular weight of the polyethylene glycol is 760-840.
The invention also provides a preparation method of the fluorescent dye compound, which comprises the following steps:
(1) Dissolving polyethylene glycol in deionized water, and stirring to obtain a composite solution A;
(2) Adding the phthalocyanine dye into the composite liquid A, mixing, keeping the stirring speed unchanged, heating to 90-95 ℃, preserving heat for 3-4 hours, and carrying out high-pressure homogenization treatment to obtain composite liquid B;
(3) Cooling the composite liquid B to 45-50 ℃, keeping stirring unchanged, adding oligopeptide-1, mixing, preserving heat for 1-2 h, and performing ultrasonic treatment to obtain composite liquid C;
(4) And (3) carrying out reduced pressure rotary evaporation concentration and spray drying on the composite liquid C to obtain the fluorescent dye composite.
Preferably, the stirring conditions are: the stirring speed is 1500-2000 rpm.
Preferably, the high pressure homogenization conditions: the homogenizing pressure is 15MPa, and the homogenizing time is 20-30 min.
Preferably, the sonication conditions: the ultrasonic frequency is 10-15 KHz, and the ultrasonic time is 1-2 h.
Preferably, the water content after concentration is 40 to 50%.
Preferably, spray drying conditions: the air temperature is 180-200 ℃, and the air outlet temperature is 75-85 ℃.
The invention has the beneficial effects that:
1. the fluorescent dye compound disclosed by the invention takes phthalocyanine dye as fluorescent dye, is compounded and cooperated with polyethylene glycol and oligopeptide-1, has good hydrophilicity and biological property, and improves the dispersibility and stability in water.
2. The polyethylene glycol and oligopeptide-1 in the fluorescent dye compound provided by the invention are synergistic, so that the surface activity of the fluorescent dye is enhanced, the fluorescent dye compound has good stability and biocompatibility, and adverse effects of uneven fluorescent dye distribution on the performance of the fluorescent dye compound are avoided.
3. The oligopeptide-1 in the fluorescent dye compound has the advantages of good tissue permeability, metabolic stability and modification, and targeting transportation, can increase the stability and targeting property of the fluorescent dye compound in vivo, and can promote the development and application of phthalocyanine dye in fluorescent marking and imaging.
4. The preparation method is simple, and the corresponding technological parameters are adapted, so that the particle size of the fluorescent dye compound is uniform, the fluorescent dye compound has good dispersibility, and the instant and the dispersibility of the fluorescent dye compound in water are further improved.
Drawings
FIG. 1 is a graph showing fluorescence intensity of a fluorescent dye complex according to example 1 of the present invention;
FIG. 2 is a graph showing fluorescence intensity of the fluorescent dye complex according to example 2 of the present invention;
FIG. 3 is a graph showing fluorescence intensity of the fluorescent dye complex according to example 3 of the present invention;
FIG. 4 is a graph showing fluorescence intensity of the fluorescent dye complex according to example 4 of the present invention;
FIG. 5 is a graph of fluorescence intensity of the fluorescent dye complex of example 5 of the present invention;
FIG. 6 is a graph of fluorescence intensity of the fluorescent dye complex of comparative example 1;
FIG. 7 is a graph showing fluorescence intensity of the fluorescent dye complex of comparative example 2.
Detailed Description
The invention will now be more clearly and more fully described by way of the following specific examples, which are not intended to be limiting.
The structural formula of the phthalocyanine dye selected by the invention is
The sequence of oligopeptide-1 selected by the invention is Gly-His-Lys.
Example 1
A fluorescent dye compound is formed by compounding phthalocyanine dye, polyethylene glycol and oligopeptide-1; the mass ratio of the phthalocyanine dye to the polyethylene glycol to the oligopeptide is 1:1.6:0.6, and the average molecular weight of the polyethylene glycol is 760-840;
The preparation method comprises the following specific steps:
(1) 160g of polyethylene glycol is dissolved in 540g of deionized water, and the mixture is stirred and dissolved at 1500rpm to obtain a composite solution A;
(2) Adding 100g of phthalocyanine dye into the composite liquid A, mixing, keeping the stirring speed unchanged, heating to 90-95 ℃, preserving heat for 3h, and carrying out high-pressure homogenization treatment for 20min under 15MPa to obtain composite liquid B;
(3) Cooling the composite liquid B to 45-50 ℃, keeping stirring unchanged, adding 60g of oligopeptide-1, mixing, preserving heat for 21-2 h, and performing ultrasonic treatment at 10KHz for 2h to obtain composite liquid C;
(4) Concentrating the composite liquid C by reduced pressure rotary evaporation until the water content is 40.3%, and spray drying at the inlet air temperature of 180 ℃ and the outlet air temperature of 80 ℃ to obtain fluorescent dye composite in the form of particles.
Example 2
A fluorescent dye compound is formed by compounding phthalocyanine dye, polyethylene glycol and oligopeptide-1; the mass ratio of the phthalocyanine dye to the polyethylene glycol to the oligopeptide is 1:1.7:0.6, and the average molecular weight of the polyethylene glycol is 760-840;
The preparation method comprises the following specific steps:
(1) 17g of polyethylene glycol is dissolved in 600g of deionized water, and stirred and dissolved at 1700rpm to obtain a composite liquid A;
(2) Adding 100g of phthalocyanine dye into the composite liquid A, mixing, keeping the stirring speed unchanged, heating to 90-95 ℃, preserving heat for 3h, and carrying out high-pressure homogenization treatment under 15MPa for 30min to obtain composite liquid B;
(3) Cooling the composite liquid B to 45-50 ℃, keeping stirring unchanged, adding 60g of oligopeptide-1, mixing, preserving heat for 1.5h, and performing ultrasonic treatment at 15KHz for 1h to obtain composite liquid C;
(4) Concentrating the composite liquid C by reduced pressure rotary evaporation until the water content is 45%, and spray drying at 180 ℃ and 75 ℃ of air inlet temperature and air outlet temperature to obtain fluorescent dye composite in the form of particles.
Example 3
A fluorescent dye compound is formed by compounding phthalocyanine dye, polyethylene glycol and oligopeptide-1; the mass ratio of the phthalocyanine dye to the polyethylene glycol to the oligopeptide is 1:1.8:0.6, and the average molecular weight of the polyethylene glycol is 760-840;
The preparation method comprises the following specific steps:
(1) 180g of polyethylene glycol is dissolved in 680g of deionized water, and stirred and dissolved at 1800rpm to obtain a composite liquid A;
(2) Adding 100g of phthalocyanine dye into the composite liquid A, mixing, keeping the stirring speed unchanged, heating to 90-95 ℃, preserving heat for 3.5h, and carrying out high-pressure homogenization treatment under 15MPa for 25min to obtain composite liquid B;
(3) Cooling the composite liquid B to 45-50 ℃, keeping stirring unchanged, adding 60g of oligopeptide-1, mixing, preserving heat for 1h, and performing ultrasonic treatment at 12KHz for 1.5h to obtain composite liquid C;
(4) Concentrating the composite liquid C by reduced pressure rotary evaporation until the water content is 50%, and spray drying at 190 ℃ for air inlet and 80 ℃ for air outlet to obtain fluorescent dye composite in the form of particles.
Example 4
A fluorescent dye compound is formed by compounding phthalocyanine dye, polyethylene glycol and oligopeptide-1; the mass ratio of the phthalocyanine dye to the polyethylene glycol to the oligopeptide is 1:1.9:0.6, and the average molecular weight of the polyethylene glycol is 760-840;
The preparation method comprises the following specific steps:
(1) 190g of polyethylene glycol is dissolved in 660g of deionized water, and the mixture is stirred and dissolved at 2000rpm to obtain a composite solution A;
(2) Adding 100g of phthalocyanine dye into the composite liquid A, mixing, keeping the stirring speed unchanged, heating to 90-95 ℃, preserving heat for 4 hours, and carrying out high-pressure homogenization treatment under 15MPa for 30 minutes to obtain composite liquid B;
(3) Cooling the composite liquid B to 45-50 ℃, keeping stirring unchanged, adding 60g of oligopeptide-1, mixing, preserving heat for 2h, and performing ultrasonic treatment at 15KHz for 1h to obtain composite liquid C;
(4) Concentrating the composite liquid C by reduced pressure rotary evaporation until the water content is 46.5%, and spray drying at the air inlet temperature of 200 ℃ and the air outlet temperature of 85 ℃ to obtain fluorescent dye composite in the form of particles.
Example 5
A fluorescent dye compound is formed by compounding phthalocyanine dye, polyethylene glycol and oligopeptide-1; the mass ratio of the phthalocyanine dye to the polyethylene glycol to the oligopeptide is 1:1.75:0.6, and the average molecular weight of the polyethylene glycol is 760-840;
The preparation method comprises the following specific steps:
(1) Dissolving 87.5g of polyethylene glycol in 300g of deionized water, and stirring and dissolving at 1700rpm to obtain a composite liquid A;
(2) 50g of phthalocyanine dye is added into the composite liquid A for mixing, the stirring speed is kept unchanged, the mixture is heated to 90-95 ℃, then the temperature is kept for 3 hours, and then high-pressure homogenization treatment is carried out for 25 minutes under 15MPa, so as to obtain composite liquid B;
(3) Cooling the composite liquid B to 45-50 ℃, keeping stirring unchanged, adding 30g of oligopeptide-1, mixing, preserving heat for 1.5h, and performing ultrasonic treatment at 12.5KHz for 2h to obtain composite liquid C;
(4) Concentrating the composite liquid C by reduced pressure rotary evaporation until the water content is 47.5%, and spray drying at the air inlet temperature of 200 ℃ and the air outlet temperature of 85 ℃ to obtain fluorescent dye composite in the form of particles.
Comparative example 1
The fluorescent dye complex of this comparative example 1 and its preparation procedure are the same as in example 1, except that: the average molecular weight of the fluorescent polyethylene glycol is 570-630; the fluorescent dye complex was found to be pasty by drying.
Comparative example 2
The fluorescent dye complex of this comparative example 2 and its preparation procedure are the same as in example 1, except that: the average molecular weight of the polyethylene glycol is 950-1050.
Comparative example 3
The fluorescent dye complex of this comparative example 3 and its preparation procedure are the same as in example 1, except that: the mass ratio of the phthalocyanine dye to the polyethylene glycol to the oligopeptide is 1:1.55:0.6, and the addition amount of the polyethylene glycol is 155g.
Comparative example 4
The fluorescent dye complex of this comparative example 4 and its preparation procedure are the same as in example 4, except that: the mass ratio of the phthalocyanine dye to the polyethylene glycol to the oligopeptide is 1:2:0.6, and the addition amount of the polyethylene glycol is 200g.
Comparative example 5
The fluorescent dye complex of this comparative example 5 and its preparation procedure are the same as in example 4, except that: and (2) performing high-pressure homogenization treatment.
Comparative example 6
The fluorescent dye complex of this comparative example 6 and its preparation procedure are the same as in example 4, except that: step (3) is not performed with ultrasonic treatment.
Comparative example 7
The fluorescent dye complex of this comparative example 7 and its preparation procedure are the same as in example 4, except that: and (4) air drying.
Fluorescence tests were performed on the fluorochrome complexes prepared in examples 1 to 5, comparative example 1 and comparative example 2 described above, and the results correspond to fig. 1 to 7; the fluorochrome compounds prepared in examples 1 to 5 and comparative examples 1 to 7 were subjected to particle size measurement, the results are shown in Table 1, 5g of each sample was dissolved in 100ml of water, and the quick-solubility was measured, and the results are shown in Table 1.
TABLE 1
From fig. 1 to 7 in combination with table 1, it is found that the fluorescent dye compound prepared in examples 1 to 5 of the present invention has good fluorescence intensity, the particle size is smaller, the particle size dispersibility is good, the particle size is relatively one, the average molecular weight of polyethylene glycol in comparative example 1 is smaller than 760 to 840, the fluorescent dye compound can appear as a polymer, the fluorescence intensity is affected, the average molecular weight of polyethylene glycol in comparative example 1 is larger than 760 to 840, the fluorescent dye compound still has good fluorescence intensity, but the particle size of the fluorescent dye compound is larger, the dispersibility is relatively poor, the instant dissolution is unfavorable, the content of polyethylene glycol in comparative example 3 is low, the particle size dispersibility is poor, the instant dissolution is poor, the content of polyethylene glycol in comparative example 4 is high, the fluorescent dye compound has good particle size and dispersibility, the instant dissolution, but the use amount is high, the cost is increased, and from comparative example 5 to comparative example 7, the high-pressure homogenization, the ultrasonic treatment and the spray drying have an effect on the particle size, the particle size dispersibility and the instant dissolution of the fluorescent dye compound, the high-pressure homogenization, the ultrasonic treatment and the spray drying synergy make the fluorescent dye compound have good dispersibility in the fluorescent dye compound and the instant dissolution in water; therefore, the fluorescent dye compound prepared by the process conditions and parameters is preferable, and the mass ratio of the phthalocyanine dye to the polyethylene glycol to the oligopeptide is 1:1.6-1.9:0.6, the average molecular weight of the polyethylene glycol is 760-840, and the fluorescent dye compound has good dispersibility, stability and biocompatibility, and can promote the development and application of the phthalocyanine dye in fluorescent marking and imaging.
Finally, it should be noted that the above-mentioned embodiments are only for illustrating the technical solution of the present invention and not for limiting the technical solution of the present invention, and although the present invention has been described in detail with reference to the above-mentioned embodiments, it should be understood by those skilled in the art that the present invention may be modified or equivalently replaced without departing from the spirit and scope of the present invention, and any modification or partial replacement thereof should be included in the scope of the claims of the present invention.
Claims (6)
1. A fluorescent dye compound is characterized in that the fluorescent dye compound is formed by compounding phthalocyanine dye, polyethylene glycol and oligopeptide-1; the average molecular weight of polyethylene glycol is 760-840;
The preparation method of the fluorescent dye compound comprises the following steps:
(1) Dissolving polyethylene glycol in deionized water, and stirring to obtain a composite solution A;
(2) Adding the phthalocyanine dye into the composite liquid A, mixing, keeping the stirring speed unchanged, heating to 90-95 ℃, preserving heat for 3-4 hours, and carrying out high-pressure homogenization treatment to obtain composite liquid B;
(3) Cooling the composite liquid B to 45-50 ℃, keeping stirring unchanged, adding oligopeptide-1, mixing, preserving heat for 1-2 hours, and performing ultrasonic treatment to obtain composite liquid C;
(4) Concentrating the composite liquid C by reduced pressure rotary evaporation, and spray drying to obtain a fluorescent dye composite;
the mass ratio of the phthalocyanine dye to the polyethylene glycol to the oligopeptide is 1:1.6-1.9:0.6;
Homogenizing under 15MPa;
the structural formula of the phthalocyanine dye is ；
The sequence of oligopeptide-1 is Gly-His-Lys.
2. A fluorescent dye complex according to claim 1, characterized in that the stirring conditions: the stirring speed is 1500-2000 rpm.
3. A fluorescent dye complex according to claim 1, characterized in that the high pressure homogenization conditions: the homogenizing pressure is 15MPa, and the homogenizing time is 20-30 min.
4. A fluorescent dye complex according to claim 1, characterized in that the sonication conditions: the ultrasonic frequency is 10-15 KHz, and the ultrasonic time is 1-2 h.
5. The fluorescent dye complex according to claim 1, wherein the water content after concentration is 40-50%.
6. A fluorescent dye complex according to claim 1, characterized in that the spray drying conditions: the air inlet temperature is 180-200 ℃, and the air outlet temperature is 75-85 ℃.
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|---|---|---|---|---|
| CN107613975A (en) * | 2015-04-20 | 2018-01-19 | 俄勒冈州立大学 | Composition comprising the light-sensitive compound in polymer nanoparticle and the method using said composition |
| CN113613677A (en) * | 2019-10-18 | 2021-11-05 | 犹他大学研究基金会 | Polymeric drug delivery conjugates and methods of making and using the same |
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| CN113943305A (en) * | 2021-11-15 | 2022-01-18 | 中国科学技术大学 | Phthalocyanine fluorescent molecular compound, preparation method and phthalocyanine fluorescent nano material |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008078190A2 (en) * | 2006-12-21 | 2008-07-03 | Universite De Geneve | Compounds for fluorescence imaging |
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| CN107613975A (en) * | 2015-04-20 | 2018-01-19 | 俄勒冈州立大学 | Composition comprising the light-sensitive compound in polymer nanoparticle and the method using said composition |
| CN113613677A (en) * | 2019-10-18 | 2021-11-05 | 犹他大学研究基金会 | Polymeric drug delivery conjugates and methods of making and using the same |
| CN113801190A (en) * | 2020-06-12 | 2021-12-17 | 深圳瑞德林生物技术有限公司 | Method for preparing oligopeptide-1 hydrochloride |
| CN113943305A (en) * | 2021-11-15 | 2022-01-18 | 中国科学技术大学 | Phthalocyanine fluorescent molecular compound, preparation method and phthalocyanine fluorescent nano material |
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| Title |
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| 钟海军等.《药剂学》.华中科技大学出版社,2021,(第1版),第323-324页. * |
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