CN113651911B - 一种通过原子转移自由基聚合制备的近红外二区荧光成像造影剂及其应用 - Google Patents
一种通过原子转移自由基聚合制备的近红外二区荧光成像造影剂及其应用 Download PDFInfo
- Publication number
- CN113651911B CN113651911B CN202110756722.XA CN202110756722A CN113651911B CN 113651911 B CN113651911 B CN 113651911B CN 202110756722 A CN202110756722 A CN 202110756722A CN 113651911 B CN113651911 B CN 113651911B
- Authority
- CN
- China
- Prior art keywords
- contrast agent
- infrared
- fluorescence imaging
- imaging contrast
- region
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000002872 contrast media Substances 0.000 title claims abstract description 62
- 238000000799 fluorescence microscopy Methods 0.000 title claims abstract description 34
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 title claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 239000000178 monomer Substances 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 6
- 238000003384 imaging method Methods 0.000 abstract description 5
- 238000001338 self-assembly Methods 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000002105 nanoparticle Substances 0.000 description 9
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 238000003917 TEM image Methods 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 5
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 4
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000000295 emission spectrum Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 2
- HFQMXANPXOPLQH-UHFFFAOYSA-N CCCCCCCCC1(CCCCCCCC)C(C=C(C=C2)C3=CC=C(C4=CC=C(C5=CC=CS5)S4)S3)=C2C2=CC=CC=C12 Chemical compound CCCCCCCCC1(CCCCCCCC)C(C=C(C=C2)C3=CC=C(C4=CC=C(C5=CC=CS5)S4)S3)=C2C2=CC=CC=C12 HFQMXANPXOPLQH-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 238000012632 fluorescent imaging Methods 0.000 description 2
- 229920003169 water-soluble polymer Polymers 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012984 biological imaging Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000012985 polymerization agent Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000004627 transmission electron microscopy Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F120/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/026—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from the reaction products of polyepoxides and unsaturated monocarboxylic acids, their anhydrides, halogenides or esters with low molecular weight
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (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
本发明属于纳米生物医学成像技术领域,涉及一种高稳定性近红外二区荧光成像造影剂及其制备方法和应用。该水溶性造影剂由近红外二区荧光的有机小分子与水溶性单体通过原子转移自由基聚合而成后自组装而成。本发明制备的造影剂对碱性环境有好的稳定性、良好的水溶性和生物相容性,能够实现高清晰度的近红外二区荧光成像效果。
Description
技术领域
本发明属于纳米生物医学成像技术领域,具体涉及一种通过原子转移自由基聚合制备而成的近红外二区荧光成像造影剂及其应用。
背景技术
近红外二区(900-1700纳米)荧光成像因其具有高穿透深度、低背景噪音和成像信噪比高的优势,今年来开始大量应用于生物成像领域,例如血管成像、心率检测、荧光成像指导的手术切除等。
近年来,多种无机材料、有机小分子和共轭聚合物用于制备近红外二区荧光成像造影剂。其中有机小分子因为具备好的生物相容性、易于合成、可以从生物体内代谢以及可以通过结构的调控获得不同的光学性质,而成为近红外二区荧光成像造影剂的开发热点。电子给体- 电子受体-电子给体(D-A-D)结构的有机小分子是其中最受关注的一类。但是现在开发的此类小分存在碱性和氧化还原环境中易于降解的问题。这种稳定性差的问题还限制了利用原子转移自由基聚合的方法对其进行水溶性聚合物修饰的可能性。
发明内容
目的:本发明提供了一种通过原子转移自由基聚合方法得到的近红外二区荧光成像造影剂,及其制备方法和应用,旨在提高近红外二区荧光成像造影剂在碱性环境中的光稳定性,扩大近红外二区荧光成像造影剂的应用范围,并实现更好的荧光成像效果。
技术方案:为解决上述技术问题,本发明采用的技术方案为:
一种化合物,结构通式如下:
式(1)中,嵌段重复单元数n为5~30,m为5~20。
在一些实施例中,m为5,10或20。对应的水溶性单体分别为:
所述化合物的发光基团为近红外二区荧光染料,为4,6-双(5'-(9,9-二辛基-9H-芴-2-基) -[2,2'-联噻吩]-5-基)噻吩[3,4-C][1,2,5]噻二唑,结构如下所示:
第二方面,提供所述的化合物的制备方法,利用原子转移自由基聚合,原子转移自由基聚合发剂修饰的近红外二区发光的有机分子TTDT-TF-Br与水溶性单体通过原子转移自由基聚合形成,合成路线包括:
在一些实施例中,制备过程中,加入溴化亚铜作为催化剂,五甲基二乙烯三胺作为配体,用苯甲醚作为溶剂;反应温度控制在55-65度,优选为60度左右。
第三方面,提供所述的化合物在制备近红外二区荧光成像造影剂中的应用。
一种近红外二区荧光成像造影剂,将所述化合物直接溶于水中,在水中自组装得到近红外二区荧光成像造影剂。
进一步的,所述近红外二区荧光成像造影剂中化合物的浓度为5~90mg/ml。
进一步的,所述近红外二区荧光成像造影剂在pH值8~12范围内能保持光物理稳定性,不发生分解和近红外二区荧光下降。
有益效果:本发明设计并合成了一种通过原子转移自由基聚合得到的水溶性近红外二区荧光成像造影剂,该造影剂由水溶性的聚合物在水溶液中组装而成。近红外二区荧光成像聚合物的近红外二区发光基团为4,6-双(5'-(9,9-二辛基-9H-芴-2-基)-[2,2'-联噻吩]-5-基)噻吩[3,4-C][1,2,5]噻二唑,四个水溶性侧链为不同结构的聚乙二醇甲基丙烯酸酯。本发明制备方法简单,造影剂具有优异近红外二区成像荧光效果,在pH值8-12范围内和氧化还原条件具有好的光稳定性,不会发生分解。与现在报道的近红外二区荧光成像造影剂相比,该水溶性近红外二区荧光成像造聚合物的制备方法是原子转移自由基聚合,该方法合成简单、高效。
附图说明
图1为本发明实施例1所得造影剂在水溶液中透射电镜照片;
图2为本发明实施例2所得造影剂在水溶液中透射电镜照片;
图3为本发明实施例3所得造影剂在水溶液中透射电镜照片
图4为本发明实施例4所得造影剂的流体力学直径;
图5为本发明实施例5所得造影剂的流体力学直径;
图6为本发明实施例6所得造影剂的流体力学直径;
图7为本发明实施例2所得造影剂在不同pH值环境下的吸收与荧光光谱图谱;
图8为本发明实施例3所得造影剂在氧化还原环境下的吸收与荧光光谱图谱;
图9为本发明实施例6所得造影剂对小鼠活体4T1肿瘤的近红外二区荧光成像。
具体实施方式
为了进一步阐明本发明,下面给出一系列实施例,这些实施例完全是例证性的,它们仅用来对本发明具体描述,不应当理解为对本发明的限制。
水溶性近红外二区荧光成像聚合物的合成方法:
当m=5时,近红外二区荧光成像聚合物的合成路线为:
合成过程
取5毫升反应瓶,加入引发剂TTDT-TF-Br(648毫克,0.33毫摩尔),聚乙二醇甲基丙烯酸酯单体(2.16克,6.6毫摩尔),溴化亚铜(189毫克,1.32毫摩尔),用苯甲醚溶解(2 毫升),除氧后,加入五甲基二乙烯三胺(228毫克,1.32毫摩尔),60摄氏度条件下反应8 小时。之后用乙醚进行沉降,得红褐色粘稠液体。
调整上述步骤单体的比例,即可得到嵌段重复单元数n为5-30的水溶性近红外二区荧光成像聚合物。
当m=10时,近红外二区荧光成像聚合物的合成路线为:
合成过程
取5毫升反应瓶,加入引发剂TTDT-TF-Br(648毫克,0.33毫摩尔),聚乙二醇甲基丙烯酸酯单体(4.32克,6.6毫摩尔)、溴化亚铜(189毫克,1.32毫摩尔),用苯甲醚溶解(2 毫升),除氧后,加入五甲基二乙烯三胺(228毫克,1.32毫摩尔),60摄氏度条件下反应8 小时。之后用乙醚进行沉降,得红褐色粘稠液体。
调整上述步中单体的比例,即可得到嵌段重复单元数n为5-30的水溶性近红外二区荧光成像聚合物。
当m=20时,近红外二区荧光成像聚合物的合成路线为:
合成过程
取5毫升反应瓶,加入引发剂TTDT-TF-Br(648毫克,0.33毫摩尔),聚乙二醇甲基丙烯酸酯单体(8.64克,6.6毫摩尔)、溴化亚铜(189毫克,1.32毫摩尔),用苯甲醚溶解(2 毫升),除氧后,加入五甲基二乙烯三胺(228毫克,1.32毫摩尔),60摄氏度条件下反应8 小时。之后用乙醚进行沉降,得红褐色粘稠液体。
调整上述过程中单体的比例,即可得到嵌段重复单元数n为5-30的水溶性近红外二区荧光成像聚合物。
实施例1:
m=5、嵌段重复单元数n为5的聚合物50毫克溶于5毫升水中自组装即可得造影剂。
如图1所示,测试造影剂在水溶液中的透射电镜图,可得该造影剂纳米粒子粒径为100-110纳米,且都为类球形。
实施例2:
m=10、嵌段重复单元数n为10的聚合物50毫克溶于5毫升水中自组装即可得造影剂。
如图2所示,测试造影剂在水溶液中的透射电镜图,可得该造影剂纳米粒子粒径为110-115 纳米,且都为类球形。
如图7所示,测试造影剂的吸收与发射光谱图,可以看出其紫外-近红外吸收在700-900 纳米范围,而发射峰1000纳米以上,具有明显的二窗荧光发射。并且造影剂在不同pH值的溶液中具有较好的光稳定性。
实施例3:
m=20、嵌段重复单元数n为20的聚合物50毫克溶于5毫升水中自组装即可得造影剂。
如图3所示,测试造影剂在水溶液中的透射电镜图,可得该造影剂纳米粒子粒径为115-120纳米,且都为类球形。
如图8所示,测试造影剂的吸收与发射光谱图,可以看出其紫外-近红外吸收在700-900 纳米范围,而发射峰1000纳米以上,具有明显的近红外二区荧光发射。并且造影剂在氧化还原环境中具有较好的光稳定性。
实施例4:
m=5、嵌段重复单元数n为5的聚合物100毫克溶于5毫升水中自组装即可得造影剂。
如图4所示,测试造影剂在水溶液中的流体力学直径,可得该造影剂纳米粒子粒径为125 纳米。
实施例5:
m=5、嵌段重复单元数n为5的聚合物200毫克溶于5毫升水中自组装即可得造影剂。
如图5所示,测试造影剂在水溶液中的流体力学直径,可得该造影剂纳米粒子粒径为130 纳米。
实施例6:
m=5、嵌段重复单元数n为5的聚合物400毫克溶于5毫升水中自组装即可得造影剂。
如图6所示,测试造影剂在水溶液中的流体力学直径,可得该造影剂纳米粒子粒径为128 纳米。
如图9所示,选用4T1肿瘤小鼠模型,尾静脉注射200微升,用近红外二区成像仪观察其小鼠肿瘤位置的信号强度变化图,可以看出随着时间的延长肿瘤的成像越来越明显,在12 小时到达最大值,随后随时间的延长信号强度开始减弱。
以上所述仅是本发明的优选实施方式,应当指出:对于本技术领域的普通技术人员来说,在不脱离本发明原理的前提下,还可以做出若干改进和润饰,这些改进和润饰也应视为本发明的保护范围。
Claims (6)
2.根据权利要求1所述的近红外二区荧光成像造影剂,其特征在于,m为5。
3.根据权利要求1所述的近红外二区荧光成像造影剂,其特征在于,m为10。
4.根据权利要求1所述的近红外二区荧光成像造影剂,其特征在于,m为20。
6.根据权利要求1所述的近红外二区荧光成像造影剂,其特征在于,所述近红外二区荧光成像造影剂中化合物的浓度为5~90mg/ml。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110756722.XA CN113651911B (zh) | 2021-07-05 | 2021-07-05 | 一种通过原子转移自由基聚合制备的近红外二区荧光成像造影剂及其应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110756722.XA CN113651911B (zh) | 2021-07-05 | 2021-07-05 | 一种通过原子转移自由基聚合制备的近红外二区荧光成像造影剂及其应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113651911A CN113651911A (zh) | 2021-11-16 |
CN113651911B true CN113651911B (zh) | 2022-07-26 |
Family
ID=78477963
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202110756722.XA Active CN113651911B (zh) | 2021-07-05 | 2021-07-05 | 一种通过原子转移自由基聚合制备的近红外二区荧光成像造影剂及其应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN113651911B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114426554A (zh) * | 2022-01-07 | 2022-05-03 | 西藏大学 | 有机荧光小分子化合物、有机荧光纳米载体及其制备方法和应用 |
CN114573621B (zh) * | 2022-01-19 | 2023-07-07 | 南京邮电大学 | 一种苯硼酸修饰的水溶性近红外二区荧光造影剂及其应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109593145A (zh) * | 2018-12-12 | 2019-04-09 | 合肥工业大学 | 一种具有核磁造影功能的环状聚合物及其制备方法和应用 |
CN112409384A (zh) * | 2020-11-18 | 2021-02-26 | 南京邮电大学 | 双噻吩噻二唑受体近红外二区荧光分子及其制备方法和应用 |
CN112851842A (zh) * | 2021-01-18 | 2021-05-28 | 南京邮电大学 | 一种小尺寸近红外二区荧光成像造影剂及其制备方法和应用 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111518545B (zh) * | 2020-04-20 | 2022-03-15 | 苏州大学 | 高稳定性近红外二区纳米荧光探针及其制备方法和应用 |
-
2021
- 2021-07-05 CN CN202110756722.XA patent/CN113651911B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109593145A (zh) * | 2018-12-12 | 2019-04-09 | 合肥工业大学 | 一种具有核磁造影功能的环状聚合物及其制备方法和应用 |
CN112409384A (zh) * | 2020-11-18 | 2021-02-26 | 南京邮电大学 | 双噻吩噻二唑受体近红外二区荧光分子及其制备方法和应用 |
CN112851842A (zh) * | 2021-01-18 | 2021-05-28 | 南京邮电大学 | 一种小尺寸近红外二区荧光成像造影剂及其制备方法和应用 |
Non-Patent Citations (6)
Title |
---|
A highly water-soluble triblock conjugated polymer for in vivo NIR-II imaging and photothermal therapy of cancer;Xiaomei Lu等;《Polymer Chemistry》;20180509;3118-3126 * |
Amphiphilic multiarm star block copolymer-based multifunctional unimolecular micelles for cancer targeted drug delivery and MR imaging;Xiaojie Li;《Biomaterials》;20110612;120916:1-12 * |
Gamze Koçal等.Stimuli-responsive smart nanoparticles with well-defined random and triblock terpolymers for controlled release of an anticancer drug.《Materials Today Communications》.2020, * |
Starlike polymer brush-based ultrasmall nanoparticles with simultaneously improved NIR-II fluorescence and blood circulation for efficient orthotopic glioblastoma imaging;Shangyu Chen等;《Biomaterials》;20210601;6595-6605 * |
Thienothiadiazole-Based NIR-II Dyes with D−A−D Structure for NIRII Fluorescence Imaging Systems;Pengfei Sun等;《ACS Appl. Bio Mater.》;20210429;4542-4548 * |
共轭聚合物近红外二区光诊疗剂的制备及肿瘤成像与治疗应用;孙晓莉;《中国优秀博硕士学位论文全文数据库(硕士) 工程科技I辑》;20210215;B016-2539:1-87 * |
Also Published As
Publication number | Publication date |
---|---|
CN113651911A (zh) | 2021-11-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN113651911B (zh) | 一种通过原子转移自由基聚合制备的近红外二区荧光成像造影剂及其应用 | |
CN112851842B (zh) | 一种小尺寸近红外二区荧光成像造影剂及其制备方法和应用 | |
CN112409384B (zh) | 双噻吩噻二唑受体近红外二区荧光分子及其制备方法和应用 | |
Sun et al. | Bright fluorescent nanoparticles for developing potential optical imaging contrast agents | |
CN110041475B (zh) | 一种两亲性嵌段共聚物、其壳交联胶束及制备方法和应用 | |
CN110997012A (zh) | 用于余辉分子成像的聚合物纳米颗粒 | |
Su et al. | A design strategy for D–A conjugated polymers for NIR-II fluorescence imaging | |
CN109824871B (zh) | 一种近红外二区荧光醌式聚合物、制备方法及其应用 | |
CN109320636B (zh) | 三重刺激响应性核交联聚合物胶束及其制备方法和应用 | |
CN114455567A (zh) | 一种碳纳米粒子的制备方法及应用 | |
Bai et al. | Reduction-responsive dithiomaleimide-based polymeric micelles for controlled anti-cancer drug delivery and bioimaging | |
CN108912327B (zh) | 一种水溶性非共轭结构的可降解活细胞荧光成像材料及其制备方法和应用 | |
CN111569068A (zh) | 一种有机无机杂化光敏剂及杂化纳米诊疗试剂的制备方法 | |
CN113912762B (zh) | 水溶性的近红外二区大分子荧光探针及其制备方法和应用 | |
CN114316084B (zh) | Aie功能化可荧光示踪的改性甲壳素材料、制备方法和应用 | |
Yang et al. | J-Aggregation induced NIR-II fluorescence: an aza-BODIPY luminogen for efficient phototheranostics | |
CN111012911B (zh) | 海藻酸钠在作为抗肿瘤药物靶向载体中的应用 | |
CN113262309B (zh) | 一种负载抗肿瘤药物的超支化-嵌段共接枝药物载体及其制备方法和应用 | |
CN114621746A (zh) | 一种余辉发光纳米材料及其制备方法与应用 | |
Wang et al. | A strategy for prompt phase transfer of upconverting nanoparticles through surface oleate-mediated supramolecular assembly of amino-β-cyclodextrin | |
CN115894896B (zh) | 一种长循环近红外二区荧光成像造影剂、制备方法及应用 | |
KR100810679B1 (ko) | 금 나노입자를 이용한 엑스-선 조영제 및 이의 제조방법 | |
CN114870014B (zh) | 一种多功能抗肿瘤高分子药物及其制备方法和用途 | |
CN114573621B (zh) | 一种苯硼酸修饰的水溶性近红外二区荧光造影剂及其应用 | |
CN111909386B (zh) | 一种共轭聚合物-有机金属框架复合纳米材料及其制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |