- Heptamethine indocyanine dye as well as preparation method and application thereof
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The invention provides a heptamethine indocyanine dye as well as a preparation method and an application thereof, and belongs to the technical field of fine chemical engineering. The heptamethine indocyanine dye provided by the invention has a structure a
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Paragraph 0131-0136
(2021/10/05)
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- Near-Infrared Fluorescent Micelles from Poly(norbornene) Brush Triblock Copolymers for Nanotheranostics
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This contribution describes the design and synthesis of multifunctional micelles based on amphiphilic brush block copolymers (BBCPs) for imaging and selective drug delivery of natural anticancer compounds. Well-defined BBCPs were synthesized via one-pot multi-step sequential grafting-through ring-opening metathesis polymerization (ROMP) of norbornene-based macroinitiators. The norbornenes employed contain a poly(ethylene glycol) methyl ether chain, an alkyl bromide chain, and/or a near-infrared (NIR) fluorescent cyanine dye. After block copolymerization, post-polymerization transformations using bromide-azide substitution, followed by the strain-promoted azide-alkyne cycloaddition (SPAAC) allowed for the functionalization of the BBCPs with the piplartine (PPT) moiety, a natural product with well-documented cytotoxicity against cancer cell lines, via an ester linker between the drug and the polymer side chain. The amphiphilic BBCPs self-assembled in aqueous media into nano-sized spherical micelles with neutral surface charges, as confirmed by dynamic light scattering analysis and transmission electron microscopy. During self-assembly, paclitaxel (PTX) could be effectively encapsulated into the hydrophobic core to form stable PTX-loaded micelles with high loading capacities and encapsulation efficiencies. The NIR fluorescent dye-containing micelles exhibited remarkable photophysical properties, excellent colloidal stability under physiological conditions, and a pH-induced disassembly under slightly acidic conditions, allowing for the release of the drug in a controlled manner. The in vitro studies demonstrated that the micelles without the drug (blank micelles) are biocompatible at concentrations of up to 1 mg mL-1 and present a high cellular internalization capacity toward MCF-7 cancer cells. The drug-functionalized micelles showed in vitro cytotoxicity comparable to free PPT and PTX against MCF-7 and PC3 cancer cells, confirming efficient drug release into the tumor environment upon cellular internalization. Furthermore, the drug-functionalized micelles exhibited higher selectivity than the pristine drugs and preferential cellular uptake in human cancer cell lines (MCF-7 and PC3) when compared to the normal breast cell line (MCF10A). This study provides an efficient strategy for the development of versatile polymeric nanosystems for drug delivery and image-guided diagnostics. Notably, the easy functionalization of BBCP side chains via SPAAC opens up the possibility for the preparation of a library of multifunctional systems containing other drugs or functionalities, such as target groups for recognition.
- Braga, Carolyne B.,Pilli, Ronaldo A.,Ornelas, Catia,Weck, Marcus
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p. 5290 - 5306
(2021/11/30)
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- Ligand taking indocyanine green derivative as carrier as well as preparation method and application of ligand
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The invention discloses a ligand taking an indocyanine green derivative as a carrier as well as a preparation method and application of the ligand. When the ligand is chelated with paramagnetic metal ions, an NIR/MRI multi-mode contrast agent is obtained, when the ligand is chelated with radioactive metal ions, an NIR/PET multi-mode contrast agent is obtained, and the obtained contrast agents can be used for diagnosis of various tumors, especially liver cancer. Meanwhile, the contrast agents are good in water solubility and low in toxicity, mutual verification of multiple contrast modes is achieved, diagnosis information is enriched, diagnosis precision is improved, and a feasible novel contrast agent is provided for early diagnosis of tumors clinically.
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Paragraph 0212; 0215; 0220-0221; 0280; 0283; 0287-0288
(2021/06/23)
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- NIR/PET bimodal contrast agent, and preparation method and application thereof
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The invention discloses a near infrared and positron emission computed tomography (NIR)/positron emission tomography (PET) bimodal contrast agent, and a preparation method and application thereof. The NIR/PET bimodal contrast agent is obtained by taking an optimized indocyanine green derivative as a carrier and connecting a PET signal molecule. The contrast agent can be used for near-infrared imaging and has PET imaging capability; and meanwhile, the contrast agent is good in water solubility and low in toxicity, near-infrared and PET images verify each other, diagnosis information is enriched, and the contrast agent has the potential of becoming a novel tumor contrast agent.
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Paragraph 0176-0179; 0182-0185
(2021/07/24)
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- NIR/MRI bimodal contrast agent, and preparation method and application thereof
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The invention discloses a near infrared imaging and nuclear magnetic resonance imaging (NIR)/MRI bimodal contrast agent, and a preparation method and application thereof. The NIR/MRI bimodal contrast agent is obtained by taking an optimized indocyanine green derivative as a carrier and connecting an MRI signal molecule. The contrast agent can be used for near-infrared imaging and also has an MRI imaging capability; and meanwhile, water solubility is good, toxicity is low, near-infrared and MRI images verify each other, diagnosis information is enriched, and the contrast agent has the potential of becoming a novel tumor contrast agent.
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Paragraph 0172-0180
(2021/07/24)
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- Renal clearable tumor-specific fluorophores and their imaging methods
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The present invention relates to a tumor-specific fluorescence contrast agent. Specifically, the present invention relates to: a renal excretion-type fluorescence contrast agent which can exhibit a high signal-to-background ratio when optically observing
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Paragraph 0030
(2019/12/15)
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- Biodegradable and pH-Responsive Acetalated Dextran (Ac-Dex) Nanoparticles for NIR Imaging and Controlled Delivery of a Platinum-Based Prodrug into Cancer Cells
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Nanoparticles (NPs) based on the biodegradable acetalated dextran polymer (Ac-Dex) were used for near-infrared (NIR) imaging and controlled delivery of a PtIV prodrug into cancer cells. The Ac-Dex NPs loaded with the hydrophobic PtIV prodrug 3 (PtIV/Ac-Dex NPs) and with the novel hydrophobic NIR-fluorescent dye 9 (NIR-dye 9/Ac-Dex NPs), as well as Ac-Dex NPs coloaded with both compounds (coloaded Ac-Dex NPs), were assembled using a single oil-in-water nanoemulsion method. Dynamic light scattering measurements and scanning electron microscopy images showed that the resulting Ac-Dex NPs are spherical with an average diameter of 100 nm, which is suitable for accumulation in tumors via the enhanced permeation and retention effect. The new nanosystems exhibited high drug-loading capability, high encapsulation efficiency, high stability in physiological conditions, and pH responsiveness. Drug-release studies clearly showed that the PtIV prodrug 3 release from Ac-Dex NPs was negligible at pH 7.4, whereas at pH 5.5, this compound was completely released with a controlled rate. Confocal laser scanning microscopy unambiguously showed that the NIR-dye 9/Ac-Dex NPs were efficiently taken up by MCF-7 cells, and cytotoxicity assays against several cell lines showed no significant toxicity of blank Ac-Dex NPs up to 1 mg mL-1. The IC50 values obtained for the PtIV prodrug encapsulated in Ac-Dex NPs were much lower when compared with the IC50 values obtained for the free PtIV complex and cisplatin in all cell lines tested. Overall, our results demonstrate, for the first time, that Ac-Dex NPs constitute a promising drug delivery platform for cancer therapy.
- Braga, Carolyne B.,Perli, Gabriel,Becher, Tiago B.,Ornelas, Catia
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p. 2083 - 2094
(2019/04/16)
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- Introduction of various substitutions to the methine bridge of heptamethine cyanine dyes: Via substituted dianil linkers
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The unique optical properties of cyanine dyes have prompted their use in numerous applications. Heptamethine cyanines are commonly modified on the methine bridge after synthesis of a meso-chlorine containing cyanine. Herein, a series of heptamethine cyanines containing modified methine bridges were synthesized using substituted dianil linkers. Their optical properties including, molar absorptivity, fluorescence, and quantum yield were measured as well as their hydrophobic effects in polar buffer solution. It was shown that dyes containing cyclopentene in the methine bridge or a phenyl ring in the meso position display increased molar absorptivity while the increased flexibility of the dye containing a cycloheptene in the methine bridge prevented fluorescence.
- Levitz, Andrew,Marmarchi, Fahad,Henary, Maged
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p. 1409 - 1416
(2018/10/21)
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- Dye compound and preparation method thereof
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The present invention relates to a dye compound which maintains initial fluorescence properties even after storage for a long period of time after being labeled on a biomolecule and thus has excellent storage stability, and a method for manufacturing the same. The dye compound according to the present invention not only maintains the initial fluorescence properties even after storage for a long time after being labeled on a biomolecule such as a protein or an antibody, but also exhibits an excellent effect in terms of storage stability such as temperature and moisture.(AA) Compound 1COPYRIGHT KIPO 2018
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Paragraph 0055; 0073; 0074; 0077
(2019/01/11)
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- Switching fluorescent nanoparticle probe and fluorescent particle imaging method using same
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The present invention provides a novel fluorescent nanoparticle imaging probe having a switching function (a function to quench a fluorescent dye during nanoparticle preparation, and emit fluorescence during imaging). A switching fluorescent nanoparticle probe comprising: a molecular assembly composed of an amphiphilic block polymer having a hydrophilic block chain and a hydrophobic block chain; and a fluorescent dye encapsulated in the molecular assembly, wherein (a) the hydrophilic block chain comprises, as an essential hydrophilic structural unit, a unit selected from a sarcosine unit and an alkylene oxide unit, (b) the hydrophobic block chain comprises, as an essential hydrophobic structural unit, a unit selected from the group consisting of an amino acid unit and a hydroxylic acid unit, and (c) the fluorescent dye is a cyanine compound represented by the formula (I): and two or more molecules of the fluorescent dye are encapsulated in the single molecular assembly.
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Page/Page column 23; 24
(2016/07/27)
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- Recognition of saccharides in the NIR region with a novel fluorogenic boronolectin: in vitro and live cell labeling
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This work describes a novel mono-boronic acid derivative of a tricarbocyanine. The probe is a genuine near-infrared fluorescence emitter with improved properties such as a large Stokes shift, excellent water solubility and sensitive fluorogenicity upon bi
- Samaniego Lopez, Cecilia,Lago Huvelle, María Amparo,Uhrig, María Laura,Coluccio Leskow, Federico,Spagnuolo, Carla C.
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supporting information
p. 4895 - 4898
(2015/03/18)
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- SWITCHING-TYPE FLUORESCENT NANOPARTICLE PROBE, AND FLUORESCENT MOLECULAR IMAGING METHOD USING SAME
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[Abstract] [Problem] To provide a novel fluorescent nanoparticle imaging probe having a switching function (a function to quench a fluorescent dye in a blood component and emit fluorescence in a tumor or an inflamed site to be imaged). [Solution] A fluore
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Paragraph 0140
(2014/01/18)
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- Promising near-infrared non-targeted probes: Benzothiazole heptamethine cyanine dyes
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A series of benzothiazole heptamethine cyanine dyes have been synthesized and their photophysical properties evaluated in relation to their structural features. These have been compared against two classical probes of this type: Indocyanine Green (IGC) and New Indocyanine Green (IR-820). Growth inhibitory studies were also performed using a eukaryotic, unicellular organism, fission yeast Schizosaccharomyces pombe. Herein we highlight some potentially interesting candidates with improved fluorescence quantum yields when compared with ICG and IR-820.
- Okoh, Okoh Adeyi,Bisby, Roger H.,Lawrence, Clare L.,Rolph, Carole E.,Smith, Robert B.
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- SWITCHING FLUORESCENT NANOPARTICLE PROBE AND FLUORESCENT PARTICLE IMAGING METHOD USING SAME
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The present invention provides a novel fluorescent nanoparticle imaging probe having a switching function (a function to quench a fluorescent dye during nanoparticle preparation, and emit fluorescence during imaging). A switching fluorescent nanoparticle probe comprising: a molecular assembly composed of an amphiphilic block polymer having a hydrophilic block chain and a hydrophobic block chain; and a fluorescent dye encapsulated in the molecular assembly, wherein (a) the hydrophilic block chain comprises, as an essential hydrophilic structural unit, a unit selected from a sarcosine unit and an alkylene oxide unit, (b) the hydrophobic block chain comprises, as an essential hydrophobic structural unit, a unit selected from the group consisting of an amino acid unit and a hydroxylic acid unit, and (c) the fluorescent dye is a cyanine compound represented by the formula (I): and two or more molecules of the fluorescent dye are encapsulated in the single molecular assembly.
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Paragraph 0135
(2013/06/27)
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- Development of novel nanocarrier-based near-infrared optical probes for in vivo tumor imaging
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Optical imaging with near-infrared (NIR) fluorescent probes is a useful diagnostic technology for in vivo tumor detection. Our plan was to develop novel NIR fluorophoremicelle complex probes. IC7-1 and IC7-2 were synthesized as novel lipophilic NIR fluorophores, which were encapsulated in an amphiphilic polydepsipeptide micelle lactosome . The fluorophore-micelle complexes IC7-1 lactosome and IC7-2 lactosome were evaluated as NIR fluorescent probes for in vivo tumor imaging. IC7-1 and IC7-2 were synthesized and then encapsulated in lactosomes. The optical properties of IC7-1, IC7-2, IC7-1 lactosome and IC7-2 lactosome were measured. IC7-1 lactosome and IC7-2 lactosome were administered to tumor-bearing mice, and fluorescence images were acquired for 48 h. IC7-1 and IC7-2 were successfully synthesized in 12% and 6.3% overall yield, and maximum emission wavelengths in chloroform were observed at 858 nm and 897 nm, respectively. Aqueous buffered solutions of IC7-1 lactosome and IC7-2 lactosome showed similar fluorescence spectra in chloroform and higher or comparable quantum yields and higher photostability compared with ICG. Both lactosome probes specifically visualized tumor tissue 6 h post-administration. IC7-1 lactosome and IC7-2 lactosome could be promising NIR probes for in vivo tumor imaging. Springer Science+Business Media, LLC 2011.
- Shimizu, Yoichi,Temma, Takashi,Hara, Isao,Yamahara, Ryo,Ozeki, Ei-Ichi,Ono, Masahiro,Saji, Hideo
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experimental part
p. 719 - 727
(2012/08/29)
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- Combining aminocyanine dyes with polyamide dendrons: A promising strategy for imaging in the near-infrared region
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Cyanine dyes are known for their fluorescence in the near-IR (NIR) region, which is desirable for biological applications. We report the synthesis of a series of aminocyanine dyes containing terminal functional groups such as acid, azide, and cyclooctyne groups for further functionalization through, for example, click chemistry. These aminocyanine dyes can be attached to polyfunctional dendrons by copper-catalyzed azide alkyne cycloaddition (CuAAC), strain-promoted azide alkyne cycloaddition (SPAAC), peptide coupling, or direct SNR1 reactions. The resulting dendron-dye conjugates were obtained in high yields and displayed high chemical stability and photostability. The optical properties of the new compounds were studied by UV/Vis and fluorescence spectroscopy. All compounds show large Stokes shifts and strong fluorescence in the NIR region with high quantum yields, which are optimal properties for in vivo optical imaging.
- Ornelas, Catia,Lodescar, Rachelle,Durandin, Alexander,Canary, James W.,Pennell, Ryan,Liebes, Leonard F.,Weck, Marcus
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p. 3619 - 3629
(2011/05/05)
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- Symmetric, monofunctionalised polymethine dyes labelling reagents
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A symmetric cyanine of the formula: wherein:X is selected from the group consisting of O, S and C(CH3)2;W represents non-metal atoms required to form a benzo-condensed or a naphto-condensed ring;R1 is selected from the gro
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- Symmetric, monofunctionalised polymethine dyes labelling reagents
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A symmetric cyanine of the formula: wherein:X is selected from the group consisting of O, S and C(CH3)2;W represents non-metal atoms required to form a benzo-condensed or a naphto-condensed ring;R1 is selected from the group consisting of (CH2)nCH3, (CH2)nSO3- and (CH2)nSO3H, wherein n is an integer selected from 0 to 6 when R1 is (CH2)nCH3, and n is an integer selected from 3 to 6 when R1 is (CH2)nSO3- or (CH2)nSO3H;R2 and R3 are independently selected from the group consisting of H, a sulphonic moiety and a sulphonate moiety;Q is selected from the group consisting of:wherein q is 0 or 1 and D is selected from the group consisting of:-C≡C-G; andwherein A is O or S and G is, or contains a N, O or S nucleophile moiety or is, or contains a moiety capable of reacting with N, O or S nucleophiles.
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- Symmetric, monofunctionalised polymethine dyes labelling reagents
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A symmetric cyanine of the formula: wherein: X is selected from the group consisting of O, S and C(CH3)2; W represents non-metal atoms required to form a benzo-condensed or a naphto-condensed ring; R1 is selected from the
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