146368-08-3Relevant articles and documents
Evaluation of asymmetric orthogonal cyanine fluorophores
Boutkan, Michael S.,Buckle, Tessa,Hensbergen, Albertus W.,Welling, Mick M.,Wester, Hans-Jürgen,de Kleer, Mathijs A. C.,van Leeuwen, Fijs W. B.,van Willigen, Danny M.,van der Wijk, Felicia A.
, (2020)
Pentamethine cyanine (Cy5) fluorophores have proven to be versatile imaging agents (i.e., tracers) for a range of micro- and macroscopic imaging applications, including image-guided surgery. In this study the relationship between the structure of asymmetric Cy5 fluorophores and their photophysical properties was studied. To this end, seven Cy5 analogues, bearing orthogonal N-indole substituents (H, SO3?, or benzene), were synthesised and evaluated. In-depth analysis revealed that introduction of sulfonates enhanced the fluorescence brightness and photostability, while reducing the lipophilicity, serum binding and stacking tendency. The addition of benzene moieties induced a bathochromic shift of 10–20 nm, increased the lipophilicity (LogP = -1.56–1.23) and serum binding (67.3–93.8percent bound), as well as negatively impacted the brightness (0.74–42.9 · 103 M?1 cm?1), photostability (24.4–90.6percent remaining), and stacking tendency. Chemical stability was uninfluenced by the substitution pattern. Additionally, the generation of a c[RGDyK]-based hybrid tracer based on one of these fluorophores in combination with a diethylenetriaminepentaacetic acid (DTPA) chelate and an 111In-isotope was reported. This compound was evaluated in vitro using αvβ3-overexpressing Geβ3 cells and in vivo using a 4T1 mouse tumour model. Overall, the presented results imply that alterations of the asymmetrical orthogonal Cy5 fluorophore structure have impact on the (photo)physical properties. Furthermore, the orthogonal Cy5 fluorophore framework can readily be applied in tracer development.
A genetically encoded isonitrile lysine for orthogonal bioorthogonal labeling schemes
Biró, Adrienn,Cserép, Gergely B.,Kele, Péter,Molnár, Tibor á.,Németh, Krisztina,S?veges, Bianka,Szabó, Edit,Szatmári, ágnes,Várady, Gy?rgy
supporting information, (2021/08/26)
Bioorthogonal click-reactions represent ideal means for labeling biomolecules selectively and specifically with suitable small synthetic dyes. Genetic code expansion (GCE) technology enables efficient site-selective installation of bioorthogonal handles o
Sulfo - Cy3 carboxylic acid fluorescent dye and preparation process thereof
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Paragraph 0014; 0016, (2021/10/05)
The invention relates to a sulfo - Cy3 carboxylic acid fluorescent dye and a preparation process thereof, wherein the synthesized sulfo - Cy3 carboxylic acid has fluorescent quantum yield. At the same time, the high-emission high-excitation wavelength and is easily dissolved in water physical and chemical property stability points, and simultaneously, a single condensation target product needs to be selectively generated when the indole α-position methyl activity is achieved through simultaneous construction of the benzylindole two-side branch chains and high in yield, and C18 column separation is avoided.
COMPOUNDS AND COMPOSITIONS FOR RETINAL INJURY DETECTION AND METHODS OF USING SAME
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Paragraph 0087, (2021/08/13)
Described are compounds, compositions, and methods suitable for diagnosing individuals with eye injuries and/or diseases. The compounds of the present disclosure have fluorescent groups and bis-dipicolylamine groups, which may be substituted or unsubstituted. The fluorescent group and bis-dipicolylamine group are connected by linking groups. The compositions may be formulated and administered as an eye drop. The methods may be used to track and/or label dying cells associated with eye injuries and/or diseases, such as, for example, retinal degenerations including, but not limited to, retinitis pigmentosa, glaucoma, diabetic retinopathy, and age-related macular degeneration.
Rapid and Selective Labeling of Endogenous Transmembrane Proteins in Living Cells with a Difluorophenyl Ester Affinity-Based Probe
Chan, Hsin-Ju,Lin, Xin-Hui,Fan, Syuan-Yun,Ru Hwu, Jih,Tan, Kui-Thong
supporting information, p. 3416 - 3420 (2020/10/02)
The long-term stability of affinity-based protein labeling probes is crucial to obtain reproducible protein labeling results. However, highly stable probes generally suffer from low protein labeling efficiency and pose significant challenges when labeling low abundance native proteins in living cells. In this paper, we report that protein labeling probes based on an ortho-difluorophenyl ester reactive module exhibit long-term stability in DMSO stock solution and aqueous buffer, yet they can undergo rapid and selective labeling of native proteins. This novel electrophile can be customized with a wide range of different protein ligands and is particularly well-suited for the labeling and imaging of transmembrane proteins. With this probe design, the identity and relative levels of basal and hypoxia-induced transmembrane carbonic anhydrases were revealed by live cell imaging and in-gel fluorescence analysis. We believe that the extension of this difluorophenyl ester reactive module would allow for the specific labeling of various endogenous membrane proteins, facilitating in-depth studies of their distribution and functions in biological processes.
IMAGING AGENTS
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Paragraph 0111; 0118, (2020/04/30)
This invention relates to compounds of formula I or la: Y1 is -EuK, -EuFA, -EuPG, -L1-EuK, -L1-EuFA, -L1-EuPG or -L3-EuE; Y2 is -L4-EuK, - L4-EuFA, - L4-EuPG, -EuE, or -L2-EuE; Z is a chelating moiety; and the other substituents are as defined herein. Also provided are formulations comprising such a compound, as well as methods of imaging or methods for the treatment of cancer comprising use of such a compound or formulation.
High-Yielding Water-Soluble Asymmetric Cyanine Dyes for Labeling Applications
Wolf, Natalia,Kersting, Louise,Herok, Christoph,Mihm, Cornelius,Seibel, Juergen
supporting information, p. 9751 - 9760 (2020/09/03)
A simple and efficient microwave-assisted synthesis of asymmetric pentamethine cyanine dyes with various functional groups was developed, which allows high-yielding results. The synthesized dyes are modifiable and suitable for single-molecule imaging in biological and medical sciences by application of click chemistry or classic esterification and amidation.
S - Cis Diene Conformation: A New Bathochromic Shift Strategy for Near-Infrared Fluorescence Switchable Dye and the Imaging Applications
Chen, Hsiang-Jung,Chew, Chee Ying,Chang, En-Hao,Tu, Yu-Wei,Wei, Li-Yu,Wu, Bo-Han,Chen, Chien-Hung,Yang, Ya-Ting,Huang, Su-Chin,Chen, Jen-Kun,Chen, I-Chia,Tan, Kui-Thong
supporting information, p. 5224 - 5234 (2018/04/23)
In this paper, we present a novel charge-free fluorescence-switchable near-infrared (IR) dye based on merocyanine for target specific imaging. In contrast to the typical bathochromic shift approach by extending π-conjugation, the bathochromic shift of our merocyanine dye to the near-IR region is due to an unusual S-cis diene conformer. This is the first example where a fluorescent dye adopts the stable S-cis conformation. In addition to the novel bathochromic shift mechanism, the dye exhibits fluorescence-switchable properties in response to polarity and viscosity. By incorporating a protein-specific ligand to the dye, the probes (for SNAP-tag and hCAII proteins) exhibited dramatic fluorescence increase (up to 300-fold) upon binding with its target protein. The large fluorescence enhancement, near-IR absorption/emission, and charge-free scaffold enabled no-wash and site-specific imaging of target proteins in living cells and in vivo with minimum background fluorescence. We believe that our unconventional approach for a near-IR dye with the S-cis diene conformation can lead to new strategies for the design of near-IR dyes.
FLUORESCENCE COMPOUNDS AND PREPARATION METHOD THEREOF
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Paragraph 0148; 0149; 0150; 0151; 0152, (2017/11/16)
Provided is a fluorescent compound represented by the following [Chemical Formula 1] and a method for preparing the same: wherein each of X, Y, R1, R2, R3 and n is the same as defined in the specification.
NOVEL CYANINE COMPOUND FOR LABELING BIOMOLECULE AND PREPARATION METHOD THEREOF
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Paragraph 0232; 0241-0243, (2017/09/14)
The present invention relates to a novel cyanine compound which is represented by chemical formula 1, and is used for biomolecular labeling. The present invention further relates to a production method thereof. In the chemical formula 1, R_1, R_2, R_3, R_4, B, m, and n are the same as defined in the present specification.COPYRIGHT KIPO 2017
