- Evaluation of asymmetric orthogonal cyanine fluorophores
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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.
- 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.
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Read Online
- COMPOUNDS AND COMPOSITIONS FOR RETINAL INJURY DETECTION AND METHODS OF USING SAME
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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.
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Paragraph 0087
(2021/08/13)
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- Sulfo - Cy3 carboxylic acid fluorescent dye and preparation process thereof
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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.
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- A genetically encoded isonitrile lysine for orthogonal bioorthogonal labeling schemes
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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
- Biró, Adrienn,Cserép, Gergely B.,Kele, Péter,Molnár, Tibor á.,Németh, Krisztina,S?veges, Bianka,Szabó, Edit,Szatmári, ágnes,Várady, Gy?rgy
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supporting information
(2021/08/26)
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- High-Yielding Water-Soluble Asymmetric Cyanine Dyes for Labeling Applications
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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.
- Wolf, Natalia,Kersting, Louise,Herok, Christoph,Mihm, Cornelius,Seibel, Juergen
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supporting information
p. 9751 - 9760
(2020/09/03)
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- Rapid and Selective Labeling of Endogenous Transmembrane Proteins in Living Cells with a Difluorophenyl Ester Affinity-Based Probe
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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.
- Chan, Hsin-Ju,Lin, Xin-Hui,Fan, Syuan-Yun,Ru Hwu, Jih,Tan, Kui-Thong
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p. 3416 - 3420
(2020/10/02)
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- IMAGING AGENTS
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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.
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Paragraph 0111; 0118
(2020/04/30)
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- S - Cis Diene Conformation: A New Bathochromic Shift Strategy for Near-Infrared Fluorescence Switchable Dye and the Imaging Applications
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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.
- 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
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p. 5224 - 5234
(2018/04/23)
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- FLUORESCENCE COMPOUNDS AND PREPARATION METHOD THEREOF
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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.
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- NOVEL CYANINE COMPOUND FOR LABELING BIOMOLECULE AND PREPARATION METHOD THEREOF
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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
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Paragraph 0232; 0241-0243
(2017/09/14)
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- Fluorescent dyes
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Chemically reactive carbocyanine dyes that are intramolecularly crosslinked between the 1-position and 3′-position, their bioconjugates and their uses are described. 1,3′-crosslinked carbocyanines are superior to those of conjugates of spectrally similar 1,1′-crosslinked or non-crosslinked dyes. The invention includes derivative compounds having one or more benzo nitrogens.
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Paragraph 0090
(2015/10/05)
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- Cyanine compound for labeling biomolecule and preparation method thereof
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Disclosed are a novel cyanine compound, represented by the following Formula 1, for labeling biomolecules, and a method for preparing the same. wherein R1, R2, R3, R4, B, m and n are defined as above.
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- DYE COMPOSITIONS AND DYE SYNTHESES
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The present invention relates to sulfonated unsymmetrical pentamethine optical dye compositions, especially dyes suitable for biological applications in vitro, and for in vivo imaging. Improved dye compositions and intermediates are provided, which enable the suppression of undesirable newly-identified impurities. Also provided is the use of the improved dye compositions in the preparation of conjugates with biological targeting molecules.
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Paragraph 0127; 0129; 0130
(2013/04/24)
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- DYE COMPOSITIONS, METHODS OF PREPARATION, CONJUGATES THEREOF, AND METHODS OF USE
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Dye compounds of the formula (1) wherein A is a protective agent group that has a characteristic of modifying the singlet-triplet occupancy of the shown cyanine moiety, and M is a reactive crosslinking group or a group that can be converted to a reactive crosslinking group. Methods for synthesizing the dye compounds and applications for their use are also described.
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- DYES FOR LABELLING MOLECULAR LIGANDS
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Cyanine dyes with improved fluorescence intensity and photostability.
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Paragraph 00141; 00142
(2013/04/10)
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- Near-infrared heptamethine cyanine dyes. Synthesis, spectroscopic characterization, thermal properties and photostability
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Near-infrared heptamethine cyanine dyes were synthesized without substitution to the polyene chain but with various substituents on the indoleninium fragments. To develop indotricarbocyanine dyes with improved photochemical characteristics, we studied the
- Shershov, Valeriy E.,Spitsyn, Maksim A.,Kuznetsova, Viktoriya E.,Timofeev, Edward N.,Ivashkina, Olga A.,Abramov, Ivan S.,Nasedkina, Tatyana V.,Zasedatelev, Alexander S.,Chudinov, Alexander V.
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p. 353 - 360
(2013/04/23)
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- Synthesis of quaternary heterocyclic salts
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The microwave synthesis of twenty quaternary ammonium salts is described. The syntheses feature comparable yields to conventional synthetic methods reported in the current literature with reduced reaction times and the absence of solvent or minimal solvent.
- Winstead, Angela J.,Nyambura, Grace,Matthews, Rachael,Toney, Deveine,Oyaghire, Stanley
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p. 14306 - 14319
(2014/01/06)
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- Novel asymmetric Cy5 dyes: Synthesis, photostabilities and high sensitivity in protein fluorescence labeling
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Several novel water-soluble asymmetric pentamethine cyanine dyes were synthesized. The maximum absorption and emission wavelengths of the dyes in different solvents were in the range from 647 to 665 nm and exhibited negative solvatochromism with increasing solvent polarity. The fluorescence quantum yields of the dyes were about 0.1 in water, and were obviously higher than those of hydrophobic cyanine dyes. Dyes with N-benzyl groups and N-sulfo-groups displayed greater photostability than dyes with N-carboxypentyl groups in water. The limit of detection of dye 5a for BSA was 1.2 × 10-8 mol L-1 by high performance liquid chromatography with fluorescent director about 100-fold lower than that by UV detection (1.0 × 10-6 mol L-1). Therefore, Dye 5a could be used to improve photostability and detection sensitivity in protein analysis.
- Wang, Li,Fan, Jiangli,Qiao, Xiaoqiang,Peng, Xiaojun,Dai, Bin,Wang, Bingshuai,Sun, Shiguo,Zhang, Lihua,Zhang, Yukui
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experimental part
p. 168 - 172
(2010/10/20)
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- Asymmetric trimethine 3H-indocyanine dyes: Efficient synthesis and protein labeling
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We present an efficient method to synthesize three new asymmetric trimethine cyanine dyes containing only one carboxylic acid group for bioconjugation. Two of them have better protein labeling performance than other conventional cyanine dyes due to their
- Song, Fengling,Wang, Li,Qiao, Xiaoqiang,Wang, Bingshuai,Sun, Shiguo,Fan, Jiangli,Zhang, Lihua,Peng, Xiaojun
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supporting information; experimental part
p. 4249 - 4251
(2010/11/18)
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- A FUNCTIONALIZED CYANINE HAVING A SILANE LINKER ARM, A METHOD OF PREPARING THEREOF AND USES THEREOF
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There is disclosed a silane-modified cyanine of Formula (I) including the valence tautomers thereof: wherein R1 is a linear, saturated or unsaturated alkyl chain, having 1 to 30 carbon atoms, wherein one or more carbon atoms are optionally substituted by a 4-, 5- or 6-membered aromatic or non aromatic cyclic grouping of carbon atoms; R8 and R9 are independently selected from the group consisting of -OCH3, -OCH2CH3, -OCH2CH2CH3, -OCH(CH3)2,-OCH2CH2OCH3, -Cl, -Br, -I, Formula (II), Formula (III), -N(CH3)2, Formula (IV), Formula (V), methyl, ethyl, propyl, isopropyl; The synthesis method and the use as a fluorescent marker for inorganic solid supports, for example silica nanoparticles, and/or for biomolecules such as peptides, antibodies, DNA, RNA, etc., are also disclosed.
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Page/Page column 28
(2010/05/13)
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- NOVEL COMPOUND, PROBE CONTAINING THE NOVEL COMPOUND, AND FLUORESCENCE-IMAGING CONTRAST AGENT CONTAINING THE NOVEL COMPOUND OR THE PROBE
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A compound represented by Formula (1) below, where n is 2 or 3; a is an integer of 1 to 4 and b is an integer of 3 and 5 to 10, or a is 5 and b is an integer of 1 to 10; R1 to R8 each independently represent a hydrogen atom or a sulf
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Page/Page column 8
(2010/08/08)
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- Synthesis of PEG derivatives bearing aminophenyl and their application for liquid-phase synthesis of water-soluble unsymmetrical cyanine dyes
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The synthesis and NMR characterization of soluble PEG-supported polymers were described, and their subsequent application for liquid-phase synthesis of water-soluble cyanine dyes was also studied. Nucleophilic substitution of tosylation of PEG 16 with 1,3-bis(4-nitrophenoxy)-2-propanol 15 under basic conditions, followed by nitro group reduction, gave PEG-bound aminophenyl 18. Another PEG-bound aminophenyl 28 was prepared by condensation reaction of PEG-bound pentaerythritol 25 and 4-aminobenzoic acid followed by the cleavage of BOC group. Subsequent loading and activation of sulfoindoleninium to PEG derivatives 18 or 28 were achieved via simple strategies. Cyanine dyes were released by the attack of heterocyclic carbon nucleophile and the cleavage of PEG-bound hemicyanine without the chromatographic separation. The efficient, facile, and practical approaches appear to be robust and versatile strategies to deliver not only indocyanine dyes but also benzoindocyanine dyes.
- Jiang, Lin-Ling,Li, Bao-Lin,Lv, Feng-Ting,Dou, Li-Fang,Wang, Liu-Chang
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scheme or table
p. 5257 - 5264
(2009/12/01)
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- Catch and release microwave mediated synthesis of cyanine dyes
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Unsymmetrical functionalised cyanine dyes, covering the whole colour range, were readily synthesised (in 100 mg amounts) by a combination of microwave and solid-phase methodologies.
- Lopalco, Maria,Koini, Eftychia N.,Cho, Jin Ku,Bradley, Mark
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supporting information; experimental part
p. 856 - 859
(2009/05/30)
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- An efficient approach to the synthesis of water-soluble cyanine dyes using poly(ethylene glycol) as a soluble support
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An efficient synthesis approach to unsymmetrical water-soluble cyanine dyes has been established. Loading and activation of sulfoindolenium to poly(ethylene glycol) (PEG) have been achieved via a simple strategy. Cyanine dyes are released by the attack of heterocyclic carbon nucleophile and the cleavage of PEG-bound hemicyanine. The efficient approach delivers cyanine dyes in high purity without the nontrivial chromatographic separation.
- Jiang, Lin-Ling,Dou, Li-Fang,Li, Bao-Lin
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p. 5825 - 5829
(2008/02/09)
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- Use of acylsulfonamido-substituted polymethine dyes as fluorescene dyes and/or markers
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The invention relates to a novel polymethine dyes containing at least one acylsulfonamido group of the formula (I) in which n, Y, A and R have the meaning given in the claims, and at least one compound of the formulae (a) to (n) given in the claims. The polymethine dyes according to the invention are suitable for use as dyes and/or labels, in particular for staining or labeling biomolecules.
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Page/Page column 65
(2008/06/13)
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- PH sensitive cyanine dyes as reactive fluorescent reagents
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The present invention provides pH sensitive cyanine dyes having the structure (I) wherein X and Y are independently selected from >C(C1 - C4alkyl)2, sulfur and oxygen; R1 and R2 are independently selected from H, CH2NH2, SO3-, phosphate, phosphonate, quaternary ammonium, (CH2)qCOOH, NCS, CH2NH-COR7, where R7 is C1 - C20 straight or branched alkyl and (CH2)qCOOH where q is an integer from 0 - 10; R3 is H or -L-P where L is selected from C1 - C20 straight or branched alkyl optionally containing 0, 1 or 2 unsaturated groups selected from alkenyl and alkynyl, and P is selected from a reactive group, H, C1 - C20 straight or branched alkyl, SO3-, NH2, quaternary ammonium, CH2NH-COR8, where R8 is C1 - C20 straight or branched alkyl, -(CH2)mCOOH, NHR9 where R9 is C1 - C20 straight or branched alkyl; n is an integer from 0 - 3; p and r are independently 0, 1, 2, 3 or 4 and where p and/or r is greater than 1, each R1 and each R2 may be different, and m is an integer from 1 - 10; and salts and protonated derivatives thereof and methods of using same as fluorescent reagents.
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- Squarate dyes and their use in fluorescent sequencing method
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Novel squarate dyes are described, and adducts of these dyes with biologically significant chemical species such as nucleosides or nucleotides. The adducts have useful properties for fluorescent nucleic acid sequencing methods.
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- Cyanine dye activating group with improved coupling selectivity
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Activating groups for cyanine dyes used to label chain terminators in nucleotide sequencing, based on N-hydroxyphthalimide, are disclosed. From these activating groups, activated dyes of the present Invention are prepared which react with the derivitized nucleotide chain terminators to give a labeled chain terminator of the present Invention. The activating groups of the present Invention allow the dye-chain terminator reaction to occur at a much higher yield and with much greater selectivity for the mono-substituted product, compared with the prior art.
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