20064-98-6Relevant articles and documents
Cyanine dye conjugates as probes for live cell imaging
Carreon, Jay R.,Stewart, Kelly M.,Mahon Jr., Kerry P.,Shin, Stephanie,Kelley, Shana O.
, p. 5182 - 5185 (2007)
A series of fluorescent compounds suitable for live cell imaging is described. Functionalized forms of four different asymmetric cyanine dyes are reported that are amenable to peptide conjugation. The photophysical properties of the modified dyes and conj
Thiazole Orange-Peptide Conjugates: Sensitivity of DNA Binding to Chemical Structure
Carreon, Jay R.,Mahon Jr., Kerry P.,Kelley, Shana O.
, p. 517 - 519 (2004)
(Equation presented) Derivatives of the highly fluorescent and DNA-binding dye thiazole orange (TO) are described that feature appended peptides. Functionalization of TO can be achieved at either of the endocyclic nitrogens, and the photophysical properties and DNA-binding modes are sensitive to the position of the tethered peptide. A series of TO-peptide conjugates are described, demonstrating the utility of a solid-phase synthesis approach to their preparation and illustrating how the photophysical and DNA-binding properties of the compounds are influenced by chemical structure.
New cyanine-oligonucleotide conjugates: Relationships between chemical structures and properties
Lartia, Remy,Asseline, Ulysse
, p. 2270 - 2281 (2006)
Because the influence of the chemical structure of monomethine cyanine-oligo-2′-deoxyribonudeotide (ODN) conjugates on their binding and fluorescence properties has remained largely undetermined, we synthesized and studied a wide range of conjugates with various structural patterns. Different cyanine dyes such as thiocyanine, quinocyanine, and thiazole orange isomers were obtained. In the case of unsymmetrical cyanines. the linker was attached to either the quinoline or the benzothiazole nucleus. The influence of the ODN counterpart was evaluated by linking the cyanines to the 5'-end or to an internucleotidic phosphate. In the first case, the influence of neighboring nucleic bases was studied, whereas in the second, the stereochemical configuration at the phosphorus atom bearing the cyanine was investigated. We report here on relationships between the structures of the dyes and conjugates and some of their properties, such as the stability and fluorescence changes observed on their hybridization with the target sequence. This study provides useful information towards the design of ODN-cyanine conjugates.
A small-sized benzothiazole-indolium fluorescent probe: The study of interaction specificity targeting c-MYC promoter G-quadruplex structures and live cell imaging
Zheng, Bo-Xin,She, Meng-Ting,Long, Wei,Xu, Yong-Yu,Zhang, Yi-Han,Huang, Xuan-He,Liu, Wenjie,Hou, Jin-Qiang,Wong, Wing-Leung,Lu, Yu-Jing
, p. 15016 - 15019 (2020)
A small-sized c-MYC promoter G-quadruplex selective fluorescent BZT-Indolium binding ligand was demonstrated for the first time as a highly target-specific and photostable probe for in vitro staining and live cell imaging and it was found to be able to inhibit the amplification of the c-MYC G-rich sequence (G-quadruplex) and down-regulate oncogene c-MYC expression in human cancer cells (HeLa). This journal is
Synthesis, spectral properties of rhodanine complex merocyanine dyes as well as their effect on K562 leukemia cells
Xiang, Jun-Feng,Liu, Yan-Xia,Sun, Dan,Zhang, Su-Juan,Fu, Yi-Le,Zhang, Xiang-Han,Wang, Lan-Ying
, p. 1481 - 1487 (2012)
Two rhodanine complex merocyanine dyes 9a and 9b were synthesized and their structures were confirmed by 1H NMR, IR, MS, HRMS and UV-Vis spectra. From the spectral properties of the two dyes, it could be found that the λmax of the dyes showed hypsochromic shifts with the increase of permittivity in protonic solvents, and bathochromic shifts with the increase of refractive index in non protonic solvents. The interactions of two dyes with DNA or BSA were also studied under physiological conditions. The results showed that the quantum yield of DNA-dye 9a was up to 29.5 times compared with free dye 9a. Dyes 9a and 9b were researched in Photodynamic Therapy (PDT) as well. It was demonstrated that supplementation of dye 9a or 9b as photosensitizers for PDT in K562 cells decreases the survival rate.
Design of thiazole orange oligonucleotide probes for detection of DNA and RNA by fluorescence and duplex melting
Klimkowski, Piotr,De Ornellas, Sara,Singleton, Daniel,El-Sagheer, Afaf H.,Brown, Tom
, p. 5943 - 5950 (2019)
We have synthesised a range of thiazole orange (TO) functionalised oligonucleotides for nucleic acid detection in which TO is attached to the nucleobase or sugar of thymidine. The properties of duplexes between TO-probes and their DNA and RNA targets strongly depend on the length of the linker between TO and the oligonucleotide, the position of attachment of TO to the nucleotide (major or minor groove) and the mode of attachment of thiazole orange (via benzothiazole or quinoline moiety). This information can be used to design probes for detection of target nucleic acids by fluorescence or duplex melting. With cellular imaging in mind we show that 2′-OMe RNA probes with TO at the 5-position of uracil or the 2′-position of the ribose sugar are particularly effective, exhibiting up to 44-fold fluorescence enhancement against DNA and RNA, and high duplex stability. Excellent mismatch discrimination is achieved when the mispaired base is located adjacent to the TO-modified nucleotide rather than opposite to it. The simple design, ease of synthesis and favourable properties of these TO probes suggest applications in fluorescent imaging of DNA and RNA in a cellular context.
Twisted cyanines: A non-planar fluorogenic dye with superior photostability and its use in a protein-based fluoromodule
Shank, Nathaniel I.,Pham, Ha H.,Waggoner, Alan S.,Armitage, Bruce A.
, p. 242 - 251 (2013)
The cyanine dye thiazole orange (TO) is a well-known fluorogenic stain for DNA and RNA, but this property precludes its use as an intracellular fluorescent probe for non-nucleic acid biomolecules. Further, as is the case with many cyanines, the dye suffer
Fluorescence Detection of KRAS2 mRNA Hybridization in Lung Cancer Cells with PNA-Peptides Containing an Internal Thiazole Orange
Sonar, Mahesh V.,Wampole, Matthew E.,Jin, Yuan-Yuan,Chen, Chang-Po,Thakur, Mathew L.,Wickstrom, Eric
, p. 1697 - 1708 (2014)
We previously developed reporter-peptide nucleic acid (PNA)-peptides for sequence-specific radioimaging and fluorescence imaging of particular mRNAs in cells and tumors. However, a direct test for PNA-peptide hybridization with RNA in the cytoplasm would be desirable. Thiazole orange (TO) dye at the 5′ end of a hybridization agent shows a strong increase in fluorescence quantum yield when stacked upon a 5′ terminal base pair, in solution and in cells. We hypothesized that hybridization agents with an internal TO could distinguish a single base mutation in RNA. Thus, we designed KRAS2 PNA-IGF1 tetrapeptide agents with an internal TO adjacent to the middle base of the 12th codon, a frequent site of cancer-initiating mutations. Our molecular dynamics calculations predicted a disordered bulge with weaker hybridization resulting from a single RNA mismatch. We observed that single-stranded PNA-IGF1 tetrapeptide agents with an internal TO showed low fluorescence, but fluorescence escalated 5-6-fold upon hybridization with KRAS2 RNA. Circular dichroism melting curves showed ～10 °C higher Tm for fully complementary vs single base mismatch TO-PNA-peptide agent duplexes with KRAS2 RNA. Fluorescence measurements of treated human lung cancer cells similarly showed elevated cytoplasmic fluorescence intensity with fully complementary vs single base mismatch agents. Sequence-specific elevation of internal TO fluorescence is consistent with our hypothesis of detecting cytoplasmic PNA-peptide:RNA hybridization if a mutant agent encounters the corresponding mutant mRNA. (Figure Presented).
Tunable Amine-Reactive Electrophiles for Selective Profiling of Lysine
Backus, Keriann M.,Boatner, Lisa M.,Cao, Jian,Farhi, Jonathan,Houk, Kendall N.,Li, Linwei,Raj, Monika,Spangle, Jennifer,Tang, Kuei-Chien
, (2021/12/22)
Proteome profiling by activated esters identified >9000 ligandable lysines but they are limited as covalent inhibitors due to poor hydrolytic stability. Here we report our efforts to design and discover a new series of tunable amine-reactive electrophiles (TAREs) for selective and robust labeling of lysine. The major challenges in developing selective probes for lysine are the high nucleophilicity of cysteines and poor hydrolytic stability. Our work circumvents these challenges by a unique design of the TAREs that form stable adducts with lysine and on reaction with cysteine generate another reactive electrophiles for lysine. We highlight that TAREs exhibit substantially high hydrolytic stability as compared to the activated esters and are non-cytotoxic thus have the potential to act as covalent ligands. We applied these alternative TAREs for the intracellular labeling of proteins in different cell lines, and for the selective identification of lysines in the human proteome on a global scale.
Monitoring and Modulating mtDNA G-Quadruplex Dynamics Reveal Its Close Relationship to Cell Glycolysis
Chen, Shuo-Bin,Chen, Xiu-Cai,Dai, Jing,Huang, Zhi-Shu,Luo, Wen-Hua,Shao, Wen,Tan, Jia-Heng,Tang, Gui-Xue,Zeng, Shu-Tang
supporting information, p. 20779 - 20791 (2021/12/14)
The mitochondrial DNA G-quadruplex (mtDNA G4) is a potential regulatory element for the regulation of mitochondrial functions; however, its relevance and specific roles in diseases remain largely unknown. Here, we engineered a set of chemical probes, incl
