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107091-89-4 | Thiazole Orange
CAS No: 107091-89-4 Catalog No: AG007B5U MDL No:
Product Description
Catalog Number:
AG007B5U
Chemical Name:
Thiazole Orange
CAS Number:
107091-89-4
Molecular Formula:
C26H24N2O3S2
Molecular Weight:
476.6104
IUPAC Name:
4-methylbenzenesulfonate;(2Z)-3-methyl-2-[(1-methylquinolin-1-ium-4-yl)methylidene]-1,3-benzothiazole
InChI:
InChI=1S/C19H17N2S.C7H8O3S/c1-20-12-11-14(15-7-3-4-8-16(15)20)13-19-21(2)17-9-5-6-10-18(17)22-19;1-6-2-4-7(5-3-6)11(8,9)10/h3-13H,1-2H3;2-5H,1H3,(H,8,9,10)/q+1;/p-1
InChI Key:
ACOJCCLIDPZYJC-UHFFFAOYSA-M
SMILES:
C[n+]1ccc(c2c1cccc2)/C=c/1\sc2c(n1C)cccc2.Cc1ccc(cc1)S(=O)(=O)[O-]
Properties
Complexity:
628
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1
Exact Mass:
476.123g/mol
Formal Charge:
0
Heavy Atom Count:
33
Hydrogen Bond Acceptor Count:
5
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
476.609g/mol
Monoisotopic Mass:
476.123g/mol
Rotatable Bond Count:
1
Topological Polar Surface Area:
98A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
| Title | Journal |
|---|---|
| Folate conjugated chitosan grafted thiazole orange derivative with high targeting for early breast cancer cells diagnosis. | Journal of fluorescence 20121101 |
| A fluorescent molecular switch for room temperature operation based on oligonucleotide hybridization without labeling of probes or targets. | Analytica chimica acta 20121031 |
| Reversed assembly of dyes in an RNA duplex compared with those in DNA. | Chemistry (Weinheim an der Bergstrasse, Germany) 20121015 |
| Dual fluorophore PNA FIT-probes--extremely responsive and bright hybridization probes for the sensitive detection of DNA and RNA. | Organic & biomolecular chemistry 20120928 |
| Single labeled DNA FIT probes for avoiding false-positive signaling in the detection of DNA/RNA in qPCR or cell media. | Chembiochem : a European journal of chemical biology 20120924 |
| Effect of thiazole orange doubly labeled thymidine on DNA duplex formation. | Biochemistry 20120807 |
| Development of a universal colorimetric indicator for G-quadruplex structures by the fusion of thiazole orange and isaindigotone skeleton. | Analytical chemistry 20120807 |
| Flow cytometer based on triggered supercontinuum laser illumination. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20120701 |
| Study on synthesis and spectrum of novel styryl cyanine dyes with a carbazole bridged chain. | Journal of fluorescence 20120501 |
| Human telomeric G-quadruplex formation and highly selective fluorescence detection of toxic strontium ions. | Molecular bioSystems 20120301 |
| Improvement of RNAi activity and strand selectivity of RISC formation by modified siRNA involving intercalators near 5' termini. | Chembiochem : a European journal of chemical biology 20120123 |
| Recognition-mediated light-up of thiazole orange with cucurbit[8]uril: exchange and release by chemical stimuli. | The journal of physical chemistry. B 20120112 |
| Surfactant-induced aggregation patterns of thiazole orange: a photophysical study. | Langmuir : the ACS journal of surfaces and colloids 20111018 |
| Fluorescent DNA nanotags featuring covalently attached intercalating dyes: synthesis, antibody conjugation, and intracellular imaging. | Bioconjugate chemistry 20110817 |
| Cy5-conjugated hybridization-sensitive fluorescent oligonucleotides for ratiometric analysis of nuclear poly(A)+ RNA. | Bioconjugate chemistry 20110817 |
| Fluorescence intercalator displacement assay for screening G4 ligands towards a variety of G-quadruplex structures. | Biochimie 20110801 |
| Thiazole orange (TO) as a light-switch probe: a combined quantum-mechanical and spectroscopic study. | Physical chemistry chemical physics : PCCP 20110721 |
| Development of a high-throughput G4-FID assay for screening and evaluation of small molecules binding quadruplex nucleic acid structures. | Analytical and bioanalytical chemistry 20110701 |
| Synthesis of chloro-substituted analogs of Thiazole orange - Fluorophores for flow cytometric analyses. | Journal of photochemistry and photobiology. B, Biology 20110602 |
| Real time RNA transcription monitoring by Thiazole Orange (TO)-conjugated Peptide Nucleic Acid (PNA) probes: norovirus detection. | Molecular bioSystems 20110501 |
| Thiazole orange-induced c-di-GMP quadruplex formation facilitates a simple fluorescent detection of this ubiquitous biofilm regulating molecule. | Journal of the American Chemical Society 20110406 |
| Fluorescence imaging of influenza H1N1 mRNA in living infected cells using single-chromophore FIT-PNA. | Angewandte Chemie (International ed. in English) 20110218 |
| Left-handed DNA: intercalation of the cyanine thiazole orange and structural changes. A kinetic and thermodynamic approach. | Physical chemistry chemical physics : PCCP 20101028 |
| Targeted thiazole orange derivative with folate: synthesis, fluorescence and in vivo fluorescence imaging. | Molecules (Basel, Switzerland) 20101011 |
| Towards a fluorescent molecular switch for nucleic acid biosensing. | Analytical and bioanalytical chemistry 20101001 |
| DNA/ligand/ion-based ensemble for fluorescence turn on detection of cysteine and histidine with tunable dynamic range. | Analytical chemistry 20101001 |
| Calix[4]arene sulfonate as a template for forming fluorescent thiazole orange H-aggregates. | Chemical communications (Cambridge, England) 20100528 |
| Designed thiazole orange nucleotides for the synthesis of single labelled oligonucleotides that fluoresce upon matched hybridization. | Organic & biomolecular chemistry 20100521 |
| Specific high-affinity binding of thiazole orange to triplex and G-quadruplex DNA. | Biochemistry 20100504 |
| Imaging of RNA delivery to cells by thiazole orange as a fluorescent RNA base substitution. | Organic & biomolecular chemistry 20100307 |
| Photoinduced short-range electron transfer in DNA with fluorescent DNA bases: lessons from ethidium and thiazole orange as charge donors. | Physical chemistry chemical physics : PCCP 20100107 |
| Optical antisense tumor targeting in vivo with an improved fluorescent DNA duplex probe. | Bioconjugate chemistry 20090601 |
| Conjugated polyelectrolyte amplified thiazole orange emission for label free sequence specific DNA detection with single nucleotide polymorphism selectivity. | Analytical chemistry 20090515 |
| Design and development of enzymatically activatable photosensitizer based on unique characteristics of thiazole orange. | Journal of the American Chemical Society 20090506 |
| Benzo(h)quinoline derivatives as G-quadruplex binding agents. | Bioorganic & medicinal chemistry letters 20090315 |
| Reticulated platelet levels in whole blood and platelet-rich plasma of dogs with various platelet counts measured by flow cytometry. | The Journal of veterinary medical science 20090201 |
| Thiazole Orange derivatives: synthesis, fluorescence properties, and labeling cancer cells. | Bioorganic & medicinal chemistry 20090115 |
| Engineering bisquinolinium/thiazole orange conjugates for fluorescent sensing of G-quadruplex DNA. | Angewandte Chemie (International ed. in English) 20090101 |
| Fluorescent color readout of DNA hybridization with thiazole orange as an artificial DNA base. | Angewandte Chemie (International ed. in English) 20090101 |
| A convenient thiazole orange fluorescence assay for the evaluation of DNA duplex hybridization stability. | Molecular imaging and biology : MIB : the official publication of the Academy of Molecular Imaging 20090101 |
| Screening helix-threading peptides for RNA binding using a thiazole orange displacement assay. | Bioorganic & medicinal chemistry 20081001 |
| Ligands playing musical chairs with G-quadruplex DNA: a rapid and simple displacement assay for identifying selective G-quadruplex binders. | Biochimie 20080801 |
| Sequence dependence of fluorescence emission and quenching of doubly thiazole orange labeled DNA: effective design of a hybridization-sensitive probe. | Bioconjugate chemistry 20080801 |
| Reticulated platelets as a screening test to identify thrombocytopenia aetiology. | QJM : monthly journal of the Association of Physicians 20080701 |
| Inactivation of Leishmania donovani infantum and Trypanosoma cruzi in red cell suspensions with thiazole orange. | Transfusion 20080701 |
| Thiazole orange and Cy3: improvement of fluorescent DNA probes with use of short range electron transfer. | The Journal of organic chemistry 20080606 |
| Monitoring Plasmodium falciparum growth and development by UV flow cytometry using an optimized Hoechst-thiazole orange staining strategy. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20080601 |
| FIT probes: peptide nucleic acid probes with a fluorescent base surrogate enable real-time DNA quantification and single nucleotide polymorphism discovery. | Analytical biochemistry 20080415 |
| Spectroscopic characterization of thiazole orange-3 DNA interaction. | Applied biochemistry and biotechnology 20080401 |
| Study of thiazole orange in aptamer-based dye-displacement assays. | Analytical and bioanalytical chemistry 20080201 |
| Flow cytometric assessment of homeostatic aging of reticulocytes in rats. | Experimental hematology 20080201 |
| FIT-probes in real-time PCR. | Methods in molecular biology (Clifton, N.J.) 20080101 |
| Design of a fluorescent probe for DNA/RNA imaging. | Nucleic acids symposium series (2004) 20080101 |
| Flow cytometry for the rapid detection of bacteria in cell culture production medium. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20071201 |
| Spectral properties and DNA targeting features of a thiazole orange-peptide bioconjugate. | Biomacromolecules 20071101 |
| Dinuclear ruthenium(ii) complexes with flexible bridges as non-duplex DNA binding agents. | Dalton transactions (Cambridge, England : 2003) 20071010 |
| Influence of cyanine dye structure on self-aggregation and interaction with nucleic acids: a kinetic approach to TO and BO binding. | Archives of biochemistry and biophysics 20070901 |
| Influence of preparative procedures on assay of platelet function and apparent effects of antiplatelet agents. | The American journal of cardiology 20070815 |
| Reticulated platelet counts correlate with treatment response in patients with idiopathic thrombocytopenic purpura and help identify the complex causes of thrombocytopenia in patients after allogeneic hematopoietic stem cell transplantation. | Cytometry. Part B, Clinical cytometry 20070701 |
| Effect of UVC-induced damage to DNA on the intercalation of thiazole orange: a convenient reporter for DNA damage. | Photochemistry and photobiology 20070101 |
| Exploring base-pair-specific optical properties of the DNA stain thiazole orange. | Chemistry (Weinheim an der Bergstrasse, Germany) 20070101 |
| Solid-phase synthesis and modification of Thiazole Orange and its derivatives and their spectral properties. | Journal of combinatorial chemistry 20070101 |
| Photochemical properties of novel fluorescent probes for detection of DNA. | Nucleic acids symposium series (2004) 20070101 |
| DNA labelling topologies for monitoring DNA-protein complex formation by fluorescence anisotropy. | Nucleosides, nucleotides & nucleic acids 20070101 |
| Thiazole orange: a useful probe for fluorescence sensing of G-quadruplex-ligand interactions. | Nucleosides, nucleotides & nucleic acids 20070101 |
| A peculiar pattern of expression of the transferrin receptor (CD71) by reticulocytes in patients given recombinant human erythropoietin (rHuEPO): a novel marker for abuse in sport? | Journal of biological regulators and homeostatic agents 20070101 |
| DNA sequence-directed assembly of two peptide bioconjugates. | Bioorganic chemistry 20061001 |
| FRET templated by G-quadruplex DNA: a specific ternary interaction using an original pair of donor/acceptor partners. | Journal of the American Chemical Society 20060913 |
| Detection of terminal mismatches on DNA duplexes with fluorescent oligonucleotides. | Organic & biomolecular chemistry 20060521 |
| Tunable DNA cleavage by intercalating peptidoconjugates. | Chembiochem : a European journal of chemical biology 20060501 |
| Evaluation of platelet turnover by flow cytometry. | Platelets 20060501 |
| Large dynamic Stokes shift of DNA intercalation dye Thiazole Orange has contribution from a high-frequency mode. | Journal of the American Chemical Society 20060308 |
| Thiazole orange, a DNA-binding photosensitizer with flexible structure, can inactivate pathogens in red blood cell suspensions while maintaining red cell storage properties. | Transfusion 20060201 |
| Sequence-specific fluorescence detection of DNA by polyamide-thiazole orange conjugates. | Journal of the American Chemical Society 20051130 |
| Synthesis and fluorescence studies of thiazole orange tethered onto oligonucleotide: development of a self-contained DNA biosensor on a fiber optic surface. | Bioorganic & medicinal chemistry letters 20050315 |
| Forced intercalation probes (FIT Probes): thiazole orange as a fluorescent base in peptide nucleic acids for homogeneous single-nucleotide-polymorphism detection. | Chembiochem : a European journal of chemical biology 20050101 |
| Ensemble hybridisation--a new method for exploring sequence dependent fluorescence of dye-nucleic acid conjugates. | Chemical communications (Cambridge, England) 20041207 |
| Thiazole orange positive platelets in a dog with Evans' syndrome. | The Journal of veterinary medical science 20041001 |
| The polarization of fluorescence of DNA stains depends on the incorporation density of the dye molecules. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20040901 |
| Cooperative strand invasion of supercoiled plasmid DNA by mixed linear PNA and PNA-peptide chimeras. | Biomolecular engineering 20040401 |
| Thiazole orange-peptide conjugates: sensitivity of DNA binding to chemical structure. | Organic letters 20040219 |
| Double staining of Plasmodium falciparum nucleic acids with hydroethidine and thiazole orange for cell cycle stage analysis by flow cytometry. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20040101 |
| Thiazole orange as fluorescent universal base in peptide nucleic acids. | Chemical communications (Cambridge, England) 20031207 |
| Single-molecule fluorescence spectroscopy of TOTO on poly-AT and poly-GC DNA. | Photochemistry and photobiology 20031201 |
| Photosensitized DNA cleavage promoted by amino acids. | Chemical communications (Cambridge, England) 20030807 |
| Development of a fluorescent probe for the study of nucleosome assembly and dynamics. | Analytical biochemistry 20030601 |
| Thiazole orange-positive platelets in cats with thrombocytopenia induced by cyclophosphamide. | The Veterinary record 20030419 |
| Flow cytometric analysis of reticulated platelets in patients with ischemic stroke. | Thrombosis research 20020515 |
| Fluorescent properties of oligonucleotide-conjugated thiazole orange probes. | Photochemistry and photobiology 20020301 |
| Quantitation of reticulated platelets in healthy dogs and in nonthrombocytopenic dogs with clinical disease. | Veterinary clinical pathology 20020101 |
| Generation of reticulated platelets in response to whole blood donation or plateletpheresis. | Transfusion 20011001 |
| Oligonucleotide-conjugated thiazole orange probes as 'light-up' probes for messenger ribonucleic acid molecules in living cells. | Photochemistry and photobiology 20011001 |
| Effects of tetramethylpiperidine (TMP)-substituted phenazines on membrane stability and P-glycoprotein function. | International journal of oncology 20010901 |
| Thiazole orange as the fluorescent intercalator in a high resolution fid assay for determining DNA binding affinity and sequence selectivity of small molecules. | Bioorganic & medicinal chemistry 20010901 |
| Thiazole orange-positive platelets in healthy and thrombocytopenic dogs. | The Veterinary record 20010728 |
| Interactions of cyanine dyes with nucleic acids. XXIV. Aggregation of monomethine cyanine dyes in presence of DNA and its manifestation in absorption and fluorescence spectra. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20010601 |
| Free-probe fluorescence of light-up probes. | Journal of the American Chemical Society 20010207 |
| Synthesis and binding properties of oligo-2'-deoxyribonucleotides covalently linked to a thiazole orange derivative. | Bioconjugate chemistry 20010101 |
| A flow cytometric technique using thiazole orange to detect platelet engraftment following pediatric stem-cell transplants. | Cytotherapy 20010101 |
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