Thiazole Orange - CAS 107091-89-4
Molecular Formula:
C26H24N2O3S2
Molecular Weight:
476.61
COA:
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Application\Fluorophore:
DNA Stains
Description:
Thiazole Orange is a cell-permeant fluorescent DNA stain used for reticulocyte analysis. It also has the potental use for Plasmodium species analysis.
Appearance:
Solid Powder
Synonyms:
1-Methyl-4-[(3-methyl-2(3H)-benzothiazolylidene)methyl]quinolinium p-tosylate
MSDS:
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InChIKey:
ACOJCCLIDPZYJC-UHFFFAOYSA-M
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
Canonical SMILES:
CC1=CC=C(C=C1)S(=O)(=O)[O-].CN1C2=CC=CC=C2SC1=CC3=CC=[N+](C4=CC=CC=C34)C
1.Molecular Engineering of Thiazole Orange Dye: Change of Fluorescent Signaling from Universal to Specific upon Binding with Nucleic Acids in Bioassay.
Lu YJ1, Deng Q1, Hou JQ2, Hu DP1, Wang ZY1, Zhang K1, Luyt LG2,3, Wong WL4, Chow CF4. ACS Chem Biol. 2016 Apr 15;11(4):1019-29. doi: 10.1021/acschembio.5b00987. Epub 2016 Jan 26.
The universal fluorescent staining property of thiazole orange (TO) dye was adapted in order to be specific for G-quadruplex DNA structures, through the introduction of a styrene-like substituent at the ortho-position of the TO scaffold. This extraordinary outcome was determined from experimental studies and further explored through molecular docking studies. The molecular docking studies help understand how such a small substituent leads to remarkable fluorescent signal discrimination between G-quadruplex DNA and other types of nucleic acids. The results reveal that the modified dyes bind to the G-quadruplex or duplex DNA in a similar fashion as TO, but exhibit either enhanced or quenched fluorescent signal, which is determined by the spatial length and orientation of the substituent and has never been known. The new fluorescent dye modified with a p-(dimethylamino)styryl substituent offers 10-fold more selectivity toward telomeric G-quadruplexes than double-stranded DNA substrates.
2.Edesign: Primer and Enhanced Internal Probe Design Tool for Quantitative PCR Experiments and Genotyping Assays.
Kimura Y1,2, Soma T2, Kasahara N3, Delobel D2, Hanami T2, Tanaka Y2, de Hoon MJ2, Hayashizaki Y4, Usui K2,4, Harbers M2. PLoS One. 2016 Feb 10;11(2):e0146950. doi: 10.1371/journal.pone.0146950. eCollection 2016.
Analytical PCR experiments preferably use internal probes for monitoring the amplification reaction and specific detection of the amplicon. Such internal probes have to be designed in close context with the amplification primers, and may require additional considerations for the detection of genetic variations. Here we describe Edesign, a new online and stand-alone tool for designing sets of PCR primers together with an internal probe for conducting quantitative real-time PCR (qPCR) and genotypic experiments. Edesign can be used for selecting standard DNA oligonucleotides like for instance TaqMan probes, but has been further extended with new functions and enhanced design features for Eprobes. Eprobes, with their single thiazole orange-labelled nucleotide, allow for highly sensitive genotypic assays because of their higher DNA binding affinity as compared to standard DNA oligonucleotides. Using new thermodynamic parameters, Edesign considers unique features of Eprobes during primer and probe design for establishing qPCR experiments and genotyping by melting curve analysis.
3.Light-Controlled Cellular Internalization and Cytotoxicity of Nucleic Acid-Binding Agents: Studies in Vitro and in Zebrafish Embryos.
Penas C1, Sánchez MI1, Guerra-Varela J2, Sanchez L2, Vázquez ME3, Mascareñas JL4. Chembiochem. 2016 Jan;17(1):37-41. doi: 10.1002/cbic.201500455. Epub 2015 Nov 27.
We synthesized octa-arginine conjugates of DNA-binding agents (bisbenzamidine, acridine and Thiazole Orange) and demonstrated that their DNA binding and cell internalization can be inhibited by appending a (negatively charged) oligoglutamic tail through a photolabile linker. UV irradiation released the parent conjugates, thus restoring cell internalization and biological activity. Assays with zebrafish embryos demonstrates the potential of this prodrug strategy for controlling in vivo cytotoxicity.
4.Time-Dependent Decay of mRNA and Ribosomal RNA during Platelet Aging and Its Correlation with Translation Activity.
Angénieux C1,2,3,4, Maître B1,2,3,4, Eckly A1,2,3,4, Lanza F1,2,3,4, Gachet C1,2,3,4, de la Salle H1,2,3,4. PLoS One. 2016 Jan 25;11(1):e0148064. doi: 10.1371/journal.pone.0148064. eCollection 2016.
Previous investigations have indicated that RNAs are mostly present in the minor population of the youngest platelets, whereas translation in platelets could be biologically important. To attempt to solve this paradox, we studied changes in the RNA content of reticulated platelets, i.e., young cells brightly stained by thiazole orange (TObright), a fluorescent probe for RNAs. We provoked in mice strong thrombocytopenia followed by dramatic thrombocytosis characterized by a short period with a vast majority of reticulated platelets. During thrombocytosis, the TObright platelet count rapidly reached a maximum, after which TOdim platelets accumulated, suggesting that most of the former were converted into the latter within 12 h. Experiments on platelets, freshly isolated or incubated ex vivo at 37°C, indicated that their "RNA content", here corresponding to the amounts of extracted RNA, and the percentage of TObright platelets were positively correlated.
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Chemical Structure

CAS 107091-89-4 Thiazole Orange

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