55514-14-2

Usage

Uses

Used in Photographic Industry:
3-methyl-2-(methylthio)benzothiazolium p-toluenesulphonate is used as a sensitizing agent in the silver halide photographic process for its ability to enhance the sensitivity of photographic film and paper. This property makes it an important component in the production of high-quality photographic materials, contributing to the development of images with greater clarity and detail.
Used in Medical Imaging and Diagnostic Applications:
MMBTh has also been studied for its potential use in medical imaging and diagnostic applications. Its role as a sensitizer could potentially improve the contrast and resolution in imaging techniques, aiding in the accurate diagnosis and monitoring of various medical conditions. However, further research and development are required to fully explore and establish its applications in this field.

InChI:InChI=1/C9H10NS2.C7H8O3S/c1-10-7-5-3-4-6-8(7)12-9(10)11-2;1-6-2-4-7(5-3-6)11(8,9)10/h3-6H,1-2H3;2-5H,1H3,(H,8,9,10)/q+1;

Upstream product

• 615-22-5 2-methylmercaptobenzothiazole 
• 80-48-8 methyl p-toluene sulfonate 
• 149-30-4 2-Mercaptobenzothiazole 
• 95-51-2 o-chloroaniline 
• 3621-99-6 2-methylthio-6-nitrobenzothiazole 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 2254-94-6 3-methylbenzothiazole-2-thione 

Downstream Products

• 94330-89-9 5-(3-methyl-3H-benzothiazol-2-ylidene)-2-thioxo-3-o-tolyl-thiazolidin-4-one 
• 41504-16-9 5-<3-Methyl-benzthiazolinyliden-(2)>-3-phenyl-rhodanin 
• 79610-23-4 5-(3-methyl-2(3H)-benzothiazolylidene)-2-thioxo-3-benzyl-4-thiazolidinone 
• 1150690-87-1 C₂₆H₂₀ClN₂O₂S⁽¹⁺⁾*Cl^(1-) 
• 1269664-58-5 C₃₈H₃₇N₂O₂S⁽¹⁺⁾*C₇H₇O₃S^(1-) 
• 1269664-56-3 C₃₈H₃₇N₂O₂S⁽¹⁺⁾*C₇H₇O₃S^(1-) 
• 1427472-76-1 YM-08 
• 19695-69-3 3,7-dimethyl-2-(3-methyl-3H-benzothiazol-2-ylidenemethyl)-benzo[1,2-d;4,3-d']bisthiazolium; toluene-4-sulfonate 
• 94330-90-2 5-(3-methyl-3H-benzothiazol-2-ylidene)-2-thioxo-3-p-tolyl-thiazolidin-4-one 
• 93261-80-4 3-(4-chloro-phenyl)-5-(3-methyl-3H-benzothiazol-2-ylidene)-2-thioxo-thiazolidin-4-one 

Relevant academic research and scientific papers

Facile functionalization of peptide nucleic acids (PNAs) for antisense and single nucleotide polymorphism detection

In this report, we show how a convenient on-resin copper-click functionalization of azido-functionalized peptide nucleic acids (PNAs) allows various PNA-based detection strategies. Firstly, a thiazole orange (TO) clicked PNA probe facilitates a binary readout when combined with F/Q labeled DNA, giving increased sensitivity for antisense detection. Secondly, our TO-PNA conjugate also allows single nucleotide polymorphism detection. Since antisense detection is also possible in the absence of the TO label, our sensing platform based on azido-d-ornithine containing PNA even allows for additional and more advanced functionalization and sensing strategies.

Inhibitors of heat shock protein 70 (Hsp70) with enhanced metabolic stability reduce tau levels

The molecular chaperone, Heat Shock Protein 70 (Hsp70), is an emerging drug target for neurodegenerative diseases, because of its ability to promote degradation of microtubule-associated protein tau (MAPT/tau). Recently, we reported YM-08 as a brain penetrant, allosteric Hsp70 inhibitor, which reduces tau levels. However, the benzothiazole moiety of YM-08 is vulnerable to metabolism by CYP3A4, limiting its further application as a chemical probe. In this manuscript, we designed and synthesized seventeen YM-08 derivatives by systematically introducing halogen atoms to the benzothiazole ring and shifting the position of the heteroatom in a distal pyridine. In microsome assays, we found that compound JG-23 has 12-fold better metabolic stability and it retained the ability to reduce tau levels in two cell-based models. These chemical probes of Hsp70 are expected to be useful tools for studying tau homeostasis.

Protein Spherical Nucleic Acids for Live-Cell Chemical Analysis

We report the development of a new strategy for the chemical analysis of live cells based on protein spherical nucleic acids (ProSNAs). The ProSNA architecture enables analyte detection via the highly programmable nucleic acid shell or a functional protein core. As a proof-of-concept, we use an i-motif as the nucleic acid recognition element to probe pH in living cells. By interfacing the i-motif with a forced-intercalation readout, we introduce a quencher-free approach that is resistant to false-positive signals, overcoming limitations associated with conventional fluorophore/quencher-based gold NanoFlares. Using glucose oxidase as a functional protein core, we show activity-based, amplified sensing of glucose. This enzymatic system affords greater than 100-fold fluorescence turn on in buffer, is selective for glucose in the presence of close analogs (i.e., glucose-6-phosphate), and can detect glucose above a threshold concentration of ～5 μM, which enables the study of relative changes in intracellular glucose concentrations.

Neutral analogs of the heat shock protein 70 (Hsp70) inhibitor, JG-98

The heat shock protein 70 (Hsp70) family of molecular chaperones are highly expressed in tumors. Inhibitors containing a pyridinium-modified benzothiazole, such as JG-98, bind to a conserved, allosteric site in Hsp70, showing promising anti-proliferative activity in cancer cells. When bound to Hsp70, the charged pyridinium makes favorable contacts; however, this moiety also increases the inhibitor's fluorescence, giving rise to undesirable interference in biochemical and cell-based assays. Here, we explore whether the pyridinium can be replaced with a neutral pyridine. We report that pyridine-modified benzothiazoles, such as compound 17h (JG2-38), have reduced fluorescence, yet retain promising anti-proliferative activity (EC50 values ~0.1 to 0.07 μM) in breast and prostate cancer cell lines. These chemical probes are expected to be useful in exploring the roles of Hsp70s in tumorigenesis and cell survival.

Nucleic acid dye, and preparation method and application thereof

The invention discloses a nucleic acid dye, and a preparation method and an application thereof. The nucleic acid dye is used for common gel imaging dyeing of nucleic acid electrophoresis, and concretely is a novel nucleic acid dye which can be simultaneously suitable for agarose gel electrophoresis and polyacrylamide gel electrophoresis, and particularly can be used for blue light imaging. The invention also relates to the preparation and the application of dye. The developed novel nucleic acid dye is good in dyeing effect, high in safety, very low in nucleic acid migration influence rate andwide in applicability and can realize blue light imaging. The defect that an existing nucleic acid dye cannot be applied to polyacrylamide gel electrophoresis due to a poor dyeing effect is effectively overcome, and particularly the problem that tailing is likely to be generated when the existing dye is used for hair dyeing and electrophoresis is solved.

Thiazole orange – Spermine conjugate: A potent human telomerase inhibitor comparable to BRACO-19

In this report, we synthesized a series of TO conjugates containing different amino side chains and investigated their binding to telomeric G-quadruplex DNA (G4) using several biophysical methods including fluorometric titration and thermal denaturation monitored by fluorescence and circular dichroism. The composition of side chains strongly affects the binding of these molecules to G-quadruplex DNA. Incorporation of amino side chains increases the binding affinity of TO toward G4 but has a minimal effect on its selectivity for G4 over duplex DNA. The plausible binding modes are a synergistic effect of end-stacking and groove interactions as indicated by docking studies. Inhibition of human telomerase activity by TO derivatives was determined in vitro by the TRAP assay. Several derivatives can selectively inhibit the activity of telomerase over DNA polymerase at low concentrations. More significantly, TO-spermine conjugate (16) exhibits a remarkable effect on telomerase inhibition in the submicromolar range, which is comparable to the inhibition effect of a well-known G4 ligand, BRACO-19. Our results here provide guidance of utilizing TO derivatives as a viable scaffold to design novel G4 ligands, G4 probes, and potent telomerase inhibitors.

POLYMETHINE COMPOUND

The present invention relates to a polymethine compound which can be useful in a hard coating composition or an adhesive composition. The polymethine compound is represented by chemical formula 1. In chemical formula 1, X and Y are each independently O, S or NR11, and R11 is a C1 to C12 aliphatic hydrocarbon group.COPYRIGHT KIPO 2019

Novel 3-methyl-2-alkylthio benzothiazolyl-based ionic liquids: Synthesis, characterization, and antibiotic activity

Three series of novel 3-methyl-2-alkylthio benzothiazolyl ionic liquids (ILs) were synthesized for the first time. After structural identification, their melting point, solubility, and thermostability together with antibiotic activity were determined successively. As a result, 3-methyl-2-alkylthio benzothiazolyl p-toluene sulfonate was found to have the highest antibacterial activity among the three series of ILs. Meanwhile, it has a good solubility in water as well. On the basis of comprehensive comparison with similar compounds, the effect of cations and anions of these benzothiazolium ILs on typical physical properties together with antibiotic performance was explored and discussed, which is very beneficial to take the greatest advantage of their structural designability for various purposes. Furthermore, the experiment data preliminarily discovered the relationships of the structure-properties/activities of the above three kinds ILs to a certain extent, which can provide useful references for future research and for the potential application of these new ILs as surfactant antiseptics or agricultural chemicals.

Differential array sensing for cancer cell classification and novelty detection

A series of semi-specific peptides reported in the literature to bind various epitopes on cell surfaces were used in a differential sensing array to pattern cell line identity. The peptides were conjugated to thiazole orange to act as both a fluorescence reporter and a DNA intercalator. Fluorescence data for the peptides exposed to cells, with and without exogenous double stranded DNA (dsDNA), led to chemometric fingerprints for eight cancer cell lines. In contrast to the use of structures meant to act in completely non-specific ways, the use of a limited level of specificity generated linear discriminant score plots with high dimensionality, i.e. several principle components carrying significant variance. The arrays were found to correctly classify the cell lines from 60% to 100% depending upon the cell line. Due to the high dimensionality score plots, the identification of cell lines that were not part of the training set was examined. Support vector machines were used as a novelty detection routine and showed that a cancer line not part of the original training set could be correctly identified as being novel.

FLUORESCENT MOLECULAR ROTORS

The present invention relates to methods and compositions for detecting an interaction between a protein and a ligand, comprising: (i) binding at least one fluorescent molecular rotor to said ligand or protein; and (ii) detecting a change in fluorescence emitted by said fluorescent molecular rotor after contact of the bound fluorescent molecular rotor with the other of said ligand or protein, thereby detecting an interaction between the ligand and the protein, wherein the fluorescent molecular rotor comprises: a rotating ?-bond; an electron-donating moiety; an electron-accepting moiety; and a ?-conjugated linker.