3-methyl-2-(methylthio)-[1,3]benzooxazol-3-ium tosylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methyl-2-(methylthio)-[1,3]benzooxazol-3-ium tosylate
• 英文别名: 3-methyl-2-methylsulfanyl-benzooxazolium; toluene-4-sulfonate；N-methyl-2-methylthiobenzoxazolium tosylate；4-Methylbenzenesulfonate;3-methyl-2-methylsulfanyl-1,3-benzoxazol-3-ium
• 化学式: C₇H₇O₃S*C₉H₁₀NOS
• 分子量: 351.447
• InChiKey: MRPSVYYRHVAZFL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methyl-2-(methylthio)-[1,3]benzooxazol-3-ium tosylate 在 potassium iodide 作用下， 以66%的产率得到3-methyl-2-((3-methylbenzo[d]oxazol-2(3H)-ylidene)methyl)benzo[d]oxazol-3-ium 4-methylbenzenesulfonate
  参考文献：
  名称：

  对对称花青染料作为有前途的选择性抗增殖剂在 Caco-2 结直肠癌细胞中的洞察

  摘要：

  癌症仍然是全球发病率最高的疾病之一。多年来，已经使用了几种细胞毒性方法来克服这种公共卫生威胁，例如化学疗法、放射疗法和光动力疗法 (PDT)。花青染料是一类作为PDT增感剂已被广泛研究的化合物；然而，它们在没有光源的情况下的抗增殖潜力几乎没有被探索过。本文描述了 18 种对称单、三和七次甲基花青染料的合成及其作为潜在抗癌剂的评估。分析了杂环性质、抗衡离子和次甲基链长对抗增殖作用和选择性的影响，并收集了相关的构效关系数据。还评估和讨论了光对最有希望的染料的细胞毒活性的影响。研究中的大多数单甲碱和三甲碱花青染料在初始筛选（10 µM ）。然而，浓度-活力曲线显示 Caco-2 细胞系的效力和选择性更高。苯并恶唑衍生的单次甲基花青染料是最有前途的化合物（IC 浓度-活力曲线显示 Caco-2 细胞系具有更高的效力和选择性。苯并恶唑衍生的单次甲基花青染料是最有前途的化合物（IC 浓度-活力曲线显示

  DOI：

  10.3390/molecules27185779
• 作为产物：
  描述：

  2-甲巯基苯并恶唑 、 对甲苯磺酸甲酯 生成 3-methyl-2-(methylthio)-[1,3]benzooxazol-3-ium tosylate
  参考文献：
  名称：

  对对称花青染料作为有前途的选择性抗增殖剂在 Caco-2 结直肠癌细胞中的洞察

  摘要：

  癌症仍然是全球发病率最高的疾病之一。多年来，已经使用了几种细胞毒性方法来克服这种公共卫生威胁，例如化学疗法、放射疗法和光动力疗法 (PDT)。花青染料是一类作为PDT增感剂已被广泛研究的化合物；然而，它们在没有光源的情况下的抗增殖潜力几乎没有被探索过。本文描述了 18 种对称单、三和七次甲基花青染料的合成及其作为潜在抗癌剂的评估。分析了杂环性质、抗衡离子和次甲基链长对抗增殖作用和选择性的影响，并收集了相关的构效关系数据。还评估和讨论了光对最有希望的染料的细胞毒活性的影响。研究中的大多数单甲碱和三甲碱花青染料在初始筛选（10 µM ）。然而，浓度-活力曲线显示 Caco-2 细胞系的效力和选择性更高。苯并恶唑衍生的单次甲基花青染料是最有前途的化合物（IC 浓度-活力曲线显示 Caco-2 细胞系具有更高的效力和选择性。苯并恶唑衍生的单次甲基花青染料是最有前途的化合物（IC 浓度-活力曲线显示

  DOI：

  10.3390/molecules27185779

文献信息

• Fluorescent assay for bacterial gram reaction
  申请人：Molecular Probes, Inc.

  公开号：US05545535A1

  公开（公告）日：1996-08-13

  The invention relates to a method of analyzing a sample thought to contain bacteria using an aqueous solution comprising one or more fluorescent dyes: a fluorescent dye of formula I, a fluorescent dye of formula II, a fluorescent dye of formula III, and a fluorescent dye of formula IV. Each of the dyes differ each from the other in their affinity for nucleic acids and in their spectral response to different types of bacteria in the sample. The first three dyes are nucleic acid stains and the fourth dye is a fluorescent reagent that binds selectively to cell surface components. The fluorescent dyes of formula I are highly membrane-permeant cyanine dye derivatives and label all bacteria, whether live or dead, whether Gram positive or Gram negative. The dyes of formula II label only live Gram positive bacteria and label all dead bacteria, whether Gram positive or negative. The dyes of formula II bind to nucleic acids preferentially with respect to the dyes of formula I. Fluorescent formula III dyes are membrane impermeant dyes that give a fluorescent signal only in cells with compromised plasma membrane integrity, whether Gram negative or Gram positive, and have a much higher binding affinity for nucleic acids than the fluorescent dyes of either formula I or formula II. Formula IV fluorescent dyes preferentially bind to an exterior component of a bacterium. The dyes are combined with a sample suspected of containing bacteria and illuminated at an appropriate wavelength to differentiate, according to the fluorescence response, live Gram negative, dead Gram negative, live Gram positive and dead Gram positive bacteria in the sample.

  该发明涉及一种分析样品中可能含有细菌的方法，使用含有一个或多个荧光染料的水溶液：公式I的荧光染料，公式II的荧光染料，公式III的荧光染料和公式IV的荧光染料。这些染料中的每一种在其与核酸的亲和力以及在样品中对不同类型细菌的光谱响应方面均不同。前三种染料是核酸染料，第四种染料是一种选择性结合到细胞表面成分的荧光试剂。公式I的荧光染料是高度透膜的靛蓝染料衍生物，可标记所有细菌，无论是活的还是死的，无论是革兰氏阳性还是革兰氏阴性。公式II的染料仅标记活的革兰氏阳性细菌，并标记所有死细菌，无论是革兰氏阳性还是阴性。公式II的染料相对于公式I的染料更倾向于选择性结合到核酸上。荧光公式III的染料是透膜不透性染料，仅在细胞的胞浆膜完整性受损时发出荧光信号，无论是革兰氏阴性还是革兰氏阳性，并且与核酸的结合亲和力远高于公式I或公式II的荧光染料。公式IV的荧光染料更倾向于结合到细菌的外部成分。这些染料与疑似含有细菌的样品结合，并在适当波长下照射，根据荧光反应区分样品中的活的革兰氏阴性、死的革兰氏阴性、活的革兰氏阳性和死的革兰氏阳性细菌。
• METHINE DYES AND USES OF THE SAME
  申请人：Dan-Oh Yasufumi

  公开号：US20090076278A1

  公开（公告）日：2009-03-19

  The present invention provides novel organic compounds, which absorb the light in the ultra violet and the infrared regions, have improved light tolerance and solubility in solvents, and have thermal tolerance suitable for uses to which the organic compounds are applied, and provides uses of the same. The above objects are solved by providing indolenine compounds and methine dyes, which have a bis-indolenine skeleton composed of two indolenine rings linked together at their respective C-3 positions via a divalent linking group, and by providing optical recording media containing the methine dyes.

  本发明提供了新型有机化合物，其吸收紫外线和红外线区域的光线，具有改善的光耐受性和溶解性，并具有适用于有机化合物应用的热耐受性，并提供了它们的用途。上述目标通过提供吲哚啉化合物和甲红染料来实现，其具有由两个吲哚啉环通过二价连接基在它们各自的C-3位置连接在一起形成的双吲哚啉骨架，并通过提供包含该甲红染料的光记录介质来实现。
• SEPARATION AND ISOLATION OF NUCLEIC ACIDS USING AFFINITY LIGANDS BOUND TO A SOLID SURFACE
  申请人：emp Biotech GmbH

  公开号：US20210155657A1

  公开（公告）日：2021-05-27

  A method of isolating and separating a target macromolecule, such DNA (double stranded or single stranded), RNA (double stranded or single stranded), messenger RNA, or other oligonucleotide or oligonucleoside, from a sample by binding the target macromolecule to an affinity ligand that is bound to a surface is disclosed. The method may be employed in chromatography or any other of the separation sciences.

  揭示了一种从样品中通过将目标大分子（如DNA（双链或单链）、RNA（双链或单链）、信使RNA或其他寡核苷酸或寡核苷苷）与固定在表面上的亲和配体结合来分离和分离目标大分子的方法。该方法可应用于色谱或其他分离科学中。
• Key Structural Elements of Unsymmetrical Cyanine Dyes for Highly Sensitive Fluorescence Turn-On DNA Probes
  作者：Kakishi Uno、Taeko Sasaki、Nagisa Sugimoto、Hideto Ito、Taishi Nishihara、Shinya Hagihara、Tetsuya Higashiyama、Narie Sasaki、Yoshikatsu Sato、Kenichiro Itami

  DOI：10.1002/asia.201601430

  日期：2017.1.17

  a series of unsymmetrical cyanine dyes plays a critical role in the fluorescence enhancement. Four newly designed unsymmetrical cyanine dyes showed negligible intrinsic fluorescence in the free state and strong fluorescence upon binding to double‐stranded DNA (dsDNA) with a quantum yield of 0.53 to 0.90, which is 2 to 3 times higher than previous unsymmetrical cyanine dyes. A detailed analysis of the

  非对称花青染料（例如噻唑橙）可用于检测具有荧光的核酸，因为它们在结合核酸后会显着增强荧光。在这里，我们合成了一系列不对称的花青染料，并评估了它们的荧光特性。一项系统的结构-性质关系研究表明，一系列不对称花青染料中喹啉2位的二烷基氨基在荧光增强中起关键作用。四种新设计的不对称花青染料在游离状态下显示可忽略的固有荧光，与双链DNA（dsDNA）结合后显示强荧光，其量子产率为0.53至0.90，这是以前的不对称花青染料的2至3倍。荧光寿命的详细分析表明，喹啉2位的二烷基氨基抑制了非辐射衰变，从而增加了荧光量子产率。此外，这些新开发的染料能够通过共聚焦激光扫描显微镜对固定的HeLa细胞中的细胞核进行特殊染色。
• New cyanine dyes as base surrogates in PNA: Forced intercalation probes (FIT-probes) for homogeneous SNP detection
  作者：Lucas Bethge、Dilip Venkatrao Jarikote、Oliver Seitz

  DOI：10.1016/j.bmc.2006.12.044

  日期：2008.1

  Forced intercalation probes (FIT-probes) are nucleic acid probes, in which an intercalator cyanine dye such as thiazole orange (TO) serves as a replacement of a canonical nucleobase. These probes signal hybridization by showing strong increases of fluorescence. TO in FIT-probes responds to adjacent base mismatches by attenuation of fluorescence intensities at conditions where both matched and mismatched target DNA are bound. The interesting features of TO labeled FIT-probes posed the question whether the forced intercalation concept can be extended to other cyanine dyes of the thiazole orange family. Herein, we present the synthesis of three asymmetrical cyanine dyes and their incorporation into PNA-conjugates by means of both divergent and linear solid-phase synthesis. Melting analysis revealed that the DNA affinity of PNA probes remained high irrespective of the replacement of a nucleobase by the cyanines YO (oxazole yellow), MO or JO. Of the three new tested dye-PNA-conjugates, the YO-containing PNA has properties useful for homogeneous SNP detection. YO-PNA is demonstrated to signal the presence of fully complementary DNA by up to 20-fold enhancement of fluorescence. In addition, YO emission discriminates against single base mismatches by attenuation of fluorescence. Oxazole yellow (YO) as a base surrogate in PNA may prove useful in the multiplex detection of single base mutations at non-stringent conditions. (C) 2007 Elsevier Ltd. All rights reserved.