2-bromomethyl-1-azathiaxanthone | 881387-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-bromomethyl-1-azathiaxanthone
• 英文别名: 2-bromomethyl-1-azathioxanthone；2-(bromomethyl)thiochromeno[2,3-b]pyridin-5-one
• CAS: 881387-32-2
• 化学式: C₁₃H₈BrNOS
• 分子量: 306.183
• InChiKey: DAORVOMCXLDJLF-UHFFFAOYSA-N

物化性质

• 沸点：
  462.1±45.0 °C(Predicted)
• 密度：
  1.657±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.96
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-bromomethyl-1-azathiaxanthone 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 76.0h， 生成 4-[(1-azathioxanthone)-2-methyl]-10-[methylsulfonylaminoethyl]-1,7-bis(α-dimethylglutarate)-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  A single component ratiometric pH probe with long wavelength excitation of europium emission

  摘要：

  在 370-405 nm 范围内激发后，含有 N-甲基磺酰胺分子的细胞渗透性大环 Eu（III）络合物的发射光谱会随 pH 值的变化而改变形式，从而可以在 6 到 8 的范围内进行 pH 值比率测量。

  DOI：

  10.1039/b616665b
• 作为产物：
  描述：

  2-氯-6-甲基烟酸 在 N-溴代丁二酰亚胺(NBS) 、 PPA 、 potassium carbonate 、 copper(I) bromide 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 2-bromomethyl-1-azathiaxanthone
  参考文献：
  名称：

  A Europium Complex That Selectively Stains Nucleoli of Cells

  摘要：

  A europium complex selectively staining the nucleolus of NIH 3T3, HeLa, and HDF cells is reported. This complex possesses not only the advantage of the long lifetime of europium emission (0.3 ms), but also a chromophore that allows excitation at a relatively long wavelength (lambda(max) = 384 nm) and gives rise to an acceptable quantum yield (9%). The complex can be used both in live cell and fixed cell imaging, giving an average intracellular concentration on the order of 0.5 mu M. Strong binding to serum albumin has been demonstrated by examination of the analogous gadolinium complex, studying relaxivity changes with increasing protein concentration. The intracellular speciation of the complex has been examined by circularly polarized emission spectroscopy and is consistent with the presence of more than one europium species, possibly protein bound.

  DOI：

  10.1021/ja056303g

文献信息

• A ratiometric optical imaging probe for intracellular pH based on modulation of europium emission
  作者：Robert Pal、David Parker

  DOI：10.1039/b718993a

  日期：——

  A set of three pH-responsive ratiometric Eu(III)complexes has been synthesised incorporating a coordinated azathioxanthone sensitiser and a pH dependent alkylsulfonamide moiety. Emission properties, anion binding affinities, pH response curves and protein binding constants were studied in detail in aqueous media, and solutions containing various concentrations of interfering anions and protein were also examined. The complex, [EuL3] exhibited some interference from protein and endogenous anions, e.g.lactate and hydrogen carbonate, but possessed a protonation constant of 7.2 in human serum solution. A suitable calibration curve was obtained and was used to determine the local pH using a 680/589 nm intensity ratio vs. pH plot. Confocal fluorescence microscopy images revealed fast uptake of the complex and a well distributed localisation within the cell; fast egress also occurred. Ribosomal localisation, with a high concentration within the protein-dense nucleoli was observed, in a similar manner to structurally related complexes bearing the same coordinated sensitising moiety. An IC50 value of 67 (±20) µM was estimated using an MTT assay. Selected emission band ratio versus pH plots allow pH measurement in the range 6 to 8, enabling intracellular pH to be measured by microscopy. A value of 7.4 was estimated for NIH 3T3 cells in the protein rich regions of the nucleolus and ribosomes.

  我们合成了一组三个具有 pH 值响应的比率测量型 Eu（III）络合物，其中包含一个配位的氮氧蒽酮敏化剂和一个与 pH 值相关的烷基磺酰胺分子。在水介质中对发射特性、阴离子结合亲和力、pH 值响应曲线和蛋白质结合常数进行了详细研究，并对含有不同浓度干扰阴离子和蛋白质的溶液进行了检测。复合物[EuL3]受到蛋白质和内源性阴离子（如乳酸盐和碳酸氢盐）的一些干扰，但在人血清溶液中的质子化常数为 7.2。通过 680/589 nm 波长强度比与 pH 值的关系曲线，我们得到了一条合适的校准曲线，用于确定局部 pH 值。共聚焦荧光显微镜图像显示了复合物的快速吸收和在细胞内的良好定位分布；同时还显示了快速排出。观察到核糖体定位，在蛋白质密集的核小体内浓度较高，其方式与含有相同配位敏化分子的结构相关复合物相似。使用 MTT 试验估计 IC50 值为 67 (±20) µM。选择的发射带比率与 pH 值的关系图允许在 6 到 8 的范围内测量 pH 值，从而可以通过显微镜测量细胞内的 pH 值。据估计，NIH 3T3 细胞核和核糖体蛋白质丰富区域的 pH 值为 7.4。
• [EN] LUMINESCENT LANTHANIDE COMPLEXES<br/>[FR] COMPLEXES LUMINESCENTS DE LANTHANIDES
  申请人：UNIV DURHAM

  公开号：WO2010086615A1

  公开（公告）日：2010-08-05

  The invention provides a compound of formula (I): wherein: R1 is an optionally substituted 2-(1-azathiaxanthone); each -R2 is independently of the formula -CH2-C(=O)-R4, wherein R4 is an amino acid or a salt thereof, attached to the remainder of R2 through the nitrogen atom of the amino group; and R3 is hydrogen or a C1-6 alkyl group); or (wherein: R1 is an optionally substituted 2-(1-azaxanthone); each R2 is independently an optionally substituted glutaric or succinic acid, or a salt or ester thereof; and R3 is hydrogen or a C1-6 alkyl group).

  本发明提供了一个化合物，其化学式为（I）：其中：R1是可选取代的2-（1-氮杂黄酮）;每个-R2独立地是公式-CH2-C（=O）-R4，其中R4是氨基酸或其盐，通过氨基团的氮原子连接到R2的其余部分;而R3是氢或C1-6烷基）;或（其中：R1是可选取代的2-（1-氮杂黄色素）;每个R2独立地是可选取代的戊二酸或琥珀酸，或其盐或酯;而R3是氢或C1-6烷基）。