(2,5-Dioxopyrrolidin-1-yl) 3',6'-dibromo-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-carboxylate | 907205-63-4

• 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: (2,5-Dioxopyrrolidin-1-yl) 3',6'-dibromo-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-carboxylate
• CAS: 907205-63-4
• 化学式: C₂₅H₁₃Br₂NO₇
• 分子量: 599.189
• InChiKey: PSNWMXKMUOYXDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  、 (2,5-Dioxopyrrolidin-1-yl) 3',6'-dibromo-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-carboxylate 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以77%的产率得到
  参考文献：
  名称：

  A FRET-Based Approach to Ratiometric Fluorescence Detection of Hydrogen Peroxide

  摘要：

  We report the synthesis, properties, and biological applications of Ratio-Peroxyfluor-1 (RPF1), a new ratiometric fluorescent reporter for hydrogen peroxide. RPF1 is comprised of a two-fluorophore cassette, where the spectral overlap between coumarin donor and fluoran/fluorescein acceptor partners can be controlled by the chemoselective peroxide-mediated deprotection of boronic ester pendants on the acceptor dye. RPF1 features good selectivity for hydrogen peroxide over a variety of reactive oxygen species, including superoxide and nitric oxide, a ca. 8-fold increase in fluorescence intensity ratio (lambda517/lambda464) upon H2O2 reaction, and excitation and emission profiles in the visible region. Experiments with viable yeast mitochondria show that RPF1 can monitor and quantify endogenous production of H2O2, establishing the potential utility of this approach for probing peroxide biology in living systems.

  DOI：

  10.1021/ja063308k
• 作为产物：
  描述：

  间溴苯酚 在 甲烷磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 生成 (2,5-Dioxopyrrolidin-1-yl) 3',6'-dibromo-1-oxospiro[2-benzofuran-3,9'-xanthene]-5-carboxylate
  参考文献：
  名称：

  A FRET-Based Approach to Ratiometric Fluorescence Detection of Hydrogen Peroxide

  摘要：

  We report the synthesis, properties, and biological applications of Ratio-Peroxyfluor-1 (RPF1), a new ratiometric fluorescent reporter for hydrogen peroxide. RPF1 is comprised of a two-fluorophore cassette, where the spectral overlap between coumarin donor and fluoran/fluorescein acceptor partners can be controlled by the chemoselective peroxide-mediated deprotection of boronic ester pendants on the acceptor dye. RPF1 features good selectivity for hydrogen peroxide over a variety of reactive oxygen species, including superoxide and nitric oxide, a ca. 8-fold increase in fluorescence intensity ratio (lambda517/lambda464) upon H2O2 reaction, and excitation and emission profiles in the visible region. Experiments with viable yeast mitochondria show that RPF1 can monitor and quantify endogenous production of H2O2, establishing the potential utility of this approach for probing peroxide biology in living systems.

  DOI：

  10.1021/ja063308k

文献信息

• Fluorogenic probes for reactive oxygen species
  申请人：Chang J. Christopher

  公开号：US20070141658A1

  公开（公告）日：2007-06-21

  The present invention provides a novel class of fluorogenic probes for reactive oxygen species. Exemplary probes of the invention utilize a boronate deprotection mechanism to provide high selectivity and optical dynamic range for detecting H 2 O 2 in aqueous solution over similar reactive oxygen species (ROS) including superoxide, nitric oxide, tert-butyl hydroperoxide, and hydroxyl radical; Peroxyresorufin-1 (PR1), Peroxyfluor-1 (PF1), and Peroxyxanthone-1 (PX1) are first-generation probes that respond to H 2 O 2 by an increase in red, green, and blue fluorescence, respectively. The boronate dyes are cell-permeable and can detect micromolar changes in H 2 O 2 concentrations in living cells, including hippocampal neurons, using confocal and two-photon microscopy. The unique combination of ROS selectivity, membrane permeability, and a range of available excitation/emission colors establishes the potential value of PR1, PF1, PX1, and related probes for interrogating the physiology and pathology of cellular H 2 O 2 .

  本发明提供了一种新型荧光探针类别，用于检测活性氧自由基。本发明的典型探针利用硼酸酯去保护机制，在检测水溶液中的H2O2时具有高选择性和光学动态范围，超过了类似的活性氧自由基（ROS），包括超氧化物、一氧化氮、叔丁基过氧化氢和羟基自由基； Peroxyresorufin-1（PR1）、Peroxyfluor-1（PF1）和Peroxyxanthone-1（PX1）是第一代探针，分别通过红、绿和蓝荧光的增加来响应 。硼酸染料可渗透细胞，并可使用共聚焦和双光子显微镜检测活细胞中微摩尔级别的 浓度，包括海马神经元。ROS选择性、膜渗透性和一系列可用的激发/发射颜色的独特组合，确立了PR1、PF1、PX1和相关探针在研究细胞 的生理和病理方面的潜在价值。
• US7842823B2
  申请人：——

  公开号：US7842823B2

  公开（公告）日：2010-11-30
• [EN] FLUOROGENIC PROBES FOR REACTIVE OXYGEN SPECIES<br/>[FR] SONDES FLUOROGENIQUES POUR ESPECES OXYGENEES RADICALAIRES
  申请人：UNIV CALIFORNIA

  公开号：WO2007050810A2

  公开（公告）日：2007-05-03

  [EN] The present invention provides a novel class of fluorogenic probes for reactive oxygen species. Exemplary probes of the invention utilize a boronate deprotection mechanism to provide high selectivity and optical dynamic range for detecting H₂O₂ in aqueous solution over similar reactive oxygen species (ROS) including superoxide, nitric oxide, tert-butyl hydroperoxide, and hydroxyl radical; Peroxyresorufin-1 (PRl), Peroxyfluor- 1 (PFl), and Peroxyxanthone-1 (PXl) are first-generation probes that respond to H₂O₂ by an increase in red, green, and blue fluorescence, respectively. The boronate dyes are cell- permeable and can detect micromolar changes in H₂O₂ concentrations in living cells, including hippocampal neurons, using confocal and two-photon microscopy. The unique combination of ROS selectivity, membrane permeability, and a range of available excitation/emission colors establishes the potential value of PRl, PFl, PXl, and related probes for interrogating the physiology and pathology of cellular H₂O₂.
  [FR] La présente invention concerne une nouvelle catégorie de sondes fluorogéniques pour espèces oxygénées radicalaires. Des sondes de cette invention données à titre d'exemple utilisent un mécanisme de déprotection de boronate pour obtenir une grande sélectivité et une gamme dynamique optique élevée pour détecter H₂O₂ en solution aqueuse sur des espèces oxygénées radicalaires (ROS) similaires comprenant le superoxyde, l'oxyde nitrique, l'hydroperoxyde de tert-butyle et le radical hydroxyle. La Peroxyrésorufine-1 (PR1), le Peroxyfluor-1 (PF1) et la Peroxyxanthone-1 (PX1) sont des sondes de première génération qui répondent à H₂O₂ par une augmentation de la fluorescence, respectivement, rouge, verte et bleue. Les colorants de boronate sont perméables aux cellules et peuvent détecter des variations micromolaires des teneurs en H₂O₂ dans des cellules vivantes, y compris dans des neurones hippocampiques, par microscopie confocale et à deux photons. La combinaison unique de sélectivité de détection des espèces ROS, de perméabilité des membranes et d'une gamme de couleurs d'excitation/émission disponible établit la valeur potentielle de PR1, PF1, PX1 et de sondes associées pour interroger la physiologie et la pathologie de H₂O₂ cellulaire.