2-(11-羟基-3-氧代-3H-二苯并[c,h]氧杂蒽-7-基)苯甲酸 | 51517-45-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 2-(11-羟基-3-氧代-3H-二苯并[c,h]氧杂蒽-7-基)苯甲酸
• 英文名称: naphthofluorescein
• 英文别名: 2-(11-Hydroxy-3-oxo-3H-dibenzo[C,H]xanthen-7-YL)benzoic acid；2-(7-hydroxy-19-oxo-2-oxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(22),3(12),4(9),5,7,10,13,15,17,20-decaen-13-yl)benzoic acid
• CAS: 51517-45-4
• 化学式: C₂₈H₁₆O₅
• mdl: MFCD00701101
• 分子量: 432.432
• InChiKey: LFZLBQHTPRXHSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099
• 危险性防范说明：
  P501,P270,P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P312+P330
• 危险性描述：
  H302,H315,H319

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-(11-羟基-3-氧代-3H-二苯并[c,h]氧杂蒽-7-基)苯甲酸 在 硫酸 作用下， 反应 24.0h， 以50%的产率得到naphthofluorescein methyl ester
  参考文献：
  名称：

  Field Effects Induce Bathochromic Shifts in Xanthene Dyes

  摘要：

  There is ongoing interest in near-infrared (NIR) absorbing and emitting dyes for a variety of biomedical and materials applications. Simple and efficient synthetic procedures enable the judicious tuning of through-space polar (field) effects as well as low barrier hydrogen bonding to modulate the HOMO-LUMO gap in xanthene dyes. This affords unique NIR-absorbing xanthene chromophores.

  DOI：

  10.1021/ja302445w
• 作为产物：
  描述：

  1,6-二羟基萘 在 吡啶 、 甲烷磺酸 、 双氧水 作用下， 以 various solvent(s) 为溶剂， 反应 12.0h， 生成 2-(11-羟基-3-氧代-3H-二苯并[c,h]氧杂蒽-7-基)苯甲酸
  参考文献：
  名称：

  Strong red fluorescent probes suitable for detecting hydrogen peroxide generated by mice peritoneal macrophages

  摘要：

  本文报道了二磺酸萘荧光素 (NFDS-1) 作为红色荧光成像探针检测细胞内 H2O2 的合成、荧光性质和生物应用。

  DOI：

  10.1039/b512440a

文献信息

• Fluorogenic/Fluorescent Probes Derivative from Sulfoxanthene, and Use Thereof
  申请人：bioMérieux

  公开号：US20160146814A1

  公开（公告）日：2016-05-26

  The invention relates to fluorescent/fluorogenic probes of formula (I″) or (II″): wherein Z is chosen between: —NH 2 and —OH, or in the fluorescence quencher group consisting of: —NO 2 ; —N═N—R 1 ; R 1 being any organic group that does not obscure the corresponding azo bond; —NHCO-Pept.; Pept. being a peptide residue or any organic group that does not obscure the corresponding amide bond; —O-Glyc.; Glyc. being a oligoglycoside residue that does not obscure the corresponding glycosidic bond; —O—C(O)—R 2 ; —O—P(O)(OR 2 )(OR 2 ′) and —O—S(O) 2 —R 2 ; R 2 and R 2 ′ being independently a hydrogen atom or an organic group that does not obscure the corresponding ester bond; and R a , R b , R c , R d and R e being independently a hydrogen atom or any organic group that does not obscure the corresponding arylether bond so as not to prevent its possible cleavage by a myeloperoxidase activity. It also relates to the use of these fluorescent/fluorogenic probes, for the detection of an enzyme activity, notably in order to identify/discriminate microorganisms in function of their ability to express particular enzyme activities.

  该发明涉及式(I″)或(II″)的荧光/荧光探针： 其中Z在以下选项中选择：—NH2和—OH，或者在荧光猝灭剂基团中选择：—NO2；—N═N—R1；其中R1是任何不遮挡相应偶氮键的有机基团；—NHCO-Pept.；Pept.是肽残基或任何不遮挡相应酰胺键的有机基团；—O-Glyc.；Glyc.是不遮挡相应糖苷键的寡糖苷残基；—O—C(O)—R2；—O—P(O)(OR2)(OR2′)和—O—S(O)2—R2；其中R2和R2′独立地是氢原子或不遮挡相应酯键的有机基团；以及Ra、Rb、Rc、Rd和Re独立地是氢原子或任何不遮挡相应芳基醚键的有机基团，以便不阻止其可能被髓过氧化酶活性水解。 该发明还涉及这些荧光/荧光探针的用途，用于检测酶活性，特别是为了根据微生物表达特定酶活性的能力来识别/区分微生物。
• NBD-based colorimetric and fluorescent turn-on probes for hydrogen sulfide
  作者：Chao Wei、Qing Zhu、Weiwei Liu、Wenbin Chen、Zhen Xi、Long Yi

  DOI：10.1039/c3ob41870g

  日期：——

  Hydrogen sulfide (H2S) is an important endogenous signalling molecule and also an important environmental target for detection. New reaction-based colorimetric and fluorescent turn-on probes based on selective thiolyling of NBD (7-nitro-1,2,3-benzoxadiazole) ether were explored for sensing of H2S in aqueous buffer. The syntheses of both probes are simple and quite straightforward. The probes are highly

  硫化氢（H 2 S）是重要的内源性信号分子，也是检测的重要环境目标。新的基于反应的比色和荧光接通基于进行了探索为H的感测醚NBD（7-硝基-1,2,3-苯并恶二唑）的选择性thiolyling探针2在含水缓冲液S上。两种探针的合成都很简单，也很简单。该探针对H 2 S的敏感性高，对其他生物相关物种具有选择性。探针1可用于通过肉眼直接可视化H 2 S，并且在与H 2 S反应后显示出1000倍以上的荧光增强。探针2是在生理pH下用于H 2 S的近红外荧光传感器。
• A red-emitting naphthofluorescein-based fluorescent probe for selective detection of hydrogen peroxide in living cells
  作者：Aaron E. Albers、Bryan C. Dickinson、Evan W. Miller、Christopher J. Chang

  DOI：10.1016/j.bmcl.2008.08.035

  日期：2008.11

  We report the synthesis, properties, and cellular application of Naphtho-Peroxyfluor-1 (NPF1), a new fluorescent indicator for hydrogen peroxide based on a red-emitting naphthofluorescein platform. Owing to its boronate cages, NPF1 features high selectivity for hydrogen peroxide over a panel of biologically relevant reactive oxygen species (ROS), including superoxide and nitric oxide, as well as excitation

  我们报告了 Naphtho-Peroxyfluor-1 (NPF1) 的合成、性质和细胞应用，这是一种基于发红光的萘并荧光素平台的过氧化氢新荧光指示剂。由于其硼酸盐笼，NPF1 对一组与生物相关的活性氧 (ROS) 具有高选择性，包​​括超氧化物和一氧化氮，以及可见光谱远红色区域的激发和发射曲线。 >600 纳米）。RAW264.7 巨噬细胞中的流式细胞术实验表明，NPF1 可以报告活细胞中过氧化物水平的变化。
• A near-infrared naphthofluorescein-based fluorescent probe for hydrogen sulfide detection
  作者：Weixing Chen、Pu Xie、Xixi Shan、Huaqi Zhao、Yao Wu、Hongwei Zhou、Xilang Jin

  DOI：10.1016/j.molstruc.2020.127822

  日期：2020.5

  Abstract A simple naphthofluorescein-based probe was designed and synthesized by a two-step method. As expected, there was a good linear relationship between fluorescence intensity (680 nm)/absorbance (640 nm) and H2S concentration in the range of 2.00–10.0 μM with a detection limit of 0.50 μM/0.10 μM (S/N = 3). This probe was applied to monitor H2S concentration in red wine samples. Furthermore, it

  摘要 通过两步法设计并合成了一种简单的萘基荧光素探针。正如预期的那样，荧光强度 (680 nm)/吸光度 (640 nm) 与 H2S 浓度之间存在良好的线性关系，范围为 2.00–10.0 μM，检测限为 0.50 μM/0.10 μM (S/N = 3) . 该探针用于监测红葡萄酒样品中的 H2S 浓度。此外，它已成功用于对活 Hela 细胞中的外源 H2S 进行成像，表明其在生物学和医学中的潜在应用。
• PSMA-TARGETING COMPOUNDS AND USES THEREOF
  申请人：Pomper Martin

  公开号：US20120009121A1

  公开（公告）日：2012-01-12

  Prostate-specific membrane antigen (PSMA) targeting compounds are described. Uses of the compounds for imaging, therapy, cell sorting, and tumor mapping are also described.

  介绍了针对前列腺特异性膜抗原（PSMA）的靶向化合物。还介绍了该化合物用于成像、治疗、细胞分选和肿瘤映射的用途。