9-[2-(3-carboxy-9,10-dimethyl)anthryl]-6-hydroxy-3H-xanthen-3-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-[2-(3-carboxy-9,10-dimethyl)anthryl]-6-hydroxy-3H-xanthen-3-one
• 英文别名: 3-(3-Hydroxy-6-oxoxanthen-9-yl)-9,10-dimethylanthracene-2-carboxylic acid
• 化学式: C₃₀H₂₀O₅
• 分子量: 460.486
• InChiKey: AMIWJFRDTIEUQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-[2-(3-carboxy-9,10-dimethyl)anthryl]-6-hydroxy-3H-xanthen-3-one 在 C₆₃H₉₉N₁₀O₄S⁽³⁺⁾*3Br^(1-)*ClH 作用下， 以 水 为溶剂， 生成 5-(3-Hydroxy-6-oxoxanthen-9-yl)-1,8-dimethyl-15,16-dioxatetracyclo[6.6.2.02,7.09,14]hexadeca-2(7),3,5,9,11,13-hexaene-4-carboxylic acid
  参考文献：
  名称：

  反应性差异使 ROS 能够选择性消融细菌

  摘要：

  开发了两种化合物以证明 ROS 的反应性差异可能诱导革兰氏阳性细菌的选择性消融。一种主要产生O 2 .−，对革兰氏阳性菌有极好的选择性，而另一种产生较多的1 O 2，​​对细菌没有选择性。这种差异可能为设计用于选择性消融革兰氏阳性细菌的光动力剂铺平了新的道路。

  DOI：

  10.1002/anie.202200808
• 作为产物：
  描述：

  2,3-dibromo-9,10-dimethylanthracene 在 吡啶 、 氢氧化钾 、 甲烷磺酸 、 乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 43.42h， 生成 9-[2-(3-carboxy-9,10-dimethyl)anthryl]-6-hydroxy-3H-xanthen-3-one
  参考文献：
  名称：

  Rational Design of Fluorescein-Based Fluorescence Probes. Mechanism-Based Design of a Maximum Fluorescence Probe for Singlet Oxygen

  摘要：

  Fluorescein is one of the best available fluorophores for biological applications, but the factors that control its fluorescence properties are not fully established. Thus, we initiated a study aimed at providing a strategy for rational design of functional fluorescence probes bearing fluorescein structure. We have synthesized various kinds of fluorescein derivatives and examined the relationship between their fluorescence properties and the highest occupied molecular orbital (HOMO) levels of their benzoic acid moieties obtained by semiempirical PM3 calculations. It was concluded that the fluorescence properties of fluorescein derivatives are controlled by a photoinduced electron transfer (PET) process from the benzoic acid moiety to the xanthene ring and that the threshold of fluorescence OFF/ON switching lies around -8.9 eV for the HOMO level of the benzoic acid moiety. This information provides the basis for a practical strategy for rational design of functional fluorescence probes to detect certain biomolecules. We used this approach to design and synthesize 9-[2-(3-carboxy-9,10- dimethyl)anthryl]-6-hydroxy-3H-xanthen-3-one (DMAX) as a singlet oxygen probe and confirmed that it is the most sensitive probe currently known for O-1(2). This novel fluorescence probe has a 9,10-dimethylanthracene moiety as an extremely fast chemical trap of O-1(2). AS was expected from PM3 calculations, DMAX scarcely fluoresces; while DMAX endoperoxide (DMAX-EP) is strongly fluorescent. Further, DMAX reacts with O-1(2) more rapidly, and its sensitivity is 53-fold higher than that of 9-[2-(3-carboxy-9,10-diphenyl)-anthryl]-6-hydroxy-3H-xanthen-3-ones (DPAX), which are a series of fluorescence probes for singlet oxygen that we recently developed. DMAX should be useful as a fluorescence probe for detecting O-1(2) in a variety of biological systems.

  DOI：

  10.1021/ja0035708

文献信息

• REAGENT FOR DETERMINING SINGLET OXYGEN
  申请人：DAIICHI PURE CHEMICALS CO., LTD.

  公开号：EP1314730B1

  公开（公告）日：2007-01-10
• Rational Design of Fluorescein-Based Fluorescence Probes. Mechanism-Based Design of a Maximum Fluorescence Probe for Singlet Oxygen
  作者：Kumi Tanaka、Tetsuo Miura、Naoki Umezawa、Yasuteru Urano、Kazuya Kikuchi、Tsunehiko Higuchi、Tetsuo Nagano

  DOI：10.1021/ja0035708

  日期：2001.3.1

  Fluorescein is one of the best available fluorophores for biological applications, but the factors that control its fluorescence properties are not fully established. Thus, we initiated a study aimed at providing a strategy for rational design of functional fluorescence probes bearing fluorescein structure. We have synthesized various kinds of fluorescein derivatives and examined the relationship between their fluorescence properties and the highest occupied molecular orbital (HOMO) levels of their benzoic acid moieties obtained by semiempirical PM3 calculations. It was concluded that the fluorescence properties of fluorescein derivatives are controlled by a photoinduced electron transfer (PET) process from the benzoic acid moiety to the xanthene ring and that the threshold of fluorescence OFF/ON switching lies around -8.9 eV for the HOMO level of the benzoic acid moiety. This information provides the basis for a practical strategy for rational design of functional fluorescence probes to detect certain biomolecules. We used this approach to design and synthesize 9-[2-(3-carboxy-9,10- dimethyl)anthryl]-6-hydroxy-3H-xanthen-3-one (DMAX) as a singlet oxygen probe and confirmed that it is the most sensitive probe currently known for O-1(2). This novel fluorescence probe has a 9,10-dimethylanthracene moiety as an extremely fast chemical trap of O-1(2). AS was expected from PM3 calculations, DMAX scarcely fluoresces; while DMAX endoperoxide (DMAX-EP) is strongly fluorescent. Further, DMAX reacts with O-1(2) more rapidly, and its sensitivity is 53-fold higher than that of 9-[2-(3-carboxy-9,10-diphenyl)-anthryl]-6-hydroxy-3H-xanthen-3-ones (DPAX), which are a series of fluorescence probes for singlet oxygen that we recently developed. DMAX should be useful as a fluorescence probe for detecting O-1(2) in a variety of biological systems.
• Reactivity Differences Enable ROS for Selective Ablation of Bacteria
  作者：Xiaofeng Wu、Mengyao Yang、Ji Seon Kim、Rui Wang、Gyoungmi Kim、Jeongsun Ha、Heejeong Kim、Yejin Cho、Ki Taek Nam、Juyoung Yoon

  DOI：10.1002/anie.202200808

  日期：2022.4.19

  demonstrate that the reactive difference of ROS may induce selective ablation of Gram-positive bacteria. One mainly produces O2.− which has an excellent selectivity to Gram-positive bacteria, while the other has a higher generation of 1O2 which shows no selectivity toward bacteria. This difference may pave a new way to engineer photodynamic agents for selectively ablating Gram-positive bacteria.

  开发了两种化合物以证明 ROS 的反应性差异可能诱导革兰氏阳性细菌的选择性消融。一种主要产生O 2 .−，对革兰氏阳性菌有极好的选择性，而另一种产生较多的1 O 2，​​对细菌没有选择性。这种差异可能为设计用于选择性消融革兰氏阳性细菌的光动力剂铺平了新的道路。