9-(2-hydroxymethylphenyl)-3,6-bisaminoxanthylium

• 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: 9-(2-hydroxymethylphenyl)-3,6-bisaminoxanthylium
• 英文别名: hydroxymethylrhodamine green；6-amino-9-(2-(hydroxymethyl)phenyl)-3H-xanthen-3-iminium；[6-Amino-9-[2-(hydroxymethyl)phenyl]xanthen-3-ylidene]azanium；[6-amino-9-[2-(hydroxymethyl)phenyl]xanthen-3-ylidene]azanium
• 化学式: C₂₀H₁₆N₂O₂*H
• 分子量: 317.367
• InChiKey: AUVKCDICXQSWEJ-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  81.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-(2-hydroxymethylphenyl)-3,6-bisaminoxanthylium 在 三乙胺 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.72h， 生成
  参考文献：
  名称：

  Fluorescent probe for high-sensitivity pancreatic fluid detection, and method for detecting pancreatic fluid

  摘要：

  下面是表示为以下公式（I）的化合物或其盐的胰液检测用荧光探针。 （在公式中，A代表氨基酸残基或N-取代氨基酸残基，其中A与公式中相邻的NH形成酰胺键；R1代表氢原子或与苯环结合的1至4个相同或不同的取代基团；R2、R3、R4、R5、R6和R7分别独立地代表氢原子、羟基、烷基或卤素原子；R8和R9分别独立地代表氢原子或烷基；X代表C1-C3烷基基团）。

  公开号：

  US09506102B2
• 作为产物：
  描述：

  Leu-RhoHM 在 leucine aminopeptidase, LAP, porcine kidney, SIGMA L₅₀₀₆-25UN neutral phosphate buffer 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 9-(2-hydroxymethylphenyl)-3,6-bisaminoxanthylium
  参考文献：
  名称：

  FLUORESCENT PROBE FOR USE IN MEASUREMENT OF PROTEASE

  摘要：

  公开号：

  EP2399920B1

文献信息

• Method for diagnosing cancer
  申请人：THE UNIVERSITY OF TOKYO

  公开号：US09610366B2

  公开（公告）日：2017-04-04

  Methods for identifying the presence of cancerous cells or tissue by: applying a compound of formula (I), or salts thereof, to a living body, wherein R1 represents hydrogen or the same or different one to four substituents; R2, R3, R4, R5, R6, and R7 independently represent hydrogen, hydroxy, alkyl, or halogen; R8 and R9 independently represent hydrogen or alkyl; and X represents C1-C3 alkylene; and detecting fluorescence emitted by a compound of formula (II), wherein R1, R2, R3, R4, R5, R6, R7, R8, and R9 are as defined above; wherein fluorescence emitted by a compound of formula (II) is indicative of the presence of cancerous cells or tissue.

  通过以下方法识别癌细胞或组织的存在：将式（I）的化合物或其盐应用于活体，其中R1代表氢或1-4个相同或不同的取代基；R2、R3、R4、R5、R6和R7独立地代表氢、羟基、烷基或卤素；R8和R9独立地代表氢或烷基；X代表C1-C3烷基；并检测由式（II）的化合物发出的荧光，其中R1、R2、R3、R4、R5、R6、R7、R8和R9如上所定义；其中，由式（II）的化合物发出的荧光表明癌细胞或组织的存在。
• Efficacious fluorescence turn-on probe for high-contrast imaging of human cells overexpressing quinone reductase activity
  作者：Quinn A. Best、Bijeta Prasai、Alexandra Rouillere、Amanda E. Johnson、Robin L. McCarley

  DOI：10.1039/c6cc08306d

  日期：——

  A turn-on substrate probe is activated by an oxidoreductase, offering fluorescence images of cancer cells with unprecedented positive signal-to-negative background ratios.

  接通底物探针由氧化还原酶激活，以前所未有的正信号-负背景比提供癌细胞荧光图像。
• Rational Design of Highly Sensitive Fluorescence Probes for Protease and Glycosidase Based on Precisely Controlled Spirocyclization
  作者：Masayo Sakabe、Daisuke Asanuma、Mako Kamiya、Ryu J. Iwatate、Kenjiro Hanaoka、Takuya Terai、Tetsuo Nagano、Yasuteru Urano

  DOI：10.1021/ja309688m

  日期：2013.1.9

  We have synthesized and evaluated a series of hydroxymethyl rhodamine derivatives and found an intriguing difference of intramolecular spirocyclization behavior: the acetylated derivative of hydroxymethyl rhodamine green (Ac-HMRG) exists as a dosed spirocyclic structure in aqueous solution at physiological pH, whereas HMRG itself takes an open nonspirocyclic structure. Ac-HMRG is colorless and nonfluorescent, whereas HMRG is strongly fluorescent. On the basis of these findings, we have developed a general design strategy to obtain highly sensitive fluorescence probes for proteases and glycosidases, by replacing the acetyl group of Ac-HMRG with a substrate moiety of the target enzyme. Specific cleavage of the substrate moiety in the nonfluorescent probe by the target enzyme generates a strong fluorescence signal. To confirm the validity and flexibility of our strategy, we designed and synthesized fluorescence probes for leucine aminopeptidase (Leu-HMRG), fibroblast activation protein (Ac-GlyPro-HMRG), and beta-galactosidase (beta Gal-HMRG). All of these probes were almost nonfluorescent due to the formation of spirocyclic structure, but were converted efficiently to highly fluorescent HMRG by the target enzymes. We confirmed that the probes can be used in living cells. These probes offer great practical advantages, including high sensitivity and rapid response (due to regulation of fluorescence at a single reactive site), as well as resistance to photobleaching, and are expected to be useful for a range of biological and pathological investigations.