Leu-RhoHM | 1241795-08-3

• 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: Leu-RhoHM
• 英文别名: (2S)-2-amino-N-(6'-aminospiro[1H-2-benzofuran-3,9'-xanthene]-3'-yl)-4-methylpentanamide
• CAS: 1241795-08-3
• 化学式: C₂₆H₂₇N₃O₃
• 分子量: 429.519
• InChiKey: VRSMTHQIUCSSHL-CHQVSRGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  99.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  rhodamine 110 在 硫酸 、 sodium methylate 、 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 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.34h， 生成 Leu-RhoHM
  参考文献：
  名称：

  Rational Design of Highly Sensitive Fluorescence Probes for Protease and Glycosidase Based on Precisely Controlled Spirocyclization

  摘要：

  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.

  DOI：

  10.1021/ja309688m

文献信息

• FLUORESCENT PROBE FOR MEASURING PROTEASE
  申请人：Nagano Tetsuo

  公开号：US20120052518A1

  公开（公告）日：2012-03-01

  A compound represented by the formula (I) or a salt thereof (R 1 represents hydrogen atom, or a substituent; R 2 to R 7 represent hydrogen atom, hydroxyl group, an alkyl group, or a halogen atom; R 8 and R 9 represent hydrogen atom, or an alkyl group; X represents a C 1 -C 3 alkylene group; and R 10 represents an acyl group), which promptly causes a structural change from a non-fluorescent closed ring structure to a strongly fluorescent open ring structure by hydrolysis of an acyl group, and is useful as a fluorescent probe for measuring a protease showing superior suitability for quantification.
• US8461358B2
  申请人：——

  公开号：US8461358B2

  公开（公告）日：2013-06-11