N-(5-fluoresceinyl)-5-carbamoylpentanoic acid | 227078-97-9

• 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: N-(5-fluoresceinyl)-5-carbamoylpentanoic acid
• 英文别名: 6-[(3',6'-Dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl)amino]-6-oxohexanoic acid；6-[(3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl)amino]-6-oxohexanoic acid
• CAS: 227078-97-9
• 化学式: C₂₆H₂₁NO₈
• 分子量: 475.455
• InChiKey: VCUFKSIDOISUDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(5-fluoresceinyl)-5-carbamoylpentanoic acid 在 sodium hydroxide 、 三乙醇胺 、 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 6.0h， 生成 N^α-[(5-fluoresceinyl)-5-carbamoylpentanoyl]-N^ε-t-butyloxycarbonyllysine
  参考文献：
  名称：

  Characterisation of the antitrypanosomal activity of peptidyl α-aminoalkyl phosphonate diphenyl esters

  摘要：

  Two groups of irreversible serine peptidase inhibitors, peptidyl chloromethyl ketones and peptidyl phosphonate diphenyl esters, were examined for antitrypanosomal activity against the bloodstream form of Trypanosoma brucei brucei. Both peptidyl chloromethyl ketones and peptidyl phosphonate diphenyl esters inhibited trypsin-like peptidases of the parasites and exhibited antitrypanosomal activity at micromolar concentrations. In live T. b. brucei, labelled analogues of both of these groups of inhibitors primarily targeted an 80-kBa peptidase, possibly a serine oligopeptidase known as oligopeptidase B. In an in vivo mouse model of infection, one of these inhibitors, carbobenzyloxyglycyl-4-amidinophenylglycine phosphonate diphenyl ester, was curative at 5 mg kg(-1) day(-1) but appeared toxic at higher doses. There was no significant correlation between the inhibitory potency las evaluated against purified T. b, brucei oligopeptidase B) and the in vitro antitrypanosomal efficacy of either group of inhibitors, suggesting that these inhibitors were acting on multiple targets within the parasites, or had different cell permeability properties. These findings suggest that serine peptidases may represent novel chemotherapeutic targets in African trypanosomes. (C) 2000 Elsevier Science Inc.

  DOI：

  10.1016/s0006-2952(00)00459-7
• 作为产物：
  描述：

  5-氨基荧光素 在 sodium hydroxide 、 氯化亚砜 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 N-(5-fluoresceinyl)-5-carbamoylpentanoic acid
  参考文献：
  名称：

  Characterisation of the antitrypanosomal activity of peptidyl α-aminoalkyl phosphonate diphenyl esters

  摘要：

  Two groups of irreversible serine peptidase inhibitors, peptidyl chloromethyl ketones and peptidyl phosphonate diphenyl esters, were examined for antitrypanosomal activity against the bloodstream form of Trypanosoma brucei brucei. Both peptidyl chloromethyl ketones and peptidyl phosphonate diphenyl esters inhibited trypsin-like peptidases of the parasites and exhibited antitrypanosomal activity at micromolar concentrations. In live T. b. brucei, labelled analogues of both of these groups of inhibitors primarily targeted an 80-kBa peptidase, possibly a serine oligopeptidase known as oligopeptidase B. In an in vivo mouse model of infection, one of these inhibitors, carbobenzyloxyglycyl-4-amidinophenylglycine phosphonate diphenyl ester, was curative at 5 mg kg(-1) day(-1) but appeared toxic at higher doses. There was no significant correlation between the inhibitory potency las evaluated against purified T. b, brucei oligopeptidase B) and the in vitro antitrypanosomal efficacy of either group of inhibitors, suggesting that these inhibitors were acting on multiple targets within the parasites, or had different cell permeability properties. These findings suggest that serine peptidases may represent novel chemotherapeutic targets in African trypanosomes. (C) 2000 Elsevier Science Inc.

  DOI：

  10.1016/s0006-2952(00)00459-7

文献信息

• LIPID COMPOSITIONS AND USE THEREOF
  申请人：Neopharm, Inc.

  公开号：EP1742661A2

  公开（公告）日：2007-01-17
• JPH11140095A
  申请人：——

  公开号：JPH11140095A

  公开（公告）日：1999-05-25
• [EN] LIPID COMPOSITIONS AND USE THEREOF<br/>[FR] COMPOSITIONS LIPIDIQUES ET LEURS UTILISATIONS
  申请人：NEOPHARM INC

  公开号：WO2005067632A2

  公开（公告）日：2005-07-28

  The invention provides a composition suitable for use as a transfection agent, comprising a cationic cardiolipin analogue and, another lipid species. The composition of the present invention can facilitate transfection of a wide variety of polynucleotide species (e.g., oligodeoxyribonucleotides, plasmids, RNAi species, etc.). Moreover, the transfection agent of the present invention is effective in promoting transfection of primary cell cultures as well as transformed cells. Also, the inventive transfection agent is suitable for use both in vitro and in vivo. The inventive composition has additional uses as well, such as delivery of a variety of active agents, dermatological and cosmetic uses, and uses in agriculture. The invention further provides a method of introducing an active agent into a cell by contacting the cell with the inventive composition. The invention further provides a method of inhibiting the growth of neoplastic cells and a method of treating a patient suffering from a neoplastic disease by employing the inventive composition, wherein an active agent is an antineoplastic agent. The invention further provides a method for validating a genetic target, comprising (a) administering to a cell a composition comprising a cationic liposome and a siRNA, whereby the siRNA enters the cell inhibits the expression of a gene within the cell and (b) assaying for the inhibition of the gene. The method also provides a fluorescent/ luminescent cationic cardiolipin analogue and compositions including such analogues. Using a cationic cardiolipin analogue, the invention provides a method of tracking the migration of a lipid substance within an animal.
• Characterisation of the antitrypanosomal activity of peptidyl α-aminoalkyl phosphonate diphenyl esters
  作者：Rory E Morty、Linda Troeberg、James C Powers、Shin Ono、John D Lonsdale-Eccles、Theresa H.T Coetzer

  DOI：10.1016/s0006-2952(00)00459-7

  日期：2000.11

  Two groups of irreversible serine peptidase inhibitors, peptidyl chloromethyl ketones and peptidyl phosphonate diphenyl esters, were examined for antitrypanosomal activity against the bloodstream form of Trypanosoma brucei brucei. Both peptidyl chloromethyl ketones and peptidyl phosphonate diphenyl esters inhibited trypsin-like peptidases of the parasites and exhibited antitrypanosomal activity at micromolar concentrations. In live T. b. brucei, labelled analogues of both of these groups of inhibitors primarily targeted an 80-kBa peptidase, possibly a serine oligopeptidase known as oligopeptidase B. In an in vivo mouse model of infection, one of these inhibitors, carbobenzyloxyglycyl-4-amidinophenylglycine phosphonate diphenyl ester, was curative at 5 mg kg(-1) day(-1) but appeared toxic at higher doses. There was no significant correlation between the inhibitory potency las evaluated against purified T. b, brucei oligopeptidase B) and the in vitro antitrypanosomal efficacy of either group of inhibitors, suggesting that these inhibitors were acting on multiple targets within the parasites, or had different cell permeability properties. These findings suggest that serine peptidases may represent novel chemotherapeutic targets in African trypanosomes. (C) 2000 Elsevier Science Inc.