1-[3-[2-(N,N-phthalimido)ethyl]-1H-indol-3-yloxy]-3,6-dioxa-8-(4-methoxybenzylthio)octane | 374807-98-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1-[3-[2-(N,N-phthalimido)ethyl]-1H-indol-3-yloxy]-3,6-dioxa-8-(4-methoxybenzylthio)octane
• 英文别名: 2-[2-[5-[2-[2-[2-[(4-methoxyphenyl)methylsulfanyl]ethoxy]ethoxy]ethoxy]-1H-indol-3-yl]ethyl]isoindole-1,3-dione
• CAS: 374807-98-4
• 化学式: C₃₂H₃₄N₂O₆S
• 分子量: 574.698
• InChiKey: XHAKRBGXGWEOSD-UHFFFAOYSA-N

物化性质

• 沸点：
  762.4±60.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[3-[2-(N,N-phthalimido)ethyl]-1H-indol-3-yloxy]-3,6-dioxa-8-(4-methoxybenzylthio)octane 在 一水合肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 18.5h， 以51%的产率得到1-[3-(2-aminoethyl)-1H-indol-3-yloxy]-3,6-dioxa-8-(4-methoxybenzylthio)octane
  参考文献：
  名称：

  Targeting Cell Surface Receptors with Ligand-Conjugated Nanocrystals

  摘要：

  To explore the potential for use of ligand-conjugated nanocrystals to target cell surface receptors, ion channels, and transporters, we explored the ability of serotonin-labeled CdSe nanocrystals (SNACs) to interact with antidepressant-sensitive, human and Drosophila serotonin transporters (hSERT, dSERT) expressed in HeLa and HEK-293 cells. Unlike unconjugated nanocrystals, SNACs were found to dose-dependently inhibit transport of radiolabeled serotonin by hSERT and dSERT, with an estimated half-maximal activity (EC50) of 33 (dSERT) and 99 muM (hSERT). When serotonin was conjugated to the nanocrystal through a linker arm (LSNACs), the EC50 for hSERT was determined to be 115 muM. Electrophysiology measurements indicated that LSNACs did not elicit currents from the serotonin-3 (5HT(3)) receptor but did produce currents when exposed to the transporter, which are similar to those elicited by antagonists. Moreover, fluorescent LSNACs were found to label SERT-transfected cells but did not label either nontransfected cells or transfected cells coincubated with the high-affinity SERT antagonist paroxetine. These findings support further consideration of ligand-conjugated nanocrystals as versatile probes of membrane proteins in living cells.

  DOI：

  10.1021/ja003486s
• 作为产物：
  描述：

  2-氯乙氧基-2-乙氧基二乙醇 在 吡啶 、 sodium ethanolate 、 caesium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 66.5h， 生成 1-[3-[2-(N,N-phthalimido)ethyl]-1H-indol-3-yloxy]-3,6-dioxa-8-(4-methoxybenzylthio)octane
  参考文献：
  名称：

  Targeting Cell Surface Receptors with Ligand-Conjugated Nanocrystals

  摘要：

  To explore the potential for use of ligand-conjugated nanocrystals to target cell surface receptors, ion channels, and transporters, we explored the ability of serotonin-labeled CdSe nanocrystals (SNACs) to interact with antidepressant-sensitive, human and Drosophila serotonin transporters (hSERT, dSERT) expressed in HeLa and HEK-293 cells. Unlike unconjugated nanocrystals, SNACs were found to dose-dependently inhibit transport of radiolabeled serotonin by hSERT and dSERT, with an estimated half-maximal activity (EC50) of 33 (dSERT) and 99 muM (hSERT). When serotonin was conjugated to the nanocrystal through a linker arm (LSNACs), the EC50 for hSERT was determined to be 115 muM. Electrophysiology measurements indicated that LSNACs did not elicit currents from the serotonin-3 (5HT(3)) receptor but did produce currents when exposed to the transporter, which are similar to those elicited by antagonists. Moreover, fluorescent LSNACs were found to label SERT-transfected cells but did not label either nontransfected cells or transfected cells coincubated with the high-affinity SERT antagonist paroxetine. These findings support further consideration of ligand-conjugated nanocrystals as versatile probes of membrane proteins in living cells.

  DOI：

  10.1021/ja003486s

文献信息

• Targeting Cell Surface Receptors with Ligand-Conjugated Nanocrystals
  作者：Sandra J. Rosenthal、Ian Tomlinson、Erika M. Adkins、Sally Schroeter、Scott Adams、Laura Swafford、James McBride、Yongqiang Wang、Louis J. DeFelice、Randy D. Blakely

  DOI：10.1021/ja003486s

  日期：2002.5.1

  To explore the potential for use of ligand-conjugated nanocrystals to target cell surface receptors, ion channels, and transporters, we explored the ability of serotonin-labeled CdSe nanocrystals (SNACs) to interact with antidepressant-sensitive, human and Drosophila serotonin transporters (hSERT, dSERT) expressed in HeLa and HEK-293 cells. Unlike unconjugated nanocrystals, SNACs were found to dose-dependently inhibit transport of radiolabeled serotonin by hSERT and dSERT, with an estimated half-maximal activity (EC50) of 33 (dSERT) and 99 muM (hSERT). When serotonin was conjugated to the nanocrystal through a linker arm (LSNACs), the EC50 for hSERT was determined to be 115 muM. Electrophysiology measurements indicated that LSNACs did not elicit currents from the serotonin-3 (5HT(3)) receptor but did produce currents when exposed to the transporter, which are similar to those elicited by antagonists. Moreover, fluorescent LSNACs were found to label SERT-transfected cells but did not label either nontransfected cells or transfected cells coincubated with the high-affinity SERT antagonist paroxetine. These findings support further consideration of ligand-conjugated nanocrystals as versatile probes of membrane proteins in living cells.