8-(4-methoxybenzylthio)-3,6-dioxaoctyl tosylate | 374807-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 8-(4-methoxybenzylthio)-3,6-dioxaoctyl tosylate
• 英文别名: 2-[2-[2-[(4-methoxyphenyl)methylsulfanyl]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate
• CAS: 374807-95-1
• 化学式: C₂₁H₂₈O₆S₂
• 分子量: 440.582
• InChiKey: KBPRTEDYMJNACJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-(4-methoxybenzylthio)-3,6-dioxaoctyl tosylate 在 caesium carbonate 、 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 42.5h， 生成 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 作用下， 以 乙醇 为溶剂， 反应 42.5h， 生成 8-(4-methoxybenzylthio)-3,6-dioxaoctyl tosylate
  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

• Linker arms for nanocrystals and compounds thereof
  申请人：Rosenthal J. Sandra

  公开号：US20050192430A1

  公开（公告）日：2005-09-01

  A nanocrystal compound comprising: a nanocrystal, and attached thereto a compound of the following formula: n is 0 or an integer from 1 to 48; X and Z are independently O, NH, N—R, S, CH 2 , CO, COHN, NHCO, SO, SO 2 NH, NHSO 2 , carbamate and thio carbamate; R is alkyl or aryl; r is 0 or an integer from 1 to 15; and wherein S is the attachment point to a nanocrystal compound. The nanocrystal compounds of the present invention are useful fluorescent labels.

  一种纳米晶体化合物，包括：纳米晶体，以及连接到其中的以下式子的化合物：n为0或1到48的整数；X和Z分别是O、NH、N—R、S、CH2、CO、COHN、NHCO、SO、SO2NH、NHSO2、carbamate和thio carbamate；R是烷基或芳基；r为0或1到15的整数；其中S是连接到纳米晶体化合物的连接点。本发明的纳米晶体化合物是有用的荧光标记物。
• [EN] LINKER ARMS FOR NANOCRYSTALS AND COMPOUNDS THEREOF<br/>[FR] BRAS DE LIAISON POUR NANOCRISTAUX ET COMPOSES DE CES DERNIERS
  申请人：UNIV VANDERBILT

  公开号：WO2001090716A2

  公开（公告）日：2001-11-29

  This invention generally relates to nanocrystal compounds, and linker arm for nanocrystal compounds that attach the nanocrystals to the organic compounds. The nanocrystal compound comprises a nanocrystal, linker arm, and organic compound. Preferably, the organic compound is a biologically active compound that can provide a fluorescent sensor. Preferably, the linker arm is a polyether chain with an attachment point for the nanocrystal and an attachment point for the organic compound. Specifically, the nanocrystal is attached to the linker arm through a R group and the organic compound is attached to the linker arm through a R2 group.R is a bond or is selected from the group consisting of: SH, O(CH2(n)O)nSH, NH(CH2(n)O)nSH, NH(CH2(n)NH)SH, S(CH2(n)O)nSH, and S(CH2(n)S)SH. n is 1-10, with S being attached to the nanocrystal. R2 is a bond or selected from the group consisting of carbonyl, NH, S, CONH, COO, S, C1-10 alkyl, carbamate, and thiocarbamate.
• 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.