[2-(iminodiacetato)ethyl]-β-D-glucopyranoside | 317321-95-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [2-(iminodiacetato)ethyl]-β-D-glucopyranoside
• 英文别名: iminodiacetic acid-glucose；2-[carboxymethyl-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]amino]acetic acid
• CAS: 317321-95-2
• 化学式: C₁₂H₂₁NO₁₀
• 分子量: 339.299
• InChiKey: GDBPDPJUECFLCY-UJDFUTJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  177
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  fac-triaquatricarbonyltechnetium-99m(1+) 、 [2-(iminodiacetato)ethyl]-β-D-glucopyranoside 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 (99m)Tc(CO)3-(IDA-glucose)
  参考文献：
  名称：

  GROUP(VII) TRANSITION-METAL COMPLEXES WITH MULTIDENTATE AMINOPOLYCARBOXYLATE LIGANDS AND A KIT FOR PRODUCING THEM

  摘要：

  公开号：

  EP1192166B1
• 作为产物：
  描述：

  2-hydroxyethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 Lindlar's catalyst 吡啶 、 sodium azide 、 氢气 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、101.33 kPa 条件下， 反应 34.0h， 生成 [2-(iminodiacetato)ethyl]-β-D-glucopyranoside
  参考文献：
  名称：

  用于过渡金属络合的葡萄糖和 2-脱氧葡萄糖的衍生化：与有机金属 99mTc 和 Re 前体的取代反应和基础 NMR 研究

  摘要：

  报道了葡萄糖和 2-脱氧葡萄糖在 C-1 位进行双功能化以实现过渡金属配位的合成策略。特别是合成和研究了可能用于诊断核医学的有机金属锝和铼配合物。具体而言，常见的亚氨基二乙酸 (IDA) 部分通过乙烯间隔基团 O-糖苷连接，以产生纯的 α-（在 2-脱氧葡萄糖的情况下）和 β-端基异构体（在葡萄糖的情况下）。糖衍生物与有机金属前体 [M(H2O)3(CO)3]+ (M = 99mTc, Re) 的反应以高产率产生了水溶性和水稳定性的单一产品。金属前体的三个水分子的置换以及金属-三羰基核的三齿配位仅通过胺和 IDA 螯合物的两个羧酸官能团通过 1D 和 2D 1H NMR 光谱、质谱法验证, 和红外光谱。放射性标记的产品 (99mTc) 在生理磷酸盐缓冲液 (pH = 7.4) 和人血浆中在 37 摄氏度的 24 小时内证明了它们在体外具有出色的稳定性。

  DOI：

  10.1002/1521-3765(20010504)7:9<1868::aid-chem1868>3.0.co;2-h

文献信息

• Technetium glucose complexes as potential cancer imaging agents
  作者：Rosina Dapueto、Rodrigo B. Aguiar、María Moreno、Camila M.L. Machado、Fabio L.N. Marques、Juan P. Gambini、Roger Chammas、Pablo Cabral、Williams Porcal

  DOI：10.1016/j.bmcl.2015.07.098

  日期：2015.10

  GLUT's (facilitative glucose transporters) over-expression in tumor cells has allowed the detection of several cancer types, using a glucose analogue (F-18-FDG) with PET images, worldwide. New glucose analogs radiolabeled with Tc-99m could be a less-expensive and more accessible alternative for diagnosis using SPECT imaging. D-Glucose (Tc-99m-IDAG) and 2-D-deoxyglucose (Tc-99m-AADG) organometallic complexes were proposed and studied as potential F-18-FDG surrogates. The glucose complexes were prepared and evaluated as potential cancer imaging agents, in a melanoma tumor model. Iminodiacetic acid (IDA) and aminoacetate (AA) moieties were chosen as chelating system for radiolabeling with Tc-99m. Tumor uptake of the formed complexes was evaluated in B16 murine cell line in vitro and in vivo in melanoma bearing C57BL/6 mice. In vitro and in vivo studies were conducted with F-18-FDG in order to compare the uptake of Tc-99m-glucose complexes in the tumor model. IDAG and AADG compounds were synthesized and radiolabeled with (TcO4)-Tc-99m to obtain the Tc-99m-IDAG and Tc-99m-AADG complexes in high yield and stability. In vitro cell studies showed maximum uptake at 60 min for complexes, Tc-99m-IDAG and Tc-99m-AADG, with 6% and 2%, respectively. Biodistribution studies showed high tumor uptake one hour post-injection, reaching tumor-to-muscle ratios of 12.1 +/- 3.73 and 2.88 +/- 1.40 for Tc-99m-IDAG and Tc-99m-AADG, respectively. SPECT and micro-SPECT-CT images acquired after the injection of Tc-99m-IDAG showed accumulation in tumor sites, suggesting that this glucose complex would be a promising candidate for cancer imaging. (C) 2015 Elsevier Ltd. All rights reserved.
• Derivatization of Glucose and 2-Deoxyglucose for Transition Metal Complexation: Substitution Reactions with Organometallic99mTc and Re Precursors and Fundamental NMR Investigations
  作者：Jeannine Petrig、Roger Schibli、Cécile Dumas、Roger Alberto、P. A. Schubiger

  DOI：10.1002/1521-3765(20010504)7:9<1868::aid-chem1868>3.0.co;2-h

  日期：2001.5.4

  2-deoxyglucose) and beta-anomer (in case of glucose). Reaction of the sugar derivatives with the organometallic precursor [M(H2O)3(CO)3]+ (M = 99mTc, Re) produced single products in high yield, which are water-soluble and water-stable. The displacement of the three water molecules of the metal precursor and thus the tridentate coordination of the metal-tricarbonyl core exclusively via the amine and the two

  报道了葡萄糖和 2-脱氧葡萄糖在 C-1 位进行双功能化以实现过渡金属配位的合成策略。特别是合成和研究了可能用于诊断核医学的有机金属锝和铼配合物。具体而言，常见的亚氨基二乙酸 (IDA) 部分通过乙烯间隔基团 O-糖苷连接，以产生纯的 α-（在 2-脱氧葡萄糖的情况下）和 β-端基异构体（在葡萄糖的情况下）。糖衍生物与有机金属前体 [M(H2O)3(CO)3]+ (M = 99mTc, Re) 的反应以高产率产生了水溶性和水稳定性的单一产品。金属前体的三个水分子的置换以及金属-三羰基核的三齿配位仅通过胺和 IDA 螯合物的两个羧酸官能团通过 1D 和 2D 1H NMR 光谱、质谱法验证, 和红外光谱。放射性标记的产品 (99mTc) 在生理磷酸盐缓冲液 (pH = 7.4) 和人血浆中在 37 摄氏度的 24 小时内证明了它们在体外具有出色的稳定性。
• GROUP(VII) TRANSITION-METAL COMPLEXES WITH MULTIDENTATE AMINOPOLYCARBOXYLATE LIGANDS AND A KIT FOR PRODUCING THEM
  申请人：MALLINCKRODT INC.

  公开号：EP1192166B1

  公开（公告）日：2004-09-29