2-succinamido 2-deoxy D-glucose | 159701-53-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-succinamido 2-deoxy D-glucose
• 英文别名: 2-[(3-carboxy-1-oxopropyl)amino]-2-deoxy-D-glucose；4-oxo-4-[[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]amino]butanoic acid
• CAS: 159701-53-8
• 化学式: C₁₀H₁₇NO₈
• 分子量: 279.247
• InChiKey: YCADUTALRCFWBJ-RGNARYMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ^99mtechnetium pertechnetate 、 2-succinamido 2-deoxy D-glucose 在 盐酸 、 tin(II) chloride dihdyrate 、 sodium hydroxide 作用下， 以 aq. phosphate buffer 、 水 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  Synthesis and evaluation of 99mTc–2-[(3-carboxy-1-oxopropyl)amino]-2-deoxy-d-glucose as a potential tumor imaging agent

  摘要：

  The 2-[(3-carboxy-1-oxopropyl)amino]-2-deoxy-D-glucose (CPADG) was synthesized and radiolabeled with (99m)TcO4(-) to obtain the (99m)Tc-CPADG complex in high yield. It was stable over 6 h in saline at room temperature and in serum at 37 °C. The partition coefficient and electrophoresis results indicated that the complex was hydrophilic and cationic. In vitro cell studies showed there was an increase in the uptake of (99m)Tc-CPADG as a function of incubation time and (99m)Tc-CPADG was possibly transported via the glucose transporters. The biodistribution of (99m)Tc-CPADG in mice bearing S 180 tumor showed that the complex accumulated in the tumor with high uptake and good retention. The tumor/blood and tumor/muscle ratios increased with time and reached 1.91 and 5.05 at 4h post-injection. Single photon emission computed tomography (SPECT) image studies showed there was an obvious accumulation in tumor sites, suggesting (99m)Tc-CPADG would be a promising candidate for tumor imaging.

  DOI：

  10.1016/j.bmcl.2014.06.051
• 作为产物：
  描述：

  2-succinamido 2-deoxy 1,3,4,6-tetra O-acetyl β-D-glucose 以86%的产率得到
  参考文献：
  名称：

  DARDOIZE, F.;GOASDOUE, C.;GOASDOUE, N.;LABORIT, H. M.;TOPALL, G., TETRAHEDRON, 45,(1989) N4, C. 7783-7794

  摘要：

  DOI：

文献信息

• Design, Synthesis and Evaluation of Dual-Modality Glyco-Nanoparticles for Tumor Imaging
  作者：Hua Zhu、Jun Zhao、Xinfeng Lin、Ye Hong、Chun Li、Zhi Yang

  DOI：10.3390/molecules18066425

  日期：——

  d-Glucosamine (DG) was conjugated to a core-cross linked polymeric micelle (CCPM) system equipped with both a near-infrared fluorophore (NIRF) and a gamma emitter (111In). The resultant nano-scale tumor-targeting imaging tracer, 111In-DG-NIRF-CCPM, selectively accumulated in a human epithelial carcinoma A-431 xenograft model in mice. At 24 hrs post injection, the tumor uptake was 2.62 ± 0.80 % of the injected dose per gram of tissue (%ID/g). Tumors were clearly delineated in both single-photon emission computed tomography (SPECT) and optical imaging. The results suggest that the prepared imaging tracer is a promising agent for tumor diagnosis.

  d-葡萄糖胺（DG）与一种核-交联聚合物胶束（CCPM）系统结合，该系统配备了近红外荧光染料（NIRF）和γ发射体（111In）。所得到纳米尺度的肿瘤靶向成像示踪剂，111In-DG-NIRF-CCPM，在人上皮癌细胞癌A-431异种移植小鼠模型中选择性积累。注射后24小时，肿瘤摄取量为每克组织注射剂量的2.62 ± 0.80%（%ID/g）。肿瘤在单光子发射计算机断层扫描（SPECT）和光学成像中都能清晰地描绘出来。结果表明，制备的成像示踪剂是一种有前途的肿瘤诊断剂。
• KR10223615
  申请人：——

  公开号：——

  公开（公告）日：——
• Carboxy derivatized glucosamine is a potent inhibitor of matrix metalloproteinase-9 in HT1080 cells
  作者：Eresha Mendis、Moon-Moo Kim、Niranjan Rajapakse、Se-Kwon Kim

  DOI：10.1016/j.bmcl.2006.03.077

  日期：2006.6

  Experimental evidences have confirmed that matrix metal loprotemases (MMPs) play a fundamental role in a wide variety of pathologic conditions and recent advances in medicinal chemistry approach to the design of MMP inhibitors with desired structural and functional properties. Among MMPs, MMP-9 has demonstrated to play a major role in the establishment of metastases and it is substantially increased in the majority of malignant tumors. Inhibition of MMP-9 is thought to have a therapeutic benefit to cancer. Results of this study present a novel synthetic MMP-9 inhibitor that downregulates MMP-9 expression level in HT1080, human fibrosarcoma cells. (c) 2006 Elsevier Ltd. All rights reserved.
• KIM, WAN, S.;JEONG, SEO, Y.;MCREA, J. C.
  作者：KIM, WAN, S.、JEONG, SEO, Y.、MCREA, J. C.

  DOI：——

  日期：——
• Synthesis and evaluation of 99mTc–2-[(3-carboxy-1-oxopropyl)amino]-2-deoxy-d-glucose as a potential tumor imaging agent
  作者：Yue Wang、Jingjing Zhu、Xiaoqing Song、Xuebin Wang、Jigang Yang、Junbo Zhang

  DOI：10.1016/j.bmcl.2014.06.051

  日期：2014.8

  The 2-[(3-carboxy-1-oxopropyl)amino]-2-deoxy-D-glucose (CPADG) was synthesized and radiolabeled with (99m)TcO4(-) to obtain the (99m)Tc-CPADG complex in high yield. It was stable over 6 h in saline at room temperature and in serum at 37 °C. The partition coefficient and electrophoresis results indicated that the complex was hydrophilic and cationic. In vitro cell studies showed there was an increase in the uptake of (99m)Tc-CPADG as a function of incubation time and (99m)Tc-CPADG was possibly transported via the glucose transporters. The biodistribution of (99m)Tc-CPADG in mice bearing S 180 tumor showed that the complex accumulated in the tumor with high uptake and good retention. The tumor/blood and tumor/muscle ratios increased with time and reached 1.91 and 5.05 at 4h post-injection. Single photon emission computed tomography (SPECT) image studies showed there was an obvious accumulation in tumor sites, suggesting (99m)Tc-CPADG would be a promising candidate for tumor imaging.