β-D-glucuronic acid sodium salt | 75232-35-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-glucuronic acid sodium salt
• 英文别名: sodium β-D-glucopyranuronate；sodium salt of glucuronic acid；sodium β-D-glucuronate；β-sodium glucuronate；sodium D-glucuronate；sodium glucuronate；Sodium beta-d-glucuronate；sodium;(2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
• CAS: 75232-35-8
• 化学式: C₆H₉O₇*Na
• 分子量: 216.123
• InChiKey: MSXHSNHNTORCAW-YXUDEUAMSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -7.46
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  三甲基氯化锡 、 β-D-glucuronic acid sodium salt 以 乙醇 为溶剂， 以58%的产率得到Me₃Sn(Glu)
  参考文献：
  名称：

  Design, spectral characterization, anti-tumor and anti-inflammatory activity of triorganotin(IV) hydroxycarboxylates, apoptosis inducers: In vitro assessment of induction of apoptosis by enzyme, DNA-fragmentation, acridine orange and comet assays

  摘要：

  Interaction of triorganotin(IV) chlorides with sodium salt of hydroxycarboxylic acids results in the formation of triorganotin(IV) hydroxycarboxylates, R3Sn(L) [R = Me, n-Bu and Ph; L = anion of glucuronic (HGlu), gallic (HGal) and mandelic (HMal) acid]. They exhibit trigonal-bipyramidal geometry which is well supported by elemental analysis, IR, H-1, C-13, Sn-119 NMR and ESI-MS spectral data. Triorganotin(IV) hydroxycarboxylates have been screened in vitro against five cancer cell lines of human origin viz. MCF-7, HEK-293, PC-3, HCT-15 and HepG-2. Title complexes are found to be cytotoxic to mildly cytotoxic, and exhibited IC50 values in the range 4-30 mu g/mL. The results of enzyme assays viz. glutathione reductase, glutathione peroxidase, total glutathione content and lipid peroxidase assay on MCF-7 cells indicate that the reactive oxygen species generated in the cancer cells by triorganotin(IV) hydroxycarboxylates is responsible for cell death. Marginal increase of lactate dehydrogenase suggests that necrosis is also occurring to a small extent. DNA (deoxyribonucleic acid) fragmentation assay, acridine orange assay and comet assay clearly support that the cell death is mainly due to apoptosis. The results obtained for the in vivo anti-inflammatory activity (% inhibition) and toxicity (LD50 in mg/kg) suggested that the complexes have low toxicity and good anti-inflammatory activity. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2014.02.034
• 作为产物：
  描述：

  (1S,2S)-安非他酮N-1’-脱氧-beta-D-葡萄糖醛酸 在 sodium ethoxide 作用下， 以 乙醇 为溶剂， 生成 β-D-glucuronic acid sodium salt
  参考文献：
  名称：

  Design, spectral characterization, anti-tumor and anti-inflammatory activity of triorganotin(IV) hydroxycarboxylates, apoptosis inducers: In vitro assessment of induction of apoptosis by enzyme, DNA-fragmentation, acridine orange and comet assays

  摘要：

  Interaction of triorganotin(IV) chlorides with sodium salt of hydroxycarboxylic acids results in the formation of triorganotin(IV) hydroxycarboxylates, R3Sn(L) [R = Me, n-Bu and Ph; L = anion of glucuronic (HGlu), gallic (HGal) and mandelic (HMal) acid]. They exhibit trigonal-bipyramidal geometry which is well supported by elemental analysis, IR, H-1, C-13, Sn-119 NMR and ESI-MS spectral data. Triorganotin(IV) hydroxycarboxylates have been screened in vitro against five cancer cell lines of human origin viz. MCF-7, HEK-293, PC-3, HCT-15 and HepG-2. Title complexes are found to be cytotoxic to mildly cytotoxic, and exhibited IC50 values in the range 4-30 mu g/mL. The results of enzyme assays viz. glutathione reductase, glutathione peroxidase, total glutathione content and lipid peroxidase assay on MCF-7 cells indicate that the reactive oxygen species generated in the cancer cells by triorganotin(IV) hydroxycarboxylates is responsible for cell death. Marginal increase of lactate dehydrogenase suggests that necrosis is also occurring to a small extent. DNA (deoxyribonucleic acid) fragmentation assay, acridine orange assay and comet assay clearly support that the cell death is mainly due to apoptosis. The results obtained for the in vivo anti-inflammatory activity (% inhibition) and toxicity (LD50 in mg/kg) suggested that the complexes have low toxicity and good anti-inflammatory activity. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2014.02.034

文献信息

• Synthesis of Novel Glucuronide Conjugates of Retinoid Carboxylic Acids
  作者：Arun B. Barua、Christine A. Huselton、James A. Olson

  DOI：10.1080/00397919608003496

  日期：1996.4

  Abstract The synthesis and characterization of the novel glucuronide conjugates of 9-cis and 13-cis retinoic acid and of all-trans, 9-cis and 13-cis 4-oxoretinoic acid are described.

  摘要 描述了 9-顺式和 13-顺式视黄酸以及全反式、9-顺式和 13-顺式 4-氧代视黄酸的新型葡糖苷酸结合物的合成和表征。
• HIGH PERFORMANCE LIQUID CHROMATOGRAPHY OF POTENTIAL ANTITUMOR PLATINUM(II) COMPLEXES OF 1<i>R</i>,2<i>R</i>-CYCLOHEXANEDIAMINE
  作者：Masahide Noji、Kyoko Achiwa、Asami Kondo、Yoshinori Kidani

  DOI：10.1246/cl.1982.1757

  日期：1982.11.5

  High performance liquid chromatography of antitumor Pt(II) complexes of 1R,2R-cyclohexandiamine, as well as cis- and trans-DDP, dichlorodiammineplatinum(II), has been performed, using a Toyo Soda G1000PW column, eluting with 0.1 mol dm−3 Na2SO4, and various Pt(II) complexes were separated successfully.

  使用Toyo Soda G1000PW色谱柱，以0.1 mol dm−3 Na2SO4为淋洗液，对1R,2R-环己二胺、顺式和反式二苯并呋喃二氨合铂（II）的抗肿瘤铂（II）配合物进行了高效液相色谱分析，并成功分离了各种铂（II）配合物。
• Design, spectral characterization, anti-tumor and anti-inflammatory activity of triorganotin(IV) hydroxycarboxylates, apoptosis inducers: In vitro assessment of induction of apoptosis by enzyme, DNA-fragmentation, acridine orange and comet assays
  作者：Mala Nath、Monika Vats、Partha Roy

  DOI：10.1016/j.ica.2014.02.034

  日期：2014.11

  Interaction of triorganotin(IV) chlorides with sodium salt of hydroxycarboxylic acids results in the formation of triorganotin(IV) hydroxycarboxylates, R3Sn(L) [R = Me, n-Bu and Ph; L = anion of glucuronic (HGlu), gallic (HGal) and mandelic (HMal) acid]. They exhibit trigonal-bipyramidal geometry which is well supported by elemental analysis, IR, H-1, C-13, Sn-119 NMR and ESI-MS spectral data. Triorganotin(IV) hydroxycarboxylates have been screened in vitro against five cancer cell lines of human origin viz. MCF-7, HEK-293, PC-3, HCT-15 and HepG-2. Title complexes are found to be cytotoxic to mildly cytotoxic, and exhibited IC50 values in the range 4-30 mu g/mL. The results of enzyme assays viz. glutathione reductase, glutathione peroxidase, total glutathione content and lipid peroxidase assay on MCF-7 cells indicate that the reactive oxygen species generated in the cancer cells by triorganotin(IV) hydroxycarboxylates is responsible for cell death. Marginal increase of lactate dehydrogenase suggests that necrosis is also occurring to a small extent. DNA (deoxyribonucleic acid) fragmentation assay, acridine orange assay and comet assay clearly support that the cell death is mainly due to apoptosis. The results obtained for the in vivo anti-inflammatory activity (% inhibition) and toxicity (LD50 in mg/kg) suggested that the complexes have low toxicity and good anti-inflammatory activity. (C) 2014 Elsevier B.V. All rights reserved.