S-benzylmercaptoacetylglycylglycine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: S-benzylmercaptoacetylglycylglycine
• 英文别名: S-benzyl-mercaptoacetyldiglycine；2-[[2-[(2-Benzylsulfanylacetyl)amino]acetyl]amino]acetic acid
• 化学式: C₁₃H₁₆N₂O₄S
• 分子量: 296.347
• InChiKey: ODVHHJMXKIKYDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-benzylmercaptoacetylglycylglycine 、 4-(2-氨乙基)苯磺酰胺 在 4-二甲氨基吡啶 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以66%的产率得到
  参考文献：
  名称：

  用于体内可视化CA IX的99m Tc-磺酰胺衍生物的开发和生物学评估，作为替代性肿瘤缺氧标记物

  摘要：

  体内与肿瘤缺氧相关的标志物（例如内源性跨膜蛋白CA IX）的可视化可能会导致在实体瘤管理中的新型治疗和诊断应用。在这项研究中，已将4-（2-氨基乙基）苯磺酰胺（AEBS， 对于CA IX ，K i = 33 nM）与双（氨基乙硫醇）（BAT）和巯基乙酰基二甘氨酸（MAG 2）四登酸酯配体共轭，并用99m Tc放射性标记了该共轭物。分别获得阴离子和中性的99m Tc标记的磺酰胺衍生物。还制备了相应的rh类似物，并显示出对hCA IX（K i = 59–66 nM）。另外，将第二代bis AEBS与MAG 2缀合并用99m Tc标记，并且还评价了靶向CA IX的所得非对映异构体。在携带HT-29结直肠异种移植物的小鼠中进行的生物分布研究表明，对于所有示踪剂，在pi 0.5 h时最大肿瘤吸收率<0.5％ID / g。体内放射性代谢物分析表明，与中性复合物（完整度为28％）相比，在pi 1 h时，MAG

  DOI：

  10.1016/j.ejmech.2013.10.027
• 作为产物：
  描述：

  S-苄基巯基乙酸 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 17.0h， 生成 S-benzylmercaptoacetylglycylglycine
  参考文献：
  名称：

  Comparative evaluation of99mTc-MAG2-oligodeoxynucleotides with phosphodiester or phosphorothioate backbones: preparation, stability and biodistribution

  摘要：

  Antisense oligodeoxynucleotides (ODNs) conjugated to a suitable bifunctional chelating agent and labelled with a suitable radionuclide could become useful in the diagnosis and differentiation of cancers. Radiolabelled natural DNA with phosphodiester (PO) backbone is a candidate for use in imaging, while phosphorothioate (PS) ODNs already are proving their efficacy in antisense therapy. In this study, two PO and two PS ODNs have been conjugated with the N2SO chelator MAG2 in a procedure designed to make a N3S tetraligand which forms stable complexes with technetium-99m. Depending on the S-protecting group used and reaction conditions employed, labelling yields of more than 90 % can routinely be obtained. The Tc-99m-MAG2-ODNs are stable in solution, even in the presence of a 30-fold excess of cysteine. However, at higher concentrations of cysteine and in foetal calf serum they are not stable. In vivo in mice, the PO Tc-99m-MAG2-ODNs are degraded more than 50 % in 5 min, while the PS analogues remain intact. The PS and PO Tc-99m-MAG2-ODNs are distributed in a similar fashion in normal mice, except for a higher liver retention of the PO Tc-99m-MAG2-ODNs at 60 min.

  DOI：

  10.1002/(sici)1099-1344(199908)42:8<737::aid-jlcr233>3.0.co;2-y

文献信息

• Comparative evaluation of99mTc-MAG2-oligodeoxynucleotides with phosphodiester or phosphorothioate backbones: preparation, stability and biodistribution
  作者：O. K. Hjelstuen、B. C. By、B. Cleynhens、H. M. Ormstad、T. E. Roald、H. H. Tønnesen、P. O. Bremer、A. M. Verbruggen

  DOI：10.1002/(sici)1099-1344(199908)42:8<737::aid-jlcr233>3.0.co;2-y

  日期：1999.8

  Antisense oligodeoxynucleotides (ODNs) conjugated to a suitable bifunctional chelating agent and labelled with a suitable radionuclide could become useful in the diagnosis and differentiation of cancers. Radiolabelled natural DNA with phosphodiester (PO) backbone is a candidate for use in imaging, while phosphorothioate (PS) ODNs already are proving their efficacy in antisense therapy. In this study, two PO and two PS ODNs have been conjugated with the N2SO chelator MAG2 in a procedure designed to make a N3S tetraligand which forms stable complexes with technetium-99m. Depending on the S-protecting group used and reaction conditions employed, labelling yields of more than 90 % can routinely be obtained. The Tc-99m-MAG2-ODNs are stable in solution, even in the presence of a 30-fold excess of cysteine. However, at higher concentrations of cysteine and in foetal calf serum they are not stable. In vivo in mice, the PO Tc-99m-MAG2-ODNs are degraded more than 50 % in 5 min, while the PS analogues remain intact. The PS and PO Tc-99m-MAG2-ODNs are distributed in a similar fashion in normal mice, except for a higher liver retention of the PO Tc-99m-MAG2-ODNs at 60 min.
• Development and biological evaluation of 99mTc-sulfonamide derivatives for in vivo visualization of CA IX as surrogate tumor hypoxia markers
  作者：Vamsidhar Akurathi、Ludwig Dubois、Sofie Celen、Natasja G. Lieuwes、Satish K. Chitneni、Bernard J. Cleynhens、Alessio Innocenti、Claudiu T. Supuran、Alfons M. Verbruggen、Philippe Lambin、Guy M. Bormans

  DOI：10.1016/j.ejmech.2013.10.027

  日期：2014.1

  good inhibitory activities against hCA IX (Ki = 59–66 nM). In addition, a second generation bis AEBS was conjugated with MAG2 and labeled with 99mTc, and the obtained diastereomers were also evaluated in targeting CA IX. Biodistribution studies in mice bearing HT-29 colorectal xenografts revealed a maximum tumor uptake of <0.5% ID/g at 0.5 h p.i for all the tracers. In vivo radiometabolite analysis indicated

  体内与肿瘤缺氧相关的标志物（例如内源性跨膜蛋白CA IX）的可视化可能会导致在实体瘤管理中的新型治疗和诊断应用。在这项研究中，已将4-（2-氨基乙基）苯磺酰胺（AEBS， 对于CA IX ，K i = 33 nM）与双（氨基乙硫醇）（BAT）和巯基乙酰基二甘氨酸（MAG 2）四登酸酯配体共轭，并用99m Tc放射性标记了该共轭物。分别获得阴离子和中性的99m Tc标记的磺酰胺衍生物。还制备了相应的rh类似物，并显示出对hCA IX（K i = 59–66 nM）。另外，将第二代bis AEBS与MAG 2缀合并用99m Tc标记，并且还评价了靶向CA IX的所得非对映异构体。在携带HT-29结直肠异种移植物的小鼠中进行的生物分布研究表明，对于所有示踪剂，在pi 0.5 h时最大肿瘤吸收率<0.5％ID / g。体内放射性代谢物分析表明，与中性复合物（完整度为28％）相比，在pi 1 h时，MAG