6-[(methylcarbamoyl)methyl]-3,10-di(carboxymethyl)-3,6,10-triazadodecanedioic acid | 844682-92-4

• 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: 6-[(methylcarbamoyl)methyl]-3,10-di(carboxymethyl)-3,6,10-triazadodecanedioic acid
• 英文别名: 2-[3-[2-[Bis(carboxymethyl)amino]ethyl-[2-(methylamino)-2-oxoethyl]amino]propyl-(carboxymethyl)amino]acetic acid；2-[3-[2-[bis(carboxymethyl)amino]ethyl-[2-(methylamino)-2-oxoethyl]amino]propyl-(carboxymethyl)amino]acetic acid
• CAS: 844682-92-4
• 化学式: C₁₆H₂₈N₄O₉
• 分子量: 420.42
• InChiKey: QAJQLWLFERSXQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.4
• 重原子数：
  29
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  188
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  6-[(methylcarbamoyl)methyl]-3,10-di(carboxymethyl)-3,6,10-triazadodecanedioic acid 、 氯化镧 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 [La(6-[(methylcarbamoyl)methyl]-3,10-di(carboxylatomethyl)-3,6,10-triazadodecanedioato)](1-)
  参考文献：
  名称：

  Synthesis and Characterization of the Novel Monoamide Derivatives of Gd−TTDA

  摘要：

  For this study, the N'-monoamide derivatives of TTDA (3,6,10-tri(carboxymethyl)-3,6,10-triazadodecanedioic acid), N'-methylamide (TTDA-MA), N'-benzylamide (TTDA-BA), and N'-2-methoxybenzylamide (TTDA-MOBA), were synthesized. Their protonation constants and stability constants (log K-ML'S) formed with Ca2+, Zn2+, Cu2+, and Gd3+ were determined by potentiometric titration in 0.10 M Me4NCl at 25.0 +/- 0.1 degreesC. The relaxivity values of [Gd(TTDA-MA)](-), [Gd(TTDA-BA)](-), and [Gd(TTDA-MOBA)](-) remained constant with respect to pH changes over the range 4.5-12.0. The O-17 NMR chemical shift of H2O induced by [Dy(TTDA-MA)(H2O)](-) at pH 6.80 showed 0.9 inner-sphere water molecules. Water proton relaxivity values for [Gd(TTDA-MA)(H2O)](-), [Gd(TTDA-BA)(H2O)](-), and [Gd(TTDA-MOBA)(H2O)](-) at 37.0 +/- 0.1 degreesC and 20 MHz are 3.89, 4.21, and 4.25, respectively. The water-exchange lifetime (tau(M)) and rotational correlation time (tau(R)) of [Gd(TTDA-MA)(H2O)](-), [Gd(TTDA-BA)(H2O)](-), and [Gd(TTDAMOBA)(H2O)](-) are obtained from reduced the 170 relaxation rate and chemical shifts of H-2 O-17. The H-2 NMR longitudinal relaxation rates of the deuterated diamagnetic lanthanum complexes for the rotational correlation time 2 were also thoroughly investigated. The water-exchange rates (k(ex)(298)) for [Gd(TTDA-MA)(H2O)](-), [Gd(TTDA-BA)-(H2O)](-), and [Gd(TTDA-MOBA)(H2O)](-) are lower than that of [Gd(TTDA)(H2O)](2-) but significantly higher than those of [Gd(DTPA)(H2O)](2-) and [Gd(DTPA-BMA)(H2O)]. The rotational correlation times for [Gd(TTDA-BA)(H2O)](-) and [Gd(TTDA-MOBA)(H2O)](-) are significantly longer than those of [Gd(TTDA)(H2O)](2-) and [Gd(DTPA)(H2O)](2-) complexes. The marked increase of the relaxivity of [Gd(TTDA-BA)(H2O)](-) and [Gd(TTDA-MOBA)(H2O)](-) results mainly from their longer rotational correlation time. The noncovalent interaction between human serum albumin (HSA) and [Gd(TTDA-BA)(H2O)](-) and [Gd(TTDA-MOBA)(H2O)](-) complexes containing a hydrophobic substituent was investigated by measuring the water proton relaxation rate of the aqueous solutions. The binding association constant (K-A) values are 1.0 +/- 0.2 x 10(3) and 1.3 +/- 0.2 x 10(3) M-1 for [Gd(TTDA-BA)(H2O)](-) and [Gd(TTDAMOBA)(H2O)](-), which indicates a stronger interaction of [Gd(TTDA-BA)(H2O)](-) and [Gd(TTDA-MOBA)(H2O)](-) with HSA.

  DOI：

  10.1021/ic049401w

文献信息

• Synthesis and Characterization of the Novel Monoamide Derivatives of Gd−TTDA
  作者：Yun-Ming Wang、Cha-Ru Li、Yu-Chin Huang、Ming-Hung Ou、Gin-Chung Liu

  DOI：10.1021/ic049401w

  日期：2005.1.1

  For this study, the N'-monoamide derivatives of TTDA (3,6,10-tri(carboxymethyl)-3,6,10-triazadodecanedioic acid), N'-methylamide (TTDA-MA), N'-benzylamide (TTDA-BA), and N'-2-methoxybenzylamide (TTDA-MOBA), were synthesized. Their protonation constants and stability constants (log K-ML'S) formed with Ca2+, Zn2+, Cu2+, and Gd3+ were determined by potentiometric titration in 0.10 M Me4NCl at 25.0 +/- 0.1 degreesC. The relaxivity values of [Gd(TTDA-MA)](-), [Gd(TTDA-BA)](-), and [Gd(TTDA-MOBA)](-) remained constant with respect to pH changes over the range 4.5-12.0. The O-17 NMR chemical shift of H2O induced by [Dy(TTDA-MA)(H2O)](-) at pH 6.80 showed 0.9 inner-sphere water molecules. Water proton relaxivity values for [Gd(TTDA-MA)(H2O)](-), [Gd(TTDA-BA)(H2O)](-), and [Gd(TTDA-MOBA)(H2O)](-) at 37.0 +/- 0.1 degreesC and 20 MHz are 3.89, 4.21, and 4.25, respectively. The water-exchange lifetime (tau(M)) and rotational correlation time (tau(R)) of [Gd(TTDA-MA)(H2O)](-), [Gd(TTDA-BA)(H2O)](-), and [Gd(TTDAMOBA)(H2O)](-) are obtained from reduced the 170 relaxation rate and chemical shifts of H-2 O-17. The H-2 NMR longitudinal relaxation rates of the deuterated diamagnetic lanthanum complexes for the rotational correlation time 2 were also thoroughly investigated. The water-exchange rates (k(ex)(298)) for [Gd(TTDA-MA)(H2O)](-), [Gd(TTDA-BA)-(H2O)](-), and [Gd(TTDA-MOBA)(H2O)](-) are lower than that of [Gd(TTDA)(H2O)](2-) but significantly higher than those of [Gd(DTPA)(H2O)](2-) and [Gd(DTPA-BMA)(H2O)]. The rotational correlation times for [Gd(TTDA-BA)(H2O)](-) and [Gd(TTDA-MOBA)(H2O)](-) are significantly longer than those of [Gd(TTDA)(H2O)](2-) and [Gd(DTPA)(H2O)](2-) complexes. The marked increase of the relaxivity of [Gd(TTDA-BA)(H2O)](-) and [Gd(TTDA-MOBA)(H2O)](-) results mainly from their longer rotational correlation time. The noncovalent interaction between human serum albumin (HSA) and [Gd(TTDA-BA)(H2O)](-) and [Gd(TTDA-MOBA)(H2O)](-) complexes containing a hydrophobic substituent was investigated by measuring the water proton relaxation rate of the aqueous solutions. The binding association constant (K-A) values are 1.0 +/- 0.2 x 10(3) and 1.3 +/- 0.2 x 10(3) M-1 for [Gd(TTDA-BA)(H2O)](-) and [Gd(TTDAMOBA)(H2O)](-), which indicates a stronger interaction of [Gd(TTDA-BA)(H2O)](-) and [Gd(TTDA-MOBA)(H2O)](-) with HSA.