(4S)-4-benzyl-3,6,10-tris(carboxymethyl)-3,6,10-triazadodecanedioic acid | 445269-58-9

• 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: (4S)-4-benzyl-3,6,10-tris(carboxymethyl)-3,6,10-triazadodecanedioic acid
• 英文别名: N-{(2S)-2-[bis(carboxymethyl)amino]-3-phenylpropyl}-N-{3-[bis(carboxymethyl)amino]propyl}glycine；(4S)-4-benzyl-3,6,10-tricarboxymethyl-3,6,10-triazadodecanoic acid；2-[[(2S)-2-[bis(carboxymethyl)amino]-3-phenylpropyl]-[3-[bis(carboxymethyl)amino]propyl]amino]acetic acid
• CAS: 445269-58-9
• 化学式: C₂₂H₃₁N₃O₁₀
• 分子量: 497.502
• InChiKey: FPZMIAFWRRSFDF-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.1
• 重原子数：
  35
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  196
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  氯化镧水合物 、 (4S)-4-benzyl-3,6,10-tris(carboxymethyl)-3,6,10-triazadodecanedioic acid 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Thermodynamic Stability and Physicochemical Characterization of Ligand (4S)-4-Benzyl-3,6,10-tris(carboxymethyl)-3,6,10-triazadodecanedioic Acid (H5[(S)-4-Bz-ttda]) and Its Complexes Formed with Lanthanides, Calcium(II), Zinc(II), and Copper(II) Ions

  摘要：

  A derivative of H(5)ttda (= 3,6,10-tris(carboxymethyl)-3,6,10-triazadodecanedioic acid = N-{2-[bis(carboxymethyl)amino]ethyl}-N-{3-[bis(carboxymethyl)amino]propyl} glycine), H-5[(S)-4-Bz-ttda] (=(4S)-4-benzyl-3,6,10-tris(carboxymethyl)-3,6,10-triazadodecanedioic acid = N-{(2S)-2-[bis(carboxymethyl)amino]-3-phenylpropyl} -N-{3-[bis(carboxymethyl)amino]propyl}glycine; 1) carrying a benzyl group was synthesized and characterized. The stability constants of the complexes formed with Ca2+, Zn2+, Cu2+, and Gd3+ were determined by potentiometric methods at 25.0 +/- 0.1degrees and 0.1M ionic strength in Me4NNO3. The observed water proton relaxivity value of [Gd{(S)-4-Bz-ttda}](2-) was constant with respect to pH changes over the range pH 4.5 - 12.0. From the O-17-NMR chemical shift of H2O induced by [Dy{(S)-4-Bz-ttda}](2-) at pH 6.80, the presence of 0.9 inner-sphere water molecules was deduced. The water proton spin-lattice relaxation rate for [Gd{(S)-4-Bz-ttda}](2-) at 37.0 +/- 0.1degrees and 20 MHz was 4.90 +/- 0.05 mM(-1) s(-1). The EPR transverse electronic relaxation rate and O-17-NMR transverse-relaxation time for the exchange lifetime of the coordinated H2O molecule (tau(M)), and H-2-NMR longitudinal-relaxation rate of the deuterated diamagnetic lanthanum complex for the rotational correlation time (tau(R)) were thoroughly investigated, and the results Were compared with those previously reported for the other lanthanide(III) complexes, The exchange lifetime (tau(M)) for [Gd{(S)-4-Bz-ttda}](2-) (2.3 +/- 13 ns) was significantly shorter than that of the [Gd(dtpa)(H2O)](2-) complex (dtpa = diethylenetriaminepentaacetic acid). The rotational correlation time tau(R) for [Gd{(S)-4-Bz-ttda}](2-) (70 +/- 6 ps) was slightly longer than that of the [Gd(dtpa)(H2O)](2-) Complex. The marked increase of relaxivity of [Gd{(S)-4-Bz-ttda}](2-) mainly resulted from its longer rotational time rather than from its fast water-exchange rate. The noncovalent interaction between human serum albumin (HSA) and the [Gd{(S)-4-Bz-ttda}](2-) complex containing the hydrophobic substituent was investigated by measuring the solvent proton relaxation rate of the aqueous solutions. The association constant (K-A) was less than 100 M-1. indicating a weaker interaction of [Gd{(S)-4-Bz-ttda}](2-) with HSA.

  DOI：

  10.1002/1522-2675(200204)85:4<1033::aid-hlca1033>3.0.co;2-n
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 N-[(2S)-2-amino-3-phenylpropyl]propane-1,3-diamine 在 potassium carbonate 、 盐酸 作用下， 以 乙腈 、 水 为溶剂， 反应 24.0h， 以37.89%的产率得到(4S)-4-benzyl-3,6,10-tris(carboxymethyl)-3,6,10-triazadodecanedioic acid
  参考文献：
  名称：

  Thermodynamic Stability and Physicochemical Characterization of Ligand (4S)-4-Benzyl-3,6,10-tris(carboxymethyl)-3,6,10-triazadodecanedioic Acid (H5[(S)-4-Bz-ttda]) and Its Complexes Formed with Lanthanides, Calcium(II), Zinc(II), and Copper(II) Ions

  摘要：

  A derivative of H(5)ttda (= 3,6,10-tris(carboxymethyl)-3,6,10-triazadodecanedioic acid = N-{2-[bis(carboxymethyl)amino]ethyl}-N-{3-[bis(carboxymethyl)amino]propyl} glycine), H-5[(S)-4-Bz-ttda] (=(4S)-4-benzyl-3,6,10-tris(carboxymethyl)-3,6,10-triazadodecanedioic acid = N-{(2S)-2-[bis(carboxymethyl)amino]-3-phenylpropyl} -N-{3-[bis(carboxymethyl)amino]propyl}glycine; 1) carrying a benzyl group was synthesized and characterized. The stability constants of the complexes formed with Ca2+, Zn2+, Cu2+, and Gd3+ were determined by potentiometric methods at 25.0 +/- 0.1degrees and 0.1M ionic strength in Me4NNO3. The observed water proton relaxivity value of [Gd{(S)-4-Bz-ttda}](2-) was constant with respect to pH changes over the range pH 4.5 - 12.0. From the O-17-NMR chemical shift of H2O induced by [Dy{(S)-4-Bz-ttda}](2-) at pH 6.80, the presence of 0.9 inner-sphere water molecules was deduced. The water proton spin-lattice relaxation rate for [Gd{(S)-4-Bz-ttda}](2-) at 37.0 +/- 0.1degrees and 20 MHz was 4.90 +/- 0.05 mM(-1) s(-1). The EPR transverse electronic relaxation rate and O-17-NMR transverse-relaxation time for the exchange lifetime of the coordinated H2O molecule (tau(M)), and H-2-NMR longitudinal-relaxation rate of the deuterated diamagnetic lanthanum complex for the rotational correlation time (tau(R)) were thoroughly investigated, and the results Were compared with those previously reported for the other lanthanide(III) complexes, The exchange lifetime (tau(M)) for [Gd{(S)-4-Bz-ttda}](2-) (2.3 +/- 13 ns) was significantly shorter than that of the [Gd(dtpa)(H2O)](2-) complex (dtpa = diethylenetriaminepentaacetic acid). The rotational correlation time tau(R) for [Gd{(S)-4-Bz-ttda}](2-) (70 +/- 6 ps) was slightly longer than that of the [Gd(dtpa)(H2O)](2-) Complex. The marked increase of relaxivity of [Gd{(S)-4-Bz-ttda}](2-) mainly resulted from its longer rotational time rather than from its fast water-exchange rate. The noncovalent interaction between human serum albumin (HSA) and the [Gd{(S)-4-Bz-ttda}](2-) complex containing the hydrophobic substituent was investigated by measuring the solvent proton relaxation rate of the aqueous solutions. The association constant (K-A) was less than 100 M-1. indicating a weaker interaction of [Gd{(S)-4-Bz-ttda}](2-) with HSA.

  DOI：

  10.1002/1522-2675(200204)85:4<1033::aid-hlca1033>3.0.co;2-n