N-[3-[(2S,5S,17S)-5,17-二[3-(乙酰基-羟基氨基)丙基]-3,6,9,12,15,18-六氧代-1,4,7,10,13,16-六氮杂十八碳-2-基]丙基]-N-羟基乙酰胺 | 68802-67-5

• 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
• 中文名称: N-[3-[(2S,5S,17S)-5,17-二[3-(乙酰基-羟基氨基)丙基]-3,6,9,12,15,18-六氧代-1,4,7,10,13,16-六氮杂十八碳-2-基]丙基]-N-羟基乙酰胺
• 英文名称: desferriferrichrome
• 英文别名: deferriferrichrome；desferrichrome；ferrichrome；FER；N-Desferriferrichrome；N-[3-[(2S,5S,8S)-5,8-bis[3-[acetyl(hydroxy)amino]propyl]-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexazacyclooctadec-2-yl]propyl]-N-hydroxyacetamide
• CAS: 68802-67-5；34787-28-5
• 化学式: C₂₇H₄₅N₉O₁₂
• 分子量: 687.707
• InChiKey: ZFDAUYPBCXMSBF-ACRUOGEOSA-N

物化性质

• 熔点：
  197-203°C
• 溶解度：
  可溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  296
• 氢给体数：
  9
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  zirconium(IV) acetylacetonate 、 N-[3-[(2S,5S,17S)-5,17-二[3-(乙酰基-羟基氨基)丙基]-3,6,9,12,15,18-六氧代-1,4,7,10,13,16-六氮杂十八碳-2-基]丙基]-N-羟基乙酰胺 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到
  参考文献：
  名称：

  Multifunctional Desferrichrome Analogues as Versatile ⁸⁹Zr(IV) Chelators for ImmunoPET Probe Development

  摘要：

  New bifunctional hexa- and octadentate analogues of the hydroxamate-containing siderophore desferri-chrome (DFC) have been synthesized and evaluated as Zr-89-chelating agents for immunoPET applications. The in vitro and in vivo inertness of these new ligands, Orn3-hx (hexadentate) and Orn-4hx derivatives (octadentate), was compared to the gold standard hexadentate, hydroxamate-containing chelator for Zr-89 desferrioxamine (DFO). Density functional theory was employed to model the geometries of the resulting Zr(IV) complexes and to predict their relative stabilities as follows: Zr(Orn4-hx) > Zr(DFC) > Zr(Orn3-hx). Transchelation challenge experiments of the corresponding radiochemical complexes with excess ethylenediaminetetraacetate (EDTA) indicated complex stability in accordance with DFT calculations. Radiolabeling of these ligands with (89)Zt was quantitative (0.25 mu mol of ligand, pH 7.4, room temperature, 20 min). For antibody conjugation, the isothiocyarrate (NOS) functional group was introduced to the N terminus of Orn3-hx and Orn-4hx. An additional trifunctional derivative that bears a silicon-rhodamine fluorophore on the C-terminus and NCS on the N terminus was also furnished. As proof of concept, all NCS derivatives were conjugated to the HER2-targeting antibody, trastuzumab. Radiolabeling of immunoconjngates with Zr-89 was accomplished with radiochemical yields of 16 +/- 2% to 95 +/- 2%. These constructs were administered to naive mice (male, C57BL/6J, n = 4) to assess in vivo inertness, which is inversely correlated with uptake, of Zr-89 in bone, after 96 h circulation time. We found, bone uptake to range from 7.0 +/- 2.2 to 10.7 +/- 1.3% ID/g, values that compare well to the corresponding DFO conjugate (7.1 +/- 0.8% ID/g). In conclusion, we have rationally designed linear, bifunctional and trifunctional desferrichrome analogues suitable for the mild and inert radiolabeling of antibodies with the radionuclide Zr-89.

  DOI：

  10.1021/acs.molpharmaceut.7b00343
• 作为产物：
  描述：

  Boc-甘氨酰甘氨酸 在 palladium on activated charcoal N-甲基吗啉 、 吡啶 、 sodium hydroxide 、 N-羟基丁二酰亚胺 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 119.25h， 生成 N-[3-[(2S,5S,17S)-5,17-二[3-(乙酰基-羟基氨基)丙基]-3,6,9,12,15,18-六氧代-1,4,7,10,13,16-六氮杂十八碳-2-基]丙基]-N-羟基乙酰胺
  参考文献：
  名称：

  N-Hydroxy amides. 7. Synthesis and properties of linear and cyclic hexapeptides containing three N5-acetyl-N5-hydroxy-L-ornithine residues as models for ferrichrome

  摘要：

  DOI：

  10.1021/jo00261a019

文献信息

• Synthesis and application of an Nδ-acetyl-Nδ-hydroxyornithine analog: Identification of novel metal complexes of deferriferrichrysin
  作者：Kazuya Kobayashi、Shinya Oishi、Yuka Kobayashi、Hiroaki Ohno、Hiroko Tsutsumi、Yoji Hata、Nobutaka Fujii

  DOI：10.1016/j.bmc.2012.02.033

  日期：2012.4

  Synthesis of Fmoc-protected Nδ-acetyl-Nδ-(tert-butoxy)-l-ornithine has revealed it to be a metal-chelating amino-acid precursor. This protected amino acid was compatible with the preparation of ferrichrome peptides by standard Fmoc-based solid-phase peptide synthesis. Evaluation of deferriferrichrysin for metal ion chelation revealed that zirconium(IV) and titanium(IV) formed complexes with deferriferrichrysin

  的合成Fmoc-保护Ñ δ -乙酰基- ñ δ - （叔丁氧基） -升鸟氨酸已表明它是金属螯合氨基酸的前体。通过标准的基于Fmoc的固相肽合成，这种受保护的氨基酸与铁铬肽的制备兼容。对去铁弗里希氏菌素进行金属离子螯合的评价表明，锆（IV）和钛（IV）与去铁弗里希素形成了配合物。
• METHOD OF VISCOSITY REDUCTION IN THE PRESENCE OF FULLY COORDINATED COMPOUNDS
  申请人：SCHLUMBERGER TECHNOLOGY CORPORATION

  公开号：US20150175880A1

  公开（公告）日：2015-06-25

  Methods for reducing a viscosity of a viscosified fluid include reacting, such as by depolymerizing and/or decomposing, a polymeric material of the viscosified fluid with a breaking agent including a fully coordinated transition metal compound, such as a strongly complexed fully-coordinated transition metal compound. The methods of treating the subterranean are provided that include reacting, such as by depolymerizing and/or decomposing, a polymeric material of a viscosified treatment fluid with a fully coordinated transition metal compound, such as a strongly complexed fully-coordinated transition metal compound, to facilitate breaking of the viscosified treatment fluid after the fracturing or treatment is finished.

  降低高粘度粘化流体的方法包括使用断裂剂，如含有完全配位的过渡金属化合物，例如强配位的完全配位过渡金属化合物，与粘化流体的聚合物材料反应，例如进行去聚合和/或分解。提供了处理地下岩石层的方法，包括使用完全配位的过渡金属化合物，例如强配位的完全配位过渡金属化合物，与粘化处理流体的聚合物材料反应，例如进行去聚合和/或分解，以便在压裂或处理完成后使粘化处理流体破裂。
• AKIYAMA, MASAYASU;KATOH, AKIRA;MUTOH, TSUTOMU, J. ORG. CHEM., 53,(1988) N6, C. 6089-6094
  作者：AKIYAMA, MASAYASU、KATOH, AKIRA、MUTOH, TSUTOMU

  DOI：——

  日期：——