2,2'-[4,10-bis(2-{[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]amino}-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,7-diyl]diacetic acid | 1178937-49-9

• 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: 2,2'-[4,10-bis(2-{[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]amino}-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,7-diyl]diacetic acid
• 英文别名: 4,10-bis{[2-(2-methyl-5-nitroimidazol-1-yl)ethylcarbamoyl]methyl}-1,4,7,10-tetraazacyclododecane-1,7-diacetic acid；2-[7-(Carboxymethyl)-4,10-bis[2-[2-(2-methyl-5-nitroimidazol-1-yl)ethylamino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid；2-[7-(carboxymethyl)-4,10-bis[2-[2-(2-methyl-5-nitroimidazol-1-yl)ethylamino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid
• CAS: 1178937-49-9
• 化学式: C₂₈H₄₄N₁₂O₁₀
• 分子量: 708.732
• InChiKey: WQVGNUJXASZGPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  273
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  bis(tert-butyl) 2,2'-[4,10-bis(2-{[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]amino}-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,7-diyl]diacetate 在 盐酸 、 水 作用下， 反应 2.0h， 以95.4%的产率得到2,2'-[4,10-bis(2-{[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]amino}-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,7-diyl]diacetic acid
  参考文献：
  名称：

  Design of Ga–DOTA-based bifunctional radiopharmaceuticals: Two functional moieties can be conjugated to radiogallium–DOTA without reducing the complex stability

  摘要：

  From the X-ray crystal structures of Ga-DOTA chelates, we were able to deduce that two free carboxylate groups of the radiogallium-DOTA complex may be utilized for coupling to functional moieties that recognize molecular targets for in vivo imaging without reducing the radiogallium-complex stability. Thus, we designed 2,2'-[4,10-bis(2-{[2-(2-methyl-5-nitro-1H-imidazol-1-yl) ethyl]amino}-2-oxoethyl)1,4,7,10-tetraazacyclododecane-1,7-diyl]diacetic acid (DOTA-MN2) (7), employing a metronidazole moiety as the recognition site of hypoxic lesions, based on the drug design concept of bifunctional radiopharmaceuticals. Coupling of DOTA-bis(tert-butyl) ester 5 with 1-(2-aminoethyl)-2-methyl-5-nitroimidazole dihydrochloride, followed by deprotection, afforded the required 7 (DOTA-MN2). Ga-67-labeling was carried out by reaction of DOTA-MN2 with Ga-67-citrate. When Ga-67-DOTA-MN2 was incubated in phosphate-buffered saline or mouse plasma, no measurable decomposition occurred over a 24-h period. In biodistribution experiments in NFSa tumor-bearing mice, Ga-67-DOTA-MN2 displayed not only a significant tumor uptake, but also rapid blood clearance and low accumulations in nontarget tissues, resulting in high target-to-nontarget ratios of radioactivity. These results indicate the potential benefits of the drug design of Ga-67-DOTA-MN2. The present findings provide helpful information for the development of radiogallium-labeled radiopharmaceuticals for SPECT and PET studies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.041

文献信息

• DIAGNOSTIC AGENT FOR INFECTIOUS DISEASES
  申请人：Sakurai Kazuhisa

  公开号：US20120219500A1

  公开（公告）日：2012-08-30

  A diagnostic agent for infectious diseases which is capable of distinguishing among different kinds of bacterial species and which allows simple and non-invasive measurement and/or imaging in a short period of time is provided; and a screening method for a therapeutic agent for infectious diseases caused by microorganisms are provided. A diagnostic agent for infectious diseases caused by nitroimidazole susceptible microorganisms, containing an imidazole derivative or a fused imidazole derivative having at least one nitro group on an imidazole ring, or a labeled form thereof as an active ingredient is provided.

  提供了一种针对传染病的诊断试剂，能够区分不同种类的细菌，并允许在短时间内进行简单、非侵入性的测量和/或成像；同时提供了一种筛选治疗由微生物引起的传染病的方法。提供了一种针对对硝基咪唑敏感微生物引起的传染病的诊断试剂，其包含一种咪唑衍生物或至少在咪唑环上具有一个硝基基团的融合咪唑衍生物，或其标记形式作为活性成分。