2-(3-[1-carboxy-5-[(5-iodo-pyridine-3-carbonyl)-amino]-pentyl]-ureido)-pentanedioic acid | 1093733-12-0

• 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-(3-[1-carboxy-5-[(5-iodo-pyridine-3-carbonyl)-amino]-pentyl]-ureido)-pentanedioic acid
• 英文别名: (S)-2-(3-((S)-1-carboxy-5-(3-iodonicotinamido)pentyl)ureido)pentanedioic acid；(2S)-2-[[(1S)-1-carboxy-5-[(5-iodopyridine-3-carbonyl)amino]pentyl]carbamoylamino]pentanedioic acid
• CAS: 1093733-12-0
• 化学式: C₁₈H₂₃IN₄O₈
• 分子量: 550.307
• InChiKey: UMTBXFVMGMLOHV-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  195
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以0.008 g的产率得到2-(3-[1-carboxy-5-[(5-iodo-pyridine-3-carbonyl)-amino]-pentyl]-ureido)-pentanedioic acid
  参考文献：
  名称：

  Radiohalogenated Prostate-Specific Membrane Antigen (PSMA)-Based Ureas as Imaging Agents for Prostate Cancer

  摘要：

  To extend our development of new imaging agents targeting the prostate-specific membrane antigen (PSMA), we have used the versatile intermediate 2-[3-(5-amino-1-carboxy-pentyl)-ureido]-pentanedioic acid (Lys-C(O)-Glu), which allows ready incorporation of radiohalogens for single photon emission computed tomography (SPECT) and positron emission tomography (PET). We prepared 2-[3-[1-carboxy-5-(4-[I-125]iodobenzoylamino)-pentyl]-ureido]-pentanedioic acid ([I-125]3), 2-[3-[1-carboxy-5-(4-[F-18]fluoro-benzoylamino)-pentyl-ureido]-pentanedioic acid ([F-18]6), and 2-(3-[1-carboxy-5-[(5-[I-125]iodo-pyridine-3-carbonyl)-amino]-pentyl ureido)-pentanedioic acid ([I-125]8) in 65-80% (nondecay-corrected), 30-35% (decay corrected), and 59-75% (nondecay-corrected) radiochemical yields. Compound [I-125]3 demonstrated 8.8 +/- 4.7% injected close per gram (%ID/g) within PSMA(+) PC-3 PIP tumor at 30 min postinjection, which persisted, with clear delineation of the tumor by SPECT. similar tumor uptake values at early time points were demonstrated for [F-18]6 (using PET) and [I-125]8. Because of the many radiohalogenated moieties that call be attached via the e amino group, the intermediate Lys-C(O)-Glu is an attractive template upon which to develop new imaging agents for prostate cancer.

  DOI：

  10.1021/jm801055h

文献信息

• Scaffolds and multifunctional intermediates for imaging PSMA and cancer therapy
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：US10736974B2

  公开（公告）日：2020-08-11

  Carbamate and beta-amino acid urea-based scaffolds that have high binding affinity to PSMA are disclosed. These scaffolds can be radiolabeled and used for imaging cells and tumors that express PSMA or for cancer radiotherapy. These compounds also can comprise a fluorescent dye and be used for imaging cells and tumors that express PSMA or for photodynamic therapy.

  本发明公开了与 PSMA 具有高结合亲和力的氨基甲酸酯和β-氨基酸脲基支架。这些支架可进行放射性标记，用于表达 PSMA 的细胞和肿瘤成像或癌症放射治疗。这些化合物还可以包含荧光染料，用于表达 PSMA 的细胞和肿瘤成像或光动力疗法。
• NEW SCAFFOLDS AND MULTIFUNCTIONAL INTERMEDIATES FOR IMAGING PSMA AND CANCER THERAPY
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：US20170333576A1

  公开（公告）日：2017-11-23

  Carbamate and beta-amino acid urea-based scaffolds that have high binding affinity to PSMA are disclosed. These scaffolds can be radiolabeled and used for imaging cells and tumors that express PSMA or for cancer radiotherapy. These compounds also can comprise a fluorescent dye and be used for imaging cells and tumors that express PSMA or for photodynamic therapy.
• SCAFFOLDS AND MULTIFUNCTIONAL INTERMEDIATES FOR IMAGING PSMA AND CANCER THERAPY
  申请人：The Johns Hopkins University

  公开号：US20200360542A1

  公开（公告）日：2020-11-19

  Carbamate and beta-amino acid urea-based scaffolds that have high binding affinity to PSMA are disclosed. These scaffolds can be radiolabeled and used for imaging cells and tumors that express PSMA or for cancer radiotherapy. These compounds also can comprise a fluorescent dye and be used for imaging cells and tumors that express PSMA or for photodynamic therapy.