2-(3-[1-carboxy-5-[(5-[125I]iodo-pyridine-3-carbonyl)-amino]-pentyl]-ureido)-pentanedioic acid | 1093733-15-3

• 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-[125I]iodo-pyridine-3-carbonyl)-amino]-pentyl]-ureido)-pentanedioic acid
• 英文别名: (2S)-2-[[(1S)-1-carboxy-5-[(5-(125I)iodanylpyridine-3-carbonyl)amino]pentyl]carbamoylamino]pentanedioic acid
• CAS: 1093733-15-3
• 化学式: C₁₈H₂₃IN₄O₈
• 分子量: 548.403
• InChiKey: UMTBXFVMGMLOHV-IBQBXTBSSA-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 苯甲醚 、 三氟乙酸 作用下， 反应 0.08h， 生成 2-(3-[1-carboxy-5-[(5-[125I]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

• Radiohalogenated Prostate-Specific Membrane Antigen (PSMA)-Based Ureas as Imaging Agents for Prostate Cancer
  作者：Ying Chen、Catherine A. Foss、Youngjoo Byun、Sridhar Nimmagadda、Mrudula Pullambhatla、James J. Fox、Mark Castanares、Shawn E. Lupold、John W. Babich、Ronnie C. Mease、Martin G. Pomper

  DOI：10.1021/jm801055h

  日期：2008.12.25

  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.