[125I]-2-(3-{1-carboxy-5-[3-(4-iodophenyl)-ureido]-pentyl}-ureido)-pentanedioic acid | 949575-25-1

• 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: [125I]-2-(3-{1-carboxy-5-[3-(4-iodophenyl)-ureido]-pentyl}-ureido)-pentanedioic acid
• 英文别名: [125I]-MIP-1095；[¹²³I]MIP-1095；(123)I-(S)-2-(3-((S)-1-carboxy-5-(3-(4-iodophenyl)ureido)pentyl)ureido)pentanedioic acid；(123I)-(S)-2-(3-((S)-1-Carboxy-5-(3-(4-iodophenyl)ureido)pentyl)ureido)pentanedioic acid；(2S)-2-[[(1S)-1-carboxy-5-[(4-(123I)iodanylphenyl)carbamoylamino]pentyl]carbamoylamino]pentanedioic acid
• CAS: 949575-25-1
• 化学式: C₁₉H₂₅IN₄O₈
• 分子量: 560.429
• InChiKey: LFEGKCKGGNXWDV-NKNRFTOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  194
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  ⁽¹²³⁾I-(S)-2-(3-((S)-1-carboxy-5-(3-(4-iodophenyl)ureido)-pentyl)ureido)pentanedioic acid tri-tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 [125I]-2-(3-{1-carboxy-5-[3-(4-iodophenyl)-ureido]-pentyl}-ureido)-pentanedioic acid
  参考文献：
  名称：

  A Series of Halogenated Heterodimeric Inhibitors of Prostate Specific Membrane Antigen (PSMA) as Radiolabeled Probes for Targeting Prostate Cancer

  摘要：

  Prostate specific membrane antigen (PSMA) is a validated molecular marker for prostate cancer. A series of glutamate-urea (Glu-urea-X) heterodimeric inhibitors of PSMA were designed and synthesized where X = epsilon-N-(o-I, m-I, p-I, p-Br, o-C1, m-C1, p-C1, p-F, H)-benzyl-Lys and epsilon-(p-I, p-Br, p-C1, p-F, H)-phenylureido-Lys. The affinities for PSMA were determined by screening in a competitive binding assay. PSMA binding of the benzyllysine series was significantly affected by the nature of the halogen substituent (IC50 values, Cl < I = Br << F = H) and the ring position of the halogen atom (IC50 values, p-I < o-I << m-I). The halogen atom had little affect oil the binding affinity in the para substituted phenylureido-Lys series. Two lead iodine compounds were radiolabeled with I-123 and I-131 and demonstrated specific PSMA binding on human prostate cancer cells, warranting evaluation as radioligands for the detection, staging, and monitoring of prostate cancer.

  DOI：

  10.1021/jm800994j

文献信息

• [EN] PROCESS FOR PRODUCTION OF HETERODIMERS OF GLUTAMIC ACID<br/>[FR] PROCÉDÉ DE PRODUCTION D'HÉTÉRODIMÈRES D'ACIDE GLUTAMIQUE
  申请人：MOLECULAR INSIGHT PHARM INC

  公开号：WO2010147965A3

  公开（公告）日：2011-07-28
• PROCESS FOR PRODUCTION OF HETERODIMERS OF GLUTAMIC ACID
  申请人：Babich John W.

  公开号：US20110008253A1

  公开（公告）日：2011-01-13

  A manufacturing process for the preparation of radiolabeled compounds of formula (I) includes reacting compounds of formula (II) with a source of readionuclide of a halogen in the presence of an oxidant under acidic condition, wherein: *I is 123 I, 124 I, 125 I or 131 I; R is lower alkyl, optionally substituted with one or more fluorine atoms; Q is C(O), O, NR′, S, S(O) 2 , C(O) 2 , (CH 2 ) p ; Y is C(O), O, NR′, S, S(O) 2 , C(O) 2 , (CH 2 ) p ; R′ is H, C(O), S(O) 2 , C(O) 2 ; Z is H, C 1 -C 4 alkyl, benzyl, substituted benzyl or trialkylsilyl; m is 0, 1, 2, 3, 4 or 5; n is 0, 1, 2, 3, 4, 5 or 6; and p is 0, 1, 2, 3, 4, 5 or 6.
• US8465725B2
  申请人：——

  公开号：US8465725B2

  公开（公告）日：2013-06-18
• A Series of Halogenated Heterodimeric Inhibitors of Prostate Specific Membrane Antigen (PSMA) as Radiolabeled Probes for Targeting Prostate Cancer
  作者：K. P. Maresca、S. M. Hillier、F. J. Femia、D. Keith、C. Barone、J. L. Joyal、C. N. Zimmerman、A. P. Kozikowski、J. A. Barrett、W. C. Eckelman、J. W. Babich

  DOI：10.1021/jm800994j

  日期：2009.1.22

  Prostate specific membrane antigen (PSMA) is a validated molecular marker for prostate cancer. A series of glutamate-urea (Glu-urea-X) heterodimeric inhibitors of PSMA were designed and synthesized where X = epsilon-N-(o-I, m-I, p-I, p-Br, o-C1, m-C1, p-C1, p-F, H)-benzyl-Lys and epsilon-(p-I, p-Br, p-C1, p-F, H)-phenylureido-Lys. The affinities for PSMA were determined by screening in a competitive binding assay. PSMA binding of the benzyllysine series was significantly affected by the nature of the halogen substituent (IC50 values, Cl < I = Br << F = H) and the ring position of the halogen atom (IC50 values, p-I < o-I << m-I). The halogen atom had little affect oil the binding affinity in the para substituted phenylureido-Lys series. Two lead iodine compounds were radiolabeled with I-123 and I-131 and demonstrated specific PSMA binding on human prostate cancer cells, warranting evaluation as radioligands for the detection, staging, and monitoring of prostate cancer.