IBNtxA | 1314879-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: IBNtxA
• 英文别名: 3-iodobenzoyl-6β-naltrexamine；3-iodobenzoylnaltrexamide；N-[(4R,4aS,7R,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]-3-iodobenzamide
• CAS: 1314879-44-1
• 化学式: C₂₇H₂₉IN₂O₄
• 分子量: 572.443
• InChiKey: FGAFDGWRFOJPRY-XGTKUTNFSA-N

物化性质

• 沸点：
  721.3±60.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  82
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  纳曲酮 在 ammonium acetate 、 sodium cyanoborohydride 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 IBNtxA
  参考文献：
  名称：

  Generation of novel radiolabeled opiates through site-selective iodination

  摘要：

  Tritiated opioid radioligands have proven valuable in exploring opioid binding sites. However, tritium has many limitations. Its low specific activity and limited counting efficiency makes it difficult to examine low abundant, high affinity sites and its disposal is problematic due to the need to use organic scintillants and its relatively long half-life. To overcome these issues, we have synthesized both unlabeled and carrier-free radioiodinated iodobenzoyl derivatives of 6 beta-naltrexamine ((125)I-BNtxA, 18), 6 beta-naloxamine ((125)I-BNalA, 19) and 6 beta-oxymorphamine ((125)I-BOxyA, 20) with specific activities of 2100 Ci/mmol. To optimize the utility of the radioligand, we designed a synthesis in which the radiolabel is incorporated in the last synthetic step, which required the selective iodination of the benzoyl moiety without incorporation into the phenolic A ring. Competition studies demonstrated high affinity of the unlabelled compounds for opioid receptors in transfected cell lines, as did the direct binding of the (125)I-ligands to the opioid receptors. The radioligand displayed very high sensitivity, enabling a marked reduction in tissue, as well as excellent signal/noise characteristics. These new (125)I-radioligands should prove valuable in future studies of opioid binding sites. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.008

文献信息

• Generation of novel radiolabeled opiates through site-selective iodination
  作者：Susruta Majumdar、Maxim Burgman、Nathan Haselton、Steven Grinnell、Julia Ocampo、Anna Rose Pasternak、Gavril W Pasternak

  DOI：10.1016/j.bmcl.2011.05.008

  日期：2011.7

  Tritiated opioid radioligands have proven valuable in exploring opioid binding sites. However, tritium has many limitations. Its low specific activity and limited counting efficiency makes it difficult to examine low abundant, high affinity sites and its disposal is problematic due to the need to use organic scintillants and its relatively long half-life. To overcome these issues, we have synthesized both unlabeled and carrier-free radioiodinated iodobenzoyl derivatives of 6 beta-naltrexamine ((125)I-BNtxA, 18), 6 beta-naloxamine ((125)I-BNalA, 19) and 6 beta-oxymorphamine ((125)I-BOxyA, 20) with specific activities of 2100 Ci/mmol. To optimize the utility of the radioligand, we designed a synthesis in which the radiolabel is incorporated in the last synthetic step, which required the selective iodination of the benzoyl moiety without incorporation into the phenolic A ring. Competition studies demonstrated high affinity of the unlabelled compounds for opioid receptors in transfected cell lines, as did the direct binding of the (125)I-ligands to the opioid receptors. The radioligand displayed very high sensitivity, enabling a marked reduction in tissue, as well as excellent signal/noise characteristics. These new (125)I-radioligands should prove valuable in future studies of opioid binding sites. (C) 2011 Elsevier Ltd. All rights reserved.