3-(6-methoxy-2-naphthyl)-2-cyclopentenol | 960319-79-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(6-methoxy-2-naphthyl)-2-cyclopentenol
• 英文别名: 3-(6-Methoxynaphthalen-2-yl)cyclopent-2-en-1-ol
• CAS: 960319-79-3
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: GFUFFCWRBSDXAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(6-methoxy-2-naphthyl)-2-cyclopentenol 在 17β-hydroxysteroid-dehydrogenase type 10 β-烟酰胺腺嘌呤二核苷酸 作用下， 以 phosphate buffer 、 二甲基亚砜 为溶剂， 生成 3-(6-methoxy-2-naphthyl)-2-cyclopentenone
  参考文献：
  名称：

  Harnessing Functional Plasticity of Enzymes:  A Fluorogenic Probe for Imaging 17β-HSD10 Dehydrogenase, an Enzyme Involved in Alzheimer's and Parkinson's Diseases

  摘要：

  In this paper, we describe the development of a fluorogenic substrate for 17 beta-hydroxysteroid-dehydrogenase, type 10(17 beta-HSD10), which is a multifunctional metabolic enzyme fulfilling several metabolic roles beta-oxidation of fatty acids, catabolism of isoleucine, and metabolism of steroids). In recent years, it has emerged as an important stress and pathological marker in neurons and glial cells (expression downregulation in Parkinson's disease, up-regulation and association with beta-amyloid peptide in Alzheimer's disease). Through the iterative molecular design and chemical synthesis described herein, compound I was developed, which possesses all required properties for a selective optical reporter substrate: alcohol-ketone optical switching, the ability to function as a good enzyme substrate (expressed in kinetic parameters), cell permeability, and cell retention. Probe 1 provides a blue-to-green/yellow bright switch and enables non-invasive, real-time imaging of 17 beta-HSD10 in live human cells. The selectivity of reporter 1 was established by the quantitative correlation of metabolic activity to protein expression in human kidney cell line HEK-293T.

  DOI：

  10.1021/ja072601x
• 作为产物：
  描述：

  3-(6-methoxy-2-naphthyl)-2-cyclopentenone 在 cerium(III) chloride 甲醇 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以53%的产率得到3-(6-methoxy-2-naphthyl)-2-cyclopentenol
  参考文献：
  名称：

  Harnessing Functional Plasticity of Enzymes:  A Fluorogenic Probe for Imaging 17β-HSD10 Dehydrogenase, an Enzyme Involved in Alzheimer's and Parkinson's Diseases

  摘要：

  In this paper, we describe the development of a fluorogenic substrate for 17 beta-hydroxysteroid-dehydrogenase, type 10(17 beta-HSD10), which is a multifunctional metabolic enzyme fulfilling several metabolic roles beta-oxidation of fatty acids, catabolism of isoleucine, and metabolism of steroids). In recent years, it has emerged as an important stress and pathological marker in neurons and glial cells (expression downregulation in Parkinson's disease, up-regulation and association with beta-amyloid peptide in Alzheimer's disease). Through the iterative molecular design and chemical synthesis described herein, compound I was developed, which possesses all required properties for a selective optical reporter substrate: alcohol-ketone optical switching, the ability to function as a good enzyme substrate (expressed in kinetic parameters), cell permeability, and cell retention. Probe 1 provides a blue-to-green/yellow bright switch and enables non-invasive, real-time imaging of 17 beta-HSD10 in live human cells. The selectivity of reporter 1 was established by the quantitative correlation of metabolic activity to protein expression in human kidney cell line HEK-293T.

  DOI：

  10.1021/ja072601x

文献信息

• Harnessing Functional Plasticity of Enzymes:  A Fluorogenic Probe for Imaging 17β-HSD10 Dehydrogenase, an Enzyme Involved in Alzheimer's and Parkinson's Diseases
  作者：Mary K. Froemming、Dalibor Sames

  DOI：10.1021/ja072601x

  日期：2007.11.1

  In this paper, we describe the development of a fluorogenic substrate for 17 beta-hydroxysteroid-dehydrogenase, type 10(17 beta-HSD10), which is a multifunctional metabolic enzyme fulfilling several metabolic roles beta-oxidation of fatty acids, catabolism of isoleucine, and metabolism of steroids). In recent years, it has emerged as an important stress and pathological marker in neurons and glial cells (expression downregulation in Parkinson's disease, up-regulation and association with beta-amyloid peptide in Alzheimer's disease). Through the iterative molecular design and chemical synthesis described herein, compound I was developed, which possesses all required properties for a selective optical reporter substrate: alcohol-ketone optical switching, the ability to function as a good enzyme substrate (expressed in kinetic parameters), cell permeability, and cell retention. Probe 1 provides a blue-to-green/yellow bright switch and enables non-invasive, real-time imaging of 17 beta-HSD10 in live human cells. The selectivity of reporter 1 was established by the quantitative correlation of metabolic activity to protein expression in human kidney cell line HEK-293T.