2-chloro-N-(phenanthridin-6-ylmethyl)acetamide | 1400866-15-0

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-chloro-N-(phenanthridin-6-ylmethyl)acetamide
• 英文别名: 2-Chloro-N-(phenanthridin-6-ylmethyl)acetamide
• CAS: 1400866-15-0
• 化学式: C₁₆H₁₃ClN₂O
• 分子量: 284.745
• InChiKey: GWSFWQVGILXLSE-UHFFFAOYSA-N

物化性质

• 沸点：
  547.3±40.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险类别：
  6.1
• 危险性防范说明：
  P201,P202,P261,P264,P270,P271,P280,P302+P352,P304+P340,P308+P313,P310,P330,P361,P403+P233,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301,H311,H331,H341
• 包装等级：
  III

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(phenanthridin-6-ylmethyl)acetamide 在 caesium carbonate 、 三乙胺 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 38.0h， 生成 di-tert-butyl 2,2′-(4-(2-((2-((tert-butoxycarbonyl)-amino)ethyl)amino)-2-oxoethyl)-10-(2-oxo-2-((phenanthridin-6-ylmethyl)amino)ethyl)-1,4,7,10-tetraazacyclododecane-1,7-diyl)diacetate
  参考文献：
  名称：

  Turning an Aptamer into a Light-Switch Probe with a Single Bioconjugation

  摘要：

  We describe a method for transforming a structure-switching aptamer into a luminescent light-switch probe via a single conjugation. The methodology is demonstrated using a known aptamer for Hg2+ as a case study. This approach utilizes a lanthanide-based metallointercalator, Eu-DOTA-Phen, whose luminescence is quenched almost entirely and selectively by purines, but not at all by pyrimidines. This complex, therefore, does not luminesce while intercalated in dsDNA, but it is bright red when conjugated to a ssDNA that is terminated by several pyrimidines. In its design, the light-switch probe incorporates a structure-switching aptamer partially hybridized to its complementary strand. The lanthanide complex is conjugated to either strand via a stable amide bond. Binding of the analyte by the structure-switching aptamer releases the complementary strand. This release precludes intercalation of the intercalator in dsDNA, which switches on its luminescence. The resulting probe turns on 21-fold upon binding to its analyte. Moreover, the structure switching aptamer is highly selective, and the long luminescence lifetime of the probe readily enables time-gating experiments for removal of the background autofluorescence of the sample.

  DOI：

  10.1021/bc5003899
• 作为产物：
  描述：

  2-硝基联苯 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 lithium hydroxide monohydrate 、 10% Pd/C 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 150.0 ℃ 、500.01 kPa 条件下， 反应 25.91h， 生成 2-chloro-N-(phenanthridin-6-ylmethyl)acetamide
  参考文献：
  名称：

  A Selective Luminescent Probe for the Direct Time-Gated Detection of Adenosine Triphosphate

  摘要：

  A molecular probe for the luminescent detection of adenosine nucleotides is presented. The probe, Tb-DOTAm-Phen, readily distinguishes among the three adenosine nucleotides in buffered aqueous conditions at neutral pH, a requirement for the direct monitoring of enzymatic reactions converting adenosine triphosphate (ATP) to adenosine diphosphate or adenosine monophosphate. The probe is most efficient under millimolar concentrations of ATP which are relevant to intracellular conditions. Moreover, the long luminescence lifetime of the probe readily enables time-gating experiments.

  DOI：

  10.1021/ja304373u

文献信息

• The basis for the molecular recognition and the selective time-gated luminescence detection of ATP and GTP by a lanthanide complex
  作者：Evan A. Weitz、Jennifer Y. Chang、Adam H. Rosenfield、Elizabeth A. Morrow、Valérie C. Pierre

  DOI：10.1039/c3sc51583d

  日期：——

  phosphates of ATP and GTP, as evidenced by the lack of any selectivity for ATP/ADP/AMP or GTP/GDP/GMP by the neutral europium complex. Both the selective terbium complex and its non-responsive europium analog can be used concomitantly in the same solution as neither probe affects the response of the other. Simultaneous use of the two chemosensors enables more accurate ratiometric detection of ATP to ADP or GTP

  提出了两种用于检测核苷酸的分子探针。带正电荷的[Tb-DOTAm-Phen] 3+仅对嘌呤核苷酸有反应，并选择性检测GTP和ATP分别超过GDP / GMP和ADP / AMP。另一方面，中性的Eu-DOTA-Phen复合物对嘌呤比嘧啶具有选择性，但不能区分三磷酸，二磷酸和一磷酸核苷酸。两种探针均具有长的发光寿命，可轻松进行时间门控实验并完全去除任何自发荧光背景。Stern-Volmer常数随温度的降低表明淬灭的静态机制与堆积的菲啶-嘌呤复合物的形成相一致。探针相对于嘧啶对嘌呤的选择性是由于更高延伸的嘌呤对菲啶发色团的更高的结合亲和力和淬灭能力。带正电荷的complex配合物对二磷酸和单磷酸核苷酸的三价选择性是由于与ATP和GTP的带负电荷的磷酸盐弱的静电相互作用，这证明了对ATP / ADP /缺乏选择性中性complex络合物的AMP或GTP / GDP / GMP。选择性b络合物及其
• LUMINESCENT PROBES HAVING A PHENANTHRIDINYL ANTENNA, AND METHODS OF USE
  申请人：Pierre Valerie Christine

  公开号：US20140080163A1

  公开（公告）日：2014-03-20

  A molecular probe for the luminescent detection of nucleotides (e.g., adenosine nucleotides) is presented. In certain embodiments, the probe can readily distinguish between the three adenosine nucleotides in buffered aqueous conditions at neutral pH, a need for the direct monitoring of enzymatic reactions converting ATP to ADP or AMP. The probe is most efficient under millimolar concentrations of ATP, which are relevant to intracellular conditions. In preferred embodiments, the long luminescence lifetime of the probe readily enables time-gating experiments.

  本文介绍了一种用于发光检测核苷酸（例如腺苷酸）的分子探针。在某些实施例中，该探针可以在缓冲的水溶液中，在中性pH条件下轻松区分三种腺苷酸，这是直接监测将ATP转化为ADP或AMP的酶反应的需要。该探针在毫摩尔浓度的ATP下最有效，这与细胞内条件相关。在首选实施例中，探针的长发光寿命可轻松实现时间分段实验。
• Luminescent probes having a phenanthridinyl antenna, and methods of use
  申请人：REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：US09194802B2

  公开（公告）日：2015-11-24

  A molecular probe for the luminescent detection of nucleotides (e.g., adenosine nucleotides) is presented. In certain embodiments, the probe can readily distinguish between the three adenosine nucleotides in buffered aqueous conditions at neutral pH, a need for the direct monitoring of enzymatic reactions converting ATP to ADP or AMP. The probe is most efficient under millimolar concentrations of ATP, which are relevant to intracellular conditions. In preferred embodiments, the long luminescence lifetime of the probe readily enables time-gating experiments.

  这是一种用于发光检测核苷酸（例如腺苷酸）的分子探针。在某些实施例中，该探针可以在缓冲的水溶液中，在中性pH下轻松区分三种腺苷酸，这是直接监测将ATP转化为ADP或AMP的酶反应的需要。该探针在毫摩尔浓度的ATP下最有效，这与细胞内条件相关。在优选实施例中，探针的长发光寿命可以轻松地进行时间门控实验。
• US9194802B2
  申请人：——

  公开号：US9194802B2

  公开（公告）日：2015-11-24
• A Selective Luminescent Probe for the Direct Time-Gated Detection of Adenosine Triphosphate
  作者：Evan A. Weitz、Jennifer Y. Chang、Adam H. Rosenfield、Valerie C. Pierre

  DOI：10.1021/ja304373u

  日期：2012.10.3

  A molecular probe for the luminescent detection of adenosine nucleotides is presented. The probe, Tb-DOTAm-Phen, readily distinguishes among the three adenosine nucleotides in buffered aqueous conditions at neutral pH, a requirement for the direct monitoring of enzymatic reactions converting adenosine triphosphate (ATP) to adenosine diphosphate or adenosine monophosphate. The probe is most efficient under millimolar concentrations of ATP which are relevant to intracellular conditions. Moreover, the long luminescence lifetime of the probe readily enables time-gating experiments.