光黄素-3-乙酸 | 20227-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 中文名称: 光黄素-3-乙酸
• 英文名称: (7,8,10-trimethyl-2,4-dioxo-4,10-dihydro-2H-benzo[g]pteridin-3-yl)acetic acid
• 英文别名: 3-carboxymethyllumiflavin；lumiflavin-3-acetic acid；(7,8,10-trimethyl-2,4-dioxo-4,10-dihydro-2H-benzo[g]pteridin-3-yl)-acetic acid；PX088992；flavin；Lumiflavin-3-essigsaeure；2-(7,8,10-Trimethyl-2,4-dioxobenzo[g]pteridin-3-yl)acetic acid
• CAS: 20227-26-3
• 化学式: C₁₅H₁₄N₄O₄
• 分子量: 314.301
• InChiKey: GJSCQGXLPDWOMG-UHFFFAOYSA-N

物化性质

• 熔点：
  >270°C (dec.)
• 沸点：
  562.1±60.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  光黄素-3-乙酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 2-(N-(2-((t-butoxy)carbonylamino)ethyl))-2-(5,7,8-trimethyl-1,3-dioxo(2,5-dihydro-2,4-diazaphenazin-2-yl)acetylamino)acetic acid
  参考文献：
  名称：

  Synthesis and characterization of flavin-tethered peptide nucleic acid

  摘要：

  We synthesized flavin-containing PNA. monomer unit 5 from lumiflavin and prepared PNAs containing a flavin moiety (FPNA) by the standard tBoc chemistry. Each PNA oligomer was purified by reversed-phase HPLC and characterized by MALDI-TOF MS and UV spectra. Thermodynamic analyses indicated that the PNA oligomer containing a flavin moiety near the amino terminal considerably stabilized the PNA-DNA hybrids. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00228-3
• 作为产物：
  描述：

  光黄素-3-乙酸乙酯 以 盐酸 为溶剂， 反应 6.0h， 以99%的产率得到光黄素-3-乙酸
  参考文献：
  名称：

  Synthesis and characterization of flavin-tethered peptide nucleic acid

  摘要：

  We synthesized flavin-containing PNA. monomer unit 5 from lumiflavin and prepared PNAs containing a flavin moiety (FPNA) by the standard tBoc chemistry. Each PNA oligomer was purified by reversed-phase HPLC and characterized by MALDI-TOF MS and UV spectra. Thermodynamic analyses indicated that the PNA oligomer containing a flavin moiety near the amino terminal considerably stabilized the PNA-DNA hybrids. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00228-3
• 作为试剂：
  描述：

  乙醇 、 4-(萘-2-基)-2-氧代丁酸 在 光黄素-3-乙酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 二氧化碳 、 乙基3-(2-萘基)丙酸酯
  参考文献：
  名称：

  A novel enzyme mimic for thiazolium-catalyzed α-ketoacid decarboxylation

  摘要：

  DOI：

  10.1016/s0040-4039(00)82313-8

文献信息

• Effect of stereochemistry on the catalytic activity of flavopeptides
  作者：Yukihiro Arakawa、Nao Takechi、Ken Yamanomoto、Keiji Minagawa、Yasushi Imada

  DOI：10.1016/j.tetlet.2021.153107

  日期：2021.6

  3-FlC2-l-Pro-l-Tyr-l-Asp-Ado-NH-PS (Fl-PepLLL), and its diastereomers including Fl-PepDDL, Fl-PepLDL, and Fl-PepDLL were synthesized to investigate the correlation between their catalytic activity and stereochemistry. The results and related computations showed the importance of intramolecular hydrogen bonds involving the Asp residue in their 4a-hydroperoxy forms for the catalysis.

  原始flavopeptide催化剂，3- FlC2-升-Pro-升-Tyr-升-Asp-ADO-NH-PS（FL-PEP LLL），和它的非对映体，包括FL-PEP DDL，FL-PEP LDL，和FL-合成Pep DLL以研究其催化活性与立体化学之间的相关性。结果和相关计算表明，涉及 4a-氢过氧形式的 Asp 残基的分子内氢键对催化的重要性。
• PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING CANCER CONTAINING PLK1 INHIBITOR AS ACTIVE INGREDIENT
  申请人：NATIONAL CANCER CENTER

  公开号：US20220033405A1

  公开（公告）日：2022-02-03

  The present invention relates to a pharmaceutical composition for preventing, treating or alleviating cancer, containing a PLK1 inhibitor as an active ingredient, and a compound according to the present invention selectively binds to PBD of PLK1, thereby having advantages of high selectivity and binding affinity for PLK1 and low toxicity. Therefore, a PLK inhibitor compound according to the present invention can be effectively used as an anticancer agent by inhibiting the growth of various cancer cells, and can be expected to exhibit synergistic effects with existing developed anticancer agents through co-administration, in addition to individual administration thereof.

  本发明涉及一种用于预防、治疗或缓解癌症的药物组合物，包含PLK1抑制剂作为活性成分。本发明的化合物选择性地结合到PLK1的PBD上，因此具有高选择性和结合亲和力，且毒性较低的优点。因此，根据本发明的PLK抑制剂化合物可以通过抑制各种癌细胞的生长有效地用作抗癌剂，并且可以通过联合使用与现有开发的抗癌剂表现出协同效应，除了单独使用之外。
• Photoinduced Release of Fluorescent Probe in the Presence of Target DNA: Synergetic Effect of Two Types of Oligonucleotides with Indolequinone–Coumarin Conjugate and Flavin Photosensitizer
  作者：Kazuhito Tanabe、Yukihiro Tachi、Arimichi Okazaki、Sei-ichi Nishimoto

  DOI：10.1246/cl.2006.938

  日期：2006.8

  We have synthesized and evaluated two types of functionalized oligodeoxynucleotides (ODNs) that can release a fluorescent coumarin probe via co-hybridization with a target DNA base sequence and subsequent photoirradiation. Photoirradiation of flavin-bearing ODN in the presence of a counterpart ODN with indolequinone–coumarin conjugate and a target complementary DNA strand gave rise to the efficient release of coumarin with a multiple turnover as a result of intermolecular flavin-photosensitized reduction of indolequinone–coumarin conjugate, while the release of coumarin was considerably suppressed in the absence of the target DNA. Concomitant with this photoreaction, we could observe intense fluorescence emission from the sample solution photoirradiated with the target DNA, but weak fluorescence from a control solution without the target DNA.

  我们合成并评估了两种功能化寡去氧核苷酸（ODN），它们可以通过与目标 DNA 碱基序列共杂交和随后的光照射释放出荧光香豆素探针。在含有吲哚醌-香豆素共轭物的对应 ODN 和目标互补 DNA 链存在的情况下，对含有黄素的 ODN 进行光照射，由于分子间黄素对吲哚醌-香豆素共轭物的光敏还原作用，香豆素被有效地释放出来，且具有多次周转。在发生这种光反应的同时，我们可以观察到经过目标 DNA 光照射的样品溶液发出强烈的荧光，而没有目标 DNA 的对照溶液则发出微弱的荧光。
• Photoaddition of alcohols and ethers to flavins in the presence of EDTA
  作者：Paul F. Heelis、Rosemarie F. Hartman、Seth D. Rose

  DOI：10.1016/0040-4039(94)88073-5

  日期：1994.8

  Alcohols and ethers that do not normally photoadd to flavins do so in the presence of EDTA to produce covalent attachment of an alkyl group at C(4a). Thus, irradiation of an aerated solution containing both EDTA and t-butanol resulted in rapid formation of an air-stable, reduced flavin, FlH-C(4a)CH2C(CH3)2OH. Similar results were also obtained with ethanol, 1-propanol, 2-propanol, pinacol, poly(ethylene

  通常在EDTA存在下，通常不光加到黄素上的醇和醚会在C（4a）处产生烷基的共价连接。因此，辐射同时包含EDTA和叔丁醇的充气溶液导致快速形成空气稳定的，还原的黄素FlH-C（4a）CH 2 C（CH 3）2 OH。用乙醇，1-丙醇，2-丙醇，频哪醇，聚乙二醇和二恶烷也获得了相似的结果，但是用甲醇或丙酮却未得到相似的结果。
• Novel Functional Peptide Nucleic Acid Monomer and Process for Producing the Same
  申请人：Ikeda Hisafumi

  公开号：US20080138817A1

  公开（公告）日：2008-06-12

  A compound represented by general formula (I) below; (in the formula, A denotes B denotes R denotes H, NO 2 , NH 2 , NHCbz, Br, F, Cl or SO 3 Na 2 , and n is an integer of 1 to 4 ), and a process for producing the above compound characterised in that it includes a reaction between an activated ester and a t-butoxycarbonylaminoethylamine or an ω-amino acid derivative.

  以下是一种由通式（I）表示的化合物；（在公式中，A代表B代表R代表H，NO2，NH2，NHCbz，Br，F，Cl或SO3Na2，n是1到4的整数），以及一种生产上述化合物的过程，其特征在于它包括激活酯和t-丁氧羰基氨乙胺或ω-氨基酸衍生物之间的反应。