bengal rosa A | 4370-09-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: bengal rosa A
• 英文别名: rose bengal A；acid red 93；Bengal Pink A (BPA); 3',6'-Dichlor-2,4,5,7-tetrajod-fluorescein；3,6-Dichlor-2',4',5',7'-tetrajod-fluorescein；3',6'-dichloro-2,4,5,7-tetraiodofluorescein；3,6-Dichloro-2-(3-hydroxy-2,4,5,7-tetraiodo-6-oxoxanthen-9-yl)benzoic acid
• CAS: 4370-09-6
• 化学式: C₂₀H₆Cl₂I₄O₅
• 分子量: 904.789
• InChiKey: VWOSOMIYKBKWDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bengal rosa A 、 silver nitrate 生成 disilver;3,6-dichloro-2-(2,4,5,7-tetraiodo-3-oxido-6-oxoxanthen-9-yl)benzoate
  参考文献：
  名称：

  LOGINOVA, L. P.;MCHEDLOV-PETROSYAN, N. O., BECTH. XARK. YH-TA,(1989) N40, S. 65-71

  摘要：

  DOI：
• 作为产物：
  描述：

  4,7-dichloro-7a-(6'-hydroxy-3'-oxo-3H-xanthen-9'-yl)benzoic acid 在 碘 、 碘酸 作用下， 以 乙醇 、 水 为溶剂， 以49%的产率得到bengal rosa A
  参考文献：
  名称：

  Rose Bengal analogs and vesicular glutamate transporters (VGLUTs)

  摘要：

  Vesicular glutamate transporters (VGLUTs) allow the loading of presynaptic glutamate vesicles and thus play a critical role in glutamatergic synaptic transmission. Rose Bengal (RB) is the most potent known VGLUT inhibitor (K-i 25 nM); therefore we designed, synthesized and tested in brain preparations, a series of analogs based on this scaffold. We showed that among the two tautomers of RB, the carboxylic and not the lactonic form is active against VGLUTs and generated a pharmacophore model to determine the minimal structure requirements. We also tested RB specificity in other neurotransmitter uptake systems. RB proved to potently inhibit VMAT (K-i 64 nM) but weakly VACHT (K-i > 9.7 mu M) and may be a useful tool in glutamate/acetylcholine co-transmission studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.069

文献信息

• Influence of substituents in haloderivatives of fluorescein on the emission capacity of their complexes with metals
  作者：M. A. Matveets、S. D. Akhmetova

  DOI：10.1007/bf00658416

  日期：1991.11
• LOGINOVA, L. P.;MCHEDLOV-PETROSYAN, N. O., BECTH. XARK. YH-TA,(1989) N40, S. 65-71
  作者：LOGINOVA, L. P.、MCHEDLOV-PETROSYAN, N. O.

  DOI：——

  日期：——
• Rose Bengal analogs and vesicular glutamate transporters (VGLUTs)
  作者：Nicolas Pietrancosta、Albane Kessler、Franck-Cyril Favre-Besse、Nicolas Triballeau、Thomas Quentin、Bruno Giros、Salah El Mestikawy、Francine C. Acher

  DOI：10.1016/j.bmc.2010.06.069

  日期：2010.9

  Vesicular glutamate transporters (VGLUTs) allow the loading of presynaptic glutamate vesicles and thus play a critical role in glutamatergic synaptic transmission. Rose Bengal (RB) is the most potent known VGLUT inhibitor (K-i 25 nM); therefore we designed, synthesized and tested in brain preparations, a series of analogs based on this scaffold. We showed that among the two tautomers of RB, the carboxylic and not the lactonic form is active against VGLUTs and generated a pharmacophore model to determine the minimal structure requirements. We also tested RB specificity in other neurotransmitter uptake systems. RB proved to potently inhibit VMAT (K-i 64 nM) but weakly VACHT (K-i > 9.7 mu M) and may be a useful tool in glutamate/acetylcholine co-transmission studies. (C) 2010 Elsevier Ltd. All rights reserved.