bilirubin IXα dimethyl ester | 71327-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: bilirubin IXα dimethyl ester
• 英文别名: bilirubin-dimethylester；3,3'-(2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-diyl)-bis-propionic acid dimethyl ester；Bilirubindimethylester；methyl 3-[5-[(4-ethenyl-3-methyl-5-oxopyrrol-2-ylidene)methyl]-2-[[5-[(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-3-(3-methoxy-3-oxopropyl)-4-methyl-1H-pyrrol-2-yl]methyl]-4-methyl-1H-pyrrol-3-yl]propanoate
• CAS: 71327-45-2；71327-46-3；78856-00-5
• 化学式: C₃₅H₄₀N₄O₆
• 分子量: 612.726
• InChiKey: UWZUXDQSJUVVTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bilirubin IXα dimethyl ester 在 碳酸氢钠 、 silver nitrate 作用下， 以 四氢呋喃 、 水 为溶剂， 以22%的产率得到3-vinyl-14-formyl-2,7,13-trimethyl-8,12-dimethoxycarbonylethyl-1-oxo-15H,16H-tripyrrin
  参考文献：
  名称：

  AN EFFICIENT ONE-STEP CONVERSION OF BILIVERDINS TO 14-FORMYLTRIPYRRINONES

  摘要：

  DOI：

  10.1080/00304940209355755
• 作为产物：
  描述：

  甲醇 、 bilirubin IXα 在 氯化亚砜 作用下， 生成 bilirubin IXα dimethyl ester
  参考文献：
  名称：

  非结合胆红素及其衍生物通过抑制 MMP9 和 MAPK 通路改善 IMQ 诱导的小鼠银屑病样皮肤炎症

  摘要：

  牛皮癣是一种慢性免疫介导的炎症性皮肤病，涉及角质形成细胞增殖失调。银屑病皮肤病变的特征是发红、增厚和脱屑。 IL-23/IL-17 的白细胞介素轴与人类牛皮癣的发展密切相关。

  DOI：

  10.1016/j.intimp.2024.111679

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Cu: MVol.B4, 128, page 1727 - 1729
  作者：

  DOI：——

  日期：——
• Kuester, W., Zeitschrift fur Physiologische Chemie, 1925, vol. 149, p. 30 - 43
  作者：Kuester, W.

  DOI：——

  日期：——
• Biliverdin Amides Reveal Roles for Propionate Side Chains in Bilin Reductase Recognition and in Holophytochrome Assembly and Photoconversion
  作者：Lixia Shang、Nathan C. Rockwell、Shelley S. Martin、J. Clark Lagarias

  DOI：10.1021/bi100756x

  日期：2010.7.27

  Linear tetrapyrroles (bilins) perform important antioxidant and light-harvesting functions in cells from bacteria to humans. To explore the role of the propionate moieties in bilin metabolism, we report the semisynthesis of mono- and diamides of biliverdin IX alpha and those of its non-natural XIII alpha isomer. Initially, these were examined as substrates of two types of NADPH-dependent biliverdin reductase, BVR and BvdR, and of the representative ferredoxin-dependent bilin reductase, phycocyanobilin:ferredoxin oxidoreductase (PcyA). Our studies indicate that the NADPH-dependent biliverdin reductases are less accommodating to amidation of the propionic acid side chains of biliverdin IX alpha than PcyA, which does not require free carboxylic acid side chains to yield its phytobilin product, phycocyanobilin. Bilin amides were also assembled with BV-type and phytobilin-type apophytochromes, demonstrating a role for the 8-propionate in the formation of the spectroscopically native P-r dark states of these biliprotein photosensors. Neither ionizable propionate side chain proved to be essential to primary photoisomerization for both classes of phytochromes, but an unsubstituted 12-propionate was required for full photointerconversion of phytobilin-type phytochrome Cph1. Taken together, these studies provide insight into the roles of the ionizable propionate side chains in substrate discrimination by two bilin reductase families while further underscoring the mechanistic differences between the photoconversions of BV-type and phytobilin-type phytochromes.
• AN EFFICIENT ONE-STEP CONVERSION OF BILIVERDINS TO 14-FORMYLTRIPYRRINONES
  作者：Peng Wang、Yi Zhang、Qingqi Chen、Jin Shi Ma

  DOI：10.1080/00304940209355755

  日期：2002.4
• Unconjugated bilirubin and its derivative ameliorate IMQ-induced psoriasis-like skin inflammation in mice by inhibiting MMP9 and MAPK pathway
  作者：Madeva Bharatha、Manuganahalli B. Nandana、Raju Praveen、Spandan Nayaka、Devadasan Velmurugan、Bannikuppe S. Vishwanath、Rajesh Rajaiah

  DOI：10.1016/j.intimp.2024.111679

  日期：2024.3

  Psoriasis is a chronic immune-mediated inflammatory skin disease that involves dysregulated proliferation of keratinocytes. Psoriatic skin lesions are characterized by redness, thickness, and scaling. The interleukin axis of IL-23/IL-17 is critically involved in the development of human psoriasis.

  牛皮癣是一种慢性免疫介导的炎症性皮肤病，涉及角质形成细胞增殖失调。银屑病皮肤病变的特征是发红、增厚和脱屑。 IL-23/IL-17 的白细胞介素轴与人类牛皮癣的发展密切相关。