靛草素 | 487-94-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 中文名称: 靛草素
• 中文别名: (6E)-4-氯-6-[(2-氯苯基)(十六烷基氨基)甲亚基]环己-2,4-二烯-1-酮
• 英文名称: Indican
• 英文别名: 1H-indol-3-yl hydrogen sulfate；3-indolyl hydrogen sulfate；3-indoxylsulfuric acid；3-O-indoxyl sulfate；3-indoxyl sulfate；indoxyl 3-fosfate；Indoxyl sulfate
• CAS: 487-94-5
• 化学式: C₈H₇NO₄S
• mdl: MFCD00127900
• 分子量: 213.214
• InChiKey: BXFFHSIDQOFMLE-UHFFFAOYSA-N

物化性质

• 密度：
  1.666±0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 碰撞截面：
  140.6 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.8
• 氢给体数：
  2
• 氢受体数：
  4

ADMET

代谢

尿素毒素往往会因为饮食过量或者肾脏过滤功能不佳而在血液中积聚。大多数尿素毒素是代谢废物，通常通过尿液或粪便排出。

Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

尿毒症毒素，如靛玉硫酸盐，通过有机离子转运体（尤其是OAT3）被积极运输到肾脏中。尿毒症毒素水平的增加可以刺激活性氧种类的产生。这似乎是通过尿毒症毒素直接结合或抑制NADPH氧化酶（尤其是肾脏和心脏中丰富的NOX4）来介导的（A7868）。活性氧种类可以诱导多种不同的DNA甲基转移酶（DNMTs），这些酶涉及到一种名为KLOTHO的蛋白的沉默。KLOTHO被发现具有在抗衰老、矿物质代谢和维生素D代谢中的重要作用。许多研究表明，在急性或慢性肾脏疾病中，由于局部活性氧种类水平升高，KLOTHO mRNA和蛋白水平会降低（A7869）。

Uremic toxins such as Indoxyl sulfate are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

长期暴露于尿毒症毒素可能会导致多种疾病，包括肾脏损伤、慢性肾病和心血管疾病。

Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

内源性的，摄入，皮肤（接触）

Endogenous, Ingestion, Dermal (contact)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

作为尿毒症毒素，这种化合物可以引起尿毒症综合征。尿毒症综合征可能影响身体的任何部位，并可能导致恶心、呕吐、食欲丧失和体重减轻。它还可能引起精神状态的变化，如混乱、意识减退、躁动、精神疾病、癫痫和昏迷。还可能出现异常出血，例如在非常轻微的损伤后自发或大量出血。心脏问题，如心律不齐、心脏包膜（心包炎）炎症和心脏压力增加，也可能出现在尿毒症综合征患者身上。由于肺部和胸壁之间（胸腔积液）的液体积聚导致的呼吸急促也可能出现。

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

来源:Toxin and Toxin Target Database (T3DB)

反应信息

• 作为反应物：
  描述：

  靛草素 在 arylsulfatase from Helix pomatia 作用下， 以 aq. acetate buffer 为溶剂， 反应 24.0h， 生成 吲哚酚
  参考文献：
  名称：

  使用质谱对螺旋螺旋藻中的芳基硫酸酯酶进行全面的动力学和底物特异性分析。

  摘要：

  硫酸酯酶将硫酸化的代谢产物水解成其相应的醇，并存在于生活的所有领域。这些酶已在药物的代谢研究，兴奋剂控制分析以及代谢组学中得到了重要应用。由于涉及硫酸化代谢物的代谢过程与人体病理生理状况之间的联系，人们对硫酸酯酶的兴趣有所增加。在本文中，我们介绍了从蜗牛螺旋果树提取的最常用的芳基硫酸酯酶的首次综合底物特异性和动力学分析。在过去，这种酶以酶的粗混合物形式使用，但是最近，我们已经纯化了该硫酸酯酶，以在代谢组学驱动的硫酸盐代谢物发现中的新应用。为了评估这种混杂硫酸酯酶的底物特异性，我们合成了一系列结构多样的新型硫酸盐代谢物，并采用质谱分析法对动力学底物水解进行了评估。我们对纯化的酶的分析表明，硫酸酯酶对具有双环或三环芳族骨架的代谢物具有强烈的偏好，而对单环芳族酚则具有较小的偏好。该代谢物文库和质谱方法可用于表征人类和肠道菌群中其他硫酸酯酶，以研究它们与疾病发展的关系。我们对纯化的酶的分析表明，硫

  DOI：

  10.1016/j.bmc.2019.01.031
• 作为产物：
  描述：

  2-硝基苯基丙炔酸 生成 靛草素
  参考文献：
  名称：

  Asayama, vol. 1, p. 115,123

  摘要：

  DOI：

文献信息

• [EN] CROSS-LINKING COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS DE RÉTICULATION ET PROCÉDÉS D'UTILISATION
  申请人：UNIV NORTH CAROLINA STATE

  公开号：WO2021016537A1

  公开（公告）日：2021-01-28

  Compounds comprising a cross-linking moiety and a protecting group are described herein along with their methods of use. The cross-linking moiety may comprise an indoxyl and the protecting group may comprise a sugar (e.g., a glucuronide or glucoside), phosphoester, or sulfoester group. The cross-linking moiety and protecting group may be attached to each other via an oxygen atom, sulfur atom, or linker. In some embodiments, the linker attaching the cross-linking moiety and protecting group is a self-immolative linker. A compound of the present invention may cross-link under physiological conditions and/or in vivo.

  本文描述了包含交联基团和保护基团的化合物，以及它们的使用方法。交联基团可能包括吲哚基团，保护基团可能包括糖类（例如葡萄糖醛酸盐或葡萄糖苷）、磷酸酯或磺酸酯基团。交联基团和保护基团可以通过氧原子、硫原子或连接剂相互连接。在某些实施例中，连接交联基团和保护基团的连接剂是自解离连接剂。本发明的化合物可能在生理条件和/或体内发生交联。
• New enzymatic and mass spectrometric methodology for the selective investigation of gut microbiota-derived metabolites
  作者：Caroline Ballet、Mário S. P. Correia、Louis P. Conway、Theresa L. Locher、Laura C. Lehmann、Neeraj Garg、Miroslav Vujasinovic、Sebastian Deindl、J.-Matthias Löhr、Daniel Globisch

  DOI：10.1039/c8sc01502c

  日期：——

  through metabolic interaction. Selective investigation of the co-metabolism of bacteria and their human host is a challenging task and methods for their analysis are limited. One class of metabolites associated with this co-metabolism are O-sulfated compounds. Herein, we describe the development of a new enzymatic assay for the selective mass spectrometric investigation of this phase II modification class

  肠道菌群通过代谢相互作用显着影响人体生理。对细菌及其人类宿主的共代谢的选择性研究是一项艰巨的任务，其分析方法受到限制。一类与此代谢相关的代谢产物是O-硫酸化的化合物。在这里，我们描述了一种新的酶促测定方法的开发，用于该第二阶段修饰类别的选择性质谱研究。对人类尿液和粪便样品的分析导致检测到206种硫酸化代谢产物，是人类代谢组数据库中报告的三倍。我们使用合成的内标和质谱碎裂实验确定了36种硫酸盐代谢物的化学结构，包括未知的和普遍报道的微生物来源的硫酸盐代谢物。我们的发现表明，酶样品预处理与最新的代谢组学分析相结合代表了一种新的有效策略，可用于发现人类样品中未知的微生物来源的代谢产物。
• Compositions and methods for enhanced mucosal delivery of Y2 receptor-binding peptides and methods for treating and preventing obesity
  申请人：Nastech Pharmaceutical Company Inc.

  公开号：US20040157777A1

  公开（公告）日：2004-08-12

  Pharmaceutical compositions and methods are described comprising at least one Y2 receptor-binding peptide, such as peptide YY(PYY), Neuropeptide Y (NPY) or Pancreatic Peptide (PP) and one or more mucosal delivery-enhancing agents for enhanced nasal mucosal delivery of the peptide YY, for treating a variety of diseases and conditions in mammalian subjects, including obesity.

  描述了包含至少一种Y2受体结合肽（如肽YY（PYY）、神经肽Y（NPY）或胰岛素肽（PP））和一种或多种黏膜传递增强剂的药物组合物和方法，以增强肽YY在鼻黏膜中的传递，用于治疗哺乳动物主体中的多种疾病和病况，包括肥胖。
• Intranasal administration of glucose-regulating peptides
  申请人：Quay C. Steven

  公开号：US20050143303A1

  公开（公告）日：2005-06-30

  Pharmaceutical compositions and methods are described comprising at least one glucose-regulating peptide, such as amylin, glucagon-like peptide-1 (GLP), pramlintide or exendin-4 and one or more mucosal delivery-enhancing agents for enhanced nasal mucosal delivery of the amylin, for treating a variety of diseases and conditions in mammalian subjects, including obesity and diabetes mellitus.

  本文介绍了一种药物组合和方法，其中包括至少一种调节葡萄糖的肽类，如降淀粉样肽、胰高血糖素样肽-1（GLP）、普拉林肽或外肽-4，以及一种或多种黏膜传递增强剂，以增强降淀粉样肽在鼻黏膜上的传递，用于治疗哺乳动物主体中的多种疾病和病况，包括肥胖和糖尿病。
• METHOD FOR PRODUCING GLUCOSIDES
  申请人：Motokucho Suguru

  公开号：US20130060015A1

  公开（公告）日：2013-03-07

  The present invention relates to methods for producing glucosides directly from glucose or a polysaccharide comprising glucose as a structural unit. The present invention provides a method comprising reacting glucose or a polysaccharide comprising glucose as a structural unit with a compound represented by R—OH in the presence of a supercritical or subcritical carbon dioxide to produce glucosides and a method comprising dissolving or suspending glucose or a polysaccharide comprising glucose as a structural unit in an organic solvent containing a compound represent by R—OH and reacting the glucose or polysaccharide with the compound represented by R—OH in the presence of a supercritical or subcritical carbon dioxide to produce glucosides.

  本发明涉及从葡萄糖或包含葡萄糖作为结构单元的多糖直接生产葡萄糖苷的方法。本发明提供了一种方法，包括在超临界或亚临界二氧化碳存在下，将葡萄糖或包含葡萄糖作为结构单元的多糖与表示为R-OH的化合物反应，以产生葡萄糖苷；以及一种方法，包括在含有表示为R-OH的化合物的有机溶剂中溶解或悬浮葡萄糖或包含葡萄糖作为结构单元的多糖，并在超临界或亚临界二氧化碳存在下，将葡萄糖或多糖与表示为R-OH的化合物反应，以产生葡萄糖苷。