octyl cholate | 211448-18-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: octyl cholate
• 英文别名: octanyl cholate；octyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 211448-18-9
• 化学式: C₃₂H₅₆O₅
• 分子量: 520.794
• InChiKey: UWWJEEHHPYLXLT-BCTGSCMUSA-N

物化性质

• 沸点：
  616.4±55.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  octyl cholate 在 4-二甲氨基吡啶 氢氧化钾 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.25h， 生成 N-(3Alpha,7Alpha,12Alpha)三羟基-5β-胆甾烷-24-酰基牛黄酸
  参考文献：
  名称：

  Chemical modifications of bile acids under high-intensity ultrasound or microwave irradiation

  摘要：

  High-intensity ultrasound (HIU) and microwave (MW) irradiation, having emerged as effective promoters of organic reactions, were exploited for the synthesis of bile acids derivatives. Esterification, amidation, hydrolysis, oxidation, and reduction were investigated. Compared to conventional methods, both techniques proved much more efficient, increasing product yields and dramatically cutting down reaction times. Scaled-up studies are now under way. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.09.007
• 作为产物：
  描述：

  辛醇 、 胆酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 octyl cholate
  参考文献：
  名称：

  N-甲基苯并咪唑栓系胆酸两亲物可以根除金黄色葡萄球菌介导的生物膜和伤口感染

  摘要：

  与金黄色葡萄球菌等革兰氏阳性菌相关的感染构成重大威胁，因为这些细菌会产生耐药性，从而限制抗生素的应用。因此，需要新的抗菌剂来减轻这些感染。细菌膜呈现出有吸引力的治疗靶点，因为这些膜本质上是阴离子的，并且在其物理化学特征上发生改变的机会很小。抗菌肽 (AMPs) 可以通过静电相互作用破坏微生物膜，但 AMPs 的稳定性差会阻止其临床转化。在这里，我们介绍了八个N的合成-甲基苯并咪唑取代胆酸两亲物作为抗菌剂。我们针对不同的病原体筛选了这些新型杂环胆酸两亲物。在该系列中，CABI- 6在对金黄色葡萄球菌的杀菌活性方面优于其他两亲物。还研究了使用基于荧光的测定法对 CABI- 6的膜破坏特性，并推断 CABI- 6可以增强活性氧的产生。我们进一步证明了 CABI - 6可以清除预先形成的生物膜，并可以减轻小鼠模型中的伤口感染。

  DOI：

  10.3390/molecules27113501

文献信息

• Cationic Steroid Antimicrobial Compositions and Methods of Use
  申请人：Savage B. Paul

  公开号：US20070190067A1

  公开（公告）日：2007-08-16

  The invention provides methods for decreasing or inhibiting human immunodeficiency virus (HIV) infection or pathogenesis (e.g., illness) of a cell in vitro, ex vivo or in vivo, a symptom or pathology associated with human immunodeficiency virus (HIV) infection or pathogenesis (e.g., illness) in vitro, ex vivo or in vivo, or an adverse side effect of human immunodeficiency virus (HIV) infection or pathogenesis (e.g., illness) in vitro, ex vivo or in vivo. In one embodiment, a method of the invention includes treating a subject with an invention compound (e.g., cationic steroid antimicrobial or CSA).

  这项发明提供了用于在体外、体外或体内减少或抑制人类免疫缺陷病毒（HIV）感染或病理发生（例如，疾病）、在体外、体外或体内与人类免疫缺陷病毒（HIV）感染或病理发生（例如，疾病）相关的症状或病理、或在体外、体外或体内人类免疫缺陷病毒（HIV）感染或病理发生（例如，疾病）的不良副作用的方法。在一种实施方式中，该发明的方法包括使用一种发明化合物（例如，阳离子类固体抗菌剂或CSA）治疗受试者。
• Cationic Steroid Microbial Compositions and Methods of Use
  申请人：Savage B. Paul

  公开号：US20070191322A1

  公开（公告）日：2007-08-16

  The invention relates to methods for decreasing or inhibiting influenza virus infection or pathogenesis of a cell in vitro, ex vivo or in vivo, a symptom or pathology associated with influenza infection or pathogenesis in vitro, ex vivo or in vivo, or an adverse side effect of influenza infection or pathogenesis in vitro, ex vivo or in vivo. In one embodiment, a method of the invention includes treating a subject with an invention compound (e.g., cationic steroid antimicrobial or CSA).

  该发明涉及减少或抑制体外、体内或体外细胞的流感病毒感染或发病机制，体外、体内或体外与流感感染或发病机制相关的症状或病理学，或体外、体内或体外流感感染或发病机制的不良副作用的方法。在一种实施方式中，该发明的方法包括使用一种发明化合物（例如，阳离子类固醇抗微生物药物或CSA）治疗受试者。
• [EN] CATIONIC STEROID ANTIMICROBIAL DIAGNOSTIC, DETECTION, SCREENING AND IMAGING METHODS<br/>[FR] PROCÉDÉS DE DIAGNOSTIC, DE DÉTECTION, DE TRI ET D'IMAGERIE DE STÉROÏDES CATIONIQUES ANTIMICROBIENS
  申请人：UNIV BRIGHAM YOUNG

  公开号：WO2010036427A1

  公开（公告）日：2010-04-01

  The invention relates to diagnostic, detection, screening and imaging methods. In various embodiments, methods of diagnosis, detection, screening and imaging include administering a cationic steroid antimicrobial or CSA to a subject having or at risk of having an infection or a hyperproliferative disorder (e.g., a tumor, cancer or neoplasia) in an amount effective to diagnose or detect the infection or the hyperproliferative disorder (e.g., a tumor, cancer or neoplasia) in the subject. In a particular aspect, a detectable CSA, namely CSA- 13 labeled with 99mTc is used to detect the presence of an infection.

  该发明涉及诊断、检测、筛查和成像方法。在各种实施方式中，诊断、检测、筛查和成像的方法包括向患有感染或有感染风险的受试者施用阳离子类固醇抗菌药物或CSA，以有效诊断或检测受试者体内的感染或过度增殖疾病（例如肿瘤、癌症或新生物）。在一个特定方面，一种可检测的CSA，即用99mTc标记的CSA-13，被用于检测感染的存在。
• Oral Delivery of Cholic Acid-Derived Amphiphile Helps in Combating <i>Salmonella</i>-Mediated Gut Infection and Inflammation
  作者：Kavita Yadav、Prabhu Srinivas Yavvari、Sanjay Pal、Sandeep Kumar、Deepakkumar Mishra、Siddhi Gupta、Madhurima Mitra、Vijay Soni、Neha Khare、Priyanka Sharma、Chittur V. Srikanth、Arti Kapil、Archana Singh、Vinay Kumar Nandicoori、Avinash Bajaj

  DOI：10.1021/acs.bioconjchem.8b00880

  日期：2019.3.20

  A major impediment to developing effective antimicrobials against Gram-negative bacteria like Salmonella is the ability of the bacteria to develop resistance against existing antibiotics and the inability of the antimicrobials to clear the intracellular bacteria residing in the gastrointestinal tract. As the critical balance of charge and hydrophobicity is required for effective membrane-targeting antimicrobials without causing any toxicity to mammalian cells, herein we report the synthesis and antibacterial properties of cholic acid-derived amphiphiles conjugated with alkyl chains of varied hydrophobicity. Relative to other hydrophobic counterparts, a compound with hexyl chain (6) acted as an effective antimicrobial against different Gram-negative bacteria. Apart from its ability to permeate the outer and inner membranes of bacteria; compound 6 can cross the cellular and lysosomal barriers of epithelial cells and macrophages and kill the facultative intracellular bacteria without disrupting the mammalian cell membranes. Oral delivery of compound 6 was able to clear the Salmonella-mediated gut infection and inflammation, and was able to combat persistent, stationary, and multi-drug-resistant clinical strains. Therefore, our study reveals the ability of cholic acid-derived amphiphiles to clear intracellular bacteria and Salmonella-mediated gut infection and inflammation.

  开发有效的抗革兰氏阴性细菌（如沙门氏菌）抗菌药物的主要障碍是这些细菌能够对现有抗生素产生耐药性，以及抗微生物药物无法清除肠道内的细菌。由于有效的膜靶向抗微生物药物需要在不对哺乳动物细胞造成毒性的情况下，维持电荷和疏水性的关键平衡，因此我们在此报告了合成的胆酸衍生的两亲分子，这些分子与具有不同疏水性的烷基链结合。与其他疏水性相对物相比，具有己基链（6）的化合物对不同的革兰氏阴性细菌表现出有效的抗菌作用。除了能够渗透细菌的外膜和内膜之外，化合物6还可以穿越上皮细胞和巨噬细胞的细胞和溶酶体屏障，杀死兼性细胞内细菌，而不会破坏哺乳动物细胞膜。化合物6的口服投递能够清除沙门氏菌引起的肠道感染和炎症，并且能够抵抗持续、静止及多药耐药的临床菌株。因此，我们的研究揭示了胆酸衍生的两亲分子清除细胞内细菌以及沙门氏菌引起的肠道感染和炎症的能力。
• Preparation and Characterization of Cholic Acid-Derived Antimicrobial Agents with Controlled Stabilities
  作者：Qunying Guan、Chunhong Li、Erica J. Schmidt、J. Scott Boswell、Joshua P. Walsh、Glenn W. Allman、Paul B. Savage

  DOI：10.1021/ol0062704

  日期：2000.9.1

  Novel cholic acid-derived antimicrobial agents that decompose under mildly basic conditions have been prepared. These compounds range in biological properties from potent antibacterial activity to effective permeabilization of the outer membranes of Gram-negative bacteria.