lysophosphatidylserine | 119786-67-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: lysophosphatidylserine
• 英文别名: 18:0 LPS；LPS(18:0)；lysophosphatidylserine (18:0)；LysoPS (18:0)；(2S)-2-amino-3-[hydroxy-[(2R)-2-hydroxy-3-octadecanoyloxypropoxy]phosphoryl]oxypropanoic acid
• CAS: 119786-67-3
• 化学式: C₂₄H₄₈NO₉P
• 分子量: 525.62
• InChiKey: ZPDQFUYPBVXUKS-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  35
• 可旋转键数：
  26
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  166
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  [(2R)-3-[[(2S)-3-oxo-3-phenylmethoxy-2-(phenylmethoxycarbonylamino)propoxy]-phenylmethoxyphosphoryl]oxy-2-phenylmethoxypropyl] octadecanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 24.0h， 以58%的产率得到lysophosphatidylserine
  参考文献：
  名称：

  Synthesis and Evaluation of Lysophosphatidylserine Analogues as Inducers of Mast Cell Degranulation. Potent Activities of Lysophosphatidylthreonine and Its 2-Deoxy Derivative

  摘要：

  In response to various exogenous stimuli, mast cells (MCs) release a wide variety of inflammatory mediators stored in their cytoplasmic granules and this release initiates subsequent allergic reactions. Lysophosphatidylserine (lysoPS) has been known as an exogenous inducer to potentiate histamine release from MCs, though even at submicromolar concentrations. In this study, through SAR studies on lysoPS against MC degranulation, we identified lysoPT, a threonine-containing lysophospholipid and its 2-deoxy derivative as novel strong agonists. LysoPT and its 2-deoxy derivative induced histamine release from MCs both in vitro and in vivo at a concentration less than one-tenth that of lysoPS. Notably, lysoPT did not activate a recently proposed lysoPS receptor on MCs, GPR34, demonstrating the presence of another undefined receptor reactive to both lysoPS and lysoPT that is involved in MC degranulation. Thus, the present strong agonists, lysoPT and its 2-deoxy derivative, will be useful tools to understand the mechanisms of lysoPS-induced activation of degranulation of MCs.

  DOI：

  10.1021/jm900598m

文献信息

• Gas-filled stabilized particles and methods of use
  申请人：Children's Medical Center Corporation

  公开号：US10577554B2

  公开（公告）日：2020-03-03

  Provided herein are various gas-filled particles having a stabilized membrane that encapsulates the gas. Pharmaceutical compositions, methods of use and treatment, and methods of preparation are also described.

  本文提供了各种充满气体的颗粒，这些颗粒具有封装气体的稳定膜。此外，还介绍了药物组合物、使用和处理方法以及制备方法。
• Fatty acid chain length drives lysophosphatidylserine-dependent immunological outputs
  作者：Neha Khandelwal、Minhaj Shaikh、Amol Mhetre、Shubham Singh、Theja Sajeevan、Alaumy Joshi、Kithiganahalli Narayanaswamy Balaji、Harinath Chakrapani、Siddhesh S. Kamat

  DOI：10.1016/j.chembiol.2021.01.008

  日期：2021.8
• GAS-FILLED STABILIZED PARTICLES AND METHODS OF USE
  申请人：CHILDREN'S MEDICAL CENTER CORPORATION

  公开号：US20160030596A1

  公开（公告）日：2016-02-04

  Provided herein are various gas-filled particles having a stabilized membrane that encapsulates the gas. Pharmaceutical compositions, methods of use and treatment, and methods of preparation are also described.
• [EN] SYSTEMS AND METHODS TO PREDICT INCREASED RISK FOR ADVERSE CARDIOVASCULAR EVENTS IN HUMAN IMMUNODEFICIENCY VIRUS (HIV)-INFECTED SUBJECTS<br/>[FR] SYSTÈMES ET PROCÉDÉS POUR PRÉDIRE UN RISQUE ACCRU D'ÉVÉNEMENTS CARDIOVASCULAIRES INDÉSIRABLES CHEZ DES SUJETS INFECTÉS PAR LE VIRUS DE L'IMMUNODÉFICIENCE HUMAINE (VIH)
  申请人：BLOODWORKS

  公开号：WO2020252365A1

  公开（公告）日：2020-12-17

  The current disclosure provides systems and methods to predict increased risk of adverse cardiovascular events in subjects infected with human immunodeficiency virus (HIV) at risk for cardiovascular events. The systems and methods measure levels of one or more of glutathione peroxidase-3 (GPX-3), platelet factor 4 (PF4), platelet basic protein (PBP), thrombospondin-1 (TSP-1), plasma kallikrein (KLKB1), serotonin, factor V (coagulation factor V), protein C (PROC), protein C inhibitor (PCI), C-reactive protein (CRP), linoleic acid (LA), arachidonic acid (AA), 12-hydroxyeicosatetraenoic acid (12-HETE), lysophosphatidylserine (LysoPS) 18:0, lysoPS 18:1, lysoPS 20:4, Cysteine (Cys), and/or protein bound Cysteine (P-ss-Cys). If an increased risk is detected, a therapeutic intervention can be initiated.
• Synthesis and Evaluation of Lysophosphatidylserine Analogues as Inducers of Mast Cell Degranulation. Potent Activities of Lysophosphatidylthreonine and Its 2-Deoxy Derivative
  作者：Masazumi Iwashita、Kumiko Makide、Taro Nonomura、Yoshimasa Misumi、Yuko Otani、Mayuko Ishida、Ryo Taguchi、Masafumi Tsujimoto、Junken Aoki、Hiroyuki Arai、Tomohiko Ohwada

  DOI：10.1021/jm900598m

  日期：2009.10.8

  In response to various exogenous stimuli, mast cells (MCs) release a wide variety of inflammatory mediators stored in their cytoplasmic granules and this release initiates subsequent allergic reactions. Lysophosphatidylserine (lysoPS) has been known as an exogenous inducer to potentiate histamine release from MCs, though even at submicromolar concentrations. In this study, through SAR studies on lysoPS against MC degranulation, we identified lysoPT, a threonine-containing lysophospholipid and its 2-deoxy derivative as novel strong agonists. LysoPT and its 2-deoxy derivative induced histamine release from MCs both in vitro and in vivo at a concentration less than one-tenth that of lysoPS. Notably, lysoPT did not activate a recently proposed lysoPS receptor on MCs, GPR34, demonstrating the presence of another undefined receptor reactive to both lysoPS and lysoPT that is involved in MC degranulation. Thus, the present strong agonists, lysoPT and its 2-deoxy derivative, will be useful tools to understand the mechanisms of lysoPS-induced activation of degranulation of MCs.