Choline phosphate (BioDeep_00000003168)

 

Secondary id: BioDeep_00000405991

natural product human metabolite Endogenous blood metabolite


代谢物信息卡片


[2-(trimethylazaniumyl)ethoxy]phosphonic acid

化学式: [C5H15NO4P]+ (184.073866)
中文名称: 磷酸胆碱, 胆碱磷酸, 氯化磷酰胆碱
谱图信息: 最多检出来源 Homo sapiens(blood) 0.03%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

Choline phosphate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/choline_phosphate (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000003168). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C[N+1](C)(C)CCOP(O)(O)=O
InChI: InChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)/p+1

描述信息

Phosphorylcholine, also known as choline phosphate or N-trimethyl-2-aminoethylphosphonate, is a member of the class of compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. Phosphorylcholine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Phosphorylcholine can be found in a number of food items such as grapefruit, lime, black cabbage, and barley, which makes phosphorylcholine a potential biomarker for the consumption of these food products. Phosphorylcholine can be found primarily in most biofluids, including urine, blood, saliva, and cerebrospinal fluid (CSF), as well as throughout most human tissues. Phosphorylcholine exists in all eukaryotes, ranging from yeast to humans. In humans, phosphorylcholine is involved in several metabolic pathways, some of which include phosphatidylcholine biosynthesis PC(13D5/9D5), phosphatidylcholine biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)), phosphatidylcholine biosynthesis PC(14:0/20:1(11Z)), and phosphatidylcholine biosynthesis PC(11D5/9D5). Phosphorylcholine is also involved in few metabolic disorders, which include fabry disease, gaucher disease, and krabbe disease. Moreover, phosphorylcholine is found to be associated with alzheimers disease and multi-infarct dementia. Phosphorylcholine (abbreviated ChoP) is the hydrophilic polar head group of some phospholipids, which is composed of a negatively charged phosphate bonded to a small, positively charged choline group. Phosphorylcholine is part of platelet-activating factor; the phospholipid phosphatidylcholine as well as sphingomyelin, the only phospholipid of the membrane that is not built with a glycerol backbone. Treatment of cell membranes, like those of RBCs, by certain enzymes, like some phospholipase A2 renders the phosphorylcholine moiety exposed to the external aqueous phase, and thus accessible for recognition by the immune system. Antibodies against phosphorylcholine are naturally occurring autoantibodies that are created by CD5+/B-1 B cells and are referred to as non-pathogenic autoantibodies .
Phosphorylcholine, also known as choline phosphate or CHOP, belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. The phosphate of choline, and the parent compound of the phosphorylcholine family. Phosphorylcholine exists in all living species, ranging from bacteria to humans. Within humans, phosphorylcholine participates in a number of enzymatic reactions. In particular, phosphorylcholine can be converted into choline through its interaction with the enzyme phosphoethanolamine/phosphocholine phosphatase. In addition, phosphorylcholine can be converted into CDP-choline; which is mediated by the enzyme choline-phosphate cytidylyltransferase a. In humans, phosphorylcholine is involved in phospholipid biosynthesis. Outside of the human body, phosphorylcholine has been detected, but not quantified in several different foods, such as barley, pak choy, black radish, saskatoon berries, and acorns.
Acquisition and generation of the data is financially supported in part by CREST/JST.
KEIO_ID P074

同义名列表

19 个代谢物同义名

[2-(trimethylazaniumyl)ethoxy]phosphonic acid; Trimethyl(2-(phosphonooxy)ethyl)ammonium; N-Trimethyl-2-aminoethylphosphonic acid; Choline chloride dihydrogen phosphate; N-Trimethyl-2-aminoethylphosphonate; Phosphate chloride, choline; Chloride, choline phosphate; Chloride, phosphorylcholine; Choline phosphate chloride; Phosphorylcholine chloride; Choline phosphoric acid; Phosphoryl-choline; Phosphate, choline; Phosphorylcholine; Choline phosphate; O-Phosphocholine; Phosphocholine; CHOP; Phosphorylcholine



数据库引用编号

28 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(15)

BioCyc(2)

PlantCyc(0)

代谢反应

3028 个相关的代谢反应过程信息。

Reactome(125)

BioCyc(7)

WikiPathways(6)

Plant Reactome(302)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(2588)

PharmGKB(0)

7 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • Lihe Lu, Yuanzhi Ye, Yajun Chen, Liyun Feng, Jiali Huang, Qingchun Liang, Zirong Lan, Qianqian Dong, Xiaoyu Liu, Yining Li, Xiuli Zhang, Jing-Song Ou, An Chen, Jianyun Yan. Oxidized phospholipid POVPC contributes to vascular calcification by triggering ferroptosis of vascular smooth muscle cells. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2024 Apr; 38(7):e23592. doi: 10.1096/fj.202302570r. [PMID: 38581243]
  • Yajie Chang, Jing Chen, Hongwei Zhu, Rong Huang, Jinxia Wu, Yanyan Lin, Quanquan Li, Guiping Shen, Jianghua Feng. Metabolic Characteristics and Discriminative Diagnosis of Growth Hormone Deficiency and Idiopathic Short Stature in Preadolescents and Adolescents. Molecules (Basel, Switzerland). 2024 Apr; 29(7):. doi: 10.3390/molecules29071661. [PMID: 38611940]
  • Asmaa F Ibrahim, Sahar M Selim, Dalia A Shafey, Dina M Sweed, Shaimaa A Farag, Marwa A Gouda. Appraisal of Chitosan-Coated Lipid Nano-Combination with Miltefosine and Albendazole in the Treatment of Murine Trichinellosis: Experimental Study with Evaluation of Immunological and Immunohistochemical Parameters. Acta parasitologica. 2024 Mar; 69(1):929-950. doi: 10.1007/s11686-024-00799-x. [PMID: 38489009]
  • Jason Foster, Michael McPhee, Lambert Yue, Graham Dellaire, Steven Pelech, Neale D Ridgway. Lipid- and phospho-regulation of CTP:Phosphocholine Cytidylyltransferase α association with nuclear lipid droplets. Molecular biology of the cell. 2024 Mar; 35(3):ar33. doi: 10.1091/mbc.e23-09-0354. [PMID: 38170618]
  • Xiangyang Ye, Xiongzhi He, Zhenting Hu, Fengfeng Zheng, Xiaogang Huang, Xuemei Xie, Feihua Chen, Hanbing Ou, Rongxian Qiu. Metabolomic analysis identifies dysregulation of lipid metabolism in the immune clearance phase of chronic hepatitis B patients. Journal of pharmaceutical and biomedical analysis. 2024 Feb; 239(?):115900. doi: 10.1016/j.jpba.2023.115900. [PMID: 38064772]
  • Si Chen, Jian-Jun Gao, Yu-Jia Liu, Zhi-Wei Mo, Fang-Yuan Wu, Zuo-Jun Hu, Yue-Ming Peng, Xiao-Qin Zhang, Zhen-Sheng Ma, Ze-Long Liu, Jian-Yun Yan, Zhi-Jun Ou, Yan Li, Jing-Song Ou. The oxidized phospholipid PGPC impairs endothelial function by promoting endothelial cell ferroptosis via FABP3. Journal of lipid research. 2024 02; 65(2):100499. doi: 10.1016/j.jlr.2024.100499. [PMID: 38218337]
  • Rebeca Serrano, David Martin-Hidalgo, Jon Bilbao, Ganeko Bernardo-Seisdedos, Oscar Millet, Luis J Garcia-Marin, Maria Julia Bragado. Quantitative Analysis of the Human Semen Phosphorometabolome by 31P-NMR. International journal of molecular sciences. 2024 Jan; 25(3):. doi: 10.3390/ijms25031682. [PMID: 38338962]
  • Jingwei Zhou, Huihui Wu, Jianxiong Shao, Jia-Huan Qu, Minyi Li, Huayun Zhaiman, Qiqin Wang, Zhengjin Jiang. Biomimetic affinity membrane roll column for rapid purification of C-reactive protein. Journal of chromatography. A. 2024 Jan; 1713(?):464541. doi: 10.1016/j.chroma.2023.464541. [PMID: 38041978]
  • Jiaming Xu, Vyshnavi Karra, Danielle E Large, Debra T Auguste, Francisco R Hung. Understanding the Mechanical Properties of Ultradeformable Liposomes Using Molecular Dynamics Simulations. The journal of physical chemistry. B. 2023 11; 127(44):9496-9512. doi: 10.1021/acs.jpcb.3c04386. [PMID: 37879075]
  • Yu V Zaytseva, I V Zaytseva, N V Surovtsev. Characterization of conformational states of POPC and DPPCd62 in POPC/DPPCd62/cholesterol mixtures using Raman spectroscopy. Chemistry and physics of lipids. 2023 10; 256(?):105337. doi: 10.1016/j.chemphyslip.2023.105337. [PMID: 37579987]
  • Alessandre C Crispim, Shirley M A Crispim, Jéssica R Rocha, Jeferson S Ursulino, Roberto R Sobrinho, Viviane A Porto, Edson S Bento, Antônio E G Santana, Luiz C Caetano. Light effects on Lasiodiplodia theobromae metabolome cultured in vitro. Metabolomics : Official journal of the Metabolomic Society. 2023 08; 19(8):75. doi: 10.1007/s11306-023-02041-7. [PMID: 37580624]
  • Behnaz Bagheri, Phansiri Boonnoy, Jirasak Wong-Ekkabut, Mikko Karttunen. Effect of oxidation on POPC lipid bilayers: anionic carboxyl group plays a major role. Physical chemistry chemical physics : PCCP. 2023 Jul; 25(27):18310-18321. doi: 10.1039/d3cp01692g. [PMID: 37401178]
  • Vesela Yordanova, Rusina Hazarosova, Victoria Vitkova, Albena Momchilova, Bozhil Robev, Biliana Nikolova, Plamen Krastev, Philippe Nuss, Miglena I Angelova, Galya Staneva. Impact of Truncated Oxidized Phosphatidylcholines on Phospholipase A2 Activity in Mono- and Polyunsaturated Biomimetic Vesicles. International journal of molecular sciences. 2023 Jul; 24(13):. doi: 10.3390/ijms241311166. [PMID: 37446342]
  • Xiaoyan Gu, Rongguang Zhang, Yingwei Sun, Xinyi Ai, Yu Wang, Yaqi Lyu, Xiaoyu Wang, Yihan Wu, Zhi Wang, Nianping Feng, Ying Liu. Oral membrane-biomimetic nanoparticles for enhanced endocytosis and regulation of tumor-associated macrophage. Journal of nanobiotechnology. 2023 Jul; 21(1):206. doi: 10.1186/s12951-023-01949-5. [PMID: 37403048]
  • Daisuke Yasuda, Fumie Hamano, Kazuyuki Masuda, Märta Dahlström, Daiki Kobayashi, Nana Sato, Takao Hamakubo, Takao Shimizu, Satoshi Ishii. Inverse agonism of lysophospholipids with cationic head groups at Gi-coupled receptor GPR82. European journal of pharmacology. 2023 Jun; 954(?):175893. doi: 10.1016/j.ejphar.2023.175893. [PMID: 37392830]
  • Luis M Real Hernandez, Ilya Levental. Lipid packing is disrupted in copolymeric nanodiscs compared with intact membranes. Biophysical journal. 2023 06; 122(11):2256-2266. doi: 10.1016/j.bpj.2023.01.013. [PMID: 36641625]
  • Wei Jia, Xixuan Wu, Lin Shi. Spatiotemporal Variation of Residual Cortisol Obstructs Nutrient Acquisition in Animal-Derived Foods by Perturbing Glycerophospholipid Metabolism. Journal of agricultural and food chemistry. 2023 Jun; ?(?):. doi: 10.1021/acs.jafc.3c02397. [PMID: 37265263]
  • Adam Taleb, Peter Willeit, Shahzada Amir, Thomas Perkmann, Maria Ozsvar Kozma, Martin L Watzenböck, Christoph J Binder, Joseph L Witztum, Sotirios Tsimikas. High Immunoglobulin-M Levels to Oxidation-Specific Epitopes Are Associated with Lower Risk of Acute Myocardial Infarction. Journal of lipid research. 2023 May; ?(?):100391. doi: 10.1016/j.jlr.2023.100391. [PMID: 37211249]
  • Huafeng Geng, Wenhai Lin, Junbao Liu, Qing Pei, Zhigang Xie. Choline phosphate lipid-hitchhiked near-infrared BODIPY nanoparticles for enhanced phototheranostics. Journal of materials chemistry. B. 2023 May; ?(?):. doi: 10.1039/d3tb00175j. [PMID: 37190791]
  • Qiong Xiao, Xue Pan, Yang Xu, Stacy D Singer, Guanqun Chen. Genome-wide characterization of plant CTP:phosphocholine cytidylyltransferases through evolutionary, biochemical and structural analyses. The Plant journal : for cell and molecular biology. 2023 May; ?(?):. doi: 10.1111/tpj.16264. [PMID: 37129256]
  • Inna Ermilova, Jan Swenson. Ionizable lipids penetrate phospholipid bilayers with high phase transition temperatures: perspectives from free energy calculations. Chemistry and physics of lipids. 2023 Mar; ?(?):105294. doi: 10.1016/j.chemphyslip.2023.105294. [PMID: 37003484]
  • Eulalie J Lafarge, Pierre Muller, André P Schroder, Ekaterina Zaitseva, Jan C Behrends, Carlos M Marques. Activation energy for pore opening in lipid membranes under an electric field. Proceedings of the National Academy of Sciences of the United States of America. 2023 03; 120(11):e2213112120. doi: 10.1073/pnas.2213112120. [PMID: 36881617]
  • Kenji Nakayama, Xin Li, Koji Shimizu, Shusuke Akamatsu, Takahiro Inoue, Takashi Kobayashi, Osamu Ogawa, Takayuki Goto. qShot MALDI analysis: A rapid, simple, convenient, and reliable quantitative phospholipidomics approach using MALDI-TOF/MS. Talanta. 2023 Mar; 254(?):124099. doi: 10.1016/j.talanta.2022.124099. [PMID: 36502612]
  • Zhiwei Chen, Chendi Zhu, Jiawen Yang, Mengyun Zhang, Jiaming Yuan, Yuan Shen, Jingwei Zhou, Hao Huang, Dongsheng Xu, Jacques Crommen, Zhengjin Jiang, Qiqin Wang. Inside-Out Oriented Choline Phosphate-Based Biomimetic Magnetic Nanomaterials for Precise Recognition and Analysis of C-Reactive Protein. Analytical chemistry. 2023 02; 95(6):3532-3543. doi: 10.1021/acs.analchem.2c05683. [PMID: 36744576]
  • Kexin Zhang, Yanyan Liu, Lingyun Liu, Baoling Bai, Lin Shi, Qin Zhang. Untargeted Metabolomics Analysis Using UHPLC-Q-TOF/MS Reveals Metabolic Changes Associated with Hypertension in Children. Nutrients. 2023 Feb; 15(4):. doi: 10.3390/nu15040836. [PMID: 36839194]
  • Sanyog G Shitole, Mahim Naveed, Zheng Wang, Tao Wang, Yoko Kato, Bharath Ambale-Venkatesh, Robert C Kaplan, Phyllis C Tien, Kathryn Anastos, Jason M Lazar, João A C Lima, Qibin Qi, Jorge R Kizer. Metabolomic Profiling of Cardiac Fibrosis and Steatosis in Women With or at Risk for HIV. Journal of acquired immune deficiency syndromes (1999). 2023 02; 92(2):162-172. doi: 10.1097/qai.0000000000003118. [PMID: 36215981]
  • Ruikang Yuan, Haohao Huang. Anchoring of Amyloid-β onto Polyunsaturated Phospholipid Membranes. Journal of biomolecular structure & dynamics. 2023 02; 41(3):1098-1108. doi: 10.1080/07391102.2021.2016488. [PMID: 34915817]
  • Joris R Delanghe, Jonas Himpe, Jerina Boelens, Dominique Benoit, Bram Gadeyne, Marijn M Speeckaert, Frederick Verbeke. C-reactive protein interacts with amphotericin B liposomes and its potential clinical consequences. Clinical chemistry and laboratory medicine. 2023 Jan; ?(?):. doi: 10.1515/cclm-2022-1213. [PMID: 36691951]
  • Chung-Hao Liu, Catherine Cheu, John G Barker, Lin Yang, Mu-Ping Nieh. Facile polymerization in a bicellar template to produce polymer nano-rings. Journal of colloid and interface science. 2023 Jan; 630(Pt A):629-637. doi: 10.1016/j.jcis.2022.09.141. [PMID: 36272217]
  • Johannes Zeller, Karen S Cheung Tung Shing, Tracy L Nero, James D McFadyen, Guy Krippner, Balázs Bogner, Sheena Kreuzaler, Jurij Kiefer, Verena K Horner, David Braig, Habiba Danish, Sara Baratchi, Mark Fricke, Xiaowei Wang, Michel G Kather, Bernd Kammerer, Kevin J Woollard, Prerna Sharma, Craig J Morton, Geoffrey Pietersz, Michael W Parker, Karlheinz Peter, Steffen U Eisenhardt. A novel phosphocholine-mimetic inhibits a pro-inflammatory conformational change in C-reactive protein. EMBO molecular medicine. 2023 01; 15(1):e16236. doi: 10.15252/emmm.202216236. [PMID: 36468184]
  • Peiyu Wang, Yuyao Yuan, Mantang Qiu. Identification of Plasma Metabolites Associated with Lung Cancer Survival. Methods in molecular biology (Clifton, N.J.). 2023; 2695(?):181-193. doi: 10.1007/978-1-0716-3346-5_12. [PMID: 37450119]
  • Johan Frostegård. Systemic lupus erythematosus and cardiovascular disease. Journal of internal medicine. 2023 01; 293(1):48-62. doi: 10.1111/joim.13557. [PMID: 35982610]
  • Qin Zhang, Hong Zhang, Chun-Mei Yang, Bo Wang, Chen-Yang Li, Qi Li. [Mechanism of active ingredients in Periploca forrestii compound against rheumatoid arthritis based on integrative metabolomics and network pharmacology]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2023 Jan; 48(2):507-516. doi: 10.19540/j.cnki.cjcmm.20220913.702. [PMID: 36725240]
  • Yihui Dong, Nir Kampf, Yaelle Schilt, Wei Cao, Uri Raviv, Jacob Klein. Dehydration does not affect lipid-based hydration lubrication. Nanoscale. 2022 Dec; 14(48):18241-18252. doi: 10.1039/d2nr04799c. [PMID: 36468753]
  • Hiroshi Takahashi, Tomohiro Hayakawa, Asami Makino, Kunihiko Iwamoto, Kazuki Ito, Satoshi B Sato, Toshihide Kobayashi. Long chain ceramides raise the main phase transition of monounsaturated phospholipids to physiological temperature. Scientific reports. 2022 12; 12(1):20803. doi: 10.1038/s41598-022-25330-y. [PMID: 36460753]
  • Juliana B T Carnielli, Anuja Dave, Audrey Romano, Sarah Forrester, Pedro R de Faria, Renata Monti-Rocha, Carlos H N Costa, Reynaldo Dietze, Ian A Graham, Jeremy C Mottram. 3'Nucleotidase/nuclease is required for Leishmania infantum clinical isolate susceptibility to miltefosine. EBioMedicine. 2022 Dec; 86(?):104378. doi: 10.1016/j.ebiom.2022.104378. [PMID: 36462405]
  • Gorane Santamaría, Natali Naude, Julia Watson, John Irvine, Thomas Lloyd, Ian Bennett, Graham Galloway, Peter Malycha, Carolyn Mountford. Breast Tissue Chemistry Measured In Vivo In Healthy Women Correlate with Breast Density and Breast Cancer Risk. Journal of magnetic resonance imaging : JMRI. 2022 11; 56(5):1355-1369. doi: 10.1002/jmri.28168. [PMID: 35319148]
  • Wellington C Leite, Yuqi Wu, Sai Venkatesh Pingali, Raquel L Lieberman, Volker S Urban. Change in Morphology of Dimyristoylphosphatidylcholine/Bile Salt Derivative Bicelle Assemblies with Dodecylmaltoside in the Disk and Ribbon Phases. The journal of physical chemistry letters. 2022 Oct; 13(42):9834-9840. doi: 10.1021/acs.jpclett.2c02445. [PMID: 36250687]
  • Jhinuk Saha, Priyankar Bose, Shailendra Dhakal, Preetam Ghosh, Vijayaraghavan Rangachari. Ganglioside-Enriched Phospholipid Vesicles Induce Cooperative Aβ Oligomerization and Membrane Disruption. Biochemistry. 2022 10; 61(20):2206-2220. doi: 10.1021/acs.biochem.2c00495. [PMID: 36173882]
  • Hamad Alrbyawi, Sai H S Boddu, Ishwor Poudel, Manjusha Annaji, Nur Mita, Robert D Arnold, Amit K Tiwari, R Jayachandra Babu. Cardiolipin for Enhanced Cellular Uptake and Cytotoxicity of Thermosensitive Liposome-Encapsulated Daunorubicin toward Breast Cancer Cell Lines. International journal of molecular sciences. 2022 Oct; 23(19):. doi: 10.3390/ijms231911763. [PMID: 36233061]
  • Zhenzhen Li, Yue Tan, Xiang Li, Jing Quan, Ann M Bode, Ya Cao, Xiangjian Luo. DHRS2 inhibits cell growth and metastasis in ovarian cancer by downregulation of CHKα to disrupt choline metabolism. Cell death & disease. 2022 10; 13(10):845. doi: 10.1038/s41419-022-05291-w. [PMID: 36192391]
  • Wei Xu, Ákos Kenéz, Sabine Mann, Thomas R Overton, Joseph J Wakshlag, Daryl V Nydam, Tao Feng, Francisco Leal Yepes. Effects of dietary branched-chain amino acid supplementation on serum and milk metabolome profiles in dairy cows during early lactation. Journal of dairy science. 2022 Oct; 105(10):8497-8508. doi: 10.3168/jds.2022-21892. [PMID: 35965128]
  • Valeria A Zykova, Nikolay V Surovtsev. Brillouin Spectroscopy of Binary Phospholipid-Cholesterol Bilayers. Applied spectroscopy. 2022 Oct; 76(10):1206-1215. doi: 10.1177/00037028221111147. [PMID: 35712869]
  • Alicja Sęk, Paulina Perczyk, Aleksandra Szcześ, Rainhard Machatschek, Paweł Wydro. Studies on the interactions of tiny amounts of common ionic surfactants with unsaturated phosphocholine lipid model membranes. Chemistry and physics of lipids. 2022 10; 248(?):105236. doi: 10.1016/j.chemphyslip.2022.105236. [PMID: 36007625]
  • Andrea Cerrato, Anna Laura Capriotti, Chiara Cavaliere, Carmela Maria Montone, Susy Piovesana, Aldo Laganà. Novel Aza-Paternò-Büchi Reaction Allows Pinpointing Carbon-Carbon Double Bonds in Unsaturated Lipids by Higher Collisional Dissociation. Analytical chemistry. 2022 09; 94(38):13117-13125. doi: 10.1021/acs.analchem.2c02549. [PMID: 36121000]
  • Man Thi Hong Nguyen, Denys Biriukov, Carmelo Tempra, Katarina Baxova, Hector Martinez-Seara, Hüseyin Evci, Vandana Singh, Radek Šachl, Martin Hof, Pavel Jungwirth, Matti Javanainen, Mario Vazdar. Ionic Strength and Solution Composition Dictate the Adsorption of Cell-Penetrating Peptides onto Phosphatidylcholine Membranes. Langmuir : the ACS journal of surfaces and colloids. 2022 09; 38(37):11284-11295. doi: 10.1021/acs.langmuir.2c01435. [PMID: 36083171]
  • Trang Thi Thuy Nguyen, Seungjoo Haam, Joon-Seo Park, Sang-Wha Lee. Cysteine-Encapsulated Liposome for Investigating Biomolecular Interactions at Lipid Membranes. International journal of molecular sciences. 2022 Sep; 23(18):. doi: 10.3390/ijms231810566. [PMID: 36142476]
  • Aditi Dixit, Gregor P Jose, Chitra Shanbhag, Nitin Tagad, Jeet Kalia. Metabolic Labeling-Based Chemoproteomics Establishes Choline Metabolites as Protein Function Modulators. ACS chemical biology. 2022 08; 17(8):2272-2283. doi: 10.1021/acschembio.2c00400. [PMID: 35802552]
  • Yanli Wang, Chunxia Li, Jingjing Zhang, Xiumei Xu, Lin Fu, Jie Xu, Hong Zhu, Ying Hu, Chengbin Li, Mengjie Wang, Yingjie Wu, Xiaoju Zou, Bin Liang. Polyunsaturated fatty acids promote the rapid fusion of lipid droplets in Caenorhabditis elegans. The Journal of biological chemistry. 2022 08; 298(8):102179. doi: 10.1016/j.jbc.2022.102179. [PMID: 35752365]
  • Rongrong Du, Xu Li, Yong-Hao Ma, Yongsheng Luo, Chu Wang, Qian Ma, Xiaolin Lu. Exploring Interfacial Hydrolysis of Artificial Neutral Lipid Monolayer and Bilayer Catalyzed by Phospholipase C. Langmuir : the ACS journal of surfaces and colloids. 2022 07; 38(26):8104-8113. doi: 10.1021/acs.langmuir.2c00995. [PMID: 35749224]
  • Anh H Ngo, Artik Elisa Angkawijaya, Ying-Chen Lin, Yu-Chi Liu, Yuki Nakamura. The phospho-base N-methyltransferases PMT1 and PMT2 produce phosphocholine for leaf growth in phosphorus-starved Arabidopsis. Journal of experimental botany. 2022 05; 73(9):2985-2994. doi: 10.1093/jxb/erab436. [PMID: 35560207]
  • Augusta de Santis, Ernesto Scoppola, Maria Francesca Ottaviani, Alexandros Koutsioubas, Lester C Barnsley, Luigi Paduano, Gerardino D'Errico, Irene Russo Krauss. Order vs. Disorder: Cholesterol and Omega-3 Phospholipids Determine Biomembrane Organization. International journal of molecular sciences. 2022 May; 23(10):. doi: 10.3390/ijms23105322. [PMID: 35628128]
  • Lais Alonso, Laryssa Ketelyn Lima Pimenta, André Kipnis, Antonio Alonso. Mycobacterium abscessus cell wall and plasma membrane characterization by EPR spectroscopy and effects of amphotericin B, miltefosine and nerolidol. Biochimica et biophysica acta. Biomembranes. 2022 05; 1864(5):183872. doi: 10.1016/j.bbamem.2022.183872. [PMID: 35085568]
  • Yuichiro Takagi, Noriyuki Uchida, Yasutaka Anraku, Takahiro Muraoka. Stabilization of bicelles using metal-binding peptide for extended blood circulation. Chemical communications (Cambridge, England). 2022 Apr; 58(33):5164-5167. doi: 10.1039/d2cc01058e. [PMID: 35388392]
  • Alfredo E Cardenas, Chad I Drexler, Rachel Nechushtai, Ron Mittler, Assaf Friedler, Lauren J Webb, Ron Elber. Peptide Permeation across a Phosphocholine Membrane: An Atomically Detailed Mechanism Determined through Simulations and Supported by Experimentation. The journal of physical chemistry. B. 2022 04; 126(15):2834-2849. doi: 10.1021/acs.jpcb.1c10966. [PMID: 35388695]
  • Hui Wang, Mani Ordoubadi, Patrick Connaughton, Kellisa Lachacz, Nicholas Carrigy, Scott Tavernini, Andrew R Martin, Warren H Finlay, David Lechuga-Ballesteros, Reinhard Vehring. Spray Dried Rugose Lipid Particle Platform for Respiratory Drug Delivery. Pharmaceutical research. 2022 Apr; 39(4):805-823. doi: 10.1007/s11095-022-03242-w. [PMID: 35364777]
  • Fiona Gordon, Yannick Casamayou-Boucau, Alan G Ryder. Evaluating the interaction of human serum albumin (HSA) and 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) liposomes in different aqueous environments using anisotropy resolved multi-dimensional emission spectroscopy (ARMES). Colloids and surfaces. B, Biointerfaces. 2022 Mar; 211(?):112310. doi: 10.1016/j.colsurfb.2021.112310. [PMID: 35007857]
  • Lívia Mendes Carvalho, Miriã Rodrigues Gusmão, Ana Flávia Pereira Costa, Rory Cristiane Fortes de Brito, Rodrigo Dian de Oliveira Aguiar-Soares, Jamille Mirelle de Oliveira Cardoso, Alexandre Barbosa Reis, Cláudia Martins Carneiro, Bruno Mendes Roatt. Immunochemotherapy for visceral leishmaniasis: combinatorial action of Miltefosine plus LBSapMPL vaccine improves adaptative Th1 immune response with control of splenic parasitism in experimental hamster model. Parasitology. 2022 03; 149(3):371-379. doi: 10.1017/s0031182021001906. [PMID: 35264268]
  • Jing Lu, Ying Li, Yong Ai Li, Li Wang, An Rong Zeng, Xiao Liang Ma, Jin Wei Qiang. In vivo detection of dysregulated choline metabolism in paclitaxel-resistant ovarian cancers with proton magnetic resonance spectroscopy. Journal of translational medicine. 2022 02; 20(1):92. doi: 10.1186/s12967-022-03292-z. [PMID: 35168606]
  • Shengran Li, Xintao Xie, Wenliang Wang, Sangni Jiang, Weikang Mei, Yuanhua Zhang, Sanrong Liu, Xifei Yu. Choline phosphate lipid as an intra-crosslinker in liposomes for drug and antibody delivery under guard. Nanoscale. 2022 Feb; 14(6):2277-2286. doi: 10.1039/d1nr07103c. [PMID: 35080548]
  • P F She, L L Xu, Y Q Liu, Z H Li, S S Liu, Y M Li, L Y Zhou, Y Wu. [Perifosine inhibits biofilm formation of Pseudomonas aeruginosa by interacting with PqsE protein]. Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine]. 2022 Feb; 56(2):192-196. doi: 10.3760/cma.j.cn112150-20211020-00970. [PMID: 35184449]
  • Jeffrey A Julien, Sarah G Mutchek, Nathan J Wittenberg, Kerney Jebrell Glover. Biophysical characterization of full-length oleosin in dodecylphosphocholine micelles. Proteins. 2022 02; 90(2):560-565. doi: 10.1002/prot.26252. [PMID: 34596903]
  • M Kazemi, R Madani, M R Aghamaali, T Emami, F Golchinfar, L Heshmati. Preparation and Characterization of Nanoliposome Containing Isolated VP1 Protein of Foot and Mouth Disease Virus as a Model of Vaccine. Archives of Razi Institute. 2022 02; 77(1):37-44. doi: 10.22092/ari.2021.353322.1596. [PMID: 35891774]
  • Helena Østergaard Rasmussen, Daniel E Otzen, Jan Skov Pedersen. Induction, inhibition, and incorporation: Different roles for anionic and zwitterionic lysolipids in the fibrillation of the functional amyloid FapC. The Journal of biological chemistry. 2022 02; 298(2):101569. doi: 10.1016/j.jbc.2022.101569. [PMID: 35007533]
  • Olga Lucía Fernández, Mariana Rosales-Chilama, Natali Quintero, Bruno L Travi, Dawn M Wetzel, María Adelaida Gómez, Nancy Gore Saravia. Potency and Preclinical Evidence of Synergy of Oral Azole Drugs and Miltefosine in an Ex Vivo Model of Leishmania (Viannia) panamensis Infection. Antimicrobial agents and chemotherapy. 2022 01; 66(1):e0142521. doi: 10.1128/aac.01425-21. [PMID: 34694879]
  • Benjamin M King, Jennifer Fiegel. Zwitterionic Polymer Coatings Enhance Gold Nanoparticle Stability and Uptake in Various Biological Environments. The AAPS journal. 2022 01; 24(1):18. doi: 10.1208/s12248-021-00652-3. [PMID: 34984558]
  • Tsukasa Nakatoh, Takuji Osaki, Sohma Tanimoto, Md Golam Sarowar Jahan, Tomohisa Kawakami, Kentaro Chihara, Nobuyuki Sakai, Shigehiko Yumura. Cell behaviors within a confined adhesive area fabricated using novel micropatterning methods. PloS one. 2022; 17(1):e0262632. doi: 10.1371/journal.pone.0262632. [PMID: 35030217]
  • Semra Palić, Jos H Beijnen, Thomas P C Dorlo. An update on the clinical pharmacology of miltefosine in the treatment of leishmaniasis. International journal of antimicrobial agents. 2022 Jan; 59(1):106459. doi: 10.1016/j.ijantimicag.2021.106459. [PMID: 34695563]
  • Kai On Chu, Kwok Ping Chan, Yolanda Wong Ying Yip, Wai Kit Chu, Chi Chiu Wang, Chi Pui Pang. Systemic and Ocular Anti-Inflammatory Mechanisms of Green Tea Extract on Endotoxin-Induced Ocular Inflammation. Frontiers in endocrinology. 2022; 13(?):899271. doi: 10.3389/fendo.2022.899271. [PMID: 35909558]
  • Lejla Alic, Christoph J Binder, Nikolina Papac-Milicevic. The OSE complotype and its clinical potential. Frontiers in immunology. 2022; 13(?):1010893. doi: 10.3389/fimmu.2022.1010893. [PMID: 36248824]
  • Amir Abbas Momtazi-Borojeni, Elham Abdollahi, Mahmoud R Jaafari, Maciej Banach, Gerald F Watts, Amirhossein Sahebkar. Negatively-charged Liposome Nanoparticles Can Prevent Dyslipidemia and Atherosclerosis Progression in the Rabbit Model. Current vascular pharmacology. 2022; 20(1):69-76. doi: 10.2174/1570161119666210820115150. [PMID: 34414873]
  • Michel G Kather, Johannes Zeller, Dietmar Plattner, Bernhard Breit, Sheena Kreuzaler, Guy Krippner, Karlheinz Peter, Steffen U Eisenhardt, Bernd Kammerer. Pharmacokinetic study of the novel phosphocholine derivative 3-dibutylaminopropylphosphonic acid by LC-MS coupling. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2021 Dec; 1186(?):122998. doi: 10.1016/j.jchromb.2021.122998. [PMID: 34798417]
  • Nabila A El-Sheridy, Riham M El-Moslemany, Alyaa A Ramadan, Maged W Helmy, Labiba K El-Khordagui. Enhancing the in vitro and in vivo activity of itraconazole against breast cancer using miltefosine-modified lipid nanocapsules. Drug delivery. 2021 Dec; 28(1):906-919. doi: 10.1080/10717544.2021.1917728. [PMID: 33960245]
  • Ae-Ri Cho Lee, Heekyung Moon, Kazuhiko Ishihara. Stabilization of Lipid Lamellar Bilayer Structure of Stratum Corneum Modulated by Poly (2-methacryloyloxyethyl phosphorylcholine) in Relation to Skin Hydration and Skin Protection. Tissue engineering and regenerative medicine. 2021 12; 18(6):953-962. doi: 10.1007/s13770-021-00379-4. [PMID: 34460064]
  • Andrea Cerrato, Sara Elsa Aita, Anna Laura Capriotti, Chiara Cavaliere, Carmela Maria Montone, Susy Piovesana, Aldo Laganà. Fully Automatized Detection of Phosphocholine-Containing Lipids through an Isotopically Labeled Buffer Modification Workflow. Analytical chemistry. 2021 11; 93(45):15042-15048. doi: 10.1021/acs.analchem.1c02944. [PMID: 34726396]
  • Mark B Frampton, Doruntina Yakoub, John Katsaras, Paul M Zelisko, Drew Marquardt. A calorimetric, volumetric and combined SANS and SAXS study of hybrid siloxane phosphocholine bilayers. Chemistry and physics of lipids. 2021 11; 241(?):105149. doi: 10.1016/j.chemphyslip.2021.105149. [PMID: 34627769]
  • Vivien Walter, Céline Ruscher, Adrien Gola, Carlos M Marques, Olivier Benzerara, Fabrice Thalmann. Ripple-like instability in the simulated gel phase of finite size phosphocholine bilayers. Biochimica et biophysica acta. Biomembranes. 2021 11; 1863(11):183714. doi: 10.1016/j.bbamem.2021.183714. [PMID: 34331947]
  • Xiao Wang, Xiaowei Chen, Sylvie Nonin-Lecomte, Serge Bouaziz. Acetonitrile allows indirect replacement of nondeuterated lipid detergents by deuterated lipid detergents for the nuclear magnetic resonance study of detergent-soluble proteins. Protein science : a publication of the Protein Society. 2021 11; 30(11):2324-2332. doi: 10.1002/pro.4174. [PMID: 34462977]
  • So-Yeon Park, Jee-Heun Kim, Jang-Hyun Choi, Choong-Jae Lee, Won-Jae Lee, Sehoon Park, Zee-Yong Park, Jeong-Heum Baek, Jeong-Seok Nam. Lipid raft-disrupting miltefosine preferentially induces the death of colorectal cancer stem-like cells. Clinical and translational medicine. 2021 11; 11(11):e552. doi: 10.1002/ctm2.552. [PMID: 34841679]
  • Alexander Rysin, Michael Paal, Wouter J M Lokerse, Barbara Wedmann, Martin Hossann, Michael Vogeser, Gerhard Winter, Lars H Lindner. Evaluation of release and pharmacokinetics of hexadecylphosphocholine (miltefosine) in phosphatidyldiglycerol-based thermosensitive liposomes. Biochimica et biophysica acta. Biomembranes. 2021 11; 1863(11):183698. doi: 10.1016/j.bbamem.2021.183698. [PMID: 34283999]
  • Di Yang, Xiong Liu, Xiaoming Yin, Tian Dong, Min Yu, Yan Wu. Rice Non-Specific Phospholipase C6 Is Involved in Mesocotyl Elongation. Plant & cell physiology. 2021 Oct; 62(6):985-1000. doi: 10.1093/pcp/pcab069. [PMID: 34021760]
  • Danya A Dean, Gautham Gautham, Jair L Siqueira-Neto, James H McKerrow, Pieter C Dorrestein, Laura-Isobel McCall. Spatial metabolomics identifies localized chemical changes in heart tissue during chronic cardiac Chagas Disease. PLoS neglected tropical diseases. 2021 10; 15(10):e0009819. doi: 10.1371/journal.pntd.0009819. [PMID: 34606502]
  • Pradeep Kumar Sheokand, Monika Narwal, Vandana Thakur, Asif Mohmmed. GlmS mediated knock-down of a phospholipase expedite alternate pathway to generate phosphocholine required for phosphatidylcholine synthesis in Plasmodium falciparum. The Biochemical journal. 2021 09; 478(18):3429-3444. doi: 10.1042/bcj20200549. [PMID: 34133721]
  • Anna Adler, Yuuki Inoue, Yuya Sato, Kazuhiko Ishihara, Kristina N Ekdahl, Bo Nilsson, Yuji Teramura. Synthesis of poly(2-methacryloyloxyethyl phosphorylcholine)-conjugated lipids and their characterization and surface properties of modified liposomes for protein interactions. Biomaterials science. 2021 Sep; 9(17):5854-5867. doi: 10.1039/d1bm00570g. [PMID: 34286724]
  • Hiroki Nakano, Sachiro Kakinoki, Yasuhiko Iwasaki. Long-lasting hydrophilic surface generated on poly(dimethyl siloxane) with photoreactive zwitterionic polymers. Colloids and surfaces. B, Biointerfaces. 2021 Sep; 205(?):111900. doi: 10.1016/j.colsurfb.2021.111900. [PMID: 34102530]
  • Prantar Dutta, Debabrata Pramanik, Jayant K Singh. Phase Behavior of Pure PSPC and PEGylated Multicomponent Lipid and Their Interaction with Paclitaxel: An All-Atom MD Study. Langmuir : the ACS journal of surfaces and colloids. 2021 08; 37(34):10259-10271. doi: 10.1021/acs.langmuir.1c01049. [PMID: 34406778]
  • Jessica D Murillo-Saich, Cesar Diaz-Torne, M Angeles Ortiz, Roxana Coras, Paulo Gil-Alabarse, Anders Pedersen, Hector Corominas, Silvia Vidal, Monica Guma. Metabolomics profiling predicts outcome of tocilizumab in rheumatoid arthritis: an exploratory study. Metabolomics : Official journal of the Metabolomic Society. 2021 08; 17(9):74. doi: 10.1007/s11306-021-01822-2. [PMID: 34402961]
  • Cristina Manis, Margherita Addis, Maria Sitzia, Paola Scano, Viviana Garau, Andrea Cabiddu, Marco Caredda, Antonio Pirisi, Antonio Pulina, Pierpaolo Roggero, Pierluigi Caboni. Untargeted lipidomics of ovine milk to analyse the influence of different diet regimens. The Journal of dairy research. 2021 Aug; 88(3):261-264. doi: 10.1017/s0022029921000583. [PMID: 34372949]
  • Lais Alonso, Sebastião Antônio Mendanha, Rodrigo Saar Gomes, Miriam Leandro Dorta, Antonio Alonso. Comparative EPR spectroscopy analysis of amphotericin B and miltefosine interactions with Leishmania, erythrocyte and macrophage membranes. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2021 Aug; 163(?):105859. doi: 10.1016/j.ejps.2021.105859. [PMID: 33894283]
  • Dimitri Bulté, Lieselotte Van Bockstal, Laura Dirkx, Magali Van den Kerkhof, Carl De Trez, Jean-Pierre Timmermans, Sarah Hendrickx, Louis Maes, Guy Caljon. Miltefosine enhances infectivity of a miltefosine-resistant Leishmania infantum strain by attenuating its innate immune recognition. PLoS neglected tropical diseases. 2021 07; 15(7):e0009622. doi: 10.1371/journal.pntd.0009622. [PMID: 34292975]
  • Shailesh Kumar Samal, Ole Fröbert, Jonas Kindberg, Peter Stenvinkel, Johan Frostegård. Potential natural immunization against atherosclerosis in hibernating bears. Scientific reports. 2021 06; 11(1):12120. doi: 10.1038/s41598-021-91679-1. [PMID: 34108551]
  • Thaís Amanda de Lima Nunes, Lellis Henrique Costa, Julyanne Maria Saraiva De Sousa, Vanessa Maria Rodrigues De Souza, Raiza Raianne Luz Rodrigues, Maria da Conceição Albuquerque Val, Anna Carolina Toledo da Cunha Pereira, Gustavo Portela Ferreira, Marcos Vinícius Da Silva, João Marcos Antônio Rodrigues Da Costa, Leiz Maria Costa Véras, Roseane Costa Diniz, Klinger Antonio da Franca Rodrigues. Eugenia piauhiensis Vellaff. essential oil and γ-elemene its major constituent exhibit antileishmanial activity, promoting cell membrane damage and in vitro immunomodulation. Chemico-biological interactions. 2021 Apr; 339(?):109429. doi: 10.1016/j.cbi.2021.109429. [PMID: 33713644]
  • Undine Christmann, Courtney L Hancock, Cathleen M Poole, Audrey L Emery, Jesse R Poovey, Casey Hagg, Eric A Mattson, Jon J Scarborough, Jordan S Christopher, Alexander T Dixon, Dustin J Craney, Paul L Wood. Dynamics of DHA and EPA supplementation: incorporation into equine plasma, synovial fluid, and surfactant glycerophosphocholines. Metabolomics : Official journal of the Metabolomic Society. 2021 04; 17(5):41. doi: 10.1007/s11306-021-01792-5. [PMID: 33866431]
  • Anke E Kip, Séverine Blesson, Fabiana Alves, Monique Wasunna, Robert Kimutai, Peninah Menza, Bewketu Mengesha, Jos H Beijnen, Asrat Hailu, Ermias Diro, Thomas P C Dorlo. Low antileishmanial drug exposure in HIV-positive visceral leishmaniasis patients on antiretrovirals: an Ethiopian cohort study. The Journal of antimicrobial chemotherapy. 2021 04; 76(5):1258-1268. doi: 10.1093/jac/dkab013. [PMID: 33677546]
  • Hong-Kai Xie, Guan-Hua Zhao, Zi-Xuan Wu, De-Yang Li, Man-Tong Zhao, Ao Li, Hui-Lin Liu, Da-Yong Zhou, Bei-Wei Zhu. Differences in oxidative susceptibilities between glycerophosphocholine and glycerophosphoethanolamine in dried scallop (Argopecten irradians) adductor muscle during storage: an oxidation kinetic assessment. Journal of the science of food and agriculture. 2021 Mar; 101(4):1554-1561. doi: 10.1002/jsfa.10774. [PMID: 32869299]
  • Jaime A Soto, María Isabel Méndez, Jonathan D Berman. Case Report: COVID-19 Misdiagnosed as a Drug Reaction to Miltefosine. The American journal of tropical medicine and hygiene. 2021 Mar; 104(5):1659-1660. doi: 10.4269/ajtmh.20-1510. [PMID: 33705346]
  • Andrew A Voak, Andy Harris, Jose Miguel Coteron-Lopez, Iñigo Angulo-Barturen, Santiago Ferrer-Bazaga, Simon L Croft, Karin Seifert. Pharmacokinetic / pharmacodynamic relationships of liposomal amphotericin B and miltefosine in experimental visceral leishmaniasis. PLoS neglected tropical diseases. 2021 03; 15(3):e0009013. doi: 10.1371/journal.pntd.0009013. [PMID: 33651812]
  • Sauman Singh-Phulgenda, Prabin Dahal, Roland Ngu, Brittany J Maguire, Alice Hawryszkiewycz, Sumayyah Rashan, Matthew Brack, Christine M Halleux, Fabiana Alves, Kasia Stepniewska, Piero L Olliaro, Philippe J Guerin. Serious adverse events following treatment of visceral leishmaniasis: A systematic review and meta-analysis. PLoS neglected tropical diseases. 2021 03; 15(3):e0009302. doi: 10.1371/journal.pntd.0009302. [PMID: 33780461]
  • Qiuli Cheng, Anika Benozir Asha, Yang Liu, Yi-Yang Peng, Diana Diaz-Dussan, Zuosen Shi, Zhanchen Cui, Ravin Narain. Antifouling and Antibacterial Polymer-Coated Surfaces Based on the Combined Effect of Zwitterions and the Natural Borneol. ACS applied materials & interfaces. 2021 Feb; 13(7):9006-9014. doi: 10.1021/acsami.0c22658. [PMID: 33576614]