2-Methacryloyloxyethyl phosphorylcholine (BioDeep_00000175045)
human metabolite blood metabolite
代谢物信息卡片
trimethyl[2-({2-[(2-methylprop-2-enoyl)oxy]ethyl phosphono}oxy)ethyl]azanium
化学式: C11H22NO6P (295.1184682)
中文名称: 2-(甲基丙烯酰氧基)乙基-2-(三甲基氨基)乙基磷酸酯
谱图信息:
最多检出来源 Homo sapiens(blood) 33.33%
分子结构信息
SMILES: CC(=C)C(=O)OCCOP(=O)([O-])OCC[N+](C)(C)C
InChI: InChI=1S/C11H22NO6P/c1-10(2)11(13)16-8-9-18-19(14,15)17-7-6-12(3,4)5/h1,6-9H2,2-5H3
数据库引用编号
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 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
- 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] - 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] - 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] - 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] - Alysha Spadafora, Myrto Korogiannaki, Heather Sheardown. Antifouling silicone hydrogel contact lenses via densely grafted phosphorylcholine polymers.
Biointerphases.
2020 08; 15(4):041013. doi:
10.1116/6.0000366. [PMID: 32867505] - Hui-Yu Liu, Ravi Kumar, Madoka Takai, Michael Hirtz. Enhanced Stability of Lipid Structures by Dip-Pen Nanolithography on Block-Type MPC Copolymer.
Molecules (Basel, Switzerland).
2020 Jun; 25(12):. doi:
10.3390/molecules25122768. [PMID: 32549371] - Xiaolong Liu, Bing Yang, Zhaosheng Hou, Na Zhang, Yuanyuan Gao. A mild method for surface-grafting MPC onto poly(ester-urethane) based on aliphatic diurethane diisocyanate with high grafting efficiency.
Materials science & engineering. C, Materials for biological applications.
2019 Nov; 104(?):109952. doi:
10.1016/j.msec.2019.109952. [PMID: 31499985] - Jia-Yu Wang, Wei Chen, Michihiro Nagao, Phullara Shelat, Brenton A G Hammer, Gregory T Tietjen, Kathleen D Cao, J Michael Henderson, Lilin He, Binhua Lin, Bulent Akgun, Mati Meron, Shuo Qian, Sarah Ward, Jeremy D Marks, Todd Emrick, Ka Yee C Lee. Tailoring Biomimetic Phosphorylcholine-Containing Block Copolymers as Membrane-Targeting Cellular Rescue Agents.
Biomacromolecules.
2019 09; 20(9):3385-3391. doi:
10.1021/acs.biomac.9b00621. [PMID: 31424203] - Tatsuro Goda, Yuki Imaizumi, Hiroaki Hatano, Akira Matsumoto, Kazuhiko Ishihara, Yuji Miyahara. Translocation Mechanisms of Cell-Penetrating Polymers Identified by Induced Proton Dynamics.
Langmuir : the ACS journal of surfaces and colloids.
2019 06; 35(24):8167-8173. doi:
10.1021/acs.langmuir.9b00856. [PMID: 31094202] - Alessia C G Weiss, Hannah G Kelly, Matthew Faria, Quinn A Besford, Adam K Wheatley, Ching-Seng Ang, Edmund J Crampin, Frank Caruso, Stephen J Kent. Link between Low-Fouling and Stealth: A Whole Blood Biomolecular Corona and Cellular Association Analysis on Nanoengineered Particles.
ACS nano.
2019 05; 13(5):4980-4991. doi:
10.1021/acsnano.9b00552. [PMID: 30998312] - Sana Asif, Kenta Asawa, Yuuki Inoue, Kazuhiko Ishihara, Björn Lindell, Robin Holmgren, Bo Nilsson, Anneli Rydén, Marianne Jensen-Waern, Yuji Teramura, Kristina N Ekdahl. Validation of an MPC Polymer Coating to Attenuate Surface-Induced Crosstalk between the Complement and Coagulation Systems in Whole Blood in In Vitro and In Vivo Models.
Macromolecular bioscience.
2019 05; 19(5):e1800485. doi:
10.1002/mabi.201800485. [PMID: 30786149] - Kazuhiko Ishihara. Revolutionary advances in 2-methacryloyloxyethyl phosphorylcholine polymers as biomaterials.
Journal of biomedical materials research. Part A.
2019 05; 107(5):933-943. doi:
10.1002/jbm.a.36635. [PMID: 30701666] - Gaoyang Guo, Wanyu Jin, Linhe Jin, Liang Chen, Yang Lei, Yunbing Wang. Hydrogel hybrid porcine pericardium for the fabrication of a pre-mounted TAVI valve with improved biocompatibility.
Journal of materials chemistry. B.
2019 03; 7(9):1427-1434. doi:
10.1039/c8tb02565g. [PMID: 32255013] - Anika Benozir Asha, Yangjun Chen, Huixin Zhang, Sina Ghaemi, Kazuhiko Ishihara, Yang Liu, Ravin Narain. Rapid Mussel-Inspired Surface Zwitteration for Enhanced Antifouling and Antibacterial Properties.
Langmuir : the ACS journal of surfaces and colloids.
2019 02; 35(5):1621-1630. doi:
10.1021/acs.langmuir.8b03810. [PMID: 30558423] - Bohan Cheng, Yuuki Inoue, Kazuhiko Ishihara. Surface functionalization of polytetrafluoroethylene substrate with hybrid processes comprising plasma treatment and chemical reactions.
Colloids and surfaces. B, Biointerfaces.
2019 Jan; 173(?):77-84. doi:
10.1016/j.colsurfb.2018.09.051. [PMID: 30267957] - Yihua Liu, Maria Chiara Munisso, Atsushi Mahara, Yusuke Kambe, Kyoko Fukazawa, Kazuhiko Ishihara, Tetsuji Yamaoka. A surface graft polymerization process on chemically stable medical ePTFE for suppressing platelet adhesion and activation.
Biomaterials science.
2018 Jun; 6(7):1908-1915. doi:
10.1039/c8bm00364e. [PMID: 29877532] - Shine Tone, Masahiro Hasegawa, Leonardo Puppulin, Giuseppe Pezzotti, Akihiro Sudo. Surface modifications and oxidative degradation in MPC-grafted highly cross-linked polyethylene liners retrieved from short-term total hip arthroplasty.
Acta biomaterialia.
2018 01; 66(?):157-165. doi:
10.1016/j.actbio.2017.11.012. [PMID: 29127066] - Xuhua Tan, Jiezhao Zhan, Yi Zhu, Ji Cao, Lin Wang, Sa Liu, Yingjun Wang, Zhenzhen Liu, Yingyan Qin, Mingxing Wu, Yizhi Liu, Li Ren. Improvement of Uveal and Capsular Biocompatibility of Hydrophobic Acrylic Intraocular Lens by Surface Grafting with 2-Methacryloyloxyethyl Phosphorylcholine-Methacrylic Acid Copolymer.
Scientific reports.
2017 01; 7(?):40462. doi:
10.1038/srep40462. [PMID: 28084469] - Bailiang Wang, Zi Ye, Yihong Tang, Yuemei Han, Quankui Lin, Huihua Liu, Hao Chen, Kaihui Nan. Fabrication of nonfouling, bactericidal, and bacteria corpse release multifunctional surface through surface-initiated RAFT polymerization.
International journal of nanomedicine.
2017 ; 12(?):111-125. doi:
10.2147/ijn.s107472. [PMID: 28053527] - Bailiang Wang, Zi Ye, Qingwen Xu, Huihua Liu, Quankui Lin, Hao Chen, Kaihui Nan. Construction of a temperature-responsive terpolymer coating with recyclable bactericidal and self-cleaning antimicrobial properties.
Biomaterials science.
2016 Nov; 4(12):1731-1741. doi:
10.1039/c6bm00587j. [PMID: 27782243] - Qi Huang, George Pak-Man Cheng, Kin Chiu, Gui-Qin Wang. Surface Modification of Intraocular Lenses.
Chinese medical journal.
2016 Jan; 129(2):206-14. doi:
10.4103/0366-6999.173496. [PMID: 26830993] - Shihori Yamane, Masayuki Kyomoto, Toru Moro, Kenichi Watanabe, Masami Hashimoto, Yoshio Takatori, Sakae Tanaka, Kazuhiko Ishihara. Effects of extra irradiation on surface and bulk properties of PMPC-grafted cross-linked polyethylene.
Journal of biomedical materials research. Part A.
2016 Jan; 104(1):37-47. doi:
10.1002/jbm.a.35538. [PMID: 26148654] - Takaharu Tateishi, Masayuki Kyomoto, Sachiro Kakinoki, Tetsuji Yamaoka, Kazuhiko Ishihara. Reduced platelets and bacteria adhesion on poly(ether ether ketone) by photoinduced and self-initiated graft polymerization of 2-methacryloyloxyethyl phosphorylcholine.
Journal of biomedical materials research. Part A.
2014 May; 102(5):1342-9. doi:
10.1002/jbm.a.34809. [PMID: 23720384] - Yihua Liu, Yuuki Inoue, Atsushi Mahara, Sachiro Kakinoki, Tetsuji Yamaoka, Kazuhiko Ishihara. Durable modification of segmented polyurethane for elastic blood-contacting devices by graft-type 2-methacryloyloxyethyl phosphorylcholine copolymer.
Journal of biomaterials science. Polymer edition.
2014; 25(14-15):1514-29. doi:
10.1080/09205063.2014.920172. [PMID: 24894706] - Yoshihiro Kawasaki, Yasuhiko Iwasaki. Surface modification of poly(ether ether ketone) with methacryloyl-functionalized phospholipid polymers via self-initiation graft polymerization.
Journal of biomaterials science. Polymer edition.
2014; 25(9):895-906. doi:
10.1080/09205063.2014.911570. [PMID: 24766535] - Zhiwen Zheng, Li Ren, Zhichen Zhai, Yingjun Wang, Fei Hang. Surface modification on polyethylene terephthalate films with 2-methacryloyloxyethyl phosphorylcholine.
Materials science & engineering. C, Materials for biological applications.
2013 Jul; 33(5):3041-6. doi:
10.1016/j.msec.2013.03.036. [PMID: 23623130] - Sean T Hemp, Adam E Smith, Joshua M Bryson, Michael H Allen, Timothy E Long. Phosphonium-containing diblock copolymers for enhanced colloidal stability and efficient nucleic acid delivery.
Biomacromolecules.
2012 Aug; 13(8):2439-45. doi:
10.1021/bm300689f. [PMID: 22713112] - Bo Yuan, Qiang Chen, Wen-Quan Ding, Ping-Sheng Liu, Shi-Shan Wu, Si-Cong Lin, Jian Shen, Yue Gai. Copolymer coatings consisting of 2-methacryloyloxyethyl phosphorylcholine and 3-methacryloxypropyl trimethoxysilane via ATRP to improve cellulose biocompatibility.
ACS applied materials & interfaces.
2012 Aug; 4(8):4031-9. doi:
10.1021/am3008399. [PMID: 22856677] - Piyaporn Akkahat, Suda Kiatkamjornwong, Shin-ichi Yusa, Voravee P Hoven, Yasuhiko Iwasaki. Development of a novel antifouling platform for biosensing probe immobilization from methacryloyloxyethyl phosphorylcholine-containing copolymer brushes.
Langmuir : the ACS journal of surfaces and colloids.
2012 Apr; 28(13):5872-81. doi:
10.1021/la204229t. [PMID: 22364521] - Yihui Xu, Anxin Dong, Yufeng Zhao, Tao Zhang, Zhengsheng Jiang, Shasha Wang, Hong Chen. Synthesis, characterization and biomedical properties of UV-cured polyurethane acrylates containing a phosphorylcholine structure.
Journal of biomaterials science. Polymer edition.
2012; 23(16):2089-104. doi:
10.1163/092050611x610315. [PMID: 22105007] - Wei Feng, Xiang Gao, Glenn McClung, Shiping Zhu, Kazuhiko Ishihara, John L Brash. Methacrylate polymer layers bearing poly(ethylene oxide) and phosphorylcholine side chains as non-fouling surfaces: in vitro interactions with plasma proteins and platelets.
Acta biomaterialia.
2011 Oct; 7(10):3692-9. doi:
10.1016/j.actbio.2011.06.007. [PMID: 21693202] - Marya Ahmed, Neha Bhuchar, Kazuhiko Ishihara, Ravin Narain. Well-controlled cationic water-soluble phospholipid polymer-DNA nanocomplexes for gene delivery.
Bioconjugate chemistry.
2011 Jun; 22(6):1228-38. doi:
10.1021/bc2001159. [PMID: 21539389] - Eiki Nagaoka, Takeshi Someya, Takashi Kitao, Taro Kimura, Tomohiro Ushiyama, Wataru Hijikata, Tadahiko Shinshi, Hirokuni Arai, Setsuo Takatani. Development of a disposable magnetically levitated centrifugal blood pump (MedTech Dispo) intended for bridge-to-bridge applications--two-week in vivo evaluation.
Artificial organs.
2010 Sep; 34(9):778-83. doi:
10.1111/j.1525-1594.2010.01107.x. [PMID: 20928936] - Masami Ukawa, Hidetaka Akita, Tomoya Masuda, Yasuhiro Hayashi, Tomohiro Konno, Kazuhiko Ishihara, Hideyoshi Harashima. 2-Methacryloyloxyethyl phosphorylcholine polymer (MPC)-coating improves the transfection activity of GALA-modified lipid nanoparticles by assisting the cellular uptake and intracellular dissociation of plasmid DNA in primary hepatocytes.
Biomaterials.
2010 Aug; 31(24):6355-62. doi:
10.1016/j.biomaterials.2010.04.031. [PMID: 20537380] - Xiao-Dan Huang, Ke Yao, Zheng Zhang, Yidong Zhang, Yao Wang. Uveal and capsular biocompatibility of an intraocular lens with a hydrophilic anterior surface and a hydrophobic posterior surface.
Journal of cataract and refractive surgery.
2010 Feb; 36(2):290-8. doi:
10.1016/j.jcrs.2009.09.027. [PMID: 20152613] - Kyoko Fukazawa, Kazuhiko Ishihara. Fabrication of a cell-adhesive protein imprinting surface with an artificial cell membrane structure for cell capturing.
Biosensors & bioelectronics.
2009 Nov; 25(3):609-14. doi:
10.1016/j.bios.2009.02.034. [PMID: 19443203] - Takeshi Someya, Mariko Kobayashi, Satoshi Waguri, Tomohiro Ushiyama, Eiki Nagaoka, Wataru Hijikata, Tadahiko Shinshi, Hirokuni Arai, Setsuo Takatani. Development of a disposable maglev centrifugal blood pump intended for one-month support in bridge-to-bridge applications: in vitro and initial in vivo evaluation.
Artificial organs.
2009 Sep; 33(9):704-13. doi:
10.1111/j.1525-1594.2009.00900.x. [PMID: 19775262] - Takashi Kandori, Toshiyuki Hayase, Kousuke Inoue, Kenichi Funamoto, Takanori Takeno, Makoto Ohta, Motohiro Takeda, Atsushi Shirai. Frictional characteristics of erythrocytes on coated glass plates subject to inclined centrifugal forces.
Journal of biomechanical engineering.
2008 Oct; 130(5):051007. doi:
10.1115/1.2948420. [PMID: 19045514] - Xiao-Dan Huang, Ke Yao, Hui Zhang, Xiao-Jun Huang, Zhi-Kang Xu. Surface modification of silicone intraocular lens by 2-methacryloyloxyethyl phosphoryl-choline binding to reduce Staphylococcus epidermidis adherence.
Clinical & experimental ophthalmology.
2007 Jul; 35(5):462-7. doi:
10.1111/j.1442-9071.2007.01516.x. [PMID: 17651252] - Masayuki Kyomoto, Yasuhiko Iwasaki, Toru Moro, Tomohiro Konno, Fumiaki Miyaji, Hiroshi Kawaguchi, Yoshio Takatori, Kozo Nakamura, Kazuhiko Ishihara. High lubricious surface of cobalt-chromium-molybdenum alloy prepared by grafting poly(2-methacryloyloxyethyl phosphorylcholine).
Biomaterials.
2007 Jul; 28(20):3121-30. doi:
10.1016/j.biomaterials.2007.03.010. [PMID: 17416412] - Dezeng Fan, Zhiyuan Jia, Xinhao Yan, Xiaolei Liu, Wei Dong, Fuyu Sun, Jian Ji, Jianping Xu, Kefeng Ren, Weidong Chen, Jiacong Shen, Hong Qiu, Runlin Gao. [Pilot study of a cell membrane like biomimetic drug-eluting coronary stent].
Sheng wu yi xue gong cheng xue za zhi = Journal of biomedical engineering = Shengwu yixue gongchengxue zazhi.
2007 Jun; 24(3):599-602. doi:
NULL. [PMID: 17713270] - Akira Saito, Tun Aung, Koji Sekiguchi, Yoshinobu Sato. Present status and perspective of the development of a bioartificial kidney for chronic renal failure patients.
Therapeutic apheresis and dialysis : official peer-reviewed journal of the International Society for Apheresis, the Japanese Society for Apheresis, the Japanese Society for Dialysis Therapy.
2006 Aug; 10(4):342-7. doi:
10.1111/j.1744-9987.2006.00387.x. [PMID: 16911187] - Shigeru Kurosawa, Miki Nakamura, Jong-Won Park, Hidenobu Aizawa, Kazunori Yamada, Mitsuo Hirata. Evaluation of a high-affinity QCM immunosensor using antibody fragmentation and 2-methacryloyloxyethyl phosphorylcholine (MPC) polymer.
Biosensors & bioelectronics.
2004 Dec; 20(6):1134-9. doi:
10.1016/j.bios.2004.05.016. [PMID: 15556359] - Jongwon Park, Shigeru Kurosawa, Junji Watanabe, Kazuhiko Ishihara. Evaluation of 2-methacryloyloxyethyl phosphorylcholine polymeric nanoparticle for immunoassay of C-reactive protein detection.
Analytical chemistry.
2004 May; 76(9):2649-55. doi:
10.1021/ac035321i. [PMID: 15117211] - Jie Chen, Young Chang Nho, Allan S Hoffman. Grafting copolymerization of 2-methacryloyloxyethyl phosphorylcholine (MPC) onto pre-irradiated cellulose films.
Journal of biomaterials science. Polymer edition.
2004; 15(7):841-9. doi:
10.1163/1568562041271138. [PMID: 15318795] - Ryo Ogawa, Yasuhiko Iwasaki, Kazuhiko Ishihara. Thermal property and processability of elastomeric polymer alloy composed of segmented polyurethane and phospholipid polymer.
Journal of biomedical materials research.
2002 Nov; 62(2):214-21. doi:
10.1002/jbm.10339. [PMID: 12209941] - Y Iwasaki, N Nakabayashi, K Ishihara. Preservation of platelet function on 2-methacryloyloxyethyl phosphorylcholine-graft polymer as compared to various water-soluble graft polymers.
Journal of biomedical materials research.
2001 Oct; 57(1):72-8. doi:
10.1002/1097-4636(200110)57:1<72::aid-jbm1143>3.0.co;2-g. [PMID: 11416851] - A Oki, S Adachi, Y Takamura, K Ishihara, H Ogawa, Y Ito, T Ichiki, Y Horiike. Electroosmosis injection of blood serum into biocompatible microcapillary chip fabricated on quartz plate.
Electrophoresis.
2001 Jan; 22(2):341-7. doi:
10.1002/1522-2683(200101)22:2<341::aid-elps341>3.0.co;2-w. [PMID: 11288903] - K Ishihara, H Fujita, T Yoneyama, Y Iwasaki. Antithrombogenic polymer alloy composed of 2-methacryloyloxyethyl phosphorylcholine polymer and segmented polyurethane.
Journal of biomaterials science. Polymer edition.
2000; 11(11):1183-95. doi:
10.1163/156856200744264. [PMID: 11263807] - S Sakaki, N Nakabayashi, K Ishihara. Stabilization of an antibody conjugated with enzyme by 2-methacryloyloxyethyl phosphorylcholine copolymer in enzyme-linked immunosorbent assay.
Journal of biomedical materials research.
1999 Dec; 47(4):523-8. doi:
10.1002/(sici)1097-4636(19991215)47:4<523::aid-jbm8>3.0.co;2-j. [PMID: 10497287] - K Ishihara, Y Iwasaki. Reduced protein adsorption on novel phospholipid polymers.
Journal of biomaterials applications.
1998 Oct; 13(2):111-27. doi:
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Journal of biomedical materials research.
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Journal of biomedical materials research.
1994 Nov; 28(11):1347-55. doi:
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Biomaterials.
1992; 13(4):235-9. doi:
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Biomaterials.
1991 Mar; 12(2):121-4. doi:
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