Phosphoramidate (BioDeep_00000840723)
代谢物信息卡片
Phosphoramidate
化学式: H2NO3P-2 (94.9772312)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: NP(=O)([O-])[O-]
InChI: InChI=1S/H4NO3P/c1-5(2,3)4/h(H4,1,2,3,4)/p-2
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)
0 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
- Małgorzata Pietrowska-Borek, Jędrzej Dobrogojski, Anna Maria Wojdyła-Mamoń, Joanna Romanowska, Justyna Gołębiewska, Sławomir Borek, Koichi Murata, Atsushi Ishihara, Maria Ángeles Pedreño, Andrzej Guranowski. Nucleoside 5'-Phosphoramidates Control the Phenylpropanoid Pathway in Vitis vinifera Suspension-Cultured Cells.
International journal of molecular sciences.
2021 Dec; 22(24):. doi:
10.3390/ijms222413567. [PMID: 34948365] - Olga A Patutina, Svetlana K Gaponova Miroshnichenko, Aleksandra V Sen'kova, Innokenty A Savin, Daniil V Gladkikh, Ekaterine A Burakova, Alesya A Fokina, Mikhail A Maslov, Elena V Shmendel', Mattew J A Wood, Valentin V Vlassov, Sidney Altman, Dmitry A Stetsenko, Marina A Zenkova. Mesyl phosphoramidate backbone modified antisense oligonucleotides targeting miR-21 with enhanced in vivo therapeutic potency.
Proceedings of the National Academy of Sciences of the United States of America.
2020 12; 117(51):32370-32379. doi:
10.1073/pnas.2016158117. [PMID: 33288723] - Dejana Jovanovic, Peter Tremmel, Pradeep S Pallan, Martin Egli, Clemens Richert. The Enzyme-Free Release of Nucleotides from Phosphoramidates Depends Strongly on the Amino Acid.
Angewandte Chemie (International ed. in English).
2020 11; 59(45):20154-20160. doi:
10.1002/anie.202008665. [PMID: 32757352] - Koji Morita, Makoto Koizumi. Synthesis of ENA Nucleotides and ENA Oligonucleotides.
Current protocols in nucleic acid chemistry.
2018 03; 72(1):4.79.1-4.79.21. doi:
10.1002/cpnc.46. [PMID: 29927121] - Sungwon Kim, Andrea Vela, Sara M Clohisey, Spiridoula Athanasiadou, Pete Kaiser, Mark P Stevens, Lonneke Vervelde. Host-specific differences in the response of cultured macrophages to Campylobacter jejuni capsule and O-methyl phosphoramidate mutants.
Veterinary research.
2018 01; 49(1):3. doi:
10.1186/s13567-017-0501-y. [PMID: 29316981] - Brittany Pequegnat, Renee M Laird, Cheryl P Ewing, Christina L Hill, Eman Omari, Frederic Poly, Mario A Monteiro, Patricia Guerry. Phase-Variable Changes in the Position of O-Methyl Phosphoramidate Modifications on the Polysaccharide Capsule of Campylobacter jejuni Modulate Serum Resistance.
Journal of bacteriology.
2017 07; 199(14):. doi:
10.1128/jb.00027-17. [PMID: 28461446] - Edward James, Fabrizio Pertusati, Andrea Brancale, Chris McGuigan. Kinase-independent phosphoramidate S1P1 receptor agonist benzyl ether derivatives.
Bioorganic & medicinal chemistry letters.
2017 03; 27(6):1371-1378. doi:
10.1016/j.bmcl.2017.02.011. [PMID: 28236593] - Mathieu Berchel, Tony Le Gall, Olivier Lozach, Jean-Pierre Haelters, Tristan Montier, Paul-Alain Jaffrès. Lipophosphoramidate-based bipolar amphiphiles: their syntheses and transfection properties.
Organic & biomolecular chemistry.
2016 Mar; 14(10):2846-53. doi:
10.1039/c5ob02512e. [PMID: 26864681] - Yuhong Liu, Fanhong Zhang, Yanyan Ru. Hyperbranched phosphoramidate-hyaluronan hybrid: a reduction-sensitive injectable hydrogel for controlled protein release.
Carbohydrate polymers.
2015 Mar; 117(?):304-311. doi:
10.1016/j.carbpol.2014.09.054. [PMID: 25498639] - Stéphanie S Le Corre, Mathieu Berchel, Nawal Belmadi, Caroline Denis, Jean-Pierre Haelters, Tony Le Gall, Pierre Lehn, Tristan Montier, Paul-Alain Jaffrès. Cationic lipophosphoramidates with two different lipid chains: synthesis and evaluation as gene carriers.
Organic & biomolecular chemistry.
2014 Mar; 12(9):1463-74. doi:
10.1039/c3ob42270d. [PMID: 24445607] - Lieke B van Alphen, Cory Q Wenzel, Michele R Richards, Christopher Fodor, Roger A Ashmus, Martin Stahl, Andrey V Karlyshev, Brendan W Wren, Alain Stintzi, William G Miller, Todd L Lowary, Christine M Szymanski. Biological roles of the O-methyl phosphoramidate capsule modification in Campylobacter jejuni.
PloS one.
2014; 9(1):e87051. doi:
10.1371/journal.pone.0087051. [PMID: 24498018] - Damien Loizeau, Tony Le Gall, Sélim Mahfoudhi, Mathieu Berchel, Alicia Maroto, Jean-Jacques Yaouanc, Paul-Alain Jaffrès, Pierre Lehn, Laure Deschamps, Tristan Montier, Philippe Giamarchi. Physicochemical properties of cationic lipophosphoramidates with an arsonium head group and various lipid chains: A structure-activity approach.
Biophysical chemistry.
2013 Jan; 171(?):46-53. doi:
10.1016/j.bpc.2012.10.003. [PMID: 23182464] - Peiyuan Wang, Suguna Rachakonda, Veronique Zennou, Meg Keilman, Congrong Niu, Donghui Bao, Bruce S Ross, Phillip A Furman, Michael J Otto, Michael J Sofia. Phosphoramidate prodrugs of (-)-β-D-(2R,4R)-dioxolane-thymine (DOT) as potent anti-HIV agents.
Antiviral chemistry & chemotherapy.
2012 May; 22(5):217-38. doi:
10.3851/imp2079. [PMID: 22358223] - Aurore Fraix, Tristan Montier, Tony Le Gall, Charlotte M Sevrain, Nathalie Carmoy, Mattias F Lindberg, Pierre Lehn, Paul-Alain Jaffrès. Lipothiophosphoramidates for gene delivery: critical role of the cationic polar headgroup.
Organic & biomolecular chemistry.
2012 Mar; 10(10):2051-8. doi:
10.1039/c2ob06812e. [PMID: 22293653] - Mathieu Berchel, Tony Le Gall, Hélène Couthon-Gourvès, Jean-Pierre Haelters, Tristan Montier, Patrick Midoux, Pierre Lehn, Paul-Alain Jaffrès. Lipophosphonate/lipophosphoramidates: a family of synthetic vectors efficient for gene delivery.
Biochimie.
2012 Jan; 94(1):33-41. doi:
10.1016/j.biochi.2011.07.026. [PMID: 21840369] - Masataka Nakanishi, Rajesh Patil, Yong Ren, Rishab Shyam, Philip Wong, Hai Quan Mao. Enhanced stability and knockdown efficiency of poly(ethylene glycol)-b-polyphosphoramidate/siRNA micellar nanoparticles by co-condensation with sodium triphosphate.
Pharmaceutical research.
2011 Jul; 28(7):1723-1732. doi:
10.1007/s11095-011-0408-7. [PMID: 21387148] - Xuan Jiang, Derek Leong, Yong Ren, Zhiping Li, Michael S Torbenson, Hai-Quan Mao. String-like micellar nanoparticles formed by complexation of PEG-b-PPA and plasmid DNA and their transfection efficiency.
Pharmaceutical research.
2011 Jun; 28(6):1317-27. doi:
10.1007/s11095-011-0436-3. [PMID: 21499836] - John H Vernachio, Blair Bleiman, K Dawn Bryant, Stanley Chamberlain, Damound Hunley, Jeff Hutchins, Brenda Ames, Elena Gorovits, Babita Ganguly, Andrea Hall, Alexander Kolykhalov, Yule Liu, Jerry Muhammad, Nicholas Raja, C Robin Walters, Jin Wang, Karen Williams, Joseph M Patti, Geoffrey Henson, Karolina Madela, Mohamed Aljarah, Arnaud Gilles, Christopher McGuigan. INX-08189, a phosphoramidate prodrug of 6-O-methyl-2'-C-methyl guanosine, is a potent inhibitor of hepatitis C virus replication with excellent pharmacokinetic and pharmacodynamic properties.
Antimicrobial agents and chemotherapy.
2011 May; 55(5):1843-51. doi:
10.1128/aac.01335-10. [PMID: 21357300] - Christopher McGuigan, Arnaud Gilles, Karolina Madela, Mohamed Aljarah, Sabrina Holl, Sarah Jones, John Vernachio, Jeff Hutchins, Brenda Ames, K Dawn Bryant, Elena Gorovits, Babita Ganguly, Damound Hunley, Andrea Hall, Alexander Kolykhalov, Yule Liu, Jerry Muhammad, Nicholas Raja, Robin Walters, Jin Wang, Stanley Chamberlain, Geoffrey Henson. Phosphoramidate ProTides of 2'-C-methylguanosine as highly potent inhibitors of hepatitis C virus. Study of their in vitro and in vivo properties.
Journal of medicinal chemistry.
2010 Jul; 53(13):4949-57. doi:
10.1021/jm1003792. [PMID: 20527890] - Sergei M Gryaznov. Oligonucleotide n3'-->p5' phosphoramidates and thio-phoshoramidates as potential therapeutic agents.
Chemistry & biodiversity.
2010 Mar; 7(3):477-93. doi:
10.1002/cbdv.200900187. [PMID: 20232321] - Tony Le Gall, Damien Loizeau, Erwan Picquet, Nathalie Carmoy, Jean-Jacques Yaouanc, Laure Burel-Deschamps, Pascal Delépine, Philippe Giamarchi, Paul-Alain Jaffrès, Pierre Lehn, Tristan Montier. A novel cationic lipophosphoramide with diunsaturated lipid chains: synthesis, physicochemical properties, and transfection activities.
Journal of medicinal chemistry.
2010 Feb; 53(4):1496-508. doi:
10.1021/jm900897a. [PMID: 20112994] - Suzanne E Lapi, Hilla Wahnishe, David Pham, Lisa Y Wu, Jessie R Nedrow-Byers, Tiancheng Liu, Kaveh Vejdani, Henry F VanBrocklin, Clifford E Berkman, Ella F Jones. Assessment of an 18F-labeled phosphoramidate peptidomimetic as a new prostate-specific membrane antigen-targeted imaging agent for prostate cancer.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine.
2009 Dec; 50(12):2042-8. doi:
10.2967/jnumed.109.066589. [PMID: 19910433] - Khodayar Gholivand, Mohammad Abdollahi, Fresia Mojahed, Ahlam Madani Alizadehgan, Gholamreza Dehghan. Acetylcholinesterase/butyrylcholinesterase inhibition activity of some new carbacylamidophosphate derivatives.
Journal of enzyme inhibition and medicinal chemistry.
2009 Apr; 24(2):566-76. doi:
10.1080/14756360802316971. [PMID: 18825527] - Z Gunnur Dikmen, Woodring E Wright, Jerry W Shay, Sergei M Gryaznov. Telomerase targeted oligonucleotide thio-phosphoramidates in T24-luc bladder cancer cells.
Journal of cellular biochemistry.
2008 May; 104(2):444-52. doi:
10.1002/jcb.21635. [PMID: 18044713] - Mayumi Takahashi, Noriaki Minakawa, Akira Matsuda. Synthesis and properties of 2'-modified-4'-thioRNA.
Nucleic acids symposium series (2004).
2008; ?(52):327-8. doi:
10.1093/nass/nrn165. [PMID: 18776386] - Shalmica R Jackson, Chun-Hong Zhu, Vera Paulson, Linda Watkins, Z Gunnur Dikmen, Sergei M Gryaznov, Woodring E Wright, Jerry W Shay. Antiadhesive effects of GRN163L--an oligonucleotide N3'->P5' thio-phosphoramidate targeting telomerase.
Cancer research.
2007 Feb; 67(3):1121-9. doi:
10.1158/0008-5472.can-06-2306. [PMID: 17283146] - Yuzeng Liang, Janarthanan Narayanasamy, Raymond F Schinazi, Chung K Chu. Phosphoramidate and phosphate prodrugs of (-)-beta-D-(2R,4R)-dioxolane-thymine: synthesis, anti-HIV activity and stability studies.
Bioorganic & medicinal chemistry.
2006 Apr; 14(7):2178-89. doi:
10.1016/j.bmc.2005.11.008. [PMID: 16314108] - Carmen Almansa, Javier Bartrolí, Jordi Belloc, Fernando L Cavalcanti, Rosa Ferrando, Luis A Gómez, Isabel Ramis, Elena Carceller, Manuel Merlos, Julián García-Rafanell. New water-soluble sulfonylphosphoramidic acid derivatives of the COX-2 selective inhibitor cimicoxib. A novel approach to sulfonamide prodrugs.
Journal of medicinal chemistry.
2004 Oct; 47(22):5579-82. doi:
10.1021/jm040844j. [PMID: 15481993] - Dario Siccardi, Mark Gumbleton, Yadollah Omidi, Chistopher McGuigan. Stereospecific chemical and enzymatic stability of phosphoramidate triester prodrugs of d4T in vitro.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.
2004 May; 22(1):25-31. doi:
10.1016/j.ejps.2004.02.006. [PMID: 15113580] - Ahmed M Awad, Michal Sobkowski, Hartmut Seliger. Enzymatic and hybridization properties of oligonucleotide analogs containing novel phosphoramidate internucleotide linkages.
Nucleosides, nucleotides & nucleic acids.
2004 May; 23(5):777-87. doi:
10.1081/ncn-120039357. [PMID: 15281366] - Nguyen-Hai Nam, Rebecca L Pitts, Gongqin Sun, Soroush Sardari, Amie Tiemo, Mingxing Xie, Bingfang Yan, Keykavous Parang. Design of tetrapeptide ligands as inhibitors of the Src SH2 domain.
Bioorganic & medicinal chemistry.
2004 Feb; 12(4):779-87. doi:
10.1016/j.bmc.2003.10.060. [PMID: 14759738] - Dario Siccardi, Lana E Kandalaft, Mark Gumbleton, Christopher McGuigan. Stereoselective and concentration-dependent polarized epithelial permeability of a series of phosphoramidate triester prodrugs of d4T: an in vitro study in Caco-2 and Madin-Darby canine kidney cell monolayers.
The Journal of pharmacology and experimental therapeutics.
2003 Dec; 307(3):1112-9. doi:
10.1124/jpet.103.056135. [PMID: 14557377] - Brittney-Shea Herbert, Krisztina Pongracz, Jerry W Shay, Sergei M Gryaznov, Brittney Shea-Herbert. Oligonucleotide N3'-->P5' phosphoramidates as efficient telomerase inhibitors.
Oncogene.
2002 Jan; 21(4):638-42. doi:
10.1038/sj.onc.1205064. [PMID: 11850790] - E J McIntee, C R Wagner. Amino acid phosphoramidate nucleosides: potential ADEPT/GDEPT substrates.
Bioorganic & medicinal chemistry letters.
2001 Nov; 11(21):2803-5. doi:
10.1016/s0960-894x(01)00513-3. [PMID: 11597404] - K S Tanaka, X Y Chen, Y Ichikawa, P C Tyler, R H Furneaux, V L Schramm. Ricin A-chain inhibitors resembling the oxacarbenium ion transition state.
Biochemistry.
2001 Jun; 40(23):6845-51. doi:
10.1021/bi010499p. [PMID: 11389598] - T Lynch, G Eisenberg, M Kernan. LC/MS determination of the intracellular concentration of two novel aryl phosphoramidate prodrugs of PMPA and their metabolites in dog PBMC.
Nucleosides, nucleotides & nucleic acids.
2001 Apr; 20(4-7):1415-9. doi:
10.1081/ncn-100002567. [PMID: 11563034] - J T Hwang, M M Greenberg. Synthesis of 2'-modified oligodeoxynucleotides via on-column conjugation.
The Journal of organic chemistry.
2001 Jan; 66(2):363-9. doi:
10.1021/jo000917g. [PMID: 11429801] - C R Wagner, V V Iyer, E J McIntee. Pronucleotides: toward the in vivo delivery of antiviral and anticancer nucleotides.
Medicinal research reviews.
2000 Nov; 20(6):417-51. doi:
10.1002/1098-1128(200011)20:6<417::aid-med1>3.0.co;2-z. [PMID: 11058891] - L Wang, S Gryaznov, M Nerenberg. Inhibition of IL-6 in mice by anti-NF-kappaB oligodeoxyribonucleotide N3'-->oligodeoxyribonnucleotide N3' --> P5' phosphoramidates.
Inflammation.
1999 Dec; 23(6):583-90. doi:
10.1023/a:1020298608675. [PMID: 10565571] - V Gilard, R Martino, M Malet-Martino, U Niemeyer, J Pohl. Chemical stability and fate of the cytostatic drug ifosfamide and its N-dechloroethylated metabolites in acidic aqueous solutions.
Journal of medicinal chemistry.
1999 Jul; 42(14):2542-60. doi:
10.1021/jm980587g. [PMID: 10411475] - K B Lesiak, B Uznanski, P F Torrence. The solid-phase synthesis of 2'-5'-linked oligoriboadenylates containing 8-bromoadenine.
Applied biochemistry and biotechnology.
1997 Jul; 67(1-2):33-44. doi:
10.1007/bf02787839. [PMID: 9382489] - R Alul, G D Hoke. (2'-5')-Oligo-3'-deoxynucleotides: selective binding to single-stranded RNA but not DNA.
Antisense research and development.
1995; 5(1):3-11. doi:
10.1089/ard.1995.5.3. [PMID: 7542046] - A Boumendjel, S P Miller. Synthesis of sphingosine-1-phosphate and dihydrosphingosine-1-phosphate.
Journal of lipid research.
1994 Dec; 35(12):2305-11. doi:
10.1016/s0022-2275(20)39936-3. [PMID: 7897327]