Cytidine monophosphate (BioDeep_00000002971)

 

Secondary id: BioDeep_00000398706, BioDeep_00000398707, BioDeep_00000400069, BioDeep_00000405199, BioDeep_00001868128

natural product human metabolite PANOMIX_OTCML-2023 Endogenous BioNovoGene_Lab2019 Volatile Flavor Compounds


代谢物信息卡片


{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

化学式: C9H14N3O8P (323.05184940000004)
中文名称: 聚胞苷酸, 5'-胞苷酸, 胞苷-5磷酸, 胞苷酸
谱图信息: 最多检出来源 Homo sapiens(feces) 0.08%

分子结构信息

SMILES: C1=CN(C(=O)N=C1N)C2C(C(C(O2)COP(=O)(O)O)O)O
InChI: InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)

描述信息

Cytidine monophosphate, also known as 5-cytidylic acid and abbreviated CMP, is a nucleotide. It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine. Cytidine monophosphate (CMP) is derived from cytidine triphosphate (CTP) with subsequent loss of two phosphates. The synthesis of the pyrimidines CTP and UTP occurs in the cytoplasm and starts with the formation of carbamoyl phosphate from glutamine and CO2. Next, aspartate undergoes a condensation reaction with carbamoyl-phosphate to form orotic acid. In a subsequent cyclization reaction, the enzyme Aspartate carbamoyltransferase forms N-carbamoyl-aspartate which is converted into dihydroorotic acid by Dihydroorotase. The latter is converted to orotate by Dihydroorotate oxidase. Orotate is covalently linked with a phosphorylated ribosyl unit with Orotate phosphoribosyltransferase (aka "PRPP transferase") catalyzing reaction, yielding orotidine monophosphate (OMP). Orotidine-5-phosphate is decarboxylated by Orotidine-5-phosphate decarboxylase to form uridine monophosphate (UMP). UMP is phosphorylated by two kinases to uridine triphosphate (UTP) via two sequential reactions with ATP. CTP is subsequently formed by amination of UTP by the catalytic activity of CTP synthetase. Cytosine monophosphate (CMP) and uridine monophosphate (UMP) have been prescribed for the treatment of neuromuscular affections in humans. Patients treated with CMP/UMP recover from altered neurological functions. Additionally, the administration of CMP/UMP appears to favour the entry of glucose in the muscle and CMP/UMP may be important in maintaining the level of hepatic glycogen constant during exercise. [PMID:18663991].
Cytidine monophosphate, also known as cmp or cytidylic acid, is a member of the class of compounds known as pyrimidine ribonucleoside monophosphates. Pyrimidine ribonucleoside monophosphates are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. Cytidine monophosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Cytidine monophosphate can be found in a number of food items such as elliotts blueberry, small-leaf linden, orange mint, and malabar spinach, which makes cytidine monophosphate a potential biomarker for the consumption of these food products. Cytidine monophosphate can be found primarily in saliva, as well as throughout all human tissues. Cytidine monophosphate exists in all living species, ranging from bacteria to humans. In humans, cytidine monophosphate is involved in several metabolic pathways, some of which include cardiolipin biosynthesis cl(i-13:0/i-18:0/i-17:0/18:2(9z,11z)), cardiolipin biosynthesis cl(i-13:0/i-24:0/a-21:0/i-15:0), cardiolipin biosynthesis cl(i-13:0/i-22:0/i-20:0/i-15:0), and cardiolipin biosynthesis cl(i-12:0/a-17:0/i-20:0/a-21:0). Cytidine monophosphate is also involved in several metabolic disorders, some of which include beta ureidopropionase deficiency, MNGIE (mitochondrial neurogastrointestinal encephalopathy), UMP synthase deficiency (orotic aciduria), and dihydropyrimidinase deficiency.
Acquisition and generation of the data is financially supported in part by CREST/JST.
COVID info from WikiPathways
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
Cytidine 5'-monophosphate (5'-Cytidylic acid) is a nucleotide which is used as a monomer in RNA. Cytidine 5'-monophosphate consists of the nucleobase cytosine, the pentose sugar ribose, and the phosphate group[1].
Cytidine 5'-monophosphate (5'-Cytidylic acid) is a nucleotide which is used as a monomer in RNA. Cytidine 5'-monophosphate consists of the nucleobase cytosine, the pentose sugar ribose, and the phosphate group[1].

同义名列表

38 个代谢物同义名

{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid; Cytidine-5-monophosphate disodium salt,from Saccharomyces cerevisiae, crystalline; Cytidine-5-monophosphate monohydrate; Cytidine mono(dihydrogen phosphate); Cytosine arabinoside monophosphate; Cytidine 5’-monophosphoric acid; Cytidine 5-monophosphoric acid; Cytidine-5-monophosphoric acid; 5-Cytidylic acid, homopolymer; Cytidine monophosphoric acid; Cytidine 5’-phosphoric acid; Cytidine 5-monophosphorate; Cytidine 5-phosphoric acid; Cytidine 5’-monophosphate; Cytosine 5’-monophosphate; Cytosine 5-monophosphate; Cytidine 5-monophosphate; Cytidine-5-monophosphate; monoPhosphate, cytidine; Cytidine 5-phosphorate; Cytidine monophosphate; Cytidine 5’-phosphate; Cytidine 5-phosphate; 5-Cytidylic acid; Acid, cytidylic; Cytidylic acid; 5-Cytidylate; Cytidylate; 5’-CMP; 5-CMP; C-5-P; CMP; pC; Cytidine monophosphate(CMP); 5'-Cytidylic acid; 5'-CMP; Cytidine 5'-monophosphate; CMP



数据库引用编号

59 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(3)

BioCyc(4)

PlantCyc(0)

代谢反应

34958 个相关的代谢反应过程信息。

Reactome(39)

BioCyc(14)

WikiPathways(0)

Plant Reactome(388)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(1)

PathBank(34514)

PharmGKB(0)

44 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

  • Abhijeet Lokras, Akash Chakravarty, Thomas Rades, Dennis Christensen, Henrik Franzyk, Aneesh Thakur, Camilla Foged. Simultaneous quantification of multiple RNA cargos co-loaded into nanoparticle-based delivery systems. International journal of pharmaceutics. 2022 Oct; 626(?):122171. doi: 10.1016/j.ijpharm.2022.122171. [PMID: 36070841]
  • Zhiwei Han, Yuanqiang Zhu, Jingji Xu, Didi Wen, Yuwei Xia, Minwen Zheng, Tao Yan, Mengqi Wei. Predictive Value of CT-Based Radiomics in Distinguishing Renal Angiomyolipomas with Minimal Fat from Other Renal Tumors. Disease markers. 2022; 2022(?):9108129. doi: 10.1155/2022/9108129. [PMID: 35669501]
  • Dániel Szőke, Gábor Kovács, Éva Kemecsei, László Bálint, Kitti Szoták-Ajtay, Petra Aradi, Andrea Styevkóné Dinnyés, Barbara L Mui, Ying K Tam, Thomas D Madden, Katalin Karikó, Raghu P Kataru, Michael J Hope, Drew Weissman, Babak J Mehrara, Norbert Pardi, Zoltán Jakus. Nucleoside-modified VEGFC mRNA induces organ-specific lymphatic growth and reverses experimental lymphedema. Nature communications. 2021 06; 12(1):3460. doi: 10.1038/s41467-021-23546-6. [PMID: 34103491]
  • Farasat Kazmi, Shibani Nicum, Rene L Roux, Laura Spiers, Chat Gnanaranjan, Ajithkumar Sukumaran, Hani Gabra, Essam Ghazaly, Nigel W McCracken, David J Harrison, Sarah P Blagden. A Phase Ib Open-Label, Dose-Escalation Study of NUC-1031 in Combination with Carboplatin for Recurrent Ovarian Cancer. Clinical cancer research : an official journal of the American Association for Cancer Research. 2021 06; 27(11):3028-3038. doi: 10.1158/1078-0432.ccr-20-4403. [PMID: 33741651]
  • Mairéad G McNamara, John Bridgewater, Daniel H Palmer, Olusola Faluyi, Harpreet Wasan, Alkesh Patel, William D Ryder, Safia Barber, Chathunissa Gnanaranjan, Essam Ghazaly, T R Jeff Evans, Juan W Valle. A Phase Ib Study of NUC-1031 in Combination with Cisplatin for the First-Line Treatment of Patients with Advanced Biliary Tract Cancer (ABC-08). The oncologist. 2021 04; 26(4):e669-e678. doi: 10.1002/onco.13598. [PMID: 33210382]
  • Soo Jin Oh, Ok Sarah Shin. SARS-CoV-2 Nucleocapsid Protein Targets RIG-I-Like Receptor Pathways to Inhibit the Induction of Interferon Response. Cells. 2021 03; 10(3):. doi: 10.3390/cells10030530. [PMID: 33801464]
  • Sandrine Bonneton, Isabelle Maillard, Frédéric Denis, Jean-Luc Roelandt. Title Not Available. Sante publique (Vandoeuvre-les-Nancy, France). 2021; 32(5):531-535. doi: 10.3917/spub.205.0531. [PMID: 35724169]
  • Paul Kwangho Kwon, Kyung-Ha Lee, Ji-Hyung Kim, Sookil Tae, Seokjin Ham, Young-Hun Jeong, Sung Wook Kim, Byunghee Kang, Hyo-Min Kim, Jung-Hyun Choi, Hee Yi, Hyun-Ok Ku, Tae-Young Roh, Chunghun Lim, Kyong-Tai Kim. hnRNP K Supports High-Amplitude D Site-Binding Protein mRNA (Dbp mRNA) Oscillation To Sustain Circadian Rhythms. Molecular and cellular biology. 2020 02; 40(6):. doi: 10.1128/mcb.00537-19. [PMID: 31907279]
  • Wufan Pan, Dongdong Yu, Yazhou Qin, Wanghua Wu, Yuxiang Lu, Zhen Yuan, Jianguang Zhou. Aligner mediated cleavage of nucleic acids for site-specific detection of single base mismatch. Talanta. 2019 Aug; 201(?):358-363. doi: 10.1016/j.talanta.2019.03.106. [PMID: 31122435]
  • Mingshu Xiao, Arun Richard Chandrasekaran, Wei Ji, Fan Li, Tiantian Man, Changfeng Zhu, Xizhong Shen, Hao Pei, Qian Li, Li Li. Affinity-Modulated Molecular Beacons on MoS2 Nanosheets for MicroRNA Detection. ACS applied materials & interfaces. 2018 Oct; 10(42):35794-35800. doi: 10.1021/acsami.8b14035. [PMID: 30277380]
  • Ben A Wagstaff, Martin Rejzek, Robert A Field. Identification of a Kdn biosynthesis pathway in the haptophyte Prymnesium parvum suggests widespread sialic acid biosynthesis among microalgae. The Journal of biological chemistry. 2018 10; 293(42):16277-16290. doi: 10.1074/jbc.ra118.004921. [PMID: 30171074]
  • Jing Chen, Jin Li, Jensen H C Yiu, Jenny K W Lam, Chi-Ming Wong, Bernhard Dorweiler, Aimin Xu, Connie W Woo. TRIF-dependent Toll-like receptor signaling suppresses Scd1 transcription in hepatocytes and prevents diet-induced hepatic steatosis. Science signaling. 2017 Aug; 10(491):. doi: 10.1126/scisignal.aal3336. [PMID: 28790196]
  • Sunita Gulati, Ian C Schoenhofen, Dennis M Whitfield, Andrew D Cox, Jianjun Li, Frank St Michael, Evgeny V Vinogradov, Jacek Stupak, Bo Zheng, Makoto Ohnishi, Magnus Unemo, Lisa A Lewis, Rachel E Taylor, Corinna S Landig, Sandra Diaz, George W Reed, Ajit Varki, Peter A Rice, Sanjay Ram. Utilizing CMP-Sialic Acid Analogs to Unravel Neisseria gonorrhoeae Lipooligosaccharide-Mediated Complement Resistance and Design Novel Therapeutics. PLoS pathogens. 2015 Dec; 11(12):e1005290. doi: 10.1371/journal.ppat.1005290. [PMID: 26630657]
  • Sathnur Pushpakumar, Sourav Kundu, Nithya Narayanan, Utpal Sen. DNA hypermethylation in hyperhomocysteinemia contributes to abnormal extracellular matrix metabolism in the kidney. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2015 Nov; 29(11):4713-25. doi: 10.1096/fj.15-272443. [PMID: 26224753]
  • Paola Rota, Federica Cirillo, Marco Piccoli, Antonio Gregorio, Guido Tettamanti, Pietro Allevi, Luigi Anastasia. Synthesis and biological evaluation of several dephosphonated analogues of CMP-Neu5Ac as inhibitors of GM3-synthase. Chemistry (Weinheim an der Bergstrasse, Germany). 2015 Oct; 21(41):14614-29. doi: 10.1002/chem.201501770. [PMID: 26397189]
  • Mariam Ayub, David Stoddart, Hagan Bayley. Nucleobase Recognition by Truncated α-Hemolysin Pores. ACS nano. 2015 Aug; 9(8):7895-903. doi: 10.1021/nn5060317. [PMID: 26114210]
  • Zi Li, Soyoun Hwang, Jaime Ericson, Kyle Bowler, Maor Bar-Peled. Pen and Pal are nucleotide-sugar dehydratases that convert UDP-GlcNAc to UDP-6-deoxy-D-GlcNAc-5,6-ene and then to UDP-4-keto-6-deoxy-L-AltNAc for CMP-pseudaminic acid synthesis in Bacillus thuringiensis. The Journal of biological chemistry. 2015 Jan; 290(2):691-704. doi: 10.1074/jbc.m114.612747. [PMID: 25414257]
  • Ai-hua Zhang, Hui Sun, Shi Qiu, Xi-jun Wang. Metabolomics in noninvasive breast cancer. Clinica chimica acta; international journal of clinical chemistry. 2013 Sep; 424(?):3-7. doi: 10.1016/j.cca.2013.05.003. [PMID: 23669185]
  • Carmen Eicher, Alexander Dewerth, Verena Ellerkamp, Joerg Fuchs, Sarah Schott, Sorin Armeanu-Ebinger. Effect of duplex drugs linking 2'-deoxy-5-fluorouridine (5-FdU) with 3'-C-ethynylcytidine (ECyd) on hepatoblastoma cell lines. Pediatric surgery international. 2013 Feb; 29(2):121-7. doi: 10.1007/s00383-012-3192-5. [PMID: 23187893]
  • Sarah Schott, Heike Niessner, Tobias Sinnberg, Sascha Venturelli, Alexander Berger, Kristian Ikenberg, Jessie Villanueva, Friedegund Meier, Claus Garbe, Christian Busch. Cytotoxicity of new duplex drugs linking 3'-C-ethynylcytidine and 5-fluor-2'-deoxyuridine against human melanoma cells. International journal of cancer. 2012 Nov; 131(9):2165-74. doi: 10.1002/ijc.27476. [PMID: 22323315]
  • F Lecomte, C Hubert, S Demarche, C De Bleye, A Dispas, M Jost, F Frankenne, A Ceccato, E Rozet, Ph Hubert. Comparison of the quantitative performances and measurement uncertainty estimates obtained during method validation versus routine applications of a novel hydrophilic interaction chromatography method for the determination of cidofovir in human plasma. Journal of pharmaceutical and biomedical analysis. 2012 Jan; 57(?):153-65. doi: 10.1016/j.jpba.2011.08.040. [PMID: 21959349]
  • Jae Suk Kim, James R Beadle, William R Freeman, Karl Y Hostetler, Kathrin Hartmann, Nadejda Valiaeva, Igor Kozak, Laura Conner, Julissa Trahan, Kathy A Aldern, Lingyun Cheng. A novel cytarabine crystalline lipid prodrug: hexadecyloxypropyl cytarabine 3',5'-cyclic monophosphate for proliferative vitreoretinopathy. Molecular vision. 2012; 18(?):1907-17. doi: . [PMID: 22876115]
  • Chiguang Feng, Nicholas M Stamatos, Anatoliy I Dragan, Andrei Medvedev, Melissa Whitford, Lei Zhang, Chang Song, Prasad Rallabhandi, Leah Cole, Quan M Nhu, Stefanie N Vogel, Chris D Geddes, Alan S Cross. Sialyl residues modulate LPS-mediated signaling through the Toll-like receptor 4 complex. PloS one. 2012; 7(4):e32359. doi: 10.1371/journal.pone.0032359. [PMID: 22496731]
  • Ozge Guldali, Vahide Savci, Kansu Buyukafsar. CDP-choline-induced contractions in the mouse gastric fundus through purinoceptors and Rho/Rho-kinase signalling. Life sciences. 2011 Mar; 88(11-12):473-9. doi: 10.1016/j.lfs.2011.01.002. [PMID: 21219915]
  • Sebanti Roy Chowdhury, Md Maidul Islam, Gopinatha Suresh Kumar. Binding of the anticancer alkaloid sanguinarine to double stranded RNAs: insights into the structural and energetics aspects. Molecular bioSystems. 2010 Jul; 6(7):1265-76. doi: 10.1039/b927001a. [PMID: 20442937]
  • Alexandra Castilho, Richard Strasser, Johannes Stadlmann, Josephine Grass, Jakub Jez, Pia Gattinger, Renate Kunert, Heribert Quendler, Martin Pabst, Renaud Leonard, Friedrich Altmann, Herta Steinkellner. In planta protein sialylation through overexpression of the respective mammalian pathway. The Journal of biological chemistry. 2010 May; 285(21):15923-30. doi: 10.1074/jbc.m109.088401. [PMID: 20305285]
  • Martial Séveno, Emilie Séveno-Carpentier, Aline Voxeur, Laurence Menu-Bouaouiche, Christophe Rihouey, Frédéric Delmas, Christian Chevalier, Azeddine Driouich, Patrice Lerouge. Characterization of a putative 3-deoxy-D-manno-2-octulosonic acid (Kdo) transferase gene from Arabidopsis thaliana. Glycobiology. 2010 May; 20(5):617-28. doi: 10.1093/glycob/cwq011. [PMID: 20124190]
  • Ryo Misaki, Hiroyuki Kajiura, Kenji Fujii, Kazuhito Fujiyama, Tatsuji Seki. Cloning and characterization of cytidine monophosphate-3-deoxy-d-manno-octulosonate synthetase from Arabidopsis thaliana. Journal of bioscience and bioengineering. 2009 Dec; 108(6):527-9. doi: 10.1016/j.jbiosc.2009.05.022. [PMID: 19914588]
  • Makoto Ogata, Makoto Nakajima, Tatsuya Kato, Takakiyo Obara, Hirokazu Yagi, Koichi Kato, Taichi Usui, Enoch Y Park. Synthesis of sialoglycopolypeptide for potentially blocking influenza virus infection using a rat alpha2,6-sialyltransferase expressed in BmNPV bacmid-injected silkworm larvae. BMC biotechnology. 2009 Jun; 9(?):54. doi: 10.1186/1472-6750-9-54. [PMID: 19500344]
  • Sandra L Diaz, Vered Padler-Karavani, Darius Ghaderi, Nancy Hurtado-Ziola, Hai Yu, Xi Chen, Els C M Brinkman-Van der Linden, Ajit Varki, Nissi M Varki. Sensitive and specific detection of the non-human sialic Acid N-glycolylneuraminic acid in human tissues and biotherapeutic products. PloS one. 2009; 4(1):e4241. doi: 10.1371/journal.pone.0004241. [PMID: 19156207]
  • Linghua Zhang, Meirong Zhang, Jiaoqing Li, Ting Cao, Xingshan Tian, Fengzhen Zhou. Enhancement of mucosal immune responses by intranasal co-delivery of Newcastle disease vaccine plus CpG oligonucleotide in SPF chickens in vivo. Research in veterinary science. 2008 Dec; 85(3):495-502. doi: 10.1016/j.rvsc.2008.02.006. [PMID: 18359498]
  • Yong-Xin Ru, Shi-Xuan Zhao, Jin-Hua Liu, Yin-Chang Mi, Xiao-Fan Zhu, Tian-Xiang Pang. [Ultrastructural analysis of 5' nucleotides distribution in acute myeloid leukemia subtypes]. Zhongguo shi yan xue ye xue za zhi. 2008 Jun; 16(3):484-7. doi: . [PMID: 18549613]
  • Akira Horikoshi, Kazuhiro Takei, Yoshifumi Hosokawa, Shigemasa Sawada. The value of oral cytarabine ocfosfate and etoposide in the treatment of refractory and elderly AML patients. International journal of hematology. 2008 Mar; 87(2):118-125. doi: 10.1007/s12185-007-0019-6. [PMID: 18228114]
  • Yesim Ozarda Ilcol, Mehmet Cansev, Mustafa Sertac Yilmaz, Emre Hamurtekin, Ismail H Ulus. Peripheral administration of CDP-choline and its cholinergic metabolites increases serum insulin: muscarinic and nicotinic acetylcholine receptors are both involved in their actions. Neuroscience letters. 2008 Jan; 431(1):71-6. doi: 10.1016/j.neulet.2007.11.024. [PMID: 18162319]
  • M Cansev, Y O Ilcol, M S Yilmaz, E Hamurtekin, I H Ulus. Peripheral administration of CDP-choline, phosphocholine or choline increases plasma adrenaline and noradrenaline concentrations. Autonomic & autacoid pharmacology. 2008 Jan; 28(1):41-58. doi: 10.1111/j.1474-8673.2007.00416.x. [PMID: 18257750]
  • Mehmet Cansev, Mustafa Sertac Yilmaz, Yesim Ozarda Ilcol, Emre Hamurtekin, Ismail Hakki Ulus. Cardiovascular effects of CDP-choline and its metabolites: involvement of peripheral autonomic nervous system. European journal of pharmacology. 2007 Dec; 577(1-3):129-42. doi: 10.1016/j.ejphar.2007.08.029. [PMID: 17884041]
  • Atanas Kamburov, Leon Goldovsky, Shiri Freilich, Aliki Kapazoglou, Victor Kunin, Anton J Enright, Athanasios Tsaftaris, Christos A Ouzounis. Denoising inferred functional association networks obtained by gene fusion analysis. BMC genomics. 2007 Dec; 8(?):460. doi: 10.1186/1471-2164-8-460. [PMID: 18081932]
  • Y O Ilcol, M Cansev, M S Yilmaz, E Hamurtekin, I H Ulus. Intraperitoneal administration of CDP-choline and its cholinergic and pyrimidinergic metabolites induce hyperglycemia in rats: involvement of the sympathoadrenal system. Archives of physiology and biochemistry. 2007 Oct; 113(4-5):186-201. doi: 10.1080/13813450701531243. [PMID: 17917852]
  • Serge H Boyer, Zhili Sun, Hongjian Jiang, Julie Esterbrook, Jorge E Gómez-Galeno, William Craigo, K Raja Reddy, Bheemarao G Ugarkar, Deidre A MacKenna, Mark D Erion. Synthesis and characterization of a novel liver-targeted prodrug of cytosine-1-beta-D-arabinofuranoside monophosphate for the treatment of hepatocellular carcinoma. Journal of medicinal chemistry. 2006 Dec; 49(26):7711-20. doi: 10.1021/jm0607449. [PMID: 17181153]
  • Mads Gabrielsen, Johannes Kaiser, Felix Rohdich, Wolfgang Eisenreich, Ralf Laupitz, Adelbert Bacher, Charles S Bond, William N Hunter. The crystal structure of a plant 2C-methyl-D-erythritol 4-phosphate cytidylyltransferase exhibits a distinct quaternary structure compared to bacterial homologues and a possible role in feedback regulation for cytidine monophosphate. The FEBS journal. 2006 Mar; 273(5):1065-73. doi: 10.1111/j.1742-4658.2006.05133.x. [PMID: 16478479]
  • Jianqi Yang, Colleen M Croniger, Julie Lekstrom-Himes, Pu Zhang, Maris Fenyus, Daniel G Tenen, Gretchen J Darlington, Richard W Hanson. Metabolic response of mice to a postnatal ablation of CCAAT/enhancer-binding protein alpha. The Journal of biological chemistry. 2005 Nov; 280(46):38689-99. doi: 10.1074/jbc.m503486200. [PMID: 16166091]
  • Yukinobu Uchiyama, Junko Tagami, Shinji Kamisuki, Nobuyuki Kasai, Masahiko Oshige, Hiroyuki Chiku, Siroh Ibe, Osamu Koiwai, Fumio Sugawara, Kengo Sakaguchi. Selective inhibitors of terminal deoxyribonucleotidyltransferase (TdT): baicalin and genistin. Biochimica et biophysica acta. 2005 Oct; 1725(3):298-304. doi: 10.1016/j.bbagen.2005.06.017. [PMID: 16099107]
  • Zhongjun Dong, Haiming Wei, Rui Sun, Zhiqing Hu, Bin Gao, Zhigang Tian. Involvement of natural killer cells in PolyI:C-induced liver injury. Journal of hepatology. 2004 Dec; 41(6):966-73. doi: 10.1016/j.jhep.2004.08.021. [PMID: 15582130]
  • Beata Kuśnierz-Cabala, Jerzy W Naskalski, Boguslaw Kedra, Józefa Panek. Comparison of sensitivity and specificity of serum poly-C avid ribonuclease activity and C-reactive protein concentration in detection of mild and severe acute pancreatitis. Clinical chemistry and laboratory medicine. 2004 May; 42(5):549-55. doi: 10.1515/cclm.2004.093. [PMID: 15202793]
  • María A Ayllón, Siddarame Gowda, Tatineni Satyanarayana, William O Dawson. cis-acting elements at opposite ends of the Citrus tristeza virus genome differ in initiation and termination of subgenomic RNAs. Virology. 2004 Apr; 322(1):41-50. doi: 10.1016/j.virol.2004.01.005. [PMID: 15063115]
  • Mohammad Alamgir Hossain, Osamu Yamato, Masahiro Yamasaki, Yoshimitsu Maede. Inhibitory effect of pyrimidine and purine nucleotides on the multiplication of Babesia gibsoni: possible cause of low parasitemia and simultaneous reticulocytosis in canine babesiosis. The Journal of veterinary medical science. 2004 Apr; 66(4):389-95. doi: 10.1292/jvms.66.389. [PMID: 15133268]
  • Oscar Cruciani, Luisa Mannina, Anatolij P Sobolev, Annalaura Segre, Pierluigi Luisi. Multilamellar liposomes formed by phosphatidyl nucleosides: an NMR-HR-MAS characterization. Langmuir : the ACS journal of surfaces and colloids. 2004 Feb; 20(4):1144-51. doi: 10.1021/la035804h. [PMID: 15803689]
  • Kazuya Koumoto, Mariko Umeda, Munenori Numata, Takahiro Matsumoto, Kazuo Sakurai, Toyoki Kunitake, Seiji Shinkai. Low Mw sulfated curdlan with improved water solubility forms macromolecular complexes with polycytidylic acid. Carbohydrate research. 2004 Jan; 339(1):161-7. doi: 10.1016/j.carres.2003.09.022. [PMID: 14659684]
  • Irini D Leimoni, Diamantis C Sideris, Emmanuel G Fragoulis. Purification from normal human plasma and biochemical characterization of a ribonuclease specific for poly(C) and poly(U). Archives of biochemistry and biophysics. 2003 May; 413(1):83-90. doi: 10.1016/s0003-9861(03)00082-1. [PMID: 12706344]
  • Yasuomi Yamasaki, Kazuya Sumimoto, Makiya Nishikawa, Fumiyoshi Yamashita, Kiyoshi Yamaoka, Mitsuru Hashida, Yoshinobu Takakura. Pharmacokinetic analysis of in vivo disposition of succinylated proteins targeted to liver nonparenchymal cells via scavenger receptors: importance of molecular size and negative charge density for in vivo recognition by receptors. The Journal of pharmacology and experimental therapeutics. 2002 May; 301(2):467-77. doi: 10.1124/jpet.301.2.467. [PMID: 11961045]
  • Anne-Marie Justin, Jean-Claude Kader, Sylvie Collin. Phosphatidylinositol synthesis and exchange of the inositol head are catalysed by the single phosphatidylinositol synthase 1 from Arabidopsis. European journal of biochemistry. 2002 May; 269(9):2347-52. doi: 10.1046/j.1432-1033.2002.02893.x. [PMID: 11985617]
  • K Sivakumaran, M-H Chen, M J Roossinck, C C Kao. Core promoter for initiation of Cucumber mosaic virus subgenomic RNA4A. Molecular plant pathology. 2002 Jan; 3(1):43-52. doi: 10.1046/j.1464-6722.2001.00089.x. [PMID: 20569307]
  • Bruno Dombrecht, Kathleen Marchal, Jos Vanderleyden, Jan Michiels. Prediction and overview of the RpoN-regulon in closely related species of the Rhizobiales. Genome biology. 2002; 3(12):RESEARCH0076. doi: 10.1186/gb-2002-3-12-research0076. [PMID: 12537565]
  • A T Pearman, H C Castro-Faria-Neto, T M McIntyre, S M Prescott, D M Stafforini. Characterization of human UMP-CMP kinase enzymatic activity and 5' untranslated region. Life sciences. 2001 Oct; 69(20):2361-70. doi: 10.1016/s0024-3205(01)01322-4. [PMID: 11681623]
  • J Li, L Fernandez, K C O'Connor, T Imanishi-Kari, B D Stollar. The rearranged V(H) domain of a physiologically selected anti-single-stranded DNA antibody as a precursor for formation of IgM and IgG antibodies to diverse antigens. Journal of immunology (Baltimore, Md. : 1950). 2001 Oct; 167(7):3746-55. doi: 10.4049/jimmunol.167.7.3746. [PMID: 11564791]
  • J G Leroy, R Seppala, M Huizing, G Dacremont, H De Simpel, R N Van Coster, E Orvisky, D M Krasnewich, W A Gahl. Dominant inheritance of sialuria, an inborn error of feedback inhibition. American journal of human genetics. 2001 Jun; 68(6):1419-27. doi: 10.1086/320598. [PMID: 11326336]
  • C Kirsch, E Logemann, B Lippok, E Schmelzer, K Hahlbrock. A highly specific pathogen-responsive promoter element from the immediate-early activated CMPG1 gene in Petroselinum crispum. The Plant journal : for cell and molecular biology. 2001 Apr; 26(2):217-27. doi: 10.1046/j.1365-313x.2001.01015.x. [PMID: 11389762]
  • S M Lawrence, K A Huddleston, N Tomiya, N Nguyen, Y C Lee, W F Vann, T A Coleman, M J Betenbaugh. Cloning and expression of human sialic acid pathway genes to generate CMP-sialic acids in insect cells. Glycoconjugate journal. 2001 Mar; 18(3):205-13. doi: 10.1023/a:1012452705349. [PMID: 11602804]
  • J Royo, E Gímez, G Hueros. CMP-KDO synthetase: a plant gene borrowed from gram-negative eubacteria. Trends in genetics : TIG. 2000 Oct; 16(10):432-3. doi: 10.1016/s0168-9525(00)02102-8. [PMID: 11050325]
  • M Akeson, D Branton, J J Kasianowicz, E Brandin, D W Deamer. Microsecond time-scale discrimination among polycytidylic acid, polyadenylic acid, and polyuridylic acid as homopolymers or as segments within single RNA molecules. Biophysical journal. 1999 Dec; 77(6):3227-33. doi: 10.1016/s0006-3495(99)77153-5. [PMID: 10585944]
  • E V Gracheva, N K Golovanova, M V Ezhov, P P Malyshev, V V Kukharchuk, N V Prokazova. Plasma sialyltransferase activity in healthy subjects and atherosclerotic patients. Biochemistry. Biokhimiia. 1999 Nov; 64(11):1315-9. doi: NULL. [PMID: 10611539]
  • Z Nie, M Wu. The functional role of a DNA primase in chloroplast DNA replication in Chlamydomonas reinhardtii. Archives of biochemistry and biophysics. 1999 Sep; 369(1):174-80. doi: 10.1006/abbi.1999.1348. [PMID: 10462454]
  • K E de Rudder, C Sohlenkamp, O Geiger. Plant-exuded choline is used for rhizobial membrane lipid biosynthesis by phosphatidylcholine synthase. The Journal of biological chemistry. 1999 Jul; 274(28):20011-6. doi: 10.1074/jbc.274.28.20011. [PMID: 10391951]
  • J P Galaud, M Carrière, N Pauly, H Canut, P Chalon, D Caput, R F Pont-Lezica. Construction of two ordered cDNA libraries enriched in genes encoding plasmalemma and tonoplast proteins from a high-efficiency expression library. The Plant journal : for cell and molecular biology. 1999 Jan; 17(1):111-8. doi: 10.1046/j.1365-313x.1999.00356.x. [PMID: 10069072]
  • J Braess, M Freund, A Hanauske, G Heil, C Kaufmann, W Kern, M Schüssler, W Hiddemann, E Schleyer. Oral cytarabine ocfosfate in acute myeloid leukemia and non-Hodgkin's lymphoma--phase I/II studies and pharmacokinetics. Leukemia. 1998 Oct; 12(10):1618-26. doi: 10.1038/sj.leu.2401152. [PMID: 9766508]
  • Y Ueda, S Mori, T Ito, Y Maesako, H Konishi, Y Yagiri. [A pharmacokinetic study of the value of oral cytarabine ocfosfate in the treatment of hematological malignancies]. [Rinsho ketsueki] The Japanese journal of clinical hematology. 1998 May; 39(5):348-54. doi: NULL. [PMID: 9637884]
  • M E Harrous, A Parody-Morreale. Measurement of biochemical affinities with a Gill titration calorimeter. Analytical biochemistry. 1997 Dec; 254(1):96-108. doi: 10.1006/abio.1997.2386. [PMID: 9398351]
  • H Ide, Y W Kow, B X Chen, B F Erlanger, S S Wallace. Antibodies to oxidative DNA damage: characterization of antibodies to 8-oxopurines. Cell biology and toxicology. 1997 Oct; 13(6):405-17. doi: 10.1023/a:1007467726635. [PMID: 9352119]
  • A Minelli, M Moroni, I Mezzasoma. Human seminal plasma soluble 5'-nucleotidase: regulatory aspects of the dephosphorylation of nucleoside 5'-monophosphates. Biochemical and molecular medicine. 1997 Jun; 61(1):95-101. doi: 10.1006/bmme.1997.2589. [PMID: 9232203]
  • T W Abraham, T I Kalman, E J McIntee, C R Wagner. Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-fluoro-2'-deoxyuridine and 1-beta-arabinofuranosylcytosine: evidence of phosphoramidase activity. Journal of medicinal chemistry. 1996 Nov; 39(23):4569-75. doi: 10.1021/jm9603680. [PMID: 8917645]
  • P G Sorensen, J Lutkenhaus, K Young, S S Eveland, M S Anderson, C R Raetz. Regulation of UDP-3-O-[R-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase in Escherichia coli. The second enzymatic step of lipid a biosynthesis. The Journal of biological chemistry. 1996 Oct; 271(42):25898-905. doi: 10.1074/jbc.271.42.25898. [PMID: 8824222]
  • Y Kiyama, G Suzuki, N Masauzi, H Ohizumi, N Kobayashi, M Ogasawara, T Naohara, M Saito, T Higa, M Kasai. [Treatment of refractory hematologic malignancies by combination of cytarabine ocfosfate and etoposide]. Gan to kagaku ryoho. Cancer & chemotherapy. 1996 Oct; 23(12):1717-20. doi: NULL. [PMID: 8886052]
  • D E Hernández, M L Pellino, B Ramírez. Acute myelocytic leukaemia associated with Kaposi's sarcoma in a patient without serum antibodies to human immunodeficiency virus type 1. The British journal of dermatology. 1996 Mar; 134(3):551-3. doi: NULL. [PMID: 8731687]
  • E del Río, D G Nicholls, C P Downes. Characterization of the effects of lithium and inositol on phosphoinositide turnover in cerebellar granule cells in primary culture. Journal of neurochemistry. 1996 Feb; 66(2):517-24. doi: 10.1046/j.1471-4159.1996.66020517.x. [PMID: 8592121]
  • M Fujiwara, J D Baldeschwieler, R H Grubbs. Receptor-mediated endocytosis of poly(acrylic acid)-conjugated liposomes by macrophages. Biochimica et biophysica acta. 1996 Jan; 1278(1):59-67. doi: 10.1016/0005-2736(95)00183-2. [PMID: 8611608]
  • H Yin, R J Crowder, J P Jones, M W Anders. Reaction of trifluoroacetaldehyde with amino acids, nucleotides, lipid nucleophiles, and their analogs. Chemical research in toxicology. 1996 Jan; 9(1):140-6. doi: 10.1021/tx950072h. [PMID: 8924583]
  • G Herrler, H J Gross, R Brossmer. A synthetic sialic acid analog that is resistant to the receptor-destroying enzyme can be used by influenza C virus as a receptor determinant for infection of cells. Biochemical and biophysical research communications. 1995 Nov; 216(3):821-7. doi: 10.1006/bbrc.1995.2695. [PMID: 7488199]
  • W Yu, W Schuster. Evidence for a site-specific cytidine deamination reaction involved in C to U RNA editing of plant mitochondria. The Journal of biological chemistry. 1995 Aug; 270(31):18227-33. doi: 10.1074/jbc.270.31.18227. [PMID: 7629140]
  • N Sato. A family of cold-regulated RNA-binding protein genes in the cyanobacterium Anabaena variabilis M3. Nucleic acids research. 1995 Jun; 23(12):2161-7. doi: 10.1093/nar/23.12.2161. [PMID: 7541909]
  • E Schleyer, J Braess, B Ramsauer, M Unterhalt, C Kaufmann, S Wilde, M Schüssler, W Hiddemann. Pharmacokinetics of Ara-CMP-Stearate (YNK01): phase I study of the oral Ara-C derivative. Leukemia. 1995 Jun; 9(6):1085-90. doi: . [PMID: 7596174]
  • B Ramsauer, J Braess, M Unterhalt, C C Kaufmann, W Hiddemann, E Schleyer. Highly sensitive high-performance liquid chromatographic assay for 1-beta-D-arabinofuranosylcytosine-5'-stearyl phosphate (cytarabine-ocfosfate). Journal of chromatography. B, Biomedical applications. 1995 Mar; 665(1):183-92. doi: 10.1016/0378-4347(94)00523-8. [PMID: 7795790]
  • H Tsutsumi, T Kumakawa, M Hirai, M Kikukawa, Y Arie, M Mori, H Kodo, N Nakamura, Y Murai, R Mizutani. [Plasma concentration of cytosine arabinoside (Ara-C) in the elderly patients with hematological malignancy treated by Ara-C or cytarabine ocfosfate (SPAC)]. Nihon Ronen Igakkai zasshi. Japanese journal of geriatrics. 1995 Mar; 32(3):190-4. doi: 10.3143/geriatrics.32.190. [PMID: 7596061]
  • E Fernández, M J Fallon, M L Frazier, R de Llorens, C M Cuchillo. Expression of acinar and ductal products in Capan-1 cells growing in synthetic serum and serum-free media. Cancer. 1994 May; 73(9):2285-95. doi: 10.1002/1097-0142(19940501)73:9<2285::aid-cncr2820730909>3.0.co;2-m. [PMID: 7513248]
  • T Ueda, K Kamiya, Y Urasaki, S Wataya, Y Kawai, H Tsutani, M Sugiyama, T Nakamura. Clinical pharmacology of 1-beta-D-arabinofuranosylcytosine-5'-stearylphosphate, an orally administered long-acting derivative of low-dose 1-beta-D-arabinofuranosylcytosine. Cancer research. 1994 Jan; 54(1):109-13. doi: NULL. [PMID: 8261429]
  • M Higashigawa, D C Cao, K Matsui, S Yamada, H Kakitou, Y Kagawa, H Inamochi, M Ido, M Sakurai. Combined oral administration of etoposide and arabinofuranosylcytosine-5'-stearylphosphate enhances the antitumor effect against P388 ascites tumors. Cancer chemotherapy and pharmacology. 1994; 33(4):281-5. doi: 10.1007/bf00685900. [PMID: 8281619]
  • E Rieder, T Bunch, F Brown, P W Mason. Genetically engineered foot-and-mouth disease viruses with poly(C) tracts of two nucleotides are virulent in mice. Journal of virology. 1993 Sep; 67(9):5139-45. doi: 10.1128/jvi.67.9.5139-5145.1993. [PMID: 8394441]
  • Y Song, K Kitajima, Y Inoue. Monoclonal antibody specific to alpha-2-->3-linked deaminated neuraminyl beta-galactosyl sequence. Glycobiology. 1993 Feb; 3(1):31-6. doi: 10.1093/glycob/3.1.31. [PMID: 8448384]
  • S K Datta, J J Trentin. Genetic resistance to lymphoma-leukemia: role of natural killer cells in the rejection of lymphoma grafts. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 1993; 47(10):451-6. doi: 10.1016/0753-3322(93)90342-i. [PMID: 8061245]
  • M D Ludevid, M A Freire, J Gómez, C G Burd, F Albericio, E Giralt, G Dreyfuss, M Pagès. RNA binding characteristics of a 16 kDa glycine-rich protein from maize. The Plant journal : for cell and molecular biology. 1992 Nov; 2(6):999-1003. doi: ". [PMID: 1302645]
  • J Boza, J Jimenez, M J Faus, A Gil. Influences of postnatal age and dietary nucleotides on plasma fatty acids in the weanling rat. JPEN. Journal of parenteral and enteral nutrition. 1992 Jul; 16(4):322-6. doi: 10.1177/0148607192016004322. [PMID: 1322471]
  • E Claro, M A Wallace, J N Fain. Concerted CMP-dependent [3H]inositol labeling of phosphoinositides and agonist activation of phospholipase C in rat brain cortical membranes. Journal of neurochemistry. 1992 Jun; 58(6):2155-61. doi: 10.1111/j.1471-4159.1992.tb10958.x. [PMID: 1315377]
  • H J Gross. Fluorescent CMP-sialic acids as a tool to study the specificity of the CMP-sialic acid carrier and the glycoconjugate sialylation in permeabilized cells. European journal of biochemistry. 1992 Jan; 203(1-2):269-75. doi: 10.1111/j.1432-1033.1992.tb19856.x. [PMID: 1730233]
  • M Fukuoka, T Miyazaki, Y Yoshida, M Hattori, H Niitani, T Nakamura, Y Hirota, K Ohta, M Tanaka, Y Suzuoki. [Phase I study of YNK01 (1-beta-D-arabinofuranosylcytosine-5'-stearylphosphate)]. Gan to kagaku ryoho. Cancer & chemotherapy. 1990 Nov; 17(11):2213-9. doi: NULL. [PMID: 2241185]
  • M Nishikawa, K Morita, F Komada, Y Uemura, S Kageyama, N Minami, K Deguchi, S Shirakawa. [A case of complete remission from acute unclassified leukemia achieved by using a prodrug of ara C, stearyl-ara-CMP (YNK01)]. Gan no rinsho. Japan journal of cancer clinics. 1990 Oct; 36(12):2204-9. doi: NULL. [PMID: 2232191]
  • K Maruoka, M Yamanaka, M Misago, K Nakata, J Tsukada, K Nagata, T Sato, N Mori, S Oda, S Chiba. [Clinical significance of determination of serum RNase activities in patients with eosinophilia--II. Measurements using polyuridylic acid and polycytidylic acid as substrates]. Rinsho byori. The Japanese journal of clinical pathology. 1990 Oct; 38(10):1161-6. doi: NULL. [PMID: 2262974]
  • M Higashigawa, H Hori, T Ohkubo, H Kawasaki, T Yoshizumi, M Sakurai. Deoxyribonucleoside triphosphate pools and Ara-CTP levels in P388 murine leukemic cells treated with 1-B-D-arabinofuranosylcytosine-5'-stearylphosphate which is a newly synthesized derivative of 1-B-D-arabinofuranosylcytosine. Medical oncology and tumor pharmacotherapy. 1990; 7(4):223-6. doi: 10.1007/bf02987099. [PMID: 2283889]
  • T W Munns, S K Freeman. Antibody-nucleic acid complexes. Oligo(dG)n and -(dT)n specificities associated with anti-DNA antibodies from autoimmune MRL mice. Biochemistry. 1989 Dec; 28(26):10048-54. doi: 10.1021/bi00452a025. [PMID: 2559771]
  • M Irie, K Ohgi, R Nitta, M Ikeda, M Ueno. The difference spectra of bovine kidney RNase K2 induced upon binding with nucleotides markedly differ from those of bovine pancreatic RNase. Journal of biochemistry. 1989 Dec; 106(6):994-7. doi: 10.1093/oxfordjournals.jbchem.a122988. [PMID: 2628436]
  • K Kodama, M Morozumi, K Saitoh, A Kuninaka, H Yoshino, M Saneyoshi. Antitumor activity and pharmacology of 1-beta-D-arabinofuranosylcytosine-5'-stearylphosphate: an orally active derivative of 1-beta-D-arabinofuranosylcytosine. Japanese journal of cancer research : Gann. 1989 Jul; 80(7):679-85. doi: 10.1111/j.1349-7006.1989.tb01696.x. [PMID: 2507491]