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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/11/08 02:09:28」(JST)
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Not to be confused with cytosine, cysteine, cystine, or cytisine.
Cytidine |
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IUPAC name
4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
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Identifiers |
CAS number |
65-46-3 Y |
PubChem |
6175 |
ChemSpider |
5940 Y |
UNII |
5CSZ8459RP Y |
KEGG |
D07769 Y |
MeSH |
Cytidine |
ChEBI |
CHEBI:17562 Y |
ChEMBL |
CHEMBL95606 Y |
Jmol-3D images |
Image 1 |
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O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO
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InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7-,8-/m1/s1 Y
Key: UHDGCWIWMRVCDJ-XVFCMESISA-N Y
InChI=1/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7-,8-/m1/s1
Key: UHDGCWIWMRVCDJ-XVFCMESIBD
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Properties |
Molecular formula |
C9H13N3O5 |
Molar mass |
243.22 g mol−1 |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
Infobox references |
Cytidine is a nucleoside molecule that is formed when cytosine is attached to a ribose ring (also known as a ribofuranose) via a β-N1-glycosidic bond. Cytidine is a component of RNA.
If cytosine is attached to a deoxyribose ring, it is known as a deoxycytidine.
Dietary sources of cytidine[edit]
Dietary sources of cytidine include foods with high RNA (ribonucleic acid) content,[1] such as organ meats, Brewer's yeast, as well as pyrimidine-rich foods such as beer. During digestion, RNA-rich foods are broken-down into ribosyl pyrimidines (cytidine and uridine), which are absorbed intact.[1] In humans, dietary cytidine is converted into uridine,[2] which is probably the compound behind cytidine's metabolic effects.
Cytidine analogs[edit]
There are a variety of cytidine analogs with potentially useful pharmacology. For example, KP-1461 is an anti-HIV agent that works as a viral mutagen,[3] and zebularine exists in E. coli and is being examined for chemotherapy. Low doses of azacitidine and its analog decitabine have shown results against cancer through epigenetic demethylation.[4]
References[edit]
- ^ a b Jonas DA, Elmadfa I, Engel KH et al. (2001). "Safety considerations of DNA in food". Ann Nutr Metab. 45 (6): 235–54. doi:10.1159/000046734. PMID 11786646.
- ^ Wurtman RJ, Regan M, Ulus I, Yu L (Oct 2000). "Effect of oral CDP-choline on plasma choline and uridine levels in humans". Biochem Pharmacol. 60 (7): 989–92. doi:10.1016/S0006-2952(00)00436-6. PMID 10974208.
- ^ John S. James. "New Kind of Antiretroviral, KP-1461". AIDS Treatment News.
- ^ "Scientists reprogram cancer cells with low doses of epigenetic drugs". Medical XPress. March 22, 2012.
Nucleic acid constituents
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Nucleobase |
Purine (Adenine, Guanine, Hypoxanthine, Xanthine, Purine analogue) · Pyrimidine (Uracil, Thymine, Cytosine, Pyrimidine analogue)
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Nucleoside |
Ribonucleoside
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Adenosine · Guanosine · 5-Methyluridine · Uridine · Cytidine · Inosine · Xanthosine
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Deoxyribonucleoside
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Deoxyadenosine · Deoxyguanosine · Thymidine · Deoxyuridine · Deoxycytidine · Deoxyinosine · Deoxyxanthosine
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Nucleotide
(Nucleoside monophosphate) |
Ribonucleotide
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AMP, GMP, m5UMP, UMP, CMP, IMP, XMP
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Deoxyribonucleotide
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dAMP, dGMP, dTMP, dUMP, dCMP, dIMP, dXMP
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Cyclic nucleotide
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cAMP, cGMP, c-di-GMP, cADPR
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Nucleoside diphosphate |
ADP, GDP, m5UDP, UDP, CDP · dADP, dGDP, dTDP, dUDP, dCDP
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Nucleoside triphosphate |
ATP, GTP, m5UTP, UTP, CTP, ITP, XTP · dATP, dGTP, dTTP, dUTP, dCTP, dITP, dXTP
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- Biochemical families: carbohydrates
- alcohols
- glycoproteins
- glycosides
- lipids
- eicosanoids
- fatty acids / intermediates
- phospholipids
- sphingolipids
- steroids
- nucleic acids
- constituents / intermediates
- proteins
- Amino acids / intermediates
- tetrapyrroles / intermediates
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UpToDate Contents
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English Journal
- Highly selective and sensitive adenosine aptasensor based on platinum nanoparticles as catalytical label for amplified detection of biorecognition events through H2O2 reduction.
- Shahdost-Fard F, Salimi A, Khezrian S.Author information Department of Chemistry, University of Kurdistan, 66177-15175 Sanandaj, Iran.AbstractBased on a combination of aptamer and platinum nanoparticles a new sensitive and selective adenosine aptasensor was fabricated. Functionalized thiol-terminated adenosine aptamer (5'-AGAGAACCTGGGGGAGTATTGCGGAGGAAGGT-SH-3') with Pt Nanoparticles (Pt-NPs) was employed as highly catalytic label for electrochemical detection of adenosine based on electrocatalytic activity of Pt-NPs toward H2O2 reduction. Multiwalled carbon nanotubes/ionic liquid/chitosan (MWCNTs/IL/CHIT) nanocomposite was applied as the interface for covalent attachment of 3'-amine-terminated capture probe (3'-NH2-(CH2)6-TCTCTTGGACCC-5'). The presence of Pt nanoparticles improvement the conductivity and performance characteristics of the biosensor as well as incensement in the loading amount of the aptamer DNA sequence. The interaction of adenosine with the aptamer causes the releasing of aptamer with PtNPs into solution which resulted in a decreasing of hydrogen peroxide reduction peak current. Sensitive quantitative detection of adenosine was achieved by monitoring the decrease of voltammetric responses of H2O2 peak current. The peak current of H2O2 decreased with increase in the concentration of adenosine over a range of 1-750nM with detection limit 1nM. In addition the proposed aptasensor showed excellent selectivity toward adenosine in compared to some other nucleosides such as guanosine, cytidine and uridine. The proposed aptasensor was successfully used to detect adenosine in human serum samples. The elimination of enzymes or antibodies for the amplified detection of adenosine and the use of platinum nanoparticles as inorganic catalytic label, are the advantage of the proposed aptasensor.
- Biosensors & bioelectronics.Biosens Bioelectron.2014 Mar 15;53:355-62. doi: 10.1016/j.bios.2013.09.024. Epub 2013 Sep 27.
- Based on a combination of aptamer and platinum nanoparticles a new sensitive and selective adenosine aptasensor was fabricated. Functionalized thiol-terminated adenosine aptamer (5'-AGAGAACCTGGGGGAGTATTGCGGAGGAAGGT-SH-3') with Pt Nanoparticles (Pt-NPs) was employed as highly catalytic label for elec
- PMID 24176972
- A model of liver carcinogenesis originating from hepatic progenitor cells with accumulation of genetic alterations.
- Kim SK, Nasu A, Komori J, Shimizu T, Matsumoto Y, Minaki Y, Kohno K, Shimizu K, Uemoto S, Chiba T, Marusawa H.Author information Department of Gastroenterology and Hepatology, Graduate School of MedicineKyoto University, Kyoto, Japan.AbstractActivation-induced cytidine deaminase (AID) contributes to inflammation-associated carcinogenesis through its mutagenic activity. In our study, by taking advantage of the ability of AID to induce genetic aberrations, we investigated whether liver cancer originates from hepatic stem/progenitor cells that accumulate stepwise genetic alterations. For this purpose, hepatic progenitor cells enriched from the fetal liver of AID transgenic (Tg) mice were transplanted into recipient "toxin-receptor mediated conditional cell knockout" (TRECK) mice, which have enhanced liver regeneration activity under the condition of diphtheria toxin treatment. Whole exome sequencing was used to determine the landscape of the accumulated genetic alterations in the transplanted progenitor cells during tumorigenesis. Liver tumors developed in 7 of 11 (63.6%) recipient TRECK mice receiving enriched hepatic progenitor cells from AID Tg mice, while no tumorigenesis was observed in TRECK mice receiving hepatic progenitor cells of wild-type mice. Histologic examination revealed that the tumors showed characteristics of hepatocellular carcinoma and partial features of cholangiocarcinoma with expression of the AID transgene. Whole exome sequencing revealed that several dozen genes acquired single nucleotide variants in tumor tissues originating from the transplanted hepatic progenitor cells of AID Tg mice. Microarray analyses revealed that the majority of the mutations (>80%) were present in actively transcribed genes in the liver-lineage cells. These findings provided the evidence suggesting that accumulation of genetic alterations in fetal hepatic progenitor cells progressed to liver cancers, and the selection of mutagenesis depends on active transcription in the liver-lineage cells.
- International journal of cancer. Journal international du cancer.Int J Cancer.2014 Mar 1;134(5):1067-76. doi: 10.1002/ijc.28445. Epub 2013 Sep 16.
- Activation-induced cytidine deaminase (AID) contributes to inflammation-associated carcinogenesis through its mutagenic activity. In our study, by taking advantage of the ability of AID to induce genetic aberrations, we investigated whether liver cancer originates from hepatic stem/progenitor cells
- PMID 23959426
- Three novel homozygous mutations in the GNPTG gene that cause mucolipidosis type III gamma.
- Liu S1, Zhang W2, Shi H3, Meng Y3, Qiu Z4.Author information 1Department of Pediatrics, PUMC Hospital, CAMS&PUMC, Beijing 100730, PR China.2Clinical Research Laboratory, Peking Union Medical College Hospital, Chinese Academy of Medical Sciences, Beijing, PR China.3Department of Medical Genetics, Institute of Basic Medical Sciences, Chinese Academy of Medical Sciences, PR China.4Department of Pediatrics, PUMC Hospital, CAMS&PUMC, Beijing 100730, PR China. Electronic address: zhengqingqiu33@aliyun.com.AbstractBACKGROUND: Mucolipidosis type III gamma (MLIII gamma) is an autosomal recessive disease caused by a mutation in the GNPTG gene, which encodes the γ subunit of the N-acetylglucosamine-1-phosphotransferase (GlcNAc-1-phosphotransferase). This protein plays a key role in the transport of lysosomal hydrolases to the lysosome.
- Gene.Gene.2014 Feb 10;535(2):294-8. doi: 10.1016/j.gene.2013.11.010. Epub 2013 Dec 6.
- BACKGROUND: Mucolipidosis type III gamma (MLIII gamma) is an autosomal recessive disease caused by a mutation in the GNPTG gene, which encodes the γ subunit of the N-acetylglucosamine-1-phosphotransferase (GlcNAc-1-phosphotransferase). This protein plays a key role in the transport of lysosomal hyd
- PMID 24316125
Japanese Journal
- 免疫グロブリンの体細胞高頻度突然変異とserine/arginine-rich protein splicing factor (SRSF) (特集 免疫グロブリンの体細胞高頻度突然変異とクラススイッチ)
- AIDによる免疫グロブリンの体細胞高頻度突然変異誘導と関連分子 (特集 免疫グロブリンの体細胞高頻度突然変異とクラススイッチ)
- C-terminal region of activation-induced cytidine deaminase (AID) is required for efficient class switch recombination and gene conversion.
- Sabouri Somayeh,Kobayashi Maki,Begum Nasim A,Xu Jianliang,Hirota Kouji,Honjo Tasuku
- Proceedings of the National Academy of Sciences of the United States of America 111(6), 2253-2258, 2014-02-11
- … Activation-induced cytidine deaminase (AID) introduces single-strand breaks (SSBs) to initiate class switch recombination (CSR), gene conversion (GC), and somatic hypermutation (SHM). …
- NAID 120005395696
Related Links
- cyt·i·dine / ˈsɪt ɪˌdin, -dɪn, ˈsaɪ tɪ-/ Show Spelled [sit-i-deen, -din, sahy-ti-] Show IPA noun Biochemistry. a white crystalline powder, C 9 H 13 N 3 O 5, that is a ribonucleoside consisting of d-ribose and cytosine. Origin: German Cytidin ...
- [Cytidine] [65-46-3] | 価格や在庫、物性値などの詳細情報ページです。 ... 使い方 見積依頼フォーム ご購入について 構造式検索 詳細検索 一括検索 カテゴリ50音順インデックス カテゴリ別インデックス
Related Pictures
★リンクテーブル★
[★]
- 英
- cytidine, Cyd
- 同
- シトシンリボシド cytosine riboside
- 関
- [[]]
[★]
5-アザ-2'-デオキシシチジン
- 関
- decitabine
[★]
活性化誘導シチジンデアミナーゼ AID
[★]
ブロモデオキシシチジン