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Hypoxanthine is a naturally occurring purine derivative. It is occasionally found as a constituent of nucleic acids, where it is present in the anticodon of tRNA in the form of its nucleoside inosine. It has a tautomer known as 6-hydroxypurine. Hypoxanthine is a necessary additive in certain cell, bacteria, and parasite cultures as a substrate and nitrogen source. For example,^[1] it is commonly a required reagent in malaria parasite cultures, since Plasmodium falciparum requires a source of hypoxanthine for nucleic acid synthesis and energy metabolism.

In August 2011, a report, based on NASA studies with meteorites found on Earth, was published suggesting hypoxanthine and related organic molecules, including the DNA and RNA components adenine and guanine, may have been formed extraterrestrially in outer space.^[2]^[3]^[4]

The Pheretima aspergillum worm, used in Chinese medicine preparations, contains hypoxanthine.^[5]

Reactions

It is one of the products of the action of xanthine oxidase on xanthine. However, more frequently in purine degradation, xanthine is formed from reduction of hypoxanthine by xanthine oxidoreductase.

Hypoxanthine-guanine phosphoribosyltransferase converts hypoxanthine into IMP in nucleotide salvage.

Hypoxanthine is also a spontaneous deamination product of adenine. Because of its resemblance to guanine, the spontaneous deamination of adenine can lead to an error in DNA transcription/replication.

Additional images

Adenine
Guanine
Xanthine

References

^ "3H-hypoxanthine uptake inhibition assay for drug susceptibility". WWARN. Retrieved 2012-03-01.
^ Callahan; Smith, K.E.; Cleaves, H.J.; Ruzica, J.; Stern, J.C.; Glavin, D.P.; House, C.H.; Dworkin, J.P. (11 August 2011). "Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases". PNAS. doi:10.1073/pnas.1106493108. Retrieved 2011-08-15.
^ Steigerwald, John (8 August 2011). "NASA Researchers: DNA Building Blocks Can Be Made in Space". NASA. Retrieved 2011-08-10.
^ ScienceDaily Staff (9 August 2011). "DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests". ScienceDaily. Retrieved 2011-08-09.
^ The Pharmacology of Chinese Herbs, Second Edition By Kee C. Huang

External links

Hypoxanthine at the US National Library of Medicine Medical Subject Headings (MeSH)

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UpToDate Contents

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1. 免疫グロブリンの機能および臨床応用 function and clinical applications of immunoglobulins
2. 炎症性腸疾患におけるアザチオプリンおよび6-メルカプトプリン azathioprine and 6 mercaptopurine in inflammatory bowel disease
3. リウマチ性疾患に使用した場合のアザチオプリンの薬理作用および副作用 pharmacology and side effects of azathioprine when used in rheumatic diseases
4. 尿酸による腎疾患 uric acid renal diseases
5. 小児における運動過多な運動障害 hyperkinetic movement disorders in children

English Journal

Post-slaughter changes in ATP metabolites, reducing and phosphorylated sugars in chicken meat.

Aliani M, Farmer LJ, Kennedy JT, Moss BW, Gordon A.SourceAgri-Food and Biosciences Institute, Newforge Lane, Belfast BT9 5PX, UK; Queen's University Belfast, University Road, Belfast BT7 1NN, UK.
Meat science.Meat Sci.2013 May;94(1):55-62. doi: 10.1016/j.meatsci.2012.11.032. Epub 2012 Nov 19.
The formation of ATP breakdown products in chicken M. pectoralis major post-slaughter is reported. The concentrations of metabolites were followed in chicken breast throughout the carcass processing post-slaughter and during chilled storage. The concentration of glucose remains similar throughout th
PMID 23376434

Simultaneous determination of uric acid, xanthine, hypoxanthine and caffeine in human blood serum and urine samples using electrochemically reduced graphene oxide modified electrode.

Raj MA, John SA.SourceCentre for Nanoscience and Nanotechnology, Department of Chemistry, Gandhigram Rural Institute, Gandhigram 624 302, Dindigul, Tamilnadu, India.
Analytica chimica acta.Anal Chim Acta.2013 Apr 10;771:14-20. doi: 10.1016/j.aca.2013.02.017. Epub 2013 Feb 19.
This paper describes the fabrication of graphene on glassy carbon electrode (GCE) by electrochemical reduction of graphene oxide (GO) attached through 1,6-hexadiamine on GCE and the simultaneous determination of structurally similar four purine derivatives using the resultant electrochemically reduc
PMID 23522107

DNA-Reactive Protein Monoepoxides Induce Cell Death and Mutagenesis in Mammalian Cells.

Tretyakova NY, Michaelson-Richie ED, Gherezghiher TB, Kurtz J, Ming X, Wickramaratne S, Campion M, Kanugula S, Pegg AE, Campbell C.AbstractAlthough cytotoxic alkylating agents possessing two electrophilic reactive groups are thought to act by cross-linking cellular biomolecules, their exact mechanisms of action have not been established. In cells, these compounds form a mixture of DNA lesions including nucleobase monoadducts, interstrand and intrastrand cross-links, and DNA-protein cross-links (DPCs). Interstrand DNA-DNA cross-links block replication and transcription by preventing DNA strand separation, contributing to toxicity and mutagenesis. In contrast, potential contributions of drug-induced DPCs are poorly understood. To gain insight into the biological consequences of DPC formation, we generated DNA-reactive protein reagents and examined their toxicity and mutagenesis in mammalian cells. Recombinant human O6-alkylguanine DNA alkyltransferase (AGT) protein or its variants (C145A and K125L) were treated with 1,2,3,4-diepoxybutane to yield proteins containing 2-hydroxy-3,4-epoxybutyl groups on cysteine residues. Gel shift and mass spectrometry experiments confirmed that epoxide-functionalized AGT proteins formed covalent DPC but no other types of nucleobase damage when incubated with duplex DNA. Introduction of purified AGT monoepoxides into mammalian cells via electroporation generated AGT-DNA cross-links and induced cell death and mutations at the hypoxanthine-guanine phosphoribosyltransferase gene. Lower numbers of DPC lesions and reduced levels of cell death were observed when using protein monoepoxides generated from an AGT variant that fails to accumulate in the cell nucleus (K125L), suggesting that nuclear DNA damage is required for toxicity. Taken together, these results indicate that AGT protein monoepoxides produce cytotoxic and mutagenic DPC lesions within chromosomal DNA. More generally, these data suggest that covalent DPC lesions contribute to the cytotoxic and mutagenic effects of bis-electrophiles.
Biochemistry.Biochemistry.2013 Apr 9. [Epub ahead of print]
Although cytotoxic alkylating agents possessing two electrophilic reactive groups are thought to act by cross-linking cellular biomolecules, their exact mechanisms of action have not been established. In cells, these compounds form a mixture of DNA lesions including nucleobase monoadducts, interstra
PMID 23566219

Japanese Journal

Examining cooperative binding of Sox2 on DC5 regulatory element upon complex formation with Pax6 through excess electron transfer assay

Nucleic Acids Research 44(14), 2016-08-19
NAID 120005829395

Evaluation of an Hprt-Luciferase Reporter Gene on a Mammalian Artificial Chromosome in Response to Cytotoxicity

Yonago Acta medica 59(2), 174-182, 2016-06-01
NAID 120005775326

Vidarabine脳症と考えられた3例

神経治療学 33(3), 484-487, 2016
NAID 130005279123

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Hypoxanthine
Names
	IUPAC name 1H-purin-6(9H)-one
Identifiers
CAS Number	68-94-0
ChEBI	CHEBI:17368
ChEMBL	ChEMBL1427
ChemSpider	768
	InChI InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10) Key: FDGQSTZJBFJUBT-UHFFFAOYSA-N ; InChI=1/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10) Key: FDGQSTZJBFJUBT-UHFFFAOYAJ ;
IUPHAR/BPS	4555
Jmol interactive 3D	Image
KEGG	C00262
MeSH	Hypoxanthine
PubChem	790
	SMILES c1[nH]c2c(n1)[nH]cnc2=O ;
UNII	2TN51YD919
Properties
Chemical formula	C5H4N4O
Molar mass	136.112
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references