8-Oxoguanina: Diferenzas entre revisións

8-Oxoguanina
	Nome IUPAC 2-Amino-7,9-dihidro-1H-purina-6,8-diona
	Outros nomes 7,8-Dihidro-8-oxoguanina; 8-Oxo-7,8-dihidroguanina
Identificadores
Número CAS	5614-64-2
PubChem	119315
ChemSpider	106574
MeSH	8-hydroxyguanine
ChEBI	CHEBI:44605
Imaxes 3D Jmol	Image 1; Image 2
	SMILES O=C2NC=1N\C(=N/C(=O)C=1N2)N c12=NC(=O)N=c1[nH]c(nc2=O)N ;
	InChI InChI=1S/C5H3N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H3,6,8,9,10,11,12); Key: UBKVUFQGVWHZIR-UHFFFAOYSA-N InChI=1/C5H5N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H5,6,7,8,9,10,11,12); Key: CLGFIVUFZRGQRP-UHFFFAOYAZ InChI=1/C5H3N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H3,6,8,9,10,11,12); Key: UBKVUFQGVWHZIR-UHFFFAOYAW;
Propiedades
Fórmula molecular	C5H5N5O2
Masa molar	167,13 g mol−1
	; Se non se indica outra cousa, os datos están tomados en condicións estándar de 25 °C e 100 kPa.

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En liña

Revisión como estaba o 7 de outubro de 2016 ás 22:13

A 8-oxoguanina (ou 8-hidroxiguanina, 8-oxo-Gua, ou OH⁸Gua) é unha base nitroxenada que se forma como unha das lesións no ADN máis comúns causada polas especies reactivas do oxíxeno ^[2] e pode orixinar un apareamento incorrecto coa adenina, o que ten como resultado substitucións de G a T e de C a A no xenoma.^[3] Nos humanos, é reparada fundamengtalmente pola ADN glicosilase OGG1. Pode orixinarse pola acción da radiación ionizante en conexión co metabolismo oxidativo.

En fluídos corporais

O incremento das concentracións de 8-oxoguanina nos fluídos corporais asociouse cun incremento do risco de mutaxénese e carcinoxénese.^[4]^[5]

Os ensaios don 8-oxoguanina deben facerse con moito coidado debido á facilidade coa qued pode ser oxidada durante a extracción e os procedementos do ensaio.^[6]

Notas

↑ 8-hydroxyguanine - Compound Summary, PubChem
↑ Kanvah, S.; et al. (2010). ", Oxidation of DNA: Damage to Nucleobases". Acc. Chem. Res. 43 (2): 280–287. doi:10.1021/ar900175a.
↑ Cheng KC; Cahill DS; Kasai H; Nishimura S; Loeb LA (Jan 5, 1992). "8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G→T and C→A substitutions.". J Biol Chem. 267 (1): 166–72. PMID 1730583.
↑ Kasai, H (December 1997). "Analysis of a form of oxidative DNA damage, 8-hydroxy-2'-deoxyguanosine, as a marker of cellular oxidative stress during carcinogenesis.". Mutation research 387 (3): 147–63. PMID 9439711. doi:10.1016/s1383-5742(97)00035-5.
↑ Halliwell, B (December 1998). "Can oxidative DNA damage be used as a biomarker of cancer risk in humans? Problems, resolutions and preliminary results from nutritional supplementation studies.". Free Radical Research 29 (6): 469–86. PMID 10098453. doi:10.1080/10715769800300531.
↑ Ravanat, JL; Douki, T; Duez, P; Gremaud, E; Herbert, K; Hofer, T; Lasserre, L; Saint-Pierre, C; Favier, A; Cadet, J (November 2002). "Cellular background level of 8-oxo-7,8-dihydro-2'-deoxyguanosine: an isotope based method to evaluate artefactual oxidation of DNA during its extraction and subsequent work-up". Carcinogenesis 23 (11): 1911–8. PMID 12419840. doi:10.1093/carcin/23.11.1911.

Véxase tamén

Outros artigos

[1] 8-hydroxyguanine - Compound Summary, PubChem

[2] Kanvah, S.; et al. (2010). ", Oxidation of DNA: Damage to Nucleobases". Acc. Chem. Res. 43 (2): 280–287. doi:10.1021/ar900175a.

[3] Cheng KC; Cahill DS; Kasai H; Nishimura S; Loeb LA (Jan 5, 1992). "8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G→T and C→A substitutions.". J Biol Chem. 267 (1): 166–72. PMID 1730583.

[4] Kasai, H (December 1997). "Analysis of a form of oxidative DNA damage, 8-hydroxy-2'-deoxyguanosine, as a marker of cellular oxidative stress during carcinogenesis.". Mutation research 387 (3): 147–63. PMID 9439711. doi:10.1016/s1383-5742(97)00035-5.

[5] Halliwell, B (December 1998). "Can oxidative DNA damage be used as a biomarker of cancer risk in humans? Problems, resolutions and preliminary results from nutritional supplementation studies.". Free Radical Research 29 (6): 469–86. PMID 10098453. doi:10.1080/10715769800300531.

[6] Ravanat, JL; Douki, T; Duez, P; Gremaud, E; Herbert, K; Hofer, T; Lasserre, L; Saint-Pierre, C; Favier, A; Cadet, J (November 2002). "Cellular background level of 8-oxo-7,8-dihydro-2'-deoxyguanosine: an isotope based method to evaluate artefactual oxidation of DNA during its extraction and subsequent work-up". Carcinogenesis 23 (11): 1911–8. PMID 12419840. doi:10.1093/carcin/23.11.1911.

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@@ Liña 49: / Liña 49: @@
 == En fluídos corporais ==
-Increased concentrations of 8-oxoguanine in body fluids have been found to be associated with increased risk of [[mutagenesis]] and [[carcinogenesis]].<ref>{{cite journal|last1=Kasai|first1=H|title=Analysis of a form of oxidative DNA damage, 8-hydroxy-2'-deoxyguanosine, as a marker of cellular oxidative stress during carcinogenesis.|journal=Mutation research|date=December 1997|volume=387|issue=3|pages=147–63|pmid=9439711|doi=10.1016/s1383-5742(97)00035-5}}</ref><ref>{{cite journal|last1=Halliwell|first1=B|title=Can oxidative DNA damage be used as a biomarker of cancer risk in humans? Problems, resolutions and preliminary results from nutritional supplementation studies.|journal=Free Radical Research|date=December 1998|volume=29|issue=6|pages=469–86|pmid=10098453|doi=10.1080/10715769800300531}}</ref>
+O incremento das concentracións de 8-oxoguanina nos fluídos corporais asociouse cun incremento do risco de [[mutaxénese]] e [[carcinoxénese]].<ref>{{cite journal|last1=Kasai|first1=H|title=Analysis of a form of oxidative DNA damage, 8-hydroxy-2'-deoxyguanosine, as a marker of cellular oxidative stress during carcinogenesis.|journal=Mutation research|date=December 1997|volume=387|issue=3|pages=147–63|pmid=9439711|doi=10.1016/s1383-5742(97)00035-5}}</ref><ref>{{cite journal|last1=Halliwell|first1=B|title=Can oxidative DNA damage be used as a biomarker of cancer risk in humans? Problems, resolutions and preliminary results from nutritional supplementation studies.|journal=Free Radical Research|date=December 1998|volume=29|issue=6|pages=469–86|pmid=10098453|doi=10.1080/10715769800300531}}</ref>
-Care must be taken in the assay of 8-oxoguanine due to the ease with which it can be oxidised during extraction and the assay procedure.<ref>{{cite journal |last1=Ravanat |first1=JL| last2=Douki |first2=T |last3=Duez |first3=P |last4=Gremaud |first4=E |last5=Herbert |first5=K |last6=Hofer |first6=T |last7=Lasserre |first7=L |last8=Saint-Pierre |first8=C |last9=Favier |first9=A |last10=Cadet |first10=J |title=Cellular background level of 8-oxo-7,8-dihydro-2'-deoxyguanosine: an isotope based method to evaluate artefactual oxidation of DNA during its extraction and subsequent work-up |journal=Carcinogenesis |date=November 2002 |volume=23 |issue=11 |pages=1911–8 |pmid=12419840 |doi=10.1093/carcin/23.11.1911}}</ref>
+Os ensaios don 8-oxoguanina deben facerse con moito coidado debido á facilidade coa qued pode ser oxidada durante a extracción e os procedementos do ensaio.<ref>{{cite journal |last1=Ravanat |first1=JL| last2=Douki |first2=T |last3=Duez |first3=P |last4=Gremaud |first4=E |last5=Herbert |first5=K |last6=Hofer |first6=T |last7=Lasserre |first7=L |last8=Saint-Pierre |first8=C |last9=Favier |first9=A |last10=Cadet |first10=J |title=Cellular background level of 8-oxo-7,8-dihydro-2'-deoxyguanosine: an isotope based method to evaluate artefactual oxidation of DNA during its extraction and subsequent work-up |journal=Carcinogenesis |date=November 2002 |volume=23 |issue=11 |pages=1911–8 |pmid=12419840 |doi=10.1093/carcin/23.11.1911}}</ref>
 == Notas ==