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Thymine glycol

Thymine glycol (5,6-dihydroxy-5,6-dihydrothymine) is one of the principal DNA lesions that can be induced by oxidation and ionizing radiation.[1]

Thymine glycol
Names
IUPAC name
5,6-Dihydroxy-5-methyldihydro-2,4(1H,3H)-pyrimidinedione
Other names
5,6-Dihydroxy-5,6-dihydrothymine
Identifiers
  • 2943-56-8 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:29128
ChemSpider
  • 17061
  • 18058
  • InChI=1S/C5H8N2O4/c1-5(11)2(8)6-4(10)7-3(5)9/h2,8,11H,1H3,(H2,6,7,9,10)
    Key: GUKSGXOLJNWRLZ-UHFFFAOYSA-N
  • CC1(C(NC(=O)NC1=O)O)O
Properties
C5H8N2O4
Molar mass 160.129 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Aging, stroke edit

The rate at which oxidative reactions generate thymine glycol and thymidine glycol in the DNA of humans is estimated to be about 300 per cell per day.[2] Oxidized DNA bases that are excised by DNA repair processes are excreted in urine. On a body weight basis, mice excrete 18 times more thymine glycol plus thymidine glycol than humans, and monkeys four times more than humans.[2] It was proposed that rate of occurrence of oxidative DNA damages correlates with metabolic rate, and that a higher rate of oxidative damage might cause a higher rate of cellular aging.[2]

Base excision repair is a major DNA repair pathway for removal of oxidative DNA damages. The rate of repair of thymine glycol damage in human fibroblasts was found to decrease with age.[3] Brain samples from humans who died of stroke were found to be deficient in base excision repair of thymine glycol as well as other types of oxidative damages.[4] It was suggested that impaired base excision repair is a risk factor for ischemic brain injury.[4]


References edit

  1. ^ Basu, AK; Loechler, EL; Leadon, SA; Essigmann, JM (1989). "Genetic effects of thymine glycol: site-specific mutagenesis and molecular modeling studies". Proc. Natl. Acad. Sci. U.S.A. 86 (20): 7677–81. Bibcode:1989PNAS...86.7677B. doi:10.1073/pnas.86.20.7677. PMC 298133. PMID 2682618.
  2. ^ a b c Adelman R, Saul RL, Ames BN (1988). "Oxidative damage to DNA: relation to species metabolic rate and life span". Proc. Natl. Acad. Sci. U.S.A. 85 (8): 2706–8. Bibcode:1988PNAS...85.2706A. doi:10.1073/pnas.85.8.2706. PMC 280067. PMID 3128794.
  3. ^ Pons B, Belmont AS, Masson-Genteuil G, Chapuis V, Oddos T, Sauvaigo S (2010). "Age-associated modifications of Base Excision Repair activities in human skin fibroblast extracts". Mech. Ageing Dev. 131 (11–12): 661–5. doi:10.1016/j.mad.2010.09.002. PMID 20854835. S2CID 9845680.
  4. ^ a b Ghosh S, Canugovi C, Yoon JS, Wilson DM, Croteau DL, Mattson MP, Bohr VA (2015). "Partial loss of the DNA repair scaffolding protein, Xrcc1, results in increased brain damage and reduced recovery from ischemic stroke in mice". Neurobiol. Aging. 36 (7): 2319–30. doi:10.1016/j.neurobiolaging.2015.04.004. PMC 5576895. PMID 25971543.

thymine, glycol, dihydroxy, dihydrothymine, principal, lesions, that, induced, oxidation, ionizing, radiation, names, iupac, name, dihydroxy, methyldihydro, pyrimidinedione, other, names, dihydroxy, dihydrothymine, identifiers, number, 2943, model, jsmol, inte. Thymine glycol 5 6 dihydroxy 5 6 dihydrothymine is one of the principal DNA lesions that can be induced by oxidation and ionizing radiation 1 Thymine glycol Names IUPAC name 5 6 Dihydroxy 5 methyldihydro 2 4 1H 3H pyrimidinedione Other names 5 6 Dihydroxy 5 6 dihydrothymine Identifiers CAS Number 2943 56 8 Y 3D model JSmol Interactive image ChEBI CHEBI 29128 ChemSpider 17061 PubChem CID 18058 InChI InChI 1S C5H8N2O4 c1 5 11 2 8 6 4 10 7 3 5 9 h2 8 11H 1H3 H2 6 7 9 10 Key GUKSGXOLJNWRLZ UHFFFAOYSA N SMILES CC1 C NC O NC1 O O O Properties Chemical formula C 5H 8N 2O 4 Molar mass 160 129 g mol 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesAging stroke editThe rate at which oxidative reactions generate thymine glycol and thymidine glycol in the DNA of humans is estimated to be about 300 per cell per day 2 Oxidized DNA bases that are excised by DNA repair processes are excreted in urine On a body weight basis mice excrete 18 times more thymine glycol plus thymidine glycol than humans and monkeys four times more than humans 2 It was proposed that rate of occurrence of oxidative DNA damages correlates with metabolic rate and that a higher rate of oxidative damage might cause a higher rate of cellular aging 2 Base excision repair is a major DNA repair pathway for removal of oxidative DNA damages The rate of repair of thymine glycol damage in human fibroblasts was found to decrease with age 3 Brain samples from humans who died of stroke were found to be deficient in base excision repair of thymine glycol as well as other types of oxidative damages 4 It was suggested that impaired base excision repair is a risk factor for ischemic brain injury 4 References edit Basu AK Loechler EL Leadon SA Essigmann JM 1989 Genetic effects of thymine glycol site specific mutagenesis and molecular modeling studies Proc Natl Acad Sci U S A 86 20 7677 81 Bibcode 1989PNAS 86 7677B doi 10 1073 pnas 86 20 7677 PMC 298133 PMID 2682618 a b c Adelman R Saul RL Ames BN 1988 Oxidative damage to DNA relation to species metabolic rate and life span Proc Natl Acad Sci U S A 85 8 2706 8 Bibcode 1988PNAS 85 2706A doi 10 1073 pnas 85 8 2706 PMC 280067 PMID 3128794 Pons B Belmont AS Masson Genteuil G Chapuis V Oddos T Sauvaigo S 2010 Age associated modifications of Base Excision Repair activities in human skin fibroblast extracts Mech Ageing Dev 131 11 12 661 5 doi 10 1016 j mad 2010 09 002 PMID 20854835 S2CID 9845680 a b Ghosh S Canugovi C Yoon JS Wilson DM Croteau DL Mattson MP Bohr VA 2015 Partial loss of the DNA repair scaffolding protein Xrcc1 results in increased brain damage and reduced recovery from ischemic stroke in mice Neurobiol Aging 36 7 2319 30 doi 10 1016 j neurobiolaging 2015 04 004 PMC 5576895 PMID 25971543 Retrieved from https en wikipedia org w index php title Thymine glycol amp oldid 1045752544, wikipedia, wiki, book, books, library,

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