Isoguanosine: Isolation from an Animal

Fuhrman, Frederick A.; Fuhrman, Geraldine J.; Nachman, Ronald J.; Mosher, Harry S.

doi:10.1126/science.7209552

Cited by 57 publications

(25 citation statements)

References 19 publications

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“…Although isoguanine (iG), as a ribonucleoside, and its methyl derivatives occurs in Nature [1][2][3][4], it has not been established that this base represents a natural constituent of nucleic acids. However, iG (1,2-dihydro-2-oxoadenine or 2-hydroxyadenine) is formed in DNA, among other oxidized bases, in the reaction of reactive oxygen species with adenine [5].…”

Section: Introductionmentioning

confidence: 99%

Neighbouring bases in template influence base-pairing of isoguanine

Maciejewska

Lichota

Kuśmierek

2003

Biochemical Journal

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Assuming that the efficiency of the incorporation of 5-methyl-2h-deoxyisocytosine-5h triphosphate (dMiCTP) and dTTP opposite isoguanine (iG) is a measure of the proportion of the keto and enol tautomers of iG in the Thermus aquaticus DNA polymerase active centre, we studied the influence of temperature and iGneighbouring bases in the template on base-pairing of iG. On the basis of experiments with four sequences (3h-TXT-5h, 3h-GXG-5h, 3h-CXC-5h, 3h-CXT-5h, where X l iG) at 37, 50, 65 and 80 mC, we found that 3h-neighbours decrease the fraction of the keto tautomer in the order C G T, whereas temperature apparently does not influence the tautomeric equilibrium of iG. The variability of the ratio of incorporation of dMiCTP versus dTTP (5-20) primarily reflects the variability of K m values, since

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Section: Introductionmentioning

confidence: 99%

Neighbouring bases in template influence base-pairing of isoguanine

Maciejewska

Lichota

Kuśmierek

2003

Biochemical Journal

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“…For example, isoG has been isolated from butterfly wings [7], and the riboside of is&, isoguanosine (crotonoside), is known in nature as a constituent of the croton bean, Croton tiglium L [8]. Quite recently, an isolation of isoguanosine from an animal, the marine nudibranch mollusk Disululu sundiegensis, has been reported [9]. On the other hand, the C-nucleoside of isoC (JI-isocytidine) is known as an antileukemia drug [ 101.…”

Section: Introductionmentioning

confidence: 99%

Why isoguanine and isocytosine are not the components of the genetic code

Jaworski

Kwiatkowski

Lesyng

2009

Int. J. Quantum Chem.

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“…1,2-Dihydro-2-oxoadenosine (2-oxoadenosine; 2-oxo-Ado), an oxidized form of adenosine and also known as 2-hydroxyadenosine, isoguanosine or crotonoside, has been reported as a naturally generated nucleoside analogue in Croton tiglium 1 and Diaulula sandiegensis 2 . 2-Oxo-Ado has not been identified in mammals, but some biological activities have been shown in mammals, such as effects on muscle contraction 3 and cAMP accumulation 4 .…”

Section: Introductionmentioning

confidence: 99%

2-Oxoadenosine induces cytotoxicity through intracellular accumulation of 2-oxo-ATP and depletion of ATP but not via the p38 MAPK pathway

Asada

Ohta

Akimoto

et al. 2017

Sci Rep

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2-Oxoadenosine (2-oxo-Ado), an oxidized form of adenosine, is cytotoxic and induces growth arrest and cell death, which has potential as an anti-cancer drug. However, it is not well understood how 2-oxo-Ado exerts its cytotoxicity. We examined the effects of 2-oxo-Ado on non-tumour cells, namely immortalized mouse embryonic fibroblast lines, and investigated mechanisms by which 2-oxo-Ado exerts its cytotoxicity. We found that cell death induced by 2-oxo-Ado is classical caspase-dependent apoptosis, and requires its sequential intracellular phosphorylation catalysed by adenosine kinase (ADK) and adenylate kinase 2, resulting in intracellular accumulation of 2-oxo-ATP accompanied by accumulation of 2-oxo-Ado in RNA and depletion of ATP. Moreover, we showed that overexpression of MTH1, an oxidized purine nucleoside triphosphatase, prevents 2-oxo-Ado-induced cytotoxicity accompanied by suppression of accumulation of both intracellular 2-oxo-ATP and 2-oxo-Ado in RNA and recovery of ATP levels. We also found that 2-oxo-Ado activates the p38 MAPK pathway. However, siRNAs against Mkk3 and Mkk6, or treatment with several p38 MAPK inhibitors, except SB203580, did not prevent the cytotoxicity. SB203580 prevented intracellular phosphorylation of 2-oxo-Ado to 2-oxo-AMP, and an in vitro ADK assay revealed that SB203580 directly inhibits ADK activity, suggesting that some of the effects of SB203580 may depend on ADK inhibition.

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Isoguanosine: Isolation from an Animal

Abstract: Isoguanosine (oxyadenosine or crotonoside), previously known to occur in nature only in the croton bean, was isolated from an animal, the marine nudibranch mollusk Diaulula sandiegensis.

Cited by 57 publications

References 19 publications

Neighbouring bases in template influence base-pairing of isoguanine

Neighbouring bases in template influence base-pairing of isoguanine

Why isoguanine and isocytosine are not the components of the genetic code

2-Oxoadenosine induces cytotoxicity through intracellular accumulation of 2-oxo-ATP and depletion of ATP but not via the p38 MAPK pathway

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