Oxidation of Adenosine and Inosine: The Chemistry of 8-Oxo-7,8-dihydropurines, Purine Iminoquinones, and Purine Quinones as Observed by Ultrafast Spectroscopy

Nilov, Denis I.; Komarov, Dmitry Y; Panov, Maxim S.; Karabaeva, Kanykey E.; Mereshchenko, Andrey S.; Tarnovsky, Alexander N.; Wilson, R. Marshall

doi:10.1021/ja3068148

Cited by 27 publications

(28 citation statements)

References 67 publications

(158 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[20][21][22][23][24] As with the hydroxyl radical, the mechanism for this attack is explained by two equally plausible theories. In both cases, the creation of 8-oxoguanine proceeds to form an intermediate product:…”

Section: -Hydroxy-2'-deoxyguanosinementioning

confidence: 99%

Analytics of oxidative stress markers in the early diagnosis of oxygen DNA damage

Dąbrowska¹,

Wiczkowski²

2017

Adv Clin Exp Med

View full text Add to dashboard Cite

Under homeostatic conditions, an equilibrium state between amounts of free radicals formed and their scavenging is observed. Free radicals are destructive only when present in excess. Pathological changes within cells and tissues can result from a persistent excess of free radicals. Living organisms are increasingly exposed to oxidative stress, resulting in oxidative DNA modifications. One such modification is 8-hydroxy-2'-deoxyguanosine (8-OHdG). It is considered a biomarker of oxidative stress and oxidative DNA damage. It has been found both in physiological fluids and in cells. This paper presents methods found in the literature for determining 8-OHdG expression in various kinds of biological material -blood, urine or liver homogenates. Methods for determining the biomarker expression have been grouped into direct and indirect methods, and the various levels of 8-hydroxy-2'-deoxyguanosine that can be determined by the different techniques are presented. The basic pros and cons of the various techniques are also discussed.

show abstract

Section: -Hydroxy-2'-deoxyguanosinementioning

confidence: 99%

Analytics of oxidative stress markers in the early diagnosis of oxygen DNA damage

Dąbrowska¹,

Wiczkowski²

2017

Adv Clin Exp Med

View full text Add to dashboard Cite

show abstract

“…Amongst the canonical bases, guanosine and adenosine have the lowest oxidation potentials, 1.29 and 1.42 eV, respectively, and are common targets for their corresponding reactions with ROS (e.g., O 2 2– , •OH, •OOH, and 1 O 2 ). One of the main products arising from these events corresponds to oxidation at the C‐8 position to yield the 7,8‐dihydro‐8‐hydroxy‐purines, namely 8‐oxo‐guanosine and 8‐oxo‐adenosine (8‐oxoA, Scheme ) . In fact, these oxidative lesions (1:0.4 ratio 8‐oxoG/8‐oxoA) constitute about 64% of the main modifications observed in DNA of mammalian chromatin subjected to γ‐radiolysis .…”

Section: Introductionmentioning

confidence: 99%

Biophysical properties and thermal stability of oligonucleotides of RNA containing 7,8‐dihydro‐8‐hydroxyadenosine

2014

View full text Add to dashboard Cite

Circular dichroism (CD) was used to assess the stabilization/destabilization imposed by oxidative lesion 7,8-dihydro-8-hydroxyadenosine (8-oxoA) on strands of RNA with different structural motifs. RNA:RNA homoduplex destabilization was observed in a position dependent manner using 10-mers as models that displayed differences between 12.7 and 15.1°C. We found that increasing the number of modifications resulted in depressed Tm values of about 12–15°C per lesion. The same effect was observed on RNA:DNA heteroduplex samples. We also tested the effects of this lesion in short hairpins containing the tetraloop UUCX (X = A, 8-oxoA). We found that the stem was hypersensitive to substitution of A by 8-oxoA and that it destabilized the structure by >23°C. Concomitant substitution at the stem and loop prevented formation of this secondary structure or lead to other less-stable hairpins. Incorporation of this lesion at the first base of the loop had no effect on either structure. Overall, we found that the effects of 8-oxoA on RNA structure are position dependent and that its stabilization may vary from sharp decreases to small increments, in some cases, leading to the formation of other more/less stable structures. These structural changes may have larger biological implications, particularly if the oxidatively modified RNA persists, thus leading to changes in RNA reactivity and function. © 2014 Wiley Periodicals, Inc. Biopolymers 103: 167–174, 2015.

show abstract

“…The high energy barriers in the transition states encountered upon addition of O 2 onto the C8positionoft he A-ring are thought to block this pathway. [34] The oxidationo f8 -oxoA was recently explored [35] and it was shownt hat oxidative conditions induced nucleophilic addition at the C2-position in the presence of N-bromosuccinimide or Na 2 IrCl 6 as oxidants. [33] Ta king into consideration that the redoxp otential for 8-oxo-7,8-dihydro-2'-deoxy adenosine (8-oxodA) has been measured to be 0.89 Vv s. NHE (expectedt ob eu nchanged for the corresponding ribonucleoside), it is reasonable to expect that this lesion may undergo as imilar fate.…”

Section: Generation and Reactivity Of 8-oxoamentioning

confidence: 95%

8‐Oxo‐7,8‐dihydroadenine and 8‐Oxo‐7,8‐dihydroadenosine—Chemistry, Structure, and Function in RNA and Their Presence in Natural Products and Potential Drug Derivatives

Choi

Chang

Gibala

et al. 2017

Chemistry A European J

View full text Add to dashboard Cite

A description and history of the role that 8-oxo-7,8-dihydroadenine (8-oxoAde) and 8-oxo-7,8-dihydroadenosine (8-oxoA) have in various fields has been compiled. This Review focusses on 1) the formation of this oxidatively generated modification in RNA, its interactions with other biopolymers, and its potential role in the development/progression of disease; 2) the independent synthesis and incorporation of this modified nucleoside into oligonucleotides of RNA to display the progress that has been made in establishing its behavior in biologically relevant systems; 3) reported synthetic routes, which date back to 1890, along with the progress that has been made in the total synthesis of the nucleobase, nucleoside, and their corresponding derivatives; and 4) the isolation, total synthesis, and biological activity of natural products containing these moieties as the backbone. The current state of research regarding this oxidatively generated lesion as well as its importance in the context of RNA, natural products, and potential as drug derivatives is illustrated using all available examples reported to date.

show abstract

Oxidation of Adenosine and Inosine: The Chemistry of 8-Oxo-7,8-dihydropurines, Purine Iminoquinones, and Purine Quinones as Observed by Ultrafast Spectroscopy

Cited by 27 publications

References 67 publications

Analytics of oxidative stress markers in the early diagnosis of oxygen DNA damage

Analytics of oxidative stress markers in the early diagnosis of oxygen DNA damage

Biophysical properties and thermal stability of oligonucleotides of RNA containing 7,8‐dihydro‐8‐hydroxyadenosine

8‐Oxo‐7,8‐dihydroadenine and 8‐Oxo‐7,8‐dihydroadenosine—Chemistry, Structure, and Function in RNA and Their Presence in Natural Products and Potential Drug Derivatives

Contact Info

Product

Resources

About