Reaction of malondialdehyde with guanine nucleosides:  formation of adducts containing oxadiazabicyclononene residues in the base-pairing region

Marnett, Lawrence J.; Basu, Ashis K.; O'Hara, Shawn M.; Weller, Paul; Rahman, A.; Oliver, John P.

doi:10.1021/ja00266a065

Cited by 80 publications

(59 citation statements)

References 2 publications

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“…The electrophiles generated from lipid peroxidation, such as malondialdehyde (MDA) and 4-hydroxynonenal (HNE), may react with DNA bases. MDA modifies purine bases to generate a tricyclic adduct with guanine (47) and an acyclic adduct with adenine (48). HNE reacts directly with 2′-deoxyguanosine to produce a tricyclic substituted propane adduct and is readily oxidized to the epoxide derivative, which can covalently modify both 2′-deoxyguanosine and 2′-deoxyadenosine to form etheno adducts (49).…”

Section: Discussionmentioning

confidence: 99%

Dietary fish oil and vitamin E enhance doxorubicin effects in P388 tumor‐bearing mice

Liu

Tan

2002

Lipids

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In this study, four kinds of rodent diets, CO, FO, CVe, and FVe, were used by addition of canola oil, oil mixture (fish oil + canola oil), canola oil plus vitamin E, and oil mixture plus vitamin E, respectively, to a basic diet, AIN-93G, to investigate the influence of dietary fish oil and vitamin E on doxorubicin (DOX) treatment in P388 ascitic mice. Animal life span (LS) and heart damage were recorded in mice fed the four different diets and treated with different doses of DOX. The optimal doses of DOX for antitumor effect as manifested by increased LS were 6.0 and 9.0 mg/kg. Both fish oil and vitamin E significantly enhanced this effect. On the other hand, DOX at 12.0 mg/kg induced severe heart damage, which was also significantly aggravated by both fish oil and vitamin E, as shown by both decreased LS and increased serum creatine phosphokinase activity. Fish oil and vitamin E appeared to enhance the antitumor effect of optimal doses of DOX but to aggravate cardiotoxicity owing to DOX overdose.

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Section: Discussionmentioning

confidence: 99%

Dietary fish oil and vitamin E enhance doxorubicin effects in P388 tumor‐bearing mice

Liu

Tan

2002

Lipids

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“…An example is provided by the lipid-DNA damage derived from the reaction of malondialdehyde (MDA) with cytosine, adenine or guanine deoxynucleosides. 1,2 Tandem damage processes are very harmful in biological systems and may generate highly diffusible radical species in a certain cell compartment, which are then able to reach other target sites, producing molecular species with potent biological effects. 3 Recently, a tandem radical damage involving polypeptide and lipid molecules has been evidenced for Met-containing protein and peptide substrates in the presence of unsaturated membrane phospholipids.…”

Section: Introductionmentioning

confidence: 99%

The Reductive Desulfurization of Met and Cys Residues in Bovine RNase A Is Associated with trans Lipids Formation in a Mimetic Model of Biological Membranes

et al. 2008

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Damage to bovine pancreatic RNase A, due to the H* atom and/or solvated electron attack at protein sulfur-containing residues, was investigated by Raman spectroscopy and mass spectrometry techniques. To the already known desulfurization process affecting Met residues, novel reactivity was observed involving disulfide moieties, leading to the chemical transformation of Cys into Ala residues. Mapping experiments demonstrated that desulfurization selectively affected Met79, Cys110, Cys58 and Cys72 during first stages of reaction. While this reaction was performed on protein species added to large unilamellar vescicles, desulfurization yielded sulfur radicals able to induce a cis-trans isomerization of lipids at the onset of irradiation. These findings reveal new scenarios on reactions generated by radical stressing conditions, suggesting the need for specific assays and for future investigations to detect these modifications in proteins and lipids within challenged cells.

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“…MDA reacts with DNA as a bis-electrophile to form the exocyclic guanine adduct M 1 G 1 [3-(2′-deoxy--D-erythro-pentofuranosyl)pyrimido[1,2-a]-purin-10(3H)-one] (4)(5)(6)(7)(8). M 1 G also arises as a consequence of DNA oxidative damage, resulting in the formation of base propenals that can transfer their oxopropenyl group to deoxyguanosine (9) (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Structure of an Oligodeoxynucleotide Containing a 1,N²-Propanodeoxyguanosine Adduct Positioned in a Palindrome Derived from the Salmonella typhimurium hisD3052 Gene: Hoogsteen Pairing at pH 5.2

Weisenseel

Reddy

Marnett

et al. 2002

Chem. Res. Toxicol.

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The structure of the 1,N(2)-Propanodeoxyguanosine (PdG) adduct was determined at pH 5.2 in the oligodeoxynucleotide duplex 5'-d(CGCGGTXTCCGCG)3'.5'-d(CGCGGACACCGCG)-3' (X = PdG). This sequence, referred to as the -TXT- sequence, is contained within the Salmonella typhimurium hisD3052 gene and contains a palindrome, representing a potential hotspot for frameshift mutagenesis. PdG provides a model for the primary adduct induced in DNA by malondialdehyde, the 3-(2'-deoxy-beta-D-erythro-pentofuranosyl)pyrimido[1,2-a]-purin-10(3H)-one (M(1)G) lesion. The solution structure was refined by molecular dynamics calculations restrained by a combination of NMR-derived distances and dihedral angles, using a simulated annealing protocol. PdG introduced a localized perturbation into the sequence at base pair X(7).C(20), which was pH-dependent. At neutral pH, conformational exchange resulted in spectral line broadening, and it was not possible to determine the structure. A stable structure was observed at pH 5.2 in which PdG rotated about the glycosyl bond into the syn conformation. This placed the exocyclic moiety into the major groove of the duplex. PdG formed a protonated Hoogsteen pair with nucleotide C(20) in the complementary strand. The pseudorotation of the deoxyribose at C(20) was altered to an approximately equal blend of C2'-endo and C3'-endo structures. However, these made little difference in the overall structure of the modified oligodeoxynucleotide. The structure was compared to that of PdG in the 5'-d(CGCXCGGCATG)-3'.5'-(CATGCCGCGCG)-3' sequence (the -CXC- sequence) at pH 5.8 [Singh, U. S., Moe, J. G., Reddy, G. R., Weisenseel, J. P., Marnett, L. J., and Stone, M. P. (1993) Chem. Res. Toxicol. 6, 825-836]. A sequence effect was observed. When PdG was placed into the -TXT- sequence at low pH, the structural perturbation was limited to the X(7).C(20) base pair. In contrast, when PdG was placed into the -CXC- sequence at low pH, both the modified base pair and its 3'-neighbor base pair were disrupted. The results are discussed in the context of differential outcomes for site-specific mutagenesis and replication bypass experiments when PdG was placed in the -TXT- and -CXC- sequences, respectively.

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Reaction of malondialdehyde with guanine nucleosides: formation of adducts containing oxadiazabicyclononene residues in the base-pairing region

Cited by 80 publications

References 2 publications

Dietary fish oil and vitamin E enhance doxorubicin effects in P388 tumor‐bearing mice

Dietary fish oil and vitamin E enhance doxorubicin effects in P388 tumor‐bearing mice

The Reductive Desulfurization of Met and Cys Residues in Bovine RNase A Is Associated with trans Lipids Formation in a Mimetic Model of Biological Membranes

Structure of an Oligodeoxynucleotide Containing a 1,N²-Propanodeoxyguanosine Adduct Positioned in a Palindrome Derived from the Salmonella typhimurium hisD3052 Gene: Hoogsteen Pairing at pH 5.2

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Reaction of malondialdehyde with guanine nucleosides: formation of adducts containing oxadiazabicyclononene residues in the base-pairing region

Cited by 80 publications

References 2 publications

Dietary fish oil and vitamin E enhance doxorubicin effects in P388 tumor‐bearing mice

Dietary fish oil and vitamin E enhance doxorubicin effects in P388 tumor‐bearing mice

The Reductive Desulfurization of Met and Cys Residues in Bovine RNase A Is Associated with trans Lipids Formation in a Mimetic Model of Biological Membranes

Structure of an Oligodeoxynucleotide Containing a 1,N2-Propanodeoxyguanosine Adduct Positioned in a Palindrome Derived from the Salmonella typhimurium hisD3052 Gene: Hoogsteen Pairing at pH 5.2

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Structure of an Oligodeoxynucleotide Containing a 1,N²-Propanodeoxyguanosine Adduct Positioned in a Palindrome Derived from the Salmonella typhimurium hisD3052 Gene: Hoogsteen Pairing at pH 5.2