The Hydrolytic Stability of Hydroxypropano Adducts of 2'-Deoxyguanosine Formed by Reaction with Acrolein and Crotonaldehyde.

Mikkola, Satu; Andersson, Sanna; Hakala, Kristo; Antoni, Gunnar; Björkman, Margareta; Forngren, Benita H.; Forngren, Tobias; Hartvig, Per; Markides, Karin E.; Yngve, Ulrika; Ögren, Mattias

doi:10.3891/acta.chem.scand.53-0642

Cited by 4 publications

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“…22) In the ESI-MS analysis of the adducts, considerably high efficiency of ionization was achieved for the corresponding base forms, compared with the corresponding nucleoside forms, to achieve highly sensitive detection of the adducts. 24,25) In this work also, HPLC-ESI-MS has been employed for quantification of the CPr-Gua adduct in evaluation of the reactivity of DNA with AA and CA. Additionally, we have employed a semi-micro HPLC in place of the conventional HPLC to result in improvement of sensitivity of this method.…”

Section: -7)mentioning

confidence: 99%

LC-MS Study on the Formation of Cyclic 1,N2-Propano Guanine Adduct in the Reactions of DNA with Acetaldehyde in the Presence of Histone

Inagaki

Esaka

Goto

et al. 2004

Biological & Pharmaceutical Bulletin

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Acetaldehyde (AA) and crotonaldehyde (CA, 2-butenal in IUPAC nomenclature) are reactive, ubiquitous aldehydes, which are present in the environment, and the strong carcinogenic property of CA has been confirmed and the carcinogenicity of AA has been strongly suspected. 1-7)CA reacts with the exocyclic amino group of guanine in DNA to form cyclic 1,N 2 -propano guanine (CPr-Gua) adduct as a main DNA adduct. 8,9) The structure of CPr-Gua is shown in Fig. 1. The exogenous exposure of humans to CA can occur by inhalation of cigarette smoke or automobile exhaust gases. A substantial amount of the CPr-Gua adducts has also detected in oral tissue DNA, with increased amounts in cigarette smokers.10) On the other hand, using a highly sensitive 32 P-postlabeling method, CPr-Gua has been detected in a variety of tissues of untreated rats and mice and in human liver, mammary glands and leukocytes, and this will be in part ascribed to CA arising from endogeneous lipid peroxidation.11-13) Thus, the "CA-derived" CPr-Gua adducts will have both exogenous and endogeneous sources.The main source of exposure to AA for the majority of the general population is through the metabolism of alcohol from drinks. It is formed endogenously as a primary product during the metabolic oxidation of ethanol by alcohol dehydrogenases in the liver. The N 2 -ethylguanine (Et-Gua, see Fig. 1) adduct was detected in granulocyte and lymphocyte DNA of alcoholic patients and this adduct has been considered to be a major DNA adduct by AA. [14][15][16][17][18][19] There is a possibility that Et-Gua would induce G-C transversion in vivo. 18,19) On the other hand, recently, the CPr-Gua adduct also has been considered to be another major DNA adduct of AA. [20][21][22] This adduct is considered to cause either base substitution or frameshift mutations.11) Wang et al. reported that the CPr-Gua adduct was formed in reactions of 2Ј-deoxyguanosine (dG) or calf thymus DNA with AA. 20) In our previous work, formation of the CPr-Gua adducts was observed in DNA of cultured HL-60 cells exposed to AA. 22)Wang et al. suggested that there are two path ways to the CPr-Gua adduct, namely, that from CA formed by the aldol condensation of AA and that from consecutive reaction of two molecules of AA. 20) One of the co-authors (M.S.) has reported that the reactions of guanine nucleosides and nucleotides with AA are significantly accelerated under mild conditions by addition of some basic amino acids such as arginine and lysine to give the corresponding cyclic 1,N 2 -propano derivatives almost quantitatively.21) Both aldol condensation of AA to CA and the formation of the CPr-Gua adduct from CA would be accelerated strongly by the added basic amino acids.Is there any biological meaning to this remarkable acceleration by the basic amino acids?-This is a question which is the major subject of this work. We hypothesized that the basic amino acids may be those in histone. Histone is essential for DNA packaging and contains a large amount of basic amino acids such as arginine and lys...

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Section: -7)mentioning

confidence: 99%

LC-MS Study on the Formation of Cyclic 1,N2-Propano Guanine Adduct in the Reactions of DNA with Acetaldehyde in the Presence of Histone

Inagaki

Esaka

Goto

et al. 2004

Biological & Pharmaceutical Bulletin

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“…The estradiol benzoate and oxytocin were used to cause PD model in this paper (Hu & Jin, 1999;Huang et al, 2016;Liu et al, 2011). In the present study, we aimed to investigate the protective effect of bergamot essential oil, juice, and ethanol extract on primary dysmenorrhea in rats.…”

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Essential oil, juice, and ethanol extract from bergamot confer improving effects against primary dysmenorrhea in rats

et al. 2021

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Oxidative hydrolysis of a cyclic 1,N2-propano-2′-deoxyguanosine, an adduct of 2′-deoxyguanosine with acetaldehyde or crotonaldehyde

Sako

Inagaki

Esaka

et al. 2003

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The Hydrolytic Stability of Hydroxypropano Adducts of 2'-Deoxyguanosine Formed by Reaction with Acrolein and Crotonaldehyde.

Cited by 4 publications

References 0 publications

LC-MS Study on the Formation of Cyclic 1,N2-Propano Guanine Adduct in the Reactions of DNA with Acetaldehyde in the Presence of Histone

LC-MS Study on the Formation of Cyclic 1,N2-Propano Guanine Adduct in the Reactions of DNA with Acetaldehyde in the Presence of Histone

Essential oil, juice, and ethanol extract from bergamot confer improving effects against primary dysmenorrhea in rats

Oxidative hydrolysis of a cyclic 1,N2-propano-2′-deoxyguanosine, an adduct of 2′-deoxyguanosine with acetaldehyde or crotonaldehyde

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