8-Hydroxydeoxyguanosine formation at the 5' site of 5'-GG-3' sequences in double-stranded DNA by UV radiation with riboflavin

Ito, K.; Inoue, Sumiko; Yamamoto, Kōji; Kawanishi, Shosuke

doi:10.1016/s0021-9258(19)38640-5

Cited by 322 publications

(158 citation statements)

References 34 publications

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“…Using the ESR spin destruction method, Ito et al (1993) presented evidence suggesting that Rf-sensitized site-specific degradation of double-stranded DNA is caused by Rf radicals rather than by 1 O 2 . Under our experimental conditions under which the cells were exposed to UVA in the presence of Rf, it was possible that some Rf penetrated the nuclei and Rf radicals played a partial role in the cytotoxicity.…”

Section: Discussionmentioning

confidence: 99%

“…We postulate that an initial photochemical reaction towards photoaging is absorption of ultraviolet A (UVA) and/or visible radiation by riboflavin (Rf) with consequent production of reactive oxygen species (ROS). Rf, upon irradiation, attacks DNA (Ito et al, 1993), RNA (Tsugita et al, 1965), amino acids (Stoien and Wang, 1974), and protein (Vargas et al, 1982). It has been reported that 8-oxoguanosine is produced by irradiation of DNA in the presence of Rf (Ito et al, 1993).…”

mentioning

confidence: 99%

“…Rf, upon irradiation, attacks DNA (Ito et al, 1993), RNA (Tsugita et al, 1965), amino acids (Stoien and Wang, 1974), and protein (Vargas et al, 1982). It has been reported that 8-oxoguanosine is produced by irradiation of DNA in the presence of Rf (Ito et al, 1993).…”

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confidence: 99%

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Hypoxia Potentiates Ultraviolet A-Induced Riboflavin Cytotoxicity

Minami

Satô

Maeda

et al. 1999

Journal of Investigative Dermatology

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Flavins are thought to be important chromophores for chronic photo-induced skin injury, but the mechanism is not well known. We have reported that the primary cytotoxicity remaining in ultraviolet A-irradiated riboflavin solution is attributable to hydrogen peroxide. Because the dermis is more hypoxic than the atmosphere, we investigated the cytotoxicity of riboflavin solution during and after ultraviolet A irradiation under hypoxia. Riboflavin solution showed stronger cytotoxicity during irradiation under hypoxia than under air. Riboflavin solution that had been irradiated under hypoxia at lower ultraviolet A doses showed stronger cytotoxicity and contained more hydrogen peroxide than solution irradiated under air at the same doses. At higher ultraviolet A doses, however, the cytotoxicity and hydrogen peroxide quantity were similar in riboflavin solutions irradiated under different oxygen conditions. The effect of a singlet oxygen quencher, sodium azide, on the induction of cytotoxicity and production of hydrogen peroxide by ultraviolet A irradiation of riboflavin solution was examined. The presence of sodium azide in the solution during ultraviolet A irradiation suppressed the cytotoxicity and hydrogen peroxide production to similar levels at various ultraviolet A doses regardless of oxygen conditions. At the maximum suppression by sodium azide, hydrogen peroxide production decreased to 10% of the unsuppressed production. About 40% of the oxygen molecules of hydrogen peroxide produced was thought to be derived from oxygen dissolved in the riboflavin solution.

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Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

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Hypoxia Potentiates Ultraviolet A-Induced Riboflavin Cytotoxicity

Minami

Satô

Maeda

et al. 1999

Journal of Investigative Dermatology

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“…ESR experiments suggested that photo-excited riboflavin reacts with dGMP to produce riboflavin anion radical and guanine cation radical, but not with other mononucleotides. The estimated ratio of 8-OH-dG yield to total guanine loss indicates that the photo-excited riboflavin induces 8-OH-dG formation specifically at guanine residues located 5′ to another guanine [ 26 ]. As a result, riboflavin can cause DNA photocleavage by itself on one hand, and it can enhance the ability of all the three compounds to cause DNA photocleavage, on the other.…”

Section: Resultsmentioning

confidence: 99%

Effect of Co-Existing Biologically Relevant Molecules and Ions on DNA Photocleavage Caused by Pyrene and its Derivatives

Wang

2005

IJERPH

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Inorganic ions, coenzymes, amino acids, and saccharides could co-exist with toxic environmental chemicals, such as polycyclic aromatic hydrocarbons (PAHs), in the cell. The presence of these co-existing chemicals can modulate the toxicity of the PAHs. One of the genotoxic effects by PAHs is light-induced cleavage, or photocleavage, of DNA. The effect of inorganic ions I−, Na+, Ca2+, Mg2+, Fe3+, Mn2+, Cu2+, and Zn2+ and biological molecules riboflavin, histidine, mannitol, nicotinamide adenine dinucleotide (NAD), glutathione, and glutamic acid on the DNA photocleavage by pyrene, 1-hydroxypyrene (1-HP), and 1-aminopyrene (1-AP), is studied. The non-transition metal ions Na+, Ca2+, and Mg2+, usually have very little inhibitory effects, while the transition metal ions Fe3+, Cu2+, and Zn2+ enhance, Mn2+ inhibits the DNA photocleavage. The effect by biological molecules is complex, depending on the photochemical reaction mechanisms of the compounds tested (1-AP, 1-HP and pyrene) and on the chemical nature of the added biological molecules. Riboflavin, histidine, and mannitol enhance DNA photocleavage by all three compounds, except that mannitol has no effect on the photocleavage of DNA by pyrene. Glutathione inhibits the DNA photocleavage by 1-AP and 1-HP, but has no effect on that by pyrene. NAD enhances the DNA photocleavage by 1-AP, but has no effect on that by 1-HP and pyrene. Glutamic acid enhances the DNA photocleavage by 1-AP and pyrene, but inhibits that by 1-HP. These results show that the co-existing chemicals may have a profound effect on the toxicity of PAHs, or possibly on the toxicity of many other chemicals. Therefore, if one studies the toxic effects of PAHs or other toxic chemicals, the effect of the co-existing chemicals or ions needs to be considered.

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“…This difference in activity could be explained by favourable guanidinium-phosphate interactions that increase the likelihood of electron transfer events between flavin and guanosine which are known to primarily contribute to DNA cleavage alongside 1 O2-mediated oxidation. 71,72 Therefore, even if the amino-flavin compounds diffuse into the cytoplasm, it is unlikely that damage to constituent nucleic acids would contribute to PDI of the pathogen. 73 Our control compound, riboflavin (Rbf) also exhibits photocleavage of the plasmid (11%) which has been reported previously, 71,72,[74][75][76] however it is clear from the SIM data that, due to its hydrophilic nature and lack of cationic substituent, little cell uptake of the compound is achieved for this to contribute to PDI.…”

Section: Photodynamic Inactivation Of E Colimentioning

confidence: 99%

Tuning Riboflavin Derivatives For Photodynamic Inactivation of Pathogens

Fruk

Crocker

Lee

et al. 2021

Preprint

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The development of effective pathogen reduction strategies is required due to the rise in antibiotic-resistant bacteria and zoonotic viral pandemics. Photodynamic inactivation (PDI) of bacteria and viruses is a potent reduction strategy that bypasses typical resistance mechanisms. Naturally occurring riboflavin has been widely used in PDI applications due to efficient light-induced reactive oxygen species (ROS) release. By rational design of its core structure to alter (photo)physical properties, we obtained derivatives capable of outperforming riboflavin’s visible light-iinduced PDI against E. coli and a SARS-CoV-2 surrogate, revealing functional group dependency for each pathogen. Bacterial PDI was influenced mainly by guanidino substitution, whereas viral PDI increased through bromination of the flavin. These observations were related to enhanced uptake and ROS-specific nucleic acid cleavage mechanisms. Trends in the derivatives’ toxicity towards human fibroblast cells were also investigated to assess viable therapeutic derivatives and help guide further design of PDI agents to combat pathogenic organisms.

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8-Hydroxydeoxyguanosine formation at the 5' site of 5'-GG-3' sequences in double-stranded DNA by UV radiation with riboflavin

Cited by 322 publications

References 34 publications

Hypoxia Potentiates Ultraviolet A-Induced Riboflavin Cytotoxicity

Hypoxia Potentiates Ultraviolet A-Induced Riboflavin Cytotoxicity

Effect of Co-Existing Biologically Relevant Molecules and Ions on DNA Photocleavage Caused by Pyrene and its Derivatives

Tuning Riboflavin Derivatives For Photodynamic Inactivation of Pathogens

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