Photoirradiation products of flavin derivatives, and the effects of photooxidation on guanine

Kino, Katsuhito; Kobayashi, Teruhiko; Arima, Eiji; Komori, Rie; Kobayashi, Tomomi; Miyazawa, Hiroshi

doi:10.1016/j.bmcl.2009.01.112

Cited by 31 publications

(30 citation statements)

References 23 publications

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“…FMF was synthesized by a known method [13]. FMF (28.4 mg, 0.1 mmol) was dissolved in 9 M acetic acid (2.8 mL, Wako Pure Chemical Industries, Ltd., Osaka, Japan).…”

Section: Methodsmentioning

confidence: 99%

“…p-Nitrobenzohydrazide was added to this solution and the mixture was stirred for 3 h at room temperature (Scheme 1). This compound was characterized as the product 1 by NMR ( 1 H-NMR, 13 C-NMR and NOESY), electrospray ionization mass spectrometry (ESI-MS), IR and UV (see Supporting Information). The structure of 1 is shown in Scheme 1.…”

Section: M836 (Page 2)mentioning

confidence: 99%

“…Triazine derivatives directly inhibit the DNA binding of NF-κB [11,12]. Moreover, we synthesized several flavin derivatives [13,14] and tested their inhibitory effects on the DNA binding of NF-κB by performing electrophoretic mobility shift assays (EMSA) as previously reported [11,12]. The title compound,…”

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confidence: 98%

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N'-[2-(7,8-Dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethylidene]-4-nitrobenzohydrazide

Morikawa

Kino

Asada

et al. 2014

Molbank

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The title compound,pteridin-10(2H)-yl)ethylidene]-4-nitrobenzohydrazide (1), was obtained by the reaction of formylmethylflavin and p-nitrobenzohydrazide. The product 1 inhibited the DNA binding of nuclear factor-κB, and was characterized by 1 H-NMR, 13 C-NMR, electrospray ionization mass spectrometry, elemental analysis, IR and UV.Nuclear factor-κB (NF-κB) is a transcription factor which regulates the expression of proteins that play key roles in immunity and inflammation [1][2][3][4]. Consequently, NF-κB is considered a good target for the treatment of many diseases such as cancers and chronic inflammatory diseases [5][6][7][8][9][10]. To find NF-κB inhibitors, we screened our chemical library of small molecule compounds, and found triazine and flavin. Triazine derivatives directly inhibit the DNA binding of NF-κB [11,12]. Moreover, we synthesized several flavin derivatives [13,14] and tested their inhibitory effects on the DNA binding of NF-κB by performing electrophoretic mobility shift assays (EMSA) as previously reported [11,12]. The title compound,

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“…FMF was synthesized by a known method [13]. FMF (28.4 mg, 0.1 mmol) was dissolved in 9 M acetic acid (2.8 mL, Wako Pure Chemical Industries, Ltd., Osaka, Japan).…”

Section: Methodsmentioning

confidence: 99%

Section: M836 (Page 2)mentioning

confidence: 99%

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N'-[2-(7,8-Dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethylidene]-4-nitrobenzohydrazide

Morikawa

Kino

Asada

et al. 2014

Molbank

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“…Additionally, the new chromatogram peaks at 30.5 and 32.1 min in the mixture of after-reaction were the photoirradiation products of riboflavin, not the products of the antioxidation reaction. The previous study [30] has discussed the photoirradiation products of riboflavin in detail, hence there were no more discussions.…”

Section: Screening Of Black Tea Extractsmentioning

confidence: 98%

On‐line HPLC method for screening of antioxidants against superoxide anion radical from complex mixtures

Sun

Chen

et al. 2010

J of Separation Science

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A practical approach for rapidly screening antioxidants against superoxide anion radicals from complex mixtures was developed based on the quantitative difference in active compounds before and after their reaction. To test the effectiveness of the approach, seven flavonoids with antioxidative properties were investigated both individually and in a mixture. Using the approach, antioxidants could be rapidly separated and screened with a ranked order of activities in the meantime. The radical scavenging activities were in the following order: quercetin > kaempferol > fisetin > puerarin > luteolin > rutin > baicalein. The order of activity was conducted by comparing the scavenging ratio of the antioxidant, which was completely consistent with the results obtained from the traditional electronic spin resonance. Then, the method was successfully applied to black tea extracts. This approach is fast and convenient for screening, isolating, and analyzing potential antioxidants from a mixture with good quantitative and reproducible ability.

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“…[2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] The 5 0 -guanine in contiguous guanine sequences, such as GG and GGG, in double-stranded DNA has a lower redox potential than single guanine sequences, and the oxidation of the 5 0 -guanine depends on the localization of the highest occupied molecular orbital (HOMO). 2,3,17 Guanine-rich sequences exist in many important genomic regions, such as telomeres, and these sequences can fold into quadruplex structures.…”

mentioning

confidence: 99%

Calculation of the HOMO localization of Tetrahymena and Oxytricha telomeric quadruplex DNA

Morikawa

Kino

Oyoshi

et al. 2015

Bioorganic & Medicinal Chemistry Letters

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Several guanine-rich sequences exist in many important regions, such as telomeres, and these sequences can form quadruplex DNA structures. It was previously reported that 3'-guanines are mainly oxidized in the Tetrahymena and Oxytricha telomeric quadruplex DNA, d(TGGGGT)4, and 5'-guanines are mainly oxidized in the human telomeric quadruplex DNA, d(TAGGGT)4T. We speculated that the differences in site reactivity between d(TGGGGT)4 and d(TAGGGT)4T are induced by the localization of the HOMO. The HOMOs of the possible quadruplex structures were thus determined and the results showed that the HOMOs of d(TGGGGT)4 +3K(+) and d(TAGGGT)4T +2K(+) localized at the 5'-guanine, and that the HOMO shifted from the 5'-guanine to the 3'-guanine by the addition of a 5'-capping cation. Furthermore, we determined the influence of the cation and demonstrated that localization of the HOMO at the G-quartet plane located immediately adjacent to the cation is disfavored. The calculated HOMO localization of d(TGGGGT)4 +4K(+) and d(TAGGGT)4T +2K(+) matched the experimental results and suggest that d(TGGGGT)4 contains a 5'-capping cation in solution.

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Photoirradiation products of flavin derivatives, and the effects of photooxidation on guanine

Cited by 31 publications

References 23 publications

N'-[2-(7,8-Dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethylidene]-4-nitrobenzohydrazide

N'-[2-(7,8-Dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)ethylidene]-4-nitrobenzohydrazide

On‐line HPLC method for screening of antioxidants against superoxide anion radical from complex mixtures

Calculation of the HOMO localization of Tetrahymena and Oxytricha telomeric quadruplex DNA

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