Studies on the interactions between DNA and flavins

Kuratomi, Kazuoki; Kobayashi, Yasuko

doi:10.1016/0005-2787(77)90004-1

Cited by 26 publications

(5 citation statements)

References 17 publications

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“…The weak affinity of RB for nucleic acid is consistent with the finding of Kuratomi and Kobayashi (16) that only one RB molecule is bound to every 500 nucleotide base pairs of DNA in solutions of low ionic strength. Weak RB–DNA binding is also consistent with reports that RB sensitizes the formation of both RB–nucleic acid adducts and single strand breaks (17,18).…”

Section: Discussionsupporting

confidence: 89%

Binding Affinities of Commonly Employed Sensitizers of Viral Inactivation¶

Dardare¹,

Platz²

2007

Photochemistry and Photobiology

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Methylene blue (MB), riboflavin (RB) and psoralen sensitizers (4′ aminomethyl‐4,5′,8‐trimethylpsoralen [AMT] and derivatives) are under study as sensitizers of viral inactivation of blood products such as plasma proteins, platelets and red cells, all of which lack genomic nucleic acid. To predict where these sensitizers accumulate in viruses and in cells, their relative affinities for calf thymus DNA, neutral and negatively charged phospholipids and albumin were determined by dialysis. MB has a strong affinity for nucleic acid and negatively charged phospholipid, but little affinity for albumin or neutral phospholipid. RB has modest affinity for nucleic acid and little affinity for albumin or either phospholipid. AMT has substantial affinity for nucleic acid, neutral and negatively charged phospholipids and albumin. Neither AMT nor RB binds to poly G, although MB has some affinity for this polymer. Evidence of association of RB with guanosine monophosphate, adenosine monophosphate and tryptophan methylester hydrochloride in PBS buffer in the presence and absence of formamide was obtained from nonlinear Stern–Volmer plots and shifts in the ground state absorption spectrum of RB.

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Section: Discussionsupporting

confidence: 89%

Binding Affinities of Commonly Employed Sensitizers of Viral Inactivation¶

Dardare¹,

Platz²

2007

Photochemistry and Photobiology

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“…22 Furthermore, Rb is a planar, conjugated ring structure with a sugar side chain. In accord with the previous work on binding of lumiflavin to DNA by intercalation, 23 the planar portion of Rb is capable of intercalating between the bases of nucleic acids thereby enabling to inject hole into the base at intercalation site triggering hole migration and trapping at low oxidation potential sequences, Gs in duplex DNA 10 or G/U site in duplex RNA, 24-25 resulting in strand breaks upon photosensitization. The complete set of reactivity data of nucleotides towards one-electron oxidation by 3 Rb* has offered a basic mechanism for further understanding of Rb photochemistry involved in skin damage and pathogen inactivation.…”

Section: Discussionsupporting

confidence: 71%

Reaction mechanisms of riboflavin triplet state with nucleic acid bases

Wang

et al. 2006

Photochem Photobiol Sci

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ESR and laser flash photolysis studies have determined a reasonable order of reactivity of nucleotides with triplet riboflavin (3Rb*) for the first time. ESR detection of triplet state reactivity of Rb with nucleoside, polynucleotide and DNA has been obtained simultaneously. In addition, ESR spin elimination measurement of the reactivity of 3Rb* with nucleotides in good accord with laser flash photolysis determination of the corresponding rate constants offers a simple and reliable method to detect the reactivities of nucleic acids and its components with photoexcited flavins. Kinetic, ESR and thermodynamic studies have demonstrated that Rb should be a strong endogenous photosensitizer capable of oxidizing all nucleic acid bases, and preferentially two purine nucleotides with high rate constants.

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“…The extent of our interest in RB as a pathogen reduction agent for blood stems from more than 70 years of research literature that details vitamin B 2 's chemistry, toxicology and the in vitro and in vivo ability to sensitize the photochemistry of nucleic acids (19–21). RB is known to associate with nucleic acids, possibly by intercalation (21,22). Furthermore, it is known to cause lesions in DNA by both Type I and II photochemical reactions.…”

Section: Introductionmentioning

confidence: 99%

Riboflavin and UV‐Light Based Pathogen Reduction: Extent and Consequence of DNA Damage at the Molecular Level

Kumar¹,

Lockerble²,

Kell³

et al. 2004

Photochem & Photobiology

101

133

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We are developing a technology based on the combined application of riboflavin (RB) and light for inactivating pathogens in blood products while retaining the biological functions of the treated cells and proteins. Virus and bacteria reduction measured by tissue culture infectivity or colony formation with UV light alone and in combination with RB yield equivalent results. The effects of RB as a sensitizing agent on DNA in white cells, bacteria and viruses in combination with UV light exposure have been evaluated. UV-mediated DNA degradation in Jurkat T cells and leukocytes in plasma as measured by the FlowTACS assay was significantly increased in the presence of RB. Agarose gel electrophoretic analysis of DNA in Escherichia coli and leukocytes in plasma demonstrated enhanced DNA degradation in the presence of RB. UV light in combination with RB prevented the reactivation of lambda phage compared with samples irradiated in the absence of RB. UV-mediated oxidative damage in calf thymus DNA was also enhanced in the presence of RB. These observations clearly demonstrate that the presence of RB and UV light selectively enhances damage to the guanine bases in DNA. These data also suggest that the type and extent of damage to DNA for virus in the presence of RB and light make it less likely to be repaired by normal repair pathways available in host cells.

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Studies on the interactions between DNA and flavins

Cited by 26 publications

References 17 publications

Binding Affinities of Commonly Employed Sensitizers of Viral Inactivation¶

Binding Affinities of Commonly Employed Sensitizers of Viral Inactivation¶

Reaction mechanisms of riboflavin triplet state with nucleic acid bases

Riboflavin and UV‐Light Based Pathogen Reduction: Extent and Consequence of DNA Damage at the Molecular Level

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