Sequence-specific DNA damage induced by ultraviolet A-irradiated folic acid via its photolysis product

Hirakawa, Kazuhiko; Suzuki, Hiroyuki; Oikawa, Shinji; Kawanishi, Shosuke

doi:10.1016/s0003-9861(02)00722-1

Cited by 94 publications

(87 citation statements)

References 45 publications

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“…Vitamin B9 plays a crucial role in various metabolic and biochemical processes such as the replication of DNA and cell division, notably during the early stages of embryology (Herrmann & Obeid, 2011;Lucock, 2000). This bioactivity is mostly due to the native form of B9 (Gazzali et al, 2016;Hirakawa, Suzuki, Oikawa, & Kawanishi, 2003;Patro, Adhikari, Mukherjee, & Chattopadhyay, 2005). To prepare biocarriers that maintain the bioactivity of the vitamin, it is therefore critical to preserve its chemical integrity.…”

Section: Discussionmentioning

confidence: 99%

Coacervates of whey proteins to protect and improve the oral delivery of a bioactive molecule

Chapeau

Bertrand

Briard‐Bion

et al. 2017

Journal of Functional Foods

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a b s t r a c tThe potentiality of heteroprotein complex coacervates as biocarrier for a bioactive was investigated. Vitamin B9 (B9), also known as folic acid, was encapsulated by complex coacervation of two whey proteins (WP), b-lactoglobulin and lactoferrin. The stability and bioavailability of formed B9-WP coacervates was then characterized. Under degradative conditions in vitro (UV light irradiation, and oxidation by H 2 O 2 ), WP coacervates protected the vitamin against chemical degradation. B9-WP coacervates also showed considerable physical stability over time when incorporated in real food matrices. Compared to unencapsulated B9, oral administration of B9-WP coacervates to healthy rats enhanced the plasma level of the vitamin. This improved bioavailability can be ascribed to the improvement in the solubility of B9 throughout the gastro-intestinal tract. We thus demonstrate the efficiency of WP coacervates as biocarrier for the protection and delivery of small bioactive molecules.

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Section: Discussionmentioning

confidence: 99%

Coacervates of whey proteins to protect and improve the oral delivery of a bioactive molecule

Chapeau

Bertrand

Briard‐Bion

et al. 2017

Journal of Functional Foods

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“…The fluorescence spectrum of UV-irradiated folic acid was quite similar to that of pterine-6-carboxylic acid, which is a strong fluorescence molecule. But the pteridine moiety of folic acid shows very weak fluorescence, which is due to an intramolecular electron transfer from the p-aminobenzoyl-glutamic acid moiety to the pteridine moiety [27,28].…”

Section: The Chemiluminescence Mechanism Of Pga In the Pms/co(ii) Systemmentioning

confidence: 99%

Determination of folic acid by chemiluminescence based on peroxomonosulfate-cobalt(II) system

Zhang

Zhao

Lin

2008

Talanta

116

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Based on the chemiluminescence (CL) phenomena of folic acid in peroxomonosulfate-cobalt(II) system, a rapid and sensitive CL method was developed for determination of folic acid in pharmaceutical preparations and its urinary metabolism processes. Under the optimum conditions, the relative CL intensity was linear over the concentration ranging from 10 −9 to 8 × 10 −7 mol L −1 (R 2 = 0.9991) with a detection limit as low as 6 × 10 −10 mol L −1 (S/N = 3) and relative standard deviation was 2.63% for 2 × 10 −8 mol L −1 folic acid (n = 11). This method has been successfully applied to the determination of folic acid in tablets and human urine. The blank CL emission was yielded owing to the formation of singlet oxygen molecular pair from the quenching experiment of 1,4-diazabicyclo[2.2.2]octane, and pterine-6-carboxylic acid might be the degradation intermediate in this system and it also acts an energy acceptor and sensitizes the chemiluminescence based on the studies of the CL and fluorescence spectra.

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“…The electron-loss center created in a DNA duplex by one-electron oxidation ultimately moves to end up at the hole-trapping site via hole migration through the DNA π-stack [2,[5][6][7][8]. Various experimental [4,[9][10][11][12] and theoretical [13,14] studies have revealed that GG, GGG, and GGGG sequences can be the hole-trapping site in the B-form DNA, leading to the formation of oxidative products of guanine. However, the approach to evaluate the genomic DNA damage has not been well established.…”

Section: Introductionmentioning

confidence: 99%

“…UVA radiation induces DNA oxidation through Type I (electron transfer) and Type II (singlet oxygen) mechanisms by activation of various endogenous photosensitizers [1][2][3][4][5][10][11][12] because UVA is hardly absorbed by DNA. UVA frequently induces A-T → C-G transversion, rather than G-C → T-A and G-C → C-G transversions [16,17].…”

mentioning

confidence: 99%

Theoretical study of the effects of amino acids on one-electron oxidation of a nucleobase: adenine residue can be a hole-trapping site

Hirakawa¹,

Yoshida²

2014

pacs

Self Cite

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DNA damage by oxidative stress has been extensively investigated, but the effect of interaction with histone protein on the DNA oxidation has not been well-understood. The effects of amino acids on DNA oxidation induced by one-electron oxidants were examined by ab initio molecular orbital calculation at Hartree-Fock 6-31G* level. The calculated ionization potentials of nucleobases suggest that guanine is protected by interaction with amino acids from oxidative damage, whereas oxidation of adenine is enhanced through interaction with several kinds of amino acids. These findings suggest that adenine can be easily oxidized under the interaction with certain amino acid in chromatin rather than guanine, which can be most easily oxidized in isolated DNA. The effect of amino acids on DNA oxidation may explain the mutation at adenine residue induced by oxidative stress due to ultraviolet A irradiation.

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Sequence-specific DNA damage induced by ultraviolet A-irradiated folic acid via its photolysis product

Cited by 94 publications

References 45 publications

Coacervates of whey proteins to protect and improve the oral delivery of a bioactive molecule

Coacervates of whey proteins to protect and improve the oral delivery of a bioactive molecule

Determination of folic acid by chemiluminescence based on peroxomonosulfate-cobalt(II) system

Theoretical study of the effects of amino acids on one-electron oxidation of a nucleobase: adenine residue can be a hole-trapping site

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