Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin

Takahashi, Eizo; Fujita, Ken‐ichi; Kamataki, Tetsuya; Arimoto‐Kobayashi, Sakae; Okamoto, Keinosuke; Negishi, Tomoe

doi:10.1016/s0027-5107(02)00212-9

Cited by 82 publications

(54 citation statements)

References 30 publications

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“…[2] Like other anthraquinone dyes, it is a biologically active molecule and has remarkable antigenotoxic activity as an inhibitor of the human recombinant cytochrome P450 isozymes. [3] The natural source of alizarin is the root of the madder plant (Rubia tinctorum). This plant has been cultivated as a dyestuff since antiquity in central Asia and Egypt.…”

Section: Introductionmentioning

confidence: 99%

Analysis of alizarin by surface‐enhanced and FT‐Raman spectroscopy

Baran

Wrzosek

Bukowska

et al. 2008

J Raman Spectroscopy

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This paper presents the application of Raman spectroscopy (RS) for the structural study of alizarin adsorbed on a metallic surface. As a biologically active molecule, alizarin has remarkable antigenotoxic activity like other anthraquinone dyes. Alizarin is highly fluorescent and that limits the application of RS as an investigation method; however, the Fourier transform-RS (FTRS) can be applied since the near-infrared excitation line lies far away from the absorption region of alizarin. The surface enhanced-RS (SERS) technique also makes the fluorescence quenching possible. In this work, monolayers of alizarin were deposited on the surface of an electrode by the immersion of silver substrates in methanolic solution of the analyte. From such prepared samples, by using the excitation of 488, 514.5 and 647.1 nm the Raman spectra were registered. Depending on the excitation line, SERS or surface-enhanced resonance Raman scattering (SERRS) spectra of alizarin were observed. The interpretation of experimental data was supported by theoretical calculations.

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Section: Introductionmentioning

confidence: 99%

Analysis of alizarin by surface‐enhanced and FT‐Raman spectroscopy

Baran

Wrzosek

Bukowska

et al. 2008

J Raman Spectroscopy

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“…AZ as a component of food can act against the action of these carcinogens. 4 AZ is highly fluorescent and practically insoluble in water. These properties seriously limit the application of Raman spectroscopy to carry out a structural study of this molecule, although several Raman studies on AZ can be found in the literature.…”

Section: Introductionmentioning

confidence: 99%

Surface‐enhanced Raman scattering study of the adsorption of the anthraquinone pigment alizarin on Ag nanoparticles

Cañamares

Garcia-Ramos

Domingo

et al. 2004

J Raman Spectroscopy

159

207

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FT-Raman and surface-enhanced Raman scattering (SERS) spectroscopy were applied in the vibrational characterization and study of the adsorption and acidity behavior of the highly fluorescent anthraquinone dye alizarin on Ag colloids prepared by chemical reduction with hydroxylamine hydrochloride. The SERS spectra were obtained at different conditions of pH, excitation wavelength and pigment concentration in order to deduce the adsorption mechanism of this molecule. On the basis of the results found we propose an adsorption model for alizarin, which has a different acidic behavior on the metal surface to that in solution. On the metal the deprotonation order of the OH groups changes with respect to the aqueous solution, the OH in position 1 being the first to be ionized instead of that in position 2 as occurs in solution. The two main alizarin forms identified on the metal surface correspond to the mono-and dianionic alizarin species.

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“…15) Meanwhile, amaranth has not been permitted in U.S.A. since 1976 but is permitted in Japan. Most chemical pigments possess anionic sulfate residues that prevent absorption of the pigments in the gastrointestinal tract.…”

Section: Introductionmentioning

confidence: 99%

Inhibition Mechanism of UDP-Glucuronosyltransferase 1A6 by Xanthene Food Dyes

Uesugi

Furumiya

Mizutani

2006

JOURNAL OF HEALTH SCIENCE

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We have reported that erythrosine (ET), a xanthene dye, inhibited uridine 5-diphosphate (UDP)-glucuronosyltransferase 1A6 (UGT1A6). In order to clarify the structure-inhibition relationships of these xanthene dyes, the inhibitory effect of xanthene dye on human UGT1A6 activity was investigated, such as acid red (AR), ET, phloxine (PL), and rose bengal (RB). ET, PL, and RB strongly inhibited human UGT1A6 activity, with IC 50 values = 0.05, 0.04, and 0.015 mM, respectively. Meanwhile, AR had almost no effect (IC 50 value = 1.7 mM). ET, PL and RB have four halogen atoms on their xanthene backbone, unlike AR. Meanwhile, some contrast media with high halogens on those aromatic compounds, such as ioxaglic acid, iodixanol, meglumine iotalamate, and diatriazole sodium, did not inhibit human UGT1A6 activity. These results suggest that halogens enhance the inhibitory effect of xanthene dyes. In this study, it was proved that xanthene dyes had an inhibitory effect on human UGT1A6 activity by the combination of xanthene structure and halogens on its. Part of this inhibition by xanthene dyes depends the reaction of 1 O 2 originated on xanthene dyes by light irradiation, because the inhibition was prevented by 1 O 2 quenchers, such as NaN 3 and histidine, and in the dark.

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Inhibition of human cytochrome P450 1B1, 1A1 and 1A2 by antigenotoxic compounds, purpurin and alizarin

Cited by 82 publications

References 30 publications

Analysis of alizarin by surface‐enhanced and FT‐Raman spectroscopy

Analysis of alizarin by surface‐enhanced and FT‐Raman spectroscopy

Surface‐enhanced Raman scattering study of the adsorption of the anthraquinone pigment alizarin on Ag nanoparticles

Inhibition Mechanism of UDP-Glucuronosyltransferase 1A6 by Xanthene Food Dyes

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