Inhibition of Restriction Enzyme's DNA Sequence Recognition by PUVA Treatment†¶

Hanawa, Fujinori; Okamoto, Mamoru; Towers, G.H.N.

doi:10.1562/0031-8655(2001)074<0269:ioreds>2.0.co;2

Cited by 4 publications

(9 citation statements)

References 20 publications

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“…To determine photosensitized DNA-binding activities of these compounds with UVA irradiation, they were subjected to a photosensitized DNA-binding assay using a 1.5 kb DNA fragment and restriction enzymes previously developed by our group (16). The DNA fragment is shown in Fig.…”

Section: Photosensitized Dna-binding Activitiesmentioning

confidence: 99%

“…A thin-layer chromatography (TLC) overlay bioassay and structural elucidation by standard spectroscopic methods were used. In addition, the isolated compounds were subjected to a DNA-binding test developed by our group using a specially designed DNA fragment and restriction enzymes (16). The results of this binding test are also presented.…”

Section: Introductionmentioning

confidence: 99%

“…Photosensitized DNA‐binding test ( 16 ) The 1.5 kb DNA fragment (100 ng) was mixed with 1 nmol of isolated compounds (500 μ M in 5% ethanol) in a microcentrifuge tube. The total volume was adjusted to 8 μL with water.…”

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confidence: 99%

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Antimicrobial DNA-binding Photosensitizers from the Common Rush, Juncus effusus¶

Hanawa

Okamoto

Towers

2002

Photochemistry and Photobiology

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Our continuing survey of phototoxins from higher plants has led to the isolation and identification from the common rush, Juncus effusus L., of the phenanthrene, dehydroeffusol (1), and the dihydrophenanthrene, juncusol (2), compounds that display enhanced antimicrobial activities in light. The antimicrobial activities (minimum inhibitory concentrations) for these compounds against methicillin‐resistant and ‐sensitive Staphylococcus aureus and Candida albicans were increased 16‐ and two‐fold, respectively, by irradiation with ultraviolet A (UVA). Photosensitized DNA‐binding activities (as possible covalent bond formation) of these compounds were determined by using restriction enzymes and a specially prepared 1.5 kb DNA fragment. Under UVA irradiation, dehydroeffusol strongly inhibited all the restriction enzymes (KpnI, XbaI, PmeI, DraI, PacI and BciVI) that have at least one 5′‐TpA sequence in their recognition sites. Weak inhibitions were found for the restriction enzymes EcoRI, SacI, BamHI, SalI, PstI and HindIII, which do not possess a 5′‐TpA sequence at their restriction sites and the restriction site sequences of which consist of all bases, A, T, G and C. Trace or no inhibition was found for AscI and SmaI, the restriction site sequences of which are composed of only C and G. The results indicate the necessity of thymine (adenine) for the photosensitized DNA‐binding activity of dehydroeffusol. A strong inhibition against SphI, which does not have a 5′‐TpA sequence in the restriction sequence, indicates that there are possibly other binding sequence(s) for dehydroeffusol. With juncusol and UVA, strong inhibitions for KpnI and BciVI and trace inhibitions for PacI, XbaI, PmeI and DraI were found. This result also showed a preference of juncusol for 5′‐TpA, but the preference could be more selective than that of dehydroeffusol depending on the surrounding sequences of 5′‐TpA in the respective restriction sites. A strong inhibition of SphI by juncusol with UVA also indicated the existence of an unknown binding sequence for this compound. Generally, the DNA‐binding activity of this compound was weaker than that of dehydroeffusol.

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Section: Photosensitized Dna-binding Activitiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Antimicrobial DNA-binding Photosensitizers from the Common Rush, Juncus effusus¶

Hanawa

Okamoto

Towers

2002

Photochemistry and Photobiology

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“…During the course of our survey for novel photo-active compounds of potential use in photochemotherapy, we recently reported on phenanthrene-type photoactive antimicrobial compounds from the underground part of the common rush, Juncus effuses [11]. These compounds also show photo-activated DNA binding activities to the 5¢-TpA sequences of a DNA fragment in a manner similar to those of one of the psoralens, 8-MOP [12]. Here, we report on photo-activated antimicrobial and DNA binding activities of furoquinolines, skimmianine, kokusaginine, haplopine and a pyranoquinolone, flindersine ( Fig.…”

mentioning

confidence: 88%

“…Photo-activated DNA binding assay Photo-activated DNA binding assays were carried out as described [12] with small modifications. The 1.5-kb DNA fragment (100 ng) was mixed with 1 nmol of the compounds (2 mL from a 500 mM 2.5 % DMSO solution) in a 1.5-mL microcentrifuge tube.…”

Section: Tlc Overlay Assaymentioning

confidence: 99%

Photo-Activated DNA Binding and Antimicrobial Activities of Furoquinoline and Pyranoquinolone Alkaloids from Rutaceae

2004

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To find novel photo-active compounds of potential use in photochemotherapy from higher plants, photo-activated antimicrobial and DNA binding activities of the furoquinolines, skimmianine, kokusaginine, and haplopine, and a pyranoquinolone, flindersine, from two species of Rutaceae plants were investigated. TLC overlay assays against a methichillin-resistant strain of Staphylococcus aureus and Candida albicans were employed to test antimicrobial properties. All of the tested compounds showed photo-activated antimicrobial activity against S. aureus in the order of kokusaginine > haplopine, flindersine > skimmianine. Weaker activity was found for C. albicans. Photo-activated DNA binding activity of these compounds was investigated by a method using restriction enzymes and a specially designed 1.5 kb DNA fragment. Kokusaginine showed inhibition against all of the 16 restriction enzymes. Haplopine showed a similar inhibition pattern but the binding activity against Asc I and Sma I with restriction sequences consisting only of G and C was very weak. Skimmianine showed binding activity against Xba I, BciV I, Sal I, Pst I, Sph I and Hind III, but very weak or no activity was found for the other restriction enzymes. A pyranoquinolone, flindersine, showed no activity against any of the restriction enzymes. Photo-activated DNA binding activity of furoquinolines was therefore in the order of kokusaginine > haplopine > skimmianine, which was the same order as their photo-activated antimicrobial activity against S. aureus. Therefore, it was concluded that DNA is one of the cellular targets for the furoquinolines to exert their biological activities, similar to psoralens. However, because flindersine showed photo-activated antimicrobial activity against S. aureus but did not show photo-activated DNA binding activity, it is clear that there are other cellular target components for this compound to exert photo-toxic activity.

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Antimicrobial DNA-binding Photosensitizers from the Common Rush, Juncus effusus¶

Hanawa

Okamoto

Towers

2002

Photochem Photobiol

View full text Add to dashboard Cite

Our continuing survey of phototoxins from higher plants has led to the isolation and identification from the common rush, Juncus effusus L., of the phenanthrene, dehydroeffusol (1), and the dihydrophenanthrene, juncusol (2), compounds that display enhanced antimicrobial activities in light. The antimicrobial activities (minimum inhibitory concentrations) for these compounds against methicillin-resistant and -sensitive Staphylococcus aureus and Candida albicans were increased 16- and two-fold, respectively, by irradiation with ultraviolet A (UVA). Photosensitized DNA-binding activities (as possible covalent bond formation) of these compounds were determined by using restriction enzymes and a specially prepared 1.5 kb DNA fragment. Under UVA irradiation, dehydroeffusol strongly inhibited all the restriction enzymes (KpnI, XbaI, PmeI, DraI, PacI and BciVI) that have at least one 5'-TpA sequence in their recognition sites. Weak inhibitions were found for the restriction enzymes EcoRI, SacI, BamHI, SalI, PstI and HindIII, which do not possess a 5'-TpA sequence at their restriction sites and the restriction site sequences of which consist of all bases, A, T, G and C. Trace or no inhibition was found for AscI and SmaI, the restriction site sequences of which are composed of only C and G. The results indicate the necessity of thymine (adenine) for the photosensitized DNA-binding activity of dehydroeffusol. A strong inhibition against SphI, which does not have a 5'-TpA sequence in the restriction sequence, indicates that there are possibly other binding sequence(s) for dehydroeffusol. With juncusol and UVA, strong inhibitions for KpnI and BciVI and trace inhibitions for PacI, XbaI, PmeI and DraI were found. This result also showed a preference of juncusol for 5'-TpA, but the preference could be more selective than that of dehydroeffusol depending on the surrounding sequences of 5'-TpA in the respective restriction sites. A strong inhibition of SphI by juncusol with UVA also indicated the existence of an unknown binding sequence for this compound. Generally, the DNA-binding activity of this compound was weaker than that of dehydroeffusol.

show abstract

Inhibition of Restriction Enzyme's DNA Sequence Recognition by PUVA Treatment†¶

Cited by 4 publications

References 20 publications

Antimicrobial DNA-binding Photosensitizers from the Common Rush, Juncus effusus¶

Antimicrobial DNA-binding Photosensitizers from the Common Rush, Juncus effusus¶

Photo-Activated DNA Binding and Antimicrobial Activities of Furoquinoline and Pyranoquinolone Alkaloids from Rutaceae

Antimicrobial DNA-binding Photosensitizers from the Common Rush, Juncus effusus¶

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