DNA Cleavage by a Polyethylenimine-appended Porphyrin

Suenaga, Hikaru; Nango, Mamoru; Sugiyama, Tadatsugu; Iwasaki, Toyota; Takeuchi, Yoshito; Shinkai, Seiji

doi:10.1246/cl.2000.306

Cited by 6 publications

(7 citation statements)

References 16 publications

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“…These species have different molecular sizes and complexing characteristics that allow some control on the separation between the DNA duplexes in MX-DNA samples. 28,29,31,32 Figure 7 shows the cross-sectional view of optimized molecular models of SP-DNA, PLL-DNA, and PEI-DNA, and idealized molecular models of DOD-DNA and OCT-DNA complexes. These models show potential geometries and spacing induced by these complexing species in solid samples.…”

Section: Resultsmentioning

confidence: 99%

“…To further probe the role of D ds on the transfer of DNA radicals in MX-DNA solids, the sodium counterion was replaced by various aliphatic amine cations, e.g., spermine tetrahydrochloride (SP), dodecyltrimethylammonium bromide (DOD), and octadecyltrimethylammonium bromide (OCT), and polymeric amine cations, e.g., poly- l -lysine hydrobromide (PLL), and polyethylenimine hydrochloride (PEI). These species have different molecular sizes and complexing characteristics that allow some control on the separation between the DNA duplexes in MX-DNA samples. ,,, Figure shows the cross-sectional view of optimized molecular models of SP-DNA, PLL-DNA, and PEI-DNA, and idealized molecular models of DOD-DNA and OCT-DNA complexes. These models show potential geometries and spacing induced by these complexing species in solid samples.…”

Section: Resultsmentioning

confidence: 99%

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Electron Spin Resonance Study of Electron and Hole Transfer in DNA: Effects of Hydration, Aliphatic Amine Cations, and Histone Proteins

Cai

Sevilla

2001

J. Phys. Chem. B

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In this work, we employ electron spin resonance spectroscopy to investigate the effects of hydration, and various cationic complexing agents, such as, aliphatic amine cations and histone proteins, on electron and hole transfer in DNA. Electrons and holes generated by irradiation at 77 K are trapped on DNA and transfer to a randomly interspersed intercalator, mitoxantrone (MX). Monitoring the changes of ESR signals of MX radicals, one electron oxidized guanine (G • + ), one-electron reduced cytosine [C(N3)H • ], and thymine anion radicals (T • - ) with time at 77 K allows for the direct observation of electron and hole transfer. The apparent transfer distance (D a) in bps is derived from the change in radicals with time and is a measure of the total number of bps within the tunneling range. In all solid DNA samples in which tunneling from electrons and holes to an intercalator was investigated, we find that the distance between DNA duplexes is the dominant factor in the degree of transfer observed. In hydrated DNA samples intercalated with MX, the apparent distances and rates of hole and electron transfer to MX decrease as hydration level increases mainly because the distance between DNA duplexes increases with hydration. DNA complexing agents such as poly-lysine, polyethylenimine, nucleohistone, and cationic lipids also reduce the apparent transfer rates by reducing the amount of transfer between duplexes. Transfer rates in DNA complexed with spermine, however, are similar to those in equivalently hydrated MX-DNA. A double layer of cationic lipids is found to nearly isolate DNA duplexes from electron or hole transfer to adjacent duplexes. Our modeling of rates and distances of electron transfer in DNA-complexes allow for estimates of the spacing between DNA duplexes in each complex.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Electron Spin Resonance Study of Electron and Hole Transfer in DNA: Effects of Hydration, Aliphatic Amine Cations, and Histone Proteins

Cai

Sevilla

2001

J. Phys. Chem. B

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“…Low charge density of PEI was useful for degradation. Porphyrin molecules such as hemin could interact with a major groove of DNA [ 42 , 43 ]. It was known that PEI binding porphyrin could interact with DNA effectively than PAH binding one [ 43 ].…”

Section: Resultsmentioning

confidence: 99%

“…Porphyrin molecules such as hemin could interact with a major groove of DNA [ 42 , 43 ]. It was known that PEI binding porphyrin could interact with DNA effectively than PAH binding one [ 43 ]. Therefore, (H-PEH/DNA) 5 and hemin-containing (PEI/DNA) 5 film were decomposed by H 2 O 2 more effectively than other nanofilms.…”

Section: Resultsmentioning

confidence: 99%

Preparation of Hydrogen Peroxide Sensitive Nanofilms by a Layer-by-Layer Technique

et al. 2018

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H2O2-sensitive nanofilms composed of DNA and hemin-appended poly(ethyleneimine) (H-PEI) were prepared by a layer-by-layer deposition of DNA and H-PEI through an electrostatic interaction. The (H-PEI/DNA)5 film was decomposed by addition of 10 mM H2O2. H2O2-induced decomposition was also confirmed in the hemin-containing (PEI/DNA)5 in which hemin molecules were adsorbed by a noncovalent bond to the nanofilm. On the other hand, the (PEI/DNA)5 film containing no hemin and the (H-PEI/PSS)5 film using PSS instead of DNA did not decompose even with 100 mM H2O2. The mechanism of nanofilm decomposition was thought that more reactive oxygen species (ROS) was formed by reaction of hemin and H2O2 and then the ROS caused DNA cleavage. As a result (H-PEI/DNA)5 and hemin-containing (PEI/DNA)5 films were decomposed. The decomposition rate of these nanofilms were depended on concentration of H2O2, modification ratio of hemin, pH, and ionic strength.

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“…Their possible medicinal and biological applications have attracted tremendous interest [5][6][7][8][9][10][11][12]. During the past decade, increasing attention has also been focused on ruthenium(II) complexes that have been proposed as therapeutic agents in PDT and probes of DNA [13][14][15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 99%

A novel porphyrin–polypyridyl ruthenium(II) hybrid. Synthesis, characterization and photoinduced DNA cleavage activity

Liu

Zhao

et al. 2006

Transition Met Chem

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A novel porphyrin-polypyridyl ruthenium(II) hybrid compound, [C 4 -TPP-(ip)Ru(phen) 2 ](ClO 4 ) 2 (TPP = 5,10,15, ip = imidazo[4,[1,10]phenanthroline and phen = 1,10-Phenanthroline), in which a polypyridyl ruthenium(II) moiety is linked to a porphyrin moiety by a butyl chain, has been synthesized by the reaction of (C 4 ip)TPP with cis-Ru(phen) 2 Cl 2 in glacial acetic acid under an Ar atmosphere and characterized by elemental analysis, i.r., 1 H-n.m.r., u.v.-vis., ESI-MS and electrochemistry. Its photoinduced DNA cleavage activity was investigated preliminarily. It has been found that the hybrid compound promoted photocleavage of plasmid pBR 322 DNA upon irradiation. Singlet oxygen ( 1 O 2 ) is suggested to be the reactive species responsible for the cleavage.

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DNA Cleavage by a Polyethylenimine-appended Porphyrin

Abstract: Polyethylenimine (PEI)-appended porphyrin 2 bound DNA more strongly than non-polyethylenimine-appended porphyrins by creation of cationic charges of polyethylenimine and photochemically cleaved a double-stranded DNA.

Cited by 6 publications

References 16 publications

Electron Spin Resonance Study of Electron and Hole Transfer in DNA: Effects of Hydration, Aliphatic Amine Cations, and Histone Proteins

Electron Spin Resonance Study of Electron and Hole Transfer in DNA: Effects of Hydration, Aliphatic Amine Cations, and Histone Proteins

Preparation of Hydrogen Peroxide Sensitive Nanofilms by a Layer-by-Layer Technique

A novel porphyrin–polypyridyl ruthenium(II) hybrid. Synthesis, characterization and photoinduced DNA cleavage activity

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