Photoinduced DNA damage efficiency and cytotoxicity of novel viologen linked pyrene conjugates

Hariharan, Mahesh; Karunakaran, Suneesh C.; Ramaiah, Danaboyina; Schulz, Ina; Epe, Bernd

doi:10.1039/b924943e

Cited by 18 publications

(11 citation statements)

References 27 publications

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“…A large variety of photosensitizers have been linked to viologen subunits to facilitate intramolecular PET. Porphyrins,13–15 [Ru(bpy) 3 ],16, 17 pyrene,18 1,8‐naphtilimide,19 and many others20–22 have been studied. In addition, photoinduced charge separation can also be obtained by using self‐assembled systems 23–28…”

Section: Introductionmentioning

confidence: 99%

Ultrafast Photoinduced Electron Transfer in Viologen‐Linked BODIPY Dyes

et al. 2013

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New boron-dipyrromethene (BODIPY) dyes linked to viologen are prepared and their photophysical and electrochemical properties are investigated. Both synthesized molecules have similar electronic absorption spectra with the absorption maximum localized at 517 and 501 nm for dye 1 and dye 2, respectively. They exhibit well-defined redox behavior, highlighting the presence of BODIPY and viologen subunits, with little perturbation of the redox potential of both subunits with respect to the parent compounds. Both dyes are heavily quenched by photoinduced electron transfer from the BODIPY to the viologen subunit. The transient absorption technique demonstrates that dye 2 forms the viologen radical within a timeframe of 7.1 ps, and that the charge-separated species has a lifetime of 59 ps. Sustained irradiation of dye 2 in the presence of a tertiary amine allows for the accumulation of BODIPY-methyl-4,4'-bipyridinium (BODIPY-MV(+)), as observed by its characteristic absorption at 396 and 603 nm. However, dye 2 does not generate catalytic amounts of hydrogen under standard conditions.

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Section: Introductionmentioning

confidence: 99%

Ultrafast Photoinduced Electron Transfer in Viologen‐Linked BODIPY Dyes

et al. 2013

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“…On the contrary, the [2]pseudorotaxanes of cis - 1 ⊂CB[8] or cis - 2 ⊂CB[8] showed no condensation ability to pristine DNA, but displayed serious DNA damage upon UV light irradiation ( Supplementary Figures S47 and S48 ). These phenomena could be contributed to the photoinduced electron transfer process, through which the photo-activated viologen moiety in these [2]pseudorotaxanes can generate the reactive oxygen species to destroy the DNA structures 26 29 . Comparatively, no DNA damage was observed with the supramolecular complexes of trans - 1 ⊂CB[8] and trans - 2 ⊂CB[8] in the dark or by irradiating pBR322 DNA alone in the control experiments ( Supplementary Figure S49 ), indicating that the DNA damage was attributed to the reduced viologen in cis - 1 ⊂CB[8] and cis - 2 ⊂CB[8].…”

Section: Resultsmentioning

confidence: 99%

Photoresponsive Supramolecular Complexes as Efficient DNA Regulator

Cheng

Zhang

et al. 2014

Sci Rep

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Two supramolecular complexes of trans-1⊂CB[8] and trans-2⊂CB[8] were successfully achieved by the controlled selective complexation process of cucurbit[8]uril (CB[8]) with hetero-guest pair containing azobenzene and bispyridinium moieties in aqueous solution, exhibiting the reversibly light-driven movements of CB[8] upon the photocontrollable isomerization of azophenyl axle components. Significantly, the obtained bistable supramolecular complexes and their corresponding [2]pseudorotaxanes could act as a promising concentrator and cleavage agent to regulate the binding behaviors with DNA molecules.

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“…The exposure of PM2 DNA (10 μg mL −1 ) to visible light radiation (570 nm) in the presence and absence of the porphyrin derivatives was carried out on ice in phosphate buffer (5 m m KH 2 PO 4 , 50 m m NaCl, pH 7.4) by means of a halogen lamp (1000 W at 33 cm distance, 15 min). The modified DNA was precipitated by ethanol/sodium acetate and redissolved in BE1 buffer (20 m m Tris–HCl, pH 7.5, 100 m m NaCl, 1 m m EDTA), and DNA damage was quantified by means of a DNA relaxation assay, using repair glycosylases (Fpg and T4‐endonuclease V) as probes .…”

Section: Methodsmentioning

confidence: 99%

“…The study of interactions of ligands with biologically relevant molecules such as nucleic acids and proteins is an important area of research because such effective ligands can be useful as therapeutic and diagnostic agents . Among these, the investigations of DNA binding and mechanisms of damage generation by photoexcited molecules have attracted much attention, as these are highly relevant for the use of such molecules as antitumor agents and sensitizers in photodynamic therapy (PDT) . PDT is a novel modality for the cancer cell destruction mediated through reactive oxygen species and involves the combined action of light and a sensitizer.…”

Section: Introductionmentioning

confidence: 99%

Study of the Mode and Efficiency of DNA Binding in the Damage Induced by Photoactivated Water Soluble Porphyrins

Karunakaran

Ramaiah

Schulz

et al. 2013

Photochem & Photobiology

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We have investigated the DNA binding interactions and in vitro photoactivated DNA damage induced by a neutral water soluble porphyrin derivative 5,10,15,20-tetrakis(2,4,6-trihydroxyphenyl)porphyrin (TTHPP) and its zinc derivative 5,10,15,20-tetrakis(2,4,6-trihydroxyphenyl)porphyrinato zinc(II) (Zn-TTHPP) upon visible light irradiation through various spectroscopic techniques and employing repair endonucleases. These porphyrin derivatives exhibited high affinity toward DNA through groove binding interactions as evidenced through the UV-vis absorption, emission, circular dichroism spectral and viscosity changes. Interestingly, the free base porphyrin derivative, TTHPP generated efficient singlet oxygen mediated DNA damage sensitive to formamidopyrimidine-DNA glycosylase (Fpg protein), when compared with its metal derivative and to the well-known photosensitizer, hematoporphyrin. These results provide direct evidence for the role of DNA binding mode as well as extent of interactions with DNA in the efficiency of photoactivated DNA damage induced by the neutral porphyrins, which are believed to be the ideal candidates for photodynamic therapeutic applications.

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Photoinduced DNA damage efficiency and cytotoxicity of novel viologen linked pyrene conjugates

Abstract: Novel viologen linked pyrene conjugates permeate cells efficiently and exhibit spacer length dependent DNA damage and cytotoxicity upon photoexcitation.

Cited by 18 publications

References 27 publications

Ultrafast Photoinduced Electron Transfer in Viologen‐Linked BODIPY Dyes

Ultrafast Photoinduced Electron Transfer in Viologen‐Linked BODIPY Dyes

Photoresponsive Supramolecular Complexes as Efficient DNA Regulator

Study of the Mode and Efficiency of DNA Binding in the Damage Induced by Photoactivated Water Soluble Porphyrins

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