Synthesis, photochemistry, DNA cleavage/binding and cytotoxic properties of fluorescent quinoxaline and quinoline hydroperoxides

Chowdhury, Nilanjana; Gangopadhyay, Moumita; Karthik, S.; Singh, N. D. Pradeep; Baidya, Mithu; Ghosh, Sudip Kumar

doi:10.1016/j.jphotobiol.2013.11.010

Cited by 22 publications

(14 citation statements)

References 40 publications

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“…Photoresponsive compounds afford exquisite temporal control of chemical reactions For example, several light‐responsive reagents have been developed to temporally control radical generation for DNA footprinting . These compounds generate

\cdot OH

or alkyl radicals, such as methyl (

\cdot {CH}_{3}

) or phenyl radicals, upon illumination with an appropriate wavelength causing DNA/RNA strand scission by abstracting a hydrogen atom from the sugar‐phosphate backbone of the polynucleotides.…”

Section: Introductionmentioning

confidence: 99%

Visible Light‐Induced Radical Mediated DNA Damage

McCue

Moreau²,

Shell

2018

Photochem & Photobiology

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Light-responsive compounds have been used to manipulate biological systems with spatial and temporal control of the event of interest. Illumination of alkylcobalamins with green light (>500 nm) produces carbon-centered radicals, which have been demonstrated to effectively cause DNA damage. Molecules that cause DNA and RNA strand scission are useful for studying polynucleotide structure and the binding of small molecules and proteins to polynucleotides. Most molecules that cause DNA damage in a light-dependent manner require high energy, short wavelength ultraviolet light, which is readily absorbed by nucleotide bases causing damage to the polynucleotides. Therefore, using alkylcobalamins is advantageous for causing strand scission of polynucleotides, because they are activated by light wavelengths that are not absorbed by nucleotide bases. Green-light illumination of methylcobalamin effectively causes DNA strand scission based on gel mobility assays. This cleavage is due to the generation of carbon-centered radicals based on the results of a radical trapping study. In addition, synthesis of an alkylcobalamin with a DNA binding moiety, spermine, improves DNA cleavage efficacy by an order of magnitude in comparison with methylcobalamin.

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\cdot OH

or alkyl radicals, such as methyl (

\cdot {CH}_{3}

) or phenyl radicals, upon illumination with an appropriate wavelength causing DNA/RNA strand scission by abstracting a hydrogen atom from the sugar‐phosphate backbone of the polynucleotides.…”

Section: Introductionmentioning

confidence: 99%

Visible Light‐Induced Radical Mediated DNA Damage

McCue

Moreau²,

Shell

2018

Photochem & Photobiology

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show abstract

“…They possess antiproliferative [6], anti-neoplastic [7], and cytotoxic properties [8]. Quinolines have been detected in meteorite extracts, and in general quinolines are of astrobiological interest, since this class of molecule includes nucleo bases, basic components of nucleic acids [9,10].…”

Section: Introductionmentioning

confidence: 99%

Molecular structure, FT-IR, FT-Raman, NBO, HOMO and LUMO, MEP, NLO and molecular docking study of 2-[(E)-2-(2-bromophenyl)ethenyl]quinoline-6-carboxylic acid

Ulahannan¹,

Panicker²,

Varghese

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…To gain information about the reactive species involved in the oxidative DNA cleavage reaction, we investigated the DNA cleavage in the presence of hydroxyl radical scavenger (DMSO), singlet oxygen quencher (NaN 3 ), and hydrogen peroxide scavenger (KI). It was found that DMSO (lane 4) and NaN 3 (lane 5) significantly reduce the nuclease activity of HPyETSC, indicating the participation of hydroxyl radicals and singlet oxygen in the cleavage process [40,41].…”

Section: Dna Interaction Studiesmentioning

confidence: 98%