The interaction of methylene blue, azure B, and thionine with DNA: Formation of complexes with polynucleotides and mononucleotides as model systems

Tuite, Eimer; Kelly, John M.

doi:10.1002/bip.360350502

Cited by 130 publications

(95 citation statements)

References 50 publications

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“…No significant differences were observed between the 1-h and 16-h drug incubations, suggesting that the drug localizes rapidly in the nuclear region of the cells -an observation that broadly agrees with the limited microscopy evidence obtained in this study and with literature evidence. Methylene blue and other dyes of this structure have been reported to intercalate rapidly into DNA, binding predominantly to purine nucleotides (Tuite and Kelly, 1995). However, in our study, no residual DNA damage in MB-PDT-treated cells was observed after 4 hours' repair.…”

Section: Dna Damagecontrasting

confidence: 61%

A comet assay of DNA damage and repair in K562 cells after photodynamic therapy using haematoporphyrin derivative, methylene blue and meso-tetrahydroxyphenylchlorin

McNair

Marples²,

West³

et al. 1997

Br J Cancer

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Summary Single-cell electrophoresis (comet assay) has been used to evaluate DNA damage and repair in the human myeloid leukaemia cell line K562 after low-dose (predominantly sub-lethal) treatments of hyperthermia and photodynamic therapy (PDT). Three different photosensitizers were examined: haematoporphyrin derivative (HpD), methylene blue (MB) and meso-tetrahydroxyphenylchlorin (mTHPC). None of the drugs in the absence of light, nor in light alone, resulted in detectable DNA damage. However, a significant amount of DNA damage was detected immediately after treatment with haematoporphyrin derivative or methylene blue PDT compared with drug-only or lightonly treatments; no residual level of DNA damage was evident for either drug following a 4-h post-treatment incubation at 370C. No significant DNA damage was detected after meso-tetrahydroxyphenylchlorin PDT or hyperthermia either immediately or 4 h after treatment. We conclude that the alkaline comet assay can be applied as an effective screening assay for DNA damage induced by a range of laser therapies.

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Section: Dna Damagecontrasting

confidence: 61%

A comet assay of DNA damage and repair in K562 cells after photodynamic therapy using haematoporphyrin derivative, methylene blue and meso-tetrahydroxyphenylchlorin

McNair

Marples²,

West³

et al. 1997

Br J Cancer

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“…1.85 × 10 5 M −1 , which is comparable to the affinity of phenothiazine dyes for DNA. 36 Notably this is an order of magnitude higher than that seen for the unsubstituted analogue 2, demonstrating once more the importance of the 4-amino moiety and ICT character of 1.…”

Section: 2034mentioning

confidence: 88%

Synthesis and photophysical evaluation of a pyridinium 4-amino-1,8-naphthalimide derivative that upon intercalation displays preference for AT-rich double-stranded DNA

et al. 2012

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The synthesis, characterisation and solid state crystal structure of a cationic 4-amino-1,8-naphthalimide derivative (1) are described. The photophysical properties of 1 are shown to vary with the solvent polarity and H-bonding ability. The fluorescence of 1 is enhanced and blue-shifted in its 1 : 1 complex with 5′-adenosine-monophosphate while it is partially quenched and red-shifted in its complex with 5′-guanosine-monophosphate. Linear and circular dichroism measurements show that 1 binds to double-stranded DNA by intercalation. Comparative UV-visible and fluorescence studies with double stranded synthetic polynucleotides poly(dA-dT) 2 and poly(dG-dC) 2 show that 1 binds much more strongly to the AT polymer; 1 also has a strong preference for A-T rich sequences in natural DNA. Thermal denaturation measurements also reveal a much greater stabilisation of the double-stranded poly (dA-dT) 2 than of natural DNA.

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“…6a inset and Table 6), which are comparable to the affinity of phenothiazine dyes for DNA 23 and naphthalimides fused with heterocyclic rings. 24 Interestingly, the presence of the dimethyl substitution on the 4-amino nitrogen did not appear to have any significant effect on the DNA binding affinity of 3, in contrast to what was observed for the mononucleotides.…”

Section: Interaction With Salmon Testes (St)-dnamentioning

confidence: 64%

The effect of the 4-amino functionality on the photophysical and DNA binding properties of alkyl-pyridinium derived 1,8-naphthalimides

et al. 2013

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The synthesis and characterisation of two cationic pyridinium based 4-amino-1,8-naphthalimide derivatives (2 and 3) are described and compared to those of compound 1. The photophysical properties of 2 and 3 are shown to vary greatly with the solvent polarity and H-bonding ability. The dimethylamino substitution in 3 results in a weak quantum yield of fluorescence emission due to faster non-radiative deactivation of the excited singlet state than that seen for 2. As with 1, the fluorescence of 2 was found to be enhanced in its 1 : 1 complex with 5'-adenosine-monophosphate (5'-AMP) while it was partially quenched in its complex with 5'-guanosine-monophosphate (5'-GMP). In contrast, the fluorescence of 3 was enhanced ('switched on') in the presence of both adenine and guanine rich sequences. Linear and circular dichroism studies showed that each of 1, 2 and 3 binds to double-stranded DNA by intercalation. However, 2 and 3 do not show the preference for AT-rich DNA observed for 1. Comparative fluorescence studies with double stranded DNA show that the emission of 3 was 16 times enhanced in its DNA bound form, suggesting potential use of this structure as a spectroscopic probe for studying nucleic acid structure.

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The interaction of methylene blue, azure B, and thionine with DNA: Formation of complexes with polynucleotides and mononucleotides as model systems

Abstract: University of Dublin Dublin 2The interactions of methylene blue, azure B, and thionine with calf thymus DNA, [poly (dG-dC)12, [poly(dA-dT)

Cited by 130 publications

References 50 publications

A comet assay of DNA damage and repair in K562 cells after photodynamic therapy using haematoporphyrin derivative, methylene blue and meso-tetrahydroxyphenylchlorin

A comet assay of DNA damage and repair in K562 cells after photodynamic therapy using haematoporphyrin derivative, methylene blue and meso-tetrahydroxyphenylchlorin

Synthesis and photophysical evaluation of a pyridinium 4-amino-1,8-naphthalimide derivative that upon intercalation displays preference for AT-rich double-stranded DNA

The effect of the 4-amino functionality on the photophysical and DNA binding properties of alkyl-pyridinium derived 1,8-naphthalimides

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