Sequence‐dependent Interactions of Cationic Naphthalimides and Polynucleotides

McMasters, Sun; Kelly, Lisa A.

doi:10.1111/j.1751-1097.2007.00155.x

Cited by 11 publications

(4 citation statements)

References 41 publications

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“…The binding constant of the hybrid AT box was similar to that of [Poly(dA)-Poly(dT)], which meant that the compound 4a preferred to bind with AT-rich duplexes, no matter how hybridized the AT-rich duplexes were. The binding selectivity of the bis-naphthalimide derivatives was in accordance with similar compounds [ 28 ].…”

Section: Resultsmentioning

confidence: 55%

Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers

Huang

Song

et al. 2018

Molecules

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A series of bis-naphthalimide derivatives with different diamine linkers were designed and synthesized. All of the synthesized bis-naphthalimide derivatives were characterized by NMR and HRMS spectra. The binding ability between the compounds and CT DNA was evaluated by using UV–Vis titration experiments. The bis-naphthalimide compound with an ethylenediamine linker showed the largest binding constant with CT DNA. Hence, it was used as the model compound to study the DNA binding selectivity by UV–Vis titration aiming at different DNA duplexes. As a result, this compound showed binding preference to AT-rich duplexes. The DNA binding modes of the compounds were also measured by viscosity titration. The cytotoxicity of the compounds was evaluated by MTT assay. Compounds with 1,6-diaminohexane or 1,4-phenylenedimethanamine linkers showed higher cytotoxicity compared with other bis-naphthalimide derivatives.

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Section: Resultsmentioning

confidence: 55%

Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers

Huang

Song

et al. 2018

Molecules

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“…Sequence dependence intercalation behavior of polynucleotides and cationic naphthalimides 77–79 (Figure ) has been well documented by McMaster et al . UV‐Visible absorption spectra of these compounds were measured in the presence of increasing concentration of ct‐DNA, [poly(dA‐dT) 2 ] and [Poly(dG‐dC) 2 ].…”

Section: Bis–naphthalimide Derivativesmentioning

confidence: 73%

1,8‐Naphthalimide: A Potent DNA Intercalator and Target for Cancer Therapy

Tandon

Luxami

Kaur

et al. 2017

The Chemical Record

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The poor pharmacokinetics, side effects and particularly the rapid emergence of drug resistance compromise the efficiency of clinically used anticancer drugs. Therefore, the discovery of novel and effective drugs is still an extremely primary mission. Naphthalimide family is one of the highly active anticancer drug based upon effective intercalator with DNA. In this article, we review the discovery and development of 1,8-naphthalimide moiety, and, especially, pay much attention to the structural modifications and structure activity relationships. The review demonstrates how modulation of the moiety affecting naphthalimide compound for DNA binding that is achieved to afford a profile of antitumor activity. The DNA binding of imide and ring substitution at naphthalimide, bisnaphthalimide, naphthalimide-metal complexes is achieved by molecular recognition through intercalation mode. Thus, this synthetic/natural small molecule can act as a drug when activation or inhibition of DNA function, is required to cure or control the cancer disease. The present study is a review of the advances in 1,8-naphthalimide-related research, with a focus on how such derivatives are intercalated into DNA for their anticancer activities.

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“…An induced signal would be expected if it were groove-bound to the DNA as has previously been reported for the unsubstituted 1,8-naphthalimide. 11 An increase in the molar ellipticity of the CD band of double stranded DNA centred at 275 nm has been previously observed in the case of intercalative binding. 29 These changes along with LD measurements are indicative of the intercalative mode of binding.…”

Section: Circular Dichroism Spectroscopymentioning

confidence: 99%

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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Sequence‐dependent Interactions of Cationic Naphthalimides and Polynucleotides

Cited by 11 publications

References 41 publications

Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers

Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers

1,8‐Naphthalimide: A Potent DNA Intercalator and Target for Cancer Therapy

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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