Adenine-Thymine Base Pair Recognition by an Anthryl Probe from the DNA Minor Groove

Kumar, Challa V.; Punzalan, Emma H.A.; Tan, Willy B.

doi:10.1016/s0040-4020(00)00526-3

Cited by 89 publications

(98 citation statements)

References 14 publications

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“…To obtain the binding constants, the spectral data were fitted to a simple Scatchard model by using Equation (1) (see the Experimental Section). [17] The values that were obtained spanned between (2.20 AE 0.01) 10 3 m À1 and (1.95 AE 0.01) 10 4 m À1 ( Table 1) and indicated that these compounds have a moderate affinity to CT DNA. As a general trend, we can say that the compounds that contain the terminal anthracenyl group (L 1 , L 2 and 7) have a smaller affinity to DNA than those that bear the same polyaromatic structure at the 4-position of the pyrazolyl ring (L 3 , L 4 and 9).…”

Section: Uv-visible Spectroscopy Studiesmentioning

confidence: 95%

“…The titration data were fitted to a simple Scatchard model, or to the McGhee-von Hippel site-exclusion model to obtain the intrinsic binding constant (K b ). [17,19] All calculations were done by considering the DNA concentration in base pairs, and the data were corrected for volume changes.…”

mentioning

confidence: 99%

“…The absorption titration data were fitted to Equation (1), [17] where D is the concentration of DNA in base pairs and De ap = [e a Àe F ] and De = [e B Àe F ].…”

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confidence: 99%

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Pyrazolyl–Diamine Ligands That Bear Anthracenyl Moieties and Their Rhenium(I) Tricarbonyl Complexes: Synthesis, Characterisation and DNA‐Binding Properties

Vítor¹,

Correia²,

Videira³

et al. 2007

ChemBioChem

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Two novel families of pyrazolyl-diamine ligands that bear an anthracen-9-yl group as a DNA-binding fragment, pz*(CH2)2NH(CH2)2NHCH2-9-anthryl (pz*=pz (L(1)), 3,5-Me2pz (L2)) and pz*(CH2)2NH(CH2)2NH(2 (pz*=4-(9-anthrylmethyl)pz (L3), 3,5-Me2-4-(9-anthrylmethyl)pz (L4)), have been prepared and fully characterised. In the case of L2-L4, the evaluation of their coordination capability towards the fac-[Re(CO)3]+ core led to the synthesis of the organometallic complexes fac-[Re(CO)(3){3,5-Me(2)pz(CH2)2NH(CH2)2NHCH2-9-anthryl}]Br (7) and fac-[Re(CO)3{4-(9-anthrylmethyl)pz*(CH2)2NH(CH2)2NH2}]Br (pz*=pz (8), 3,5-Me2pz 9). The interaction of the novel pyrazole-diamine ligands and the rhenium(I) complexes with calf thymus (CT) DNA has been investigated with a variety of spectroscopic techniques (UV-visible, fluorescence, circular dichroism (CD) and linear dichroism (LD)). All of the evaluated compounds have a moderate affinity to CT DNA (3.46x10(3)

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Section: Uv-visible Spectroscopy Studiesmentioning

confidence: 95%

mentioning

confidence: 99%

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Pyrazolyl–Diamine Ligands That Bear Anthracenyl Moieties and Their Rhenium(I) Tricarbonyl Complexes: Synthesis, Characterisation and DNA‐Binding Properties

Vítor¹,

Correia²,

Videira³

et al. 2007

ChemBioChem

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“…These bands are ascribed to the anthracene and pyrene chromophores attached to the phenanthroline moiety. [35,36] The high-energy bands (aip: 251 nm; pyip: 234 and 280 nm) are attributed to the πǞπ* transitions corresponding to the phenanthroline moiety of the ligands.…”

Section: Thementioning

confidence: 99%

Effects of Anthracene and Pyrene Units on the Interactions of Novel Polypyridylruthenium(II) Mixed‐Ligand Complexes with DNA

Mariappan

Maiya

2005

Eur J Inorg Chem

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2‐(9‐Anthryl)‐1H‐imidazo[4,5‐f][1,10]phenanthroline (aip) and [2‐(1‐pyrenyl)‐1H‐imidazo[4,5‐f][1,10]phenanthroline (pyip) and their complexes [Ru(phen)2(aip)]2+ (1) and [Ru(phen)2(pyip)]2+ (2) (phen = 1,10‐phenanthroline) have been synthesized and characterized by elemental analysis, UV/Vis, IR and 1H NMR spectroscopy, FAB‐MS and cyclic voltammetry methods. Both 1 and 2 are redox‐active and undergo oxidation at 1.43 and 1.47 V (vs. SCE), respectively. Both 1 and 2 show only the 3MLCT emission typical of any polypyridylruthenium(II) complex. These new complexes are seen to be excellent binders of calf‐thymus (CT) DNA, as revealed by the results of absorption, luminescence, viscometric titrations, and thermal denaturation studies. These results also indicate that while ruthenium‐bound aip and pyip intercalate within the base pairs of the duplex, the phen moieties act only as spectator ligands in each case. Steady‐state emission studies carried out in aqueous media with and without DNA reveal that [Ru(phen)2(pyip)]2+ is a better “molecular light switch” for DNA than [Ru(phen)2(aip)]2+. Under an identical set of experimental conditions of light and drug dose, the DNA photocleavage ability of [Ru(phen)2(pyip)]2+ is also higher than that of [Ru(phen)2(aip)]2+. “Inhibitor studies” suggest that the oxygen species are mainly responsible for the DNA photocleavage by these complexes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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“…Unfortunately, anthracene and most of its derivatives are hardly soluble in water, which constitutes a major drawback for the application of this fluorophore in biologically or physiologically relevant media. Although the introduction of appropriate substituents may increase the solubility in aqueous media, [29][30][31][32][33][34] the synthesis of such compounds is often tedious and time-consuming or the solubility-mediating functionalities interfere with the desired photophysical properties of anthracene. With this shortcoming in mind we turned our attention to the isoelectronic, but water-soluble benzo[b]quinolizinium (2a, Chart 1), 35,36 that is also named 4a-azoniaanthracene or acridizinium, in which one bridgehead carbon atom of the anthracene scaffold is replaced with a quaternary nitrogen atom, yielding a permanent positive charge.…”

Section: Introductionmentioning

confidence: 99%

The benzo[b]quinolizinium ion as a water-soluble platform for the fluorimetric detection of biologically relevant analytes

Granzhan¹,

Ihmels²,

Tian³

2015

Arkivoc

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In this Account our efforts are described to establish the benzo[b]quinolizinium ion, also known as acridizinium or 4a-azoniaanthracene, as a water-soluble surrogate of anthracene for the development of selective fluorescent probes. It is demonstrated with selected examples that especially the 9-aminobenzo[b]quinolizinium is a donor-acceptor dye with favorable absorption and emission properties and may be used as a versatile building block for fluorescent light-up probes and ratiometric probes.

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Adenine-Thymine Base Pair Recognition by an Anthryl Probe from the DNA Minor Groove

Cited by 89 publications

References 14 publications

Pyrazolyl–Diamine Ligands That Bear Anthracenyl Moieties and Their Rhenium(I) Tricarbonyl Complexes: Synthesis, Characterisation and DNA‐Binding Properties

Pyrazolyl–Diamine Ligands That Bear Anthracenyl Moieties and Their Rhenium(I) Tricarbonyl Complexes: Synthesis, Characterisation and DNA‐Binding Properties

Effects of Anthracene and Pyrene Units on the Interactions of Novel Polypyridylruthenium(II) Mixed‐Ligand Complexes with DNA

The benzo[b]quinolizinium ion as a water-soluble platform for the fluorimetric detection of biologically relevant analytes

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